The {Closed} Session

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 sophistication, how machine learning solves NP-hard matching problems at Wall Street speed, and why GPU compute markets need combinatorial auctions to handle non-fungible infrastructure across latency zones and chip architectures.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 three systematic traps (setup, sales, and scale) that keep seven-figure CEOs trapped in operational bottlenecks. Plus, Charles shares his framework for achieving 50% recurring revenue and removing yourself from daily decision-making without breaking company momentum. This is an episode you don't want to miss.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 dynamics, and why the only defensible AI moats come from proprietary data loops.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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, and how inference costs are crushing margins for AI companies that don't understand their unit economics.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 combine probabilistic reasoning with deterministic execution, and apps that codify standard operating procedures into reusable automations.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 shares the "only you can say" principle that cuts through ChatGPT-generated sameness plaguing startup communications.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 sourcing creates self-reinforcing homogeneity, why impact metrics must align with venture-scale business outcomes, and Westbound's 50% profit-sharing model that attracts values-aligned founders in competitive rounds.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 solutions kill traditional left-to-right workflows, and why founders must quintuple their execution speed or face extinction in the compressed imagination-to-execution timeline.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 are driving hundreds of "Neo clouds" globally, and the specific multi-tenancy frameworks that transform expensive compute from sunk cost into competitive advantage.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 who think they're going public, how 30-minute operator calls save companies three months of execution time, and why the current AI gold rush mirrors the early cloud adoption cycle at Salesforce.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 layers that prevent vendor lock-in with legacy processors, and why focusing on non-technical power users beats pure developer experience when scaling payment infrastructure.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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-supervised versus fully automated, shares specific productivity metrics from oil rig safety inspections that prove ROI, and reveals why mortgage underwriting automation hits 98% straight-through processing while preserving customer relationships.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 account targeting, and why sustainable moats now depend on owning the point of work rather than systems of record.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 winning data network effects emerge from proprietary processing of public data, and shares the specific go-to-market playbook that works for enterprise AI sales cycles.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 "Boyle's law" principle means human capital will always find new problems to solve for clients.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 Tom go on to discuss why Middle Eastern sovereign wealth funds are building strategic energy advantages, and how nondeterministic AI systems require continuous sampling protocols.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 https://art19.com/privacy#do-not-sell-my-info.