Podcast
How I Invest with David Weisburd
Hosted by David Weisburd · EN
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.
312episodes
Episodes
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E355: From Deal-by-Deal to a $6.5B Platform: Building a Real Estate Investment Empire
Apr 2400:28:40Summary readyWhat if the best investments aren’t found in chaos—but in having the discipline to act when others can’t? In this episode, I sit down with Darren Fisk, Founder of Forum Investment Group, to discuss how he scaled from early syndication deals to a fully integrated multifamily investment platform managing billions. Darren breaks down how he leaned in during the 2008 financial crisis to acquire 9,000 units, why focusing on distressed capital structures rather than distressed assets created asymmetric opportunities, and how flexibility across the capital stack allows investors to generate returns in any market. Highlights: How buying distressed capital stacks created outsized returns in 2008 Why conviction matters more than timing in volatile markets The difference between allocating capital and truly investing How flexibility across debt and equity drives consistent returns Why the best opportunities are often “below the headline” The hidden advantage of operating assets, not just owning them Why doing nothing can be the highest returning decision How market cycles create obvious opportunities most investors miss Guest Bio: Darren Fisk is the Founder of Forum Investment Group, a multifamily-focused investment platform with over two decades of experience across real estate equity, debt, and structured finance. He built the firm from early syndication deals into a fully integrated asset manager investing up and down the capital stack. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. . We’d like to thank AlphaSense for sponsoring this episode! Sponsor: 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. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Darren Fisk: LinkedIn:https://www.linkedin.com/in/dfiskforumre/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: Forum is an SEC-registered investment adviser; however, such registration does not imply a certain level of skill or training. The views expressed are for general informational purposes only, do not take into account the specific investment objectives, financial situation, or needs of any individual, and may not be representative of any specific investment, strategy, or client experience. This communication is for informational purposes only and does not constitute investment advice, a recommendation, or part of any offering materials. Any investment will be made solely through formal offering materials provided by Forum or its affiliates. Investing involves a high degree of risk, including possible loss of entire investment. Investors must rely on their own examination of any transaction and its terms, including all merits and risks involved. These securities have not been recommended or approved by any federal or state securities authority, nor have such authorities passed upon the accuracy or adequacy of this communication. This communication contains forward-looking statements based on current expectations, not prior operating history. Such statements are not guarantees of future performance and involve risks, uncertainties, and assumptions that are difficult to predict. Actual outcomes may differ materially from any forward-looking statements made herein. Investment should only be made by individuals who understand the nature of these transactions and can bear the associated risks. (0:00) How He Bought 9,000 Units While Everyone Else Was Panicking (1:18) The Reputation Edge That Let Him Move in a Crisis (2:27) Why Conviction Matters More Than Confidence in a Downturn (4:32) Why Great Investors Refuse to Be “Allocators” (6:14) The Hidden Opportunity Most People Miss in Bad Markets (9:34) Why He Abandoned Deal-by-Deal Investing for Good (12:13) The Mistake He Made Building the Wrong Fund Structure (15:20) How He Built a Team That Could Scale Beyond Him (22:22) Why Doing Nothing for 6 Years Was the Right Move (27:08) The One Thing He Wishes He Built Much Earlier
Summary
E354: Why Most VCs Misunderstand Peter Thiel’s Power Law
Apr 2300:47:41Summary readyWhat if venture capital isn’t about finding unicorns—but about consistently making good investments? In this episode, I sit down with Eric Scott, Co-Founder and Managing Partner at Overlook Capital, to discuss how his approach to venture evolved from chasing power laws to focusing on fundamentals. Eric explains why most venture frameworks only make sense in hindsight, how thinking like a value investor can improve early-stage decision-making, and why founder quality is ultimately revealed through execution, not narratives. We also explore concentrated markets, late-stage venture dynamics, and how reputation, conviction, and timing shape outcomes across cycles. Highlights: Why venture “power laws” don’t help you pick winners in real time How value investing principles apply to early-stage companies What most investors misunderstand about founder selection Why great companies don’t come from A/B testing alone How venture markets became structurally concentrated Why smaller funds can outperform in overlooked segments The hidden role of reputation and signal in fundraising Why being wrong—and correcting it—is a core investing skill Guest Bio: Eric Scott is Co-Founder and Managing Partner at Overlook Capital, where he focuses on investing in category-leading growth companies. He previously worked at Founders Fund and 8VC, gaining experience across early and growth-stage investing, and has also held roles in healthcare and technology startups. Eric began his career after founding a company out of college and brings a cross-functional perspective shaped by both operating and investing experience. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: 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. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Eric Scott: LinkedIn: https://www.linkedin.com/in/eric-scott-bio/ 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) The One Sentence From Peter Thiel That Changed How He Invests (2:28) Why Venture Capital Might Be Built on a Flawed Idea (4:59) Are Startups Built on Movements or Real Businesses? (8:31) Why Every Great VC Invests Completely Differently (10:40) The Rule That Changed How Founders Fund Picks Winners (12:03) If You’re Firing Founders, You Already Made a Mistake (16:43) What Actually Makes a “Great” Founder (It’s Not What You Think) (22:58) The Story That Redefines What Conviction Really Looks Like (30:14) Why Chasing Billion-Dollar Ideas Is the Wrong Strategy (40:41) The Hidden Game Behind Who Gets on the Cap Table
Summary
E353: Why Biotech Is Struggling in Today’s Market (and the Future of Healthcare)
Apr 2200:33:13Tap to summarizeWhat if the biggest opportunity in healthcare isn’t new drugs—but reinventing how the entire system works? In this episode, I sit down with David Berry, Founder of over 20 companies including seven $1B+ businesses, to discuss why the traditional biotech model is breaking and where the next wave of innovation in healthcare is emerging. David explains how pricing pressure, rising costs, and global competition are compressing returns in drug development, while AI, data, and new business models are unlocking entirely new ways to deliver care. We also explore how technology is transforming clinical trials, why healthcare is shifting beyond pharmaceuticals, and how investors can find opportunity in mispriced parts of the market. Highlights: Why biotech returns are structurally declining despite innovation How AI is changing clinical trials and drug development timelines The unappreciated impact of China on global biotech competition Why healthcare is a $5T opportunity beyond pharmaceuticals How data and longitudinal patient insights unlock new discoveries The next frontier in longevity, wearables, and personalized health Why the middle stage of venture is undercapitalized today How supply-demand imbalances create the best investment opportunities Guest Bio: David Berry is a founder, entrepreneur, and investor who has built over 20 companies, including seven valued at over $1 billion. He spent nearly two decades at Flagship Pioneering, where he helped create and scale leading biotech companies, and later founded Valo Health. He is now the founder of Averin Capital, where he focuses on the technology-driven transformation of healthcare and investing in companies at the intersection of biology, data, and innovation. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: 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. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with David Berry: LinkedIn: https://www.linkedin.com/in/davidberrymdphd/ 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 Biotech Returns Are Quietly Breaking (0:15) The Hidden Shift Making Life Sciences More Attractive (1:00) Why Drug Prices Are Falling—and Innovation With It (3:22) The Unintended Consequence: Fewer New Drugs (4:17) Why Investors Are Choosing Rockets Over Biotech (5:38) China Is Becoming the World’s Drug Factory (8:06) The $5 Trillion Opportunity Most Investors Miss in Healthcare (9:43) Why AI Could Cut Years Off Drug Development (13:41) The Hidden Flaw in How We Test Drugs Today (21:31) How He Raised $450M in One of the Hardest VC Markets
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E352: JD Vance’s Co-Founder on Space Defense, Hard Tech, and the Biggest Opportunities Ahead
Apr 2100:38:01Tap to summarizeWhat if the best venture returns come from avoiding trends—not chasing them? In this episode, I sit down with Colin, Co-Founder of Narya, to discuss how he approaches investing in frontier sectors without falling into mimetic behavior. Colin explains why the best opportunities are often “hidden in plain sight,” how mission-driven investing can still generate venture-scale returns, and why concentration, not diversification, drives outcomes in venture. We also explore defense, space, and advanced manufacturing, and how timing, business model innovation, and founder quality ultimately determine success. Highlights: Why chasing popular sectors often leads to worse outcomes How to identify “hidden in plain sight” opportunities Why venture returns are driven by a few concentrated bets What most investors misunderstand about deep tech investing How mission-driven companies can still deliver top-tier returns Why too much capital can hurt startups more than help The traits that define world-changing deep tech founders Why business model innovation matters as much as technology Guest Bio: Colin is a Co-Founder of Narya, where he focuses on investing in early-stage companies across sectors such as defense, healthcare, and advanced manufacturing. He previously served as a Managing Director at Mithril and held senior roles across leading venture platforms, investing in companies spanning biotechnology, neuroscience, and enterprise software. Colin also serves as an advisor to multiple investment and accelerator platforms, and has built a career backing founders working on complex, high-impact problems. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: 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. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Colin Greenspon: LinkedIn: https://www.linkedin.com/in/colingreenspon/ 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) What Made JD Vance a Dangerous (and Different) Investor (2:20) Can You Invest in Innovation Without Losing Money? (5:47) Why Most “Contrarian” Investors Are Actually Late (8:54) The Hidden Mistake LPs Make With Diversification (10:44) Why Billionaires Back New VC Funds (It’s Not Returns) (14:00) Why the Best Companies Don’t Follow Categories (19:09) Why Space Is Becoming the Next Battlefield (24:09) What Separates World-Changing Founders From Everyone Else (27:00) Why Too Much Capital Kills Great Companies (43:02) The Career Mistake That Slows Most Investors Down
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E351: Why Most Family Offices Fail (And How a16z Fixed It)
Apr 2000:38:16Tap to summarizeWhat if the biggest edge in investing isn’t picking better assets—but structuring them better for taxes, incentives, and control? In this episode, I sit down with Michel, Founding CIO of a16z Perennial, to discuss how institutional investing frameworks translate to individual portfolios. Michel breaks down why most wealth management fails at true investment management, how misaligned incentives shape outcomes, and why scale, access, and structure matter more than traditional asset allocation. We also explore concentrated portfolios, tax alpha, and how psychology ultimately determines whether a strategy succeeds or fails. Highlights: Why wealth management and investment management are fundamentally different How scale actually benefits LPs, not just GPs What most investors misunderstand about diversification Why a 90/10 portfolio may not be irrational for the right investor How tax alpha can outperform investment alpha The hidden cost of fund-of-funds and fee layering Why access to top managers drives most institutional returns How psychology, not strategy, determines long-term outcomes Guest Bio: Michel is the Chief Investment Officer at a16z Perennial, where he leads multi-asset portfolio construction for founders and large individual investors. Prior to a16z, he was CIO at Jordan Park, managing approximately $17 billion across global asset classes, and a Managing Director at Makena Capital Management. Earlier in his career, he worked at Scion Capital and McKinsey, and holds advanced degrees from Stanford and Cambridge, including a PhD in Management Science and Engineering as a DARPA fellow. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: 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. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Michel Del Buono: LinkedIn: https://www.linkedin.com/in/mdelbuono/ 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 A16Z Built a Family Office (It Wasn’t for Wealth) (1:26) The Hidden Problem With Single Family Offices (4:51) Does Scale Help or Hurt Investment Returns? (6:49) The Incentive Problem That Breaks Wealth Management (9:06) Why Taxable Investors Are Suddenly So Important (11:15) The First Principles Behind Building a Modern Family Office (15:35) Why All Endowment Portfolios Look the Same (19:05) The “Crazy” Portfolio That Might Actually Be Rational (24:19) Why Investing Is More Psychology Than Strategy (36:53) The Easiest Alpha Most Investors Completely Ignore
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E350: How Family Offices Quietly Build Generational Wealth
Apr 1700:31:32Tap to summarizeIs the real edge in investing not picking assets but structuring how you allocate capital? Terence Thompson is a Vice President of Investments at DF Enterprises, about how single family offices think about portfolio construction, liquidity, and structural alpha. We break down why Terry uses a total portfolio approach, how family offices create edge through flexibility, and why being a liquidity provider during market stress is one of the most powerful strategies. We also discuss concentration risk in public markets, the evolution of private markets, and how allocators can think about illiquidity, secondaries, and niche opportunities. Highlights: Why single family offices have a structural edge over multifamily offices Total portfolio approach vs traditional asset allocation Competing strategies for capital across the portfolio Why liquidity is critical during market dislocations Concentration risk in large cap equities Structural changes in small cap and private markets The impact of retail capital flowing into private equity How misaligned liquidity structures can hurt returns Where illiquidity premium still exists Underrated opportunities in small buyout and niche credit The role of behavioral bias in asset allocation Why risk tolerance should match the capital base Guest Bio: Terence Thompson is a Vice President of Investments at DF Enterprises, a single family office where he oversees investment strategy, portfolio construction, and manager selection across public and private markets. He has over a decade of institutional investment experience, including managing assets at Blue Cross Blue Shield of Arizona. Terry is a CFA charterholder, USAF veteran, and an active member of several investment and policy organizations. He focuses on building resilient portfolios that balance liquidity, risk, and long-term compounding. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: 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. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Terence Thompson: LinkedIn:https://www.linkedin.com/in/terencemthompson/ 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) What Gets Lost When a Family Office Serves Too Many Families (2:00) Why the Traditional Endowment Model Isn’t Flexible Enough Anymore (2:45) The Hidden Force Behind Today’s Momentum Trades (6:29) Why Passive Investing May Be Riskier Than It Looks (13:28) Why Retail Capital Will Change Private Markets in a Big Way (16:31) The Structural Flaw That Could Hurt Retail Investors (19:29) Is the Illiquidity Premium Still Real? (21:18) Why Small Buyout May Benefit Most From the Retail Wave (23:41) The Most Underrated Asset Classes Right Now (30:24) The Career Advice That Matters More Than Playing It Safe
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E349: Built to Scale: The J.P. Morgan Growth Playbook
Apr 1600:32:56Tap to summarizeWhat if the biggest edge in venture today isn’t picking companies—but owning the entire lifecycle of capital? In this episode, I sit down with Paris Heymann, Co-Managing Partner of Technology Investing at J.P. Morgan Private Capital, to discuss how the boundaries between public and private markets are breaking down. Paris explains why companies are staying private longer, how value is increasingly accruing to private investors, and why multi-stage platforms are becoming the new model for capturing returns. We also explore how AI is shifting business models from selling software to selling work, why founder quality still drives outcomes, and how power laws continue to dominate both private and public markets. Highlights: Why the line between public and private markets is disappearing How J.P. Morgan competes using platform, not just capital Why companies are staying private for 15+ years What changes when companies start selling “work” instead of software Why valuation matters less than quality and compounding How power laws dominate even in growth and public markets Why founder-market fit matters more than ever in AI The real advantage of multi-stage investing platforms Guest Bio: Paris Heymann is Co-Managing Partner for Technology Investing within J.P. Morgan Private Capital, a division of J.P. Morgan Global Alternatives in J.P. Morgan Asset Management. Paris joined Private Capital from Index Ventures in 2024 where he served as Partner and helped to establish the firm’s New York office. Before Index, Paris was Partner at Arena Holdings where he invested globally in public and private technology companies. He began his career at Bain Capital within the North American Private Equity group. Paris holds a B.A. in Political Economy from Williams College. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank @AlphaSense for sponsoring this episode! Sponsor: 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. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Paris Heymann: LinkedIn:https://www.linkedin.com/in/paris-heymann/ 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 JP Morgan Has a Hidden Edge in Venture (0:47) When Capital Alone Isn’t Enough to Win Deals (2:18) Why the Venture Model Is Quietly Breaking (3:48) Should the Best Companies Ever Go Public? (5:40) The Real Reason Founders Stay Private Longer (7:38) What “Growth Equity” Actually Means Today (8:39) Why AI Demand Is Exploding Faster Than Anyone Expected (10:09) Why Selling “Work” Will Replace Selling Software (11:30) Why Data Moats Might Be Less Valuable Than You Think (13:40) Why Expensive Companies Can Still Be Cheap
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E348: Why “Boring” Businesses Beat Venture Capital
Apr 1500:26:43Tap to summarizeIs private equity alpha really about picking great deals—or about executing the same playbook better than everyone else? In this episode, I discuss with Monty Yort, Managing Partner at GenNx360 Capital Partners, about how disciplined execution and consistency drive long-term outperformance in private equity. We break down how GenNx360 approaches proactive sourcing, why lower middle market investing creates structural advantages, and how operational improvement and buy-and-build strategies compound value over time. Monty also shares lessons on leadership, mentorship, and why the best firms continuously refine their process rather than chase new strategies. Highlights: Why proactive sourcing leads to better deals and more opportunities The shift to industrial services and fragmented markets Buy-and-build as a repeatable value creation strategy Why organic growth is the primary driver of returns How to evaluate founders and build leadership teams The importance of discipline in fund size and strategy Why continuation funds extend the best investments How repetition and consistency outperform complexity The role of mentorship in accelerating careers Why private equity is about people as much as process Guest Bio: Monty Yort is a Managing Partner at GenNx360 Capital Partners, a New York–based private equity firm with $2.5 billion in assets under management focused on middle-market industrial and business services companies. He has more than two decades of experience leading acquisitions and recapitalizations totaling over $3 billion, specializing in operational improvement and growth in fragmented industries. Prior to joining GenNx360 in 2009, Monty was a Managing Partner at Schroder Ventures and a Principal at Aurora Capital Group, with earlier roles at Morgan Stanley and Salomon Brothers. He holds an MBA from UCLA Anderson and serves on multiple portfolio company boards Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: 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. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Monty Yort: LinkedIn:https://www.linkedin.com/in/monty-yort-8236043/ 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 Private Equity Doesn’t Need Power Laws to Win (1:09) Proactive and AI-driven sourcing strategies (5:57) AI's impact on industries and investment strategies (6:55) History, evolution, and fund strategy at Genexx (9:25) Capital markets, continuation vehicles, and fund challenges (13:16) Leadership, management, and upscaling portfolio teams (17:19) Friction in investing and selling businesses (18:48) Lower middle market and future of private equity (23:37) Motivations and advice for private equity professionals (26:28) Closing remarks
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E347: The $26B CIO Who Turned Superforecasting Into Alpha
Apr 1400:38:39Summary readyHow do you manage a $26 billion public fund while keeping every investment decision disciplined, every team member calibrated, and every partner accountable? In this episode, I sit down with Mark Steed, Chief Investment Officer of AZ Public Safety Personnel Retirement System, to explore how super forecasting and probabilistic thinking shape portfolio management. Mark shares how lessons from Dr. Phil Tetlock's the Good Judgment Project inform every investment decision, why intellectual humility and calibrated confidence drive better outcomes, and how simplifying portfolios into broad buckets creates flexibility and competition for capital. He also unpacks the role of co-investments, structural alpha, and first principles thinking in public markets. Highlights: How PSPRS uses probabilistic forecasts and Briar Scores to track accuracy and improve decision-making Why intellectual humility and calibration are as important as market knowledge Simplifying complex portfolios into three broad buckets: capital appreciation, contractual income, and diversifying strategies The growing role of co-investments and capturing structural alpha with trusted partners Benchmarking against the S&P 500 while managing expectations for thousands of police and fire pensioners Distinguishing between “investing,” “allocating,” and truly “owning” assets Lessons from super forecasting on evaluating GPs and reducing overconfidence in a complex market environment Guest bio: Mark Steed is Chief Investment Officer of AZ Public Safety Personnel Retirement System, overseeing approximately $26 billion for police and fire pensions. He has implemented super forecasting and probabilistic investment methodologies at scale, transforming decision-making, portfolio construction, and team dynamics. Known for his focus on calibration, intellectual humility, and first principles thinking, Mark combines behavioral science with traditional investment rigor to deliver disciplined, long-term results. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: 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. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Mark Steed: LinkedIn:https://www.linkedin.com/in/mark-steed/ 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) Introduction (6:14) Improving team calibration and reducing overconfidence (7:14) Distinguishing innovation from craziness; building team forecasting calibration (9:20) Parallels with Bridgewater’s principles and team dynamics (13:13) Benchmarking against the S&P 500 and implications for portfolio management (14:29) Challenges of managing portfolios for police and firemen (16:02) Simplifying portfolio construction into broad categories (17:27) Flexibility and competition among investment ideas (19:08) Independent approaches and thoughts on TPA (22:16) Evolution of co-investment strategy and structural alpha (24:02) Semantics of investing: Allocation vs. ownership (25:58) Recent changes in investment mindset (27:24) The performative aspect of confidence in investments (29:38) Uncertainty in predicting AI and interest rates (33:06) Forcing super forecasting on GPs (34:54) Timeless advice for young investors (36:16) Handling spiky asset classes like venture capital (38:17) Closing remarks
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E346: $7 Billion CIO: Why the Endowment Model is Changing
Apr 1300:34:43Summary readyHow do you build a $7 billion portfolio that performs across decades while keeping every client aligned and every manager motivated? In this episode, I sit down with Karen Welch, Chief Investment Officer at Spider Management Company, to explore the evolving role of a CIO in today’s complex investment landscape. Karen shares how lessons from Stanford’s endowment shaped her approach, why the best investment edge comes from people and relationships, and how Spider leverages both to generate top-tier returns. She also unpacks how to navigate private markets, assess the illiquidity premium, and structure portfolios to balance opportunity with risk. Highlights: Why the most important skill for investors isn’t modeling—it’s building relationships with teams and managers How AI is reshaping portfolio management and why human judgment remains critical Playing offense and defense in a portfolio: spotting dislocations and leaning into opportunities Lessons from the endowment model: what still works, what needs evolution, and why illiquidity premiums aren’t guaranteed Strategies for accessing top-tier venture managers without decades of reputational capital The advantages of Spider’s single portfolio model across multiple clients and the “razor” it creates for disciplined investing Practical advice for career longevity: loving your work and balancing networking with building something meaningful Guest bio: Karen Welch is Chief Investment Officer at Spider Management Company, overseeing approximately $7 billion for the University of Richmond and affiliated nonprofit partners. Previously, she spent nearly a decade at Stanford’s endowment, where she honed her approach to portfolio construction, manager selection, and long-term investing. Known for her focus on relationships, strategic thinking, and disciplined portfolio management, Karen combines decades of endowment experience with a modern approach to private and public markets. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: 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. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Karen Welch: LinkedIn:https://www.linkedin.com/in/karen-horn-welch/ 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) The Most Important Lesson From Stanford Wasn’t Investing (1:07) Why AI Won’t Replace the Best Investors (2:28) What a CIO Actually Does (Most People Get This Wrong) (3:30) What “Monitoring a Portfolio” Really Means (5:26) How the Best CIOs Find Opportunities Before Everyone Else (7:30) Why the Best Investments Hide Behind Bad Headlines (8:31) What’s Broken in the Endowment Model Today (13:16) The Truth About the Illiquidity Premium (It’s Not Real) (15:58) Why Access Matters More Than Skill in Venture (23:08) The Hidden Power of Running One Single Portfolio
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