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November 6, 2024 • 51min
I failed 22 times... then I built a $2.5B Company | Christina Cacioppo from Vanta
My First Million
Christina Cacioppo, founder and CEO of Vanta (valued at $2.45B), shares her journey from quitting her job at Union Square Ventures to teaching herself to code, launching multiple failed projects, and eventually building Vanta into a major compliance automation platform. The conversation covers managing founder psychology, maintaining high standards, and lessons learned along the way.
I failed 22 times... then I built a $2.5B Company | Christina Cacioppo from Vanta
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Key Takeaways
- Betting on yourself requires managing your psychology - Figure out what makes you feel centered and don't give those things up, even when busy
- Success often comes after multiple iterations and failures - Christina built 35+ projects before Vanta, viewing them as necessary "bad art" to eventually create something great
- Customer validation is critical - Only count real commitments ("can you do this for me now/next week"), not vague future interest
- Keep standards high but sustainable - Create an environment where people want to get better every day versus enforcing arbitrary metrics
- Progress equals happiness - Focus on continuous improvement rather than fixed goalposts
Introduction
Christina Cacioppo, founder and CEO of Vanta (valued at $2.45B), shares her journey from quitting her job at Union Square Ventures to teaching herself to code, launching multiple failed projects, and eventually building Vanta into a major compliance automation platform. The conversation covers managing founder psychology, maintaining high standards, and lessons learned along the way.
Topics Discussed
The Journey from USV to Self-Employment (0:00)
Christina left her job at Union Square Ventures despite warnings about giving up the powerful "USV.com" email domain. She saved her bonus to self-fund a period of learning to code and building projects.
- Created structure by treating it like a job - got dressed and went to an office space daily
- Focused on learning rather than immediately trying to build a startup
- Faced skepticism from others who questioned leaving a prestigious position
The Art of Making "Bad Art" (8:30)
Christina embraced the concept that most creative work serves to teach you how to make the small fraction that truly succeeds.
- "The function of the overwhelming majority of your artwork is simply to teach you how to make the small fraction of your artwork that soars" - from Art & Fear
- Built multiple projects knowing they were learning experiences rather than businesses
- Shifted perspective from expecting immediate success to viewing iteration as necessary
Managing Your Psychology (22:30)
Christina emphasizes the importance of maintaining psychological well-being while pursuing entrepreneurial goals.
- Core practices for staying centered:
- Running 3-4 times per week for mental clarity
- Reading consistently as a grounding activity
- Maintaining routines that make you feel like yourself
- Finding ways to stay motivated despite setbacks and self-doubt
How to Pick Ideas to Chase (27:47)
Christina shares her approach to identifying and validating business opportunities.
- Key criteria:
- Pick something you want to learn about
- Talk to potential customers about their problems
- Focus on commercial viability from the start
- Look for problems in spaces you understand or want to understand deeply
The Real Origin of Vanta (29:03)
The story behind how Vanta actually started, beginning with Christina's experience at Dropbox.
- Initial validation:
- Started with spreadsheets rather than coding
- Reached out to YC companies for feedback
- Focused on solving real compliance problems
- Learned from previous projects to prioritize commercial viability
Building a Flywheel (31:00)
Christina discusses how Vanta gained initial traction and built momentum.
- Growth strategies that worked:
- Outbound emails to YC companies
- Building word-of-mouth in founder communities
- Podcast advertising (surprisingly effective)
- Tried multiple approaches simultaneously to see what worked
Controversial Opinions (36:06)
Christina shares some contrarian views on common startup advice.
- On consistency: Actually underrated in business operations
- On high standards: Can create positive, infectious environment when implemented correctly
- On moving goalposts: Not necessarily bad if you enjoy the work itself
Pushing Past the No (40:49)
Discussion of maintaining high standards and pushing boundaries.
- Creating a culture of excellence:
- Setting expectations above industry standards
- Building an environment where people want to improve
- Focusing on progress rather than fixed metrics
Negotiation and Fundraising (46:17)
Christina's approach to negotiations, particularly during fundraising.
- Key principles:
- Standing firm when confident in position
- Willingness to wait rather than flinch
- Being deeply proud of achievements and communicating that effectively
- Raised Series A after reaching $10M ARR, creating significant leverage
Conclusion
Christina Cacioppo's journey with Vanta demonstrates the importance of persistence, continuous learning, and maintaining high standards while managing your psychology. Her experience shows that success often comes through iteration and failure, but staying focused on progress and enjoying the work itself can lead to breakthrough results. The key is to balance ambitious goals with sustainable practices and to validate ideas thoroughly before scaling them.