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    Business

    How I Invest with David Weisburd

    How I Invest with David Weisburd is a podcast that interviews the world’s leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.

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    Copyright: © Copyright 2025 How I Invest with David Weisburd

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    Latest Episodes:
    E443: Why the Next Trillion-Dollar Startup Won’t Be a Software Company Oct 16, 2026
    Show notes

    What if AI makes software abundant and shifts venture capital’s biggest opportunities into the physical world? Leo Polovets is a General Partner at Humba Ventures, an early-stage deep tech fund investing across robotics, defense, energy, manufacturing, and other physical industries. Leo explains why AI is commoditizing software, why hardware may capture more value as a result, and why some of the best opportunities are hiding in industries with almost no startup competition. We also discuss how to underwrite deep tech before revenue, what separates exceptional founders, the infrastructure bottlenecks created by AI, and why the biggest risk to deep tech may be its dependence on continued funding.

    Highlights:
    - Why the best companies and investors need a lane uniquely their own
    - Why quantity of meetings can improve venture investment quality
    - How AI growth is changing the definition of exceptional traction
    - Why deep tech companies have a completely different revenue curve
    - What separates the best venture capitalists from average investors
    - Why Leo believes hardware investing is becoming more attractive
    - How to evaluate deep tech companies years before meaningful revenue
    - Why hardware may not be as capital intensive as investors assume
    - The founder traits that matter most when building physical products
    - Why Leo is cautious on investing directly in humanoid robotics
    Guest Bio:
    Leo Polovets is a General Partner at Humba Ventures, an early-stage deep tech fund investing 500K–1M in companies across robotics, bio, defense, energy, manufacturing, and other physical industries. He previously co-founded Susa Ventures, an early investor in companies including Robinhood, Flexport, and Stord.
    Sponsors:
    Juniper Square:
    Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit junipersquare.com/howiinvest.
    AlphaSense:
    AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit alpha-sense.com/howiinvest to learn more.
    AlphaSummit Discount Code: AS26HII50
    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.
    Stay Connected with David Weisburd:
    X/Twitter: @dweisburd
    LinkedIn: https://www.linkedin.com/in/dweisburd/
    Weisburd Pierce: https://www.weisburdcapital.com/
    Stay Connected with Leo Polovets:
    LinkedIn:https://www.linkedin.com/in/lpolovets
    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.
    Disclaimer:
    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Why the Best Investors Need Their Own Lane (2:05) Why More Meetings Can Make You a Better Investor (6:14) What Separates the Best Venture Capitalists? (10:03) Why Leo Is So Bullish on Hardware (12:31) How Do You Underwrite a Deep Tech Startup? (16:08) Is Hardware Really More Capital Intensive? (22:38) Where Are Deep Tech’s Most Underrated Opportunities? (33:28) What Separates the Top 0.1% of Founders? (41:28) Why Leo Is Cautious on Humanoid Robotics (56:26) The Investing Lesson Leo Learned the Hard Way

    E442: Nelson Mills on Building a $100 Billion Company, the China Threat, and the Future of War Oct 14, 2026
    Show notes

    What happens when autonomous underwater vehicles become cheap enough to manufacture at scale? Nelson Mills is the Founder of Vatn Systems, a defense technology company building autonomous underwater vehicles. Nelson explains why undersea autonomy has lagged aerial drones, how advances in AI, navigation, manufacturing, and autonomy are changing the economics, and why Vatn is building lower-cost systems designed to operate at scale. We also discuss raising $85 million for a hardware startup, the rise of asymmetric warfare, lessons from Anduril, and what it takes to build a new defense prime.

    Highlights:

    • Why Nelson left venture capital to become a founder
    • Why undersea autonomy is finally reaching an inflection point
    • The navigation and communications problems that make underwater technology so difficult
    • How Vatn raised its first $2 million pre-seed round in just 30 days
    • Why hardware founders should start with the smallest viable version of their product
    • Vatn’s plan to become a focused defense prime for the undersea market
    • What Anduril proved about building defense technology differently
    • How lower-cost underwater vehicles could change deterrence for smaller countries
    • The biggest hiring lesson Nelson learned as a founder
    • Why founders should always be building relationships for their next round

    Guest Bio:

    Nelson Mills is the Founder of Vatn Systems, a defense technology company building autonomous underwater vehicles. After growing up on the water and spending roughly nine years operating at startups, Nelson moved into venture capital before leaving to build Vatn.

    Sponsors:

    Juniper Square:

    Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

    AlphaSense:

    AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

    AlphaSummit Discount Code: AS26HII50

    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

    **Stay Connected with David Weisburd: **

    X/Twitter: @dweisburd

    LinkedIn: https://www.linkedin.com/in/dweisburd/

    Weisburd Pierce: https://www.weisburdpierce.com/

    Stay Connected with Nelson Mills:

    LinkedIn:https://www.linkedin.com/in/millsn/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) How Growing Up on a Sailboat Led to Vatn Systems (1:18) Why Nelson Left Venture Capital to Become a Founder (6:08) Why Undersea Autonomy Is Finally Having Its Moment (8:20) What Needs to Happen for Underwater Drones to Scale? (11:13) How Do You Build a Company Everyone Says Is Impossible? (12:41) How Vatn Raised $2 Million on a Dream (20:53) How Vatn Went From Pre-Seed to $85 Million Raised (21:48) Can Vatn Become the Next Defense Prime? (27:42) How Defense Technology Could Change Global Deterrence (45:21) The Advice Nelson Would Give Himself as a First-Time Founder

    E441: Startup Investing When the Cost of Building Goes to Zero Oct 12, 2026
    Show notes

    What if AI makes the founder more important, not less? John Borthwick is the Founder of betaworks, the startup studio and venture firm behind companies including Giphy, Dots, bitly, and TweetDeck, with investments in companies including Twitter, Tumblr, Kickstarter, and Hugging Face. We break down why John now puts more weight on founders than products, how betaworks identified Hugging Face before transformers reshaped AI, and why he believes the biggest opportunity is moving toward the AI application layer. We also discuss open-source AI, AI security, the changing nature of work, and why John believes AI was discovered rather than invented. John Borthwick is the Founder of betaworks, the startup studio and venture firm behind companies including Giphy, Dots, bitly, and TweetDeck, with investments in companies including Twitter, Tumblr, Kickstarter, and Hugging Face. We break down why John now puts more weight on founders than products, how betaworks identified Hugging Face before transformers reshaped AI, and why he believes the biggest opportunity is moving toward the AI application layer. We also discuss open-source AI, AI security, the changing nature of work, and why John believes AI was discovered rather than invented.

    Highlights:
    - Why John now believes the founder matters more than ever
    - The unusual question he uses to understand a founder’s emotional connection to their company
    - Why betaworks chose the venture studio model instead of a traditional fund
    - How betaworks combines accelerator programs with pre-seed investing
    - Why John focuses on proximity to products instead of traditional pattern matching
    - How AI is changing founders from builders into “steerers”
    - What betaworks saw in Hugging Face before transformers changed AI
    - Why John believes open and closed AI models need to coexist
    - The AI risks John thinks deserve more attention than existential risk
    Guest Bio:
    John Borthwick is the Founder of betaworks, which he founded in 2008 as a startup studio for building and investing in early-stage consumer technology companies.
    Sponsors:
    Juniper Square:
    Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
    AlphaSense:
    AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
    AlphaSummit Discount Code: AS26HII50
    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.
    Stay Connected with David Weisburd:
    X/Twitter: @dweisburd
    LinkedIn: https://www.linkedin.com/in/dweisburd/
    Weisburd Pierce: https://www.weisburdpierce.com/
    Stay Connected with John Borthwick:
    LinkedIn:https://www.linkedin.com/in/jborthwick/
    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.
    Disclaimer:
    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Why John Now Believes Founders Matter More Than Ever (1:36) The Question John Uses to Identify Exceptional Founders (7:34) Why Betaworks Chose a Venture Studio Over a Traditional Fund (13:42) How John Finds 100x Venture Investments (15:45) Why AI Is Making Founders More Important (21:30) How Betaworks Found Hugging Face Before the AI Boom (29:03) Why Open-Source AI Still Matters (40:14) Why John Believes AI Was Discovered, Not Invented (56:13) Where the Biggest AI Opportunities Are Emerging (1:01:10) How to Make Your Career Antifragile to AI

    E440: What Steve Jobs Taught Me About Great Founders Oct 09, 2026
    Show notes

    What did Steve Jobs understand about building great companies that most founders miss? Steven Rosenblatt is Co-Founder and General Partner at Oceans, a seed-stage venture firm based in New York City. Drawing on more than two decades as an operator and investor, including his time at Apple and Foursquare, Steven shares what he learned working directly with Steve Jobs, how he separates ambitious founders from delusional ones, what drew Oceans to Etched, and why AI is creating a technology cycle unlike anything he has seen before.

    Highlights:

    • Why great technology companies always start with exceptional people
    • How Steven separates founder ambition from delusion
    • What great founders understand about attracting world-class talent
    • What Steven learned from working directly with Steve Jobs
    • Why Steve Jobs obsessed over details most CEOs would ignore
    • How Apple sold $60 million of advertising before the product was live
    • Why the founders of Etched immediately stood out
    • The founder traits that remain constant across every technology cycle
    • Why AI is moving faster than previous technology revolutions
    • Why Steven believes both enormous winners and failures are coming
    • What Foursquare taught him about valuations and paper gains

    Guest Bio:

    Steven Rosenblatt is Co-Founder and General Partner at Oceans, a seed-stage venture firm headquartered in New York City. Previously, he held senior operating roles at Foursquare and Apple, joining Apple after its acquisition of Quattro Wireless.

    Sponsors:

    Juniper Square:

    Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

    AlphaSense:

    AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

    AlphaSummit Discount Code: AS26HII50

    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

    Stay Connected with Steven Rosenblatt:

    LinkedIn:https://www.linkedin.com/in/stevenrosenblatt/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) What Great Technology Companies Have in Common (2:47) How to Separate Ambition From Delusion (6:57) What Steven Learned Working With Steve Jobs (16:10) What Steve Jobs Understood About Building Companies (27:26) How Apple Changed Steven as a Leader (37:30) What Made the Founders of Etched Stand Out (42:18) Do the Rules for Great Founders Change With AI? (47:39) Why This AI Boom Is Different From Every Previous Cycle (51:45) The Timeless Career Lesson Steven Would Give His Younger Self (55:30) Why New York Took Decades to Become a Tech Hub

    E439: Ethan Thornton: The 22-Year-Old Building a $3.7 Billion Defense Company Oct 07, 2026
    Show notes

    What if the future of warfare is determined by who can innovate faster, not who can spend more? Ethan Thornton is the Founder and CEO of Mach Industries, a defense technology company he started after dropping out of MIT. We break down how Mach went from experimenting with roughly 20 technologies to becoming a multibillion-dollar company, why Ethan believes asymmetric technology is reshaping modern warfare, and how Pentagon procurement is evolving. We also discuss China and Taiwan, lessons from Ukraine, autonomous warfare, recruiting exceptional talent, taking risk, and why Ethan believes great founders should empower their teams rather than make every decision themselves.

    Highlights:

    • Why Ethan dropped out of MIT to build a defense company
    • How Mach experimented with roughly 20 technologies before narrowing its focus
    • Why building prototypes created an advantage over presenting slide decks
    • How Pentagon procurement is changing for defense startups
    • Why Ethan believes cost-plus contracting can create the wrong incentives
    • Why venture capital matters for asymmetric technology
    • How Mach recruits people around mission rather than persuasion
    • Why Ethan doesn’t view Anduril as a zero-sum competitor
    • How media fits into the strategy of a defense company
    • Why Ethan believes founders should find people they trust and empower them
    • What he misunderstood about “founder mode”

    Guest Bio: Ethan Thornton is the Founder and CEO of Mach Industries, a defense technology company focused on developing and manufacturing next-generation systems. Thornton began working on ideas for asymmetric technology as a teenager and started Mach after leaving MIT.

    Sponsors:

    Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

    AlphaSense:

    AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

    AlphaSummit Discount Code: AS26HII50

    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

    Stay Connected with Ethan Thornton:

    LinkedIn:https://www.linkedin.com/in/ethan-thornton-74417024a/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Why Ethan Thornton Dropped Out of MIT to Build Mach Industries (2:50) How an MIT Dropout Built a Multibillion-Dollar Defense Company (5:00) Why Mach Started by Building 20 Different Technologies (6:41) How the Pentagon Is Changing Defense Procurement (12:24) Could the U.S. Deter a Conflict Over Taiwan? (25:00) How Mach Chooses Which Defense Technologies to Build (32:47) How Mach Competes for the Best Engineering Talent (39:03) Why Ethan Believes Staying at MIT Was the Bigger Risk (43:55) The Leadership Lesson Ethan Wishes He Learned Earlier (46:02) What Ethan Misunderstood About “Founder Mode”

    E438: Will Robbins on Elon Musk, AI & the Future of Silicon Valley Oct 05, 2026
    Show notes

    What if the biggest edge in venture capital is identifying an exceptional founder before everyone else does? Will Robbins is a technology-focused venture investor and founder of Robbins Capital, where he backs companies starting at formation. Previously, Will joined Contrary as its first employee and helped grow the firm to more than $250 million in AUM. In this episode, Will explains why traditional VC brands may matter less in an AI-driven world, how he identifies exceptional founders before they have traction, why the best startups often pivot, and why reputation with founders may be the most important asset a venture investor can build.

    Highlights:

    • Why traditional VC brands may be losing their edge
    • How AI could fundamentally change the economics of seed rounds
    • Why founders may need dramatically less capital to reach product-market fit
    • How two 17-year-old founders built Zepto into a massive retailer
    • Why college dropouts can produce disproportionately large venture outcomes
    • The elusive “X factor” Will looks for in exceptional founders
    • Why a founder’s social graph can reveal signals a pitch meeting cannot
    • Why extreme focus may be one of the most important founder traits
    • The small group of business models behind many of venture’s biggest outcomes
    • Why Will remains optimistic about software despite AI disruption
    • Why 50% of Will’s successful early-stage investments pivoted
    • The one asset Will believes matters most for a long-term venture career

    Guest Bio:

    Will Robbins is a technology-focused venture investor and founder of Robbins Capital, where he backs companies starting at company formation. Prior to investing under his own name, Will joined Contrary as its first employee and helped grow the firm from the ground up to more than $250 million in AUM. Early-stage companies Will was responsible for backing now have a combined market capitalization of over $10 billion.

    Sponsors:

    Juniper Square:

    Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

    AlphaSense:

    AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

    AlphaSummit Discount Code: AS26HII50

    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

    Stay Connected with Will Robbins:

    LinkedIn:https://www.linkedin.com/in/whrobbins/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Why VC Brands May No Longer Matter (5:05) What Happens to Seed Rounds When Software Gets Cheap? (10:40) How Two 17-Year-Olds Built Zepto (16:00) Why College Dropout Founders Keep Producing Outliers (21:53) What Will Looks for in Exceptional Founders (23:52) Can You Actually Identify the Founder “X Factor”? (29:20) The Founder Signal That’s Almost Impossible to Fake (41:11) Which Business Models Create Venture’s Biggest Outcomes? (54:41) Why So Many Great Startups Pivot

    E437: Doug Beyer on Raising Capital, LP Psychology & GP Stakes Oct 02, 2026
    Show notes

    What if the biggest opportunity in private markets isn’t backing companies—but backing the next generation of investment firms? In this episode, I sit down with Douglas Beyer, managing partner and founder of Roaring Brook Holdings, to discuss why emerging managers remain one of the most undercapitalized opportunities in alternative assets. Douglas explains how anchor capital changes fundraising dynamics, why LP relationships determine whether firms survive, and how the best emerging managers build trust through transparency and execution. We also explore GP seeding, organizational durability, and why fundraising momentum matters more than most managers realize.

    Highlights:

    • Why emerging managers face a structural capital gap
    • How anchor investors solve the “cold start” problem
    • Why LP relationships are built years before capital is deployed
    • The hidden importance of communication and transparency
    • How fundraising momentum determines fund survival
    • Why many great investors fail at building firms
    • The difference between raising capital and building a franchise
    • How secondary markets are reshaping private equity liquidity

    Guest Bio:

    Douglas Beyer is managing partner and founder of Roaring Brook Holdings, a firm providing seed, acceleration, and GP solutions to the next generation of private market investment firms. He spends his days evaluating opportunities where their capital, relationships, and strategic involvement can catalyze and improve the success of a firm.

    Sponsors:

    Juniper Square:

    Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

    AlphaSense:

    AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

    AlphaSummit Discount Code: AS26HII50

    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

    Stay Connected with Douglas Beyer:

    LinkedIn:https://www.linkedin.com/in/douglas-beyer-2944bb1a/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Why He Left a Prestigious Family Office to Back Emerging GPs (2:00) The Hidden Value Most Investors Miss in Asset Management Firms (5:27) Why LP Relationships Matter More Than Most GPs Realize (9:10) The Gold Standard for Managing LP Communication (14:08) The Anchor Investor Problem Breaking Emerging Managers (17:23) The Silent Risk LPs Fear Most in New Funds (22:26) Why the Best GPs Add Value Before Asking for Capital (29:26) Why Emerging Managers Still Matter in a Mega-Fund World (34:17) The One Thing Every New Fund Needs to Survive

    E436: Nnamdi Okike on Billionaires, Founder Psychology & the Venture Capital Bubble Sep 30, 2026
    Show notes

    Can venture capital really be turned from instinct into science? Nnamdi Okike is Co-Founder and Managing Partner of 645 Ventures, where he leads Seed and Series A investments in software and software-enabled companies. We discuss why Nnamdi believes venture investing is driven by the totality of an investor’s experiences rather than pure instinct, how 645 quantifies founder qualities, and why missionary and “non-central casting” founders can become exceptional investments. We also explore why startups need the right market inflections, how stablecoins and agentic commerce are reshaping fintech, what Nnamdi has learned across five fund vintages, and why raising too much capital at Seed can actually hurt a company.

    Highlights:

    • Why venture investing may be more science than instinct
    • How 645 Ventures quantifies founder potential
    • Why Nnamdi prefers missionaries over mercenaries
    • What separates “non-central casting” founders
    • Why great founders still need the right market inflection
    • Why VCs can mistake themselves for the customer
    • How to tell whether founder confidence is actually justified
    • Why stablecoins could transform global financial infrastructure
    • How AI and programmable money could enable agentic commerce
    • Why market cycles should influence venture deployment
    • Why patience and truth-seeking are core values at 645 Ventures
    • Why massive Seed rounds can damage startup culture

    Guest Bio:

    Nnamdi Okike is Co-Founder and Managing Partner of 645 Ventures, where he partners with founders building vertical and horizontal software and software-enabled companies. 645 Ventures leads Seed and Series A rounds and works closely with exceptional teams as they scale toward the growth stage.

    Sponsors:

    Juniper Square:

    Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

    AlphaSense:

    AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

    AlphaSummit Discount Code: AS26HII50

    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

    Stay Connected with Nnamdi Okike:

    LinkedIn:https://www.linkedin.com/in/nnamdiokike/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Why Venture Investing Isn’t About Instinct (3:36) How 645 Quantifies Founder Potential (5:41) Why the Best Founders Think Differently (9:14) What Really Predicts an Exceptional Founder (13:29) The Inflection Points Behind Great Startups (17:35) The Hidden Failure Mode in Early-Stage Investing (23:51) Why Harder Markets Require Different Founders (31:53) Where Fintech’s Next Opportunities Are Emerging (44:38) The Biggest Lessons From Four Venture Funds (57:03) Why Too Much Seed Capital Can Hurt Startups

    E435: Why Most Companies Aren’t Ready for AI Sep 28, 2026
    Show notes

    Which competitive moats will actually survive the AI era? SC Moatti is Managing Partner at Mighty Capital and Board Chair at Products That Count. We break down what Mighty Capital learned from mapping 550 companies by defensibility, why traditional SaaS advantages like switching costs and data moats may be weakening, and why network effects and counter-positioning are emerging as powerful AI-era moats. We also discuss why SC disagrees with the conventional power-law approach to venture, how AI is transforming M&A and corporate innovation, the Product Alpha Effect behind Mighty Capital’s investment strategy, and what venture firms must change to survive the AI transition.

    Highlights:

    • What Mighty Capital learned from analyzing 550 companies
    • Why traditional SaaS moats may no longer work in AI
    • Why network effects and counter-positioning are gaining importance
    • Why the IPO threshold may now be closer to $30–50 billion
    • Why SC disagrees with the conventional power-law approach to venture
    • How AI is shifting M&A from financial engineering to product innovation
    • Why the best companies treat leaders like resource allocators
    • How the Product Alpha Effect turns product innovation into investment alpha
    • How Mighty Capital uses signals from 600,000 product builders
    • The two metrics SC believes investors should watch in AI companies
    • Why AI could force companies to reinvent distribution
    • Which venture capital firms could survive the AI transition

    Guest Bio:

    SC Moatti is Managing Partner at Mighty Capital and Board Chair at Products That Count. She co-founded Mighty Capital around the Product Alpha Effect, a data-backed framework for investment outperformance, and has invested in companies including Amplitude, Netskope, and Groq. Earlier in her career, SC built products at Meta and Siebel Systems and authored an award-winning book on what makes a great product. She is a Stanford GSB alum, Kauffman Fellow, YPO member, and graduate of CentraleSupélec.

    Sponsors:

    Juniper Square:

    Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

    AlphaSense:

    AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

    AlphaSummit Discount Code: AS26HII50

    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

    Stay Connected with SC Moatti:

    LinkedIn:https://www.linkedin.com/in/scmoatti/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Which Moats Actually Survive AI? (1:37) How SC Stays Disciplined on Valuation (4:55) Why Power-Law Investing Can Become a Constraint (6:32) How AI Is Rewriting the M&A Playbook (14:11) The Product Alpha Effect Behind Mighty Capital (17:47) The Two AI Metrics Investors Should Watch (21:43) Why AI Could Reinvent Distribution (24:11) What Makes a Great Product in the AI Era? (30:30) Which Venture Firms Will Survive AI? (36:20) The Advice SC Would Give Her Younger Self

    E434: Warren Gibbon on How AI is Changing the Private Markets Sep 25, 2026
    Show notes

    Are private markets still positioned to outperform public markets? Warren Gibbon is a Multi-Family Office Chief Investment Officer with deep experience across asset allocation, equity research, and portfolio management. We discuss why investors may need to re-underwrite their assumptions about private markets, how higher rates and growing competition have changed private equity, and why public-market earnings growth may be underappreciated. Warren also explains why he is more constructive on venture, what he looks for in emerging managers, the risks created by passive investing, and how he would deploy $100 million of fresh capital today.

    Highlights:

    • Why investors should re-underwrite the case for private markets.
    • What the endowment model’s historical returns may be hiding.
    • Why Warren believes public-market value creation is underestimated.
    • The risk behind today’s massive AI infrastructure spending boom.
    • Why private equity faces a much harder environment going forward.
    • How passive investing may be changing the behavior of public markets.
    • Why “boring and hard” investments can remain structurally underfunded.
    • How Warren would deploy $100 million of fresh liquidity today.

    Guest Bio:

    Warren Gibbon is a Multi-Family Office Chief Investment Officer with 14 years of investment management experience and a focus on U.S. and global equities. His expertise spans asset allocation, equity research, portfolio management, investment analysis, and valuation, with additional interests in behavioral finance and the construction of diversified portfolios across public and private markets.

    Sponsors:

    Juniper Square:

    Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit junipersquare.com/howiinvest.

    AlphaSense:

    AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit alpha-sense.com/howiinvest to learn more.

    AlphaSummit Discount Code: AS26HII50

    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

    Stay Connected with Warren Gibbon:

    LinkedIn:https://www.linkedin.com/in/warren-gibbon-cfa/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Will Private Markets Still Outperform? (4:00) Is the AI Spending Boom Sustainable? (7:00) Why Warren Is Cautious on Private Equity (13:00) Why Venture May Be More Attractive Today (18:00) Why “Boring and Hard” Can Be a Great Investment (21:00) Is Passive Investing Breaking the Market? (27:00) Why Liquidity Could Become Your Biggest Advantage (31:00) The Problem With Portable Alpha (34:00) How Warren Thinks About Venture’s Top Firms (40:00) How He Would Invest $100 Million Today

    1 2 3 45 Next

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