The {Closed} Session

Most healthcare AI founders pitch the technology instead of patient outcomes. Colin Lawlor, founder of Sleep.ai with 15 years in sleep science and 250+ clinical studies, explains why sleep data requires specialized infrastructure beyond generic LLMs. He reveals how Sleep.ai's billion-hour proprietary dataset creates defensible moats through wearable normalization models, intervention efficacy mapp...

Most founders treat culture like an afterthought until it breaks. George Schlossnagle, founder of Message Systems (sold to MessageBird for $600M), explains why culture debt accumulates faster than technical debt and destroys scaling companies from within. He breaks down the "culture branching" phenomenon that happens around 100 employees, shares frameworks for detecting early warning signs like "t...

Most enterprise AI delivers generic responses when you need role-specific intelligence. Peter Day, General Partner at super{set} with a PhD in machine learning and 8 years leading product at Quantcast, breaks down why agentic personalization creates unbreachable competitive moats. He reveals the architectural patterns for building software that learns individual preferences in real-time, explains...

Most enterprise AI failures aren't model problems—they're data architecture problems. Vivek Vaidya, serial entrepreneur with 25+ years building enterprise software and current CTO/Co-founder of super{set}, explains why vector databases alone can't solve enterprise AI and why knowledge graphs are foundational for production systems. He breaks down the critical difference between augmented intellige...

Most financial markets still run on one-to-one matching when optimization engines could unlock trillions. Kelly Littlepage co-founded OneChronos after exits to major financial institutions, building the fastest-growing US equities market processing $20 billion daily using Nobel Prize-winning combinatorial auction theory. He breaks down why capital markets lagged behind ad markets in auction sophis...

Most founders think scaling means hiring more people, but 66% of Inc. 5000 companies fail within eight years because growth without systems is just expensive chaos. Charles Gaudet, founder of Predictable Profits and "CEO Whisperer" who's unlocked $100M+ in client revenue, breaks down why founder-dependent businesses hit inevitable walls regardless of funding or talent acquisition. He reveals the t...

Most AI fundraising advice is performative gibberish disconnected from capital reality. Arjun Dev Arora, managing partner at Format One, breaks down why founders absorbing social media narratives about billion-dollar pre-seed rounds are setting themselves up for failure.  Arjun reveals why traditional VC support models collapse post-check, how technical founders systematically mismanage board...

Most founders pitch the wrong metrics while $200 billion flows into AI startups annually. Vijay Rajendran, author of #1 Amazon bestseller "The Funding Framework" and venture builder at gAI Ventures, breaks down why fundraising feels harder despite abundant capital. He reveals the four-part system that shifts founders from pitching to partnering, why retention metrics will expose vanity user counts...

Most enterprise AI pilots die in the sandbox trap. Miguel Milano, President & CRO at Salesforce with $40B in revenue operations, explains why 95% of AI implementations fail without enterprise-grade data infrastructure and deterministic workflows. He breaks down Salesforce's three-pillar strategy for scaling AI beyond proof-of-concept: data foundations with metadata context, agentic layers that...

Most founders think storytelling is fluff that distracts from product metrics. Terry Szuplat, Obama's longest-serving speechwriter who crafted eight years of presidential addresses, reveals why narrative craft is your last defensible moat in the AI age. He breaks down the three-part framework that structured 3,000 White House speeches, explains why vulnerability beats data in investor pitches, and...

Most VCs chase momentum while missing systematic market dislocations worth billions. Sean Mendy, co-founding partner at Westbound Equity Partners, built a $125M fund targeting the 97% funding gap for underrepresented founders. He didn't do this out of charity, but as alpha generation through expanded deal flow and objective evaluation frameworks. The conversation reveals how network-driven sourcin...

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 realities of building defensible AI companies versus riding the hype cycle.  Tom and Ben dissect why proprietary data virtuosity trumps LLM wrappers, how outcome-oriented AI solut...

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 brings deep infrastructure expertise to solving the $100B GPU waste crisis. He reveals why 93% of Fortune 500 companies achieve sub-85% GPU utilization, how sovereign AI requirements...

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 Operator Collective structures 200+ operators as LPs with carry to systematically deploy operational knowledge across portfolio companies. She reveals why she never invests in founders w...

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 head-to-head deals. In this conversation with Tom Chavez, Richie breaks down why payments requires 95% feature completeness before product-market fit clicks, how to build abstraction laye...

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 deterministic platforms beat "vibe coding" for production deployments. He breaks down agentic workflow architecture that gives enterprises control over which processes stay human-supervis...

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 traditional sales cycles and transforms go-to-market execution. He reveals why selling time will jump from 25% to 75% of a rep's week, how AI enables real-time ICP refinement and acco...

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 build defensible vertical AI that survives the regulatory gauntlet. She reveals her operator's test for distinguishing product businesses from services wrappers, explains how winnin...

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 compress deal cycle times from weeks to days. He breaks down how junior talent using AI companions can eliminate rote tasks while expanding analytical surface area, and why the "Boyl...

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 deployment from silicon to grid capacity. George reveals flexible demand management frameworks that could unlock 75-125 gigawatts of slack capacity, eliminating energy bottlenecks. He and...

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 more than 550 tech companies. He explains why execution, not algorithms, determines survival. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at h...

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 discuss their brief stint as roommates, their brotherly relationship, and R. Martin's experiences as an investor, entrepreneur, and corporate leader. Listen for insights on startups,...

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 the full story behind how Habu was conceived, built out, scaled, and sold. Habu is a leader in the data collaboration category with innovative data clean room technology. Habu enab...

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 thrilled to announce that super{set} has closed a $90 million second fund to invest in companies at inception. Since launching our first fund, super{set} has founded, funded and scaled 16...

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 can still benefit from intentional mentorship and development. No - it's not about bringing in professional coaches who lack hands-on company-building expertise. And no, it's more...