22 failed ideas - before finding one huge hit ($2.5B) | Christin…
About This Episode
Vanta founder Christina Cacioppo shares her journey from Union Square Ventures to building a $2.5 billion security and compliance platform. She details her two-year period of 'self-induced poverty' where she built over 20 failed projects while learning to code, eventually discovering the power of testing business ideas with spreadsheets before writing a single line of code.
Episode Description
Show Notes
- 0:00Stumblehustling into USV
- 4:36Betting on the left side of your email address
- 8:30The art of fear
- 11:47Making bad art
- 13:30The marshmallow test
- 17:26Startup advice to beware of
- 18:16The idea for Vanta
- 21:00The only question that matters
- 22:30Managing your mind
- 27:47How to pick an idea to chase
- 29:03The real origin of Vanta
- 31:00Building a flywheel
- 36:06Controversial opinions
- 40:49Pushing past the no
- 46:17Not flinching during negotiations
Links
Check Out Shaan's Stuff
Check Out Sam's Stuff
Key Takeaways
Front-load the possibility of failure by testing the riskiest assumptions (like demand) with low-fidelity tools like Excel spreadsheets before investing in engineering.
Embrace the 'Pottery Class' philosophy: the volume of your 'bad art' (failed projects) is exactly what teaches you how to create the small fraction of work that eventually soars.
Manage founder psychology by identifying and maintaining non-negotiable personal habits—like running or reading—that keep you grounded and feeling like your best self regardless of business outcomes.