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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:
    E163: How Thiel Fellows Build Billion-Dollar Startups w/Zaid Rahman May 13, 2025
    Show notes

    Zaid Rahman is the founder and CEO of Flex, a breakout fintech startup that’s reinventing credit and payments for the middle market. Backed by the Thiel Fellowship and known for his “Delta 4” product philosophy, Zaid is building a multi-product platform that’s helping profitable, owner-operated businesses unlock capital and scale faster. In this conversation, Zaid breaks down how Flex is using AI to radically reduce underwriting time, why he’s obsessed with hiring 10x talent, and how “taste” and first principles thinking guide everything from product design to risk management. If you’re building in fintech, hiring in tech, or just obsessed with the craft of company-building, this episode is full of tactical insight.

    Highlights:

    • The Delta 4 framework: how to build products people rave about
    • Flex’s competitive edge vs. Brex, Ramp, and legacy banks
    • How Flex slashed credit underwriting time from 25 days to 48 hours using LLMs
    • Why Zaid believes fintech is “still day one” in 2025
    • How to spot first-principles thinkers in interviews (and why “best practices” is a red flag)
    • Why Flex targets the “jumbo shrimp” of the middle market
    • How Zaid built a 250+ member Thiel Fellow community from scratch
    • The real cause of burnout—and how to build a sustainable high-performance culture

    --

    Guest Bio: Zaid Rahman is the founder and CEO of Flex, a fintech platform serving mid-market businesses with credit, payments, and financial tools. A recipient of the prestigious Thiel Fellowship, Zaid previously founded multiple startups and is known for his rigorous hiring philosophy, taste-driven leadership, and commitment to building “Delta 4” experiences.

    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 @JuniperSquare for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #assetmanagement

    --

    Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd Zaid Rahman: @zaidrmn

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Zaid Rahman: ​​ https://www.linkedin.com/in/zaidrahman/

    --

    Links: Flex: https://www.linkedin.com/company/flex-super-app/

    --

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

    (0:00) Episode preview (2:14) David Weisburd: Benefits of the Teal fellowship and creating a WhatsApp group for fellows (4:44) David Weisburd: Using AI for credit underwriting at Flex (8:14) David Weisburd: AI's impact on efficiency and differentiating Flex from competitors (11:36) David Weisburd: Recruitment strategy and identifying team members with good taste (20:59) David Weisburd: Evaluating candidate contributions and defining unique positions (24:44) Understanding customer priorities and the importance of first principles thinking (27:09) Learning through interviews and the challenge of finding the right hire (31:06) Balancing expertise and culture fit in hiring and the role of non-10x employees (38:23) Addressing burnout in a high-intensity work environment (40:54) The future of FinTech and Flex's vision (46:27) Closing remarks

    E162: Why Most Investors Quit Before Winning w/Cliff Asness May 09, 2025
    Show notes

    Cliff Asness is one of the most influential minds in quantitative investing and the Founder, Managing Principal and Chief Investment Officer at AQR Capital Management, which oversees over $100 billion in assets. In this wide-ranging conversation, we go deep into what makes a successful long-term strategy, how Cliff thinks about building portfolios, and why most investors misjudge both volatility and leverage. He also shares what it was like launching AQR after his early work on momentum strategies at Goldman Sachs, and what he’s learned about investor behavior across cycles. This is one of the most insightful and entertaining conversations we’ve had on the podcast—and Cliff brings both humor and hard-earned wisdom to the table.

    Highlights:

    • Why most investors are under-levered—and how Cliff thinks about smart leverage
    • The origins of AQR’s first strategies and his early momentum research
    • The problem with how investors benchmark hedge funds
    • Why high volatility strategies can actually reduce risk
    • The truth about hedge fund alpha—and why most funds are just “half-hedged”
    • The “pull the goalie” metaphor and taking rational risks under pressure
    • What AQR does (and doesn’t) believe in when it comes to machine learning
    • Cliff’s view on how to build portfolios that survive 3-year drawdowns Why he thinks the best portfolios often don’t look great in the short run

    --

    Guest Bio: Cliff Asness is the founder, Managing Principal, and Chief Investment Officer at AQR Capital Management. He holds a PhD from the University of Chicago, where he studied under Eugene Fama and Kenneth French. Cliff is widely recognized for his groundbreaking work on momentum investing and factor-based strategies, and he’s one of the most cited voices in modern quantitative finance. He has published extensively in academic journals and is known for his bold, sometimes contrarian takes on investing and market behavior.

    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 @JuniperSquare for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

    --

    Stay Connected: Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Cliff Asness: https://www.linkedin.com/in/cliff-asness/

    --

    Links AQR: https://www.aqr.com/About-Us/OurFirm#firmfacts

    --

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

    (0:00) Episode preview (0:49) Managing institutional portfolios and the "pulling the goalie" metaphor (3:02) Challenges and psychology in maintaining investment strategies (8:25) Portfolio strategy combination and client preeducation (11:36) Continuous strategy improvement and balancing conviction (18:20) Handling drawdowns and hypothesis testing (21:05) Stress management and communication in fund management (29:09) Hedge fund transparency and strategy development (31:01) Hedge fund performance analysis and misconceptions (39:43) Applying valuation and momentum across markets (43:21) Risks and evolution of arbitrage and quant strategies (47:27) Machine learning and NLP in investment strategies (50:19) Data mining, alternative data, and future-oriented strategies (56:13) Integrating different investment strategies into products (1:03:11) Leverage importance and risks in investing (1:10:30) Managing high volatility strategies in portfolios (1:17:17) Complexity as a virtue and market efficiency catalysts (1:24:42) Long-term strategy mindset and AQR's future (1:28:01) AQR's competitive advantage and recruitment (1:30:03) Closing remarks

    E161: The Death of Modern Portfolio Theory? w/John Bowman May 06, 2025
    Show notes

    John Bowman, CEO of the CAIA Association, joins How I Invest to discuss the most important shift in institutional investing: the move from the traditional bucketed approach to the Total Portfolio Approach (TPA). In this episode, we go deep on how allocators are modernizing portfolio construction, why liquidity might be a hidden danger, and what the future of alternatives will look like as trillions of dollars flow from public to private markets.

    Highlights:

    • TPA vs. SAA: Why institutions are moving beyond traditional asset allocation.
    • Liquidity Trap: How too much flexibility can hurt returns.
    • Diversification Myth: Buckets don’t work in a world of blurred asset classes.
    • Family Office Pitfalls: Why starting with direct deals is a mistake.
    • Private Markets Boom: Alternatives now make up over 20% of institutional AUM.
    • Access for Individuals: Platforms like iCapital and Alto are changing the game.
    • Education Gap: Why advisors need to catch up as products evolve.
    • The Future: Alternatives won’t be “alternative” for much longer.

    --

    Guest Bio: John Bowman is the CEO of the CAIA Association, a global organization focused on education and professionalism in the alternatives industry. With over 14,000 charterholders worldwide, CAIA is the standard for private equity, hedge funds, private credit, and real assets. John previously held senior leadership roles at the CFA Institute and has spent decades helping institutions, advisors, and allocators navigate the evolution of the investment landscape.

    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 @JuniperSquare for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #assetmanagement

    --

    Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

    --

    Stay Connected: Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ John Bowman: https://www.linkedin.com/in/johnlbowmancfa/

    --

    Links CAIA Association: https://caia.org/

    --

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

    (0:00) Episode preview (1:45) Evolution and comparison of investment approaches (6:03) Equity risk premia and behavioral studies on portfolio management (9:55) Sponsor: Juniper Square (10:21) The changing landscape of the sixty-forty portfolio (13:55) Institutionalization and investment strategies of family offices (22:22) Behavioral psychology's role in investment and managing ignorance debt (28:15) The impact of modern education on institutional investing (31:17) Trends in allocator portfolios and the democratization of alternatives (39:29) Regulatory impacts on private capital and liquidity constraints (46:15) Predictions for the future of the alternatives industry (49:31) The critical role of diversification and understanding asset classes (53:33) The evolving skillset for investment professionals and industry competition (55:45) Dynamics of mergers and acquisitions in the investment sector (56:41) Closing remarks

    E160: How a SpaceX Rocket Engineer Became a Top Deep Tech VC May 02, 2025
    Show notes

    Jamie Gull is the GP/Founder of Wave Function Ventures, a deep tech seed fund, and an engineer turned investor who previously worked at SpaceX during its early, intense years of scaling. In this episode, Jamie and I discuss the high-responsibility culture at SpaceX, how it shaped Jamie’s approach to company building and investing, and what makes a deep tech founder stand out. We also explore why fast iteration matters more than perfect planning, how techno-economics drive investment decisions, and why deep tech’s reputation for being overly capital-intensive is becoming outdated. Jamie shares firsthand stories from his time working under Elon Musk, his angel investments in companies like Boom Supersonic and K2 Space, and the founding principles behind Wave Function Ventures. If you're interested in the future of deep tech investing, how to identify category-defining founders, or how hardware startups can scale efficiently, this is a must-listen.

    Highlights:

    • Jamie’s experience at SpaceX and the "responsible engineer" framework
    • How Elon Musk's real superpower is organizational design and culture
    • Why fast iteration beats careful waterfall planning in deep tech
    • Jamie's investment thesis at Wave Function Ventures
    • Why MBAs leading hard tech startups are often a red flag
    • Understanding techno-economics and how technical feasibility isn't enough
    • Lessons from investing early in Boom Supersonic and K2 Space
    • Why the myth of deep tech needing excessive capital is breaking
    • The role of escalation and decision-making speed at SpaceX
    • How to distinguish scientific risk from engineering execution risk

    --

    Guest Bio: Jamie Gull is the GP/Founder of Wave Function Ventures, a $10 million seed fund focused on investing in deep tech startups tackling hard hardware problems. Before becoming a full-time investor, Jamie spent over five years as an engineer at SpaceX, working on the Falcon 9 rocket, and later founded two venture-backed deep tech companies: a space deployables startup and an electric vertical takeoff and landing (eVTOL) aircraft company. His second company received eight government contracts and was acquired in 2023. Jamie combines deep engineering expertise with founder experience to help startups scale in hard tech sectors.

    Over the last several cycles, prevailing wisdom in the industry has been that hard tech companies couldn’t achieve extraordinary returns. More recently, this has been busted with the dawn of companies like SpaceX, Anduril, Saronic, etc. These companies are solving large, important societal problems, capitalizing on a perfect storm of events, from geopolitical considerations, to capital, to a massive talent influx from SpaceX and the like to government support. This theme, you can call it American Dynamism, Deep Tech, or Reindustrialization, is fueling top talent to launch and build the largest techno-industrials we have seen.

    However, investing in these areas requires specialized expertise. Enter Wave Function Ventures. WFV is a new deep-tech focused fund launched by industry veteran and investor Jamie Gull. Jamie possesses the depth and breadth of experience to position WFV to see and win the best deals in this space. He is a former SpaceX engineer who played a key role on Falcon 9 reentry, started and sold his own deep tech company, Talyn Air, that went through Y combinator, has VC experience as a Venture Partner at Pioneer Fund and Next Gen Venture Partners, and has been angel investing in deep tech companies for a decade in companies like Boom Supersonic, Varda, and K2 Space, among others.

    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.

    #VentureCapital #VC #Startups #OpenLP #assetmanagement

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd Jamie Gull: @jamiegull

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jamie Gull: https://www.linkedin.com/in/jamie-gull/

    --

    Links: Wave Function Ventures: https://www.wavefunction.vc/ Email: info@wavefunction.vc

    --

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

    (0:00) Episode preview (2:16) Role and downsides of the responsible engineer framework (5:52) SpaceX culture and personal growth (8:43) Jamie's meetings with Elon Musk (10:38) Introduction to Wave Function Ventures (12:08) Technoeconomics and founder assessment in deep tech (19:41) Comparing power law outcomes in deep tech vs. software (21:36) Analyzing technical vs. market risk in deep tech (24:39) Second-order effects and Boom Supersonic's origin (27:16) Asking the right questions in recruitment and investment (29:28) Rapid iteration's importance in deep tech startups (32:49) Traits of successful portfolio companies (36:18) Elon Musk’s approach to organizational design (39:13) Decision-making and investing strategies at SpaceX and Wave Function Ventures (41:14) Closing remarks

    E159:How a 24-Year-Old VC Landed Cendana Capital as a Limited Partner w/Paige Doherty Apr 29, 2025
    Show notes

    Paige Finn Doherty, Founding Partner of Behind Genius Ventures, joins the How I Invest podcast to share how she built one of the most distinctive brands in early-stage venture capital — all before turning 25. Paige talks about the power of content and community, how her engineering background shaped her investing style, and why being deliberate about media strategy can transform access to top founders and LPs. She also breaks down her investment thesis around AI in overlooked industries, the importance of institutional-grade operations from day one, and what it really takes to build a lasting venture firm.

    Highlights:

    • How Paige landed Sandana Capital as a cornerstone LP at just 24 years old
    • The "substance and vibes" approach to getting LPs to say yes
    • How media scaled her reach with both founders and investors
    • Behind Genius Ventures’ investment theses: "technical storytellers" and "clipboard companies"
    • What founders of billion-dollar companies have in common
    • Building a resilient brand through storytelling, community, and consistency
    • Why Behind Genius invests in embodied AI and AI agents
    • How Paige thinks about sourcing deals from TikTok to co-investor networks
    • Best practices for building a strong brand as an emerging manager on Twitter (now X)
    • Why investing in institutional-grade back office systems from day one matters
    • The vision for Behind Genius' next phase: high-production visual storytelling

    --

    Guest Bio: Paige Finn Doherty is the Founding Partner of Behind Genius Ventures, a venture firm she launched at 22 years old to back early-stage technical storytellers building in overlooked industries. She’s the author of Seed to Harvest, a children's book about venture capital, and the host of the Seed to Harvest podcast. Paige is known for her deep conviction in building brands, fostering community, and bringing an engineering mindset to portfolio construction. Through her thought leadership, content, and investing, she’s shaping the next generation of venture capital.

    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 @Republic for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

    All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd Twitter: https://x.com/paigefinnn

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Paige Doherty: https://www.linkedin.com/in/paigedoherty/

    --

    Links: Seed to Harvest the Book: https://www.amazon.com/Seed-Harvest-Explanation-Venture-Capital/dp/0578906457/ Behind Genius Ventures: https://www.behindgeniusventures.com/ Behind Genius Podcast / Youtube: https://www.youtube.com/channel/UCOsbv-4bWVXIqPQAp2BCf8Q The Technical Storyteller: https://www.behindgeniusventures.com/post/technical-storyteller What it Takes (Billion Dollar Exit): https://www.behindgeniusventures.com/post/what-it-takes-1 Clipboard companies: https://www.behindgeniusventures.com/post/clipboard Cold Outreach: https://paigefinndoherty.com/2020/03/25/a-cold-outreach-workshop/ Fortune Fund II Launch: https://fortune.com/2024/04/23/behind-genius-ventures-raises-second-fund-8-million/ Term Sheets Viral Thread: https://x.com/paigefinnn/status/1255208492312358912

    --

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

    (0:00) Introduction and guest overview (0:55) Paige's passion for venture capital and Behind Genius Ventures' differentiators (4:08) Securing top LPs and media strategy for branding and deal flow (10:39) Sponsor: Republic partnership with Hamilton Lane (11:05) Taking a stand in venture capital and advice for diverse figures (15:54) Solo GP vs. joining a top fund and value add to portfolio companies (20:12) Thesis on AI in antiquated industries and sourcing strategy evolution (26:17) Building a brand on Twitter: Strategies for VCs (30:13) Institutional service providers, LP relations, and future storytelling plans (35:03) Closing remarks and gratitude

    E158: How to Find the Right LPs for Your Next Fund w/Meghan Reynolds Apr 25, 2025
    Show notes

    Meghan Reynolds, Partner and Head of Capital Formation & Talent at Altimeter, has spent over 20 years at the intersection of GPs and LPs, helping some of the largest firms in the world raise capital, navigate investor relationships, and scale their strategies. In this episode, she breaks down what it takes to be a best-in-class capital raiser—how to expand into new strategies, find the right investors (not just any capital), and build enduring partnerships in a hypercompetitive environment. We also talk about what’s changed in the last 20 years, how the best GPs handle crisis communication, and why building a brand as an investor matters more than ever.

    Highlights:

    • The difference between capital formation and investor relations—and why many GPs get it wrong
    • How fund strategy changes impact the investor base
    • Why the most strategic capital isn’t always the largest check
    • Lessons from educating LPs about private equity in the early 2000s and private credit in the 2010s
    • The real reasons LPs don’t re-up: performance vs. transparency
    • Why geography, regulation, and timing matter in capital campaigns
    • How investor communication has evolved with tools like WhatsApp and Zoom
    • The enduring value of warm introductions in LP fundraising
    • Why small LPs might one day become your biggest supporters

    --

    Guest Bio: Meghan Reynolds is a Partner and Head of Capital Formation & Talent at Altimeter, a technology-focused investment firm. She leads the firm’s capital formation efforts and has previously held senior roles at TPG and Goldman Sachs. Over her two-decade career, Meghan has built deep relationships across the LP landscape, spanning sovereign wealth funds, pensions, endowments, and family offices. She is known for her insights into how firms scale, evolve their strategies, and communicate effectively with 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 @Carta and @Republic for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/fundtax

    Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

    All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Meghan Reynolds: https://www.linkedin.com/in/meghankreynolds/

    --

    Links: Altimeter: https://www.altimeter.com/home

    --

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

    (0:00) Episode preview (0:38) Strategic investment and capital formation (3:13) Launching and evolving fund strategies (5:28) Identifying new capital sources (8:52) Educating investors in private markets (12:25) First movers advantage vs. track record (18:13) Reasons LPs leave a fund and the importance of transparency (23:00) Enhancing LP communication and trust (27:27) Building trust through transparency and empathy (29:06) Equity and involvement in investor relations (31:31) Streamlining LP communication with tools (33:18) Capital allocation strategies and diversification (37:06) Geographic diversification strategy (41:47) Accessing and developing new LP relationships (47:00) Leveraging media and social media for fundraising (51:05) Internal and external communication strategies (55:00) Insights for LPs and staying connected (56:52) Closing remarks

    E157: DA Wallach: Spotting Genius in Elon & Zuck's Early Days Apr 22, 2025
    Show notes

    D.A. Wallach’s journey is one of the most unconventional paths in venture capital. He went from fronting a rock band discovered by Kanye West and Pharrell, to investing in Spotify, SpaceX, and founding a biotech VC firm reshaping human medicine. In this episode, we dive into his evolution—from artist to investor—and what he’s learned from being in the room with Mark Zuckerberg, Elon Musk, and Ron Burkle. D.A. shares why great investing is an act of taste, how he earned his first big break with Ron Burkle at Inevitable Ventures, and why he believes biotech is the most exciting place to invest over the next decade. We also discuss how aesthetic intuition applies to investing, how to think in second and third order effects, and what it really means to be contrarian when contrarianism has gone mainstream.

    Highlights:

    • How D.A. invested in SpaceX after meeting Elon Musk socially in LA
    • Lessons from working with Spotify, including his invented role as “artist-in-residence”
    • What he saw in Facebook in the early days and how he used it to grow his band
    • How Kanye West and Pharrell discovered his music and launched his career
    • The backstory behind raising capital for Spotify and meeting Ron Burkle
    • What made Ashton Kutcher and D.A. uniquely valuable investors at the time
    • Why he pivoted from tech into life sciences and started a healthcare-focused VC firm
    • The importance of developing aesthetic judgment as an investor
    • How to think about portfolio construction in biotech vs. software
    • Why investing is mostly about people—and what pattern recognition D.A. uses
    • The subtle power of learning from failures and “almost mistakes”
    • How to be truly contrarian in an environment where contrarianism is trendy

    --

    Guest Bio: D.A. Wallach is a venture capital investor and former recording artist. Discovered by Pharrell Williams while at Harvard, he toured with artists like Lady Gaga and Blink-182 and released music through Interscope and Capitol Records. In 2011, he shifted to investing, backing companies like Spotify, SpaceX, Ripple, and Neuralink. Today, he focuses on biotech and healthcare as co-founder of Time BioVentures. Named to Forbes' “30 Under 30” and Fast Company’s “100 Most Creative People,” D.A. also co-founded the Franca Fund for preventive genomics and appeared in the film La La Land.

    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 @Republic for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

    All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

    --

    Stay Connected: Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ D.A. Wallach: https://www.linkedin.com/in/dawallach/

    Links Time BioVentures: https://www.timebioventures.com/

    --

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

    (0:00) Episode preview (2:00) Elon Musk's early views on AI and building SpaceX (4:18) Transition from music to investing and collaboration with Spotify (7:17) Leveraging Facebook for a band’s success and networking strategies (12:06) Mark Zuckerberg's early projects and the rise of Facebook (14:39) Contrarianism and its role in modern investing (19:22) How a music background influences investment decisions (22:32) Working with Ron Burkle and Inevitable Ventures (27:17) The journey of learning venture capitalism (30:10) Assessing higher-order effects in investments (31:52) The critical importance of investing in people (33:17) Diving into healthcare and biotech investing (36:46) Portfolio strategies in biotech versus traditional venture capital (39:38) How to compete with major biotech firms (44:40) The advantages of being surrounded by top performers (46:58) Learning from near-misses and investment failures (48:25) Closing remarks

    E156: Inside the Mind of a $1.7B Endowment CIO w/Jim Bethea Apr 18, 2025
    Show notes

    Jim Bethea oversees $1.7 billion at the University of Iowa’s endowment—and he does it with a team of just five people. In this episode, we cover how Jim thinks about asset allocation, governance, manager selection, and why Iowa has decided to specialize in certain asset classes like lower middle market private equity. This conversation is full of nuance, clarity, and hard-earned lessons that every allocator, GP, and fund manager will benefit from. Jim pulls back the curtain on how small teams can still invest in niche, high-performing funds, how to manage investment committee dynamics, and why more isn't always better when it comes to diversification.

    Highlights:

    • The pros and cons of managing a $1.7B portfolio with a lean team
    • Why Iowa focuses on areas where they can outperform by 300 to 1,000 basis points
    • How to evaluate a new asset class and build relationships with experts
    • The myth of diversification and why over-diversification is often expensive beta
    • Jim’s philosophy on manager selection—and why governance matters more than most realize
    • How incentives (or lack thereof) impact committees and investment staff
    • The discipline embedded in illiquidity and why private markets can help prevent bad decisions
    • Why Iowa prefers smaller private equity funds and the edge in lower middle market
    • A candid discussion on when to re-up with top performers and when to walk away
    • Jim’s take on fund-of-funds, venture exposure, and building a durable investment operation in Iowa City

    --

    Guest Bio: Jim Bethea is the Chief Investment Officer at the University of Iowa Foundation, where he manages a $1.7 billion endowment. With over 15 years at Iowa and a deep background in both consulting and investment banking, Jim has crafted a concentrated strategy that punches well above its weight. He’s a respected voice among endowment CIOs and a strong advocate for information-sharing and collaborative learning in the LP community.

    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 @Republic and @Carta for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

    All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

    Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/fundtax

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jim Bethea: https://www.linkedin.com/in/jim-bethea-cfa-caia-b90302177/

    --

    Links: IOWA: https://uiowa.edu/

    --

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

    (0:00) Episode preview (2:41) Deciding on new asset classes and information bartering (7:05) Governance and its impact on investment returns (11:11) The role of investment committees and incentives (20:50) Analyzing top and bottom performers in portfolios (24:15) Educating the investment committee and higher concentration strategies (30:28) Co-investment interest and its impact on due diligence (32:14) Diversification versus concentrated portfolio risk and consultant incentives (37:49) Lessons from past market cycles and using fund of funds (42:13) Picking asset classes for alpha and time commitment in underwriting (44:06) Balancing alpha-generation with indexing in public equities (47:05) Liquidity considerations: Asset or liability? (51:00) Behavioral finance and maintaining investment discipline (55:26) Evaluating private equity returns in a competitive market (1:00:12) Specializing in lower middle market private equity and associated risks (1:07:51) Private credit investment climate and technical default issues (1:08:09) Overcoming early challenges and importance of in-house knowledge (1:09:39) Relationship dynamics between GPs and LPs and understanding underperformance (1:10:36) Turnaround stories and the value of investing in smaller funds (1:11:31) Closing remarks

    E155: Ben Horowitz: "The Classic VC Model Is Done” Apr 15, 2025
    Show notes

    In this thought-provoking debut episode of Turpentine VC, Erik sat down with Ben Horowitz, Co-Founder of Andreessen Horowitz, to explore the evolving landscape of venture capital, leadership, and the future of innovation. Ben shares his insights on navigating market cycles, building resilient companies, and the role of culture in long-term success. This conversation, recorded live at a16z’s Menlo Park offices in 2023, is packed with practical wisdom and candid stories from one of Silicon Valley’s most influential investors.

    Highlights:

    • VC Market Insights: Ben’s perspective on the current venture capital landscape and how it compares to previous cycles.
    • Leadership Lessons: How to manage effectively during uncertain times and build resilient companies.
    • Founder Resilience: The key traits that drive founders to succeed and how to foster resilience.
    • Company Culture: Why culture is a competitive advantage and how to build a strong one.
    • Investment Strategy: Insights into Andreessen Horowitz's approach to finding and backing standout startups.
    • Future Trends: Ben’s predictions on AI, crypto, and other emerging technologies.

    Guest Bio: Ben Horowitz is a Co-Founder and General Partner at Andreessen Horowitz (a16z), one of the most prominent venture capital firms in Silicon Valley. He is also the author of best-selling books "The Hard Thing About Hard Things" and "What You Do Is Who You Are." With decades of experience as an entrepreneur, CEO, and investor, Ben is a leading voice in the startup and VC ecosystem.

    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 @OldCityInvestmentPartners and @Republic for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #AssetManagement – Sponsor: Alpha on the Delta is a captivating, invitation-only alternative investment conference held during New Orleans' legendary JazzFest. Now in its third year, it brings together 150 institutional LPs, 30 leading GPs, and visionary entrepreneurs for a dynamic experience of knowledge sharing, relationship building, and cultural celebration.

    The carefully curated agenda features engaging panel discussions with industry leaders, facilitated 1:1 meetings, and exciting social events showcasing the vibrant spirit of New Orleans. Attendees also enjoy access to Weekend 2 of JazzFest, offering an unforgettable blend of world-class music, cuisine, and connections. With limited attendance, Alpha on the Delta fosters meaningful relationships and transformative insights in an unparalleled setting.

    Join us for a packed agenda spanning the Alternative Investment industry, music, and world-class cuisine. Visit http://HowIInvestDelta.com.

    Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

    All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

    –

    Stay Connected: X / Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/

    Links: Andreessen Horowitz (a16z): https://a16z.com/ Subscribe to Turpentine VC: https://link.chtbl.com/TurpentineVC – Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.

    (0:00) Episode preview (1:48) Andreessen Horowitz's structure vs. Y Combinator's approach (4:25) Evolution and public consideration of venture firms (8:15) Alignment issues with venture firms going public (9:38) Fund sizes, market opportunities, and talent retention (15:24) Governance and future trends in venture capital (20:14) Ben Horowitz on technology trends and AI strategy (24:30) Web 3, AI development, and crypto regulatory challenges (29:18) Venture vs. multi-asset firms and LP relations (31:16) Firm strategy influenced by macro factors (32:13) Advice for aspiring venture capitalists and wartime mindset (35:53) Technology optimism and building a tech media company (39:05) Media's impact on tech and concerns about AI power concentration (41:16) Decentralizing power and closing thoughts (41:31) Closing remarks

    E154: How a First-Generation Immigrant Became a Top CIO: Paul Chai's Story Apr 11, 2025
    Show notes

    Paul Chai’s journey from first-generation immigrant to Chief Investment Officer of a $1 billion endowment is anything but conventional. In this episode, we unpack how he transitioned from aerospace engineering to managing capital, his approach to investing in “outsiders,” and the delicate balance of taking risk in hedge funds, GP stakes, and tactical trades like TALF 2.0. Paul shares how Kansas State University's endowment supports the school’s mission, why they invest in lower middle market buyouts and small hedge funds, and how they find and evaluate emerging managers.

    Highlights: How being a first-generation immigrant shaped Paul’s investment philosophy

    Why Kansas State backs outsiders—and what they look for in emerging managers

    The TALF 2.0 trade that returned 8% in 6 months—4x the bond index

    How small hedge funds and lower middle market buyouts can deliver outsized alpha

    Kansas State’s 3-bucket portfolio structure: growth, diversifiers, and liquidity

    Why investing in people is Kansas State’s highest-ROI strategy

    Guest Bio: Paul Chai is the Chief Investment Officer of the Kansas State University Foundation, where he manages the school’s $1 billion endowment. A former aerospace engineer and consultant, Paul was recruited into investing by his college roommate and spent 12 years at a family office before joining Kansas State. He leads the investment team’s efforts across public and private equity, hedge funds, tactical strategies, and more — all while supporting the university’s mission of accessible, affordable education. Paul is a first-generation immigrant and an MIT graduate.

    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 Carta, Republic and Old City Investment Partners for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

    All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

    Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/fundtax

    Sponsor: Alpha on the Delta is a captivating, invitation-only alternative investment conference held during New Orleans' legendary JazzFest. Now in its third year, it brings together 150 institutional LPs, 30 leading GPs, and visionary entrepreneurs for a dynamic experience of knowledge sharing, relationship building, and cultural celebration.

    The carefully curated agenda features engaging panel discussions with industry leaders, facilitated 1:1 meetings, and exciting social events showcasing the vibrant spirit of New Orleans. Attendees also enjoy access to Weekend 2 of JazzFest, offering an unforgettable blend of world-class music, cuisine, and connections. With limited attendance, Alpha on the Delta fosters meaningful relationships and transformative insights in an unparalleled setting.

    Join us for a packed agenda spanning the Alternative Investment industry, music, and world-class cuisine. Visit http://HowIInvestDelta.com.

    Stay Connected:

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd Paul Chai: https://www.linkedin.com/in/ppchai/

    Links Kansas State University Foundation: https://ksufoundation.org/

    (0:00) Episode preview (2:44) Building connections and motivation in fund managers (6:04) Mutual value in manager relationships and balancing manager size (9:18) Tactical investment approach, TALF 2.0 trade, and partnering with nimble managers (13:09) Trust with the board and significance of TALF 2.0 trade (16:11) Portfolio leverage, diversifiers, and hedge fund strategies (20:11) Measuring portfolio diversification and the quarterly review process (23:41) Re-underwriting and portfolio structure with investment categories (27:36) Target return, portfolio levers, and dislocation opportunities (30:59) GP stakes, endowment strategy, and managing risk with smaller fund managers (37:16) Advantages of smaller hedge funds and Kansas State's investment strategies (42:12) Personal mission and Kansas State's impact (43:22) Closing remarks

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