Secondaries are Essential for the Venture Capital Market

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 evolution of accelerators and why “lots of little bets” took off[09:50] How cloud, open source, and low CAC changed the startup funding game[12:49] Why startup liquidity timelines have doubled—and what that means for founders and LPs[14:56] What secondaries really are (hint: not just one thing)[19:31] Does venture’s illiquidity attract the right kind of investors—or just the most patient?[22:06] The discipline of public markets vs. the opacity of private ones[26:37] What Practical VC looks for in a secondary opportunity (and the $50M–$100M revenue rule)[29:14] How Dave screens funds and companies for possible exits[33:37] What’s exciting (and worrying) about secondaries, stablecoins, and emerging marketsThe nonprofit organization Dave is passionate about: New StoryAbout Dave McClureDave McClure is the founder of Practical Venture Capital, a firm focused on liquidity through venture secondaries. Previously, he co-founded 500 Startups, one of the world’s most active early-stage venture funds. A PayPal alumni and self-described nerd turned investor, Dave has worked across engineering, marketing, and venture roles, investing in hundreds of startups globally. He’s known for his honest insights and bold bets on opportunities before they’re ‘cool’.About Practical Venture CapitalPractical Venture Capital is a Silicon Valley-based VC secondary firm providing liquidity to GPs, LPs, and founders through targeted secondary investments. Specializing in fund-level and company-level secondaries, Practical VC aims to shorten the venture capital time horizon by backing mature, revenue-generating companies with clear exit paths. The firm focuses on portfolios nearing liquidity and brings a flexible, creative approach to valuation, pricing, and structure.Subscribe to our podcast and stay tuned for our next episode.

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 student got Brian hooked on innovation early[05:54] Why Brian left startup life after seven companies to support founders solving global problems[09:18] The urgent reasons our food system needs reinvention—from climate to national security[12:33] FTW Ventures investment philosophy and focus areas[22:50] Hard truths for founders in food and agriculture[31:13] The story of a founder who proved his market, didn’t wait for funding, and built trust[37:05] What needs to change in VC: stop party rounds, leave space for small funds, invest with purposeThe nonprofit organization Brian is passionate about: World Central KitchenAbout Brian FrankBrian Frank is the founder and general partner at FTW Ventures, a venture capital firm focused on technology solutions in food, agriculture, and health. A serial entrepreneur with a background in computer science and product development, Brian has launched and scaled seven startups. He brings that hands-on experience to founders tackling real-world challenges, backing science-backed and mission-driven companies that aim to improve life on the planet.About FTW VenturesFTW Ventures is a Silicon Valley-based venture capital firm investing in the future of food, agriculture, and human health. With a thesis grounded in problem-first investing, FTW backs early-stage startups applying biotechnology, artificial intelligence, automation, and sustainable systems to global challenges. Their portfolio includes companies advancing biomanufacturing, food-as-medicine, CRISPR-based crop innovation, and more—pursuing returns across people, planet, and profit. Companies in FTW’s portfolio include Boston Bioprocess, ALTR, Sylvan Health, FreshFry, Izote Biosciences, Arise, Quorum Bio, Earthodic, Heritable, Brilliant Harvest, VoltAir, Geltor, Spoiler Alert, Plantible Foods, Galley, Phytoform, Nfinite Nanotech, Yali Bio, and Debut Biotechnology.Subscribe to our podcast and stay tuned for our next episode.

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, you’ll learn:[02:05] Why Geoff believes AI is not ‘just’ a tool but a cognitive force reshaping humanity[06:29] The subtle but profound difference between tools and intelligent agents[13:56] Who wins and who loses in an AI-driven future, and what roles must investors play?[20:36] Can we still design a utopian future with AI?[24:06] The types of founders Geoff wants to back through SAIF[26:30] Why mission-aligned safety startups still need product-market fit[28:46] What happens when AI does everything—and what humans will still choose to doThe nonprofit organization Geoff is passionate about: AI Venture LabAbout Geoff RalstonGeoff Ralston is the founder of SAIF (Safe Artificial Intelligence Fund) and former President of Y Combinator. A longtime startup investor, entrepreneur, and thought leader, Geoff previously founded Imagine K12, an edtech accelerator later merged with YC. With decades of experience launching and scaling category-defining startups, Geoff now focuses on funding companies that ensure AI becomes a force for good, addressing challenges around safety, security, and the future of human work.About SAIFSAIF (Safe Artificial Intelligence Fund) is a venture capital firm dedicated to building a safer future with AI. Founded by Geoff Ralston, SAIF invests in startups focused on AI safety, biosafety, interpretability, and information integrity. The firm supports mission-driven founders creating scalable solutions to counteract risks and ensure that AI technologies empower rather than endanger society.Subscribe to our podcast and stay tuned for our next 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 treehouses to model airplanes: Nadav’s early love for tech and tinkering[03:26] How informal advising turned into full-time investing[04:57] The meaning behind the name at.inc and how it reflects the firm’s thesis[10:01] “What kind of company will this be in 30 years?”—the power of visionary questions[13:30] Building conviction: fast no’s, thoughtful yes’s[15:51] How early-stage founders can build a relationship with Nadav[20:14] Why Nadav says no: timing and fit[24:07] How venture capital should evolve to serve today’s foundersThe nonprofit organization Nadav is passionate about: Tel Aviv UniversityAbout Nadav EylathNadav Eylath is the founder and managing partner of at.inc, a venture capital firm that invests at the very inception of startups. With a background in data science, marketing, and company-building, Nadav brings an operator’s empathy and a long-term investor’s lens to early-stage ventures. His career spans roles at startups acquired by companies like Intuit, as well as over a decade of deliberate, hands-on venture investing. Nadav’s approach is grounded in trust, curiosity, and a passion for helping founders bring technically ambitious and globally relevant ideas to life.About at.incat.inc—short for “at incorporation or at inception”—is a Silicon Valley-based venture capital firm that backs startups from day zero. The firm invests in deeply technical companies with global potential, often writing the first check when founders are just forming their ideas. Generalist by design, at.inc partners with entrepreneurs across sectors, emphasizing long-term vision, high trust, and a hands-on approach. With a focused investment pace and founder-first philosophy, at.inc supports startups throughout their full journey, from inception to global scale.Subscribe to our podcast and stay tuned for our next episode.

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[04:06] Venture capital as a humble act of early belief—and why VCs are deeply interdependent[06:46] Kicker Ventures' mission to create a happier and healthier world through science-backed innovation[12:31] What founders must do in the first meeting to excite impact-driven investors[19:19] Why founders should build strong communities early and ask for help[26:00] Tomoko’s call to eliminate barriers to global innovation and unlock hidden talent worldwideThe non-profit organization Tomoko is passionate about: Kadampa Meditation Center SFAbout Tomoko IshikuraTomoko Ishikura is the Managing Partner at Kicker Ventures, where she leads investments in science-backed innovations shaping the future of healthcare. Originally trained as a pharmacist and molecular biologist, Tomoko transitioned into business development, consulting, and now venture capital. Drawing from her global experience across Japan and Silicon Valley, Tomoko brings a distinctive focus on empathy, impact, and community-driven success to the startup ecosystem.About Kicker VenturesKicker Ventures is a San Francisco-based venture capital firm investing in transformative solutions for the future of healthcare. Kicker backs science-backed innovations that foster happiness, empower individuals, amplify the work of health professionals and researchers, and create meaningful human connections. With a deep commitment to measurable impact, Kicker Ventures partners with visionary founders reimagining health and wellbeing for future generations.Subscribe to our podcast and stay tuned for our next episode.

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 from immigrant kid in New York to serial entrepreneur in Silicon Valley[06:50] Why Mahesh believes frustration often leads to the best startup ideas[10:55] Inside Zoom’s AI journey—and how Mahesh helped launch AI Companion at record speed[13:14] Lessons on leadership from Eric Yuan: customer obsession and quality over cost[20:41] Mahesh’s advice to AI-first founders: ship fast, sell faster, and validate deeply[24:23] What separates point solutions from workflow-embedded companies[27:03] Mahesh’s nuanced take on AI’s societal risks—and why we’re not ready[31:25] What is Funda? Why a grassroots founder community is boomingThe nonprofit organization that Mahesh supports: UStriveAbout Mahesh RamMahesh Ram is a serial entrepreneur and expert in artificial intelligence, most recently serving as Head of AI at Zoom. He was co-founder and CEO of Solvvy, a pioneering AI startup in customer experience, acquired by Zoom. Prior to that, he led GlobalEnglish, a business English learning platform used by millions worldwide. Mahesh advises founders, invests in early-stage startups, and is a founding member of FUNDA, a growing grassroots community of founders of Indian origin. He is deeply passionate about education, technology, and building systems that simplify complex problems.About FUNDAFunda is a pay-it-forward community for founders of Indian origin, designed to support early-stage entrepreneurs through collaboration, connection, and shared experience. Built by founders for founders, Funda now includes over 1,250 members across Silicon Valley, Texas, and India. The community offers peer support, curated events, and access to a trusted network—entirely volunteer-driven and mission-focused.About UStriveMahesh actively volunteers with UStrive, a nonprofit providing free virtual mentoring for high school and college students with financial need. The platform matches students with mentors to help navigate college admissions and financial aid processes—removing barriers to higher education for underserved youth.Subscribe to our podcast and stay tuned for our next episode.

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 [07:34] How Techstars selects startups from thousands of applications—what matters most[14:01] The #1 mistake founders make when applying to Techstars, and how to avoid[20:50] Why founders need to build investor relationships early when thinking about fundraising[26:04] Why the VC industry needs more transparency—and how that benefits foundersThe non-profit organization Andrew is passionate about: Magic BusAbout Andrew ClelandAndrew Cleland is the Chief Investment Officer at Techstars, where he oversees investment strategy, fundraising, and portfolio growth across Techstars’ global network of accelerators. With over two decades in venture capital and early-stage investing, he previously led investments at Comcast Ventures and Time Warner Investments. An INSEAD MBA graduate, Andrew has backed dozens of high-growth startups and is focused on empowering the next generation of global founders.About TechstarsTechstars is one of the world’s leading startup accelerators, backing thousands of early-stage companies across 50+ accelerator programs worldwide. Since 2006, Techstars has helped launch 20+ unicorns, including SendGrid, DigitalOcean, Uber, Twilio, DataRobot and Outreach. The program provides mentorship, funding, and global networks to help startups scale fast.Subscribe to our podcast and stay tuned for our next episode.

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, Executive Director at AchieveKids, explains how the organization supports students with special needs through individualized education, behavioral support, and vocational training. For over 60 years, AchieveKids 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. In this special Podcasthon episode, Stephen also shares the challenges and rewards of leading a nonprofit in special education, the impact of mentorship on student success, and how AchieveKids partners with 35+ school districts to fulfill its mission.In this episode, you'll learn:[03:00] How Stephen’s journey from psychology research to teaching led him to AchieveKids[07:34] What makes AchieveKids different from traditional special education programs[14:01] A powerful success story of a student overcoming severe behavioral challenges[20:50] Why teacher shortages threaten special education and what’s being done about it[23:09] The biggest challenges families face when seeking support for their children[26:04] The future of AchieveKids and how the program is expanding to meet growing needsAbout Stephen CrookStephen Crook is the Executive Director of AchieveKids, a nonprofit school serving students with special needs. With a background in developmental psychology, teaching, and school administration, he has dedicated his career to improving special education programs and advocating for students with disabilities. Before joining AchieveKids, Stephen worked as a therapeutic teacher and school director, helping students with significant behavioral and emotional needs gain the skills to succeed in school and beyond.About AchieveKidsAchieveKids is a nonprofit school that serves students ages 5 to 22 with autism, intellectual disabilities, emotional needs, and developmental challenges. With campuses in Palo Alto and East San Jose, AchieveKids partners with 35+ school districts to provide individualized education, behavioral support, mental health services, and vocational training. The goal is to help every student transition into a more independent and fulfilling life.Subscribe to our podcast and stay tuned for our next episode.

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 episode, you’ll learn:[03:00] How Allen’s international career led him to Endeavor and a global mission to support entrepreneurs in overlooked markets[05:55] Why talent is everywhere—but opportunity isn’t—and how Endeavor flips the script on where billion-dollar companies are built[09:50] The contrarian strategy that made Endeavor Catalyst one of the most successful global venture funds[15:31] What does it take to become an Endeavor startup? [25:48] The biggest challenges founders face outside major tech hubs—and why scaling talent is the hardest part of growth[29:04] Why Allen is bullish on Latin America, the Middle East, and Sub-Saharan Africa as the next breakout regions for global innovationThe non-profit organization Allen is passionate about: Kauffman FellowsAbout Allen TaylorAllen Taylor is the Managing Partner at Endeavor Catalyst, the venture capital fund supporting Endeavor’s global community of high-impact entrepreneurs. With nearly 20 years at Endeavor, Allen has helped drive the organization's global expansion and innovative investment model, which backs companies across Latin America, the Middle East, Africa, and beyond. Previously, Allen worked in international development and studied in Argentina, igniting his passion for supporting global entrepreneurship. Allen is also a Kauffman Fellow and serves on the board of the Kauffman Fellows Program.About Endeavor CatalystEndeavor Catalyst is the co-investment fund of Endeavor, the leading global community of high-impact entrepreneurs. Since 2012, Endeavor Catalyst has invested in over 300 companies across 30+ countries, backing founders who are building transformative businesses in emerging and underserved markets. With a rules-based model, Endeavor Catalyst automatically invests alongside professional VCs when Endeavor Entrepreneurs raise Series A, B, or C rounds. Its portfolio includes Latin America’s first unicorn, Mercado Libre, and pioneering companies like Nubank and InstaDeep.Subscribe to our podcast and stay tuned for our next episode.

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 unconventional path and why he invests in overlooked industries[07:06] How Bridge Venture Fund identifies overlooked industries ripe for innovation[12:28] The two key questions Connor asks in every pitch meeting[16:52] How legal tech startups like CaseText are transforming traditional workflows[17:32] Why non-lead VCs like Bridge Venture Fund have to move fast but still maintain rigorous diligence[22:38] The most common reason Connor passes on startups: weak unit economics and misleading LTV/CAC assumptions[27:49] Connor’s perspective on venture capital’s asymmetric risk and why founders bear the brunt of failureThe non-profit organization that Connor is passionate about: World Wildlife FundAbout Connor RyanConnor Ryan is a Partner at Bridge Venture Fund, where he focuses on investing in startups serving overlooked and underserved industries. Before joining Bridge, he worked in private equity and investment banking, gaining deep insights into business model sustainability and market inefficiencies. Connor holds an MBA from Northwestern University’s Kellogg School of Management and is passionate about supporting founders who bring real innovation to lagging industries.About Bridge Venture FundBridge Venture Fund is a Chicago-based early-stage VC firm investing in startups that serve industries underserved by innovation. With a focus on sustainable unit economics and market-defining solutions, the firm has backed companies in legal tech, sports sponsorship analytics, retail, and more. Notable investments include CaseText (acquired by Thomson Reuters) and Trajektory.Subscribe to our podcast and stay tuned for our next episode.