Episode #32: Is AI Coming For Your Job?, Myths About AI Native Startups, Specialist vs. Generalist Investing

In this episode we unpack three topics across the VC/Startup ecosystem: AI Is Coming for Jobs, And CEOs Are Finally Saying It: Fiverr CEO Micha Kaufman recently published one of the most candid memos we’ve seen, acknowledging AI’s very real disruption of the gig economy. We talk about what happens when leaders stop spinning AI as pure efficiency, and start confronting what’s being lost. The Myth of the AI-Native Startup: Why are so many “AI-native” companies failing to deliver meaningful results? We discuss Casey Newton’s piece on the reality of these startups, how investor FOMO is outpacing ROI, and what lessons from SaaS might apply as the hype cycle matures. Why Specialist Funds Lose Their Edge After Fund I: Nick Moran shared a sharp LP take: specialist funds often outperform early, but lose discipline as they scale. We debate whether today’s real arbitrage might be outside of AI entirely, and what long-term evolution really looks like in venture.

Episode #31: Do We Need a VC Prenup?, Lightspeed Becomes an RIA, Financing the AI Revolution

In this episode of The Learning Corner, we explore founder frustrations with venture capital and the concept of VC prenups. The discussion transitions into the blurring lines between venture capital and private equity, examining their structural differences. We delve into the evolution of venture capital, focusing on profitability and LightSpeed Venture Partners' shift to RIA status. The conversation highlights the impact of RIA status from the perspective of founders and the trend toward diversified VC firms. We also discuss the sustainability of mid-sized venture funds, with insights from The Information's AI event, and examine consumer behavior and the integration of AI into daily life.

Episode #30: Pre-IPO Company Talent Wars, Winning Fast as Fund Managers, Tariff Impact on Startup/Early Stage VC

In this episode of The Learning Corner, we delve into the impact of AI enthusiasm and tariffs on tech businesses, exploring how these factors are reshaping the landscape. Charles Hudson shares insights on talent retention challenges faced by startups. The conversation shifts to Plaid's potential public offering and the considerations for venture capital returns. We also discuss liquidity and secondary opportunities available to limited partners. The episode examines tariffs and their economic effects on startups. The episode concludes with final thoughts on the broader implications of tariffs.

Episode #29: Agentic Hunger Games, What's an Effective Board Meeting?, The Future of Angel Investing

In this episode of The Learning Corner, we begin with an introduction and welcome before diving into Ed Sim's insights on the "Enterprise Agent Hunger Games." The discussion explores the dynamics of enterprise software, the challenges posed by AI, and the competitive landscape. We examine how founders can build for scale and sustain AI tools within enterprises. The conversation shifts to reframing board meetings and Precursor's approach to supporting founders. We also touch on Halle Tecco's decision to move away from angel investing after years in the ecosystem.

Episode #28: Fund 1 Over Performance Math, Media and Content Runs VC, Fund Manager Patience

In this episode of The Learning Corner, we kick off with an introduction and overview before diving into a consolidated discussion on Fund Ones and the factors that contribute to VC success. The conversation explores how VC firms are evolving into media companies and the importance of content strategy. We also delve into the patience and emotional aspects of early-stage venture capital, highlighting market conditions and portfolio management challenges. The episode wraps up with closing remarks and expressions of gratitude.

Episode #27: Shopify's "Leaked" CEO Memo, Tourist Founders, Senior Partners Leaving Established Firms

In this episode of The Learning Corner, the discussion begins with an overview of AI fever and its profound implications for startups. We examine the rise of tourist founders and the role of venture capital in the AI boom, along with the mounting pressure on companies to pivot towards AI. The conversation shifts to the new phenomenon of senior partner departures from larger funds across the ecosystem.

Episode #26: Bradley Tusk Says VC Is Dead, Investor Learnings From The Last Overheated Market

This episode of The Learning Corner delves into the dynamics between founder quality and market conditions. An introduction to the podcast sets the stage for a discussion on Bradley Tusk's venture fund evolution, highlighting the hybrid model's impact. The roles and innovations in fund management are explored, emphasizing the balance between meaningful support and marketing in venture funds. The conversation then shifts to platform resources and strategies for navigating overheated markets. The episode also examines adjustments in AI investment strategies, addressing price sensitivity and the emotional commitment required in investments.

Episode #25: Startup Media Hype Circles, 11x Tech Crunch Article, Market Arbitrage in Venture

In this episode of The Learning Corner, we dive into the venture ecosystem, focusing on optics versus nuance and founder expectations. We explore acqui-hires, small exits, and alternative startup paths, emphasizing transparency. A controversy around an AI sales startup sparks a discussion on founder honesty. We also discuss capitalizing on arbitrage windows, challenges for specialists, and investing in out-of-favor categories like African fintech. The debate continues on AI-focused funds and the generalist versus specialist approach in venture capital, concluding with thoughts on supporting individual contributors.

Episode #24: LP POV on Secondaries, CoreWeave/NVIDIA Growth Loop, Questioning Traditional Reserves Strategies

This episode of The Learning Corner kicks off with an introduction and overview, setting the stage for a deep dive into Cendana Capital's unique approach to secondaries and small fund liquidity. The conversation moves on to the concept of tourist fund managers, offering insights on how founders can evaluate them effectively. The growth of CoreWeave under the influence of NVIDIA is explored, raising questions about the sustainability of AI infrastructure companies. The discussion then shifts to the challenges surrounding reserve funds and follow-on investments. The episode wraps up by examining the balance between supporting founders and adhering to investment strategy, concluding with closing remarks and gratitude to listeners.

Episode #23: Unique Revenue Channels For Vertical AI, Ghosting in Venture, Is Data Driven VC Over?

In this episode of The Learning Corner, the discussion begins with an introduction to the podcast and hosts, followed by an overview of Harvey AI's impressive $300M Series D funding round. The conversation then shifts to a TechCrunch article addressing the issue of VC ghosting and the frustrations it causes for founders. The episode also examines the tendency of AI startups to exaggerate their traction, introducing the concept of "annual curiosity revenue." Lawrence Lundy Brian's post on the future of data-driven venture capital is explored, highlighting its potential impact. The episode concludes by examining the intersection of AI, data-driven investing, and venture capital, wrapping up with a sign-off.

Episode #22: Secondaries Across Venture, Stripe's Tender Offer, Knowing How Much Is Too Much To Fundraise

The discussion turns to venture capital insights, focusing on the importance of liquidity in the ecosystem. The nuances of secondary sales and the role of employee liquidity are explored, shedding light on their significance for startup growth. Attention is given to the challenges of overfunding and the necessity for capital efficiency in startups. The episode features a thoughtful discussion on a blog post, offering additional perspectives. It wraps up with closing remarks and a note of gratitude to the listeners.

Episode #21: Anthropic's Latest Raise, Internal Turf Wars in Big Tech, IPO Alternatives In Venture

In this episode of The Learning Corner, the conversation begins with an introduction to the hosts before diving into Anthropic's recent AI funding and the competitive landscape of large language models. The discussion then addresses consumer adoption of AI tools and Google's struggles in AI development. Attention is given to the impact of internal politics on tech innovation, exploring how organizational dynamics can hinder progress. The episode shifts to trends in the venture ecosystem, focusing on IPOs and secondary liquidity. It concludes with an analysis of the evolving venture model, highlighting the increasing importance of financial sophistication.

Episode #20: AgTech and Venture Capital, Signs of a Failing Company, What The Heck Does Pre-Seed Even Mean?

In this episode of The Learning Corner, the conversation kicks off with insights into understanding the role of Agtech in early-stage investing. The discussion then moves to identifying signs that a startup might be on the brink of failure, with a focus on the critical role of product velocity. Attention is given to recognizing red flags in founder behavior that could signal potential challenges. The episode concludes with a detailed exploration of pre-seed rounds, highlighting their significance and impact on the broader venture capital landscape.

Episode #19: Venture Capital 3.0, Deciphering Early Stage Traction, 90's Tech Bubble vs. Current AI Valuations

In this episode of The Learning Corner, the discussion kicks off with an introduction to the podcast and the significance of ARR milestones in the startup journey. The conversation then transitions into the evolving landscape of venture capital in the AI era, examining AI's influence on VC operations and the unique challenges faced in pre-seed funding. The episode delves into the nuances of analyzing early-stage traction, debunking common misconceptions. A comparison is drawn between the current AI investment hype and the 1999 tech bubble, offering insights into the potential parallels. The episode wraps up with a forward-looking perspective on AI investment strategies and concluding thoughts.

Episode #18: Founders Quitting vs Stopping, The Rise of Spinout VC Funds, AngelList State of Venture Report

In this episode of The Learning Corner the episode delves into Hunter Walk's essay, exploring the critical themes of founder perseverance and timing decisions in the startup journey. The conversation then shifts to a Forbes article examining Sarah Guo's recent fundraise and the opportunity of spinouts across venture capital. The episode also reviews the AngelList state of venture report, offering a comprehensive look at current and future trends in seed and venture dynamics.

Episode #17: DeepSeek, Importance of Running a Fundraising Auction, Growing Seed Round Sizes

In this episode of The Learning Corner, the discussion begins with an introduction to the podcast, setting the stage for an analysis of DeepSeek and ripple effects across venture, the public markets and startups. The conversation then shifts to predicting the future of AI, focusing on the potential of low-cost models. The episode explores auction-based fundraising, offering practical advice for founders. The importance of maintaining an updated diligence room for founders is emphasized, followed by a discussion on the dynamics of seed rounds, where size truly matters. The challenges and tips for founders navigating large seed rounds are also covered. The episode wraps up with closing thoughts and a call to action.

Episode #16: Pre-Seed/Seed M&A Activity, Solo Founders, Harvey $3B Raise, Fund Performance Recalibrations

In this episode of The Learning Corner, the conversation begins with an engaging overview of the current venture ecosystem, setting the stage for a discussion on M&A trends in venture capital. The focus then shifts to the unique challenges and dynamics faced by solo founder startups. The episode explores the rise of legal AI startups and their significant impact on the industry, followed by insights into AI's broader influence on professional services. The discussion also addresses how to navigate valuation resets within the venture capital landscape. The episode concludes with thoughtful closing remarks, bringing together the key themes explored.

Episode #15: Andrea Funsten, Robert Vinall, Manny Medina

In this episode of The Learning Corner, the conversation opens with a warm welcome, setting the stage for an exploration of transparency in venture capitalists' investment memos. The discussion then transitions to a presentation on the lessons learned from mistakes of omission in investing, offering valuable insights into recognizing and avoiding missed opportunities. The episode also delves into a LinkedIn post discussing the intersection of SaaS founders, AI, and evolving business models, highlighting the innovative ways these elements are reshaping the industry.

Episode #14: The Information, TechCrunch, LifeSciVC (shared by Jay Ripley)

In this episode of The Learning Corner, the discussion kicks off with insights into venture financing, setting the groundwork for a deep dive into Bench's shutdown and the dynamics between investors and founders. The conversation then navigates the complexities of venture debt, highlighting potential pitfalls, and addresses trust issues in founder-investor relationships. An exploration of Silicon Valley's unique venture capital landscape is followed by strategies tailored for non-Valley founders. The episode also delves into venture capital economics and fund strategies, comparing exits in biotech and emerging sectors.

Episode #13: Rob Go, Zain Rizavi, New York Times

This is the last episode of 2024 for The Learning Corner, and it's packed with great insights from across the ecosystem. The discussion first shifts to the dynamics of founders choosing firms and people, offering recommendations for repeat founders and insights into risk assessment. The episode delves into investment strategies, emphasizing timing and due diligence, and compares public and private market investing. An exploration of the history and evolution of venture capital is provided, alongside an analysis of founder preferences and decision-making. The dialogue highlights significant learning moments and predictions for the venture ecosystem, wrapping up with closing remarks and expressions of gratitude.