How I Invest with David Weisburd

In this discussion, Dave Fontenot, the Founder and CEO of HF0, shares insights on revolutionizing startup acceleration for AI companies. He explains how founders can achieve two years’ progress in just 12 weeks by eliminating distractions through a residency model. They dive into the importance of deep flow for productivity and why avoiding the hardest problems is a common challenge among even elite founders. Dave also highlights how AI changes the startup landscape and how creating soulful products relies on empathy and trust.

In this insightful discussion, Alex Ambroz, Founder and CEO of the Allocator Training Institute, shares his extensive experience in allocator education. He explores the evolution of the endowment model and reveals how top allocators detect disguised beta and hidden risks. Alex emphasizes the power of collaboration over competition among investment teams. He also touches on the significance of transparency in building trust and outlines effective strategies for on-site due diligence that can uncover critical insights during evaluations.

Uncover the secrets of elite investors as David Weisburd shares three groundbreaking principles. Discover why top performers prioritize results over consistency and how embracing cognitive dissonance can be a superpower. Learn the importance of guarding your time—it's crucial for boosting revenue. Get insights on defining a specific 'buy box' for filtering investment opportunities, attracting the right deals without the clutter. This podcast offers valuable mindset shifts for anyone eager to enhance their investing strategy.

In this discussion, Avichal Garg, Co-founder and Managing Partner of Electric Capital, shares insights derived from his experience at Google and Facebook. He argues that the future of finance will rely on stablecoins and decentralized infrastructure rather than mere speculation. Avichal highlights the importance of tracking developer activity over token prices, the impact of AI on governance, and the need for engineering-first investment strategies. He envisions a world where crypto integrates seamlessly into everyday finance by 2030, reshaping how we perceive and utilize money.

In this engaging discussion, Melvin Hibberd, Chief Investment Officer of Hunter Point Capital and former Blackstone expert, delves into the evolving landscape of GP stakes investing. He highlights the importance of trust, avoiding auction-driven dynamics, and crafting bespoke deals that prioritize long-term partnerships. Melvin shares insights on the strategic advantages of evergreen funds, proprietary deal flow, and how careful portfolio construction improves returns. His emphasis on patience and thoughtful structuring offers valuable lessons for aspiring investors.

Lloyd Blankfein, former Chairman and CEO of Goldman Sachs, shares insights from his remarkable journey in finance. He reflects on his early life in Brooklyn and overcoming rejection to eventually lead Goldman through the 2008 financial crisis. The conversation explores the importance of communication and partnership culture in decision-making, the evolving role of technology on Wall Street, and the delicate balance between risk and intuition. Lloyd emphasizes the need for adaptability in a rapidly changing market and offers career advice for navigating the future.

Vivek Ladsariya, Managing Director at Pioneer Square Labs, discusses the art of early-stage investing and being a thought partner for founders. He explains that investing before traction can yield significant returns and emphasizes the power of iteration over static ideas. Vivek also highlights how AI is transforming operational efficiencies and coding, making it accessible to non-engineers. Plus, he shares insights on shifting Series A expectations and the impact of parenthood on his investment approach, enhancing his prioritization and patience.

How does an $8B venture platform turn a 650-fund network into a repeatable co-investing edge? In this episode, Jonathan Roosevelt, Managing Director at Industry Ventures, explains how the firm evolved from a pioneer in venture secondaries into a platform combining secondaries, co-investments (directs), fund-of-funds, and tech buyout—with AUM “a little over $8B” and 25+ years in market. We break down why Series A/B/C co-investing requires a different lens than seed, how believability guides which GPs get a “stamp” for later-stage deals, and why customer calls are ground truth when underwriting mid-stage businesses. Jonathan also shares how asymmetric information and inflection points create true co-invest alpha—and when to ignore comps for N-of-1 companies. Highlights: $8B platform: Secondaries, co-invests, fund-of-funds, tech buyout 650-fund network: ~250 primaries, ~400 via LP secondaries Co-invest engine: 100% sourced from seed/early GP relationships Seed vs. mid-stage: PMF stories vs. durable unit economics Believability lens: Repeatable process before a later-stage “stamp” Ground truth: Independent customer diligence over CEO references Asymmetry & inflection: Board insights at turning points drive edge Do the unscalable: Sector depth, real customer intros, hands-on help N-of-1 underwriting: Backcast valuation from end-state outcomes Guest Bio: Jonathan Roosevelt is a Managing Director at Industry Ventures, where he focuses on originating, valuing, and managing primary fund commitments, early secondary LP stakes, and direct company investments within the firm’s Direct & Partnership Holdings strategies. Previously a Venture Partner at Industry Ventures (2017), he was promoted to Managing Director in 2019; earlier, he founded and led companies, was an early employee/VP of Sales at SoFi, and invested as an angel in Fitbit. He holds an MBA and BA from Harvard. 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 LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jonathan Roosevelt: https://www.linkedin.com/in/jroosevelt/ Links Industry Ventures: https://www.industryventures.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (0:04) Customer feedback's impact on investments (1:03) Industry Ventures' co-investment strategy (3:44) Co-investment opportunity lifecycle (7:19) Assessing investment manager credibility and diligence (17:14) Identifying exciting co-investment opportunities (19:47) Triangulating information for investment decisions (23:04) Customer enthusiasm in the investment process (27:16) Relationship significance in investment decisions (29:34) Operator vs investor perspectives in venture capital (34:01) Risk management for seed stage investments (37:10) Competing as an emerging manager in venture capital (38:43) Valuation strategies for new venture capitalists (41:18) Closing remarks

Balaji Srinivasan, an influential entrepreneur, investor, and former CTO of Coinbase, dives into provocative predictions about the U.S. dollar's decline and the advent of digital economies. He discusses how online communities may evolve into sovereign states and explains why autonomy in governance is essential. Balaji also explores how crypto can fund real nations, the lessons from China's rapid growth, and the potential for India to become a tech powerhouse. His views offer a blueprint for a decentralized future built on innovation and community-driven solutions.

Ryan Hoover, founder of Product Hunt and investor at Weekend Fund, dives into the realm of early-stage investing. He reveals how he’s productizing venture capital, sharing insights on managing 360+ LPs and the risks of a large investor base. Hoover discusses the power of ‘earned secrets’ in founders and why unconventional ideas often yield success. He emphasizes building valuable, low-pressure introductions and the importance of community in investment strategies, promising a treasure trove of wisdom for both investors and founders.