How I Invest with David Weisburd

By 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, Step... more

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The podcast currently has 323 episodes available.

How I Invest with David Weisburd episodes:

March 09, 2026E320: Why Institutional Capital Avoids the Best Returns
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 [email protected].
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 [email protected].
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
...more
46min
March 06, 2026E319: GP Stakes Investing: Liquidity, Alignment, and the Real Risk
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 [email protected].
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 [email protected].
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
...more
39min
March 05, 2026E318: The Biggest Mistake Investors Make When Building a Venture Portfolio
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 [email protected].
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 [email protected].
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
...more
24min
March 04, 2026E317: Why Most Real Estate Investors Optimize the Wrong Return Metric
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 Arcitell, 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 Architelle. 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 [email protected].
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 [email protected].
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
...more
16min
March 03, 2026E316: How Family Offices Design Portfolios for 30-Year Outcomes
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 [email protected].
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 [email protected].
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
...more
29min
March 02, 2026E315: Why Quantity Beats Quality (Why Van Gogh Proves It)
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 [email protected].
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 [email protected].
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
...more
1h 5min
February 27, 2026E314: How Endowments Actually Think About Risk
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 [email protected].
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 [email protected].
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
...more
27min
February 26, 2026E313: Why the Endowment Model Doesn’t Work for Taxable Investors
Why does applying institutional investing frameworks often fail for taxable investors and families?
David Weisburd speaks with Aneet Deshpande about adapting the endowment model to private clients, the rise of tax-aware private market investing, and why governance, pacing, and asset location matter more than product selection. Aneet explains how taxes, liquidity needs, and behavioral risks fundamentally change portfolio construction—and why clarity of objectives is the real edge.
Highlights:
Why institutional investing frameworks break down for taxable investors
The rise of the taxable private-market allocator
Asset allocation vs. asset location—and the cost of getting it wrong
How taxes can erode 30–40% of gross returns
Tax-efficient structures in infrastructure and private markets
Applying the endowment model to families: what’s usually missing
The three hardest problems: sizing, sourcing, and pacing
Denominator and numerator effects in volatile markets
Continuation vehicles, co-invests, and the evolution of fee structures
Why governance and investment policy matter more than tactics
Ranges vs. point targets in asset allocation
Managing capital calls without forcing bad sales
Why ad hoc investing quietly destroys portfolios
Key-man risk, manager “genius,” and process vs. discretion
Guest Bio:
Aneet Deshpande is a senior investment professional and allocator with deep experience advising institutions and private clients on portfolio construction, private markets, and governance. His work focuses on adapting institutional frameworks—such as the endowment model—to the realities of taxable investors, with an emphasis on tax efficiency, pacing, liquidity management, and long-term wealth preservation across generations.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
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 Aneet Deshpande:
LinkedIn: https://www.linkedin.com/in/aneetdeshpande/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
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
(1:00) Taxable Investors and Private Market Investments
(3:15) Endowment Model Challenges and Fee Trends in Alternatives
(9:17) Managing Liabilities and Understanding the Denominator Effect
(13:14) Governance and Best Practices in Wealth Preservation
(17:48) Addressing Governance Issues and the Perils of Random Investments
(21:37) Co-investment Trends and Algorithmic Approaches
(23:00) Navigating SPV Layers and Investment Fees
(24:05) Timeless Investment Principles and Intellectual Honesty
(27:33) Unique Traits of Successful Investors
(29:33) Analyzing Investment Manager Strengths and Strategic Planning
(32:21) Closing remarks
...more
33min
February 25, 2026E312: The Power Law of Reputation in Venture Capital
Can ethics, generosity, and long-term relationships really outperform aggression in venture capital?
David Weisburd speaks with David Hornik about why “nice guys finish first… eventually,” how power-law outcomes shape a venture career, and why reputation compounds more reliably than tactics. Hornik explains why backing unflinchingly ethical founders isn’t just moral—it’s a durable competitive advantage in an industry defined by uncertainty.
Highlights:
Why Hornik only backs founders who are “unflinchingly ethical”
Ethics vs. culture: where pushing hard crosses the line
Why venture capital is a business of disappointment—and patience
How one out of ten investments defines an entire career
The human cost of startup failure and why it never gets easier
Why power laws make venture outcomes feel irrational
Compounding reputation as the most valuable long-term asset
The “transitive property of reputation” in deal sourcing
Why founders should diligence investors as hard as VCs diligence founders
Giving vs. taking—and why pure givers still need boundaries
Media, conferences, and platforms as multiplicative ways to add value
EQ vs. IQ: why emotional intelligence matters more than raw intelligence
Why Hornik won’t invest without sharing a meal with founders
Guest Bio:
David Hornik is the Founder of Lobby Capital and a veteran venture capitalist with over 25 years of experience investing from seed to pre-IPO. He previously spent two decades at August Capital and was the first institutional investor in companies including Splunk. David is known for his emphasis on ethics, reputation, and long-term relationship-building as core drivers of venture success.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
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 Hornik
LinkedIn:https://www.linkedin.com/in/davidhornik/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
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
(1:18) Work-life balance in venture capital
(3:31) Investment disappointments and startup failures
(7:14) Power law outcomes and investment concentration
(10:37) Compounding reputation and career effects
(15:00) Long-term relationships and winning deals
(19:07) Diligence and investment strategy contrasts
(22:07) Role of luck and insights from Adam Grant
(28:12) Building a network and leveraging media
(30:27) Balancing IQ and EQ in startups
(34:28) Advice and validation of relationship-based strategies
(37:21) Understanding entrepreneurs and authenticity
(38:41) Closing remarks
...more
40min
February 24, 2026E311: How Continuation Vehicles Quietly Reshaped Private Equity
Why have continuation vehicles become one of the fastest-growing segments in private markets?
David Weisburd speaks with Benjamin Carper about what’s driving record CV volume, how these transactions solve structural mismatches in private equity fund lives, and why both LPs and GPs hold mixed views on the strategy. Ben explains how continuation vehicles create liquidity, extend ownership of high-quality assets, and reshape portfolio management across buyout and venture markets.
Highlights:
Why continuation vehicles reached over $100B in annual volume
How arbitrary fund life cycles created the need for CVs
The shift from selling winners to compounding them
Typical size ranges and asset profiles for continuation vehicles
Why LPs both value and struggle with CV decision-making
Continuation vehicles as a growing source of cash liquidity
Pricing mechanisms: auctions vs. sponsor-led recapitalizations
Best practices around LP rollover options and alignment
What makes a high-quality CV asset attractive to investors
How CVs function as “deal-level diligence” for LP–GP relationships
Differences between buyout and venture continuation vehicles
Guest Bio:
Benjamin Carper is a senior member of Jefferies’ secondaries team, where he helps lead a large platform focused on continuation vehicles and private market liquidity solutions. He advises sponsors and institutional investors on structuring, pricing, and executing single-asset continuation transactions across buyout, growth, and venture portfolios. Ben has worked on some of the earliest and largest continuation vehicles in the market and is closely involved in the evolution of CVs from a liquidity solution into a core portfolio management tool.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
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 Benjamin Carper:
LinkedIn: https://www.linkedin.com/in/benjamincarper/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
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 to continuation vehicles and market focus
(2:00) Increase in continuation vehicle volume and traditional hold period
(5:40) Continuation vehicles' impact on company management and LP perspectives
(9:09) Pricing and alignment in continuation vehicle deals
(12:16) Attractiveness and due diligence in continuation vehicle transactions
(16:57) Investor profiles and trends in continuation vehicles
(19:01) Continuation vehicles' role in venture capital and long-term relationships
(23:13) Notable deals and closing thoughts
...more
25min

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