"Am I wasting some of the best years of my life?"

Jan Sramek asked himself that question for years while working on one of the most audacious development projects in a generation: California Forever.

His plan: build an entirely new city on 100+ square miles of farmland in Solano County.

Not a housing development. Not a campus. A city, with schools, clinics, transit, and tens of thousands of homes in a state that's short 3 million of them.

His friends thought he'd lost it. Investors wouldn't return his calls. His wife was the only person who believed in what he was doing.

So he did something most founders wouldn't: he spent eight months trying to prove his own idea was wrong. He bought a 1958 government study off eBay, opened it up, and found a city planned for the exact same coordinates. Same location, to the mile.

He bet everything he had.

In this conversation, Jan and Connor get into what it actually feels like to build something this big when nobody believes in it yet. Jan talks about the difference between fascination and discipline, why knowing yourself matters more than knowing your market, and the moment the project almost broke him. They also cover unexpected ground: why house parties changed more minds than any ad campaign, and what competitive StarCraft taught him about getting things done.

CHAPTERS

Chapters

00:00:00 Building the next great American city
00:02:52 From Czech village to California visionary
00:04:11 The housing crisis nobody wants to solve
00:06:48 The leap from problem to solution
00:09:54 Proving it's not crazy — The 1958 validation
00:13:25 The inner skeptic and relentless optimism
00:21:17 Betting everything — The moment of no return
00:21:02 Silicon Valley's unique risk appetite
00:23:47 The overnight success that took ten years
00:32:53 Facing the backlash and building trust
00:47:28 House parties over TV ads — The unscalable solution
00:50:13 The big debate California needs to have
00:52:56 Starcraft and clicks per minute — The execution mindset
00:53:50 The future — Building begins

IS THIS WORKING?!

What if the most interesting thing about work isn't what we do—but what it does to us?

Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway.

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