No one chooses not to spend time on something with a clear upside. So, to most sellers' surprise, when a deal requires “no time” to maintain, I don't usually see that as an opportunity.

Today’s deal is an email marketing tool built for SaaS companies: behavior-based emails, automated workflows, segmentation, and lifecycle messaging. Founded in June 2020, bootstrapped, and run by salaried operators while the owners build their next thing.

• Asking $1.9M, advertised at 2.7x profit, 2.1x revenue

• TTM revenue $917.1k, TTM profit $696.1k

• Last month: $29.9k revenue, $9.9k profit

• ARR $376k, churn 3-5% “stable”

• ~150 paying customers, operators cost $7.8k/mo

• React, Node, Postgres on AWS Lambda

In the seller’s defense, they’ve shown another tool they launched recently that went from $9k to $43k in MRR in under two months, which is why they’ve shifted their focus and are looking to sell this one.

First time here? We analyze the deal flow and market trends we come across for independent buyers, search fund operators, and anyone seriously considering buying or selling a company.

In short

• $917k TTM revenue, $376k ARR, $29.9k last month. The current month and the ARR match. But roughly $541k of the trailing year is gone.

• The advertised 2.7x profit is priced off the old numbers. Against the run rate, $1.9M is 16x profit, and still 9x with operator salaries added back.

• Competitors are Customer.io, Loops, and Resend, not Mailchimp or Klaviyo. Customer.io retains 111% of existing revenue. This loses a third.

• The email provider matters. On SES, costs are lower, and the customer base is likely clean.

• I’d pass at $1.9M. At 2.5-3x run-rate SDE, this is a $300-400k deal, seller-financed or earnout-backed, for a buyer already in the space.

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The financials don’t add up

The business averaged $76.4k a month over the trailing year. Last month it did $29.9k. The stated ARR of $376k is $31.3k of MRR, so the current month and the ARR match, and roughly $541k of the trailing revenue is unaccounted for. Either MRR fell by more than half after the sellers walked away in August 2025, or much of the revenue wasn’t recurring.

Margin went from 76% over the year to 33% last month, with costs flat at $18-20k, so the decline is entirely due to revenue.

$1.9M against the run rate is 5.3x revenue and 16x profit. Add back $93.6k of operator salaries, and the run-rate SDE is about $212k. Still 9x.

The sellers also mentioned “good cash flow when yearly plans are purchased” as a selling point. It’s the opposite. That’s cash already collected for the service the buyer still has to deliver. I’d get the deferred revenue schedule and deduct it at closing.

Neglect kills email tools

Switching ESPs is a hassle (re-implementing event tracking, rebuilding workflows, re-warming domains), and that friction is this category’s appeal. But a product this “sticky” doesn’t lose half its revenue in ten months of absentee ownership.

Deliverability can’t be neglected. Gmail and Yahoo began enforcing bulk-sender requirements in February 2024: authentication, one-click unsubscribe, and complaint rates under 0.3%. Microsoft also began rejecting non-compliant high-volume mail since May 2025. An unmaintained ESP leads to lower open rates, customers blame the tool, and they migrate.

AWS Lambda can’t run persistent SMTP, so sending goes through SES or a third-party API. Which provider matters.

SES is the cheapest option (~$0.10 per thousand sends) and the strictest: AWS reviews accounts at 0.1% complaint rates, and pauses sending near 0.5%. If they’re still running on SES, it’s a good sign, since a bad customer base would have been suspended by now. If they’re with other providers, the tolerance is higher, but the cost is also several times that of SES.

I’d want to know what the complaint rates, blocklist history, and inbox placement look like before engaging.

Competition

The seller names Omnisend, Brevo, ActiveCampaign, Klaviyo, and Mailchimp as competitors. Those serve e-commerce and SMBs. A product pitched as “email built for SaaS companies” competes with Customer.io, Loops, and Resend.

Sacra estimates Customer.io passed $100M ARR in September 2025, growing 37%, with $38.8M raised. Loops also raised $3.2M to serve exactly this segment, with a free tier, unlimited seats, and transactional email included. Resend has taken the developer end, and Brevo’s free tier covers everyone too small to pay for anything.

The seller calls their 3-5% churn “stable.” If that’s the monthly figure, it’s 31-46% of the base per year, which explains the revenue decline on its own. The rate may be stable, but the customer base certainly isn’t. Customer.io retains 111% of existing revenue in this same category, while this deal loses a third of its revenue annually.

Questions I’d ask

The financials are concerning, so I’d start there.

• Twenty-four months of monthly MRR, revenue, and customer count. Cash or accrual, stated explicitly.

• What exactly is the $541k gap between TTM revenue ($917k) and ARR ($376k)? Services? Annual prepays? Churned accounts?

• How much have customers prepaid for service not yet delivered?

• Is the 3-5% churn monthly or annual? Gross revenue churn, not just logo churn.

• What share of MRR sits in the top ten customers?

• What does the “7% annual growth rate” measure?

Then the sending infrastructure.

• Which provider (SES/SendGrid/Postmark) is being used, and is the account in good standing? SES is the cheapest, but also the strictest on suspension.

• Monthly sending volume, complaint rates, bounce rates, and blocklist incidents over the last twelve months?

• Are the customer’s sending domains DMARC-compliant?

And lastly, what do the operators actually do? What are their contracts, and will they stay?

So would I do the deal?

Absolutely not at $1.9M. The founders are trying to cash out based on a historical financial profile that completely vanished over the winter.

On a current run-rate basis, adjusting for market competition and churn, a fair multiple would be between 2.5x and 3.0x SDE. If the codebase is solid and the remaining customer base is proven sticky, a realistic valuation is between $300,000 and $400,000.

The deal would need to be structured with some seller financing or a performance-based earnout to offset the risk of decline, too. If the sellers want to hold out for a million-plus valuation based on old data, let them keep ignoring it until the revenue hits zero.

That said, I do see an opportunity in this space despite the competition. Software is no longer the bottleneck it used to be, and you could compete with the larger names by running far leaner than they do. So, the buyer who fits is someone in this space who can absorb the customers onto infrastructure that is actually maintained. For everyone else, you’d have to fight someone else’s battle because they decided this was no longer worth their time.

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Evernomic Confidential only covers third-party deals we come across. We never write about anything Evernomic represents or holds a financial interest in. This analysis is for informational purposes only. It isn’t investment, financial, or legal advice, and we can be wrong. Do your own diligence before acting on any deal.

Hello everyone, and happy Tuesday,

It’s no secret that newsletters are booming. From 8- to 9-figure exits like Morning Brew, Axios, and The Free Press to platforms like Substack and beehiiv going mainstream, or even my girlfriend asking me why every founder has a damned newsletter now. It’s the new thing, or better said, has been for a few years, and the masses are catching on.

1440 is a daily newsletter I’ve been reading for some time now, and it was recently valued at $101 million, with $27 million in annual revenue, and only a 27-person team. So how did a “simple” newsletter get to this position, and where is the money coming from?

First time here? We analyze the deal flow and market trends we come across for independent buyers, search fund operators, and anyone seriously considering buying or selling a company.

In short

• 1440 is a bootstrapped 27-person daily newsletter doing $27M in all-ad revenue. A 409A mark from an investment bank valued it at $101M (3.74x).

• Curated newsletters like 1440 command ~$8.50 CPCs. Each email reaches ~2.8M readers, and each sponsorship generates $60K to $100K.

• 70% paid growth, 30% organic. Paid acquisition runs at $1M/month with a ~$3 CAC and a 4-month payback.

• Morning Brew (3.8x) is the only clean comp. Every higher multiple in the space was either strategic (HubSpot, NYT, Paramount) or subscription/B2B (Athletic, Industry Dive).

• Doubling down on AI-replaceable evergreen content is the wrong play. The right one is using their distribution to launch independent vertical brands or a venture arm.

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1440 is precisely the romantic kind of media company people fall in love with. Their name is drawn from the 1,440 minutes in a day, and also the year Johannes Gutenberg invented the printing press.

The newsletter was founded in 2017 by Tim Huelskamp, Andrew Steigerwald, and the late Pierre Lipton, with an email sent to 78 friends and family members that offered a five-minute, unbiased briefing on what was going on in the world.

Today, that same email is sent to over 4.7 million subscribers. Their Daily Digest reads 100+ sources every morning and extracts an unbiased briefing that is reviewed by at least five colleagues. They’ve also introduced a library of evergreen explainers covering topics from business and finance to health and medicine. Alongside it sit multimedia properties like a podcast and a YouTube channel.

All of it fuels on their flagship newsletter, rather than a Google ranking or a social feed they’re renting.

A daily newsletter valued at $101 million

According to CEO Tim Huelskamp, the company received a third-party valuation of $101 million earlier this year, as originally reported in On Background by Mark Stenberg.

You typically hear a number like this after a fundraising round or an acquisition. 1440 is neither looking to raise capital nor exit. The team holds equity, the company distributes dividends, and the IRS requires a third-party fair value for options and share pricing, so they had an investment bank mark the business at 3.74x revenue.

$1 million revenue per employee

$27 million in annual revenue is impressive even by SaaS standards. To put things into perspective, this single newsletter generates more than half of what either Substack ($45M) or beehiiv ($34M) generated last year. The economics are incomparable, but the scale is no joke.

I spoke to Teddy Burkhardt, VP of Content at 1440, who confirmed that all of that revenue comes from ads.

And 1440 does this with a bootstrapped 27-person team. Around this time two years ago, they were doing $15m in revenue with 15 people. They’ve maintained that ratio over the past two years, and none of the comps match it. Morning Brew, Axios, and The Free Press all carried far bigger teams, and most took venture money.

The advertising economics

To understand the numbers, I looked at sponsorship rates for two sets of newsletters:

• “Curation” brands like Superhuman AI, Techpresso, and Morning Brew.

• “Legacy” names like Business Insider, Inc, Entrepreneur, Fast Company, and a few others.

There’s not much science to my picks, but I took the average cost per click for every brand, then the median of each group, with 28 brands across both groups.

At a similar scale, the first group lands around $8.50 per click. The second group sits near $117 per click, with some even running past $350, which is essentially just a prestige buy and an anomaly. The legacy names often get opened out of habit or when a headline catches your eye, which is reflected in their click-through rates. But people pay more attention to the curators with a clear voice.

1440 doesn’t publish its rates publicly, but we can guess. With 60% open rates and 4.7 million subscribers, there’s roughly 2.8 million opens per email. Price that at the former CPC rate, and a main sponsorship comes out around $60k to $100k. AdWeek pegged the flagship near $100,000 per day, which lines up.

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Growth channels and paid acquisition

With $1 million in monthly ad spend, approximately 70% of 1440's growth comes from paid channels, with a ~$3 CAC per double-opt-in subscriber. This helps their case against media companies that can’t explain where their audience comes from, other than by throwing around the word “organic”.

Tim mentioned in an interview with Press Gazette that their revenue per opened email is around $0.05. Assuming a monthly cycle of 25 emails and 60% open rates, resulting in approximately 15 opens per month per subscriber:

Monthly revenue per subscriber = 15 opens * $0.05 = $0.75/month

Consequently, the payback period for capital deployed in paid marketing is around 4 months. The remaining growth is organic, driven by word of mouth and over 2 million followers across Instagram, Facebook, and X.

Given that they bootstrapped, their growth strategy hasn’t always been so reliant on paid channels:

• 0–1,000 Subscribers: Solely focused on content and feedback loops.

• 1,000–50,000 Subscribers: Low-cost channels like cross-promotions and DojoMojo giveaway sweepstakes.

• 50,000–100,000 Subscribers: Revenue was funneled into Facebook Ads with CAC between $1.00 to $2.00.

• 100,000–500,000 Subscribers: Diversified acquisition across other channels, including Google, Reddit, Pinterest, Quora, and LiveIntent.

• 500,000–Present: Scaled programmatic acquisition to over 300,000 new subscribers monthly, testing over 1,500 ad creatives per quarter via external agencies.

They also run a strict list-cleanup schedule, with re-engagement campaigns as the first step before any inactive subscriber gets removed.

Comps

The only clean comp for 1440 is Morning Brew. Insider acquired it in October 2020 for around $75M in cash, with the founders retaining a minority stake and an earn-out. It was tracking over $20M in revenue and $6M in profit that year, and profitable since 2018. Ad-supported, free, general audience. Sold at 3.8x revenue.

Although, admittedly, the newsletter space was much less competitive in 2020.

Other comps may trade at high multiples, but that’s either due to strategic integration or a subscription-based revenue model.

• The Hustle sold to HubSpot in 2021 for $17.2M cash per HubSpot’s SEC filing (not the widely spread $27M). HubSpot bought the audience at under $2/sub to feed its SaaS funnel.

• Axios sold to Cox in August 2022 for $525M, roughly 5x on $100M+ revenue. Profitable for three prior years but at a loss in 2022 as it pushed into local. Cox was also positioning for political ad inventory ahead of the midterms and 2024 elections.

• Industry Dive sold in 2022 for $389M cash, about 5x revenue, and 11.4x EBITDA. Pure B2B across 27 trade publications, PE-owned pre-sale. The premium is recurring revenue tied to high-intent professional audiences.

• The Athletic sold to the NYT in January 2022 for $550M all-cash, 8.5x on 1.2M paid subscribers. NYT paid because those subscribers fit in their premium content push.

• The Free Press sold to Paramount Skydance in October 2025 for $150M, 7.5x on ~$20M ARR (170K paid, 1.5M total). The deal also installed Bari Weiss as Editor-in-Chief of CBS News, which certainly influenced the terms.

Every high multiple was strategic. A financial buyer, search fund, or PE likely wouldn’t have paid those numbers. And the high multiples cluster around subscription or B2B revenue, not ad-supported, general-audience revenue.

So 1440, valued at $101 million, is forward-looking and not a discount.

What could justify a 9-figure valuation?

Traditional digital publishers (e.g., BuzzFeed, Vice) experienced catastrophic value destruction due to their reliance on search traffic. 1440’s email list is insulated from search engines and AI conversational tools that increasingly disintermediate standard web traffic.

However, 1440 is doubling down on generalist evergreen content right as AI commoditizes exactly that. Low-depth, high-breadth educational content is the most AI-replaceable format and serves as an SEO asset in a world where search traffic is collapsing.

I don’t see the need to become an education company. 1440 is an informer. Once you’re part of someone’s routine, the brand sticks. I’d leverage that to build other independent brands that don’t cannibalize 1440.

But not in the way Morning Brew or Axios have.

Think about it: when someone says “Morning Brew,” how many think of the flagship newsletter vs. their adjacent verticals like Tech Brew or Marketing Brew? Morning Brew will always be tied to its flagship, and 1440 should be too.

New ventures need their own identity.

They can launch new media brands and beat every competitor on the economics by using their existing distribution as the launch channel. Their audience may be general, but there are specialists in any large enough group. Those specialists can become higher-value subscribers in dedicated brands, rather than remaining “cheap” inventory on the main list.

Plus, this strategy lets you exit the new brands before multiples begin to decline as they scale. The proceeds could even fund more passive investments.

I know firsthand that some of the largest media outlets are launching venture arms, and some plan to rely solely on their prestige and ad credits within their own distribution as their entire buy-in. 1440 could beat that on every level.

Tim is a private equity guy himself. He probably knows this better than I do.

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Evernomic Confidential only covers third-party deals we come across. We never write about anything Evernomic represents or holds a financial interest in. This analysis is for informational purposes only. It isn’t investment, financial, or legal advice, and we can be wrong. Do your own diligence before acting on any deal.

Dividend investors are some of the stickiest users on the internet. They’re just like day traders, but they actually have some degree of patience, or at least they think so. Once someone commits to an app, they defend it like a religion and show it off to all their other investor friends.

Today’s deal is a freemium dividend-focused portfolio tracker. You connect your brokerage, and it shows your dividend income, yield, upcoming payouts, and projects your future income. Bootstrapped, and founders want to move on.

• Asking $650k, 3.4x profit, 2.5x revenue

• TTM revenue $262k, TTM profit $191k, 73% margin

• Last month: $19.9k revenue, $11.5k profit

• Churn 5-10%, 3,000+ paying customers

• 120,000+ users in the database, founded June 2021

• Laravel, Vue, and Flutter stack with brokerage integrations

If you’re new here, we analyze the deal flow and market trends we come across. Looking to buy or sell? Reply to this piece.

In short

• The financials are declining. Annualize last month’s numbers, and you get $239k revenue and $138k profit, both below the trailing year. So it isn’t 3.4x. On run-rate profit, you’re paying 4.7x.

• Margin fell from 73% to 58% in a few months, a 15-point drop that’s probably the new AI feature burning cash or a sharp decline in users.

• ARPU is ~$5.30 a month. You can’t buy users at that price, so it runs on free traffic alone, and the traffic is flat.

• The niche is crowded with cheaper rivals, and the brokerages already do this for free. Integrations and data feeds cost a fortune to run, so it’s at a disadvantage.

• The primary asset is the list of 120,000 income investors, and there may be an opening to introduce social features or a media front to monetize attention.

• I’d pass at $650k. Comps sit at ~2.8x profit. There’s a deal only far lower, seller-financed, and only for a buyer who can do something with the list.

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The listing is anonymized, so I can’t share month-by-month trends, but last month it generated $19.9k in revenue and $11.5k in profit. Annualize those, and you get about $239k and $138k, both below the seller's trailing figures of $262k and $191k. The financials are declining.

The listing references 3.4x trailing profit, which would be fair if it were true. But pay $650k against $138k of run-rate profit, and your actual multiple is 4.7x. I’d bet the multiple is even higher against the most recent months.

The margin doesn’t check out either. Across the year, it’s 73%, and last month it’s 58%. A 15-point drop over a few months usually indicates that a new cost has been added or that pricing has been reduced. I assume the OpenAI entry in the tech stack means they recently bolted on an AI insights feature. If that’s it, you’re paying API costs every month for something that, given flat usage and steady churn, probably doesn’t generate a return. I’d want to see monthly margins for the last twelve months, not the blended number.

The risks (and there are plenty)

The consumer finance space is an attractive space. Money gets thrown around. But it’s also highly competitive, and I don’t mean just in terms of literal competitors. CPC and CPM rates in finance are through the roof because there’s always someone who’s willing to outbid you, so paid acquisition becomes tricky. You either need to own your distribution or you need ridiculously high ARPU and LTV for the economics to work, which this app doesn’t have.

To estimate ARPU for this business, roughly $192k ARR across ~3,000 payers is about $5.30 per month. At that price, you cannot profitably acquire a user through any paid channel, so the business is dependent on organic and SEO.

Dividend tracking, specifically, is one of the most crowded niches in consumer finance. Sharesight has over 500,000 users; Getquin runs a free, ad-funded tier on a similar basis with $27m+ funding; and Snowball, Stock Events, DivTracker, and Capitally all cluster around $4 to $8 per month. Above all of them, brokerages keep adding native dividend-income views and calendars, which removes any reason a casual investor would pay for a separate app at all. Review sites in the space now routinely tell people to use a free tool or their broker’s built-in features.

Broker integrations and data feeds

My instinct for this sort of product would be to offer it for free and monetize elsewhere, but that becomes difficult if you have to pay a fortune just for your app to function.

A US dividend tracker connects via providers like Plaid or Yodlee (or scrapes), and investment account aggregation is both expensive per connection and notoriously poor at delivering clean dividend and corporate action data. You also need to ensure those connections transfer smoothly during an acquisition. If you have to force 3,000 paying users to re-link their brokerages, the re-auth prompt alone kills you.

Forward income projection also requires a licensed dividend-estimates feed. “Future income projections” and ex-date/payout data aren’t free. I remember back when I was building market analysis software, those very data vendors were the biggest pain in my neck.

The value may be in the list

Owning distribution in this niche is invaluable. I know a crypto humor Twitter page that makes $500k/year from a single sponsorship deal.

This app has (optimistically) 120,000 dividend investors. Brokerages, ETF issuers, and fintech tools all pay to reach exactly those people, and an income-investing newsletter to that list could plausibly earn more than the $16k a month the subscription generates. I’d treat the users as the core asset and build a media channel to serve them, monetized through sponsorships and brokerage affiliate relationships. I’d keep the tracker as the free hook that retains the audience rather than my selling point. This doesn’t necessarily need to be in the form of a newsletter. There are various finance apps with a consumption feed.

But as a counterweight to my own argument, the 120k “users” are almost certainly inactive in the majority. The app has been around for 5 years. If they had actually managed to retain users from their older cohorts, they likely wouldn’t be selling right now. Cold-blasting 120k stale addresses trips spam filters and drives sender reputation to the ground. The actual user base is anyone who has opened an email or the app in the last 90 days.

Trading 212 is one of my favorites, largely because of its social features, like sharing your “investment pie”. Building out features like that to retain users and increase DAU is the only path I see forward.

Demographics

Income investors skew older and wealthier, which is precisely who dividend-ETF sponsors and brokerages want to reach, so the ad/referral economics here are admittedly better than generic fintech. That said, the dividend-growth-investing crowd is unusually sales-resistant and frugal by self-selection.

I mentioned earlier that dividend investors were sticky users. While that may be an advantage in the context of existing users and new sign-ups, it also means it’s going to be that much more difficult to convince new users to migrate away from competitors to begin with. Dividend tracking isn’t a revolutionary, new concept. Most of your target audience already has an app they’re loyal to. The one opening I see is to target the trend of teenagers and people in their twenties getting into investing for “passive income.” The caveat is they’re a less valuable audience than established investors, but that’s where you stand a better chance.

Showing some personality could go a long way in converting a younger audience. Social features would also make every new user more likely to bring a couple of friends with them.

Questions I’d ask

I’m going to avoid the obvious (but important) questions around the use of language and whether this is clearly framed outside the scope of financial advice.

First, I’d want the last twelve months of monthly revenue, profit, and customer counts, not the blended trailing figures.

• Why does ARR ($192k) sit below trailing revenue ($262k), and what exactly is the non-recurring piece?

• Is the 5-10% churn monthly or annual?

• What’s the voluntary versus involuntary churn split?

Better card retries and pre-dunning emails can recover failed payments. If the seller hasn’t done that, it’s a lever the new buyer could pull immediately.

The user base is the most important asset, but it’s, again, only anyone who has opened an email or the app in the last 90 days.

• How were the 120,000 users acquired?

• How many are reachable by email, and what’s the opt-in status of that list?

• What’s the DAU and MAU? Are there new sign-ups coming in now?

On the product side, the only edge over free trackers and the brokerages is forward income projection and tax-aware reporting, which is what Sharesight charges for. So does it actually do that, or does it just show a yield?

• Does it adjust cost basis for return of capital and split qualified from ordinary dividends, or is it just a yield number?

• How do the brokerage integrations work, who maintains them, and how often do they break?

• What does the AI feature cost to run, and did it move retention at all?

• If it’s sending users’ holdings to a third-party AI, did users consent to that in the privacy terms?

So would I do the deal?

Certainly not at $650k, and probably not at all.

We recently sold an AI economic calendar SaaS with similar financials at 2.2x TTM revenue. The multiples on this deal are far too high.

Marketplace data on Acquire.com and Flippa for deals like this one runs anywhere from the low 2x to the mid 3s, and averages around 2.8x profit. You can’t value a business on revenue or profit alone, but there’s no standout metric and no unfair advantage here to lift the multiple.

The opening is the 120,000-investor list, with all the questions above still open. On that basis, I’d engage lower and structured, somewhere in the low three hundreds, with a good amount tied to revenue or retention holding through the next year, and the founders carrying part of that risk through the transition. If the list is clean and reachable, there’s a deal. If it’s mostly dead signups that no one can email, there isn’t one at all.

The buyer who fits this is a competitor, or someone who can put a higher-ticket offer in front of that audience right away. They can roll users into a healthier business instead of fighting a losing battle to grow this one. That’s also the buyer who can do it on heavy seller financing, since their track record and alignment reassure the seller that they stand a better chance. If I were advising the seller, I’d approach a few competitors immediately.

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Evernomic Confidential only covers third-party deals we come across. We never write about anything Evernomic represents or holds a financial interest in. This analysis is for informational purposes only. It isn’t investment, financial, or legal advice, and we can be wrong. Do your own diligence before acting on any deal.

I have only been writing and reading M&A newsletters for approximately 2 months. My experience has been interesting to say the least… How is a buyer going to interpret this? How much opinion should I include? Does this even make sense? These questions frequent my mind more than I’d like to admit when I’m writing. That’s why it’s important to learn from those who have nailed it already.

The 7 M&A Newsletters I’ll be covering today

1. Axios Pro Rata

2. Evernomic Confidential

3. SMB Deal Hunter

4. Reuters Deals

5. PE Hub

6. The Daily Pitch (Pitchbook)

7. Exec Sum

What makes a good M&A Newsletter

Through my recent experiences, I’ve noticed six criteria that make an M&A newsletter valuable and enjoyable to me. I have selected my 7 picks through the lens of these factors, so keep them in mind.

1. A point of view, not a feed. Anyone can list and describe deals. Newsletters worth inbox space must tell you what a deal means below the surface. What the headline missed, or what the seller is not saying. I want to see the angle and the risk.

2. Actionable value. Curated beats comprehensive. One deal explained well beats fifty deals dumped in a list. A good newsletter respects your time.

3. The right job for the moment. Some you read for the breaking headline; some for the slow, deep take (the analysis pieces). The best readers stack two or three that do different jobs.

4. Credibility of the writer. Who’s behind it? A sourced journalist, a data house, an operator who’s actually bought companies? The byline is half the product.

5. A format you’ll actually open. Skimmable, consistent shape, reads fine on a phone. If you dread opening it, it doesn’t matter how smart it is or who wrote it. Goes hand in hand with point two, a well-written newsletter respects your time.

6. An edge you can’t get elsewhere. Off-market deals, proprietary data, exclusive interviews, or simply a take you trust. The best ones give you something the free firehose can’t.

The 7 M&A Newsletters

1. Axios Pro Rata

Axios Pro Rata by Dan Primack sets the bar for me, hence earning #1 on my list. It’s “newsy but with a take.” And covers mergers and acquisitions (M&A), venture capital deals, private equity investments, public offerings, liquidity events, and significant personnel changes in the corporate world. It’s targeted towards dealmakers and gives detailed insights with a point of view. It has a daily cadence and is free, which is almost unfair for the quality (Axios monetizes elsewhere).

This newsletter is very broad; it is a combination of VC + PE + M&A + the politics of business rather than just pure M&A. Detail is not compromised; you will be left with up-to-date, in-depth knowledge of recent significant financial transactions and market movements. Making it an ideal read for anyone interested in the latest developments in the financial and corporate sectors.

2. Evernomic Confidential

Okay, you caught me. Yes, I put my own newsletter at number two. But I’d be a hypocrite to write about what makes a great M&A newsletter and then leave out the one I’m pouring everything into. Evernomic Confidential is a publication in which we analyze deal flow and market trends we’re seeing for independent buyers, search fund operators, and anyone seriously considering buying or selling a company. Run by myself and Arian Adeli (the founder).

What we aim to do is fundamentally different from any other M&A newsletter. We take a company currently on the market and analyze it the way a buy-side advisor would: the financials and what the seller is or isn’t showing you, the risks we’d want to pressure test, where we see upside, how it holds up against competitors, and the industry context you need to make a decision. We are not running broker advertisements; every deal is anonymized. We focus on software, saas, AI, and media companies (the digital business realm).

Evernomic Confidential

Deal flow analysis and market trends for people buying and selling companies.

By Arian Adeli

3. SMB Deal Hunter

SMB Deal Hunter by Helen Guo is actually the first M&A newsletter I came across and subscribed to. It is heavy on the buyer success stories with tactical case studies. She leans into creative financing (seller notes, earnouts) and the how to actually close it, rather than just describing a listing.

With 200,000-plus subscribers, it’s the biggest name in the search-fund and SMB-acquisition niche for good reason. It’s free, with a paid Pro tier if you want more. SMB Deal Hunter is entrepreneurship-through-acquisition territory, not institutional M&A. Making it ideal for those actually looking to close a deal rather than just admiring. The focus is on off-market businesses profiled before they hit the public marketplaces, adding an extra layer of value.

4. Reuters

Reuters is a news section, not a curated email like the others in this list, however it has earned a spot because it can be stacked on-top of an analysis centered newsletter where Reuters gives you wire-service speed and neutrality, usually first to the announcement, anywhere in the world, across every sector. There’s only the facts, which is the exact opposite of an opinion-led newsletter and a useful opposite to have in your stack. It covers significant business transactions, market deals, and financial news that impact the stock market and business landscape.

5. PE Hub

PE Hub is the professional’s tab, specifically catered towards professionals and stakeholders in the private equity industry. It gives you exclusive coverage and executive interviews you won’t get off the wire. It’s organised into sector verticals (healthcare, tech, energy and so on), so you can go deep in whatever niche you care about, behind the pen is the PEI Group meaning you are getting institutional credibility. It runs on a freemium model, and the premium material sits behind a paywall. You can expect private equity deal news, exits and fundraises.

And guess what? PE Hub was originally created by Dan Primack, the same Dan Primack behind my number one, back in his Thomson Reuters days.

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6. The Daily Pitch (PitchBook)

The Daily Pitch by PitchBook news team is for the reader who wants the data under the story. PitchBook is a Morningstar company making the edge is obvious: it’s backed by their proprietary dataset, so you get charts and figures the other newsletters simply can’t cite. It covers VC, PE and M&A with that data spine running under every story.

Yes, it’s partly a free taste of a famously expensive platform, and sometimes it reads like top-of-funnel for the terminal; however, it’s still genuinely useful, and free is free. I’d pair it with an opinion newsletter similar to Reuters.

7. Exec Sum

Exec Sum is the proof that finance and humor scale. It comes from Litquidity: “Lit”, the pseudonymous personality behind a whole finance-meme empire, and it’s the “straight news, with a wink” arm of that brand. 300,000-plus readers get a fast, skimmable daily wrap of the news from Wall Street to Silicon Valley, memes included. It provides a concise summary of significant financial and business news, while being personality-led.

However, Exec Sum is a daily skim rather than a deep M&A analysis. But for staying current without it feeling like homework, it’s hard to beat. It is completely free and best for finance people who want the news and the memes.

To wrap it up

A couple of words on how I picked these. This isn’t a hard ranking and isn’t as comprehensive as it could be. But they are the ones I actually open and read, and I have chosen these specifically to show the range. From the breaking-news wire to the meme-laced daily skim to the slow, deep analysis.

Put them against the six things I said make a good one and a pattern shows up: the best newsletters give you a point of view, an edge you can’t get elsewhere, and a writer you’ve got reason to trust. Stack two or three that do different jobs and you’ll know more than most people in the room.

And yes, number two is still mine. If you’re an independent buyer, search fund operator, or someone who’s interested in buying or selling companies, you know who to go to.

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Either way, go subscribe to a few of these. The genre’s in a good place in 2026, and your inbox could do a lot worse.

Have a blessed day.

There’s this paradox with Main Street deals where if the deal is for sale, there’s almost certainly something wrong with it. It’s rare to see one with solid numbers that’s not on the brink of extinction.

Today I’m reviewing a monetization platform that lets creators charge for access to Telegram, Discord, and WhatsApp communities. It handles paywalls, sign-ups, renewals, and removals when someone stops paying, with an affiliate program built in to help creators grow. It takes 15% of what creators earn through it, or 4% if they pay $99 a month.

• TTM revenue $730k, growing 42% year on year

• TTM profit (SDE) $710k, 97% margin

• Asking $4.1M, 5.8x profit, 5.6x revenue

• 500+ creators onboarded, churn 1 to 3%

• Solo founder, bootstrapped, founded January 2023

• Runs on Stripe with tiered take-rate model

About a decade ago, I tried my luck selling trading signals on Telegram, and a tool like this would have come in handy. No doubt, much of the user base consists of communities in that exact niche.

If you’re new here, we analyze the deal flow and market trends we come across. Looking to buy or sell? Reply to this piece.

In short

• The revenue growth comes from existing creators getting bigger, not new ones signing up: traffic’s flat while revenue climbs. So the whole deal depends on who those creators are and how concentrated the money is. That list is the first thing I’d want.

• The margin isn’t a software margin. The platform takes a cut on top of creator revenue, and the revenue is lower-quality than the number suggests.

• The volume is probably from high-risk, high-chargeback categories: trading signals, crypto, and courses. It all runs through a single processor, so the biggest risk is Stripe deciding it’s too risky and cutting it off.

• Whop ($142M) and Stan ($35M) are the largest competitors. The opening aims to attract higher-caliber communities to the platform by adding bundles, gifting, referral kickbacks, and the retention and growth tools that Substack and Patreon already use.

• I would not do the deal at this price ($4.1M). Comps are trading between 2.2x and 3.4x SDE. It’s been listed for less than a month, the ask will drop, and if the creator list holds up, there’s a deal in the high two-millions with the seller carrying the risk.

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The seller claims there has been zero marketing: no ads, no content, nothing. I don’t buy that for a second. No one launches something in utter silence and reaches $730K in revenue. There may have been no paid marketing, or an initial marketing push may have given them the momentum that took them where they are today. The take-rate model means revenue compounds as the creators on it grow, even without a single new sign-up. And that’s why the first thing I’d want is a list of their current creators. That’s everything.

Revenue is up 42% YoY while the site’s traffic has been flat to slightly down all year. Flat traffic and rising revenue on a fixed customer base also point to existing creators getting bigger, not new ones showing up. That could be a massive green flag depending on how concentrated the cash cows are. If a handful of large communities drive most of the take, you’re buying those few relationships, and any one of them can leave, fade, or get deplatformed by Telegram (unlikely) or Meta and walk off with a chunk of the revenue. In that case, the single-digit logo churn could be sitting atop a more concerning revenue risk.

Paid Telegram, Discord, and WhatsApp communities lean hard toward a particular set of things: trading and crypto signals, betting tips, reselling, get-rich courses, and the high-risk, high-chargeback end of the internet. That’s less a guess about this specific tool and more the shape of the whole industry.

Whop, the largest competitor on the list, is described across industry coverage as a home for exactly those gray-market sellers. It de-risks the platform by simultaneously routing payments through multiple payment providers to keep authorizations up. This tool runs on Stripe. So if a meaningful share is high-chargeback, the single biggest threat is Stripe deciding the volume is too risky and cutting it off. That risk doesn’t show in a P&L.

Comps

Whop raised $200M in early 2026 at a $1.6 billion valuation and runs north of a billion dollars in annual GMV across roughly 28,000 active sellers. Sacra frames it as a marketplace and toolset for selling digital products, courses, memberships, and betting tips, and as the checkout and discovery layer for grey-market creator SKUs: sneaker bots, sports betting lines, day trading tips, crypto, trading cards, and social media clipping.

The second-largest competitor is Stan, enabling creators to sell downloads, courses, and bookings from a link-in-bio storefront. You can actually view their verified revenue data here.

Whop, which launched an App Store in June 2025, is also building Chat by Whop (aimed straight at Discord) and Livestreaming by Whop (aimed at Twitch). Whop is the Amazon (a marketplace that compounds through demand-side aggregation) to Stan’s Shopify, and it overtook Stan in 2025 for exactly that reason.

On multiples, I reviewed three other comparable deals, and they are asking between 2.2x and 3.4x SDE. 5.8x is definitely on the higher side. The more important issue is the multiple being applied to take-rate revenue, priced as if it were clean recurring software.

Opportunities I see

One obvious risk is that it’s an add-on to other platforms. If Telegram introduces paid communities tomorrow, you’ll almost certainly lose a chunk of your business if all you provide is a payment gateway. Now, it’s unlikely that WhatsApp, Discord, and Telegram would collectively introduce paid subscriptions, but counteracting this threat would be my first call to de-risk the business.

They already offer an affiliate program and a set of growth tools for creators, but I’d develop that further. I’d offer creators on the platform the option to bundle their subscriptions. I’d urge individual subscribers to gift free subscriptions to their friends to reduce churn at the subscriber level. I’d introduce a “recommendations” flow where creators can recommend other communities to their subscribers and earn a kickback.

You can take a page out of the books of other subscription-based platforms like Substack and Patreon, too. They’ve already done a lot of the heavy lifting to make subscriptions a reliable revenue stream for creators.

I wouldn’t double down on the high-risk niches, but if you do, introducing crypto payments for subscribers would certainly be in demand.

I’d focus on bringing higher-caliber communities onto the platform and using them as case studies to drive further growth. Advise.so is a good example, a community at the intersection of AI and marketing doing ~$25K MRR. The community itself is for sale, too. You can see its verified revenue and reach out here.

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Questions I’d ask

As mentioned before, the first thing I’d want to see is the list of creators and everything there is to know about them.

• What share of the take comes from the top ten communities? Who are they?

• What’s actually sold through the platform, broken down by vertical?

• Have you shared any success stories publicly?

• What’s the split between Telegram, WhatsApp, and Discord?

I’d also want to learn more about the payment infrastructure.

• Are creators on their own connected accounts, or is the platform the merchant of record?

• What do chargeback rates and Stripe’s risk standing look like?

The fact that there have been no active marketing efforts so far is both impressive and an opportunity, but it raises the question of why. I can think of countless strategies, from using flagship creators as success stories to mass UGC campaigns and paid ads.

• Did the seller try running ads before, and the results were negligible?

• If so, was the CAC too high to continue? Did organic not see much traction?

Lastly, the founder is the one person handling product, support, and the integrations that break every time Telegram or WhatsApp ships a change, so what does replacing that work cost, and will they stay through a transition?

So would I do the deal?

That entirely depends on the answers to the questions above, especially regarding the creators. In either case, I wouldn’t do the deal at $4.1M. At the time of writing, they’ve been listed for less than a month. They’ll almost certainly be dropping the ask, and the multiple is far too high right now.

One thing I like about this deal is that it’s not vibe-coded garbage. The website is neatly designed, with a calculator to show how much you could earn as a creator, social proof, and everything else that makes for a high-converting landing page. You wouldn’t need to spend time optimizing the brand and could focus on growth immediately.

That said, the risks are too high unless you have the network to amplify this. If the answers hold up, I’d be in the high two millions, with a sizable piece tied to an earnout on revenue over the next year. I’d also consider heavy seller-financing. In either case, given the risk profile, I’d want the founder to share the risk during the initial phases.

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Evernomic Confidential only covers third-party deals we come across. We never write about anything Evernomic represents or holds a financial interest in. This analysis is for informational purposes only. It isn’t investment, financial, or legal advice, and we can be wrong. Do your own diligence before acting on any deal.

Friends,

I recently spent a good amount of time deciding where to host this publication. It sounds like a small decision but if you run media companies for a living, you know that platform choice shapes everything downstream: your economics, your distribution, your relationship with your audience, and ultimately whether you’re building leverage.

I landed on Substack. And because I tend to overthink things, that decision turned into a full-blown analysis of the company, its business model, where it’s headed, and how to best position yourself. So instead of keeping all of that thinking to myself, I figured I’d share it.

In this letter (est. 3800 words)

• Substack’s 10% model looks simple but $220M in funding and a $1.1B valuation tell a different story. Where is the money going?

• They’re not building a newsletter platform anymore. They’re building an email-first social media

• What Substack gets right: badges, gamification, and the ecosystem dynamics most creators overlook

• Why multiple touchpoints matter more than email alone, and how paid subscription psychology actually works

• The social media lock-in playbook and why migration is harder than it sounds

• What Substack gets wrong and what they should fix

• Untapped revenue avenues that could change the Substack’s economics

• Would I invest in Substack?

The first thing you notice when you dig into Substack’s numbers is how deceptively simple the business looks on paper. They take 10% of what creators earn through paid subscriptions. That’s it. No SaaS fees, no advertising revenue (potentially changing), no enterprise contracts. If writers make money, Substack makes money. If they don’t, Substack doesn’t either.

The alignment sounds elegant. And in many ways it is. Compare Substack’s 10% to YouTube taking 45% or app stores taking 30%, and the deal looks generous. Creators know this, which is why the platform has attracted some serious editorial talent.

Substack raised $100 million in July 2025 at a $1.1 billion valuation. They’ve raised $220 million in total. Their estimated annualized revenue is around $45 million, based on roughly $450 million in gross writer revenue flowing through the platform. So, where is all this money going?

Email, first.

Substack is not building a newsletter platform. Not anymore. They’re building an email-first social media company.

That distinction matters enormously. A newsletter platform is infrastructure. You write, it sends. The value is in reliability and deliverability. An email-first social media company is something entirely different. It’s a network where the content happens to arrive in your inbox but the engagement, the discovery, the community, and increasingly the consumption happens inside an app and a social feed.

Look at what Substack has built in the last three years.

• Notes, which functions like a Twitter alternative for long-form thinkers.

• An app that now drives more subscriptions than the recommendation engine (roughly 3 million per month from the app versus 2 million from recommendations).

• Chat features for community building.

• Podcast hosting.

• Video and streaming features.

• Substack TV is in development.

They’ve even started experimenting with advertising, something the founders resisted for years.

They’re no longer competing with Beehiiv or Mailchimp or Ghost. They’re competing with Medium, Twitter, Spotify, and arguably Patreon, all at once. Substack is newsletters, blogging, microblogging, podcasting, live streaming, and a payment layer, bundled into a single platform with a social graph on top.

The $100 million makes more sense now. You don’t build a social media platform on the revenue from a 10% take rate alone. You invest ahead of the growth, betting that the social network becomes sticky enough to justify the spend.

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What Substack gets right

And it’s more interesting than most people give them credit for.

When you join as a creator, Substack has already spent a great deal of time and resource doing the tough thinking for you.

One of my favorite features is auto-paywalling older posts after a certain period of time. This essentially means: if you’re a subscriber, indulge away. If not, pay the price for being late.

5 years ago, this was a strategy only a top-tier media company could implement.

The paid subscription badge is another small feature that reveals sophisticated thinking about the platform.

Substack adds a gray badge next to the names of people who subscribe to paid newsletters. It’s a status signal, similar to the blue checkmark on X. For creators, it’s a visible differentiator. For readers, it’s an incentive to pay for at least one newsletter, even if it’s not one they particularly need, just to get the badge.

I actually read my paid subscriptions but, heck, I’d pay just to get the badge.

Gamification

If Substack introduces tiered badges (different colors for different levels of paid subscriptions), they create a gamification layer that could meaningfully drive paid subscription volume across the platform. Imagine a badge that requires subscribing to 10 paid newsletters. For a serious creator who wants algorithmic boost and credibility, that math could make sense. And Substack could offer algorithmic priority to users with higher-tier badges, creating a flywheel where paying more gets you seen more, which incentivizes paying more.

They haven’t done this yet. But the infrastructure is there.

The economics of this get interesting quickly. Say Substack introduces a badge tier that requires 10 paid subscriptions. At an average of $10/month per newsletter, that’s $100/month per user, of which Substack takes 10%. Scale that across thousands of users who want the visibility that comes with the badge and you’re looking at a meaningful revenue accelerator that costs Substack nothing to deliver. Push it further: a top-tier badge requiring, say, 100 paid subscriptions would cost a user $1,000/month. That sounds extreme until you consider that for a serious creator trying to build reach, algorithmic priority could be worth every dollar if it translates to subscriber growth.

And this is where it gets delicate. If Substack ties algorithmic visibility to how much you spend on the platform, they create a powerful flywheel: spend more, get seen more, grow faster, earn more, spend more. But they also risk turning into a platform where reach is a function of budget rather than quality. The rich get richer, literally.

Every platform deals with some version of this (paid ads on Instagram, promoted posts on X, boosted content on LinkedIn) but Substack has built its brand on the promise that good writing wins. Introducing a system where spending power influences visibility would be a direct tension with that founding principle.

Though in fairness, of all the platforms, such an approach is the most acceptable one. It is pay-to-play to some degree but at least independent creators are getting paid for it, not just the platform.

The politics of this matter. Substack’s core audience is independent writers who chose the platform specifically because it felt like a level playing field compared to algorithm-driven social media. If the badge system starts to feel like solely a pay-to-play mechanism, the backlash from that community could be significant, even if the underlying economics make perfect sense. These are the kinds of decisions that define what a platform actually stands for versus what it says it stands for.

There’s a softer effect too that’s harder to measure but probably just as important. When someone browsing Substack sees that a large number of people in their feed have paid badges, it normalizes paying for content. It shifts the psychology from “why would I pay for a newsletter when so much is free” to “everyone here seems to be paying for things, maybe I should too.” That kind of social proof is incredibly powerful. It creates a culture of paying on the platform that benefits every creator, not just the ones gaming the badge system.

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The ecosystem dynamics are also worth understanding.

Substack is designed so that when you bring an audience to the platform, those people become Substack users, not just your subscribers. Your emails are Substack-branded. There’s a button to read in the app. The design is standardized. Some creators find this frustrating because it feels like Substack is stealing their audience, converting their readers into platform users who then discover competing publications.

But this dynamic actually serves independent media well, especially at the extremes. For the biggest names, the Substack leaderboard and discovery features provide credibility and exposure that’s worth the tradeoff. Being in the top 10 on Substack is a form of prestige that compounds as the platform grows. It’s almost like an angel investment: you bring your audience, the platform grows, your position on the leaderboard becomes more valuable. If Substack doubles in size, the top 10 spot doubles in reach.

For the smallest creators, the dynamic is even more favorable. When a major VC firm or a well-known media company joins Substack, they bring thousands of relevant readers onto the platform. Those readers then discover new voices through recommendations, Notes, and the app. The big names are doing free customer acquisition for the platform, and the small creators benefit from that influx. It’s a system that ensures new voices can emerge, while incentivizing incumbents to keep earning their position through quality rather than just riding on existing distribution.

Touchpoints

The most important thing Substack provides, and the thing that’s hardest to replicate elsewhere, is multiple touchpoints with the same person.

This matters most for content that isn’t standardized. Let me explain what I mean.

I run another newsletter where I feature a curated list of interesting websites every week. My subscribers know exactly what to expect every time they open my email. The format is standardized. Even if one week’s picks aren’t interesting to them, they’ll open it next week because the format itself is reliable. Email alone works fine for this kind of content because the open rate stays consistent.

But if you run a publication where every piece is different, the odds of any single piece being relevant to every subscriber are lower.

This is where email as your only communication channel becomes dangerous. If someone doesn’t open three emails in a row because the topics didn’t resonate, Gmail starts pushing you to promotions. Then spam. Then you’ve lost them entirely. And no matter how much you talk about “owning your audience,” you’re still at the mercy of email service providers. Your emails reaching people depends on Gmail, Yahoo, and Outlook deciding they should.

Substack solves this problem structurally. If someone misses the email, they might see the piece in the app. If they miss the app notification, they might see your Note about it. If they’re a paid subscriber, they have a recurring charge on their credit card reminding them you exist. That’s three or four touchpoints instead of one.

And the credit card bill is an underrated one. Every month, a paid subscriber sees a line item on their statement for your publication. It’s not a notification they can swipe away or an email they can archive without reading. It’s a financial commitment staring back at them, and it triggers a question: “Am I still getting value from this?” More often than not, the answer is yes, or at least “I might miss something if I cancel.”

That recurring charge keeps your publication in someone’s conscious consideration in a way that no email or push notification can replicate. For non-standardized content where not every piece will resonate with every reader, that repeated exposure is the difference between building a loyal audience and slowly losing people to inbox obscurity.

This is precisely why legacy media has (almost) exclusively moved to paid content. At the scale of brands like FT and NY Times, advertising is actually more profitable. But paid subscribers have equity value.

Psychology

The psychology of paid subscriptions on Substack is different from what most people assume.

Creators often think of paid newsletters like SaaS. You need to deliver consistent value every week to justify the recurring charge. If a subscriber doesn’t feel they’re getting their money’s worth every month, they’ll cancel.

That’s not how it actually works. The more likely behavior is that someone sees a specific piece they really want to read. Maybe it’s a deep dive on a topic they care about. They think: “I’d pay $10 to read this one piece.” So they subscribe. They don’t particularly care about what comes next that week or month. They wanted that one thing.

Then, as long as one or two more pieces over the following months are relevant to them, they keep the subscription. Not because every piece justifies the cost, but because the off-chance of missing something valuable outweighs the $10 per month. For serious readers, the subscription is almost a commitment device. It’s a way of saying: “I want to be the kind of person who reads this.”

This is why paid subscriptions on Substack function as a quality filter. The people who pay are the ones most likely to actually read. They’re your real audience. The free subscribers are your reach, your top of funnel. But the paid subscribers are the ones who will open every email, read every piece, and remember your name. If relationship building and credibility are your goals, those are the people who matter.

And about that 10% fee. It seems high until you calculate your cost per subscriber acquisition on any other platform. If you’re running Facebook ads to drive newsletter subscribers, you’re paying $2-4 per free subscriber. If your free-to-paid conversion rate is 5%, you’re spending $40-80 to acquire a single paid subscriber. Substack’s 10% on a $10/month subscriber over their lifetime is dramatically cheaper than paid acquisition through any other channel. The 10% isn’t a tax. It’s a distribution cost. And for most creators, it’s the cheapest distribution they’ll ever find.

Lock-in

Now, here’s where the social media pivot becomes strategically important. The reason Substack is building a social network isn’t just about growth. It’s also about adding enough value to lock-in creators.

A pure newsletter platform has almost almost no switching costs.

Migration is straightforward. Substack uses Stripe. You export your list. You ask Substack to disconnect your Stripe account. You connect it to your new platform. Paid subscribers don’t need to re-enter their payment details. It works.

But whether this makes strategic sense is a separate question.

If you’ve been on Substack for any length of time, part of your distribution is the platform itself. Notes, recommendations, the app, podcasts, video, the leaderboard. When you leave, you don’t take any of that with you. You take the email list and the payment relationships, but the distribution layer stays behind. And if that distribution layer was responsible for 20, 30, 40% of your subscriber growth, you’ve just cut off a significant growth channel with no replacement.

The creators who should stay on Substack are the ones benefiting from the network. And the ones benefiting from the network have the least reason to leave. This is, by design, a very effective retention mechanism.

This is the playbook every successful platform follows. Start with utility, build habit, add social, create lock-in. Facebook started with profiles, added the feed, became infrastructure. Twitter started with microblogging, added the timeline, became the public square. Substack started with newsletters, added Notes, and is trying to become the default platform for independent media.

Whether they succeed depends on something that’s genuinely uncertain: can a platform built around reading long-form content compete for attention with platforms built for quick consumption? Medium tried a version of this and it didn’t work. Tumblr tried it. The dynamics are different here because Substack has payments built in, which changes user behavior in fundamental ways. When you’re paying for content, you’re more intentional about consuming it. But the question is still open.

What Substack gets wrong

And some of it is puzzling.

The $50 one-time fee for connecting a custom domain is an odd choice. It’s not a meaningful revenue stream for a company processing hundreds of millions in gross transaction volume. The more likely rationale is that it’s a friction mechanism. If creators use the default substack.com URL, every share and every link is free advertising for the platform. A custom domain removes that. The $50 isn’t about the money. It’s about making you think twice before taking Substack’s name out of your URL. It’s a rational business decision disguised as an administrative fee, but it’s not something a confident, mainstream platform would need to do.

The algorithm also needs work. Right now, Notes rewards a fair amount of generic engagement bait. Posts like “Hey Substack, connect me with people in X industry” or “If you have less than 100 subscribers, introduce yourself here” routinely outperform substantive writing. That’s a familiar problem. Every social platform goes through this phase where community-building posts game the algorithm because they generate easy engagement. But Substack should be aggressive about fixing it.

Medium had its era precisely because every article on your feed felt like it was written for you. The recommendation engine was almost eerily good at surfacing relevant content. Substack needs that level of precision. If the Notes feed starts feeling like LinkedIn, full of performative engagement posts and hollow networking requests, the serious writers and readers who make the platform valuable will tune it out.

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So what’s the outlook?

There are small feature gaps that reveal how much room Substack has to improve the basics.

One I care about personally: you can’t add a profile picture to your newsletter emails. It sounds trivial but in a crowded inbox, a recognizable face or logo next to the sender name dramatically increases open rates. Substack doesn’t let you send from a custom email address (understandable given the complexity), but even with the default user@substack.com address, this should be solvable.

I actually published a guide a few years ago on a workaround that went viral. It involved setting your Substack to receive email replies from everyone, then adding your Substack email as a Gmail alias, which would inherit your Gmail profile picture. It was hacky but it worked.

Substack appears to have since closed that loophole by limiting forwarding to direct replies only. The fact that a workaround like that went viral tells you something about the demand. Creators want their emails to feel like theirs, not like generic Substack-branded messages. A native solution for this would be a small feature with outsized impact.

There are also signs that Substack has quiet arrangements with top creators that aren’t available to everyone.

Pirate Wires, for instance, has a custom website that integrates seamlessly with their Substack publication in ways that suggest they’ve been given API access that isn’t publicly documented.

It’s possible there’s a creative workaround involved, but I doubt it.

And honestly, I don’t have a problem with Substack giving special access to high-value creators. Every platform does this. What I’d like to see is transparency about it. If API access is available upon request for publications that meet certain criteria, say so publicly. Define the criteria. Let ambitious creators know that if they commit to building seriously on the platform, they’ll get serious tools in return.

Right now it feels like a backroom deal to me. Making it a visible path would attract more serious media brands to the platform and give people a reason to go all in on Substack rather than hedging with a self-hosted setup on the side.

New avenues

Overall, Substack has more strategic options than people realize. Right now, nearly all of their revenue comes from the 10% take rate. But let’s look at what they could do…

A native ad network for newsletters. Brands paying to place ads inside newsletters, with Substack taking a cut. They’ve started piloting this and the infrastructure is being built.

Paid recommendations between newsletters. Substack could introduce a version where creators pay to be recommended by other creators, with Substack facilitating the transaction and taking a percentage.

Native advertising within the app and Notes feed. This is the standard social media monetization playbook. Promoted posts, sponsored Notes, brand placements in the discovery feed. Substack has resisted this, but the infrastructure for it exists the moment they decide to flip the switch.

A premium Substack subscription. Similar to what X did with X Business or what Meta has explored, brands could pay Substack directly for better analytics, enhanced customization, algorithmic priority, or advanced features. The precedent is established. Every major social platform has moved toward direct platform subscriptions and Substack could follow.

They can’t adopt all of these overnight, partly because the founders have built the brand on being ad-free and creator-first. There’s politics to it but the options exist. And $100 million in fresh capital gives them runway to experiment.

The fact is, we’re still very early. You can feel it when you look at the platform closely. Substack is still figuring out what it is, and that’s actually an argument for being on the platform now rather than later. The writers who establish themselves during this experimental phase will have the strongest positions when the platform matures.

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Would I invest in Substack?

At the current valuation, it’s a bet on the social media pivot working. If Substack successfully transitions from a newsletter platform to an email-first social network for independent media, the 24x revenue multiple could look cheap in hindsight. The flywheel of writers attracting readers attracting more writers, amplified by a social layer that creates genuine lock-in, could compound into something very large.

But the risks are there. Creator concentration, competition from other creator tools, the unproven nature of a long-form social network, and the fundamental tension between creator portability and platform lock-in. Substack’s greatest strength (letting creators own everything) is also its greatest vulnerability (creators can leave whenever they want).

If I were writing the check, I’d want to see the creator retention numbers at the top tier, the revenue concentration data, and a clearer monetization roadmap beyond the 10% take rate, and how thought-through the dynamics of such a future are.

What I can say with confidence is that, as someone who operates media companies for a living, I chose to publish here. Not because Substack is perfect, but because the dynamics of the platform, the multiple touchpoints, the social layer, the paid subscription mechanics, the quality of the audience, align with what I’m trying to build better than the alternatives.

Welcome to Letters. There’s a lot more to come if you’re interested in the media industry.

Arian

When I moved to the Netherlands a few years ago, I had a pretty basic problem: I couldn’t read the news. Not because I didn’t care, but because it was all in Dutch. And the English-language alternatives were just mass translated pieces with no editorial voice.

So I started Groningen Mail (now Dutch Brief). It wasn’t a company. It wasn’t even really a plan. I liked news, I always wanted to work in media, and I figured if I was struggling to keep up with local news, other internationals probably were too.

The rules were simple: one article per day, free tools only, and write what we’d genuinely want to know.

Starting with nothing (on purpose)

We launched on Substack because it was free. It didn’t even have any of the social and distribution features it has today. Email sending was just free. We made an Instagram page, and that was the only channel we promoted on. No TikTok, no YouTube, no LinkedIn. Just Instagram, and a deliberate decision not to stretch beyond what we could actually manage.

For distribution, we went where the people already were. Facebook groups are surprisingly active in the Netherlands, especially among students and internationals. But we didn’t just drop links. We actively participated in these communities, answered questions, shared useful things. We ended up with top contributor badges in most of the groups we were active in. That mattered more than any post we ever shared about ourselves.

We also made one key partnership early on that gave us access to a WhatsApp group with about 800 members. We still use it today to share our most important stories and drive traffic back to the site.

None of this cost money. It cost attention.

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Community first

One of the most counterintuitive decisions we made was accepting student contributors. On the surface, it looks like an attempt to get free labor. It was actually the opposite. Coordinating an article topic with a contributor, coaching them through the writing, editing the draft, formatting it, and publishing it took more effort than just writing the piece ourselves.

But that was the point. Contributors built portfolios they could use for their careers. Some were journalism or media students doing university projects in collaboration with us. We showed up at student stands, welcome weeks, university programs. And every one of those contributors became an ambassador for the brand. They told their friends. Their friends subscribed. Word of mouth became our most reliable acquisition channel.

It wasn’t just student stands or contributor programs. We organized BBQs, networking events, pizza stands, and even run clubs. We ran this community-first model from the very beginning, and it has never stopped working.

Scaling in steps

At some point, the audience outgrew Groningen, which is the largest city in the north of the Netherlands. More than that, I moved to The Hague, and several of our team members were planning moves to other Dutch cities too. It stopped making sense to cover just the north.

So we rebranded to Dutch Brief, went national, and started expanding content volume. First we added Saturday editions. Then we moved to two articles per day. Now we sometimes publish three. As for video content, we started with one or two Instagram Reels per week, then moved to daily short-form, then expanded to TikTok, then YouTube.

Every expansion was deliberate. We never launched a channel because we felt we should. We launched when we had the capacity to do it well.

The same applied to our publishing infrastructure. We started on Substack, moved to Beehiiv when we needed better newsletter tools and a nicer website, and eventually migrated to Ghost when we needed full control over our SEO, our theme, and our content architecture. Each move was driven by a limitation we’d hit, not by chasing features.

Modern tooling

Here’s the part that surprises people: the day-to-day content production of Dutch Brief is managed by one editor—Lisa Vinogradova, a phenomenal writer and editorial mind. One person handles more than 90% of the daily output.

That’s not a flex about working hard. It’s just what’s possible when you build your stack around modern tools. We use LLMs for research and editing. We use Perplexity, Claude, and ChatGPT as part of our content workflow. We use ElevenLabs for voiceovers on our short-form video. We built custom tooling to make content creation faster when off-the-shelf solutions couldn’t keep up with our pace.

It goes without saying that Lisa is a magician in her craft. Her attention to detail and the care she puts in this project is hard to replicate. We often challenge each other’s opinions and her presence can certainly be felt. However, we couldn’t do this without being technologically aware and proactive either.

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None of this replaces editorial judgment. Every piece still starts with a subjective call: what do we think is interesting? What would we want to know today? The tools make the execution faster. The taste stays human.

And on the technical side, we’ve treated the website like a product. We built a custom Ghost theme. We implemented SEO best practices from the ground up. We have even experimented with every idea that made sense in the moment, like maintaining an llms.txt file. Funny enough, ChatGPT is one of our top three traffic referrers alongside Instagram and Google.

How we monetize

We were deliberately slow on monetization, and I don’t regret it. I never wanted to beg for sponsorships, and our early outbound experiments in that direction went nowhere anyway.

Instead, we built a native product: a mobile app for finding housing in the Netherlands. We put that as our main sponsor on the outlet and used our own traffic to drive users to something we’d built ourselves and believed in.

Now, at our current scale, inbound sponsorship interest has picked up. But we’re selective. We don’t partner with anyone just to make a quick buck. Partner selection is exclusive because our readers trust us, and that trust is the product.

At the end of the day, this has truly been a passion project from the start.

The revenue question matters now more than it used to, though. We want to expand the team. We want to bring more humans into the operation. We’d love to replace the AI voiceovers with a real voice actor. We want to produce long-form video for YouTube, not just repurposed short-form clips. All of that requires capital, and we’re working on making the economics support it.

20% of our readers aren’t even in the Netherlands

This is the part that changed how I think about what we’re building. Over 20% of Dutch Brief’s readership is based outside the Netherlands. People in Germany, Belgium, the UK, across Europe and beyond are reading us regularly.

At first that felt like an anomaly. But it actually points to something else: there’s an appetite across Europe for accessible, English-language coverage of individual countries. Whether it’s someone with business interests in the Netherlands, a family member who moved there, or just someone who wants to understand European politics beyond the Brussels bubble, the demand exists.

Most national news in Europe is locked behind language barriers. If you want to follow what’s happening in the Netherlands, Germany, or France and you don’t speak the language, your options are limited to whatever international outlets decide to cover. Which usually means you only hear about a country when something dramatic happens.

English-language national news fills that gap. And the model we’ve built at Dutch Brief could work for any European country with a large international community or cross-border relevance. We didn’t set out to prove that thesis, but our own readership data is making the case for us.

What I’d tell another founder

Start with distribution, not product. We didn’t have a website worth looking at for a long time, but we had an audience before we had infrastructure. That order matters.

Be community-driven in a way that actually costs you something. Contributors, university partnerships, showing up at events. None of that scales easily, and that’s exactly why it works.

Don’t expand channels until you can do them well. One good Instagram account beats five mediocre social profiles.

Use modern tools aggressively, but keep the editorial instinct human. Tools make you faster. They don’t make you interesting.

And don’t chase monetization before you’ve earned trust. The sponsors will come when the audience is there.

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I’ve used all three of these platforms. Not briefly, not as a test. I run publications on each of them right now and have for a while. I was recently looking for an in-depth comparison online and honestly couldn’t find one that wasn’t surface level or written by someone who tried each platform for any longer than a week. So here’s mine.

This isn’t a feature-by-feature breakdown. It’s what I’ve actually experienced with each of these platforms over the past few years.

Substack

Substack was the first platform I used. The social features are genuinely good and if your content catches fire, the growth potential is higher than anything beehiiv or Ghost can offer. The problem is that’s a big “if.” It works like any social platform. Post consistently, engage with others, and your odds go up. But engagement farming is a growing problem like any other social platform. More people are starting to treat it like a second Twitter.

I constantly see posts of “Hey Substack, connect me with people under 1,000 subscribers”, knowing damn well they won’t read anyone else’s content.

What Substack does better than anyone is put content in front of readers who are already in a paying mindset. Their discovery engine and social layer create a network effect that the other two platforms simply don’t have. If you write something great on beehiiv, it goes to your list. If you write something great on Substack, it could find its way to thousands of people who’ve never heard of you.

Monetization

Monetization on Substack is more limited than the other two in terms of channels. They take a 10% cut on paid subscriptions, which sounds steep but I actually don’t think it’s unreasonable when you consider they handle email sending for free for everyone. That’s expensive infrastructure and someone has to pay for it. I’ve heard they’re experimenting with an ad network similar to beehiiv, which could change the equation significantly if it materializes.

Here’s my take though: the conversions on Substack are fundamentally different and better. People on Substack are more inclined to pay. We’ve been in the market recently looking at Substacks to potentially acquire and the numbers are surprising. One guy was making $400K ARR charging $60/month, with basically no systems or processes in place. Just writing his thoughts whenever he felt like it. That kind of thing doesn’t really happen on other platforms. Survivorship bias, granted. But the point stands.

The reason is that paid content subscriptions don’t work like SaaS. A lot of people convert because they found one article they really wanted to read and thought “I don’t mind paying 20 bucks for this.” Others subscribe as a way of committing to content they enjoy. Unless your newsletter is consistently delivering something actionable, most of those subscribers won’t stick around forever. But the initial conversion is easier on Substack than anywhere else.

So the 10% fee looks different depending on your situation. If you already have strong distribution and can drive paid conversions on your own, 10% is indeed a cost. But if Substack’s ecosystem is the reason people are finding and paying for your content in the first place, it’s more like a distribution fee. And a reasonable one at that.

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Branding

My biggest frustration with Substack is that it’s not a platform for building a strong media brand. It’s a platform for publishing content with minimal friction and putting it in front of readers. Every Substack looks the same. You can’t even add a profile picture to your emails so they stand out in someone’s inbox. And because readers tend to subscribe to a lot of newsletters on Substack, even when they open your email, the odds of them actually reading it carefully are lower.

Believe me, I’ve tried to find a work around. I even found a loop hole to add profile pictures to your emails on Substack through email aliases and wrote a popular guide on it, but it no longer works.

This is a strategic issue if you’re thinking long term. A media brand is more than content. It’s how the content is packaged, how it feels to interact with, how recognizable it is across channels. Substack collapses all of that into a standardized template. That works fine for personal writers who are the brand themselves, but if you’re building something bigger than your own name, it becomes a limitation pretty quickly.

Especially given how easy it is these days to produce content, branding matters more than ever. People need to remember who you are and why they should care. Substack currently provides a killer social platform: get seen and own your audience. But it’s arguably not for serious media brands.

Some of these are easy fixes. But I’m not too hopeful because Substack has an incentive to keep people inside their own app. They can’t afford to offer full customization. That said, if someone at Substack reads this: adding an API, enabling custom sending domains, and giving publishers more control would go a long way. Those features are a necessity at this point. We publish content focused on startups and venture capital, and Substack’s audience is highly relevant to that. If I could configure a custom sending domain or use their API, I probably would have chosen Substack over Ghost or beehiiv when we launched our company newsletter, even with weaker monetization options.

Use Substack if you want to get your content out there without worrying about much beyond publishing.

beehiiv

beehiiv is my favorite of the three. I’m on their max plan with multiple newsletters running on the platform. The growth features are solid if you’re thoughtful about how you use them. Recommending random newsletters to your subscribers won’t drive quality growth, but picking the right ones through their recommendation network actually works.

What separates beehiiv from the other two is that it feels like it was built by people who actually run newsletters. The feature set makes sense for operators. Things like Sparkloop integration, a proper API, segmentation tools, and a referral program that works out of the box. On Ghost and Substack, I kept running into walls when I wanted to do things that felt basic for a newsletter business. On beehiiv, most of those things just work.

Ad network

What beehiiv offers that no other platform does is the ability to monetize from day one with just a handful of subscribers. Their ad network is a game changer.

To give you some numbers: you’re looking at roughly $1.50 to $2 CPC and around $8 CPM on average, with higher offers coming through occasionally. Those payouts are considerably lower than what you’d earn negotiating sponsors directly. A self-sold sponsorship in a decent niche could easily bring in 2 to 5x that. But here’s the thing: selling your own ads requires an audience large enough to attract sponsors, time to manage those relationships, and consistency in your send schedule. beehiiv’s ad network removes all of that friction and means you never have to send an email that generates $0 in revenue.

They used to send ad opportunities every Sunday within a specific booking window, which was fine but a bit rigid. Just recently they shipped the ability to insert ads on demand, which makes the whole thing much more flexible and means you can match ads to relevant content more naturally.

If you’re thinking about building a media business, the math here is worth thinking about carefully. beehiiv’s ad network probably isn’t your long-term primary revenue source. But it’s an incredible starting point. It generates revenue while you’re growing to the point where direct sponsorships make sense, and it fills the gaps on weeks when you don’t have a direct deal lined up.

API

Their API is really powerful and this is honestly what makes beehiiv work for more advanced setups. You can build a fully custom front end and handle email sending through beehiiv’s infrastructure. That’s exactly what we’re doing now. Your readers see your website, your brand, your design. But behind the scenes, beehiiv handles the email operations, growth tools, and monetization. It’s the best of both worlds if you’re willing to invest in a custom site.

beehiiv also integrates with platforms like Sparkloop for paid referrals, which I couldn’t easily set up on Ghost or Substack. These integrations matter more than they sound. When you’re trying to grow a newsletter, every additional distribution channel is worth something.

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The team behind it

I want to mention their team specifically because it also matters when you’re building on someone else’s platform. When we acquired a newsletter that was already on beehiiv, their support team helped us with the entire transition in under 24 hours. That’s not normal. More recently, I wrote them a support ticket asking about improving deliverability and open rates. Within 12 hours they came back with a 758-word response, packed with specific suggestions and links, clearly written for my situation. Not a template, not AI-generated, someone on their team actually sat down and thought through my questions. In general, whenever I have a question about their ad network or run into a technical issue, they’re quick to respond. You can tell the team actually pays attention to their users and engages with them regularly.

They’ve also always engaged with any social posts I’ve seen that mention beehiiv. I wouldn’t be surprised if their team reads this article before Substack or Ghost.

What’s not great

A few things that still need work. The editor isn’t smooth, though they’ve said they’re focused on improving it. The website builder looks decent in concept but the output is slow and the SEO is poor. If your web presence matters to you, you’ll want to build a custom site and use beehiiv for the email side. And migrating paid subscribers away from beehiiv is more painful than it should be, which is worth knowing before you commit.

Use beehiiv if you’re building a media brand with advanced needs around growth, monetization, and integrations, but still don’t want to reinvent the wheel on everything.

Ghost

Ghost is actually incredible in a lot of ways. But it originally started out as a “simpler WordPress” and you can feel that in how it works. It’s not newsletter-first. The whole architecture is built around the web experience and email is bolted on, competently, but bolted on. Even something like custom sending domain configuration was confusing because they apparently send from a ghost.domain.com subdomain, which wasn’t clearly stated anywhere obvious. I spent time thinking they were sending from my root domain, which would be bad practice.

The SEO is excellent out of the box. The structured data, meta handling, and overall web performance are noticeably better than what beehiiv’s website builder produces. You can also customize the look of your site down to the pixel if you’re willing to dig into the theme layer. You need some technical ability for that, but with AI tools being what they are now, most people could manage it.

Ghost is built for a technical audience though. It’s open-source but it also just feels technical. Even something as simple as releasing major updates in a version format (Ghost v6, v5, etc.) seems unintuitive for the average user. I definitely do think this plays a role in their general adoption.

It also has certain features like the social web which means precisely nothing to most people, but it’s interesting if you take the time to understand it.

Double opt-in

Ghost is opinionated. More opinionated than I’d like. The most frustrating example: you can’t turn off double opt-in. They believe it’s the best practice for deliverability and they enforce it across the platform. I understand their reasoning and I respect it, but my platform shouldn’t make that decision for me. I can’t even customize the double opt-in email.

When we switched our company newsletter away from Ghost, our signup conversions jumped by at least 50%. And that’s with several anti-bot checks on the new site, so these are genuine signups with strong open rates. The double opt-in was just filtering out real people who missed or forgot about the confirmation email. Maybe you think that’s a small number, but we wouldn’t have known either way because Ghost doesn’t give you visibility into how many people start the signup process and never confirm.

In Ghost’s defense

Now, to be fair, their strictness does come with some upside. Ghost ensures very high deliverability and list quality. When we imported an email list into Dutch Brief, which runs on Ghost, they actually paused email sending until they could verify the list was legitimate. At first that was frustrating. But looking back, it’s the kind of thing that protects your sender reputation in ways you might not appreciate until something goes wrong.

If mass email growth isn’t your primary focus and you care more about maintaining a clean sender reputation, Ghost’s opinionated approach might actually work in your favor. It’s a trade-off. You give up control and flexibility, but you get a platform that actively prevents you from hurting your own deliverability. For some publishers, that’s exactly right.

Growth tools are limited

The growth features are limited compared to the other two. I couldn’t integrate with newsletter-focused tools like Sparkloop, the recommendation network is not as effective, and there’s not really a discovery mechanism if your brand doesn’t already have distribution figured out. Ghost basically assumes you’ll bring your own audience. If you can, great. If you can’t, you’re going to feel the absence of the growth infrastructure that beehiiv and Substack provide.

Paid subscriptions and the CMS

I haven’t tried paid subscriptions on Ghost but from what I’ve seen, it’s the best of both worlds mechanically. Smooth process and no 10% fee. That said, I still think you’d convert more paid subscribers on Substack than Ghost, making the commission worth it, unless your own distribution is already strong.

One more thing. Ghost is clearly built for technical people. The CMS feels limited unless you get creative with internal tags and theme configuration. For a platform that positions itself as a publishing tool, the content management side still has some catching up to do. There’s a saying around it that Ghost is as good as you are creative. You need to be comfortable to roll up your sleeves to customize the setup, or just accept their opinions.

Use Ghost if your distribution is already strong and you care about your web presence just as much as your emails.

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So what do we actually do

As I said, we have publications on all three of these platforms, and we’ll likely continue to do that. They each have their strengths and it’s good for us to be aware of what’s in the market. But I’ll tell you what we ended up doing for Letters by Evernomic, the newsletter that you’re currently reading.

When we launched our company newsletter at Evernomic, I chose Ghost because of the web experience, customization, and SEO. I wanted our landing page to be premium. But the limitations on growth tools and the strong opinions on things like double opt-in made it not worth the trade-off for a newsletter that needed to grow.

We ended up migrating the website to a custom Next.js deployment with Payload CMS and using beehiiv’s API for email sending. That gives us full control over how the site looks and performs, with the SEO and speed you’d expect from a modern web stack, while still getting access to beehiiv’s growth and monetization tools. It’s more work to set up, but for a media operation that takes both the web and email seriously, it’s the setup that made the most sense. We get. the best of both worlds, literally.

Dutch Brief stays on Ghost because it doesn’t need the same growth infrastructure. It has strong distribution through its social channels and the web experience Ghost provides is exactly what it needs. It’s also a local newsletter so the growth tools of Substack and beehiiv are not as effective since they’re good at pushing you in front of the whole world, not just a particular country.

Each platform has earned its place for a different reason for us.

All three of these platforms are actively improving and I’d expect each of them to address some of these gaps over time. beehiiv ships features faster than most startups I’ve seen, Substack is experimenting with new monetization channels including what sounds like an ad network, and Ghost continues to refine what’s already a really solid product. The competition between them is probably the best thing happening for independent publishers right now.

The reality is that no single platform does everything well yet. Picking the right one depends entirely on what you’re actually trying to build. And if you’re serious about building a media company, you might end up like me, using all three and stitching together the best parts of each.

You can learn a lot about a buyer by the questions they ask. The average buyer sends over a due diligence checklist they got from ChatGPT. P&L statements, churn rates, traffic sources. Those things matter but it’s table stakes. It tells you nothing about how seriously they’re evaluating the business or how well they understand what they’d actually be buying.

The best buyers ask different questions. They ask things that make you pause and force you to look at your own business from an angle you (maybe) hadn’t thought about. They’re trying to figure out whether this thing still works once they’re the ones running it.

I’ve been on the sell side of enough acquisitions across media properties, SaaS products, marketplaces, and communities to notice patterns. These are 50 questions that stood out. Not because they’re the most common, but because they actually mean something.

If you’re a buyer, asking the right questions shows you’re serious and that you actually understand the business. If you’re a seller, having answers to these ready before anyone asks shows you’re prepared. And prepared sellers close faster and at better terms.

Revenue quality

What percentage of revenue comes from your top 10 customers? If one account makes up 40% of revenue, you’re not really buying a business. You’re mostly buying a relationship with that customer.

For credit or token-based purchases, how many of those buyers actually come back and buy again? This is basically your repeat purchase rate for non-subscription revenue.

Was there a single month that skewed the annual numbers? What happened?

How long does your average customer stick around and what keeps them there?

Have any customers pre-paid annually? When do those renewals come up?

What’s the refund rate and has it changed in the last six months? Rising refunds usually show up before churn kills you.

How much of last month’s revenue came from marketing spend versus organic?

Is there seasonality in the business and what does it look like? This isn’t a red flag. An exam prep app will obviously spike around academic cycles. What matters is whether the seller understands the pattern and uses the off-season productively. Things like shipping features during quiet months, building partnerships, or planning campaigns for the next cycle. Seasonality with a strategy behind it is fine. Seasonality that catches the seller off guard is not.

Audience and engagement

What’s the open rate trend over the last twelve months? Not the average. The trend.

What’s the comment rate, and what’s the reply rate to those comments? This separates actual engagement from passive consumption. High views with no replies usually means people are scrolling, not reading.

How many subscribers have been on the list for more than a year and still open regularly?

Have you ever missed a publishing cadence? What happened to traffic and engagement when you did? If nobody notices when you skip a week, that’s a problem.

Has any single piece of content or event driven a disproportionate chunk of subscriber growth?

If you removed social media distribution entirely, what would traffic look like? A Substack newsletter has way higher platform dependency than one on Beehiiv or Ghost, and that distinction matters for what you’re actually acquiring.

What’s the unsubscribe spike after promotional emails versus regular content?

What’s your deliverability rate and have you had issues with spam filters or blacklists? A list of 100,000 subscribers means a lot less if 30% of sends land in spam.

Operations and dependencies

Can you share the last 30 days of support ticket volume? This tells you two things. How much operational load comes with the business, and that the buyer actually did their homework on which support tool you’re running.

How many hours per week does this business actually take? Be honest. It’s not as nice as you’d expect for a buyer to hear this business takes no input whatsoever.

What keeps breaking or falling behind that you haven’t had time to fix?

Which tools or platforms would break the business if they changed their terms tomorrow? Something built entirely on Shopify’s API or Meta’s ad platform carries a different risk than something with its own infrastructure. A lot of companies paid the price for this when X changed their API terms.

Is there anything that only you know how to do that’s not documented anywhere? Context is often the most valuable asset the team could transfer.

Who are the contractors or freelancers involved and which ones would be hard to replace?

What does the on-call or incident response process look like? Or does one not exist?

Walk me through a typical week operationally. Monday to Friday.

Product and technology

When was the last time you shipped something meaningful and what was it?

What’s the oldest part of the codebase and how often does it cause problems?

What’s in the backlog that customers keep asking for that you haven’t built?

Are there known bugs you’ve just chosen to live with? Why?

Do you have automated tests? What’s the coverage like?

How painful would it be to migrate off your current hosting or infrastructure? This is where most transitions get messy. Some buyers may want to take advantage of their own infrastructure to mitigate costs.

If a critical dependency pushed a breaking change tomorrow, how long would the fix take?

Growth and acquisition channels

What’s your customer acquisition cost by channel and which channel is getting more expensive?

Is there a channel or strategy you think would work but haven’t tried yet? Good for sizing upside but also for understanding why it hasn’t happened. Usually it’s time, not ideas.

How much of your growth is organic search and how exposed is that to an algorithm change?

Have you ever tried paid acquisition? What happened?

What’s the conversion rate from free to paid and has it moved in the last year?

Where do you think the easiest revenue gains are that you just haven’t gotten to?

Community and marketplaces

What’s the ratio of active contributors to lurkers?

How concentrated is activity among your top users? Does the community fall apart if five people leave?

What’s the supply-side retention rate after their first transaction?

How do buyers and sellers currently find each other outside your platform?

What’s the take rate and have you tested whether the market tolerates a higher one?

How much activity happens off-platform after the initial connection? This is the disintermediation question. If people can cut you out after the first transaction, the platform’s long-term value is shaky.

Who’s actually paying? The end user or someone else? In a community for marketers, for example, their employers might be subsidizing the membership. That completely changes who you’re selling to and how you retain them.

Competitive and market positioning

Who do you lose deals to most often and what reason do they give?

How long would it take a new entrant to get to where you are today?

What do you have that’s hard to copy? Data, relationships, brand, distribution? If the answer is nothing, that obviously tells you something too.

What’s changing in the market that worries you most?

When a customer leaves, where do they go? Do they ever come back?

Why are you selling? It’s the most obvious question on this list but it’s here because the answer is rarely simple. Burnout, a new opportunity, a partnership falling apart. The reason shapes everything from transition risk to how much post-sale involvement you can expect. A seller who’s exhausted will hand things off faster but might also be leaving behind deferred problems.

Not all of these apply to every deal. A SaaS acquisition is a completely different conversation than buying a newsletter. But the principle is the same. The questions worth asking are the ones that make the seller think before answering.

If you’re buying, use these as a starting point, not a script. If you’re selling, go through this list and see how many you can answer right now. The gaps tell you where your prep work is.

If you’ve ever looked at how media properties get valued and felt like the numbers didn’t add up, you’re not wrong. They often don’t. At least not if you’re only looking at the financial statements.

The spreadsheet stuff matters. But they’re not what separates a media company someone will pay a premium for from one that sits on the market for months. The difference lives in a set of less obvious factors that are harder to measure but far more predictive of long-term value.

This letter is about those factors.

Owned vs. rented attention

This is the single biggest divide in media valuation and most people still underweight it.

If your audience reaches you through a platform, an algorithm, a feed, or a recommendation engine, you don’t have an audience. You have traffic. Traffic can disappear overnight because someone else controls the dial. We’ve watched this happen repeatedly with publishers who built enormous reach on popular social media platforms, then watched it evaporate when algorithms shifted. Creators who had millions of views on one platform and couldn’t move a fraction of that audience anywhere else.

This is why we’re seeing every creator place a newsletter link in their bio. They own that audience.

Email subscribers, paying members, direct app installs are all fundamentally different assets. It’s not just more stable. It changes the entire economics of the business. You can price differently. You can launch new products into an audience that already trusts you. You can survive platform shifts that kill your competitors.

When someone is evaluating a media company, the ratio of owned to rented attention is one of the first things that should matter. A company doing $2 million in revenue with 80% of its distribution owned is a categorically different business than one doing $2 million with 80% of its distribution dependent on a platform it doesn’t control. The second one isn’t really worth $2 million in revenue. It’s worth whatever that revenue looks like after the next algorithm change.

The dependency question

Every media company has dependencies. The question is how deep they go and how hard they are to replace.

Some dependencies are operational: a specific CMS, a particular ad network, a tool in the workflow. These are annoying to replace but survivable. Other dependencies are existential: a single writer whose voice is the entire brand, a platform that delivers 90% of traffic, one advertiser that accounts for half of revenue.

The tricky part is that some existential dependencies are also what make a media company valuable in the first place. A publication built around a singular voice can command incredible loyalty and pricing power, but it’s also fragile in a way that a more institutional brand isn’t. That’s not a reason to avoid building around a strong voice. It’s a reason to be honest about what it means for the value of the business and to think deliberately about how to reduce that fragility over time without killing the thing that makes it work.

When you’re assessing a media property — whether you’re building it, buying it, or investing in it — map the dependencies. Not just what they are, but what happens if each one goes away. The companies that are worth the most are the ones where no single dependency can kill them.

Revenue composition

A dollar is not a dollar in media.

A dollar from a single advertising client who could leave next quarter is worth less than a dollar from a diversified set of sponsors. A dollar from sponsorship is worth less than a dollar from subscriptions, because subscriptions are more predictable and harder to lose. A dollar from subscriptions is also worth less than a dollar from a mix of subscriptions: content, paid community, events, B2B, and so on. The circle goes on.

Two newsletters can have the same number of paying subscribers and the same monthly revenue, but if one built its base through its own channels and the other got most of its growth through Substack’s discovery engine, those are not the same business. The first one owns its growth. The second one is renting it. If Substack tweaks how recommendations work or deprioritizes a niche, that revenue doesn’t have anywhere else to come from. That said, there’s a flip side. A newsletter that grows organically through platform discovery has very low acquisition costs, which makes it attractive to a different kind of buyer.

Most media companies know this intellectually but don’t act on it until they have to. They find one revenue stream that works and ride it until it stops working. By then, building the next stream is an emergency instead of a strategy.

The revenue composition also signals something deeper about the business: how many different ways it has found to be valuable to its audience. A media company with four revenue streams isn’t just more diversified, its audience trusts it in four different contexts. That’s a much stronger foundation than one built on a single transaction type, no matter how profitable that single stream is today.

Depth vs. breadth of attention

Reach is the metric everyone defaults to because it’s easy to measure. But reach alone tells you almost nothing about value.

A publication that reaches ten million people who spend nine seconds skimming a headline is not more valuable than one that reaches fifty thousand people who read every word and act on what they read. The second one can charge more per impression, convert at higher rates, launch products its audience will actually buy, and build the kind of trust that compounds over years.

The buyers we speak to care for some qualifiers that most skip fast. How often do people comment on your posts? More importantly, how often do people go back and forth in the comments? Every excuse for someone to return is the equivalent of a free promotion.

The problem is that depth is genuinely hard to measure. Open rates, time on page, scroll depth — these are all proxies, and imperfect ones. But you can feel it in other signals: reply rates, word of mouth, how people describe the publication to others, how often other publications link back to it as a source, whether readers show up consistently or only when an algorithm puts something in front of them.

If you’re building a media company, the temptation to optimize for reach is constant. Bigger numbers feel like progress. But the companies that end up being worth the most are almost always the ones that chose depth first and let reach follow naturally, not the other way around.

In an interview with Colin and Samir, TBPN’s founders talked about deliberately capping their ambitions at 200,000 subscribers. If they ever hit ten million, they said, something must have gone wrong. Their daily live show draws anywhere between 4,000 to 10,000 concurrent viewers, which sounds small until you think about who those viewers are. They’re executives and investors with the kind of spending power that makes a small number go a long way. The show is targeting $15 million in ad revenue in 2026 and that kind of economics doesn’t just come from reach. It comes from knowing exactly who you’re talking to and refusing to dilute it.

Optionality

Some media companies are just media companies. They produce content, they monetize attention, and that’s the business. There’s nothing wrong with that, but it has a ceiling.

Other media companies sit on top of something that could become more than media. They’ve built audience relationships, data assets, distribution infrastructure, or domain expertise that could power adjacent businesses in commerce, software, services, events, education, and more. The media is the foundation, but it’s not the whole structure.

This optionality is real value. It’s also the hardest thing to put in a spreadsheet because it’s not generating revenue yet. But the best acquirers and investors see it. They’re not just buying what a media company is today, they’re buying what it could become, given the assets it’s already built.

The key word is “could.” Optionality that’s never exercised is worth zero. What makes it valuable is a combination of the underlying assets being genuinely transferable to new contexts and a team that’s capable of actually making the transition. A media company with a highly engaged audience of software engineers could plausibly launch a recruiting business, a tool marketplace, or an education platform. Whether it’s actually worth more because of that depends on whether anyone there can realize that potential.

Recommended read: Is a $330m valuation insane for Semafor?

What this means in practice

None of these factors show up cleanly in a valuation model. They resist quantification, which is exactly why they create information asymmetry — and why understanding them is an advantage whether you’re building, buying, or selling.

If you’re building a media company: think about these factors early, not when you’re trying to sell. The structural decisions you make in the first few years like how you build your audience, how you diversify revenue, what dependencies you accept, determine your value years later in ways that are very hard to reverse.

If you’re evaluating a media company from the outside: the financials are the starting point, not the answer. Two companies with identical P&Ls can have wildly different risk profiles and growth potential based on the factors above. The numbers tell you what the business is doing today. These factors tell you what it’s likely to be doing in three years.

The media companies that are genuinely valuable tend to score well on most of these dimensions simultaneously. They own their audience. They’ve diversified their dependencies and their revenue. They’ve built depth before breadth. And they’ve created optionality that extends beyond content.

That combination is rare. Which is precisely why it’s valuable.

Vladimir Kharlampidi is a solo developer in Miami. He built Swiper, an open-source touch slider library that runs on websites like TikTok, Samsung, Coca-Cola, and more. He also founded Framework7, an HTML-based mobile app framework, and commercial products like t0ggles and PaneFlow. Together they've been downloaded millions of times.

We talked about what it's actually like to maintain open source software that half the internet uses, why developers are the most brutal and most loyal audience at the same time, and how he eventually figured out the money part.

Let's start at the beginning. How did Swiper happen?

It was the early days of touch smartphones going mainstream. Everyone was building for mobile but nothing felt native. Everything was laggy and I wanted to challenge myself to build something that felt smooth, touch-first from day one. I put it out there and it just took off because everyone was dealing with the same problem.

There's a line people like to draw between open source as charity and open source as business. You've said it's neither. What is it then?

It's this weird in-between that nobody really talks about. You can build something used by millions of websites, be a core piece of the internet's infrastructure, and still have no obvious way to make money from it. That's the reality for most open source maintainers.

That's worth sitting with for a second. We tend to assume that if something is widely used, someone is making money from it. Open source breaks that assumption completely. The value it creates is enormous but it flows outward, to every company and developer using it, not back to the person who built it.

So when did the money question actually become real for you?

When I left my regular job and started working on my open source projects full time. That's when it hit me that I needed to figure out the commercial side. Before that, it was something I could afford to not think about.

And the route you took was interesting. You didn't try to monetize Swiper itself. You built separate commercial products.

Right. I introduced new commercial products that weren't directly tied to my existing open source work. That made a big difference. The community was fine with it. If I had gone the other direction and started putting paid licenses on Swiper or Framework7, that would probably be a very different story.

This is something a lot of open source maintainers wrestle with. The moment you put a price tag on something people have been using for free, it feels like a betrayal, even if it's completely rational. Vladimir sidestepped that entirely by keeping the open source work open and building new things to charge for. It's a cleaner separation, though it also means you're essentially running two tracks at once.

Swiper does also generate some revenue through sponsorships and donations. Brands pay to have their logo and a backlink on the Swiper site and GitHub repo. It's often an SEO play but it also generates good traffic for these brands. There are also donations from supporters but it's a far cry from what a product with millions of users would typically bring in.

It's worth noting that there are other ways to approach this too. A lot of companies today use open source as a deliberate business strategy. You release the core software for free so anyone can use it, build a large community of users around it, and then charge for a hosted or managed version so people don't have to deal with running it themselves. Wordpress, Ghost, Supabase and many others do this. The software is free and open source, but most people pay for a hassle-free version. The open source part isn't charity in those cases. It's the top of the funnel. It gets people in the door and the paid product is waiting right behind it.

Vladimir's path was different. Swiper was just a library he built and gave away. There was no hosted version to sell, no premium tier, no natural upsell. The commercial side came later and it came in the form of entirely different products.

What's the worst advice you received that you're glad you ignored?

When I started doing open source, a lot of people told me it was a waste of time. That it wouldn't go anywhere, that nobody would care, that I should focus on real work that actually pays. And honestly, on paper they weren't wrong. You're giving away your work for free with no guarantee anyone will even notice.

But I ignored all of that and just kept building. Swiper became one of the most used front-end libraries on the web. Framework7 gave thousands of developers a way to build mobile apps. That "useless work" ended up shaping how a big chunk of the internet handles touch interactions. It gave me a reputation, a community, and the foundation for everything I'm building now.

Part of this advice does sound responsible. Focus on what pays. Be practical. And for most things, it's probably right. But open source is one of those rare areas where giving your work away for free can compound in ways that no paycheck would have. Not always, and not for everyone, but the returns can be reputational, educational, and open other doors you don't even consider.

You've said developers are the hardest audience in the world. What makes them so difficult?

They'll tear apart your code on GitHub, they expect everything for free, and they'll switch to an alternative the second something shinier comes along. But if you earn their trust, if your thing actually works and you keep showing up, they become the most loyal users you'll ever have.

What does that loyalty actually look like? Are people contributing back, or is it more passive?

It's mostly that they keep using it and telling others. Swiper has been around for over a decade and it's still growing. That doesn't happen by itself.

You mentioned you thought every product you built after Swiper would take off the same way. That didn't happen.

No. After that kind of success, I thought I had the formula. Just build something good and people will come. I launched a few things over the years, fully confident, and some of them completely flopped. What I got wrong was thinking a great product is enough on its own. Timing matters, distribution matters, understanding exactly who you're building for matters. With Swiper the timing was perfect: smartphones were exploding and developers desperately needed what I built. With other things the product was solid but the market wasn't there, or I didn't know how to reach the right people.

Do you regret any of those?

Not at all. Every failed product taught me something I'm using now. Not in a cliche way but I'm way more intentional about who I'm building for, how I position things, how I think about growth. I'd rather launch ten things and have three succeed than sit around perfecting one idea that never ships.

Maintaining a project for that long, does it ever stop being fun?

For me it's always been mostly fun. I've gained a lot of experience and knowledge along the way, and new technologies keep emerging so it stays interesting. And I have loyal users and contributors who are supportive. Knowing your work is appreciated and used by that many people is a great feeling.

You work alone on all of this. What does that actually feel like?

From the outside it looks cool. Multiple products and millions of users, but the reality is you're one person making every single decision. Product, code, design, marketing, support, taxes, legal. There's no team to bounce ideas off, no one to cover for you when you're burned out. Some days you ship something amazing and nobody notices. Other days everything breaks at once and there's only you to fix it. It can be lonely and exhausting too.

But you wouldn't change it.

No. I get to build exactly what I want, move as fast as I want, and answer to nobody. That freedom is worth all the hard parts.

If none of this existed, what would you be doing instead?

Before I got into development I was completely addicted to making music. I could easily see a timeline where I ended up as a music producer. That same obsession with crafting something and tweaking it until it feels just right, it's the same energy, just a different output. Or a video game developer. Games combine code, design, storytelling, sound. It's THE creative product.

I could probably just get a regular job as a developer somewhere. But I know myself. I'd last about three months before going crazy. I need full ownership, I need to be able to follow my own ideas. I think no matter what, I'd end up making something of my own. The medium might change but the urge to build doesn't go away.

What's changed your workflow the most recently?

AI agents. Once I started seriously using them, not just chatting with them but actually building with them, my output multiplied. Things that used to take me a week I can do in a day. It's like having a small team without actually having a team. The realization was that it's not about replacing what I do but complementing me against things that may slow me down.

I get the same feeling I had when touch smartphones first appeared and everything had to be rethought. We're still so early with this.

That's it. You can find Vladimir @nolimits4web on X or GitHub.

Most people think selling a startup is a big, exciting event. Andrew Gazdecki will tell you it's usually slow, opaque, and weirdly stuck in the past. He sold his first SaaS company, went through the whole painful process, and decided to build the platform he wished existed. That became Acquire.com.

I've been watching since the MicroAcquire days and through the rebrand to Acquire. It's one of those companies that's genuinely nice to see grow because it's giving founders a real path to building something sustainable and actually being able to sell it when the time comes. We work with them on all sides of the table, as buyers, sellers, and brokers, so we've seen firsthand how it works.

In this conversation, Andrew talks about why more money doesn't solve more problems, what actually makes a company sellable, how saying no became his biggest growth lever, and why his son naming the cat "Combo" might be the most grounding thing in his life right now.

What's your story in 30 seconds?

I’m a repeat founder who started, scaled, and sold a SaaS company, then built Acquire.com to help other founders do the same. I’ve raised venture, bootstrapped, had wins, taken hits, and learned that execution beats everything. Today I run Acquire profitably with a small team, focused on helping founders exit on their terms. I believe in moving fast, keeping things simple, and building real businesses that solve real problems.

What does your company do and why does it need to exist?

Acquire.com is a marketplace for buying and selling startups. We help founders sell their companies without brokers, crazy fees, or months of back and forth. And we help serious buyers find vetted, revenue-generating businesses in one place. It needs to exist because most founders have no clear path to liquidity. You can build something real, get profitable, and still have no idea how to sell it. The traditional M&A world is built for big companies, not bootstrapped founders doing $500K to $5M a year. We make exits accessible. Simple process. Transparent data. Direct founder-to-buyer conversations. Build something great. Then have a real option to sell it.

What moment made you decide to actually start it?

When I sold my first SaaS company. The process was opaque, slow, and controlled by gatekeepers. Brokers wanted huge fees. Buyers were hard to find. There was no simple place online where you could list a real software company and connect directly with serious acquirers. It felt crazy. We can spin up a company in a weekend. Launch globally. Process payments instantly. But selling a startup? That felt stuck in 1995. So I built the platform I wish existed when I was selling. Something simple. Transparent. Founder-first. That was the moment.

What's something about your industry that outsiders don't understand?

Most outsiders think startup acquisitions are big, flashy, headline deals. They’re not. The majority of exits are quiet. Profitable. $500K to $5M a year in revenue. Built by small teams. Sometimes solo founders. No press release. No TechCrunch article.

They also don’t realize how emotional it is. Selling a company isn’t just a financial transaction. It’s years of your life. Your identity. Your stress. Your wins and losses. And finally, most people think exits are rare lottery events. They’re not. If you build something real, solve a painful problem, and keep your numbers clean, there are buyers. Every day. It’s less about hype. More about fundamentals.

What's the worst advice you received that you're glad you ignored?

“Raise as much venture capital as you can. As fast as you can.” I did raise venture before. And I’m grateful for the experience. But the idea that more money automatically equals more success? That’s dangerous. It creates pressure to grow at all costs. To chase vanity metrics. To hire too fast. To spend before you’ve earned the right to. When I rebuilt Acquire, I focused on profitability. Real revenue. Small team. Tight expenses. Build a business that works without outside oxygen. That decision changed everything. Capital is a tool. Not a strategy.

What's something you were completely confident about a few years ago that turned out to be wrong?

A few years ago I was convinced that growth solved everything. More traffic fixes product issues. More hires fix execution gaps. More revenue fixes culture. It doesn’t. Growth amplifies what’s already there. If your product is messy, growth makes the cracks bigger. If your team is misaligned, growth creates chaos. If your margins are thin, growth just burns cash faster. What I’ve learned is that fundamentals matter more than momentum. Clean product. Clear positioning. Strong margins. Small, focused team. Then grow. Not the other way around.

What's working right now that you're excited about?

I’m really excited about the shift toward profitable, founder-first exits. For years the narrative was “grow at all costs and hope someone buys you.” Now I’m seeing founders build real businesses—profitable, sustainable, customer-led—and choose to sell them on their own terms. That changes everything. No hype. No vanity metrics. No “next billion-dollar outcome.” Just real companies solving real problems with real revenue—and buyers lined up because the economics actually make sense. That’s where the smartest founders are focusing right now, and it’s a huge upside for the whole ecosystem.

What's a small change you made recently that had a big impact?

We started saying “no” faster. Faster to features that don’t directly drive revenue. Faster to partnerships that look good but don’t convert. Faster to customers who aren’t a fit. That one shift created focus. The product got simpler. The roadmap got cleaner. The team stopped context switching. Revenue improved because we concentrated on what actually moves the needle: serious buyers and qualified sellers. Small change. Big leverage. Focus compounds.

What's something you're obsessed with outside of work?

My son. Nothing resets your perspective like a five-year-old asking you why the sky is blue or if a computer is just an Xbox for adults. Kids don’t care about ARR. They care about building Lego worlds and naming the cat something ridiculous like “Combo.” It forces me to zoom out. Build the company. Yes. Win. Yes. But don’t miss the small stuff. That’s the real long game.

What's a question you wish people would ask you?

I wish more people asked: “How do you actually build something that gives you options?” Not just how to raise. Not just how to grow fast. But how to build a company that’s profitable, simple, and attractive to buyers. Because that changes how you operate from day one. You focus on real customers. You care about margins. You document everything. You don’t build a mess you can’t sell. An exit isn’t something you think about at the end. You design for it from the start.

What would you be working on if this company didn't exist?

Probably another simple, profitable SaaS company. Something boring. Painful. Unsexy. A tool founders actually need and will pay for. Metrics. Churn. Maybe something in the AI workflow space that saves time and makes money immediately. I’m not wired to sit still. I like finding friction, building a clean solution, getting the first paying customer, and growing it without drama. At the end of the day I just like building. Acquire is the vehicle right now. If it didn’t exist, I’d still be building something.

What's one book, tool, or person you'd recommend?

Book: The Almanack of Naval Ravikant. It’s not a startup playbook. It’s a thinking playbook.

That's it. You can find Andrew @agazdecki on Twitter/X or LinkedIn.

This isn't that essay.

This is about the things you do that actively resist scaling. The things that get more expensive, more inconvenient, and more irrational the bigger you get. And the argument isn't that you should do them anyway as some temporary phase. It's that protecting them might be the whole point.

I still respond to most messages that come my way. Not the cold, cold pitches, but if someone took the time to write something real, I take the time to read it. I take meetings when people ask, especially if they're younger and clearly just trying to get a foot somewhere. I know I can't do this forever. But some of my closest collaborators came through exactly those conversations, and so did many of our hires.

My first hire happened because I accidentally answered an email while on vacation. A kid my age had reached out about a junior marketing position and I responded almost by reflex. We were supposed to meet and I stood him up because I couldn't figure out the schedule. I still feel terrible. I spent the rest of the day convinced I'd tell him I wasn't in a position to bring anyone on. We got on a call the day after and that's exactly what I said. He told me he wanted to work with us anyway, for free, despite having other paid offers on the table. He said what he saw in me was closer to the life he wanted to live than what he saw in his other interviews.

I said the hell with it, let's do it.

That night I thought I'd made a mistake. I woke up the next morning and I was a different person. Not because he turned out to be talented, though he did. Because the weight of being responsible for someone else's bet on you is the kind of thing that rearranges your priorities overnight. That feeling still carries me.

None of that was supposed to happen. An accidental email, a missed meeting, a conversation I tried to end before it started. One of the best things that came out of building this company arrived through a door I was actively trying to close.

There's a popular framework in scaling companies. You figure out what works, you systematize it, and then you remove yourself from it. And for most operational things, that's correct. You can't personally pack every order. You shouldn't be the only person who knows how the billing system works.

But somewhere along the way, this logic leaks into places it doesn't belong. It starts touching the things that aren't operational at all. The things that are, for lack of a better word, constitutional. The choices that define what kind of company you actually are.

The distinction matters. Operational things are how you deliver. Constitutional things are why anyone should care. And the problem is they don't come with labels. Nobody walks into a meeting and says "this is the thing that contains our soul, let's be careful with it." It usually looks like an inefficiency. It looks like something a consultant would flag.

When we were designing our logo, we brought in a prominent designer to realize our vision. We'd already spent countless days and nights in-house brainstorming concepts before bringing him in. He produced round after round of work. In his many years in the industry, he told us he'd never done so many revisions and concepts on a single job. It took so long that at some point he stopped caring about the increased pay. He was genuinely worried his work might never get used.

We ended up naming the icon The River, after the Springsteen song, because it was on repeat the entire time.

We finalized a concept and spent several more days refining it in-house. About two months later, I had a random light-bulb moment on a Saturday, immediately put together a draft, and rebranded all over again by Monday.

Was all that rational? Not by any standard measure. Believe me, I'm the last person to procrastinate on a logo before figuring out the offering. Evernomic didn't even have an updated website for the first three years of our journey because I didn't want a "Look! We're great." page. So when we rolled out our brand publicly, it had to be something that deserved to attach itself to our work. Even then I was initially planning to go with something low-effort, but it was my closest friend who reminded me "your work deserves better."

Do I regret all the back and forth? No. It wasn't about reaching perfection. It was about having no doubts. We needed to explore every concept just to scratch the itch and not leave any stones unturned.

Nobody will ever look at that logo and understand what went into it. That's fine. The point wasn't to produce something that screams effort. The point was to make a decision we could live inside of.

Saying no is the other half of this, and it's the half I still often struggle with.

There was an opportunity that came up that was genuinely good. Not a bad deal with bad people — the opposite. Everything about it was right on paper. But it required my time personally, and I had commitments to my team that needed that time instead. So I turned it down.

That's a boring story. There's no villain, no red flag, no dramatic walkout. But I think the boring version is actually the more common and more important one. Most of the decisions that define a company aren't choices between good and bad. They're choices between good and good, where the difference is what you've already promised and to whom. The discipline is in honoring commitments that nobody would blame you for breaking.

Here's what I think actually happens to most companies. They don't sell out in some dramatic moment. They just optimize, one reasonable decision at a time. Each decision makes sense in isolation. Automate this. Delegate that. Outsource this other thing. And slowly, without anyone noticing, the company becomes a perfectly efficient machine that produces something nobody has any particular feeling about.

The things that made it worth caring about weren't features or processes. They were choices. Small, specific, often expensive choices, about what kind of place this would be and what kind of people would build it. Those choices are the first things to go when the spreadsheet starts talking.

We've made a lot of hires on character. Not exclusively, but meaningfully. The designer I mentioned before — one of the reasons we brought him on was that I texted him at 2:30 in the morning and he responded within the same minute. He started on our first concept the next morning. Days later he was at a bar and still brainstorming with me. I liked that. Not because I expect people to be available at 2:30AM, but because it told me something about how he related to work. It wasn't a job to him. It was a thing he was in.

We're not a company in the traditional sense of people who happen to work at the same place. We're closer to a family. We care deeply, we're extremely close, and the work isn't something we do just because it's our job. That's not a recruitment pitch. It's a description of something that exists because we've protected it, actively, against the pressure to professionalize it into something more manageable.

So here's what I'd actually suggest, not as advice but as a exercise worth doing.

Map out the things in your company that are expensive, slow, or irrational. The things a smart advisor would tell you to fix. Then ask yourself: which of these are operational inefficiencies, and which are constitutional choices?

Operational inefficiencies should be fixed. If you're manually doing something that a system could do better, fix it. Don't romanticize friction.

But constitutional choices like the way you hire, the way you treat people's time, the quality threshold you refuse to lower, the deals you walk away from, those need protection. Not because they're efficient. Because they're the reason you're building this thing and not something else.

The discipline isn't in scaling. Everyone scales. The discipline is in knowing what to refuse to scale, and having the nerve to protect it when the numbers start suggesting you shouldn't.

That's the stuff that compounds. Not into revenue, necessarily. Into identity. Into the kind of place where someone texts you at 2:30AM not because they have to, but because they're in it with you. You can't scale that. You can only decide not to destroy it.

Ben Francis, Gymshark's founder, stepped aside as CEO in 2017, bringing in experienced retail executive Steve Hewitt. During this time, Francis focused on product development and brand building. In August 2021, having gained valuable experience and perspective, Francis resumed the CEO role, when Gymshark's valuation had already soared to over £1 billion. His rational choice to recognize his own capabilities and limitations is something every founder should admire.

The Founder-CEO

The startup ecosystem has long perpetuated the idea that founders should naturally transition into the role of CEO. This notion is reinforced by high-profile success stories like Mark Zuckerberg at Facebook or Jeff Bezos at Amazon. However, this one-size-fits-all approach often overlooks a crucial reality: the skills required to conceive and launch a startup are vastly different from those needed to scale and manage a growing company.

Founding a company requires vision, creativity and the ability to innovate rapidly. It often involves wearing multiple hats and making quick decisions with limited information. In contrast, leading a maturing company demands strategic thinking, operational excellence and the ability to build and manage teams effectively.

Taking Twitter as an example, while Jack Dorsey co-founded the platform, his initial tenure as CEO was short-lived. It wasn't until years later, after gaining more experience, that he returned to the role. This shows that even brilliant founders may not be ready for the CEO role immediately — and that's okay.

I have had countless conversations with brilliant founders who feel trapped when committing to scaling a singular project. Every person has different strengths. Many founders excel at ideation and creating groundbreaking products but find the day-to-day operations of running a growing company constraining. Recognizing this disconnect doesn't diminish the founder's crucial role; you would never ask a master chef to manage the restaurant's finances, would you?

The Hidden Costs of Founder-CEOs

When founders insist on remaining CEO despite lacking the necessary skills, the costs can be significant and far-reaching. One of the most detrimental effects is the limitation it places on talent acquisition and retention.

High-caliber executives are attracted to companies where they can learn from experienced leaders and see a path for their own growth. If a company is led by a founder who's learning on the job, it may struggle to attract top-tier talent. This creates a ceiling effect, where the company can never hire anyone more qualified than the founder-CEO.

Moreover, this dynamic can lead to a dangerous echo chamber. Without experienced voices in the C-suite willing to challenge the founder's ideas, companies risk making costly strategic mistakes.

A relevant case of this is WeWork where Adam Neumann's unchecked control as founder-CEO led to questionable decisions and eventually derailed the company's IPO plans, destroying billions in value.

Knowing When to Step Aside

Recognizing when to transition out of the CEO role is a sign of maturity and true commitment to the company's success. Here are key indicators that it might be time:

1. If you're constantly feeling overwhelmed or unprepared for the challenges you're facing, it might be time to bring in more experienced leadership.

2. If the company's growth has stalled despite a strong market position, fresh leadership could provide new perspectives and strategies.

3. If you're more passionate about product than management, or if you find yourself longing to return to the creative or technical aspects of the business, it might be time to transition to a role like Chief Product Officer or Chief Technology Officer.

4. If the company is consistently struggling in key areas like financial management, operational efficiency or scaling, it may benefit from more experienced executive leadership.

When founders do decide to step aside, it doesn't mean abandoning the company. Many find success in alternative roles that leverage their strengths. A good example is Chief Innovation Officer where the founder focuses on driving new product development and keeping the company at the cutting edge.

Alternatively, the founder could become the Executive Chairman or a Board Member to provide strategic guidance and maintain key relationships while leaving day-to-day operations to the CEO.

When Google's founders Larry Page and Sergey Brin brought in Eric Schmidt as CEO in 2001, it allowed them to focus on product innovation while Schmidt guided the company through tremendous growth and a successful IPO.

I would even argue, most startups don’t need a traditional CEO in the early stages. What they need is a founder but these two roles have become interchangeable in today’s startup landscape.

Remember, stepping aside isn't an admission of failure, it's a strategic move to ensure your company's long-term success. By putting ego aside and focusing on what's best for the business, founders can often achieve far more than they could by insisting on remaining CEO. The true measure of a founder's success isn't their title, but the enduring impact of the company they've created.

Ask yourselves, would you rather lead a mediocre startup or be the founder of an incredible company?

One thing in particular that we stuck to was initially focusing on media-based startups. To put it simply, I identified what I suspected we would be competing on in the future — skills, experience, network, capital and so on. The fact is, most of the above are prerequisites that every firm must possess. However, if we had a strong portfolio of audience-based offerings, we could leverage that in numerous ways to propel us forward.

Effortless Networking

In the media industry, almost every demographic can benefit from your work in some way, ranging from businesses seeking promotions to consumers seeking information, which sets a unique stage for networking. The broad appeal and reach of media can open doors to valuable circles and opportunities that might otherwise remain inaccessible.

For instance, with Groningen Mail, a digital newspaper we manage in the Netherlands, we pursue strategic partnerships with local organizations and associations by offering them free coverage of their initiatives. Naturally, we must maintain the quality of our content so we are rather selective with the organizations we approach. Nonetheless, this local network has not only strengthened our community ties but also connected us with invaluable contacts for our international projects.

Promoting Your Own Initiatives

Media platforms offer an exceptional channel to market your own projects and initiatives directly to your audience. This direct line of communication allows you to shape the narrative and control the messaging around your products or services, also ensuring that your promotional efforts align perfectly with your brand's voice and goals.

It goes without saying that you should never exploit your audience’s trust and spam promotional materials. However, you understand the preferences of an audience you manage better than anyone which enables you to engage effectively with such campaigns.

By consistently communicating with your audience through these platforms, you can build a loyal customer base that is more receptive to your new and existing offerings. This strategy not only enhances brand visibility but also drives engagement and sales more effectively than traditional advertising channels.

Recycling Your Audience

One of the most strategic moves in media is the ability to recycle an existing audience to benefit other projects or brands within your portfolio. A prime example of this is our approach with Internet Is Beautiful, one of our prominent media brands with a highly engaged audience.

Instead of continuously promoting our projects to the same audience, we arranged cross promotions with other creators and media brands. However, instead of them promoting Internet Is Beautiful, they would promote a different venture of ours. This tactic allows us to introduce our projects to several audiences, by utilizing a single audience, without additional acquisition costs.

Access to Market Insights

Operating a media entity provides more than just an outlet for content; it offers invaluable market insights derived from audience data and content interactions. This continuous stream of data includes consumer preferences, behavioral trends, and engagement metrics, which are critical for tailoring content and marketing strategies.

Such insights also enable media companies to anticipate market trends, adapt to consumer needs more swiftly, and make informed decisions that align with both current and future market dynamics. The ability to analyze these insights gives media investors a significant advantage in staying ahead of the curve.

Influence in Strategic Partnerships

The influence gathered through successful media projects is a valuable tool in forming strategic partnerships and negotiating deals. Media companies can leverage their reach and visibility to attract and secure beneficial partnerships with other brands, sponsors and influencers. This influence acts as a currency that provides media owners with the leverage needed to negotiate favorable terms and collaborate on projects that can amplify mutual success.

Whether it be on a local scale or an international one, when Evernomic seeks partnerships with new startups, the most common obstacle they face is exposure and ineffective marketing. Our media portfolio has been an invaluable asset in solving such obstacles with minimal inconveniences on our end.

High Profit Margins

Media projects offer attractive profit margins, particularly once an established audience is in place. With various revenue streams such as advertising, subscriptions and sponsored content, media companies can significantly increase profitability.

After the initial phases of setup and audience building, the costs of content production often decrease, while revenue potential scales with audience size and engagement. This scalability and the ability to leverage content across multiple platforms enhance the profit margins, making media investments particularly lucrative.

I urge you to look around the global business landscape, the most innovative organizations have been building or acquiring media assets rapidly for some time now. Especially given the more efficient pathways to creating content these days, setting up media subsidiaries should be a strategy all businesses should consider undertaking.

Lack of Quality Deal Flow

The public marketplace scene has become a graveyard of expired trends. Just look at what's happening right now — marketplaces are flooded with AI wrapper applications, mostly built in the last twelve months, trying to catch the AI wave. Before that, newsletters, crypto and dropshipping stores dominated listings in their respective eras.

This cycle reveals a crucial problem: by the time these businesses hit the market, the opportunity has usually passed. The seller has likely noticed declining returns and wants to exit before things get worse. It's like trying to sell an umbrella after the rain — you might find a buyer but they're probably not going to get much use out of it.

There is also the growing trend of "acquisition builders" — entrepreneurs who specifically build businesses to sell them quickly. These operators often create superficially attractive businesses optimized for marketplace metrics but lacking in substance. They might show good revenue numbers but dig deeper and you'll find minimal customer loyalty, high churn rates and shaky foundations.

Self-Sabotaging Dynamics

Unlike physical businesses, where an owner might sell because they're moving cities or retiring, digital businesses don't face the same constraints. A profitable online business can be run from anywhere, often with minimal time investment. Need to move? Hire a remote team. Too busy? Bring in a fractional CEO. The flexibility of digital operations means healthy businesses rarely need to sell.

This creates a troubling dynamic: when you see a promising digital business for sale, you have to ask yourself — why? Unless it's a premium private deal, the answer often reveals underlying problems.

The selling process itself creates another barrier. I recently spoke with a founder who spent nine months trying to sell his SaaS business. By the time he found a buyer, his metrics had declined because he had spent more time on the sale than on the business. This isn't uncommon. Pursuing an acquisition often becomes a full-time job, which means those who commit to the process usually have a pressing reason to exit.

The Marketplace Dilemma

Public marketplaces face their own structural challenges. They need standardized valuation methods to serve a broad audience, which usually means focusing on revenue multiples. This one-size-fits-all approach fails to capture the nuanced value of pre-revenue or IP-driven startups. This is not to put the blame on the marketplaces, it’s simply a trade-off to satisfy the masses.

For instance, I once acquired a highly established, but pre-revenue, directory that provided me access to a growing network of newsletter creators through its submissions. No marketplace could properly value it because there was no revenue to multiply. However, it was invaluable to me as I still leverage that same network to solve the chicken-and-egg problem for an ad network we are launching. These kinds of strategic acquisitions often don't make sense within the marketplace framework as most other buyers would not derive the same value as I have.

Why There Is Still Hope

Despite these problems, the digital acquisition market is becoming more interesting than ever. The barriers to building digital products are falling rapidly, with tools like Lovable that turn a simple prompt into a functional MVP. This democratization of development means we will see more digital products launching — and more opportunities for acquisition.

However, as building becomes easier, the value increasingly lies in existing assets — established user bases, proven distribution channels and accumulated data. Instead of spending heavily on social media ads to build an audience from scratch, smart operators are looking to acquire existing projects in their target niche.

The digital M&A scene is also maturing. Many technical founders are realizing they enjoy building products more than running businesses. When we reach out to interesting projects that aren't officially for sale, we almost always find founders open to acquisition discussions. Everything has a price and more founders are recognizing acquisition as a viable exit strategy.

This openness coincides with the fact that running a digital business is becoming increasingly manageable. Modern tools have simplified operations to the point where some are betting that we'll see the first one-person unicorn soon. This operational efficiency makes acquisitions less daunting which opens the market to more potential buyers.

Moving Forward

The only way to capitalize on this market lies in understanding its limitations. The best opportunities rarely appear on public marketplaces. Instead, they are found through networks, direct outreach and industry relationships. Smart acquirers are building expertise in specific niches and approaching potential acquisitions before they hit the market.

For sellers, the focus should be on building sustainable businesses rather than optimizing for a quick exit. Paradoxically, this approach often leads to better acquisition outcomes, even if selling wasn't the initial goal.

The digital acquisition market may be broken in its current form but, for those who know where to look, it presents more opportunities than ever.

Past Success Can Be Misleading

Many founders believe they need to hire from successful tech companies and seek candidates with impressive track records. This seems logical but often backfires. Early-stage startups operate in uncertainty, with limited resources and unclear direction. Success at a large company doesn't predict success in this environment. In fact, it can be a liability.

The skills that make someone successful at a large tech company — managing established processes, working with complex organizational structures and optimizing existing systems — are often at odds with what startups need. Early-stage companies require people who can create structure from chaos, build systems from scratch and make decisions with limited information.

Moreover, candidates from big tech companies often struggle with the lack of support systems in startups. There are no large teams to delegate to, no established processes to follow and no safety nets. The ability to operate without these support structures is crucial, yet it's rarely developed in larger organizations.

Founders also tend to overvalue industry experience, particularly in their market. But in the early stages, the ability to learn quickly and adapt to change matters far more than deep industry knowledge. The market you think you're entering often isn't the one where you'll find success.

Early Hires Create Culture

Most founders understand culture matters but few realize how deeply early hires shape it. Your first ten employees don't just do the work — they define how decisions get made, how people communicate and how the team handles pressure. These patterns become deeply embedded and extremely difficult to change later.

Technical skills can be taught but values and working styles are much harder to shift. Smart founders spend as much time assessing how candidates approach problems and interact with others as they do evaluating their technical abilities. They understand that these early hires will become the benchmark against which future candidates are measured.

As my company, Evernomic, is scaling to an internal team of nearly 50 people, we’ve still maintained an average age under 25 years old. I opt for younger individuals who, despite lacking decades of industry experience, have their core values aligned with mine. Competence can be acquired but the character they bring to the table is far harder to replicate. I aspire for a team who I can not only trust in a board meeting but also with the keys to my house.

The cultural impact of early hires extends beyond their immediate team. They become the company's first managers which sets the tone for how leadership operates. They influence how the company deals with conflict, how it celebrates success and how it handles failure. Their behaviors and attitudes become the unwritten rules of company culture.

Specialists Often Struggle

Early-stage startups need people who can adapt as the company's needs change. Hiring too many specialists too early is a common mistake. While every startup needs some specialized expertise, the first team members should be comfortable stepping outside their defined roles.

Most successful early-stage companies build teams of adaptable people who combine deep expertise in one area with the ability and willingness to help wherever needed. This flexibility proves invaluable as priorities shift and new challenges emerge. The best early employees often end up in roles very different from the ones they were hired for.

The danger of specialists isn't just their narrow focus — it's that they often resist taking on work outside their specialty. Early-stage startups need people who see their role as "whatever needs to be done" rather than a specific function.

Taking Ownership

The strongest early employees think and act like founders, not employees. They spot problems and fix them without being told. They lose sleep over challenges and celebrate wins as their own. This mindset is rare and doesn't always correlate with experience or previous employers.

True ownership means being willing to do unglamorous work while keeping sight of the bigger picture. It means taking responsibility not just for completing tasks but for achieving outcomes. Most importantly, it means caring deeply about the company's success beyond one's immediate responsibilities.

This quality is particularly crucial because early-stage startups lack the management bandwidth to closely supervise every activity. They need people who can operate autonomously while staying aligned with company goals.

Looking Beyond the Usual Suspects

Building a team that thinks and experiences the world in similar ways is a recipe for blind spots. The strongest early teams combine different perspectives, backgrounds and ways of thinking. This helps companies avoid the echo chambers that can lead to costly mistakes.

Having different educational backgrounds, career paths and life experiences all contribute to a team's ability to see opportunities and challenges from multiple angles.

Duolingo's early success demonstrates this perfectly. Rather than staffing their team solely with experienced EdTech professionals, they deliberately built a team that included linguists, gaming designers and data scientists from various cultural backgrounds. Their varied perspectives led to the gamified approach that has now helped millions learn new languages. This wasn't just about having different skills — it was about bringing together people who thought about education, motivation and learning in fundamentally different ways.

Your early team shapes everything that follows. The way your early team works becomes your company's default operating system. Their approaches to problem-solving become your company's standard practices. Their values become your company's culture. This is why rushing these early hires out of desperation or convenience can have such devastating long-term consequences and vice versa.

Genuine Curiosity

One powerful yet underrated trait of successful founders is genuine curiosity about people and ideas. Great entrepreneurs aren't simply networking — they're authentically interested. Brian Chesky, co-founder of Airbnb, frequently stays in Airbnb homes himself. He doesn't do this for publicity; he's genuinely curious about the experiences of hosts and guests.

Curiosity goes beyond asking questions, it's about truly wanting to understand. Founders who constantly ask "Why?" or "What if?" build stronger relationships and stumble upon solutions more naturally.

Paying Attention to Small Details

Exceptional founders pay close attention to personal details which makes those around them feel valued. One of my mentors used to take quick notes on the back of business cards she was handed whenever she met someone new — a recent hobby of theirs, their children's accomplishments or news about their relatives. Months later, she would casually reference those details which created authentic connections. This ability turns routine interactions into lasting relationships that may open doors others never even see.

It also helps you grasp someone’s character deeply enough to ask thoughtful, unexpected questions. Instead of asking about basic business metrics like conversion rates — something they’ve likely been asked countless times — you could inquire about how their personal values have shaped their business approach. These questions not only set you apart but make people feel genuinely understood.

Being Open About Failures

Entrepreneurs who openly share their challenges and setbacks often gain deeper trust and stronger connections with their team and audience. Acknowledging difficulties transparently not only promotes reciprocal honesty but also makes you more relatable. Rather than projecting constant perfection, embracing vulnerability also establishes a culture where initiatives thrives, as teams feel safer taking risks and sharing bold ideas.

Connecting Others Without Expectation

Great founders don't just build products — they build communities. Meaningfully connecting people is a rare skill that significantly amplifies influence. True connectors pay attention to who needs to meet whom and actively facilitate introductions by subconsciously connecting the dots among their network.

They understand that success is often collaborative and are always looking to bridge gaps within their networks. This proactive approach turns such founders into valuable resource centers which positions them as indispensable and influential figures in their industry.

Not Treating Relationships as Transactions

Founders must avoid being transactional and not approach every interaction as a business pitch or networking opportunity. Instead, relationships should be built humanely by being decent without expecting immediate returns.

For example, I make it a habit to never pitch myself, my company or my work in casual conversations. If someone is interested, they'll naturally discover it. I'd rather talk about something personal and connect authentically. I’ve seen founders who practice this approach naturally build deeper trust and long-lasting connections.

Have a Clear Motivation

It's not necessarily about passion; however, when people clearly sense what's in it for you, they trust and relate to you more. Most entrepreneurs say their motivation is to make an impact but, in most cases, that's simply a cliché response.

Every founder must define their own drivers. For example, my primary driver is storytelling and it is visible in many things I do. I've gone out of my way several times just to create memorable stories. People notice and appreciate this authenticity.

When your motivations are clear and unique, it sets you apart from the crowd and builds trust effortlessly.

Be Memorable

However you choose to achieve this, ensure you're not forgotten. I once attended a startup conference where a founder faced technical difficulties during her pitch. She was upset but, ironically, she became the most memorable and approached participant because people noticed and remembered her.

While this instance was accidental, you should intentionally create memorable moments. A close associate of mine, a well-known media personality, only wears black outfits to broadcast a uniform image. Whether through your dress, conversation style or humor, make yourself someone people naturally remember.

Show Real Understanding

People respect founders who can explain complex concepts simply, clearly and without relying on buzzwords to sound smart. One of my most memorable conversations was with a founder who demonstrated, in plain language, how his space-related technology could also be used for ocean exploration. This simple clarity stuck with me and made his idea resonate deeply.

Founders who communicate clearly and understandably build stronger credibility and lasting impact.

Reading Between the Lines

Founders who sense what's left unsaid often find themselves ahead of the curve. It's not just about body language but about picking up subtle conversational cues and understanding hidden motivations.

Effective leaders also recognize patterns in behavior and communication to anticipate concerns or needs before they're explicitly voiced. They can identify underlying discomfort or enthusiasm, which helps them manage situations proactively and strategically. This perceptive ability can significantly improve negotiations, decision-making and relationship management by making you less susceptible to surprises.

These soft skills aren’t just extras — they’re the difference between good founders and unforgettable ones. Technical skills get you started but it’s how you connect, communicate and leave an impression that makes people truly invest in you.

Single-Player Mode

The key to solving the chicken-and-egg problem often lies in temporarily ignoring it. Instead of trying to build both sides of your marketplace simultaneously, focus on creating value for one side first.

Airbnb, now a household name, started by targeting hosts in New York City during major events. They manually reached out to potential hosts, helping them list their properties and even offering free professional photography services. By ensuring a reliable supply of attractive listings, they created a compelling reason for travelers to use their platform.

As a rule, identify which side of your marketplace is more vital to acquire and start there. We are launching an ad network soon and faced the same dilemma months ago. So, we acquired several niche products that attract creators, such as newsletter directories. As a result, we have a creator network that can sustain the launch and further growth of our platform for the foreseeable future. Now, all we need to do is to get advertisers to come on board as well. So, in similar cases, create an offering that provides value to one group even without the other side present.

Fake It Till You Make It

In the early days, your marketplace might look a bit empty. Don't let this deter you. Instead, roll up your sleeves and start curating content manually.

Reddit, in its early days, faced the challenge of appearing active and engaging without a user base. The solution? The founders created numerous fake accounts and populated the site with interesting content themselves. This created the illusion of an active community which attracted real users who then contributed their own content.

The Piggybacking Strategy

Why build a network from scratch when you can tap into existing ones? This strategy involves identifying platforms where your target users already congregate and bringing them onto your marketplace.

PayPal executed this brilliantly by integrating with eBay. They targeted power sellers and offered a more efficient payment solution. As these sellers adopted PayPal, buyers naturally followed, rapidly growing both sides of their payment marketplace.

The Exclusivity Gambit

Nothing drives demand quite like exclusivity. By limiting access to your marketplace, you can create a sense of scarcity and desirability that attracts both buyers and sellers.

When Spotify entered the U.S. market, they used an invite-only system. This not only allowed them to manage growth but also created buzz and anticipation. People clamored for invites, and when they finally got in, they were more likely to actively use the platform.

Plus, this way, you are not building expectations of immediately going mainstream. A quieter marketplace would be acceptable and expected by your existing users.

The Loss Leader

Sometimes, you need to sweeten the deal to get your first users on board. This might mean operating at a loss initially but it can pay off in the long run.

Uber, in its early days, offered heavily subsidized rides to passengers and guaranteed minimum earnings for drivers. This dual-sided subsidy quickly built up both supply and demand which created the network effects necessary for sustainable growth.

The Network Effect

Design your product with viral growth in mind. Make it not just easy but advantageous for users to bring others onto the platform.

Dropbox nailed this by offering additional free storage to users who referred friends. This incentivized users to become advocates for the platform and it rapidly grew the user base at minimal cost to the company. The beauty of this approach lies in its simplicity and scalability — each new user became a potential vector for further growth and created a self-perpetuating cycle of expansion.

Trust and Credibility

In the world of marketplace startups, trust is your most valuable currency. Without it, neither buyers nor sellers will feel comfortable transacting on your platform, no matter how slick your UI or how vast your offerings.

Etsy faced this challenge head-on. They implemented a review system that allowed buyers to rate not just products but sellers too. They also introduced secure payment methods and buyer protection policies. These measures created a safe environment for transactions and encouraged more buyers and sellers to join the platform.

Another great example is Airbnb's implementation of host and guest verification processes. By requiring users to verify their identities, they significantly reduced the perceived risk of peer-to-peer transactions in the short-term rental market.

Solving the chicken-and-egg problem in marketplace startups is no small feat. It requires creativity, persistence and a willingness to experiment. By focusing on one side first, manually curating initial offerings, leveraging existing networks, creating exclusivity, offering irresistible incentives, designing for viral growth and building credibility, you can overcome this hurdle and set your marketplace on the path to success.

The key is to start small, focus on providing real value and be patient. Rome wasn't built in a day and neither are successful marketplaces.

Embracing Slow-Burn Growth

Contrary to the "move fast and break things" mantra that echoes through Silicon Valley, bootstrapping often means adopting a steady and deliberate approach. This allows for a deeper understanding of your market and more meaningful connections with early customers.

For instance, instead of chasing rapid growth, Tuple focused on building a product users would truly love. Their strategy revolved around a relentless focus on user feedback and incremental improvements. By prioritizing the quality of their screen-sharing functionality, a critical feature for developers, over rapid expansion of their feature set, they created a loyal user base that fueled organic growth.

Steering Your Own Ship

Bootstrapping isn't just about money, it's about maintaining the purity of your vision. When you bootstrap, you retain complete control over your company's direction, culture and values. This autonomy can be invaluable, especially if your vision doesn't align with typical investor expectations.

Keep in mind, maintaining control doesn't always mean rejecting all external input. Mailchimp, which bootstrapped its way to a 2 billion acquisition by Intuit, did seek advice from outside experts. The difference was that the founders had the freedom to choose when and how to implement this advice.

Can Your Model Fuel Itself?

The ideal bootstrap-friendly business generates revenue quickly and requires minimal upfront investment. This often leads bootstrapped startups to focus on solving immediate, painful problems for customers willing to pay for solutions.

Gumroad, a platform for creators to sell products directly to consumers, built its business model around immediate monetization. By taking a small cut of each transaction, Gumroad aligned its success directly with that of its users.

Being bootstrap-friendly often requires creativity in finding ways to generate early revenue. Pieter Levels, founder of Nomad List, bootstrapped his company by creating multiple small products and services for digital nomads. This diversified approach allowed him to generate revenue streams that collectively funded the growth of his main platform.

Walking the Line Between Brave and Foolish

Bootstrapping often means betting on yourself — sometimes quite literally. It requires balance between taking necessary risks and avoiding reckless gambles. This often involves personal sacrifices and a willingness to operate with a much thinner safety net than funded startups.

When Sara Blakely was starting Spanx, she kept her day job selling fax machines while developing her product nights and weekends. She invested her entire ,000 savings and even wrote her own patent to save on legal fees.

The key is to be realistic about your risk tolerance and financial situation. It's about finding creative ways to extend your runway and validate your ideas before going all-in. This might mean starting as a side project or finding ways to generate supplementary income that aligns with your long-term goals.

Building Big While Starting Small

One of the most pervasive myths in the startup world is that certain ideas require massive scale from day one, necessitating significant upfront investment. However, numerous examples prove that it's possible to build a large, impactful company from humble beginnings.

Shopify, which now powers over a million businesses, started as a simple online store for snowboarding equipment. They bootstrapped the company initially, only seeking outside investment after they had a proven product and clear market demand.

This paradox is often resolved by starting with a laser focus on a specific, underserved segment of your target market. By dominating this niche, you can build the resources and reputation necessary to expand into adjacent markets or scale up to serve larger clients.

Turning Constraints into Advantages

One of the most powerful aspects of bootstrapping is how it forces creativity and efficiency. With limited resources, bootstrapped startups often find innovative solutions that end up becoming key competitive advantages.

Referring to Basecamp’s journey again, their limited resources led them to focus on doing a few things exceptionally well, rather than trying to match every feature of their competitors. This constraint-driven innovation resulted in a product known for its simplicity and ease of use — qualities that became major selling points.

Building a Team with More than Money

One of the biggest challenges bootstrapped startups face is attracting and retaining top talent without high salaries and extensive benefits packages. However, many bootstrapped companies have found innovative ways to build strong teams despite these constraints.

By openly sharing the company's revenue, salaries and equity distribution, Gumroad attracted talent that was aligned with their values and excited by the opportunity to work in such an open environment.

Many top performers are motivated by factors beyond just salary. Autonomy, mastery, purpose and work-life balance can be powerful attractors, especially for those disillusioned with the high-pressure environments often found in heavily funded startups.

Defining Success on Your Terms

The bootstrap path can lead to unexpected and often more favorable exit opportunities. When you bootstrap, you retain more equity and have more control over the timing and terms of any potential exit.

When Mailchimp was acquired by Intuit for 2 billion, the founders owned 100% of the company, a feat unheard of in tech unicorns. Their bootstrap journey allowed them to grow the company at their own pace and exit on their own terms.

An "exit" doesn't necessarily mean selling or going public. Success can be defined in many ways — building a profitable business that supports your desired lifestyle, creating a company that makes a positive impact on the world, or yes, eventually selling for a significant sum.