The Sure Shot Entrepreneur

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 audacious vision.In this episode, you'll learn:[02:14] From Texas to Princeton to building an insurance dynasty in New York[04:04] Why insurance rewards creativity and curious minds[07:24] The brutal truth: 99% of a VC's job is saying no[10:31] Exiting the family business and finding the "why now" moment for venture[12:10] The ChatGPT revelation that launched Crystal Venture Partners[14:13] Investment thesis: $1-3M checks at day one for transformational companies[19:11] Why building a venture company means years of terror—and that's the test[21:59] Bright Harbor case study: From revenue model questions to product-market fit during LA fires[25:30] Most common reason for no: "We're not your best source of capital"[29:40] Finding investment opportunities in unusual areasThe nonprofit organization Jonathan is passionate about: 12/64About Jonathan CrystalJonathan Crystal is the Managing Partner of Crystal Venture Partners, a $33 million early-stage venture fund focused on AI-driven transformation in the insurance industry. Before entering venture capital, Jonathan spent 20 years as an operator in the insurance brokerage business, ultimately serving as CFO of Crystal and Company, a top-25 national insurance brokerage firm founded by his family. He led the firm to a successful exit to Alliant Insurance Services in 2018. Jonathan brings deep domain expertise and company-building experience to his investments. He backs seasoned, often serial entrepreneurs building transformational companies, writing $1-3 million checks as early as day one. His portfolio includes companies like Bright Harbor, Sixfold AI, NevadoAI, Comulate, and Corvus Insurance.About Crystal Venture PartnersCrystal Venture Partners is a $33 million early-stage venture capital firm founded in 2022 to capitalize on the AI transformation of the insurance industry. The firm writes $1-3 million first checks, often as the first institutional investor or alongside other first institutional investments. Crystal Venture Partners invests in 4-6 companies annually from a pipeline of 300+ opportunities, maintaining a highly selective approach with domain expertise enabling conviction at the earliest stages—sometimes backing founders on day one before product development. The firm's portfolio of 10 companies has shown strong momentum, with over half securing follow-on financing in multiple rounds within a year of initial investment. Led by Jonathan Crystal, who brings two decades of insurance industry operating experience, the firm specializes in identifying transformational opportunities where AI can create and capture significant value in risk management and insurance markets.Subscribe to our podcast and stay tuned for our next episode.

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 times out of 100 is the real job of a VC, Amias offers a masterclass in disciplined, thesis-driven investing.In this episode, you'll learn:[01:24] Amias's unique path from politics and Treasury to venture capital[05:13] The lever theory: how government and VC create systemic change[07:12] Why mechanical thinking and first principles matter in VC[14:48] QED's investment sweet spot: Series A and series B with undeniable momentum[19:25] What product-market fit really means and how to recognize it[22:14] Inverted AI: Why the world needs financial services for the AI economy[26:43] The AI bubble paradox: overvalued companies, transformative technology[32:57] Why early-stage founders should ignore the macro and focus on customers[34:31] The brutal math of ventureThe nonprofit organization Amias is passionate about: EastersealsAbout Amias GeretyAmias Gerety is a Partner at QED Investors, where he focuses on FinTech and InsurTech investments. Before joining QED in 2017, Amias spent eight years at the US Treasury Department from the first day of the Obama administration through its final day. During his tenure, he helped write the Dodd-Frank Act and built the Financial Stability Oversight Council, the organization responsible for monitoring systemic risk in the US financial system. His government experience during the financial crisis gives him a unique perspective on market dynamics and regulatory frameworks. A mechanical thinker who approaches investments with an essentialist mindset, Amias has invested in companies like Kin Insurance, Prosper, and Tint. He previously worked as a management consultant and with Save the Children in East Africa.About QED InvestorsQED Investors is one of the most successful venture capital firms focused on FinTech investments globally. As a multi-stage, global firm with a $650 million early-stage fund and $300 million growth fund, QED specializes in Series A and B investments in companies demonstrating exceptional momentum and product-market fit. The firm requires portfolio companies to show dramatic growth—expecting tripling in six months for Series A and tripling in a year for Series B investments. QED's partners bring deep domain expertise from building and scaling financial services companies, with a particular focus on companies that are reshaping financial services through technology. The firm is known for its rigorous, thesis-driven approach to investing and its high conviction in backing founders who have found authentic product-market fit in large, expanding markets.Subscribe to our podcast and stay tuned for our next episode.

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 venture investments[09:06] Comparing concentrated and diversified portfolio strategies[15:30] Understanding and meeting founders' needs[20:00] The role and support of emerging managers in venture capital[30:00] Evolution of the venture capital ecosystem and future perspectivesThe nonprofit organization Steve is passionate about: International BaccalaureateAbout Steve KimSteve Kim is a Partner at Verdis Investment Management, where he champions a data-driven and diversified approach to venture capital investments. With over two decades of experience, Steve backs emerging managers at the earliest stages, leveraging data to optimize returns while reducing risk. His career began in technology, where he held leadership roles at companies like Walt Disney and Alcatel before transitioning to investments.About Verdis Investment ManagementVerdis Investment Management, LLC (“Verdis”) is a Registered Investment Advisor under the Investment Advisors Act of 1940. Registration as an Investment Advisor does not imply any level of skill or training. The views expressed in this episode reflect those of Verdis as of the date of recording. Any views are subject to change at any time based on market or other conditions, and Verdis disclaims any responsibility to update such views. This commentary is not intended to be a forecast of future events, a guarantee of future results or investment advice. Because investment decisions are based on numerous factors, these views may not be relied upon as an indication of trading intent on behalf of any portfolio or strategy. The information contained herein has been prepared from sources believed to be reliable but is not guaranteed by Verdis as to its accuracy or completeness. This information does not constitute an offer to sell, or a solicitation of an offer to buy, an interest in any jurisdiction in which it is unlawful to make such an offer or solicitation. Certain information contained herein has been obtained from other parties. While such sources are believed to be reliable, neither Verdis nor its respective affiliates assume any responsibility for the accuracy or completeness of such information presented.Subscribe to our podcast and stay tuned for our next episode.

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:[01:00] - Stephen’s journey from Fulbright Fellow in Vietnam to venture capitalist at Spero Ventures[04:30] - How Spero spun out of Omidyar Network to back purpose-driven founders[08:10] - Investing early—with proof points that show real-world traction[11:10] - Why mission and authenticity matter more than hype in founder evaluation[14:00] - The story behind Spero’s investment in Juno and the value of long-term relationships[17:00] - How founders should work with junior investors inside VC firms[19:00] - Why conviction and alignment matter when founders choose their investors[22:00] - Stephen’s take on the concentration of capital and the future of small, focused fundsNonprofit highlight: AchieveKidsAbout Stephen WempleStephen Wemple is a Principal at Spero Ventures, where he invests in mission-driven founders building companies for a healthier, more sustainable, and fulfilling future. He has led investments across sectors such as healthcare, climate, and frontier technologies, backing founders who combine purpose with commercial ambition.Stephen began his career in early-stage venture capital, investing in emerging markets across Sub-Saharan Africa, Latin America, and South Asia. A Fulbright Fellow in Vietnam, he worked with the U.S. State Department to support entrepreneurship initiatives before joining Spero Ventures in its formative years. Stephen believes the best entrepreneurs are those who find and stay true to their mission.About Spero VenturesSpero Ventures is a Silicon Valley-based early-stage venture capital firm that backs mission-driven founders building companies for a healthy, sustainable, and fulfilling future. The firm leads or co-leads seed and Series A rounds with $2–4 million investments and maintains a concentrated portfolio to closely support each founder. Its team, which includes former operators from Tesla, eBay, and Stripe, has invested in companies like Juno (child disability insurance), Telo Trucks (electric pickup trucks), Tiny Health (gut health solutions), Euclid Power (renewable energy software), and Gencove (genome sequencing platform), reflecting its belief that purpose-driven startups can create both outsized impact and venture-scale returns.Subscribe to our podcast and stay tuned for our next episode.

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 this episode, you’ll learn:[03:18] The journey from founder to VC and back again[07:42] How Recursive defines “pre-seed” and why focus matters[12:51] What Itamar looks forward to in the first call with a founder[18:34] Data defensibility and AI applications: where value is created[25:07] The math and reasons behind saying no[31:40] What founders misunderstand about TAM sizing[36:58] Staying emotionally resilient as a founderThe nonprofit Itamar supports: Anti-Defamation League (ADL)About Itamar NovickItamar Novick is the founder and General Partner at Recursive Ventures, a pre-seed focused venture firm investing in AI-driven applications and data-advantaged software products. Before becoming an investor, Itamar spent over two decades as a founder and operator, including leadership roles at Gigya (acquired by SAP) and Life360. His approach to venture blends hands-on operator judgment with disciplined portfolio construction and deep founder support.About Recursive VenturesRecursive Ventures is a founder-GP led fund specializing in pre-seed and seed companies building AI-powered applications with strong data defensibility. The firm operates with a focused portfolio model, quick decision cycles, and direct founder support — avoiding the AUM-driven growth strategies common in larger firms. Recursive backs founders who combine technical depth, market insight, and authentic obsession. Portfolio companies include Life360, Ring, Tile, DataJoy, Armory, Placer.ai, Deel, May Mobility, Akash Network, Tomato AI, Anjuna Security, Harmony.ai among others.Subscribe to our podcast and stay tuned for our next episode.

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 consensus, has guided some of Boost VC’s biggest wins. Adam offers candid insights on founder evaluation, the power of weirdness, and how taking risks can often lead to the safest path to freedom.In this episode, you’ll learn:[01:00] The Draper legacy: how one family helped shape venture capital[05:45] From steel to startups: the early days of Silicon Valley[10:45] Adam’s first startup and lessons from failure[13:30] Why Boost VC bets on “endeavors of consequence”[16:00] How Adam thinks about risk, luck, and curiosity in investing[18:30] The weird founder advantage: high agency and obsession as signals[22:45] How Adam evaluates founders beyond the pitch deck[27:00] Rethinking risk: why the boldest path can be the safestThe nonprofit Adam supports: The Ocean CleanupAbout Adam DraperAdam Draper is the Founder and Managing Director of Boost VC, a pre-seed venture firm in Silicon Valley that invests in founders building the future—across crypto, space, deep tech, and frontier science. A fourth-generation entrepreneur and third-generation venture capitalist, Adam has backed more than 300 startups including Coinbase, Amplitude, and Radiant Nuclear. Known for his enthusiasm for “weird ideas,” Adam is passionate about helping founders take bold risks and build enduring companies.  About Boost VCBoost VC is a Silicon Valley-based pre-seed venture capital firm dedicated to supporting founders building transformative technologies in crypto, deep tech, and frontier industries. Founded in 2012, Boost VC has invested in over 400 companies worldwide. The firm averages roughly one deal per week and deploys around $500 K in its lead pre-seed rounds, along with $50 K fellowship checks for emerging founders.Subscribe to our podcast and stay tuned for our next episode.

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 into venture capital[04:18] The origins of Venture Forward and its mission to democratize access to VC[07:13] Why venture capital lacked diversity for so long[09:17] The champions who sparked change and why progress takes time[12:46] How Venture Forward educates and supports emerging managers[15:16] The scale of Venture Forward’s programs and the launch of the GP Masterclass[18:00] The story of Chingona Ventures and how early support creates lasting impact[20:54] What successful emerging managers do differently[24:43] Why starting a fund is harder than it looks—and what most underestimate[25:47] The future of venture: specialization, innovation, and realistic optimismThe nonprofit organization Maryam is passionate about: PBSAbout Maryam HaqueMaryam Haque is the Founding Executive Director of Venture Forward, a nonprofit organization dedicated to democratizing access to venture capital. She has over 15 years of experience in the venture ecosystem, including leadership roles at the National Venture Capital Association (NVCA) and Dow Jones VentureSource. Maryam is passionate about broadening participation in venture capital, supporting emerging fund managers, and advancing diversity, equity, and inclusion across the industry.About Venture ForwardVenture Forward is a Silicon Valley-based 501(c)(3) nonprofit launched under the NVCA to foster a more accessible, inclusive, and sustainable venture capital ecosystem. The organization supports individuals from all backgrounds through education, mentorship, and community programs such as VC University, Emerging Manager Office Hours, and the GP Masterclass. Its mission is to empower the next generation of investors, strengthen venture firms, and drive lasting change in the innovation economy.Subscribe to our podcast and stay tuned for our next episode.

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 venture and entrepreneurship[04:09] Lessons from Scopus and Octane: Why lived experience matters more than spreadsheets[06:07] How venture “reinvents itself” and demands a learning mindset[11:43] Sierra Ventures’ early-stage focus and flexible check sizes[14:33] Why raising the maximum check can backfire[16:44] The Eudia story: Hundreds of customer interviews and unique insights win conviction[23:07] How Sierra selects only ~2 deals per partner each year[27:26] Tim’s message to Washington: Don’t overregulate America’s greatest gift—entrepreneurshipThe nonprofit organization Tim is passionate about: American India FoundationAbout Tim GuleriTim Guleri is a Managing Partner at Sierra Ventures, where he focuses on AI, enterprise software, and emerging technologies. A successful founder turned investor, Tim led Scopus Technology to an IPO and later founded Octane Software, which was acquired for $3B. Since 2001, he has been a hands-on venture capitalist, backing transformative companies and guiding founders with lessons from both entrepreneurial wins and mistakes.About Sierra VenturesSierra Ventures is a Silicon Valley-based early-stage venture capital firm with over $2B in assets under management and more than four decades of experience. Specializing in enterprise infrastructure and emerging technologies, Sierra partners with founders at seed and Series A stages, providing flexible capital, operational expertise, and trusted connections to help startups scale into market leaders. Portfolio companies include Eudia, Yalo, Spectro Cloud, Endor Labs, Phenom People, Planera, Quintessent, Cimulate, among others.Subscribe to our podcast and stay tuned for our next episode.

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:[01:56] BG’s early journey from Calcutta to Silicon Valley and his career in academia, Yahoo, Oracle, LinkedIn, and NerdWallet[06:10] Why he calls himself a “secondhand entrepreneur” and what excites him most about venture capital[11:22] 8VC’s focus areas and why incubation is core to the firm’s strategy[14:05] The “geometry framework” for evaluating enterprise startups: persona, product, budget[19:30] Where BG sees opportunity in generative AI: orchestration, knowledge graphs, semantic layers, observability[25:12] Why networking must be intentional and based on service, not transactions[28:34] BG’s advice to founders on standing out and building authentic investor relationshipsThe non-profit Bhaskar is passionate about:  SACSA (Society for Arts and Culture of South Asia)About Bhaskar GhoshBhaskar Ghosh (BG) is a Partner at 8VC, where he leads investments in enterprise software, AI, data infrastructure, fintech, and healthcare, while incubating multiple startups. Previously, he held senior roles at Oracle and Yahoo, was the founding head of data infrastructure at LinkedIn, and served as CTO at NerdWallet, helping scale it to IPO. BG holds a PhD in Computer Science from Yale and is passionate about helping founders navigate zero-to-one journeys. Outside venture, he is deeply engaged in Indian classical music and supports community initiatives like Ragas Live.About 8VC8VC is a venture capital firm with approximately $7B in assets under management, investing in transformative technologies across enterprise software, AI, healthcare, logistics, fintech, and defense. With offices in Austin and San Francisco, 8VC partners with early-stage founders and also dedicates significant capital to incubation—building new companies alongside entrepreneurs. Its mission is to back ambitious founders solving global problems with scalable, science-driven solutions. 8VC’s portfolio includes category-defining startups that are shaping industries and tackling global challenges, including DataHub, Yugabyte, LightBeam, Tezi, OpenGov, Nile, AI21 Labs, AMP, Bedrock Robotics, 180° Insurance, Cambium, Candid Health among others.Subscribe to our podcast and stay tuned for our next episode.

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 Salem to Stanford to Silicon Valley: Zach’s journey into venture capital[03:38] Why venture is a “blank canvas” and not a zero-sum game[05:46] Foundation Capital’s early-stage focus and Zach’s typical check size[06:58] “There’s no time too early”: When founders should reach out—and what Zach looks for[09:43] What really happens in the first meeting (and why it’s about participation, not just Q&A)[12:54] Should founders ditch the pitch deck? Zach’s advice might surprise you[16:40] The Push Cash story: How one founder showed true differentiation from day one[19:34] Why Zach says no—even after initial interest—and what makes a $10B story possible[22:42] How venture has professionalized—and why AI brings back the excitementAbout Zach NooraniZach Noorani is a Partner at Foundation Capital, where he invests in early-stage fintech and enterprise startups. With over 14 years of experience in venture capital, Zach has a background that spans corporate VC at Capital One and a passion for supporting founders who demonstrate velocity of learning and unique insight. Based in Los Angeles, Zach focuses on inception-to-Series A companies and has led investments in several innovative fintech ventures.About Foundation CapitalFoundation Capital is a Silicon Valley-based venture capital firm with over 30 years of experience backing early-stage companies. The firm partners with founders from inception through Series A, providing hands-on support to help build transformative businesses. Foundation Capital’s portfolio includes category-defining companies across fintech, enterprise, and emerging technologies.Subscribe to our podcast and stay tuned for our next episode.

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: Jacques’ global path into tech and AI[05:20] “This time it’s different” is rarely true—how founders should think about hype cycles[11:00] Why more capital doesn’t mean an easier path for founders[13:30] The venture industry is now a volume business—but founders need depth, not scale[15:00] What founders get wrong about market entry—and why randomness is the enemy[17:30] Focused beats first: how Medigate won in cybersecurity by narrowing in on medical devices[30:00] The importance of reflection, walking without your phone, and finding a mentor[37:00] Jacques' nonprofit passion: creating dialogue between communities in conflictThe nonprofit organization Jacques is passionate about: TechnionAbout Jacques BenkoskiJacques Benkoski is a General Partner at US Venture Partners (USVP), where he invests in enterprise software, AI, and cybersecurity startups. He has over 20 years of experience as a VC, following a successful career as a startup CEO and tech executive. Jacques is also the author of Market Entry Strategy, a hands-on guide for founders navigating early customer acquisition. A passionate advocate for founder wellbeing and long-term thinking, Jacques mentors entrepreneurs around the world.About U.S. Venture PartnersU.S. Venture Partners (USVP) is a leading Silicon Valley venture capital firm with a strong focus on early-stage companies in enterprise software, cybersecurity, and healthcare. With more than $4 billion raised since its founding in 1981, USVP has backed over 500 companies including Box, Guidewire, Trusteer, and Medigate. The firm brings decades of operational expertise and deep sector insight to help founders scale with clarity and discipline.Subscribe to our podcast and stay tuned for our next episode.

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 Iterative Health before AI in gastrointestinal innovation was trendy[17:40] "I value humility more than confidence." Amit’s surprising lens on what makes a founder trustworthy (and fundable)[21:30] Understanding how to extend your runway to 24 months is the key to success in early-stage startups.[25:20] What founders must understand about true VC alignment[29:49] Value vs. valuation: The myth founders must unlearn to avoid being misled by hype-driven fundraisingThe nonprofit organization Amit is passionate about: Hospital for HopeAbout Amit GargAmit Garg is the Co-founder and Managing Partner at Tau Ventures, a Silicon Valley-based early-stage venture capital firm. With a background in engineering, product, and investing, Amit has built a career around intersecting deep tech with human impact. Prior to founding Tau Ventures, he worked at Google, Norwest Venture Partners, and Samsung NEXT. He’s also the co-founder of Hospital for Hope, a nonprofit hospital in rural India. Amit brings a global, grounded, and mission-driven lens to evaluating startups, with particular focus on AI, digital health, and enterprise infrastructure.About Tau VenturesTau Ventures is a seed-focused venture capital firm investing in startups at the intersection of AI, healthcare, automation, and enterprise infrastructure. Founded by operators-turned-investors, the firm applies deep technical understanding and pragmatic business insight to back early-stage teams tackling real-world challenges. Tau operates with a lean fund model, high conviction, and a focus on value creation over hype. Its portfolio includes startups applying cutting-edge technology to improve healthcare diagnostics, workflow automation, and infrastructure scalability. Tau’s portfolio companies include 1Password, Absci, Alpaca Health, Autonomize AI, Iterative Health, Vecna Robotics among others.Subscribe to our podcast and stay tuned for our next episode.

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.