The Sure Shot Entrepreneur

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 journey, look for genuine conviction, identify their unique superpower, and keep the strategy simple. He also explains why the best VCs focus on serving founders and how LPs can determine whether an investor adds value beyond capital.

In this ep...

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 what NewBuild looks for at the earliest stages, expounding on the difference between proof of value and proof of market.

In this episode, you'll learn:
[01:43] How Rohini went from engineering in Bangalore and Silicon Valley to venture capital, in...

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 power, personal exceptionalism, followership, resilience, and bias to action as key founder traits. She explains why great founders matter more than great ideas at the earliest stage, how founders can prepare before approaching EF, why building...

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. Throughout the conversation, Sudarshan offers practical advice on earning investor trust, building meaningful relationships, and creating long-term value as both a founder and an investor.

In this episode, you'll learn:

[03:10] How Sudarshan built founder communities, started companies, and launched SF1 while...

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 infrastructure. Throughout the conversation, Amir offers practical advice for founders on validating problems, building venture-scale businesses, and standing out in an increasingly crowded AI landscape.

In this episode, you'll learn:

[02:15] How Amir's journey from entrepreneur to venture capitalist shaped the...

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.

In this episode, you'll learn:

[02:08] How Justin accidentally became a venture capitalist

[06:55] How Intact Private Capital invests from...

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...

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.

In this episode, you'll learn:

[01:59] Christina Quinn’s unconventional path into venture capital

[05:36] How SSC Venture Partners supports Boston College founders

[10:30] Why SSC invests at...

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.

In this episode:

[00:58] Ian Sandler’s background and upbringing

[03:59] From law to “wimpy entrepreneur”

[06:05]  Building...

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.

In this episode, you'll learn:

[01:13] Building the InsurTech LA community

[05:26] The evolution of InsurTech over the past decade

[10:50] Are we early or late in InsurTech?

[15:01] Why innovation in insurance is harder than it looks

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.

In this episode, you'll learn:

[05:28] Why venture capital?

[07:40] Inside NGP Capital’s deep tech focus

[11:05] Why...

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 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.

In this episode, you'll learn:

[01:03] Danielle Strachman and Michael Gibs...

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...

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 ma...

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 investments happen when founders identify problems before revenue models. With investments in companies like Bright Harbor, which helps families navigate disaster recovery, Jonathan explains how domain expertise enables conviction at day one—when there's no product, just a founder with an au...

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 opportunities in financial services, and why the best advice for founders remains timeless: build something people want and charge more than it costs to make. With insights on the AI bubble, the application layer renaissance, and why saying no 99...

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 investments, his commitment to backing emerging managers, and how this strategy benefits both LPs and founders in the long run.

In this episode, you’ll learn:

[01:18] Steve's background and transition into venture capital

[06:15] Using data to drive decisions in ve...

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 in Vietnam to venture capitalist in Silicon Valley, the lessons he’s learned from working with founders, and how smaller, concentrated funds like Spero bring focus and depth back to early-stage investing.

In this episode, you’ll learn:

[0...

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 wave of meaningful enterprise value. He shares concrete advice on what founders should share with VCs before/during the first meeting, how Recursive filters opportunities, what makes an investable TAM, and the common reasons he passes after initial interest.

In...

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” by traditional investors. He explains how pre-seed investing differs from later-stage venture capital and why he loves supporting technically ambitious founders in frontier industries, crypto, space, and deep tech. He also reflects on how curiosity, not...

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 education and mentorship for emerging managers, and how programs like VC University and the GP Masterclass help build a stronger, more inclusive industry.

In this episode, you’ll learn:
[01:55] From Mississippi to Silicon Valley: Maryam’s unexpected path...

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 partnering with entrepreneurs, the power of unique customer insight, and his hope that America preserves its structural advantage in entrepreneurship.

In this episode, you’ll learn:
[02:10] From Chandigarh to Silicon Valley: Tim’s path to ventur...

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 why managing uncertainty is the core skill in zero-to-one journeys. He also emphasizes intentional networking, the long-term nature of venture relationships, and his deep passion for music through his support for Ragas Live.

In this episode, you’ll learn:
...

Zach Noorani, Partner at Foundation Capital, shares hard-earned insights from more than a decade in venture capital. He talks about why the most important question investors wrestle with is differentiation, why authentic conversations with founders matter more than polished pitches, and how the best founders demonstrate velocity of learning. Zach also reflects on the evolving nature of venture—how the industry has become more professionalized, what excites him about the new wave of innovation, and why empathy and due process matter in society as much as in business.

In this episode, you’ll learn:

[01:40] From Sale...

Jacques Benkoski, General Partner at US Venture Partners, shares lessons from decades of experience as an operator, CEO, and VC. He challenges common startup myths and offers a framework for market entry that emphasizes strategy over luck. Jacques explains why focus—not speed—is the key to building category leadership, and why the venture ecosystem has become noisier, faster, and harder to navigate. He also opens up about the psychological toll of startup leadership and why founders need thought partners, not just capital.

In this episode, you’ll learn:

[01:00] From Belgium to Israel to Silicon Valley...

Amit Garg, co-founder and managing partner at Tau Ventures, shares how he backs startups at the intersection of healthcare, enterprise, and automation.. Drawing from his experiences as an operator, VC, and nonprofit founder, Amit offers a pragmatic and deeply thoughtful perspective on what makes a venture-backable company, and why doing the right thing can (and should) drive valuation.

In this episode, you’ll learn:

[04:40] Why Amit believes _“VC is one of the most intellectually fulfilling jobs in the world”_—and how it blends empathy and long-term conviction

[11:40] Betting on uncomfortable timing: Tau backed Iterativ...

Dave McClure, founder of Practical Venture Capital and co-founder of 500 Startups, dives deep into the growing role of secondaries in venture capital. Dave explains how today’s longer startup cycles and liquidity droughts have created opportunities (and confusion) around secondary markets. He breaks down what secondaries actually are, how Practical VC operates, and key trends shaking up the system. With his trademark candor, Dave also shares hard truths for both founders and VCs navigating this next chapter of private markets.

In this episode, you’ll learn:

[03:55] Dave’s journey to becoming an investor
[06:30] The early...

Brian Frank, the founder and general partner at FTW Ventures, shares why he left his founder career to invest in startups solving real-world problems starting with the global food system. He explores the climate risks, supply chain fragility, and health challenges driving the need for innovation in food and agriculture. From AI and biotech to automation, Brian highlights where the biggest opportunities lie. He also offers candid advice for founders navigating slow-moving, regulation-heavy industries and calls for a more collaborative, mission-aligned approach to venture capital.

In this episode, you’ll learn:

[03:35] How startup success as a...

Geoff Ralston, founder of SAIF (Safe Artificial Intelligence Fund), and former President of Y Combinator, shares his vision for building a safer AI future. Geoff discusses the risks and promise of AI as a force beyond traditional tools, posing AI as a set of entities that will reshape the way we work, live, and relate to each other. He talks about biosafety, interpretability, and misinformation as key focus areas for innovation. Geoff also shares advice for founders navigating this fast-evolving landscape and reflects on how thoughtful investment today can shape the future of humanity.

In this episode...

Nadav Eylath, founder and managing partner of at.inc, shares his philosophy of early-stage investing rooted in trust, long-term thinking, and technical rigor. Nadav talks about backing founders at the very inception of their startup journey—sometimes even before they’ve left their jobs. He explains how asking questions like “What kind of company will this be in 30 years?” leads to deeper conviction and better partnerships. Nadav also shares his views on why venture capital needs to evolve and how a flexible, founder-first approach can reshape the industry.

In this episode, you’ll learn:

[01:49] From building t...

Tomoko Ishikura, Managing Partner at Kicker Ventures, shares her unique perspective on investing in the future of healthcare. She talks about building a venture firm rooted in empathy, humility, and measurable impact. Tomoko explains how Kicker Ventures seeks science-backed innovations that move the heart, not just the market, and why strong communities are vital for startup success. She offers candid advice for founders on articulating impact, leaning into community support, and navigating a healthcare landscape that's increasingly collaborative.

In this episode, you’ll learn:

[02:00] Why Silicon Valley’s "uncertainty and possibility" drew Tomoko from Japan

Mahesh Ram, serial entrepreneur and former Head of AI at Zoom, shares his journey from building pioneering companies in education and AI to helping launch FUNDA, a vibrant founder-to-founder community. He discusses the evolution of AI-first startups, lessons from working closely with Zoom founder Eric Yuan, and what it takes to build enduring tech companies today. Mahesh offers real-world advice on how founders can navigate the rapidly changing startup landscape, with a deep focus on customer obsession, rapid product iteration, and embedding technology into core workflows.

##In this episode, you’ll learn:

[01:50] How Mahesh went fr...

Andrew Cleland, Chief Investment Officer at Techstars, shares how the world’s leading accelerator invests in early-stage startups. He breaks down what makes a great founder, how Techstars selects startups from tens of thousands of applicants, and why a strong technical differentiator is crucial. Andrew reveals the most common reasons startups get rejected and how Techstars mentors founders to avoid early mistakes. He also talks about the biggest themes shaping the future of venture capital.

In this episode, you’ll learn:

[03:00] How Andrew’s background in consulting, startups, and venture capital led him to Techstars 

[0...

Stephen Crook, Executive Director at Achieve Kids, explains how the organization supports students with special needs through individualized education, behavioral support, and vocational training. For over 60 years, Achieve Kids has provided a structured and supportive environment where students can develop independence. By working closely with school districts, educators, and families, the organization helps students transition back into public schools or the workforce. Stephen also shares the challenges and rewards of leading a nonprofit in special education, the impact of mentorship on student success, and how Achieve Kids partners with 35+ school districts to fulfill its mission.

Stephen Crook...

Allen Taylor, Managing Partner at Endeavor Catalyst, shares how Endeavor is fueling the rise of world-class startups in emerging markets—places often overlooked by traditional venture capital. Allen reveals how Endeavor identifies and supports high-potential founders before investing, why scaling talent is just as critical as scaling products, and how global ecosystems are evolving to produce unicorns from regions like Latin America, the Middle East, and Sub-Saharan Africa. He also shares practical advice for founders operating outside established innovation hubs and highlights how Endeavor’s unique investment model flips traditional venture capital on its head.

In this epis...

Connor Ryan, Partner at Bridge Venture Fund, shares his insights on investing in overlooked markets and the importance of sustainable unit economics. He explains why he prioritizes revenue quality over aggressive growth, the difference between projected and demonstrated product-market fit, and how Bridge Venture Fund supports startups tackling inefficiencies in industries like legal tech and sports sponsorship analytics. Connor also discusses the asymmetric risks in venture capital and how VCs can better support founders, even when things don’t go as planned.

In this episode, you’ll learn:
[02:27] From private equity to venture capital—Connor’s unconven...

David Hornik, founding partner at Lobby Capital, shares insights from his 25-year journey in the industry. David discusses the evolution of venture capital, the growing importance of relationships over transactions, and his structured yet practical approach to investing. He highlights how liquidity challenges impact founders and early investors. David also shares his take on what makes a startup truly investable and why understanding a problem deeply is more valuable than chasing market trends.

In this episode, you’ll learn:

[06:14] How venture capital has evolved from a simple early- vs. late-stage VC model to today's fragmented la...

Pablo Srugo, partner at Mistral Venture Partners and host of The Product Market Fit Show, shares his journey from co-founding startups like Gymtrack to becoming a venture capitalist focused on seed-stage investments. He reflects on the lessons learned through his and other founders' entrepreneurial highs and lows, including raising $6 million for a wearable tech company and navigating the challenges of a failed acquisition.

Now, as an investor, Pablo emphasizes the importance of founder passion, solving top-priority customer problems, and the "why" behind ventures. He discusses what makes founders stand out, noting that only 10% of first meetings turn...

Felipe Camposano, Managing Partner at Taram Capital, shares his journey as a pioneer in Chile's venture capital ecosystem and his efforts to support startups across Latin America. He discusses his transition from entrepreneur to investor, emphasizing his focus on mission-driven founders and leveraging networks for deal sourcing and evaluation. Felipe highlights Taram Capital’s unique approach to scaling startups through corporate partnerships, the importance of founder obsession with solving problems, and the critical role of localization in the region. He also shares insights from portfolio companies like YAPP and Webdox, showcasing the value of strong teams and founder-led growth.