The Venture Variety Show

Podcast Title:Venture in the Age of AI: Don Butler on Jobs, Tools, and the Future of VCRefined Description:Don Butler has seen a few cycles. He joined Thomvest Ventures in February 2000—just as the dot-com bubble was about to burst. Now, 25 years later, he’s watching another massive shift take hold: AI.In this episode of The Venture Variety Show, Don and I dive into how artificial intelligence is changing the way venture capital firms operate—from sourcing and diligence to hiring decisions and team structure. We explore the tools Thomvest is using today, how they're thinking about staffing in an AI-first world, and why solo GPs backed by AI assistants might be the new normal.We also talk about the human side of this transformation: what jobs are at risk, where new roles are emerging, and how behavior is already shifting in response to AI-powered systems.If you’re a founder, investor, or just curious how AI is rewiring the VC industry from the inside out, this episode is for you.Key Topics:Why Thomvest no longer hires analystsThe rise of AI agents and what they’re replacingHow generational wealth transfer is transforming wealth managementWhat “AI Associates” mean for firm structure and solo GPsWhy understanding model drift matters in agentic systemsBehavioral surprises from voice agents and what they reveal Get full access to The Venture Lens at agoldfisher.substack.com/subscribe

Show Notes – The AI Cognitive Shift: Xiaoyin Qu, heyBossAIGuest: Xiaoyin Qu, founder of heyBossAIHost: Alastair GoldfisherLength: ~30 minutesOriginally recorded for The AI Cognitive Shift (in collaboration with AiNews.com)In this episode:Xiaoyin Qu made headlines by stepping down as CEO of heyBossAI and handing the role to an AI agent named Astra. In this conversation, she shares the thinking behind that bold decision—and what it means for the future of leadership, automation, and trust.We discuss:Why Astra was outperforming human execs on key tasksWhat it’s like to lead a team of AI “employees”How heyBossAI serves customers in 30+ languages—at lightning speedWhy some clients still want the human touch, even in an AI-first companyThe legal and ethical limits of AI in leadership rolesKey Takeaways:Astra builds full websites in minutes—design, backend, copy, SEO, and hostingAI can simplify entrepreneurship by lowering the barrier to launchHuman oversight remains essential for compliance, contracts, and nuanceTransparency tools (like a Slack simulation) help build customer trustThe model raises big questions about the future of work and what leadership looks like in an AI-led orgSound Bites:“AI is the new CEO.”“We are 10x cheaper, 100x faster.”“AI can replace entire teams.” Get full access to The Venture Lens at agoldfisher.substack.com/subscribe

Episode Title: Unlocking the Power of Storytelling in Venture — with Beck BambergerSummary:In this episode of The Venture Variety Show, I chat with Beck Bamberger — founder of BAM and author of the new book Flack Fairy. We dive into why storytelling is such a critical (and often overlooked) skill for venture-backed founders, how to navigate the tricky world of PR and media, and what role AI is starting to play in marketing and communications.Beck pulls no punches: while AI tools can help draft and shape content, she believes the essence of PR, fundraising, and media success still hinges on authentic human relationships. We also explore the shifting landscape of venture capital, marketing roles, and how founders can sharpen their narrative edge.Takeaways:🔶 Storytelling is a must-have skill for founders — not a nice-to-have🔶 AI can help, but it can’t replace human connection in PR🔶 The current VC environment is more cautious, making clear narratives even more important🔶 In-person connections and genuine relationships are more valuable than ever🔶 Founders who can “nail their narrative” stand outChapters:00:00 – Intro with Beck and Alastair04:12 – BAM and Flack Fairy06:59 – Nailing Your Narrative11:45 – The Impact of AI21:11 – Venture Outlook27:56 – OutroSound Bites:• “PR isn’t magic — it’s strategy plus relationships.”• “Founders often underestimate how much time it takes to build media momentum.”• “The best founders aren’t just fundraising — they’re storytelling constantly.”• “In a cautious VC market, clarity wins.”• “Flack Fairy is the guide I wish every founder had before their first PR push.”• “Media love a good story — they don’t love a sloppy pitch.”• “The VC world is always chasing what’s next, but the fundamentals of trust and relationships haven’t changed.”• “PR should amplify what’s real, not spin what’s fake.” Get full access to The Venture Lens at agoldfisher.substack.com/subscribe

In this episode of The Venture Variety Show, Alastair Goldfisher talks with Doug Levin — founder of Black Duck Software, Harvard lecturer, startup advisor, investor, and author of Lessons from a Startup Life on Substack.They explore how the post-ChatGPT boom has reshaped the startup world, why investors are drawn to small, nimble AI teams, and why product-market fit is a continuous process, not a one-and-done milestone. Doug also shares practical advice for founders on raising capital, avoiding common mistakes, and why you should always be thinking about your exit strategy.Topics covered:Startup lessons from Doug Levin’s entrepreneurial journeyHow generative AI is fueling a wave of new companiesFundraising strategies in today’s competitive venture marketThe evolving role of AI product managersBest practices for planning a successful exitFor more founder insights and venture trends, subscribe to The Venture Variety Show.🎧 Subscribe and follow:For more founder insights, venture trends, and conversations at the intersection of startups, AI, and investing, subscribe to The Venture Variety Show on Substack, or follow on Spotify, Apple Podcasts and YouTube.Thank you for listening!— Alastair Get full access to The Venture Lens at agoldfisher.substack.com/subscribe

Title:AI, Lawsuits, and the Death of the Billable Hour? | Alon Shwartz, TrellisShow Notes:In this episode of The Venture Variety Show, I sit down with Alon Shwartz, co-founder and COO of Trellis, to explore how AI is transforming one of the oldest professions: law.Trellis is a legal tech startup using generative AI to make state trial court data searchable and accessible. Alon shares how this shift is affecting everything from legal research and billing models to the role of junior associates—and why data, not just prompts, is the real moat for AI-driven startups.This episode originally aired as part of The AI Cognitive Shift, a podcast I co-host in collaboration with AiNews.com. You can watch more episodes over on the AiNews YouTube channel.In this episode:Why legal research is now “a commodity”How AI is forcing law firms to rethink the billable hourWhat makes Trellis’ dataset so powerful—and defensibleWhy picking a model and sticking with it mattersThe challenge of training the next generation of lawyersWhat founders should ask before building with AIGuest:Alon Shwartz – Co-Founder & COO, TrellisFor more podcast episodes and posts on how AI is reshaping venture, platforms, and storytelling, subscribe to The Venture Variety Show.—Chapters:00:00 – Intro: AI and the Legal Profession01:12 – The Fragmentation of Court Data04:14 – AI’s Impact on Research, Billing & Jobs08:52 – Why Trellis’ Data Moat Matters15:14 – Future Trends and the Ethics of AI in Law—Key Quotes:“Research has become a commodity now.”“What problem are you solving with AI?”“AI will help attorneys do more.”Keywords:AI, legal industry, Trellis, legal tech, generative AI, state court data, legal research, billing models, data moat, startup strategy, future of work, platform tools Get full access to The Venture Lens at agoldfisher.substack.com/subscribe

🎧 Episode: “The Exit Bottleneck and the Path Forward”In this episode of The Venture Variety Show, I talk with Louis Lehot, a Silicon Valley-based attorney at Foley & Lardner who works closely with startups, investors, and acquirers across the venture ecosystem.We dig into what’s really holding back venture capital right now—and what might finally break things loose in 2025.In this episode, Louis shares insights on:Why DPI is stalling the VC flywheelHow founders can raise capital creatively—without waiting for the market to “settle”What’s needed for the IPO window to truly reopenThe role of risk, interest rates, and macro pressure in the return of exitsWhy debt capital and customer revenue are smart plays right nowSound bites from Louis:“2025 ought to be the year of the IPO.”“The best capital is the money that comes from customers.”“The levers of the venture capital system have been gummed up.”This was recorded before the recent tariff flare-up, but Louis’ perspective still holds up—and his advice for founders is especially sharp.🎙️ Be on the lookout for more from Louis soon—I’ll be featuring him again in an upcoming post about AI's impact on the legal profession.👉 Subscribe to The Venture Variety Show on Substack📺 Watch on YouTube | 🎧 Listen on Spotify, Apple Podcasts, etc. Get full access to The Venture Lens at agoldfisher.substack.com/subscribe

Episode Title: The Artist AI Didn't Replace - A Conversation with Daniel AmbrosiDescription: Join host Alastair Goldfisher for the inaugural episode of "The AI Cognitive Shift," a podcast series brought to you in collaboration with AiNews.com. This series delves into how artificial intelligence is reshaping our cultural and societal landscapes through intimate conversations with innovators at the intersection of technology and creativity.In this episode, we explore the intriguing world of AI and art with Daniel Ambrosi, a renowned digital artist who has harnessed AI to expand the horizons of traditional landscape photography into what he calls "AI-assisted" art. Daniel shares his journey from traditional to digital artistry, his collaboration with tech giants like Google and NVIDIA, and his thoughts on the recent controversial Christie’s auction "Augmented Intelligence."Key Highlights:Daniel's Transition to AI-Assisted Art: How a seasoned landscape photographer embraced AI to enhance the depth and emotion of his artworks.The Christie's Auction Controversy: Insights into the debate over AI-generated vs. AI-assisted art, highlighting Daniel's participation in this landmark event.Impact on Artists: Daniel discusses how AI technologies are influencing both fine and commercial artists differently.Future of Art and AI: A look at the potential advancements and ongoing challenges at the nexus of AI and creative expression.Key Quotes:"I'm an accidental AI artist. My work is not AI-generated but AI-assisted.""There's nowhere to go but up for fine artists in the age of AI.""You don’t have to worry one iota about AI affecting the livelihood of fine artists."Timestamps:00:00 | Introduction to 'The AI Cognitive Shift'01:15 | Meet Daniel Ambrosi: Journey to AI-assisted Art05:00 | Inside the Christie's "Augmented Intelligence" Auction10:30 | The Impact of AI on Art: Commercial vs. Fine Artists15:45 | The Future of AI in Artistic Expression20:00 | Closing Thoughts and What's NextCall to Action:Visit Daniel Ambrosi’s Art: Explore more of Daniel’s transformative works on his website.See Daniel’s Work in Person: If you're in the San Francisco Bay Area, check out his piece at the Computer History Museum in Mountain View.Subscribe for More: Don't miss an episode of The AI Cognitive Shift—subscribe on Spotify, Apple Podcasts, and YouTube to stay updated on how AI continues to influence our world.Keywords: AI, Art, Daniel Ambrosi, Computational Photography, Christie's Auction, AI Controversy, Fine Art, Commercial Art, Future of AI, Podcast Series Get full access to The Venture Lens at agoldfisher.substack.com/subscribe

Title: Emily Peters on Art, AI, and the Future of Health EquitySummary:In this episode, Alastair Goldfisher speaks with Emily Peters, a healthcare brand strategist and author of "Artists Remaking Medicine," about the intersection of art, technology, and healthcare. Emily shares insights from her work in the digital health space, her personal journey as a patient, and her belief in the power of creativity to drive innovation in healthcare. The conversation also explores the potential of AI to address administrative challenges and the importance of health equity, highlighting Emily's upcoming participation in the Health Equity Innovators Summit.  Key Takeaways:Healthcare is a universal concern.  AI offers opportunities to reduce administrative burdens in healthcare.  Art can foster creative problem-solving and a deeper understanding of power dynamics in healthcare.  Personal experiences, like Emily's, can motivate individuals to advocate for change in the healthcare system.  Incremental changes can lead to significant improvements in healthcare.  Community engagement and addressing systemic flaws are crucial for achieving health equity.   Get full access to The Venture Lens at agoldfisher.substack.com/subscribe

Podcast Title: The Venture Variety Show: How AI is Reshaping Venture Capital with Fred Campbell of TRAC.vcShow Notes:Episode Description:Is AI the future of venture capital? In this eye-opening episode of The Venture Variety Show, host Alastair Goldfisher dives deep into the data-driven revolution transforming the investment landscape. Alastair interviews Fred Campbell, Managing Partner and Co-founder of TRAC.vc, a venture firm at the forefront of AI-powered investing.  Fred, a self-described "reluctant VC" and former tech entrepreneur, shares his unique journey and TRAC's groundbreaking approach to identifying and funding high-potential startups.  This episode explores how TRAC uses AI to analyze market trends, evaluate startups, and make investment decisions, offering invaluable insights for entrepreneurs navigating the evolving world of venture capital.  Key Takeaways for Entrepreneurs and Investors:The Rise of AI in Venture Capital: Discover how AI and data analytics are changing how venture firms source deals, conduct due diligence, and make investment decisions.  TRAC.vc's AI-Driven Model:TRAC stands out as a 100% AI data-driven VC, where "data is our investment committee."  Learn how their technology analyzes market data and identifies promising startups with a high probability of success.  Discover TRAC’s emphasis on market timing, product-market fit, and "collective intelligence" in predicting startup success.  Crucial Advice for Entrepreneurs:Learn why claiming "no competition" is a major red flag for investors and how to effectively position your company in a competitive market.  Understand the importance of building a strong media footprint to attract investor interest.  Master the art of storytelling in pitches, combining emotional appeal with data-driven evidence.  The Evolving Venture Landscape:Explore how data-driven approaches are changing the dynamics of venture capital, potentially leading to increased efficiency and reduced failure rates.  TRAC's Unique Approach to Finding "Smart Money":Learn how TRAC’s AI identifies "SuperTRACers" - high-performing investors whose involvement significantly increases a startup's probability of success.  Quotes:Fred Campbell: "I'm a reluctant VC."  Fred Campbell: "As far as I know, TRAC is the only 100% AI data-driven VC."  Fred Campbell: "Data is our investment committee."  Fred Campbell: "Turn the equation around."  Fred Campbell: "The story is everything."  Call to Action:Listen to the full episode of The Venture Variety Show with Fred Campbell for more in-depth insights into AI-driven venture capital and actionable advice for entrepreneurs.Visit TRAC.vc to learn more about their investment strategy and access their investor research tool.  Subscribe to The Venture Variety Show for more interviews with leading voices in the venture and startup ecosystem. Get full access to The Venture Lens at agoldfisher.substack.com/subscribe

keywordsventure capital, marketing strategy, storytelling, consistency, earned media, video content, podcasting, founder support, work-life balance, authenticitysummaryIn this episode of The Venture Variety Show, Alastair Goldfisher interviews Kayla Liederbach, a seasoned VC marketing expert. Kayla shares her journey into venture capital, her experiences at SOSV, and the importance of consistency in marketing strategies for VC firms. She discusses the significance of owned and earned media, the role of video and podcasting, and what founders should look for in a VC firm. Kayla emphasizes the need for authenticity and maintaining a work-life balance while navigating the fast-paced world of venture capital.takeawaysKayla Liederbach transitioned into venture capital from a tech startup.Consistency in marketing is crucial for VC firms.Creating effective content strategies can help VC firms grow.Owned media is essential for building a VC brand.Video content adds a human touch to marketing efforts.Founders should seek VCs that offer more than just financial support.Work-life balance is important in the demanding VC industry.Authenticity attracts the right clients and partners.Alignment with personal values enhances professional success.Networking and community building are vital for VC marketing.titlesNavigating the Venture Capital LandscapeThe Art of VC MarketingSound Bites"The importance of consistency in marketing""Having a work-life balance is crucial""Alignment was my word of the year"ChaptersKeys to Successful Marketing in VCBest Practices for VC MarketingThe Role of PR in Venture CapitalEmerging Trends in Content CreationValue of Marketing for InvestorsWhat Founders Should Look for in VCsWork-Life Balance in Venture CapitalFinal Thoughts and Contact Information Get full access to The Venture Lens at agoldfisher.substack.com/subscribe