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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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.