The Sure Shot Entrepreneur

Gopi Rangan
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Successful entrepreneurs begin with the support of a few #earlybelievers. Gopi Rangan, founding partner at Sure Ventures, interviews venture capital investors in the Silicon Valley and beyond. Guests share insider stories on how they invest in early stage startups. Do you want to learn from real-life challenges, inspiring missions and important decisions by CEOs, founders, VCs, angels, and advisors? Listen to https://podcast.sure.ventures.

  1. We are in a Bubble of Bubble Talk, Not in a Real Financial Bubble

    FEB 10

    We are in a Bubble of Bubble Talk, Not in a Real Financial Bubble

    Aman Verjee, Founder and General Partner at Practical Venture Capital, shares his view of how venture capital has evolved over the past two decades and why secondary markets now play a critical role in the ecosystem. Drawing from his time at PayPal, eBay, and Sonos, Aman explains how companies today stay private far longer than they used to, what that means for early investors and employees, and how thoughtfully structured secondary transactions can reduce friction and misalignment on the cap table. He also challenges popular narratives around tech bubbles, walking through historical examples to explain why today’s AI-driven market looks fundamentally different. In this episode, you'll learn: [01:11] Aman’s journey from Wall Street to Practical VC [03:40] What made the early PayPal team exceptional [06:32] Follow the customer, not the original plan [10:44] Why are startups staying private longer today? [11:17] What secondary transactions actually are [18:41] How founders should handle secondary requests [26:11] Are we in a tech bubble today? The nonprofit organization Aman is passionate about: AYSO (American Youth Soccer Organization) About Aman Verjee Aman Verjee is the Founder and General Partner of Practical Venture Capital, a secondary-focused fund providing liquidity to early investors in late-stage private companies. Before launching Practical VC, Aman spent over a decade in finance and operations roles at PayPal and eBay, joining PayPal in 2001 before its IPO and witnessing its transformation from a money-beaming mobile app to the dominant payment platform for eBay. Earlier, he worked in investment banking in New York after studying economics at Stanford and constitutional law at Harvard Law School. Aman was recruited to PayPal by Peter Thiel and worked directly for David Sachs during the company's pivotal early years. Now partnering with Dave McClure, he focuses on Series C and D investments in SaaS and FinTech companies with $200M+ in revenue and clear paths to liquidity within 5-7 years. He's also writing a book on the history of financial bubbles and co-hosts the Trading Places podcast, analyzing private company valuations. About Practical Venture Capital Practical Venture Capital is a secondary-focused venture firm that provides liquidity solutions for early investors, employees, and funds. Operating with a 7-year fund structure instead of the traditional 10-15 years, Practical VC targets 20-40% discounts to last-round valuations in Series C and D companies with $200M+ in revenue and clear paths to exit. The firm specializes in SaaS and FinTech but has made exceptions for exceptional opportunities like SpaceX, now their biggest winner despite violating their typical investment criteria. Founded by Aman Verjee and Dave McClure, Practical VC evaluates roughly 50 companies at any given time, making 5-10 investments annually. The firm also offers SPVs for deals that don't fit their main fund and covers LATAM opportunities through an operating partner in Argentina. Their approach recognizes that modern venture capital requires new liquidity solutions as companies like SpaceX (23 years private), Airbnb (17 years), and Palantir (20 years) redefine what "patient capital" means. Subscribe to our podcast and stay tuned for our next episode.

    40 min
  2. Are You Willing to Deal With the Pain of Building a Successful Business?

    JAN 27

    Are You Willing to Deal With the Pain of Building a Successful Business?

    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 areas The nonprofit organization Jonathan is passionate about: 12/64 About Jonathan Crystal Jonathan 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 Partners Crystal 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.

    32 min
  3. Ignore the Bubble, Chase Alpha

    JAN 13

    Ignore the Bubble, Chase Alpha

    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 venture The nonprofit organization Amias is passionate about: Easterseals About Amias Gerety Amias 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 Investors QED 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.

    39 min
  4. Emerging Managers Succeed by Diversifying, Starting Early, and Staying Consistent

    12/02/2025

    Emerging Managers Succeed by Diversifying, Starting Early, and Staying Consistent

    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 perspectives The nonprofit organization Steve is passionate about: International Baccalaureate About 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.

    35 min
  5. Show Commitment to the Mission You Care About

    11/18/2025

    Show Commitment to the Mission You Care About

    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 funds Nonprofit highlight: AchieveKids About 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.

    27 min
  6. Artificial Intelligence is Becoming Service-First

    11/04/2025

    Artificial Intelligence is Becoming Service-First

    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 founder The 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.

    41 min
  7. Be the Quirky Underdog Obsessed About Building the Next New Thing

    10/21/2025

    Be the Quirky Underdog Obsessed About Building the Next New Thing

    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 safest The nonprofit Adam supports: The Ocean Cleanup About 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.

    30 min
  8. Make the Positive Power of Venture Capital Reach All Communities

    10/07/2025

    Make the Positive Power of Venture Capital Reach All Communities

    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 C******a 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 optimism The nonprofit organization Maryam is passionate about: PBS About 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.

    31 min
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4.9
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About

Successful entrepreneurs begin with the support of a few #earlybelievers. Gopi Rangan, founding partner at Sure Ventures, interviews venture capital investors in the Silicon Valley and beyond. Guests share insider stories on how they invest in early stage startups. Do you want to learn from real-life challenges, inspiring missions and important decisions by CEOs, founders, VCs, angels, and advisors? Listen to https://podcast.sure.ventures.

Information

  • Creator
    Gopi Rangan
  • Years Active
    2020 - 2026
  • Episodes
    182
  • Rating
    Clean
  • Copyright
    © 2022 The Sure Shot Entrepreneur
  • Show Website
    The Sure Shot Entrepreneur