How I Invest with David Weisburd

Howard Lerman, the relentless founder and CEO of Roam, dives into the future of work by integrating AI into the modern office. He shares insights on being a 'cockroach' founder, emphasizing resilience as a key to survival. Discover how AI agents can drive productivity and the importance of company culture in recruiting top talent. Lerman explains his nightly 'founder mode' ritual and reflects on the adaptability required for success. Plus, he reveals how cultural memes influence product design and mission.

Zaid Rahman, founder and CEO of Flex, a fintech platform for mid-market businesses, shares insights from his journey as a Thiel Fellow. He discusses his 'Delta 4' philosophy for creating standout products and how Flex dramatically reduced credit underwriting time using AI. Zaid emphasizes hiring '10x talent' and the importance of first-principles thinking in recruiting. He also explores the unique challenges of servicing mid-sized companies and the ongoing evolution of fintech, branding it as just entering its prime.

Cliff Asness, founder and CIO of AQR Capital Management, shares his expertise in quantitative investing. He discusses why many investors overestimate volatility and misjudge leverage, leading to premature quitting. Asness elaborates on the complexities of hedge fund benchmarks and how high volatility strategies can mitigate risks. He compares investment decisions to hockey's goalie-pulling strategy and emphasizes the necessity for conviction and discipline during market challenges. Additionally, he reflects on the evolution of systematic investing and the role of machine learning in finance.

John Bowman, CEO of the CAIA Association, discusses the shift from traditional asset allocation methods to the Total Portfolio Approach (TPA). He highlights how institutions are adapting to optimize returns while navigating liquidity risks. With alternatives now making up over 20% of institutional assets, he warns against the pitfalls of outdated strategies. Bowman underscores the importance of financial education for advisors and the growing accessibility of these investment options for individuals. The future indeed looks different for alternative investments!

Jamie Gull, GP/Founder of Wave Function Ventures and former SpaceX engineer, shares insights from his transition into deep tech investing. He discusses SpaceX's high-responsibility culture and how fast iteration trumps careful planning in hardware startups. Jamie explains the importance of technical knowledge for deep tech founders and the myth that these ventures require excessive capital. With stories of investing in companies like Boom Supersonic, he emphasizes the evolving landscape of deep tech and the traits that make category-defining founders stand out.

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

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

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

Jim Bethea, Chief Investment Officer at the University of Iowa Foundation, manages a $1.7 billion endowment with just five staff members. He discusses the unique challenges of operating a lean team, sharing insights on asset allocation, manager selection, and the myths surrounding diversification. Jim explains why Iowa focuses on specialized asset classes, particularly the lower middle market in private equity. He offers candid advice on governance, decision-making dynamics, and when to re-evaluate investments, emphasizing the importance of building solid relationships in the investment community.

Ben Horowitz, Co-founder of Andreessen Horowitz and best-selling author, shares his insights on the future of venture capital, emphasizing that traditional models are changing. He discusses the importance of resilience in founders and building strong company cultures as key to long-term success. Ben dives into the evolving landscape of AI, crypto, and gaming, predicting how these trends will shape investment strategies. His candid stories and practical wisdom highlight what's needed to thrive in uncertain market cycles.