You Don’t Know Yet

Founders don’t know what problem they’re solving yet, and neither do any of their customers, and the annoying part is that this is not actually bad news, because if you stay in it long enough, you will eventually figure it out.

The Product Is Bait

The way it usually goes is this: You build something that takes a particular angle on a particular problem in a particular industry (probably one you know pretty well, or think you do), and one of two things happens. You either get sucked into a kind of product development haunted house where it has to be just a little more complete before it’s ready, and the dashboard needs better onboarding, and what if it had a Slack integration, and maybe the logo should feel more “enterprise” (I have never once heard a satisfying definition of what “enterprise” means as an aesthetic), or you get a version out the door and into the actual market, where it doesn’t sell. Not selling is, counterintuitively, on ok outcome. It won’t feel good, it’ll feel like capitalism personally singled you out for a lesson, but what you have now is a real artifact that maybe 1% of your original intended market can react to, and that 1% is enormously valuable because real reactions are the only raw material that matters. You can now take that product (which is bait, more than anything else) and you start showing it to ten, twenty, thirty potential customers, watching their faces and listening to what they complain about.

Feature-Requested to Death

At first, they will try to feature-request you to death. These requests will feel very convincing because customers say things like “if it could just hook up to our QuickBooks instance, I’d buy it tomorrow” or “if the AI could handle this last piece of the workflow, this would be an absolute game-changer for us” (they will ALWAYS ask if it can export to Excel, a request I believe predates the spreadsheet and may outlast the species). So you go back to your team, you build as fast as you can, you ship version two with all the new features, you go back to those same customers, and if you are good, AND lucky they will tell you the exact same thing: there are just one or two more features they really need, and then this thing will fix the problem once and for all, and you are almost there.

The Roadmap Graveyard

I’m going to pause the loop here because it can go on for twenty iterations (and I’ve seen it go longer). The real tragedy is that a lot of founders never even get this far, because their demo customers have them trapped in feature-development purgatory forever… or their own brains trap them there, because the product has to be perfect before any real human is allowed to see it. Those products die in roadmaps and “just one more thing” conversations, and never get rejected by the market because they never actually reach it.

Eventually, You Start Seeing the Elephant

But if you can stay in the conversation long enough, past the feature requests and the individual customers and the literal words people are saying to you, something strange starts to happen. You become, through sheer accumulated exposure, the world’s leading expert on the problem your customers all have in common. Not the problem you thought you were solving when you started, and not the problem any one of them has described to you, but the actual structural problem that everyone is bumping into from different directions (Schlep Blindess) without being able to name it, because nobody has a view of the whole thing. One customer tells you it’s the accounting system. Another says it’s logistics. A third says the two systems don’t talk to each other. A fourth blames someone named Susan in operations (this may or may not be fair to Susan… but yeah, wtf Susan?) Each of them is holding a piece of the elephant, the trunk or the tail or the foot, and describing it with complete sincerity, and they are all correct about their piece, and none of them can see the animal.

You, Neo, Are The One!

You are the only person who has talked to all of them, which means you are the only person positioned to eventually see the whole thing. The insight doesn’t come in a meeting and it doesn’t come from a good customer interview; it comes sideways, usually while you’re not looking for it. You’re at lunch with a client and one of their direct reports walks in with a quick question, and two people start having a conversation right in front of you, and the boss asks why the system can’t do something, and the user explains the workaround, and a third person adds “we only do it that way because finance needs the numbers by Thursday,” and a piece clicks, and then another, and then another. You suddenly understand that the product you built wasn’t the product at all; it was the thing that got you close enough to understand what the actual product should be, which turns out to be a considerably more interesting thing to build.

Earning the Right to Understand

The first version won’t be right, and the second version probably won’t be right either, and that is not failure… that is the process of earning the right to understand what you’re actually building (see Paul Graham’s “How to Get Startup Ideas“). Most founders want to skip straight to the insight, want the clean customer discovery process and the tidy MVP and the market telling them in bullet points exactly what to build, and that is just not how it works. You build the wrong thing, you launch it, you survive, you talk to as many customers as you can stand, you resist becoming a short-order cook for every prospect with a credit card, and you keep looking for the pattern underneath all the noise until eventually you see the elephant.

That’s when the real company starts.

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I help companies turn their technical ideas into reality.

CEO @Sourcetoad and @OnDeck

Founder of Thankscrate and Data and Sons

Author of Herding Cats and Coders

Fan of judo, squash, whiskey, aggressive inline, and temperamental British sports cars.

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Things I Wish I Knew Before Selling My Company

…or, how to survive due diligence without screaming into a pillow (too often)

On January 1st, 2026, Sourcetoad was acquired by Thompson Holdings. That part’s public now, and I can say, I couldn’t have hoped for a better outcome. We landed inside an employee-owned ESOP structure, surrounded by genuinely kind, sharp, and values-aligned humans. The strategy, culture, and incentive structures are everything I had hoped to build, and now get to be part of.

But even when you end up in a great place, the road there can feel like trying to run your company during the day while being interrogated by a team of lawyers at night. In a language you don’t speak. Using documents you didn’t know existed.

There are things I’d do differently if I ever had to go through it again. And since I’d prefer you not learn these the hard way, here’s the post I wish someone had handed me before I started.

1. Learn What Working Capital Really Is

You may think working capital is just “the money in the bank to make payroll.” I did. But in M&A, working capital becomes a financial and legal Rubik’s cube, and it directly impacts your final payout.

Here’s the short version as I understand it: your acquirer wants to make sure they’re buying a business that can operate normally on day one. So they’ll calculate how much short-term capital (cash, AR, prepaid expenses) needs to be in the business at closing, and they’ll negotiate that as a target.

That number is ESTIMATED. It’s also normalized and adjusted. And if you miss the target, you may be writing a check post-close.

Working capital trues up after the deal, and it gets shaped by your business model. Services companies, SaaS companies, project-based revenue, each one complicates the math. And everyone else at the table knows this well, but even in our deal our CFO understood subtleties that NO ONE else did. So you need to know more than the basics on this one.

Takeaway:

Working capital isn’t intuitive, but it’s important. Study it, model it, and don’t assume your gut will guide you right.

2. Trust, But Verify, Every Time

You’re surrounded by experts: bankers, lawyers, accountants. This is their job. They’ve done hundreds of these. But even experts miss things. Especially when they assume you’re a typical deal.

Like Simon Sinek always says, “Ask the stupid question”. Stop the meeting and go back to that thing on page 73.

In our deal, the biggest potential errors we caught came from small misunderstandings or unclear phrasing. We were almost too embarrassed to bring them up. But those awkward questions (asked by my amazing CTO) saved real money, and avoided some serious cleanup work later.

Takeaway:

If something doesn’t make sense, say so. You might be the last person who catches it. Also, have an amazing partner if possible who is more diligent than you are.

3. Track Due Diligence Like a Real Project

If your deal is mid-size or larger, you’ll probably have a junior banker acting as project manager. If it’s smaller, congrats, you are the project manager now.

You’ll be asked for contracts from 2018, explanations of deferred revenue, SOC 2 policies, lists of vendors, screenshots of your HR system, and a notarized blood sample from your head of finance.

I think that you should treat this like a set of software dev sprints: set up a simple spreadsheet, assign owners, and check in weekly. Otherwise you’ll lose track or lose your mind.

Takeaway:

Diligence is a second full-time job. Manage it like one.

4. M&A Lawyers Are Insane (In a Good Way)

They don’t seem to sleep. They respond to 1:00 a.m. emails. And they will happily work through weekends like it’s a sport.

This is great, because if you’re running a company during the day, you’ll be doing your deal work at night. Prepare for that rhythm. Use it. And then take them out to a really nice dinner when all is said and done.

Yes, the billable hours can be terrifying. But the best lawyers are worth it, and not just for paperwork. They’re your coaches in how to behave when the stakes are high.

Takeaway:

If you find a lawyer who texts back at 11:30 p.m. with bullet points, think of nicer and nicer places to take them for dinner.

5. Get Comfortable Being Talked About While You’re in the Room

There’s a moment (probably more than one) when someone on a call will say something like:

“Let’s review the comp structure for the founder if he dies.”

And you’ll be sitting right there.

At some point in the process, you stop being the protagonist and become a line item. That’s good. It means the business can live beyond you. But it can be weird. No one tells you how surreal it is to hear strangers talking about your salary, your severance, or what happens if you vanish.

Takeaway:

You’re not the business anymore. And that’s the goal.

6. Talk Less. Prep More. Don’t Negotiate

This might be the hardest lesson for most founders, especially if they’re used to wearing all the newest hats: you are not the negotiator.

You are not there to show how clever you are, or explain how smart your team was for choosing that customer billing cadence. You are there to answer questions, briefly, and let the professionals work.

The deal room is not your turf. Your team, your advisors, trained for this game. Hopefully you’re good at running a company… which is COMPLETELY FREAKING DIFFERENT.

Takeaway:

Channel your inner witness stand. Brief answers. Don’t ramble like I did. Let the pros handle the rest.

7. You Get to Watch Pros Be Amazing

One of the unexpected joys of going through this process was simply watching people who are really good at their jobs work together.

Bankers who know the exact number of turns in your industry. Lawyers who can dissect a 200-page agreement in an hour. The team on the other side of the table who’s been through five acquisitions and knows what to look for.

As operators, we’re often too deep in the weeds to step back and admire professional excellence. This process gives you that chance if you’re not too sleep-deprived to notice. Hopefully you can apply that feeling to your customers and clients. They should feel as deeply impressed by you if you’re doing things right.

Takeaway:

Sometimes, it’s okay to just watch and be impressed.

Final Thought

Selling your company is intense and humbling. It’ll test your patience, your understanding of finance, and your ability to stay quiet on Microsoft Teams calls (even when you are begging for a Google Meet or a Zoom). But if you’ve built something real, and you surround yourself with people who know what they’re doing, it can also be one of the most meaningful transitions of your life.

And if you’re lucky, you’ll end up where I did: not just with a great outcome, but with a future you’re excited to help build.

Just don’t forget to sleep after it closes.