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.
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Episodes
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E386: Adams Street ($70B): Venture Capital Has a New Problem
Yesterday00:38:42Summary readyWhat separates the venture investors who generate extraordinary returns from those who simply participate in the asset class? In this episode, I sit down with Jeff Diehl, Managing Partner and Head of Investments at Adams Street Partners, one of the world's largest private markets investors with more than $70 billion in assets under management. Jeff shares lessons from over four decades of venture investing, including why access to top managers matters more than almost anything else, what 14,000 realized venture exits have taught Adams Street about return generation, and why portfolio construction often matters more than stock picking. Highlights: Why access to top-quartile venture managers is the single most important factor in venture investing The data behind venture capital's unmatched persistence of returns What Adams Street learned from nearly 14,000 realized venture-backed company exits Why just 7% of companies generated 100% of venture gains The critical role of portfolio construction and time diversification How Adams Street uses co-investments and secondaries to increase exposure to breakout winners Why venture capital succession planning is notoriously difficult The relationship between incentives, culture, and long-term investment performance Whether venture capital is becoming more concentrated among a handful of mega-firms Why private markets continue to capture a growing share of global growth opportunities Jeff's most expensive investing lesson and why mistakes are essential for becoming a great investor Guest Bio: Jeff Diehl is the Managing Partner and Head of Investments at Adams Street Partners, a global private markets investment manager with more than $70 billion in assets under management across private equity and private credit strategies. He oversees the firm's investment activities and overall management while serving as Chairman of both the Portfolio Construction Committee and Executive Committee. Under his leadership, Adams Street has expanded its global footprint to more than 330 professionals across 14 offices worldwide. 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 Pierce: https://www.weisburdpierce.com/ Stay Connected with Jeff Diehl: LinkedIn: https://www.linkedin.com/in/jeffrey-diehl-63a0701/ 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) The Two Rules That Explain Almost Every Venture Outcome (0:43) Why Venture Capital Has More Persistence Than Any Other Asset Class (5:01) What 14,000 Exits Taught Him About Venture Returns (7:57) The Shocking Reality: 7% of Companies Create 100% of the Gains (9:22) Why Every Great Venture Co-Investment Starts With GP Relationships (10:33) The Hidden Reason Growth Investors Are Moving Into Private Markets (13:11) Why Succession Fails at Most Venture Capital Firms (16:23) The Culture and Incentive System Behind Top Investment Organizations (24:59) Can Size Become a Moat in Venture Capital? (33:53) The $12 Million Mistake He Still Keeps as a Reminder
Summary
E385: Why Public Markets Need SpaceX, OpenAI & Anthropic
2d ago00:27:51Summary readyWhat if the biggest opportunity in private markets isn’t finding the next startup—but owning the next public company years before it ever rings the bell? In this episode, I sit down with Matt Witheiler, Head of Late-Stage Growth at Wellington Management, to discuss how the line between public and private markets continues to blur. Matt explains why companies are staying private longer, why public investors are starved for growth, and how late-stage investing differs from both venture capital and public equities. We also explore IPO markets, valuation discipline, liquidity dynamics, and why the best companies often justify paying up for quality. Highlights: Why OpenAI, Anthropic, and SpaceX may reignite the IPO market The growing shortage of high-growth companies in public markets Why small-cap investing has fundamentally changed over the last decade How late-stage investors evaluate hype versus fundamentals Why founders optimize for partners, not the highest valuation The advantage Wellington brings as both a private and public market investor Why valuation discipline matters more than bargain hunting Matt’s biggest investing miss and what SpaceX taught him about exceptional founders Guest Bio: Matt Witheiler is the Head of Late-Stage Growth at Wellington Management, where he leads the firm’s private company investing activities across technology, healthcare, consumer, and financial services. Since joining Wellington in 2016, he has helped build one of the largest and most respected late-stage growth investing platforms, leveraging the firm’s deep public market expertise to identify future public company leaders. Prior to Wellington, Matt was a General Partner at Flybridge Capital Partners and earlier held operating roles in technology, including co-founding AnandTech.com. He has been named to the Forbes Midas List for six consecutive years and is widely recognized as one of the leading investors at the intersection of 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 Pierce: https://www.weisburdpierce.com/ Stay Connected with Matt Witheiler: LinkedIn: https://www.linkedin.com/in/mwitheiler/ 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 the Biggest IPOs in History Won’t Break Public Markets (2:22) The Passive Buying Wave Coming for SpaceX, OpenAI, and Anthropic (3:15) Why Public Investors Are Desperate for New Growth Stories (5:22) How Investors Separate Real AI Companies From AI Hype (7:59) Why Pension Funds Are Buying Private Assets From Public Allocations (9:20) The Hidden Reason Small-Cap Investing Stopped Working (13:13) Why the Best Founders Want to Stay Private Longer (13:44) How Wellington Wins Deals Against Sequoia and Andreessen (18:38) The Secret to Getting Into the Hottest Rounds Before Everyone Else (24:42) The Billion-Dollar Mistake Wellington Made on SpaceX
Summary
E384: CEO of Commonfund on Venture Capital, Power Laws & the Future of IPOs
5d ago00:40:41Summary readyWhat if the biggest edge in venture capital isn’t manager selection—but earning access to the managers everyone already knows are the best? In this episode, I sit down with Mark Anson, CEO, President, and CIO of Commonfund, to discuss what he has learned managing capital across some of the world’s most influential institutions, including CalPERS, the Bass Family Office, and Commonfund. Mark explains why venture capital remains one of the most persistent alpha-generating asset classes, how LPs earn access to top managers, and why relationships, responsiveness, and knowledge-sharing matter more than check size. We also explore performance persistence, the illiquidity premium, co-investments, and the lessons Mark has learned managing capital across multiple decades and market cycles. Highlights: The surprising story of how donuts helped unlock access to a top-tier VC fund Why venture capital has the greatest performance dispersion in investing The difference between average and top-quartile venture returns How Commonfund evaluates emerging managers before the market finds them Why access in venture is earned, not bought The case for a rules-based approach to venture investing Why innovation is completely uncorrelated with the business cycle Mark’s framework for managing “human capital” throughout a career Guest Bio: Mark Anson is the Chief Executive Officer, President, and Chief Investment Officer of Commonfund, where he oversees more than $35 billion in assets serving endowments, foundations, and institutional investors. Throughout his career, Mark has led investment organizations at some of the world’s most prominent institutions, including CalPERS, the Bass Family Office, British Telecom Pension Scheme, Hermes Pension Management, and Nuveen Investments. A prolific author, researcher, and educator, he has published more than 100 journal articles and several leading finance textbooks, including The Handbook of Alternative Assets. 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 Anson: LinkedIn:https://www.linkedin.com/in/mark-anson-7a9b4a75/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: Each of CF Private Equity, Inc. and Commonfund OCIO, Inc. (collectively, “Commonfund”) is a registered investment adviser under the Investment Advisers Act of 1940. This material is solely for informational purposes and should not be viewed as a recommendation or an offer to sell or the solicitation to buy securities or adopt any investment strategy. The opinions expressed herein represent the current, good faith views of the participants at the time of publication, are not investment advice, and should not be relied upon as such. The information discussed herein has been developed internally and/or obtained from sources believed to be reliable; however, Commonfund does not guarantee the accuracy, adequacy, or completeness of such information. There is no assurance that any events or projections will occur, and outcomes may be significantly different than the opinions stated herein. This information, including any projections concerning financial market performance, is based on current market conditions, which will fluctuate and may be superseded by subsequent market events or for other reasons. (0:00) How a Box of Donuts Got CalPERS Into a Top VC Fund (2:35) Why Venture Capital Rewards Failure Differently Than Any Other Asset Class (4:20) The Power Law That Drives Nearly All Venture Returns (8:05) How Commonfund Wins Access to the Best Venture Managers (10:14) How Top LPs Can Approve Venture Deals in Just 48 Hours (11:50) The Secret Process for Finding Tomorrow’s Top VC Funds (15:10) Why Buying Into Carlyle Was Better Than Negotiating Lower Fees (18:37) Is Capital Still a Moat in Venture Capital? (24:38) Why the Biggest Investment Opportunities Happen Every 10 Years (33:31) The Hidden Cost of Companies Staying Private Too Long
Summary
E383:Why the Next Fortune 500 Companies Will Be Built on AI
6d ago00:32:13Summary readyWhat if the biggest investment opportunity of the next decade isn’t AI itself—but the companies building the infrastructure and workflows that allow AI agents to actually do work? In this episode, I sit down with David Blumberg, Founder and Managing Partner of Blumberg Capital, to discuss why he believes agentic AI is still in the first inning of a multi-decade transformation. David explains how AI agents will reshape productivity across industries, why vertical software companies with proprietary data have a major advantage, and how network effects are evolving through AI-powered data flywheels. We also explore the future of work, the rise of AI-native businesses, and why human relationships remain one of the few enduring advantages in an increasingly automated world. Highlights: Why agentic AI could become a larger market than software itself The hidden infrastructure needed for AI agents to transact autonomously How proprietary data creates durable AI moats Why vertical AI companies may outperform general-purpose models The concept of AI-powered data flywheels and compounding network effects How AI could dramatically increase productivity without eliminating opportunity Why the next generation of Fortune 500 companies is being built right now The enduring importance of relationships in a technology-driven world Guest Bio: David Blumberg is the Founder and Managing Partner of Blumberg Capital, an early-stage venture capital firm focused on backing visionary entrepreneurs building global B2B technology companies. Over a career spanning venture capital, operating leadership, and institutional investing, he has helped build and back category-defining businesses including Nutanix, Braze, DoubleVerify, Trulioo, and Check Point Software Technologies. Prior to founding Blumberg Capital, David held investment roles with Claridge, Apax Partners, Adler & Co., and T. Rowe Price, and was part of the early leadership team at Check Point. He is widely recognized for his focus on enterprise technology, cybersecurity, fintech, and the next wave of AI-driven 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 Blumberg: LinkedIn:https://www.linkedin.com/in/davidjblumberg 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 AI Agents Could Become the Biggest Productivity Shift in History (0:43) Will AI Create More Jobs or Eliminate Them? (5:10) The B2B AI Opportunity Most Investors Still Underestimate (8:07) Why Almost Nobody Uses AI Agents Today (And Why That’s About to Change) (9:22) The $100 Trillion Market Hidden Behind White-Collar Work (12:16) The Infrastructure Layer Every AI Agent Will Need (18:49) The Data Flywheel That Makes AI Companies Hard to Compete Against (20:46) Why Vertical AI Could Beat the Largest LLMs (24:45) The Surprising Opportunity Emerging Managers Have in the AI Boom (28:17) The Career Prediction From the 1970s That’s Finally Coming True
Summary
E382: Why Venture Capital Has a $3 Trillion Liquidity Problem
1w ago00:33:38Summary readyWhat if the biggest opportunity in venture today isn’t finding the next unicorn—but solving the liquidity problem created by companies staying private twice as long as they used to? In this episode, I sit down with Ravi Viswanathan, Founder and Managing Partner of NewView Capital, to discuss how the venture ecosystem is evolving beyond the traditional fund model. Ravi explains why he left NEA to build a firm focused on liquidity solutions, how company-led secondaries are becoming a critical tool for founders and employees, and why the future of venture may depend on balancing long-term ownership with thoughtful liquidity. We also explore the DPI drought, continuation vehicles, cap table management, and why relationships remain the ultimate source of edge in venture capital. Highlights: Why companies staying private longer created a structural liquidity gap The rise of company-led secondaries and founder-controlled liquidity How employee liquidity can improve retention and long-term alignment Why the venture industry can no longer ignore DPI The tension between FOMO investing and long-term conviction How continuation vehicles may reshape venture portfolios Why capital often masks product-market fit during boom cycles The relationship-driven lesson Ravi wishes he learned earlier in his career Guest Bio: Ravi Viswanathan is the Founder and Managing Partner of NewView Capital, a growth-stage investment firm managing more than $3 billion and focused on primary, secondary, and hybrid investments in leading technology companies. Prior to founding NewView in 2018, Ravi spent 15 years as a General Partner at NEA, where he backed category-defining companies including MuleSoft, Braintree, Acquia, Cyence, and GlobalLogic. Over more than two decades in venture capital, Ravi has built a reputation for partnering with exceptional founders, identifying enduring technology businesses, and helping shape the evolution of liquidity and capital formation in private 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 Ravi Viswanathan: LinkedIn:https://www.linkedin.com/in/raviswanathan/ 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 He Left NEA to Launch a $1.3 Billion Venture Fund (1:02) Are the Best Venture Companies Already Obvious by Series B? (3:33) The New Secondary Market Trend Reshaping Venture Capital (5:02) Why Employees Need Liquidity Long Before an IPO (7:03) The Hidden Benefits of Letting Employees Sell Shares (11:38) Will OpenAI, Anthropic, and SpaceX Fix Venture’s DPI Crisis? (13:17) Why Venture Capital May Never Return to Historical DPI Levels (20:18) Are Continuation Vehicles the Next Big Venture Trend? (24:35) The One Thing That Compounded Most Over 25 Years in Venture (28:20) How Easy Money Created an Entire Generation of Zombie Startups
Summary
E381: A16Z Partner: The Tax Strategy Hidden Inside Real Estate
1w ago00:48:54Summary readyWhat if the biggest inefficiency in investing today isn’t asset selection—but the fact that most investors still optimize for pre-tax returns instead of after-tax outcomes? In this episode, I sit down with Jeff Bramel, Partner at a16z Perennial, to discuss why real assets remain one of the most misunderstood areas of institutional investing. Jeff explains how structural diversification works beyond traditional portfolio theory, why private real estate behaves differently from public markets, and how tax efficiency can dramatically reshape long-term returns for taxable investors. We also explore opportunistic investing, portfolio construction, risk management, and why real estate may offer one of the largest remaining pockets of structural alpha. Highlights: Why after-tax returns matter more than headline returns The hidden inefficiencies inside private real estate markets How depreciation transforms the economics of taxable investing Why structural diversification matters more than historical correlations The problem with overly rigid institutional asset allocation models How opportunistic investing can add hundreds of basis points annually Why higher-return assets often become safer over long time horizons The overlooked relationship between taxes, compounding, and alpha Guest Bio: Jeff Bramel is a Partner at a16z Perennial, where he focuses on real assets and institutional portfolio construction. He has more than 25 years of experience managing large and complex investment portfolios across public and private markets, with expertise spanning real estate, infrastructure, energy, agriculture, asset-backed investments, and alternative strategies. Jeff is known for applying first-principles thinking to portfolio management, combining deep quantitative analysis with a focus on structural diversification, cash-flowing assets, and after-tax optimization for long-term investors. 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 Jeff Bramel: LinkedIn:https://www.linkedin.com/in/jeffbramel/ 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 Billionaires Quietly Move Into Real Estate (1:22) The Structural Reason Real Estate Diversifies Tech Wealth (5:07) The Hidden Tax Advantage Most Investors Still Don’t Understand (9:53) Why Private Credit Looks Much Worse After Taxes (18:36) The Real Meaning of “Opportunistic” Real Estate Investing (21:15) How Rigid Asset Allocation Quietly Destroys Returns (27:11) How Much Alpha Exists in Picking the Right Real Estate Deals? (30:59) Why Higher Volatility Can Actually Create Better Long-Term Returns (38:26) The Diversification Myth Most Wealthy Investors Believe (45:50) Why Real Estate Is a Quant Nerd’s Dream Asset Class
Summary
E380: How Billionaire Family Offices Actually Invest
1w ago00:45:52Summary readyWhat if the greatest threat to generational wealth isn’t bad investing—but the inability to think beyond the next liquidity event? In this episode, I sit down with Eric Becker, Founder and Chairman of Cresset, to discuss why he built a modern multi-family office after decades as an entrepreneur and investor. Eric explains the structural conflicts inside traditional wealth management, why most ultra-high-net-worth families lack true family office infrastructure, and how long-term thinking changes the way businesses, portfolios, and families compound over generations. We also explore governance, tax-aware investing, succession planning, and lessons from companies that have endured for centuries. Highlights: Why most wealth management firms fail entrepreneurs after liquidity events The hidden conflicts embedded inside traditional wirehouses Why family governance matters as much as investment performance The concept of “asset protection as compartments in a submarine” Why the next generation is often the greatest risk to family wealth How enduring companies survive across centuries and multiple crises Why building a business for the long term paradoxically accelerates growth The overlooked importance of stewardship in investing and leadership Guest Bio: Eric Becker is the Founder and Chairman of Cresset, a multi-family office and wealth management platform overseeing more than $250 billion in assets under management and advisement. Prior to founding Cresset, Eric built and invested in multiple businesses as an entrepreneur, beginning with a healthcare technology company he launched while attending the University of Chicago. He is also the author of The Long Game, a book exploring the lessons behind companies and families that have endured for generations, drawing on interviews with some of the world’s longest-lasting organizations and business leaders. 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 Becker: LinkedIn:https://www.linkedin.com/in/ebecker1/ 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 Billionaire Founders Were Disappointed by Private Banks (3:45) The Hidden Conflicts Inside Traditional Wealth Management (7:16) How Crescent Avoids the Incentive Problems Most RIAs Have (9:30) What Family Offices Actually Do Beyond Investing (15:05) Why “Wealth Preservation” Often Fails by the Third Generation (18:13) The Most Underrated Alpha in Investing: Structure and Taxes (22:25) The Asset Classes Smart Family Offices Are Quietly Buying (28:40) What 200-Year-Old Companies Understand That Startups Don’t (37:56) Why Building for the Long Term Creates Faster Growth (41:21) The Strange Paradox Behind Great Founders and Wealth
Summary
E379: Why Great Investment Firms Eventually Stop Performing
2w ago00:36:57Summary readyWhat if the biggest problem in asset management today isn’t investment performance—but misalignment between managers and the investors they serve? In this episode, I sit down with Luke Sarsfield, Chairman and CEO of Ridgepost Capital, to discuss how incentive structures shape long-term outcomes in private markets. Luke explains why Ridgepost leaves most carried interest with underlying managers, how alignment creates better LP relationships, and why middle market specialists can offer diversification that many large-cap private portfolios lack. We also explore long-term thinking, public versus private market pressures, culture, mentorship, and why compounding relationships may be the most valuable asset in investing. Highlights: Why alignment matters more than asset gathering in private markets The hidden correlation risk inside large private equity portfolios Why Ridgepost focuses on management fee ownership over carry How long-term incentives improve investment decision-making The tension between public market short-termism and private market compounding Why culture and mentorship compound harder than capital The importance of building teams without creating groupthink Why relationships become the ultimate competitive advantage over time Guest Bio: Luke Sarsfield is Chairman, Director, and Chief Executive Officer of Ridgepost Capital, an investment platform focused on partnering with specialized alternative asset managers. Prior to Ridgepost, he spent more than two decades at Goldman Sachs, where he served in several senior leadership roles including Global Co-Head of Goldman Sachs Asset Management and Chief Commercial Officer of Asset and Wealth Management. Across his career, Luke has focused on building enduring investment businesses, aligning incentives between managers and LPs, and helping scale world-class investment platforms with a long-term orientation. 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 Luke Sarsfield: LinkedIn:https://www.linkedin.com/in/luke-sarsfield/ 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 Asset Management Incentive Problem Ridgepost Is Trying to Fix (1:31) Why Carry Creates Better Investors Than Management Fees (3:03) The Hidden Correlation Risk Inside Private Equity Portfolios (4:45) Why Public Markets Assign Almost Zero Value to Carry (7:09) The Surprising Reason Great Managers Eventually Scale Anyway (9:38) Why Finance Quietly Rewards Short-Term Thinking (12:33) How a Public Company Can Still Think in Decades (17:57) What Asset Management Firms Are Actually Worth Today (23:33) The Common Pattern Across Every Great Asset Manager (31:53) The Most Important Career Decision Most People Get Wrong
Summary
E378: Why LPs Keep Selling Their Highest-Quality Funds
2w ago00:26:57Summary readyWhat if the biggest opportunity in private equity today isn’t buying companies—but buying liquidity from investors who are forced to sell great assets for reasons unrelated to performance? In this episode, I sit down with Ryan Levitt, Co-Head of LP Secondaries at ICG, to discuss why secondaries have evolved into one of the most attractive areas in private markets. Ryan explains how LP secondaries can outperform traditional buyouts with lower downside risk, why DPI pressures are reshaping institutional portfolios, and how rules-based allocators create structural inefficiencies. We also explore return dispersion, continuation vehicles, GP relationships, and why access and information matter more than sourcing in modern secondaries investing. Highlights: Why secondaries have historically outperformed most buyout funds The growing return dispersion inside private equity How DPI pressures are fueling record secondary market activity Why LPs often sell their best assets instead of their worst The hidden inefficiencies created by rules-based allocators Why access and information matter more than sourcing in secondaries How continuation vehicles are changing private markets liquidity Why culture and mentorship compound harder than compensation early in a career Guest Bio: Ryan Levitt is Co-Head of LP Secondaries at ICG, a global alternative asset manager with more than $126 billion in assets under management across private equity, credit, structured capital, and real assets. At ICG, Ryan focuses on originating and leading LP secondary transactions, co-investments, and primary fund commitments globally. Prior to joining ICG, he was a Partner and Portfolio Manager at Pomona Capital, where he helped build the firm’s private wealth interval fund platform, and earlier in his career he invested across direct equity and debt transactions at GE Capital. 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 Ryan Levitt: LinkedIn:https://www.linkedin.com/in/ryan-levitt/ 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 Secondaries Quietly Outperform Traditional Buyouts (2:22) The Hidden Problem Breaking Modern Buyout Returns (4:14) The DPI Crisis Forcing LPs Into the Secondary Market (7:45) Why LPs Sell Their Best Assets Instead of Their Worst (9:27) The Incentive Problem Quietly Driving Secondary Deal Flow (11:33) Where the Best Secondary Opportunities Exist Right Now (14:18) The Real Source of Alpha in Secondaries: Information and Access (18:37) Why There Still Isn’t Enough Capital in the Secondary Market (22:03) How ICG Scaled to $127B Without Burning GP Relationships (25:16) The Career Advice That Matters More Than Compensation
Summary
E377: Midas List VC: Why Most VCs Miss the Biggest Companies
2w ago00:43:30Summary readyWhat if the biggest venture returns are already gone by the time a category has a name? In this episode, I sit down with Niko Bonatsos, Founder and Managing Partner of Verdict, to discuss why the best venture opportunities emerge before consensus exists. Niko explains why “50% of the profits are made before a vertical even has a name,” how he identifies “freak” founders with extreme rates of learning, and why most VCs are structurally incentivized to follow momentum instead of creating conviction. We also explore why consumer and gaming are deeply undervalued today, how AI is changing company formation, and why relationship-building compounds harder than capital in venture investing. Highlights: Why the biggest venture profits are captured before categories are named The definition of a “freak” founder and why rate of learning matters most Why most VCs optimize for markups instead of outcomes How AI is compressing company-building timelines dramatically Why consumer, gaming, and crypto are deeply underappreciated today The hidden advantage of immigrant and neurodivergent founders Why “small thinking” competes with breakthrough ideas How relationship-building became General Catalyst’s long-term edge Guest Bio: Niko Bonatsos is the Founder and Managing Partner of Verdict, an early-stage venture firm focused on backing unconventional founders building entirely new categories. Prior to launching Verdict, he spent 15 years at General Catalyst, where he helped expand the firm from an emerging venture platform into one of the world’s leading investment franchises. Niko is known for investing early in overlooked markets, partnering with highly technical founders, and developing a reputation for identifying “freak” entrepreneurs with exceptional rates of learning and conviction. 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 Niko Bonatsos: LinkedIn:https://www.linkedin.com/in/bonatsos/ 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 50% of Venture Profits Are Made Before a Market Has a Name (2:27) Why Most VCs Are Just Following the Herd (3:30) The Brutal Reality of Scaling Early-Stage Venture (5:14) How He Finds Markets Before Anyone Else Believes (6:26) What Makes a Founder a “Freak” (8:43) Why Most Smart VCs Don’t Take Enough Risk (12:41) Why AI and American Dynamism Are Already Overhyped (16:51) The Contrarian Founder Archetype Most VCs Ignore (21:30) Why Nobody Wants to Fund Gaming Right Now (36:13) The Biggest Problem Inside Venture Capital Today
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