I spent the better part of two decades as an investment banker advising people on how to sell their companies.

By the time Payapps was acquired by Autodesk, I’d been on both sides of the table: the banker running processes, and the founder inside them.

Founders now ask me about this all the time. When is the right time to sell? How do you get ready for a process? And how do I choose a banker to sell a business like mine?

Selling a company is not easy.

Doing it at the opportune time, is an even harder trick to pull off.

In banking, deals fall over all the time. So my motto is that “the better I prepare, the luckier I get”. Because luck in a large transaction is a combination of things aligning. It's timing, readiness, and relationships you built long before you needed them.

It's better to sell a year too early than a year too late.

When you have a strong growth profile, the market pays you a premium multiple for it. So when you’re a fast growing business, the risk isn't that your business stops growing, it's that the steepness of the growth curve starts to flatten. The moment a buyer senses that, the multiple comes off, and multiple compression can cost you far more than another year of revenue will ever add back.

At Payapps I watched this play out with our own numbers. Of course, absolute percentage growth naturally comes down as the revenue base gets bigger — that's fine, and any sophisticated buyer expects it.

The big signal to watch is the dollar value of new growth. In our early years, in a major market, new dollars went something like one, two, three, four. The next year it was four and a bit.

The market was still there, but the question every investor asked was around how would we go from four to six to eight to ten in new dollars each year? When the next dollar of net new growth starts getting harder, you may be crossing the golden window Rubicon.

This isn't a series A or series B concern. If you've just raised, your only job is growth, and it’s likely you shouldn't be thinking about an exit at all.

For most founders it doesn't become a real concern until you're perhaps five plus years in. The point is to be honest with yourself about where you sit on the curve, and to know that the best time to sell is while the story is still accelerating, not after everyone can see it slowing.

If you’re extremely high conviction that you have a huge market opportunity to grow into, and you continue to accelerate into it, keep going.

I look at the current environment and it’s clear a proportion of the AI market are having a moment. So my advice would be, if you’re an AI company and the multiples around you look insane, don’t assume that will last.

We’ve already seen this in SaaS: businesses that once traded at mid-teens multiples now trade at mid-to-high single digits on the same fundamentals. If you’ve got conviction within your company while external multiples are low, hold on till multiples rebound.

If someone puts a genuinely great offer in front of you, an offer that stands out from a multiple perspective from the market, the disciplined move may be to take it rather than bet that next year looks like this one.

The most common mistake I see is founders treating preparation as something that begins when they receive an approach from a potential buyer. By then you're already behind. So how do you stay prepared?

At a minimum, keep a living corporate presentation for rapid fundraising or a sales process. This can be a deck you iterate on continuously that you can use for a raise or a sale at any time.

The best founders also stand up a data room and keep it reasonably current. When a strategic buyer knocks on your door unannounced to take a serious look around, the volume of information they want is far greater than anything a VC asked for in a fundraise. Founders who haven't done the homework lose weeks to months assembling it under pressure, and delay is where deals die.

Most founders underestimate the intensity of a sales process. The diligence, the volume of material required, and the Q&A... potential buyers will come back at you with hundreds of questions and turning them around quickly keeps momentum alive.

Preparation is the cheapest leverage you have in a process.

It helps to split the universe of buyers in two, because they behave very differently.

Think about the motivations for the buyer and try understanding why they want to acquire you. A fund might see in you an opportunity to own a meaningful stake in a growing company. A strategic buyer might see in you an opportunity to bring your product and customers into their own engine. Or, perhaps, you plug a gap in their offering or open a new market up for them, or maybe you’re a big competitor they want to take out.

Strategic buyers, whether competitors or larger players in your sector, tend to do more work and take longer. They're usually slower-moving in a deal process, and they’ll dig deep into your tech stack and product, not just the numbers.

Funds churn through financial information fast. I’ve seen a growth-equity fund ask for an Excel dump of revenue by month, by region, by customer, and come back with a fifty-page report on your business inside a week. It’s incredible what funds built for acquisitions can churn out.

The practical reality is you can't run the same playbook with both for the optimum outcome. A strategic buyer needs more time, more of your product and engineering team, and a story about where you fit in their world. On the other hand, a fund needs clean, granular numbers and fast answers. And don't treat "funds" as one thing either — a VC writing a cheque, a growth-equity firm taking a real stake with the rights that come with it, and a PE buyer are three different conversations.

This is the one I’d most encourage you to act on now, because it takes the longest. It can be as simple as grabbing a coffee with teams when you’re in their town.

With Payapps, we’d been circling the eventual acquirer for a while. We’d had early discussions, explored a product partnership that didn’t really amount to much. In short, we were doing the dance where each side feels the other out.

None of it looked like a sale at the time. But when the moment came, I could call them, say we had an offer from another party, and they moved fast, because they already understood our business and our people. That head start on the relationship was enormously valuable.

Direct competitors are different.

You’re not going to share much, and you shouldn’t. But you know what they say, keep your friends close and your enemies closer.

If you think someone might be a buyer one day, make the effort to grab a coffee or dinner when you’re in the same city, even once, and get to know them on a personal level. A competitor who has at least met you and broadly gets what you do is a better counterparty than a stranger. Plus, plenty of business leaders want to know if they can work with you.

A lot of founders from tech instinctively don't want to deal with bankers. I understand the reflex, but they earn their place in two ways.

First, they help you navigate a universe that is impossibly wide. Once you get to a certain scale, every week some fund analyst is emailing you for a catch-up as they’re interested in your company and answering them one by one is a terrible use of your time. The efficient move is to let a bank put you in front of all of them at once.

One of the most valuable things large banks do for their clients is host investor conferences where you can present your business to a group of growth investors. In my case, after a 15 minute talk on stage to the group I held a mini roadshow of sorts with perhaps twenty fifteen-minute meetings in a day.

Five or six funds came out of it saying they loved the business and asking how to pre-empt a process. We had IFM Investors as a significant minority investor and funds knew they would likely look to exit over the next 12-24 months.

Second, banks help you decide where it's worth engaging at all. You can't run a process with everyone — proper diligence is so intense that you need narrow the universe of parties. Three or four serious parties is about all you can sustain before something falls apart, so part of the banker's job is narrowing the field to the buyers who matter.

Bankers are generally paid on success. If you’re a smaller outcome for them, advisers may want a retainer. It’s important you understand the structure before you sign and incentives are aligned.

There's no magic answer, and I'd distrust anyone who offered one. But in my experience, the founders who do the best on the way out have three things in common: they were thoughtful about timing, they were prepared, and they'd built real relationships with the people they ended up across the table from.

Do that work early, while you don't need it, and you'll find you get a lot luckier when it counts.