What I learnt selling my first two SaaS companies - 1/2

And not becoming anywhere close to filthy rich in the process

They call it an exit

The last few months have been quite a ride, especially the end of last year.

I founded and bootstrapped two software companies. One was an accounting software combined with accounting services — one always feeding the other. The second was a payment platform, something that surveys would probably describe as “a Stripe for the Colombian market.” That was the idea, at least. Execution is always more nuanced than the pitch. In this very specific case, much more nuanced.

Well, I (we, in the case of the payment platform) managed to sell both businesses in the last few months. And even though the title sounds arrogant, this is not a story about becoming a millionaire. I didn’t.

I just think that bootstrapping up to exit two times taught me many things, hence I will write (some of) them here.

Boredom compounds

Both exits taught me how to make a company “acquirable,” or what buyers say they want versus what they actually care about. It also forced me to confront a few uncomfortable facts.

Disclaimer to the reader, this article will probably go all over the place and lack structure. I am just sharing learnings and feelings en vrac. Sorry if it’s unreadable.

First, I feel there is some flavour of failure in selling a company. Yes, failure. It’s a harsh word, but I mean it.

If you build your life’s work, you don’t sell it. Ideally, you give it to your kids or sell it before you pass away. The company you sell is, in some way, the one you did not want to spend your life building. That sounds grandiose, but I felt it quite viscerally.

Maybe I am too romantic, in the literary sense of the word (I am) — even though it goes beyond the scope of this blog — but I cannot achieve anything without deep, irrational passion, and building FinTech brought nothing close to inner fulfilment. I felt some euphoria sometimes, terror most times, boredom often, but never deep passion. I am sharing this because I think the hardest part of negotiation was hiding my profound boredom with the FinTech world¹ and my hurry to leave this world.

Almost a year and a half before the exits, I knew I was going to sell. Not because it was the optimal financial decision but because I was simply getting bored and uninspired. I know LinkedIn crowd celebrate acquisitions and company-flipping like it’s some Graal. I allowed myself a celebratory post, I confess.

Yet I totally disagree on this, the best things in life comes with a deep sense of purpose, and one does not cash out their purpose, they experience it and endlessly discover it. Do not get me wrong, I’m glad I founded both those businesses, and concluded those two transactions along my co-founder in one of them. I just think Entrepreneurship is much more than that.

That’s the first real lesson. Boredom is lethal in entrepreneurship. Once it settles in your daily, your sense of purpose drops. Your energy drops. Your standards drop. You are still operating the company, but mentally you’ve already left. It’s not dramatic if you are operating on VC’s funds and you pay yourself a fat salary, it’s slightly more stressful if your business pay the bills.

This is how I decided to exit.

Now, I’ll tell you how I effectively succeeded.

Incentives.. again

When you sell a company, you are selling two things. You are selling the obvious — the product, the software, the team, the execution, the cash flow. But more importantly, you are selling a future to the buyer.

I’ve been willing to sell the accounting software company for at least two and a half years. I was looking for acquirers through private banks, activating my network here and there. It was a constant cycle of ups and downs. Sometimes I was enthusiastic, sometimes quite depressed. Every conversation felt like it might lead somewhere, and most of them didn’t.

Here, I strongly suggest to contact potential buyers on a regular basis, and use a cold approach. It was, in my case, surprisingly effective, as every single approach I had was primarily the result of some outbound work. I know it may sound weird, but no one is going to buy your average, not-so-great business if you don’t tell them it’s for sale. I contacted those who — in my not so humble opinion — would benefit from adding my software to their stack. Every single time, they would at least take the call. Every, single, time.

When you sell a product — be it Burrata Pizza or software subscriptions — incentives are much simpler to understand. The buyer either sees value or doesn’t. They compare alternatives. They decide. You sell the value of your product and focus on the immediate benefits they will get. When someone buys your company, incentives are even more crucial and more hidden.

In my case, the main asset was never cash flow. It was positive if nothing extraordinary. Barely enough to pay myself a decent salary and live in a relatively affordable country. There wasn’t explosive growth. There wasn’t venture hype. It was steady and it was bound to stay this way. I understood from the first potential buyer I could not orient the talks toward the financial statements, otherwise I would be doomed.

Now, most people don’t have extraordinary companies. Most companies are normal. Mine wasn’t extraordinary either. It wasn’t bad. It was stable. It had positive cash flow and decent technology. In some ways, the tech was much above average. But today, many people have good software. Especially right now. So “good” somewhere is not enough to be attractive. Your value depends on the urgency of the buyer.

You only need one

In the first encounters with potential acquirers, I allowed the conversation to drift away from my value to my weaknesses. I did not focus enough on the potential future I am selling them. I believe I let go higher bidders because of this mistake. The beginning of the conversation should have set the tone around my strengths, not around what made my business average.

Acquirers will disclose chunks of valuable information here and there and it’s vital to catch them. It’s the same for every relationship, for that matter. People disclose information about themselves and their incentives, with their actions primarily, and in their language, and you should not let it slip away.

Like for everything in life: the more someone talks, the more they promise, the less serious and reliable they usually are. The serious acquirers don’t over-explain and don’t try to seduce you with projections and duffle bags full of cash. They protect information because they know it’s leverage and if they don’t like something, they say it early. Serious people know the weight of a promise, and how difficult it is to fulfil just one, let alone several.

Only one thing stayed constant: I knew I didn’t want to keep doing this with my life. I think it was a mismatch from the very beginning. Not a catastrophic one. The company wasn’t failing. The technology was decent, even above average in my opinion. It helped people. Still, something was off. On a more personal note, I believe it’s important to close cycles, especially those filled with negative energy. Selling the company was closing a cycle. Later, deciding to going to live to a new city was part of the same move. I guess it matters especially at a relatively young age when circumstances allow you to be completely free.

After some aborted negotiations, I understood that what my best potential acquirers really seek was time. They simply did not want to build accounting software themselves. They lacked the technical ability or the patience. Buying was faster and less risky than developing internally. Some wanted a team from day one because they were incompetent to hire developers and engineers. That was something I initially underestimated in early negotiations with other potential buyers. I spoke with at least eight. Some were real. Many were not.

If you buy the software, you buy the years it would take to rebuild it. Even in the time of AI, you cannot just spin up a compliant accounting system overnight, especially in a country with complex tax and regulatory structures. It would take at least a year to build something robust and operational. Another year to fully proof-test it. That was the asset: time gained. The ability to operate from day one instead of spending years developing. Once I understood that, I knew what I could defend in negotiations.

If someone wanted me to defend the audience, the marketing, the projected growth, the five-year expansion story — I would be fucked. I would have to sell projections. “In five years we could expand, margins could increase, new markets could open.” But honestly, I didn’t even fully believe that myself. I wanted to fuck off desperately and would not even be here to see those flamboyant dreams come true, so why would I sell that story to someone else? I did not even care enough myself about it in the first place.

If I cannot commit to that vision personally, I won’t package it and sell it as certainty. I preferred defending something tangible such as the technology and the time it saves.

How it went

When talking to a buyer, you need a number in your head. A number you won’t go below. A number that lets you sleep at night. Even if the upside could be higher. Why? Because once you decide to exit, your focus is divided. You are negotiating while still running the company. If you are bored — as I was — you want it done. Not at any cost, but quickly. Without a floor in mind, you waste time in negotiations that were doomed from the beginning.

Another strange phenomenon: nothing happens for months. Then suddenly buyers appear in waves. The first one shows up, and then somehow you enter a cycle. Every few weeks, someone else appears. Most of the early ones disappear. The final buyer is the one you least expected.

Now, about making a company acquirable is, in theory, simple. In practice, it requires discipline most founders avoid. You have to think of your company as a system, not as an extension of yourself. If it needs you constantly, it is not acquirable. If operations collapse when you step away, it is not acquirable. If code, reviews, customer relationships, and key decisions live only in your head, it is not acquirable.

The ideal system should function without you. Especially now, in a world where software, automation, and AI allow for extraordinary leverage, there is no excuse for ultra-dependence.

When you market software, you focus on features, UX, pricing, immediate benefits. When someone buys your company, they look at completely different variables: cost structure, operational clarity, team stability, documentation, recurring revenue, independence from the founder. What you polish publicly is rarely what closes the deal. What you quietly did in private over the years is what suddenly becomes valuable. Acquisition is when you get paid for what you practiced in silence over the years.

More next week, or next month, or never.

1. More on that never, I never want to come back to FinTech.