Podcast Episodes

How operator scars build defensible AI startups

Episode 58

Most operators fail as investors because they can't scale their expertise beyond one-on-one advice calls. Leyla D. Seka, former Salesforce EVP who built the multi-billion dollar AppExchange ecosystem…

Published on 3 hours ago

Behind Finix’s self‑serve payment platform

Episode 57

Most payment startups treat compliance like a checkbox instead of survival strategy. Richie Serna, CEO of Finix, sold his previous payments company to Stripe and now competes directly against them, w…

Published on 1 week, 6 days ago

How AI accelerates enterprise software development

Episode 56

Most enterprise AI pilots fail because companies treat agent development like legacy software projects. Woodson Martin, CEO of OutSystems and former Salesforce executive who led the Krux acquisition,…

Published on 4 weeks ago

How AI is rewriting startup growth playbooks

Episode 55

Most AI pilots fail because founders are retrofitting old playbooks instead of rebuilding revenue architecture. Mark Roberge, founding CRO at HubSpot who scaled from $0 to $100M revenue, breaks down …

Published on 1 month, 1 week ago

Growth lessons from consumer tech operator‑investor

Episode 54

Most vertical AI companies fail because they're building features, not businesses. Rachel ten Brink, GP at Red Bike Capital and former Scentbird co-founder (scaled to 500K+ subscribers, $29M raised),…

Published on 2 months ago

Is AI in Investment Banking a Replacement or Revolution?

Episode 53

Most AI adoption in finance is just automation theater—real transformation requires rethinking entire workflows. George Lee, former CTO and M&A head at Goldman Sachs, explains why AI won't replace ba…

Published on 2 months, 2 weeks ago

How AI Transforms Different Corners of Earth

Episode 52

Most AI investment flows to infrastructure while founders ignore energy constraints that will determine who survives. George Lee, Co-Head of Goldman Sachs Global Institute, breaks down the bottleneck…

Published on 2 months, 2 weeks ago

Common threads through 25 years of VC investing

Episode 51

AI startups fail because founders obsess over models, not company building. Harrison Miller is a former VP/GM from Amazon.com’s early years, and former MD of Summit Partners, which over 40+ years has…

Published on 2 months, 4 weeks ago

The Brothers Chavez In Conversation: Tom & Marty Chavez on AI, Investing, + More

Episode 50

Tom Chavez, Founding General Partner at super{set}, in conversation with his brother - R. Martin Chavez, Partner and Vice Chairman, Sixth Street,  Board Member at Google, and former CFO of Goldman Sa…

Published on 1 year, 4 months ago

super{set} Celebrates First Exit: LiveRamp Acquires Habu for $200M

Episode 49

super{set} Celebrates First Exit: LiveRamp to Acquire Data Collaboration Software Startup Habu for $200M!

Joining Tom and Vivek in the studio today are Habu co-founders Matt Kilmartin (CEO) and Mike M…

Published on 1 year, 6 months ago