Podcast
Real conversations. Real business. Real growth.
Every week, we tackle one meaningful business topic—from entrepreneurship and leadership to AI, capital, marketing, and scaling. Startup Membership and above unlock every episode and the complete podcast archive.
Legacy Isn't an Exit Ramp
Jason argues that most founders confuse legacy with liquidity — and his co-host isn't buying the distinction until he backs it up with names, numbers, and a solar deal that fell apart.
8 min · 8/13/2026
Stop Being the Best Employee in Your Own Company
Jason argues that the hardest promotion you'll ever get is the one from operator to owner — and his co-host isn't buying half of it. A messy, specific conversation about letting go, hiring people who'll ignore you, and why being 'needed' is a trap.
8 min · 8/3/2026
You're Probably Pricing It Wrong (And Cheap)
Jason and Maya go a few rounds on how to price your first product — why 'cost plus margin' is a trap, when to charge more than feels comfortable, and the pizza-shop test.
9 min · 7/27/2026
Your "Business" Loses Money? That's a Hobby With a Logo
Jason and his co-host fight about the one financial line that separates a real company from an expensive hobby — and why most founders won't admit which side they're on.
8 min · 7/20/2026
When to Hire Your First Employee (or Don't)
Jason argues most founders hire too early to feel less lonely. His co-host isn't buying it. A real fight about when a second set of hands actually pays off.
8 min · 7/13/2026
AI as Plumbing, Not a Party Trick
Jason argues that most companies are bolting AI on as a shiny feature when it should be load-bearing infrastructure. His co-host isn't buying the hype and makes him prove it with real numbers.
8 min · 7/7/2026
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