The Most Expensive Education Gap in Startups

Founders are an amazing bunch. They learn quickly, ride the highs and lows, and manage thousands of decisions a day.

But the biggest gap I see is when it comes time to exit.

As investors, we have endless playbooks on how to hire engineers, how to design products, and how to raise capital. There are accelerators, courses, and podcasts dedicated to the “Starting.”

But when it comes to the “Exiting” – the single most important financial transaction of a founder’s life – we leave them to figure it out on the fly. It is the most expensive education gap in the industry.

Specifically, I wish we taught these four things that seem to remain a “Black Box”:

1. When to start the process

My biggest challenge is getting founders to plan for an exit years before it happens. Too often, founders only think about selling when they have <6 months of cash left. That is a sale out of fear. The best outcomes happen when you build relationships while things are going well, long before you “have” to sell.

2. How to Select a Banker

Most founders default to the “brand name” firms. They don’t realize that in M&A, the individual matters 10x more than the logo on the door. You need to ask: Is this person actually connected to the buyers? Is my transaction size meaningful to them, or am I just filler for their pipeline?

3. How to Manage the Banker

Once hired, many founders abdicate control. They think, “The banker handles the sale.” This is dangerous. I wish we taught founders that a banker is a tool, not a savior. You have to drive the bus. Bankers are highly transactional (which is useful!), but the founder has to bring the relationship and the human side to close the deal.

4. Corp Dev is a Relationship, Not a Department

The best exits I’ve seen happened between people who had known each other for years. It was the coffee at the conference in 2023 that led to the acquisition in 2025. We need to teach founders that you don’t “email Corp Dev” when you’re ready; you nurture those relationships when you have nothing to sell.

The tragedy is that M&A is a test you only get to take once. There is no practice round. You are learning the rules of poker while sitting at the high-stakes table.

It’s something I’m working on communicating better to my founders all along the way – not just at the end.