VC Aileen Lee Still Sees the Most Promise in Mundane Tech (Re-Release)

This week on StrictlyVC Download, TechCrunch EIC Connie Loizos and StrictlyVC's Alex Gove sit down with Marc Bhargava, partner at General Catalyst, to explore his ambitious $1.5 billion Creation Fund strategy that's targeting the $16 trillion global services economy through AI-powered rollups. They dive into how Bhargava's team proves AI automation works and why outcome-based pricing models are disrupting everything from legal services with Eudia to call centers with Crescendo. Plus, they discuss the mechanics of incubating AI-native companies with proven second-time founders, why relationship-driven and regulated businesses make the best targets, and Bhargava's theory that 95% of corporate AI pilots fail because applying AI technology effectively requires deep expertise that consulting firms simply can't provide. Chapters: 00:00 - Introduction and Marc's background 02:00 - From crypto to Coinbase Prime acquisition 05:00 - General Catalyst's Creation Fund strategy explained 10:00 - Fund administration vs. Carta comparison 15:00 - Titan MSP deep dive and $74M investment 20:00 - Udia's approach to disrupting legal services 25:00 - Why 95% of AI pilots fail and market opportunities 29:35 - Closing thoughts and General Catalyst's future initiatives Learn more about your ad choices. Visit megaphone.fm/adchoices

This week on StrictlyVC Download, TechCrunch EIC Connie Loizos and StrictlyVC's Alex Gove sit down with Adeo Ressi, founder of Decile Group, and Sarah Lacy, the former TechCrunch journalist turned entrepreneur to explore how one of Ressi's newest projects --  VC Lab -- has quietly launched over 800 venture funds worldwide, averaging $12 million each. In fact, while traditional media focuses on emerging manager struggles, the four talk about why, according to Ressi and Lacy, small checks are becoming strategically advantageous in over-subscribed rounds, how accomplished professionals are locked out of traditional VC despite having unicorn angel track records, and Lacy's theory that diverse manager networks are unlocking untapped LP pools. Plus, they talk about Lacy's path from Palm Springs bookstore owner back to Silicon Valley ecosystem building, whether this micro-fund renaissance can actually achieve 50/50 gender parity in venture capital, and what Ressi, a former roommate of Elon Musk, thinks about Musk's time this year in federal government. 00:00 - Introduction 03:17 - From tech journalism to Palm Springs bookstore owner 05:05 - Scaling Founder Institute and the birth of VC Lab 06:39 - The disconnect between media narratives and ground reality 07:46 - The economics of Decile Group's free model 09:54 - Fund performance: 2x returns in 24 months 12:14 - The strategic advantage of small checks 14:24 - Breaking the VC paper doll cutout 17:19 - Finding capital: From network activation to fund of funds 18:57 - Success stories: From blockchain to African women managers 23:43 - Fighting misogyny and building gender equality in VC 26:18 - From tearing down to building up 29:52 - Fixing problems at scale through democratized venture 31:45 - The Elon factor: Politics, neurodiversity, and friendship Learn more about your ad choices. Visit megaphone.fm/adchoices

This week on StrictlyVC Download, Techcrunch EIC Connie Loizos talks with Uncork Capital honchos Jeff Clavier and Andy McLoughlin. They discuss how their seed-stage firm is positioning itself in this environment, from a recent investment in AI chip maker Groq to bets on AI-native companies attacking unsexy industries like material sciences and robotics. Plus, the three dig into Uncork's philosophy of finding companies with unique datasets before they become obvious to the market, how Uncork is advising its established portfolio companies to reinvent themselves in an AI-first world, and whether San Francisco's comeback -- driven by AI moolah -- is sustainable. Chapters: 00:00 - Introduction 01:48 - Market dynamics and late-stage firms entering seed stage 04:36 - Groq investment and AI chip industry insights 08:37 - Dave Agents investment and round economics 09:20 - Current AI investment themes and portfolio evolution 10:49 - Helping established portfolio companies adopt AI 13:58 - AI's impact on workforce and productivity 17:26 - Investing in unsexy industries with unique datasets 20:52 - Robotics investments and AI-driven automation 21:42 - Competitive positioning and value proposition 25:54 - Secondary market strategy and exit timing 27:37 - Private market democratization policy discussion 31:37 - San Francisco's resurgence as AI innovation center 35:02 - Closing remarks Learn more about your ad choices. Visit megaphone.fm/adchoices

This week on StrictlyVC Download, TechCrunch Editor-in-Chief Connie Loizos speaks with Katelin Holloway, co-founder of Seven Seven Six, the generalist firm that's raised over $1 billion across three funds. They discuss Seven Seven Six's unconventional investment thesis spanning AI-powered stone carving robots to commercial lunar mining, including her bet on Interlune—the first company to sell an off-planet resource back to Earth. Holloway explains why she believes helium-3 harvested from moon dust will generate returns within a decade, how climate tech and space tech are converging in unexpected ways, and why maintaining human connection remains critical as AI transforms the workforce. Chapters: 00:00 - Introduction 01:32 - Generalist investment approach 04:00 - Monumental labs: AI-powered stone carving revolution 07:00 - Space tech investment journey and philosophy 10:00 - Interlune: mining helium-3 from the moon 15:00 - The future of space commerce and exit strategies 22:00 - Human connection in an automated world 25:00 - The changing workforce and AI platform shift 30:00 - Closing thoughts and future outlook Learn more about your ad choices. Visit megaphone.fm/adchoices

This week on StrictlyVC Download, TechCrunch Editor-in-Chief Connie Loizos and Alex Gove of StrictlyVC speak with Lara Banks, who leads venture investing at Makena Capital Management. They discuss her firm's $3 billion venture allocation across 30 manager relationships, how she evaluates everything from solo GPs to the AI rollup trend sweeping traditional service businesses, and why she thinks AI companies' "astronomical" revenue growth justifies their sky-high valuations despite massive infrastructure costs. Banks also shares what LPs really learned from 2021's boom-bust cycle and how the secondary market is creating new liquidity opportunities as companies stay private longer. Learn more about your ad choices. Visit megaphone.fm/adchoices

This week we're sharing an interview from the Equity podcast. Rebecca Bellan chatted with Deedy Das, principal at Menlo Ventures. Das has seen this shift from multiple angles, first as an engineer and product leader at Google, Facebook, and AI startup Glean, and now as an investor helping technical founders figure out how to build enduring companies in this new AI landscape. They discuss how compensation packages and acquisitions are warping startup hiring and retention and how VCs are thinking about key-person risk. Learn more about your ad choices. Visit megaphone.fm/adchoices

This week on StrictlyVC Download, TechCrunch EIC Connie Loizos and Alex Gove of StrictlyVC speak with Dimitrious Kottas, the founder and CEO of Delian Alliance Industries. They discuss his journey from Apple's Special Projects Group to building autonomous defense systems in Greece, how his company is reimagining surveillance and strike capabilities using AI and commercial tech, and why he believes we're at the start of a decade-long technological race in autonomous warfare. Chapters: 00:00 - Introduction 02:04 - Dimitrios's background and journey from Apple to defense tech 05:00 - The founding moment: Why he left Silicon Valley for Athens 08:55 - Starting with surveillance towers: The perception-first strategy 13:21 - Current deployments in Greece and Ukraine aspirations 16:32 - Dual-use applications and critical infrastructure protection 18:39 - The Intercept-Egon series: Concealed autonomous weapons 21:52 - Cost advantages through vertical integration 24:46 - European defense tech landscape and procurement challenges 28:16 - Greece's defense industry and cross-border competition 31:04 - Modular vs. full-stack approach 32:54 - Thoughts on Anduril and the defense tech race 35:00 - Greek roots and the personal nature of European defense Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode we're revisiting Connie Loizos' conversation with Aileen Lee, the founder of Cowboy Ventures. They discuss what’s on the horizon for Cowboy Ventures and how she’s thinking about AI’s impact on job creation, automation, and new business models—while also giving listeners a glimpse into Cowboy’s own recent team changes. Learn more about your ad choices. Visit megaphone.fm/adchoices

This week on StrictlyVC Download, TechCrunch EIC Connie Loizos is joined by Drive Capital co-founder Chris Olsen. Chris explains how Drive's contrarian approach to fund size, ownership stakes, and geographic focus is generating returns where others firms are right now struggling. Plus: why Silicon Valley billionaires are choosing Columbus, and what the "venture reckoning" means for the industry. Chapters: 00:00 - Introduction 01:28 - The $500M Distribution Week Strategy 03:08 - Why Venture Math is Broken for Mega Funds 05:00 - Thoughtful Automation Exit and Portfolio Returns 10:00 - Fund Strategy and Family Office Trends 12:00 - Secondary Sales and Series B Liquidity 15:00 - Post-Mark Kwame Evolution and Geographic Expansion 17:30 - Building Infrastructure Across Six Cities 18:30 - Beyond Pure Tech: AI in Traditional Industries 20:00 - Syndicate Strategy and Solo VC Approach 22:46 - 30% Ownership Stakes and Pricing Philosophy 25:00 - Silicon Valley Exodus to Columbus Learn more about your ad choices. Visit megaphone.fm/adchoices

This week on StrictlyVC Download, Alex and Connie are joined by Justin Fanelli, the Acting Chief Technology Officer for the US Navy and Technical Director of Program Executive Office Digital, where he oversees billions of dollars in IT infrastructure and cybersecurity initiatives. He's also a venture partner at NextGen Venture Partners and serves as a senior fellow for the Open Forum for AI. In this episode, they discuss the Navy's innovation adoption kit designed to bridge the "valley of death" between commercial technology and military implementation, the partnership with Defense Innovation Unit to streamline startup onboarding, and how the Navy is measuring success through new outcome-driven metrics that prioritize sailor time saved and operational resilience over traditional activity-based measurements. Chapters: 00:00 - Introduction and background 03:19 - Innovation adoption kit and valley of death solutions 05:43 - Partnership with Defense Innovation Unit (DIU) 08:27 - Onboarding non-traditional vendors and startups 13:22 - Current pain points and AI adoption challenges 15:37 - Technology modernization and team structure 17:39 - Measuring effectiveness with world class alignment metrics 21:23 - Common failure points in technology adoption 22:09 - America first policies and supply chain resilience Learn more about your ad choices. Visit megaphone.fm/adchoices