The Sure Shot Entrepreneur

Dan Borok, Co-Founder and Managing Partner of NVP Capital, discusses opportunities for founders building innovative solutions in under-digitized critical industries, including manufacturing, logistics, transportation, energy, and healthcare. Drawing on his experience at Google and in venture capital, Dan explains why NVP backs mission-driven founders tackling complex industry problems. He shares h...

Pavel Prata, founder of Murph Capital, shares his unconventional journey from Belarus to Silicon Valley and across the venture ecosystem—from startup fundraising and venture investing to investor relations and allocating capital to emerging fund managers. Pavel shares the first-principles framework he uses to evaluate emerging managers: understand whether venture is a natural extension of their jo...

Rohini Chakravarthy, Managing Partner at NewBuild Venture Capital, shares her journey from engineering in Silicon Valley to more than two decades of venture investing at Intel Capital, NEA and NGP Capital. She explains why she and her partners created NewBuild around the transformation of the physical enterprise—from procurement and manufacturing to logistics and delivery. Rohini also explains wha...

Isabel Bescos, Partner at Entrepreneurs First, shares how EF identifies exceptional founders before they have a company, co-founder, product, or even a business idea. She explains why EF considers itself a talent investor, what it means to invest in individuals at a stage even earlier than pre-seed, and the characteristics she looks for when evaluating potential founders. Isabel discusses will to...

Sudarshan Sridharan, General Partner of SF1, shares his journey from building founder communities and operating startups to launching an early-stage venture capital firm focused on AI-native companies. He explains how he evaluates founders, why competence, integrity, and ambition matter more than polished pitches, and how artificial intelligence is reshaping the markets attracting venture capital....

Amir Kabir, Founder and Managing Partner at Overlook Ventures, discusses his journey from entrepreneur to venture capitalist and explains why he founded Overlook Ventures to invest at the earliest stages of company building. He shares his investment philosophy around founder quality, intellectual honesty, unique market insight, and the emerging opportunity around AI, autonomy, and risk infrastruct...

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....

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 met...

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 dis...

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...

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 innovat...

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,...

Danielle Strachman and Michael Gibson, Founders and General Partners at the 1517 Fund, discuss their unconventional approach to venture capital. The firm backs ambitious 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 shape...

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, raci...

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 ou...

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 h...

Jonathan Crystal, Managing Partner at Crystal Venture Partners, talks about investing in early-stage AI-driven insurtech companies. After leading his family's insurance brokerage to a successful exit, Jonathan launched his $33M fund when he realized AI was the catalyst insurance had been waiting for. He explains why entrepreneurship means "dooming yourself to years of terror," and why the best inv...

Amias Gerety, Partner at QED Investors, brings an unconventional perspective to venture capital shaped by his eight years at the US Treasury Department during the financial crisis. A mechanical thinker, Amias applies an essentialist approach to understanding how businesses work. He explains why QED looks for companies that triple every six months at Series A, how inverted AI creates new opportunit...

Steve Kim, Partner at Verdis Investment Management, shares his unique take on venture capital investment through a data-driven, diversified portfolio strategy. With a focus on early-stage investments and emerging managers, Steve discusses why diversification is key to optimizing venture returns and building enduring funds. He offers insights from his transition from technology leadership to invest...

Stephen Wemple, Principal at Spero Ventures, shares how he backs mission-driven founders building enduring companies aligned with purpose and profit. From investing in hardware startups like Telo Trucks to backing social impact ventures such as Juno, Stephen explains why conviction and alignment between founders and investors matter more than ever. He reflects on his journey from Fulbright Fellow...

Itamar Novick, founder and General Partner at Recursive Ventures, explains how a repeat-founder’s playbook shapes better early-stage investing. Itamar draws on 25 years of startup experience (including executive roles at Gigya and Life360) to describe the firm’s disciplined pre-seed focus, how he evaluates founders and markets, and why AI applications built on first-party data will create the next...

Adam Draper, Founder and Managing Director at Boost VC, shares stories of his family’s pivotal role in shaping Silicon Valley, from his grandfather’s pioneering work at Sutter Hill Ventures to his father’s global expansion of Draper Associates. Building on that legacy, Adam created Boost VC to back founders tackling endeavors of consequence — companies so bold they’re often dismissed as “too risky...

Maryam Haque, Founding Executive Director of Venture Forward, discusses how she is helping to open doors to venture capital for people from all backgrounds. She traces her journey from Mississippi to Silicon Valley and highlights the structural barriers that kept venture capital concentrated for decades. Maryam offers a grounded view of the current market dynamics, the growing importance of educat...

Tim Guleri, Managing Partner at Sierra Ventures, reflects on 25 years in venture capital and his journey from Chandigarh to Silicon Valley. He shares how hands-on experience as a founder shapes his investing philosophy, why early-stage VCs must guide founders toward long-term fundamentals, and why raising too much capital too soon can hurt a company. Tim explains Sierra’s disciplined approach to p...

Bhaskar Ghosh, Partner at 8VC, reflects on his journey from Calcutta to Silicon Valley, spanning influential roles at Oracle, Yahoo, LinkedIn, and NerdWallet before moving into venture capital. Now a leader at 8VC, BG introduces his “geometry framework” (persona, product, budget) for enterprise startups, shares insights on the opportunities in generative AI and data infrastructure, and talks about...