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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:
    E23: How Israel’s Largest Hospital Delivers Care to Palestinians through “Peace Through Health" Nov 28, 2023
    Show notes

    Brian Abrahams, CEO of American Friends of Sheba Medical Center, sits down with David Weisburd to discuss its “Peace through Health Initiative” and how the hospital has been helping Israeli and Palestinian citizens during the current conflict. (0:00) Episode Preview (0:30) Brian Abrahams’ Background (0:51) Rice Powell’s Background (2:05) Sheba Medical Center’s History (4:43) The Peace through Health Initiative (6:14) How to Combat the War of Propoganda (7:22) How Sheba responded to the attacks of 10/7 (9:30) Sheba’s partnership with Nuvo to help pregnant mothers (11:11) Firsthand impact of 10/7 (17:48) www.standwithsheba.com (18:42) How Sheba is helping heal national trauma (21:32) How Sheba has helped patients


    E22: Alex Edelson of Slipstream on The 4 Sources of Alpha for Emerging Managers Nov 21, 2023
    Show notes

    Alex Edelson of Slipstream Investors, sits down with David Weisburd and Erik Torenberg to discuss the four sources of alpha for emerging managers (Sourcing, Picking, Winning, and Value-Add). We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:20) Episode Preview (1:46) Slipstream’s fund strategy (2:57) What to look for when diligencing a GP (6:32) The typical Slipstream diligence process (7:34) What Alex wants to hear on a GP reference call (10:05) Why does fund performance decline in later vintages? (12:31) Episode Sponsor: Bidav Insurance Group (16:00) How should family offices approach venture? (18:15) Why concentration drives performance (19:23) Alex’s value add to GPs (21:47) The folly of optimizing on special economics (23:30) Generalists vs. Specialists (26:32) Ranking of Sourcing, Picking, Winning, and Value Add by importance (28:07) How to be a good sourcer (30:59) How to be a good picker (32:25) How to win deals (33:32) Fundraising and investing are different skills (39:51) Lessons from working at QED (47:51) The difference between a good LP and a great LP (49:40) How to optimize portfolio construction (57:00) Are GPs penalized for not doing pro-rata? (58:04) “I want to help venture firms, whether or not I invest.”


    E21: Jake Paul and Joey Levy of Betr on How to Build a $100 Billion Company Nov 16, 2023
    Show notes

    Jake Paul and Joey Levy, co-founder of Betr, sit down with David Weisburd to discuss the sports betting industry and how to build a $100 billion company. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (1:29) Mike Brown’s, Head Coach of the Kings, thoughts on Jake Paul (1:59) The importance of self belief (3:12) What drives Jake Paul? (4:50) Living life like it’s monopoly (7:06) Jake’s views on psychedelics (8:38) “Good news travels fast, bad news travels faster” (10:28) Why Joey chose to partner with Jake (11:05) Joey’s experience with founding Simplebet (11:29) Aligning ambitions and incentives (13:06) The benefits of a 50/50 partnership (13:50) Episode Sponsor: Bidav Insurance Group (14:57) The interpersonal dynamics of being co-founders (16:06) The Betr tattoos (18:02) The market gap that Betr is filling (19:03) Creating a more intuitive sports betting platform (19:55) Capturing the casual sports fan (21:56) Why high marketing costs hurt current incumbents and how Betr capitalizes on the inefficiencies (25:54) “Betr is first and foremost a gaming business” (26:47) Digging in to Betr’s financials (29:33) Betr’s path to being a $100 billion company (31:41) What drives Joey Levy?


    E20: James Heath, dara5 on How Family Offices Access Top Venture Funds Nov 14, 2023
    Show notes

    James Heath, Investment Principal at dara5, sits down with David Weisburd to discuss early stage venture. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (1:36) How PwC evaluates venture companies (3:25) Non-consensus learning about VC (4:30) Look for entrepreneurs that are trying to solve a critical problem (6:25) What is dara5? (8:36) How can information provide alpha? (11:01) The importance of data when co-investing (12:32) Warm versus cold intro co-investments and how to implement a double gated process (15:53) Episode Sponsor: Bidav Insurance Group (17:22) Smaller funds and ownership levels (19:06) Build long term relationships with GPs: education and casual conversations (24:13) The changing power structures in fundraising (25:34) The competing dynamics of a challenging market and investor friendly terms (28:16) How family offices should invest in venture (31:19) How to unlock the mean venture IRR of 50% (34:29) Which is a better investment: top decile backed company or an emerging manager? (35:45) Reaching Series B increases likelihood of unicorn status to 24% (37:27) AGM best practices (39:45) The importance of sharing knowledge (41:40) Why only early stage venture is non-zero sum (45:46) What’s actually going to happen in the VC reset (50:21) The emergence of European VC (51:52) Don’t be scared of emerging managers


    E19: Raja Doddala, Head of VC at Churchill ($47 Billion AUM) on How LP’s Should Diligence GP’s Nov 09, 2023
    Show notes

    Raja Doddala, Head of VC at Churchill Asset Management, sits down with David Weisburd to discuss how Churchill diligences managers, and the importance of integrity in a GP. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (1:53) Churchill background (3:08) Pulling the curtain back on the IC process (5:24) The quantitative and qualitative nature of Venture (7:00) The importance of integrity in a manager (10:33) The correlation between price sensitivity and DPI (13:22) Right companies. Right time. (14:17) Episode Sponsor: Bidav Insurance Group (15:15) How Venture fits in a portfolio (17:57) Smaller fund historically have better returns (18:53) Raja’s ideal fund (19:57) Khosla’s bet on OpenAI (20:55) Why Vinod Khosla is a great VC (21:52) Why Keith Rabois is a great VC (22:39) Operator vs Non-Operator (23:08) Specialist vs Generalist (26:02) Opportunity funds and staples (26:56) Doubling down on outliers through co-investments (29:23) How Churchill supports their GPs (37:22) “We’re open for business”


    E18: Avlok Kohli, CEO of AngelList on How He Turned AngelList into a $4 Billion Dollar Company Nov 07, 2023
    Show notes

    Avlok Kohli, CEO of AngelList sits down with David Weisburd and Erik Torenberg to discuss how he grew AngelList into a $4B dollar company. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (0:59) Why Founders need to be resilient (2:49) Why it’s rational to double down on yourself (4:57) Founder vs Operator mentality (11:07) Why empathy can hold leaders back (13:21) Episode Sponsor: Bidav Insurance Group (14:16) Do MBAs matter? (16:39) Avlok’s views on emerging managers (19:27) How AngelList services large funds (21:34) AngelList Data Room and why it’s been mass adopted by funds (22:48) How managers should utilize Treasuries (25:04) AngelList’s product philosophy (27:31) How CFOs balance CEOs (29:50) What we can learn from CashApp and Square (32:08) The importance of “disagree and commit” (34:41) The fallacy of the 10% turnover rule (36:24) AngelList’s wealth of data (38:35) “Power law is a hell of a thing” (41:44) Gauging investor skillset (44:09) “The primary place where Naval lives is in building great products” (48:48) AngelList’s plans to be the system of record for all private market transactions (50:51) How to reach Avlok


    E17: Tracy Fong, Albourne Partners $700B+ AUA, on How Endowments Access Emerging Managers Nov 02, 2023
    Show notes

    Tracy Fong, partner at Albourne Partners sits down with David Weisburd to discuss how emerging VC managers can unlock institutional investors. We’re proudly sponsored by Tactyc, visit tactyc.io if you’re ready to level up your venture fund. (0:00) Episode Preview (1:06) What is Albourne and How do LP consultants work? (1:41) What Tracy has learned since joining the industry in 1999 (2:41) Learnings from the dot com bubble (5:45) Are companies now making the same mistakes present in the early 2000s? (7:03) Tracy’s tensure on the M&A team at Yahoo (10:28) Episode Sponsor: Tactyc (12:04) Yahoo’s rumored Facebook acquisition offer (14:46) How the market adjusted with YouTube and WhatsApp (17:31) How top endowments are investing (19:01) Do access constrained funds still exist? (22:22) Why being a hybrid manager is unique (23:13) Finding greenshoots in bear markets (24:38) Main investing mistakes family offices make (26:45) How to understand the market before making a venture investment (29:57) Albourne’s mission and reach (32:35) Why it’s critical to always be in the market (33:19) Why Albourne is differentiated (33:56) How to engage an LP consultant (37:48) Why fund of funds have grown in number and popularity (40:27) How to reach Tracy


    E16: Beezer Clarkson on her new $1.4B Emerging Manager Fund with CalSTRS Oct 31, 2023
    Show notes

    Elizabeth "Beezer" Clarkson, Partner at Sapphire Partners, discusses how their new partnership with CalSTRS will allow them to expand their ability to support the next generation of VC managers – all while continuing to focus on investing in the established. We’re proudly sponsored by Tactyc, visit tactyc.io if you’re ready to level up your venture fund. (0:00) Episode Preview (0:57) The Importance of LP Voices and Sapphire’s Partnership with CalSTRS (2:15) Why Investing in Emerging Managers Have Such a Unique Dynamic (4:09) The Role Emerging Managers Play in the Construction of a Compelling Portfolio (6:16) Thousands of Emerging Managers vs Forty Established Funds (7:30) Does Excess Capacity Translate to Adverse Selection? (8:17) “LPs are like Snowflakes and They’re all Different.” (10:49) Common Reasons Why LPs Don’t Re-up (13:48) What Makes for a Great Manager? (16:27) Episode Sponsor: Tactyc (17:34) What Sapphire Looks for When Evaluating a New Manager (19:00) Who Wins: Generalist v. Specialist (21:57) Will Solo GPs be able to Survive in this Market? (24:38) Beezer’s Predictions on Spinouts (26:34) The Bias and Rationale Behind Institutional LPs Desire to Re-up in Existing Managers (28:14) The New CalSTRS Program’s Investment Rubric on Checksize, Fund Size, Return Profile and Audit Requirements (30:37) How LPs Can Bring Value to a Fund (34:31) Why LPs are All Examining Their Portfolios (36:42) Should GPs Focus on DPI or TVPI? (39:01) Why Venture Needs More Innovation (40:19) How LPs Diligence Managers (44:15) The Importance of Transparency within the LP Ecosystem (51:57) What Sapphire Invests In (53:26) Lessons Learned from Previous Downturns


    E15: Scott Painter on His Relationship with Elon Musk and the Future of Mobility Oct 26, 2023
    Show notes

    Scott Painter, CEO of Autonomy sits down with David Weisburd to discuss how he creates value as a serial entrepreneur and why Elon Musk has been able to be successful through all his ventures. We’re proudly sponsored by Tactyc, visit tactyc.io if you’re ready to level up your venture fund. (0:00) Episode Preview (1:12) Scott’s Background and Focus on the Automotive Industry (3:15) The Highs and Lows of Being an Entrepreneur (5:01) Invest in Yourself if you Believe in Yourself (7:00) Scott’s Definition of Success (7:42) What being a “Visionary” in the Automotive Industry Means (8:59) Owning a Car Shouldn’t Equate to Soul Crushing Debt (10:26) Accessibility is a Way to Unlock Affordability (11:49) What Autonomy is at its Core (12:28) Episode Sponsor: Tactyc (14:39) Autonomy’s Business Model (17:35) Scott’s Friendship with Elon Musk (21:47) How Autonomy Benefits from EV Tax Credits (26:17) The Secret to Elon Musk’s Success (28:39) Empowering Employees by Decoupling Risk and Reward (30:21) The Future of SpaceX? (38:53) The Flywheel of Wealth Creation (39:49) Autonomy’s $100B Mission (44:25) Is An Autonomy IPO on the Horizon? (47:23) How to Contact Scott


    E14: Jason Calacanis on How He Returned 4,000X ($25K into $100MM) on a Single Investment Oct 23, 2023
    Show notes

    Jason Calacanis, founder of LAUNCH and host of the All-In Podcast and This Week in startups, sits down with David Weisburd to discuss his new fundraise and his views on the venture capital landscape. We’re proudly sponsored by Tactyc, visit tactyc.io if you’re ready to level up your venture fund. (0:00) Episode Preview (1:15) Fundraising for LAUNCH and LP investing experience (2:10) Sequoia’s investments in Twitter and Zynga (3:12) Being Sequoia’s first venture scout and earning 50% carry (4:28) Venture wealth bombs (8:06) Jason’s 4,000x investment in Uber (9:44) Loyalty in venture (10:07) Investing in Superhuman (13:15) How Jason got a 200x on an AngelList syndicate deal (14:20) Episode Sponsor (14:59) Unlocking value through secondaries (15:41) Qualities of top managers (16:23) Jason’s current fund (17:21) Aligning incentives through a GP commitment (20:54) Sourcing deals through Syndicate investments (23:56) The importance of social proof (25:04) Why deal flow is destiny (28:23) The importance of ownership (29:51) Sharp elbows in Series A and beyond (31:28) Jason’s current portfolio construction (32:29) YC's impact on venture (34:05) Playing for carry, the importance of a techstack and the myth of work life balance (36:19) Venture is a competition (37:06) Why early stage venture is not zero-sum


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