Founders in Arms

George Kailas, CEO and founder of Prospero AI, builds simplified market signals and data-driven research for retail investors. He discusses whether retail traders can beat ETFs, how retail activity and algos shape markets, Prospero’s ten-signal system, why data is becoming the real moat in AI, and pitfalls of AI stock-picking and “free” broker models.

Andy Chen is the co-founder of Outcast Ventures, an early-stage fund focused on rethinking how founding teams come together. Prior to Outcast, he worked across recruiting and venture capital, including roles at Riviera Partners, Kleiner Perkins, and Coatue, where he was a General Partner. At Outcast, he’s building a talent-first approach to company creation, including a co-founder matching program designed to help founders form stronger teams from the start.What you'll learn:Why choosing a co-founder from your existing network can lead to weaker outcomesThe data behind why strangers can make better co-foundersWhat actually makes a billion-dollar founding teamWhy Andy evaluates the team before the idea when investingThe key ingredients: skill, interest, and timing alignmentWhy solo founders rarely build generational companiesHow AI is enabling a new wave of high-revenue, small-team businessesThe evolution of venture capital — and what might come nextAndy’s unconventional path into venture, including time in government (as shared in the episode)In this episode, we cover:(00:00) Why successful founders struggle to find co-founders (00:28) Introduction to Andy Chen and Outcast Ventures (01:17) Andy’s path into Silicon Valley (03:23) Building Outcast and rethinking founder formation (04:19) Research on co-founder success (and what most people get wrong) (06:25) Why working with your co-founder before can hurt outcomes (07:47) Skill, interest, and timing alignment in founding teams (08:22) Inside Outcast’s co-founder matching model (10:24) Why existing co-founder platforms often fall short (11:23) Talent vs. finance backgrounds in venture capital (13:37) Why the team matters more than the idea (14:47) How venture capital has evolved over time (17:48) Rethinking the “atomic unit” of startups (19:20) AI, enterprise vs. consumer, and new opportunities (24:49) The rise (and limits) of solo founders (27:48) The future of venture in the AI era (30:33) Rapid fire: trends, feedback, and lessons (34:20) Andy’s experience working in government (37:45) Why everyone should try building something

David Rusenko is the founder and CEO of Leap Forward Ventures, a pre-seed and seed climate tech fund investing in energy, deep tech, and the reinvention of industrial processes. Before that, he spent 14 years as co-founder and CEO of Weebly, growing it from a college project to a platform serving tens of millions of small businesses before selling to Square in 2018.What you'll learn:Why Weebly stayed cash flow positive from early 2009 and what that meant for how they built the companyHow David thinks about dilution — and why inefficient spending is where founders actually lose equityThe three headcount breaking points every CEO hits and how your role has to change at each oneWhy small businesses need owned channels and how marketplaces eating their margin is the defining tension in that marketWhat clean tech investing looked like during the Vinod Khosla era vs. how David approaches it nowWhy solar's cost curve looks nothing like oil's over the last 100 years — and what that means for timingHow David thinks about nuclear's role alongside renewablesWhat made the Weebly acquisition to Square work when most acquisitions don'tHow word of mouth drove 80%+ of Weebly's growth and why that's hard to explain to investorsWhy David moved from operating to investing — and what the coach-on-the-sidelines framing means to himIn this episode, we cover:(00:00) Cash flow positivity and dilution(01:08) Introduction to David Rusenko and Leap Forward Ventures(04:11) What Leap Forward Ventures invests in(05:32) Why climate tech goes through investment cycles(07:09) Oil price vs. solar cost curves over 100 years(09:08) Clean tech timing and the dot-com parallel(10:31) David's take on nuclear energy(12:29) Why David moved from operating to investing(13:45) Reflections on the Weebly acquisition(15:13) The small business owned channel problem(17:57) CEO breaking points at 25, 75, and 175 people(20:02) What happens to your jokes at 75 employees(22:55) Designing culture intentionally as you scale(28:18) Keeping politics out of your organization(32:50) Weebly's lowest points and near-death moments(37:27) Bootstrapping vs. VC — David's actual view(40:18) How Weebly grew: mostly word of mouth(43:04) The three phases of an S-curve market(44:13) What made the Square acquisition work(48:30) Rapid fire

Ryan Gariépy, co-founder and former CTO of Clearpath Robotics and Otto Motors, with decades building mobile robotics and scaling hardware startups. He discusses bootstrapping robotics businesses, why robotics progress stacks across systems, manufacturing choices, the realities and economics of humanoid robots, and how long-term growth and experience differ in robotics versus software.

Marco Zappacosta, co-founder and CEO of Thumbtack who built a major home‑services marketplace, discusses AI transforming the platform from search to personalized matchmaking. He contrasts grounded practitioners with speculative futurists. Conversation covers AI leveling word‑of‑mouth, why high‑trust purchases need choice and confidence, and Thumbtack’s long arc from 2008 to IPO planning.

Noah Smith, writer and economist behind Noahpinion, offers data-grounded takes on AI and the economy. He explains why a viral Citrini post rattled markets, why a 2008-style AI crash is unlikely, and how a productivity boom could oddly trigger a mild recession. He also names AI-enabled bioterrorism as his top worry and dissects hiring shifts and job risks in tech and blue-collar sectors.

Parag Agrawal, co-founder and CEO of Parallel and former Twitter CEO, builds infrastructure so AI agents can access and act on the open web. He explains why agents will become primary web users. Topics include Parallel’s APIs for agent automation, the shift from pull to push web alerts, new monetization for publishers, the rise of autonomous sub-agents, and the company’s stealth-to-scale fundraising story.

Vishwas Prabhakara, co-founder and CEO of Honey Homes, built a subscription home maintenance service after running Yelp’s restaurant business. He explains why marketplaces fail for skilled trades. Short takes cover hiring elite, W-2 tradespeople, neighborhood-focused growth, altruism-driven referrals, and using AI to boost worker productivity while keeping humans central.

Max Mullen, Instacart co-founder and long-time CPO, turned grocery logistics skepticism into a massive company. He recounts founding and scaling through timing, culture, M&A, and shifting founder roles. He also maps AI’s next frontier, predicting vertical agent-driven tools that boost professionals’ productivity.

SaaS companies are down dramatically—Figma is 77% off its peak. In this candid conversation, Immad Akhund (CEO of Mercury) and Raj Suri (co-founder of Lima and Tribe) unpack what's really happening in tech as we head into 2026.They explore why the SaaS business model is under attack (hint: it's not just AI building software faster), the shift from per-seat pricing to API-driven usage, and why enterprises actually buy SaaS products—spoiler, it's not about the software. The conversation reveals how startups can now stay lean with fewer employees for much longer, with companies like OpenAI reaching $500B valuations with just 4,000 people.Immad and Raj also dive into their personal experiences with AI agents, discussing what actually works versus the hype, why they're skeptical of consumer AI hardware, and how AI is changing daily productivity for founders. They debate Google's quiet win with the Apple-Gemini deal, why Siri is dead, and whether one AI model controlling all handsets should concern us.The episode wraps with practical advice on what makes a compelling VC pitch in 2026, why crazy promises still work (even when timelines are wildly optimistic), and how to think about your startup's valuation as a call option rather than current worth. From Elon's humanoid robot bet to the new growth expectations (0 to $5M in 12 months), this conversation offers an honest founder-to-founder take on navigating the current landscape.Key Topics:Why SaaS companies are struggling and what survivesThe real reason enterprises buy software (risk offloading, not features)AI agents in practice: what works, what doesn'tGoogle's strategic win with Apple's Gemini integrationHow to pitch VCs when expectations are 5x higher than beforeWhy crazy promises and long timelines still attract capitalThe shift to leaner startups and API-first business models