EP 85: From Burnout to Breakout: How Jennifer Tsai Bootstrapped Shoott.com to $10M After Raising $2.7M
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EP 85: From Burnout to Breakout: How Jennifer Tsai Bootstrapped Shoott.com to $10M After Raising $2.7M
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What happens when you raise $2.7M... then realize you never want to raise again?
Jennifer Tsai, founder and CEO of Shoott.com, built a profitable photography marketplace from the ground up; surviving death threats from creatives, a brutal CAC spike post-iOS14, and the chaos of marketplace economics. In this episode of Fundraising Demystified, we dive into how she scaled to $10M in revenue, hit breakeven, and is now facing the “what’s next” moment many founders dream of, or dread.
Whether you're building a two-sided marketplace, wrestling with capital strategy, or wondering how to survive without more VC cash, this one's for you.
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In this episode, you'll learn:
00:00 – Death Threats, Disruption & The Origin Story of Shoott.com
05:45 – Why Creatives Hated Us And How We Won Them Over
12:08 – From $80K to $10M: The Fundraising + Growth Playbook
17:52 – How We Hit Profitability (And 20x’d It)
21:26 – Cash Flow Roulette: Paying Creators Before Clients Pay Us
22:57 – The $300K Mistake That Nearly Sank Us
25:57 – Should You Raise, Sell, or Stay the Course?
27:32 – The Brutal Truth About Valuations in Today’s Market
30:38 – Founders: Before You Build a Marketplace, Watch This