/The {Closed} Session

The {Closed} Session

Building a company from scratch is soul-sucking and mind-numbingly hard - but it’s the best thing ever. We know this because we’ve built a couple ourselves - and we’re building a lot more right now. We’ve made a lot of money for our employees, our shareholders, ourselves - we’re proud of that - and that’s why we want to talk about how it’s done. Join us - Tom Chavez and Vivek Vaidya - in The Closed Session, where we reveal all the joys and sorrows of company building. From the guttermost to the uttermost, we’re not going to hold back.

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Building a Billion-Dollar AI Startup

Dec 15, 2025·—

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Most AI 'innovation' is just workflow automation disguised as intelligence. Benjamin Shapiro, founder of I Hear Everything and creator of AI-powered podcast production systems, talks with Tom Chavez about the brutal...

How to build a global AI infrastructure company

Dec 1, 2025·—

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Most enterprises burn millions on idle GPUs while developers wait weeks for access. Haseeb Budhani, CEO of Rafay Systems, built a global GPU orchestration platform after exits at Soha Systems (acquired by Akamai) and...

How operator scars build defensible AI startups

Nov 17, 2025·—

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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, explains how...

Behind Finix’s self‑serve payment platform

Nov 3, 2025·—

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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, winning 60% of...

How AI accelerates enterprise software development

Oct 20, 2025·—

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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, explains why...

How AI is rewriting startup growth playbooks

Oct 6, 2025·—

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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 how AI compresses...

Growth lessons from consumer tech operator‑investor

Sep 15, 2025·—

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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), breaks down how to...

Is AI in Investment Banking a Replacement or Revolution?

Sep 3, 2025·—

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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 bankers but will...

How AI Transforms Different Corners of Earth

Sep 2, 2025·—

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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 bottlenecks choking AI...

Common threads through 25 years of VC investing

Aug 19, 2025·—

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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 invested $40B in...

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

Jun 25, 2024·—

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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 Sachs. Tom and Marty...

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

Apr 26, 2024·—

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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 Moreau (COO) to give...

super{set} Fund II: Intensifying Our Serial Focus on Data+AI Company Building

Mar 28, 2024·—

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Announcing super{set} Fund II! The world has tilted in our favor. We’ve been building companies in the data+AI space for 25 years, mostly while it was niche and nerdy. With the AI revolution fully upon us, we’re...

Creating a People-First Performance Culture for Startups

Feb 7, 2024·—

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Talent and career development in startups is typically nonexistent - so at super{set}, we're changing that. While a startup’s opportunities for rapid growth and trial by fire are incredible, we believe startup employees...

Rachel Gollub on Engineering, Entrepreneurship & Leading Healthcare AI

Dec 20, 2023·—

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Rachel Gollub is a distinguished engineer, programmer, and entrepreneur with a storied career in Silicon Valley: she started her career as part of the founding team behind the Java programming language and ended it as...

How OpenAI Can Build an Ethical and Effective Board

Dec 1, 2023·—

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Everyone’s talking about what went down at OpenAI - but what does it mean for ethical and responsible AI, and what are the lessons for entrepreneurs on startup board governance? With the abrupt dismissal of CEO Sam...

What Consumers Think of AI and Their Privacy

Nov 28, 2023·—

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Everyone’s talking about AI - so The Ethical Tech Project decided to listen. Joining forces with programmatic privacy and data+AI governance platform Ketch, The Ethical Tech Project surveyed a representative sample of...

Spotlight Series: Lindsey Meyl, Co-founder of RevAmp

Nov 20, 2023·—

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The {Closed} Session Spotlight Series showcases a different co-founder from the super{set} portfolio in every episode. Today's guest is Lindsey Meyl, Co-founder at RevAmp (rev-amp.ai), a "Datadog for RevOps" platform...

Ringside Tales from Serial Startup Champion Omar Tawakol

Nov 9, 2023·—

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Like Rocky Balboa and Apollo Creed, the fiercest competitors can sometimes become friends. Omar Tawakol is a prime example. As the founder and CEO of BlueKai, he went head-to-head with Tom, Vivek, and the 'Krux mafia'...

Philosophy, Data, and AI Ethics with NYT Best-selling Author + Data Scientist Seth Stephens-Davidowitz

Oct 25, 2023·—

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How does Google search data reveal hidden human truths and behaviors? What philosophical challenges arise when interpreting big data? In what ways does data reflect societal biases and preconceived notions? What's the...

Spotlight Series: Andrew Marshak, Co-founder of Headlamp Health

Oct 18, 2023·—

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Headlamp makes it easy for clinicians and their patients to access their universal medical records, while also providing advanced AI tools to support more personalized health insights and decision-making. Lean more...

Marketing in the Age of AI with Rex Briggs

Oct 11, 2023·—

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Marketing has always been about connection, but what happens when AI becomes the mediator? With vast strides in AI-driven campaigns, how do marketers ensure they remain true to their brand and their audience? Who...

Spotlight Series: Gal Vered, Co-founder of Checksum.ai

Sep 22, 2023·—

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Checksum automatically generates and maintains end-to-end tests based on user sessions so you can move fast without breaking things. Learn more about Checksum at checksum.ai. Gal Vered's LinkedIn...

Harvard Computer Scientist James Mickens on The Ethical Tech Project

Sep 6, 2023·—

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Are we walking a tightrope with AI, jeopardizing humanity's ethical core? Is AI more than just algorithms, acting as a mirror to our moral values? And when machine learning grapples with ethical dilemmas, who ultimately...

AI Hot Takes: Deepfakes, The Big Stakes, and What to Make

Aug 9, 2023·—

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Is AI our salvation or is it going to kill us all? Tom and Vivek roam widely on others’ takes about artificial intelligence, adding their insight and experience to the mix. Along the way they consider Descartes, Ray...