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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:
    E323: How Billionaires Build Their Portfolios Mar 12, 2026
    Show notes

    What changes when wealth stops being about building and starts being about preserving? In this episode, I sit down with Jonathan Dane, CIO and Founder of Defiant Capital, to explore how family offices think about portfolio construction after a major liquidity event. Drawing on his experience at Goldman Sachs and Jefferies, Jonathan explains why independent advice matters and how families navigate the transition from wealth creation to long-term preservation.

    Highlights:

    • Why large banks struggle to deliver fully independent advice
    • The key psychological differences between Gen 1 and Gen 2 wealth
    • Estate planning moves entrepreneurs should make years before a liquidity event
    • Why gifting shares early can save millions in future estate taxes
    • How portfolio construction changes once wealth becomes generational
    • Why billion-dollar family offices are typically majority alternatives
    • The critical importance of liquidity management before committing to private funds
    • Why overcommitting to private equity can force families into bad financing decisions
    • The growing frustration with long-dated venture funds and low DPI
    • Why lower middle market private equity offers structural inefficiencies
    • The operational alpha opportunity in Rust Belt manufacturing businesses
    • How independent sponsors should demonstrate real skin in the game
    • The biggest mistake $50–$500M families make: over-diversifying into too many managers
    • Why AI should enhance diligence workflows but never replace human judgment

    Guest Bio:

    Jonathan Dane is the Chief Investment Officer of Defiant Capital, where he advises entrepreneurial families and multigenerational wealth on portfolio construction, liquidity management, estate integration, and alternative investments. He previously worked at Goldman Sachs and Jefferies, advising ultra-high-net-worth and institutional clients, and now focuses particularly on lower middle market private equity and operational value creation.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    We’d like to thank AlphaSense for sponsoring this episode!

    Sponsor:

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

    Stay Connected with David Weisburd:

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

    Stay Connected with Jonathan Dane:

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

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

    Disclaimer:

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

    (0:00) Why the Sell Side Gives Conflicted Advice (2:03) Why First-Generation Wealth Invests Differently (6:22) The Estate Planning Moves Entrepreneurs Miss (9:02) What Changes Once a Family Passes $50M (10:42) How Billion-Dollar Family Offices Build Portfolios (15:55) Building a Portfolio for a Newly Liquid $1B Family (19:20) Why Families Are Pushing Back on 15-Year Venture Funds (25:12) Why Lower Middle Market Private Equity Works (29:08) Independent Sponsors vs Traditional PE Funds (30:47) The #1 Portfolio Mistake Families Make

    E322: How $70 Billion Gets Allocated During Market Chaos Mar 11, 2026
    Show notes

    What if one of the most overlooked $700 billion pools of capital in the U.S. is quietly shaping private markets? In this episode, I sit down with Jennifer Mink, President of Investment Performance Services, an investment consulting firm overseeing roughly $70 billion in assets under advisement, to discuss how Taft-Hartley pension plans approach long-term investing. Jennifer shares how IPS designs portfolios that balance public and private markets, using disciplined asset allocation and diversification to improve overall portfolio efficiency and manage risk across market cycles.

    Highlights:

    • How adding alternatives can reduce overall portfolio volatility through low correlation
    • Why “double diversification” can dilute returns at the portfolio level
    • The importance of grounding investments in a clear thesis to avoid emotional selling
    • How IPS rebalanced aggressively during the 2020 market snapback
    • What gets easier and harder when advising $70 billion across nearly 200 union plans
    • Why emerging managers are typically tracked through three vintages before capital is deployed
    • Red flags in early funds including team turnover, fee changes, and strategy drift
    • The private equity distribution slowdown and pacing challenges facing LPs
    • Structural requirements managers must meet to access Taft-Hartley capital, including ERISA fiduciary status
    • The role of Responsible Contractor Policies in real asset mandates
    • Why sometimes the best investment decision is the one you avoid
    • How IPS tracks its own research process to ensure manager outperformance across cycles

    Guest Bio:

    Jennifer Mink is the President of Investment Performance Services (IPS), a 40-year-old investment consulting firm focused exclusively on the Taft-Hartley marketplace. IPS advises approximately $70 billion in assets and works with nearly 200 union plans nationwide. With more than two decades at the firm, Mink specializes in asset allocation, manager research, and private markets diligence, and leads a team that evaluates hundreds of managers annually while emphasizing disciplined structure, fiduciary responsibility, and consistency across full market cycles.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    We’d like to thank AlphaSense for sponsoring this episode!

    Sponsor:

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

    Stay Connected with David Weisburd:

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

    Stay Connected with Jennifer Mink:

    LinkedIn: https://www.linkedin.com/in/jennifer-mink-09057836b/

    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 Job of Deploying $70B in Institutional Capital (0:52) Why Alternatives Can Reduce Portfolio Volatility (3:03) The Biggest Behavioral Mistake Investors Make (4:31) How Institutions Invest During Market Crashes (6:08) What Gets Easier (and Harder) Managing $70B (8:05) How Consultants Diligence 300–400 Managers a Year (10:13) Why Institutions Wait Until Fund IV to Invest (13:34) The DPI Crisis Breaking the Endowment Model (15:05) The Hidden Rules for Raising Taft-Hartley Capital (22:28) The Best Investment Is Sometimes Saying No

    E321: Why Most LPs Have No Idea What’s in Their Portfolio Mar 10, 2026
    Show notes

    Why are private markets still managed in spreadsheets when hundreds of billions of dollars are at stake? In this episode, I sit down with Ryan Eisenman, Co-Founder and CEO of Arch, a platform supporting more than 550 clients and over $405 billion in alternative assets. Arch is building an operating system for private markets that helps investors manage the operational complexity of alternatives across private equity, venture, hedge funds, credit, and more, bringing modern infrastructure to a part of the financial system that has historically relied on manual processes and fragmented data.

    Highlights:

    • What breaks when an LP scales from 10 to 50 fund commitments
    • Why most private markets data is trapped in PDFs across 800+ portals
    • The hidden operational chaos inside family offices and RIAs
    • How poor liquidity visibility impacts re-up decisions
    • Why venture fundraising has fallen dramatically since 2022 peaks
    • The shift of capital from institutions to the wealth channel
    • Growth in independent sponsor and deal-by-deal allocations
    • Why private market data feeds often don’t match source documents
    • The rise of secondaries and tightening discount spreads
    • Why borrowing against private assets remains inefficient
    • How Arch uses AI to extract key terms from 100-page LPAs
    • Lessons Ryan learned building a venture-backed fintech company

    Guest Bio:

    Ryan Eisenman is the Co-Founder and CEO of Arch, a fintech platform that automates data aggregation, reporting, and analytics for alternative investments. Arch serves global banks, RIAs, family offices, and institutional allocators, helping them manage complex private market portfolios more efficiently.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    We’d like to thank AlphaSense for sponsoring this episode!

    Sponsor:

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

    Stay Connected with David Weisburd:

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

    Stay Connected with Ryan Eisenman:

    LinkedIn: https://www.linkedin.com/in/ryan-eisenman-21811246/

    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) $405B in Private Market Assets — But LPs Still Use Spreadsheets (1:19) The Hidden Chaos of Tracking Private Investments (2:05) Why LPs Don’t Understand Their Own Liquidity (3:54) What Breaks When LPs Go From 10 to 50 Funds (5:17) The Manual Systems Behind Billion-Dollar Portfolios (7:00) Why Private Markets Data Is Completely Fragmented (9:11) The Shift From Institutions to Wealth Channel Capital (12:24) The DPI Crisis Reshaping Venture Capital (13:38) Why You Can’t Borrow Against Private Assets (15:40) How AI Is Finally Fixing Private Markets Data

    E320: Why Institutional Capital Avoids the Best Returns Mar 09, 2026
    Show notes

    What if the best private equity opportunities are the ones no one else is set up to pursue? In this episode, I sit down with Jeff Collins, Founder and Managing Partner of Cloverlay, to explore how he built a $2 billion firm by going where capital isn’t. After 14 years at Morgan Stanley Investment Management, Jeff spun out to focus on what he calls “uncorrelated private assets” - niche, often overlooked segments where return dispersion is wide and operator selection matters more than financial engineering.

    Highlights:

    • Why “go where the money isn’t” only works if you build the right organization around it
    • How Cloverlay built a sourcing flywheel through references and long-term reciprocity
    • The importance of holding structured “kill calls” to preserve relationships
    • Why broad dispersion of returns signals opportunity in overlooked markets
    • How to evaluate niche segments like special mission aircraft, wireless spectrum, and IP
    • The strategy behind assembling “portfolio premium” assets in industrial outdoor storage
    • Why uncorrelated private assets can act as ballast in institutional portfolios
    • How pensions think about completion portfolios and non-beta exposure
    • The tradeoff between being an A+ specialist versus a well-rounded investor
    • Why Jeff believes ego should be tied to performance, not AUM growth
    • The cultural decision to remain focused instead of scaling into adjacent strategies

    Guest Bio:

    Jeff Collins is the Founder and Managing Partner of Cloverlay, a Philadelphia-based private investment firm managing approximately $2 billion in assets focused on uncorrelated private markets.

    Before founding Cloverlay in 2015, Jeff spent 14 years at Morgan Stanley Investment Management, where he led investments across private market strategies and developed a focus on segments with high return dispersion and limited competition.

    At Cloverlay, Jeff and his team specialize in niche asset categories ranging from intellectual property and aviation to industrial outdoor storage and other esoteric markets. The firm partners with highly specialized operators and seeks to generate performance through asset selection, structure, and disciplined portfolio construction rather than market beta or leverage.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    We’d like to thank AlphaSense for sponsoring this episode!

    Sponsor:

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

    Stay Connected with David Weisburd:

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

    Stay Connected with Jeff Collins:

    LinkedIn: https://www.linkedin.com/in/jeff-collins-76b7b54/

    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 Strategy: Go Where the Money Isn’t (1:44) Why the Best Opportunities Take 291 Days to Close (3:20) Building Deal Flow Without Bankers or Auctions (7:59) Why Relationships Matter More Than Transactions (11:04) The Power of Proactive Deal Sourcing (14:48) How Small Markets Create Big Returns (19:17) The Role of Uncorrelated Assets in Portfolios (26:39) Why Investors Love Wide Dispersion of Returns (33:38) Turning Gravel Parking Lots Into Institutional Assets (47:27) Why Performance Matters More Than AUM

    E319: GP Stakes Investing: Liquidity, Alignment, and the Real Risk Mar 06, 2026
    Show notes

    Why would an LP invest in the GP instead of the fund… and what problem is GP stakes really solving? In this episode, I sit down with Todd Owens, Managing Partner of Cantilever Group, to unpack the world of GP stakes. Todd explains what investors are actually buying when they take a minority stake in an alternative asset manager, why liquidity risk is the central challenge, and how structural innovation could reshape the asset class.

    Highlights:

    • What you are really underwriting when you invest in a GP instead of a fund
    • The hidden liquidity risk most LPs underestimate in GP stakes
    • Why unpredictable exits are the defining challenge of minority GP investing
    • How public listings could reshape liquidity for GP stakes funds
    • Why lower middle market GP deals may offer structural advantages
    • The three primary reasons GPs sell minority stakes and which one Todd likes most
    • When growth capital meaningfully accelerates a manager’s trajectory
    • Red flags when principals are taking money off the table
    • How to distinguish between a durable firm and a single-founder platform
    • Why venture capital can be “too volatile” for GP stakes investors
    • The pricing discipline required to walk away from good businesses
    • How strategic value creation works when you are a passive minority partner

    Guest Bio:

    Todd Owens is the Managing Partner of Cantilever Group, an investment firm that focuses on minority GP stakes in lower middle market alternative asset managers. The firm targets investments between $15 million and $75 million, partnering with managers seeking growth capital, capital restructuring, or solutions for generational transitions. Todd previously spent decades advising and working with asset management businesses, including serving as a Partner at Goldman Sachs, and at Cantilever Group he focuses on building a permanent capital model that aligns with GPs while addressing liquidity considerations for LPs.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    We’d like to thank AlphaSense for sponsoring this episode!

    Sponsor:

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

    Stay Connected with David Weisburd:

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

    Stay Connected with Todd Owens:

    LinkedIn: https://www.linkedin.com/in/todd-owens-401976160/

    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 decision.

    (0:00) Why GP Stakes Became a New Asset Class (0:36) What Investors Actually Buy in a GP Stake (1:22) Fund Returns vs. Owning the Management Company (2:09) The Biggest Risk: Unpredictable Liquidity (3:18) How GP Stakes Investors Create Liquidity (5:44) The Permanent Capital Model for GP Stakes (10:30) The 3 Reasons GPs Sell Stakes in Their Firm (11:56) How GP Stakes Capital Fuels Firm Growth (19:07) When GPs Take Money Off the Table (31:03) The Strategic Advantage of Investing at the GP Level

    E318: The Biggest Mistake Investors Make When Building a Venture Portfolio Mar 05, 2026
    Show notes

    What separates elite venture LPs from everyone else… and why do most family offices underestimate the governance required to win? In this episode, I sit down with Michael P. Larsen, a longtime Partner at Cambridge Associates, to unpack nearly two decades of building venture and private equity portfolios for leading institutions and family offices. Michael shares why longevity may be the ultimate competitive advantage in asset management, how governance quietly determines venture outcomes, and why portfolio size can matter just as much as manager selection. We dive into power laws, spiky returns, growth equity’s overlooked role, co-invest best practices, and how benchmarking can help LPs stay disciplined during optically challenging cycles.

    Highlights:

    • Why longevity in venture investing creates perspective most LPs never develop
    • The hidden edge elite LPs have in portfolio sizing, not just manager selection
    • Why governance may be the most underestimated driver of venture outcomes
    • How to structure a venture allocation after a liquidity event
    • The real reason venture portfolios feel “spiky” and why that is a feature, not a flaw
    • Why waiting for obvious top managers often leads to second-tier access
    • How fund cadence compression can quietly distort portfolio construction
    • The importance of underwriting firms, not just individual funds
    • Why benchmarking venture is especially challenging in Mag-7 dominated markets
    • Growth equity as the “third bowl of porridge” between venture and buyout
    • Co-invest adverse selection risks and how scale improves access
    • Systematic vs opportunistic co-invest strategies and when each makes sense

    Guest Bio:

    Michael P. Larsen is a Partner at Cambridge Associates, where he has spent nearly two decades advising institutional investors and family offices on venture capital, private equity, and growth equity portfolio construction.

    Over the course of his career, he has participated in thousands of GP meetings and helped design durable private market programs focused on governance, manager selection, and long-term discipline. His work emphasizes strategic allocation, benchmarking rigor, and building venture portfolios designed to withstand multi-decade market cycles.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    We’d like to thank AlphaSense for sponsoring this episode!

    Sponsor:

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

    Stay Connected with David Weisburd:

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

    Stay Connected with Michael Larsen:

    Michael Larsen: https://www.linkedin.com/in/michaelplarsen/

    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 Longevity Advantage in Venture Investing (1:48) Why Venture Portfolios Behave Completely Differently (2:12) The Hidden Variable: Allocation Size Matters (4:30) Governance: The Least Sexy Alpha (6:15) Step One: Define Your Illiquidity Budget (8:33) Why Elite LPs Accept “Spiky” Returns (10:36) How Many Venture Funds You Actually Need (12:19) The Biggest Portfolio Construction Mistake (17:57) The Long-Term Game LPs Are Playing (20:54) The Real Risk in Venture Co-Investing

    E317: Why Most Real Estate Investors Optimize the Wrong Return Metric Mar 04, 2026
    Show notes

    What if the biggest untapped source of alpha isn’t better investments… but better tax structure? In this episode, I sit down with Andrew Berman, Co-Founder and Managing Partner of Arqitel, to explore the overlooked power of tax-aware private real estate investing. After starting his career at AQR Capital Management and working closely with one of its co-founders inside a family office, Andrew saw firsthand how tax-aware strategies transformed public market investing. He realized private markets had yet to fully adopt the same discipline. We break down structural alpha, why many private real estate managers are incentivized to sell too soon, and how taxable investors can materially improve long-term wealth creation by aligning investment strategy with tax structure. In increasingly efficient markets, tax may be one of the few durable advantages left.

    Highlights:

    • Why most private real estate investors underestimate how much taxes impact long-term returns
    • How structural alpha can potentially exceed the dispersion between median and top quartile managers
    • Why five-year hold periods may quietly erode after-tax wealth
    • The mechanics of depreciation recapture and capital gains drag
    • How manager incentives often conflict with after-tax optimization
    • Why long-duration holds can enhance compounding for taxable investors
    • When 1031 exchanges make sense and when they may introduce hidden costs
    • Why taxable investors may be structurally under-allocated to private real estate
    • How family offices think differently about liquidity, control, and tax efficiency
    • Why after-tax return may become the defining metric for modern portfolio construction

    Guest Bio:

    Andrew Berman is the Co-Founder and Managing Partner of Arqitel. He previously began his career at AQR Capital Management and later worked within the family office of David Kabiller. His work focuses on maximizing after-tax returns for ultra-high-net-worth investors through tax-aware private real estate strategies.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    We’d like to thank AlphaSense for sponsoring this episode!

    Sponsor:

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

    Stay Connected with David Weisburd:

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

    Stay Connected with Andrew Berman:

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

    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 Real Estate Is the Most Tax-Advantaged Asset Class (1:22) The Hidden Returns Most Investors Leave on the Table (2:21) How Taxes Can Cut Your Real Estate Returns in Half (4:29) The Power of Depreciation and K-1 Pass-Throughs (5:28) Why Most Real Estate Funds Trigger Unnecessary Taxes (6:49) A Simple Example of 35% Tax Drag (9:08) The Truth About 1031 Exchanges (10:46) The Two Types of Family Office Investors (13:24) Why Tax Alpha Is the Next Big Investing Edge (14:47) Tax Strategy vs Picking Top Quartile Managers

    E316: How Family Offices Design Portfolios for 30-Year Outcomes Mar 03, 2026
    Show notes

    What if the easiest alpha in public markets isn’t stock picking… but taxes? In this episode, I sit down with Zach Wainwright, Founder of Twin Oak ETF Company, to break down structural alpha, ETF tax efficiency, and how high-net-worth investors can compound capital more intelligently. Zach shares lessons from his time at Wellington, TIFF, and inside a single-family office — and why long time horizons, incentive alignment, and tax awareness may be more powerful than traditional stock-picking alpha. We also dive into tail-risk hedging inside an ETF wrapper and how families can design portfolios to survive extreme drawdowns without sacrificing long-term compounding.

    Highlights:

    • Why “long-term” means something different for asset owners vs. traders
    • Lessons from Wellington, TIFF, and investing in emerging managers
    • Why fund one through fund three often generate the most alpha
    • Incentive alignment and GP capital commitments
    • Structural edges inside single-family offices
    • The three levers of value creation: security selection, asset allocation, structural alpha
    • Tax drag in mutual funds vs. ETFs
    • How ETFs preserve tax alpha through in-kind redemptions
    • Tail-risk hedging inside an ETF vs. private hedge funds
    • Avoiding the 10 worst days — and capturing the 10 best
    • Designing portfolios to reduce maximum drawdown
    • Why tax deferral may be the most sustainable form of alpha

    Guest Bio:

    Zach Wainwright founded Twin Oak ETF Company with a singular focus: delivering innovative, institutional-quality, tax-efficient solutions to high-net-worth clients. Throughout his career at firms such as Wellington Management and TIFF, and later within a single-family office, Zach observed that taxable investors were often underserved — losing significant performance to unnecessary tax drag despite strong investment selection.

    At Twin Oak, Zach focuses on what he calls “structural alpha” — leveraging time horizon, tax efficiency, and thoughtful implementation to unlock portfolio potential. His approach blends institutional rigor with family-office pragmatism, creating ETF-based solutions that aim to preserve compounding, reduce drawdowns, and optimize after-tax outcomes for long-term investors.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    We’d like to thank AlphaSense for sponsoring this episode!

    Sponsor:

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

    Stay Connected with David Weisburd:

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

    Stay Connected with Zach Wainwright:

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

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

    Disclaimer:

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

    (0:00) Introduction (0:13) Importance of long time horizon and differences in investing perspectives (1:16) Lessons from Wellington and transition to TIFF and early stage fund managers (2:25) Risk, incentives, and alpha generation with early fund managers (4:08) Risk-return tradeoffs and identifying traits in emerging managers (5:57) Transition to single family office (7:40) Structural advantages and unique investment strategies of family offices (10:25) Founding Twin Oak, investment philosophy, and tax strategies (13:48) Tail hedging strategies and costs/benefits of hedging (18:18) Optimizing portfolios: Long-only versus hedged performance (20:36) Client-driven innovation and optimal long-term public portfolio strategies (22:31) The evolving ETF ecosystem and the rise of taxable investors (24:51) Partnering with offices, hedge fund managers, and the importance of tax-aware investing (26:44) Advice for a younger self and the value of diverse experiences (28:14) Closing remarks

    E315: Why Quantity Beats Quality (Why Van Gogh Proves It) Mar 02, 2026
    Show notes

    What if success isn’t about talent… but about multiplying your effort by 10? In this episode, I sit down with Grant Cardone, CEO of Cardone Capital, to break down the mindset behind the 10X Rule, omnipresence in marketing, raising billions from retail investors, and why quantity always precedes quality. Grant shares how he built a $5B real estate portfolio, scaled a media machine that sends hundreds of millions of emails per year, and combined Bitcoin with multifamily real estate to create a new hybrid investment vehicle. We also unpack why most people underestimate effort, why repetition builds self-esteem, and why illiquidity may be the real edge in investing.

    Highlights:

    • Why people systematically underestimate how hard success actually is
    • The real meaning behind the 10X Rule
    • Quantity vs. quality — why reps create excellence
    • How omnipresence builds brand power
    • The psychology of follow-up and rejection in sales
    • Raising over $2B directly from retail investors
    • Why retail capital can be more powerful than institutional money
    • The real estate + Bitcoin hybrid strategy
    • Illiquidity as an investment advantage
    • Tokenization vs. going public
    • Lessons from addiction, ego, and resilience
    • Why exceptional performance requires extreme repetition

    Guest Bio:

    Grant Cardone is the CEO of Cardone Capital, a private real estate investment firm managing over $5 billion in assets. He is the author of eight business books, creator of thirteen best-selling business programs, and CEO of seven privately held companies generating approximately $750 million in annual revenue. Over the past three decades, Grant has advised companies on sales expansion, profitability improvement, and operational scaling through disruptive marketing and training systems.

    Recognized by Forbes as one of the top social media business influencers in the world, Grant built a global brand by embracing omnipresence, repetition, and relentless follow-up. Through Cardone Capital, he has raised billions from retail investors and continues to innovate with new financial structures, including real estate and Bitcoin hybrid vehicles and tokenized asset strategies.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    We’d like to thank AlphaSense for sponsoring this episode!

    Sponsor:

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

    Stay Connected with David Weisburd:

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

    Stay Connected with Grant Cardone:

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

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

    Disclaimer:

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

    (0:00) Introduction (1:30) The 10x rule, fear of being ignored, and underestimating effort (3:14) Schooling system, entitlement, and work ethic (5:52) Teaching practical skills and dealing with rejection (7:24) Analyzing top performers' strengths and weaknesses (9:14) Assets, liabilities, and misconceptions in finance (10:43) Marketing strategies and the rule of seven (16:15) Mastering persistence in sales and follow-up tactics (22:06) Media democratization and achieving excellence through repetition (26:11) Quantity vs. quality debate and embracing failure (33:57) Victim mentality and overcoming it (36:21) Raising capital and innovations in real estate funding (39:46) Tokenizing real estate and integrating Bitcoin investments (43:54) Illiquidity as a virtue and Bitcoin risks in real estate (48:26) Behavioral investing and creating anti-fragile portfolios (51:06) Real estate growth and scaling challenges (52:25) Property taxes and investment impacts (55:04) Migration patterns and economic effects on cities (57:42) Wealth accumulation strategies (1:00:25) Advice to younger self and life balance insights (1:02:54) Perspectives on public offerings and tokenizing assets (1:04:08) Expanding investor base and future aspirations (1:04:12) Closing remarks

    E314: How Endowments Actually Think About Risk Feb 27, 2026
    Show notes

    If private equity generates alpha, why are investors still paying for beta? In this episode, I sit down with Roger Vincent, Founder and CIO of Summation Capital, to break down portfolio construction, co-investing, and fee alignment in private equity. After more than a decade leading Cornell University’s multi-billion-dollar private equity portfolio, Roger shares why diversification in PE actually increases expected return, how elite endowments use co-investments to systematically reduce fee drag, and why most allocators are misaligned with the capital they steward. We also unpack Summation’s industry-first structure—charging carry only on alpha over a public benchmark and offsetting fees through a no-fee, no-carry co-investment program.

    Highlights:

    • Why portfolio construction is the most underrated driver of returns
    • The false tradeoff between diversification and performance
    • Venture capital’s cyclicality vs. buyout stability
    • Why private equity beta is still expensive
    • Benchmarking PE against public markets for compensation alignment
    • Co-investments as a 600 bps fee arbitrage
    • The dangers of under-diversified direct investing
    • Behavioral finance and systematic co-investing
    • “Gather a bunch of hawks” — diversified specialization
    • Why double diversification destroys value
    • Paying carry only on alpha over a public benchmark

    Guest Bio:

    Roger Vincent is the Founder and CEO of Summation Capital. Previously, he spent 12 years at the Cornell University endowment, where he managed private equity investments through multiple market cycles and helped construct a highly diversified institutional portfolio.

    Earlier in his career, Roger was a GP, giving him direct experience in underwriting, syndicating, and executing investments. His work focuses on alignment, portfolio construction, and bringing endowment-style investing to a broader set of asset owners.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    We’d like to thank AlphaSense for sponsoring this episode!

    Sponsor:

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

    Stay Connected with David Weisburd:

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

    Stay Connected with Roger Vincent:

    LinkedIn: https://www.linkedin.com/in/roger-vincent-1a6423/

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

    Disclaimer:

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

    (0:00) Introduction (0:42) Importance of portfolio construction and role of specific assets (2:26) Public vs. private market exposure (5:10) Influence of Professor Steve Kaplan and allocator incentives (7:38) Benchmarking and co-investment strategies (12:39) Diversification strategies for endowments (18:00) Overview of Summation Capital and misconceptions about diversification (24:14) Summation Capital's unique approach to aligning incentives (25:49) Closing remarks

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