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Is AI destroying the software industry, or creating its biggest investment opportunity yet? David Breach is President of Vista Equity Partners, a firm managing approximately $100 billion in assets. In this episode, David explains why the recent selloff in software stocks may be missing a much larger opportunity: AI-powered digital workers. We explore Vista's repeatable playbook for creating value in enterprise software, why mission-critical products and proprietary data remain competitive advantages, and how AI could expand software's addressable market into trillions of dollars in services. David also shares how Vista evaluates software companies amid AI disruption, why incumbents may be better positioned than startups to deploy AI agents, and the career lessons that took him from selling juice to leading one of the world's largest software-focused private equity firms.

What if the biggest advantage in venture capital isn't picking winners, but getting access to them? Erik Syvertsen is GM of Asset Management and Chief Legal Officer at AngelList and Chairman of USVC. Drawing on AngelList's extensive venture investment data, Erik explains why seed and growth investing operate like two different asset classes, why the best startups often command higher valuations from the beginning, and how access drives venture returns. We explore the power law, why doubling down on winners matters, the two strategies for building successful venture portfolios, and the challenges of selling investments in breakout companies. Erik also discusses how USVC aims to expand access to private markets as companies like OpenAI, Anthropic, and SpaceX create enormous value before going public.

What if the biggest advantage in institutional investing isn’t finding better managers, but building an organization that can make better decisions over decades? In this episode, I sit down with Tim McCusker, President of NEPC, which advises on approximately $2 trillion in assets, to discuss what separates the best institutional investors from everyone else. Tim explains why even sophisticated endowments and pension funds fall into peer-driven investing, how governance and incentives shape long-term returns, and why the strongest allocators are willing to invest when others are retreating.

What if AI makes software abundant and shifts venture capital’s biggest opportunities into the physical world? Leo Polovets is a General Partner at Humba Ventures, an early-stage deep tech fund investing across robotics, defense, energy, manufacturing, and other physical industries. Leo explains why AI is commoditizing software, why hardware may capture more value as a result, and why some of the best opportunities are hiding in industries with almost no startup competition. We also discuss how to underwrite deep tech before revenue, what separates exceptional founders, the infrastructure bottlenecks created by AI, and why the biggest risk to deep tech may be its dependence on continued funding.

What happens when autonomous underwater vehicles become cheap enough to manufacture at scale? Nelson Mills is the Founder of Vatn Systems, a defense technology company building autonomous underwater vehicles. Nelson explains why undersea autonomy has lagged aerial drones, how advances in AI, navigation, manufacturing, and autonomy are changing the economics, and why Vatn is building lower-cost systems designed to operate at scale. We also discuss raising $85 million for a hardware startup, the rise of asymmetric warfare, lessons from Anduril, and what it takes to build a new defense prime.

What if AI makes the founder more important, not less? John Borthwick is the Founder of betaworks, the startup studio and venture firm behind companies including Giphy, Dots, bitly, and TweetDeck, with investments in companies including Twitter, Tumblr, Kickstarter, and Hugging Face. We break down why John now puts more weight on founders than products, how betaworks identified Hugging Face before transformers reshaped AI, and why he believes the biggest opportunity is moving toward the AI application layer. We also discuss open-source AI, AI security, the changing nature of work, and why John believes AI was discovered rather than invented. John Borthwick is the Founder of betaworks, the startup studio and venture firm behind companies including Giphy, Dots, bitly, and TweetDeck, with investments in companies including Twitter, Tumblr, Kickstarter, and Hugging Face. We break down why John now puts more weight on founders than products, how betaworks identified Hugging Face before transformers reshaped AI, and why he believes the biggest opportunity is moving toward the AI application layer. We also discuss open-source AI, AI security, the changing nature of work, and why John believes AI was discovered rather than invented.

What did Steve Jobs understand about building great companies that most founders miss? Steven Rosenblatt is Co-Founder and General Partner at Oceans, a seed-stage venture firm based in New York City. Drawing on more than two decades as an operator and investor, including his time at Apple and Foursquare, Steven shares what he learned working directly with Steve Jobs, how he separates ambitious founders from delusional ones, what drew Oceans to Etched, and why AI is creating a technology cycle unlike anything he has seen before.

What if the future of warfare is determined by who can innovate faster, not who can spend more? Ethan Thornton is the Founder and CEO of Mach Industries, a defense technology company he started after dropping out of MIT. We break down how Mach went from experimenting with roughly 20 technologies to becoming a multibillion-dollar company, why Ethan believes asymmetric technology is reshaping modern warfare, and how Pentagon procurement is evolving. We also discuss China and Taiwan, lessons from Ukraine, autonomous warfare, recruiting exceptional talent, taking risk, and why Ethan believes great founders should empower their teams rather than make every decision themselves.

What if the biggest edge in venture capital is identifying an exceptional founder before everyone else does? Will Robbins is a technology-focused venture investor and founder of Robbins Capital, where he backs companies starting at formation. Previously, Will joined Contrary as its first employee and helped grow the firm to more than $250 million in AUM. In this episode, Will explains why traditional VC brands may matter less in an AI-driven world, how he identifies exceptional founders before they have traction, why the best startups often pivot, and why reputation with founders may be the most important asset a venture investor can build.

What if the biggest opportunity in private markets isn’t backing companies—but backing the next generation of investment firms? In this episode, I sit down with Douglas Beyer, managing partner and founder of Roaring Brook Holdings, to discuss why emerging managers remain one of the most undercapitalized opportunities in alternative assets. Douglas explains how anchor capital changes fundraising dynamics, why LP relationships determine whether firms survive, and how the best emerging managers build trust through transparency and execution. We also explore GP seeding, organizational durability, and why fundraising momentum matters more than most managers realize.

Can venture capital really be turned from instinct into science? Nnamdi Okike is Co-Founder and Managing Partner of 645 Ventures, where he leads Seed and Series A investments in software and software-enabled companies. We discuss why Nnamdi believes venture investing is driven by the totality of an investor’s experiences rather than pure instinct, how 645 quantifies founder qualities, and why missionary and “non-central casting” founders can become exceptional investments. We also explore why startups need the right market inflections, how stablecoins and agentic commerce are reshaping fintech, what Nnamdi has learned across five fund vintages, and why raising too much capital at Seed can actually hurt a company.

Which competitive moats will actually survive the AI era? SC Moatti is Managing Partner at Mighty Capital and Board Chair at Products That Count. We break down what Mighty Capital learned from mapping 550 companies by defensibility, why traditional SaaS advantages like switching costs and data moats may be weakening, and why network effects and counter-positioning are emerging as powerful AI-era moats. We also discuss why SC disagrees with the conventional power-law approach to venture, how AI is transforming M&A and corporate innovation, the Product Alpha Effect behind Mighty Capital’s investment strategy, and what venture firms must change to survive the AI transition.

Are private markets still positioned to outperform public markets? Warren Gibbon is a Multi-Family Office Chief Investment Officer with deep experience across asset allocation, equity research, and portfolio management. We discuss why investors may need to re-underwrite their assumptions about private markets, how higher rates and growing competition have changed private equity, and why public-market earnings growth may be underappreciated. Warren also explains why he is more constructive on venture, what he looks for in emerging managers, the risks created by passive investing, and how he would deploy $100 million of fresh capital today.

What happens to financial analysts when AI can do the work they used to spend all night doing? Chris Ackerson is SVP of Product at AlphaSense, where he focuses on applying information retrieval, natural language processing, deep learning, and recommendation systems to search and discovery. We discuss how AI is changing the analyst role, why vertical AI can outperform general-purpose models in financial research, and why proprietary data may become one of the most important competitive advantages in AI. Chris also explains why LLMs hallucinate, how AlphaSense is using AI to conduct expert interviews, where humans still create investment alpha, and why the future of financial research may look less like software and more like an AI teammate that never sleeps.

Is private credit really in a bubble, or are investors looking for risk in the wrong place? Theodore “Ted” Koenig is Chairman and CEO of Monroe Capital, a $24 billion private credit firm. We break down how private credit grew from a niche alternative to a $2 trillion asset class, why financing shifted from banks to private credit after the financial crisis, and the two ways Ted believes lenders can generate alpha. We also discuss the flood of retail capital into private credit, why Monroe focuses on the lower middle market, the dangers of prioritizing AUM growth over investor returns, and the personal drive and tradeoffs behind building Monroe.