We Turned $5M Into $419M Buying Cashflow Businesses ft. Jeremy G…
About This Episode
Jeremy Giffon, the first employee at Tiny, details how the investment firm scaled $5 million into a $500 million portfolio by acquiring cash-flow businesses like Dribbble. The episode explores early deal-making tactics, the psychology of negotiation, and why qualitative analysis often beats complex financial modeling.
Episode Description
Show Notes
- 0:00Humble beginnings at Tiny Capital
- 4:40Tiny’s first acquisition
- 8:1750X return on Dribbble
- 10:14Skip the cash flow statements
- 11:57How to spot the opportunity
- 14:00Chris’s superpower
- 16:20Stomaching aggressively low offers
- 17:46Make an offer and stop talking
- 19:36It’s not you vs. them
- 22:06"What would need to be true to make this deal?"
- 23:03How to crush the cold email
- 25:15Worst deal -- ignored red flags, lost everything
- 27:00Best deal: Mealime (25X return)
- 29:16Weirdest deal ($36.00 acquisition)
Check Out Sam's Stuff
Key Takeaways
Reframe negotiations from 'me vs. you' to 'us vs. the problem' to align with the seller and uncover non-monetary incentives.
Utilize silence after making an offer; hitting mute or staying quiet often forces the other party to negotiate against themselves due to discomfort.
Focus on 'no-brainer' deals where the purchase price is so low that day-one levers like price increases or cost reductions make success inevitable without complex modeling.