$500M, 5 Exits, 0 Failures: Jody Glidden's Playbook No One Talks About

Listen to the full episode where Jody Glidden shares how he built five companies with zero failures—and why going deep in a vertical changed everything for him.

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Jody Glidden has exited five companies. Zero failures.

When I asked him what's worked across all five, I expected him to talk about product or timing or team.

He talked about restraint.

The Pattern Behind Five Exits

Every company Jody has built follows the same playbook: pick one vertical, go deeper than anyone else, and don't expand until you've won.

He told me he won't go broad until he's raised $30-40M. Before that? Find a corner and own it completely.

It sounds almost too simple. But when you look at his track record, it's hard to argue with.

Why Most Founders Go Broad (And Why It Hurts Them)

I've felt the pull myself. You're pitching investors, and you want the TAM slide to look massive. You see opportunities in adjacent markets and think "why leave money on the table?"

Jody sees it differently.

When you're early and underfunded, going broad invites better-funded competitors to crush you on every front. You're fighting 12 battles with resources for one.

Going deep means you can build something defensible before anyone notices. You become the only option for that specific customer. You create switching costs. You learn the workflow better than anyone.

Then—and only then—you expand with a proven playbook.

The Math That Made It Click For Me

Jody put it simply: until you've raised serious money, you can't afford to compete everywhere.

But if you own one vertical completely? You can expand from a position of strength instead of desperation.

He's done this five times now. Same pattern. Same outcome.

IntroHive started with professional services firms. Just the Big Four. He went from 100 seats at PWC to 1,000 to 10,000 to 93 countries. Only then did he expand to other verticals.

By the time competitors noticed, he'd already won.

What This Looks Like In Practice

Jody's approach comes down to a few questions:

Who is the narrowest customer I can serve better than anyone else?

What would it take to become the only real option for them?

How do I make it painful for them to switch?

Answer those three questions. Ignore everything else until you've won that corner.

The temptation is always to go wider. More customers, more markets, more features.

Jody's whole career is a case study in resisting that temptation.

What I Took Away

Five exits. Zero failures. The same playbook every time.

Restraint sounds boring. But Jody's track record is a pretty good argument for it.

Go deep. Stay deep. Expand only when you've won.

Leo

P.S. We also talked about why he's never lasted more than a year after getting acquired, the year he wasted building something BlackBerry was about to give away for free, and how he picks angel investments (100-200x returns on his winners). Worth a listen.