The Final Update

Dennis Crowley on why he keeps redrawing the map instead of starting over. The founder of Dodgeball, Foursquare, and Hopscotch explains what it actually means to be an entrepreneur—and why being early and being wrong can look exactly the same.

Dennis Crowley read Harry Potter and decided someone needed to build the Marauder's Map for New York, a way to see where your friends are in real life. Twenty-five years and three companies later, he's still chasing that idea: Dodgeball (texting your location, pre-iPhone, bought and slowly killed by Google), Foursquare (sixty million users, then Instagram changed what people wanted from th...

The final chapter of Manuel Saez's story. After his company shut down, he had to answer a question: who am I without it? He calls the experience a blessing and he also still gets angry about it. Both are true. We talk about what's left when the company that defined you is gone, and how writing became his way through it.

There are two kinds of founders, and they handle the same outcomes completely differently. Manuel breaks down why some people can close the chapter on a company and walk away unchanged, while others stay tied to a "dead man walking" long after it should have ended. The difference comes down to where your identity sits, and whether you can hold onto purpose without losing yourself in it.

After exiting his company sooner than expected, Manuel Saez faced a question many founders avoid: What now? Instead of rushing into the next startup, product, or opportunity, he paused. What emerged from that pause was a question he now asks before making any meaningful decision: "What's my vibe?" In this episode, Manuel shares why the emotional state behind a decision matters just a...

Manuel Saez built an electric bike company that was working. Subscribers in New York City, real demand, a product people wanted. Then COVID hit. Twelve months of inventory sat stuck in a shipping container while the debt piled up. Without inventory or investor support, he had to exit earlier than he wanted to. He calls it landing the plane. Not an explosion — dents and scratches, but intact. In th...

Being first sounds like an advantage but it's usually not. The first mover proves something is possible. The company behind them pays less to do it better. Amy Heckerling knew this when she made Clueless. She took Pride and Prejudice's skeleton and dropped it into 1995 Beverly Hills. Jane Austen's framework but a completely new movie. This is also Bob's story. He built RunTime in t...

Most founders dread the investor conversation when things aren't working. Bob didn't. Here's why. In Chapter 2 of The Final Update, we look at what separates a managed exit from a burned bridge — and it's not the outcome. It's whether you walked in with a plan. This episode covers the psychology of all-or-nothing founder thinking, why merging your identity with your company's result is a trap, and...

There are three versions of any company: who you think you are, what you're actually shipping, and what your customers think you are. For RunTime, those three things stopped lining up, not all at once, but one custom project at a time. Bob walks through the consulting trap and the question most founders never think to ask before it's too late

Bob was running a business that was cash flow positive-ish. Not thriving but surviving. And when you're surviving, the case for walking away becomes harder. Stay and deal with the fallout, or keep going because you're still can? That question kept him stuck longer than he wants to admit. In this episode, he talks through the decision he wishes he'd made sooner.

Bob was building long before any of these frameworks existed. Back at the birth of Silicon Alley, before Y Combinator, before the playbooks, before there was even a community of founders who'd been through it. He had to figure it out the hard way. And he stayed five years longer than he should have.

There's a moment most founders face: when you know the company isn't working. What do you do? Kevin Weatherman had seen startups fail from the outside. As an angel investor in New York, he'd backed over 150 companies, six of which became unicorns. He understood the patterns and had given the advice. Then he built Lever Health, a men's weight loss company that came out of his own ex...