Cheeky Pint
Cheeky Pint
Stripe
Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
57 minutes Posted Mar 31, 2026 at 12:00 pm.
Christina Cacioppo, founder and CEO of Vanta, joins the pub to discuss building the future of agentic trust. She explains why compliance has a “vitamin vs painkiller” dynamic, the drama behind their famous 101-billboard campaign, and why she believes "market sizing is bullshit." They cover the tension between vibe coding and rigorous security, how Vanta is using agents to generate UI, and why the best founders are relentless truth-seekers.Timestamps
Vanta
How compliance works
Breaches
Stripe Tax
AI and compliance
Go-to-market
0:00
57:27
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Show notes
Christina Cacioppo, founder and CEO of Vanta, joins the pub to discuss building the future of agentic trust. She explains why compliance has a “vitamin vs painkiller” dynamic, the drama behind their famous 101-billboard campaign, and why she believes "market sizing is bullshit." They cover the tension between vibe coding and rigorous security, how Vanta is using agents to generate UI, and why the best founders are relentless truth-seekers.Timestamps(00:00:17) Vanta(00:12:30) How compliance works(00:15:06) Breaches(00:23:52) Stripe Tax(00:24:43) AI and compliance(00:44:50) Go-to-market(00:47:22) Lessons from USV