Justin Smith-Lorenzetti, Founder and Managing Director, Intact Private Capital, shares his journey from leading innovation initiatives within Intact Insurance to helping build a global investment platform managing more than $1.6 billion in assets. Drawing on lessons from investments across insurtech, mobility, AI, and financial services, he explains how Intact approaches startup and LP investing. Justin also offers practical advice for founders and investors, arguing that focus and conviction matter more than ever in today's AI-driven world.

David Zhou, co-founder of The Side Letter and host of Superclusters, shares lessons from his journey as a founder, venture investor, LP, and educator. He explains how sophisticated limited partners evaluate venture funds, why consistent decision-making frameworks matter, and how emerging managers can stand out in an increasingly crowded market. David discusses common mistakes new LPs make, the metrics that matter when evaluating venture performance, and why successful investors develop discipline around both entering and exiting investments. He also shares practical advice for fund managers seeking LP support, emphasizing the importance of understanding investor motivations before ever making a pitch.

Christina Quinn, General Partner at SSC Venture Partners, shares practical lessons from investing in first-time founders and supporting Boston College entrepreneurs through venture funding and accelerator programs. She explains how SSC Venture Partners combines community, mentorship, and early-stage capital to help founders navigate the difficult early years of company building. Christina also discusses the qualities she consistently looks for in entrepreneurs, including adaptability, resilience, initiative, and self-awareness.

Ian Sandler, COO of Insight Partners and co-founder of Riley’s Way Foundation, engages in a deeply personal and wide-ranging conversation on leadership, venture capital, and building meaningful impact. Ian reflects on his unconventional career path, his philosophy on building organizations, and how a personal tragedy shaped his mission to empower the next generation of kind leaders. He also shares practical advice for founders and young leaders on dreaming big, understanding themselves, and building networks that matter.

Gilad Shai, Managing Director at BMI Capital International, reveals the harsh realities and hidden opportunities in the InsurTech ecosystem. From launching InsurTech LA with 10 people in 2015 to watching billion-dollar valuations evaporate 90% post-IPO, Gilad shares unfiltered insights on why most InsurTech startups are stuck in "purgatory" and what it really takes to succeed in insurance innovation.

Debjit Mukerji, Partner at NGP Capital, explains why deep tech’s defining moment has finally arrived. Drawing on a thesis-driven approach, he shares how he evaluates companies at the intersection where “atoms meet bits”, backing founders building in the physical world. Debjit breaks down the convergence of three powerful forces—labor shortages, generative AI’s expansion into industrial use cases, and faster hardware development cycles—that are unlocking a new era of opportunity for physical technology companies.

Danielle Strachman and Michael Gibson, Founders and General Partners at the 1517 Fund, discuss their unconventional approach to venture capital. The firm backs ambitious young founders, many of whom choose to leave college early to pursue breakthrough ideas. Drawing on their experience building the Thiel Fellowship, Danielle and Michael explain how working closely with hundreds of young innovators shaped their belief in character driven investing. They share how they identify talent before traditional signals appear and why curiosity, conviction, and “hyper fluency” matter more than credentials.

Jessica Karr, Founder and Managing Partner at Coyote Ventures, shares how she backs AI-driven startups focused on improving health access, outcomes, and equity. Drawing from her six years at Impossible Foods, where she helped build a product from prototype to global phenomenon, Jessica explains how she brings a product innovator's lens to healthcare's most overlooked problems: women's health, racial disparities, rural access, and aging care. Jessica demonstrates why solving for equity isn't just morally right; it's economically smart through better outcomes and cost savings. She also discusses how her Health Equity Innovator Summit has become the convergence point where founders, health systems, payers, and policymakers forge the partnerships that turn healthcare's biggest gaps into its biggest opportunities.

Kapil Surlaker, VP of Engineering, Data and AI Infrastructure at LinkedIn, joins guest host Bhaskar Ghosh for a technical and thoughtful discussion on how AI is reshaping enterprise. Kapil shares how LinkedIn built strong data foundations over more than a decade, and how that foundation enabled generative and agentic AI use cases. He reflects on building Espresso, a distributed database created out of necessity, and explains why he would not build it again today. The conversation explores AI infrastructure, model flexibility, privacy guardrails, and operational responsibility. His message to leaders is clear. Reinvent yourself continuously, or risk becoming irrelevant.

Aman Verjee, Founder and General Partner at Practical Venture Capital, shares his view of how venture capital has evolved over the past two decades and why secondary markets now play a critical role in the ecosystem. Drawing from his time at PayPal, eBay, and Sonos, Aman explains how companies today stay private far longer than they used to, what that means for early investors and employees, and how thoughtfully structured secondary transactions can reduce friction and misalignment on the cap table. He also challenges popular narratives around tech bubbles, walking through historical examples to explain why today’s AI-driven market looks fundamentally different.