Why Most Founders Fail at Series B
(And How Tilt Didn't)
What happens after the big exit? In this episode, Ben Chiang unpacks this journey from scaling a Uber China to 50M weekly users, to getting acquired by Snap, to starting over again in AI, and what he’s learned about timing, luck, and what actually matters. We talk founder identity, raising with leverage, finding joy in the chaos, and why knowing what you want is the real superpower.
Check out:
- 00:00: From Zero to 50 Million Weekly Rides: Uber China’s Blitzscale Playbook
- 02:48: Why Market Fit Is Make or Break
- 06:07: Timing, Relationships & the Hidden Rules of Fundraising
- 08:58: Forma’s Acquisition by Snap: Behind the Deal
- 11:57: Luck, Credit, and the Realities of Startup Success
- 15:00: Negotiating from Leverage vs. Desperation
- 26:13: Founders vs. Investors: What Changes After an Exit
- 28:08: QSBS: The Most Underrated Tax Benefit in Startups
- 30:27: How Stock Market Volatility Affects Founders
- 32:11: Leaving Snap: Rediscovering Purpose
- 33:43: The Messy Reality of Building and Marketing AI Products
- 37:14: Fundraising Now vs. Then: What’s Actually Changed?
- 40:57: Herd Mentality and the Modern VC Landscape
- 44:07: What It Takes to Enjoy the Founder Journey
- 47:00: Final Advice: Know What You Want
ABOUT BEN CHIANG
Ben Chiang is a veteran operator and founder best known for launching Uber in China and later founding Forma, a startup acquired by Snap. His experience spans scaling platforms in hypercompetitive markets, navigating complex acquisitions, and now building across multiple AI content ventures.
Get in touch with Ben:
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