I've sold three companies as CEO or senior executive over the last 15 years: Hopscotch, a sports and entertainment mobile app advertising platform, in 2019; Gehry Technologies, an AEC collaboration company with a celebrity founder, in 2013; and Central Desktop, a Monday.com/Box competitor, in 2012. I'm now working on a fourth here at Incentify.

Each of those transactions taught me something the previous one hadn't. Looking back, almost everything I thought I "learned" the first time was really just luck that I retroactively dressed up as wisdom, and I only knew the difference once the next deal either confirmed it or didn't.

For any founder, operator, or PE-backed CEO who can see a transaction sitting somewhere in the next 18 months, here are the three things I'd pay real money to have known earlier in my career.

Lesson 1The exit is built 24 months before the term sheet

When a banker finally calls or a strategic shows up with interest, the instinct is to start reacting. Tighten up the deck, get the data room organized, sharpen the narrative, run the process. Most CEOs I know treat this as exit preparation. It isn't. That's exit theater.

The actual preparation is everything you did, or didn't do, two years before that phone rang. Whether you let your finance function stay scrappy or made it institutional. Whether your top 10 customers are concentrated or spread out. Whether your contracts are month-to-month or multi-year. Whether your gross margin holds up at scale or is propped up by services revenue you'd rather not talk about. Whether your second layer of leadership can actually run the company without you in the room.

I learned this watching it play out from inside two very different transactions. At Gehry Technologies, we had a recognizable name attached to the founder, real technology, and enterprise customers in 10 offices across the Americas, Europe, the Middle East, and Asia. But the operating discipline was still catching up to the brand. When Trimble came in, the deal got done, and got done well, but the sale process surfaced every place we hadn't fully professionalized. You can feel the difference in real time, in a data room, when the answer to a buyer's question is "let me get back to you" versus "here's the report."

At Hopscotch, we'd started the cleanup three years before the sale. Multi-tenant architecture in place, signed enterprise contracts, a real CFO, real ops. When the strategic conversations started, we didn't have to prepare. We just had to present.

If you wouldn't pass diligence today, you aren't six months from an exit. You're 24.

Lesson 2Your second product is what makes you a platform. Your first product is what gets you to the meeting.

Single-product companies sell at a discount. Platforms sell at a premium. That gap is one of the most consistent things I've seen across every transaction I've been part of, and it's also one of the most consistently misunderstood by the founders inside those companies.

At Hopscotch, we spent the first few years building the SaaS platform. Mobile apps for sports teams, college athletics programs, venues, live events. Real product, real customers, real revenue. That was the company. And it would have sold. But what made it sell well was the second business we built on top of it. Once we had 120 apps deployed across some of the most engaged mobile audiences in the country, we had something nobody else had: a first-party view into how sports and live-event fans actually behaved on their phones. We turned that into an advertising and sponsorship layer — a second product, a second P&L, a second reason for an acquirer to care. Suddenly we weren't a mobile app company. We were a platform with two ways to make money.

The same dynamic is playing out at Incentify. The core SaaS platform is the first product. But we recently launched a proprietary LLM purpose-built for the credits and incentives space, and it's already doing for the second chapter what the ad network did for Hopscotch — adding a layer that changes what kind of asset the company is.

If you want to be acquired as a platform — and you want to be acquired as a platform, because the multiples are categorically different — start building the second product before anyone is asking you to.

Lesson 3The best deal is rarely the last deal. Know when to take it.

This is the one that cost me the most to learn, and it's the lesson I'd most want a first-time CEO to internalize before they ever sit down at the negotiating table.

At Hopscotch, we had an offer on the table from an Italian-based tech company that was a good deal. Not perfect, because no deal is ever perfect, but clean, well-structured, from a credible buyer, at a price that fairly reflected what we'd built. My gut said take it. The board wanted more.

I understood the argument. The business was performing, the trajectory was real, and pushing for a better number was completely defensible. So we went back, asked for more, and waited. Then the market started to shift. Buyer appetite cooled. The comparable transactions that had supported our valuation got repriced. Strategic acquirers pulled back on M&A. By the time we eventually closed, we sold for less than the offer we'd originally walked away from. Meaningfully less.

Markets close faster than they open. The window when buyers are willing to pay top-of-cycle multiples is always shorter than anyone inside it thinks. "More" carries a cost that doesn't show up anywhere on the spreadsheet — every month you spend negotiating is a month the market has to move against you, and that risk compounds.

A good deal in your hand is worth a great deal that might not close. That isn't an argument for taking the first thing that walks through the door. It's an argument for recognizing, with real clarity, when an offer is genuinely good, and not letting the pursuit of better become the enemy of done.

The meta-lesson

If I had to compress all three of these into one idea, it'd be this: building a sellable company is a fundamentally different discipline than building a successful one.

There are plenty of great businesses that are basically unsellable. There are plenty of mediocre businesses that sell for a fortune. The difference is almost never the product, or the market, or even the team. The difference is whether the people running it understood, early on, that they were actually building two things in parallel: an operating business, and an asset. The operating business is what your customers see. The asset is what your eventual buyer sees. They're related, but they aren't the same thing.

I made it the first time. I think I avoided it the second time. The third one taught me there's always another layer of nuance I haven't seen yet. The fourth, when it comes, will teach me something new again. Honestly that's the part of this work I'm most looking forward to.