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    Business

    How I Invest with David Weisburd

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

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    Copyright: © Copyright 2025 How I Invest with David Weisburd

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    Latest Episodes:
    E383:Why the Next Fortune 500 Companies Will Be Built on AI Jun 04, 2026
    Show notes

    What 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

    E382: Why Venture Capital Has a $3 Trillion Liquidity Problem Jun 03, 2026
    Show notes

    What 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

    E381: A16Z Partner: The Tax Strategy Hidden Inside Real Estate Jun 02, 2026
    Show notes

    What 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

    E380: How Billionaire Family Offices Actually Invest Jun 01, 2026
    Show notes

    What 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

    E379: Why Great Investment Firms Eventually Stop Performing May 29, 2026
    Show notes

    What 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

    E378: Why LPs Keep Selling Their Highest-Quality Funds May 28, 2026
    Show notes

    What 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

    E377: Midas List VC: Why Most VCs Miss the Biggest Companies May 27, 2026
    Show notes

    What 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

    E376: The $3 Trillion Liquidity Problem in Venture Capital May 26, 2026
    Show notes

    What if the biggest opportunity in venture today isn’t funding new companies—but solving the liquidity crisis created by companies staying private for 20 years? In this episode, I sit down with Jared Carmel, Founder and Managing Partner of Manhattan Venture Partners, to discuss how venture secondaries evolved from a gray market into critical infrastructure for private capital markets. Jared explains why nearly $3 trillion is now trapped in aging venture funds, how DPI became the defining metric for LPs, and why secondary liquidity is now essential for founders, employees, and venture firms alike. We also explore continuation vehicles, cap table management, institutionalization of the secondary market, and why trust compounds faster than capital in private investing.

    Highlights:

    • Why companies staying private for 20+ years changed venture forever
    • The $3T liquidity problem sitting inside venture capital
    • Why DPI matters more than IRR for LPs today
    • How secondaries became institutionalized after years as a “gray market”
    • Why trust compounds faster than capital in private markets
    • The hidden risks inside retail SPVs and secondary hype cycles
    • How continuation vehicles are reshaping venture fund liquidity
    • Why “land and expand” became MVP’s core investment strategy

    Guest Bio:

    Jared Carmel is the Founder and Managing Partner of Manhattan Venture Partners, a leading venture secondary investment firm managing billions across primary and secondary private market investments. He has spent more than a decade helping institutionalize venture secondaries, building liquidity solutions for founders, employees, and investors in many of the world’s most valuable private technology companies. Through MVP’s “Land and Expand” strategy, Jared has invested across category-defining businesses including SpaceX, Anthropic, Databricks, xAI, and Coinbase, while helping shape the modern private liquidity ecosystem.

    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 Jared Carmel:

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

    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 $3 Trillion Problem Locked Inside Venture Capital (1:18) Why Great Companies Stay Private for 20 Years (2:41) Why DPI Suddenly Matters More Than IRR (5:16) How the Secondary Market Became Institutional (7:48) The Hidden Risk in Retail Secondary SPVs (12:29) How MVP Competes in One of the Hardest Markets (14:45) Why Continuation Vehicles Could Fix Venture’s DPI Problem (19:04) The Trust That Built a $3B Secondary Platform (26:47) What MVP Could Become in 10 Years (28:12) The Advice That Would Have Changed Everything

    E375: Why Tax Alpha Could Matter More Than Investment Returns May 22, 2026
    Show notes

    What if the biggest source of alpha for taxable investors isn’t stock picking—but minimizing friction inside the portfolio itself? In this episode, I sit down with Brent Sullivan, independent tax analyst and author of one of the leading research platforms on tax-aware investing, to discuss why tax alpha has become one of the fastest-growing themes in wealth management. Brent explains how long-short tax-loss harvesting strategies evolved from niche institutional products into mainstream planning tools, why tracking error is often misunderstood, and how sophisticated investors think about balancing risk, leverage, and after-tax returns. We also explore trader funds, operational risk, and why tax management may matter more than active management for many investors.

    Highlights:

    • Why tax alpha can matter more than active management returns
    • How long-short portfolios create recurring tax-loss harvesting opportunities
    • The hidden risks behind aggressive tax-loss harvesting strategies
    • Why tracking error is often a feature, not a flaw
    • The operational complexity most investors underestimate
    • How trader funds generate ordinary losses
    • Why the best tax strategies are tied to assets investors already want to own
    • The difference between tax planning and “the tax tail wagging the dog”

    Guest Bio:

    Brent Sullivan is an independent tax analyst, software developer, and writer focused on tax-aware investing and portfolio construction. He publishes widely followed research on tax alpha, long-short investing, and advanced wealth management strategies through his platform Tax Alpha Insider. Brent specializes in analyzing the mechanics, risks, and implementation details behind sophisticated tax planning strategies used by advisors, family offices, and institutional 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 Brent Sullivan:

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

    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 Tax Alpha Became the “Boring” Edge Investors Miss (4:03) The Strategy Making Tax Loss Harvesting Explode (7:03) Where These Massive Tax Losses Actually Come From (12:28) The Biggest Players in Tax Loss Harvesting 3.0 (14:36) The Hard Part No One Talks About: Unwinding the Trade (19:39) Why Some Families Never Unwind These Strategies (23:12) The Hedge Fund Tax Strategy Quietly Gaining Momentum (29:15) How Tax Alpha Strategies Can Fail (36:54) Why Tracking Error Isn’t Always a Bad Thing (43:11) Why He Wishes He Went Independent Much Earlier

    E374: Why the Best Investors Prepare for Crashes Before They Happen May 21, 2026
    Show notes

    What if the key to outperforming isn’t taking more risk—but building a portfolio strong enough to survive volatility without breaking? In this episode, I sit down with Doug Hanly, CIO of the Louisiana State Police Retirement System, to discuss why liquidity, simplicity, and process are the foundations of durable investing. Doug explains why he views short-term government credit as the “supply depots” of a portfolio, how preparation during calm periods creates opportunities during crises, and why avoiding mistakes matters more than chasing complexity. We also explore governance, manager selection, portfolio construction, and how small incremental improvements compound into long-term outperformance.

    Disclaimer: The thoughts and opinions expressed in this material and oral presentation are the author's and not necessarily those of the Louisiana State Police Retirement System, the Board of Trustees of the Louisiana State Police Retirement System, or the State of Louisiana. The statements and conclusions in this material and oral presentation are not binding on the State of Louisiana and its agencies, officers, and employees and do not alter the law of the State of Louisiana or policies of the Louisiana State Police Retirement System. In the event of a conflict between the material contained in this document and the applicable law, regulation, or policy, then the law, regulation, or policy is controlling.

    Highlights:

    • Why liquidity creates optionality during market dislocations
    • The hidden risk of fragile portfolios during crises
    • Why simplicity often outperforms complexity in investing
    • How governance shapes long-term investment outcomes
    • The importance of “killing weak ideas early”
    • Why smaller specialist managers often outperform larger funds
    • How incremental improvements compound into durable alpha
    • The role of preparation and psychology during drawdowns

    Guest Bio:

    Doug Hanly, CFA, CAIA, is the Chief Investment Officer of the Louisiana State Police Retirement System, where he oversees total portfolio strategy across public and private markets for the $1.5 billion pension fund. He previously held investment roles at Atala Financial, Windrose Advisors, Mass General Brigham, and the Washington University Investment Management Company. Doug also teaches hedge funds at LSU, founded the Next CIO Institute, and is known for his disciplined approach to governance, risk management, and institutional portfolio construction.

    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 Doug Hanly:

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

    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 Short-Term Government Bonds Are His Favorite Asset Class (3:41) The Contrarian Advantage of Holding Cash During Crashes (7:17) Why Asset Management Is Basically Exposure Therapy (10:01) The Slow-Motion Strategy That Protects LPs From Disaster (13:06) Why Smaller Funds Often Generate More Alpha (17:43) The Hidden Power of Simplicity in Investing (20:14) Why Quantity Quietly Creates Better Investors (22:25) The Surprising Benefits of a “Boring” Portfolio (25:10) The Consultant Strategy Most LPs Completely Miss (26:56) The One Simple Question That Can 10X Results

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