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How AI Is Repricing Every Software Company

Vanta co-founder and CEO Christina Cacioppo returns to discuss what it takes to build an enduring software company in the age of AI. She and Patrick explore the “SaaSpocalypse,” why high-growth, high-margin software businesses are facing collapsing valuation multiples, and the dangers of charging customers for AI tokens. Christina shares how Vanta is reinventing its products around AI agents, why the talent wars have driven compensation for top employees up 10x, and what Silicon Valley is getting wrong about AI. They also discuss the future of cybersecurity, the extraordinary story behind Vanta's billion-dollar billboard war, and why rebuilding trust in technology may be the biggest opportunity of all. TIMESTAMPS 0:00 Intro 4:17 Surviving the SaaSpocalypse 9:40 The AI Pricing Trap 16:17 Rebuilding Software for AI 22:43 Silicon Valley's Talent Wars 31:57 What's Overhyped in AI 38:39 Security at Machine Speed 47:16 Reinventing Software 55:37 The Billboard War 60:38 Rebuilding Trust in Technology Presented by Ramp: https://ramp.com/invest Sponsored by Vanta, WorkOS, Rogo, and Ridgeline: https://www.vanta.com/invest https://workos.com/ https://rogo.ai/invest https://www.ridgelineapps.com/ ****** Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc

Patrick O'Shaughnessyhost

Oct 20, 20261h 4mWatch on YouTube ↗

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EPISODE INFO

Released: October 20, 2026
Duration: 1h 4m
Channel: Invest Like the Best
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

Vanta co-founder and CEO Christina Cacioppo returns to discuss what it takes to build an enduring software company in the age of AI. She and Patrick explore the “SaaSpocalypse,” why high-growth, high-margin software businesses are facing collapsing valuation multiples, and the dangers of charging customers for AI tokens. Christina shares how Vanta is reinventing its products around AI agents, why the talent wars have driven compensation for top employees up 10x, and what Silicon Valley is getting wrong about AI. They also discuss the future of cybersecurity, the extraordinary story behind Vanta's billion-dollar billboard war, and why rebuilding trust in technology may be the biggest opportunity of all. TIMESTAMPS 0:00 Intro 4:17 Surviving the SaaSpocalypse 9:40 The AI Pricing Trap 16:17 Rebuilding Software for AI 22:43 Silicon Valley's Talent Wars 31:57 What's Overhyped in AI 38:39 Security at Machine Speed 47:16 Reinventing Software 55:37 The Billboard War 60:38 Rebuilding Trust in Technology Presented by Ramp: https://ramp.com/invest Sponsored by Vanta, WorkOS, Rogo, and Ridgeline: https://www.vanta.com/invest https://workos.com/ https://rogo.ai/invest https://www.ridgelineapps.com/ ****** Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc

SPEAKERS

Patrick O'Shaughnessy
host
Host of the Invest Like The Best podcast.

EPISODE SUMMARY

In this episode of Invest Like the Best, featuring Patrick O'Shaughnessy, How AI Is Repricing Every Software Company explores why AI agents, pricing pressure, and trust are reshaping SaaS Christina describes Vanta’s evolution from SOC 2-centric compliance automation into a broader “trust” platform spanning audits, questionnaires, trust centers, and security products for a global customer base.

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