Founders in Arms

George Kailas is the CEO of Prospero AI, a platform helping retail investors make smarter decisions using simplified market signals and data-driven insights.
In this episode, George joins Immad and Raj to break down one of the biggest debates in investing today: should you just buy ETFs, or can retail investors actually beat the market?
They go deep into how modern markets really work, why retail investors are becoming more powerful than ever, and what most people get wrong about stock picking, AI tools, and “free” trading platforms.
What you’ll learn:
Why ETFs beat stock picking if you don’t have enough time
How retail investors now make up a massive share of market movement
The biggest mistake investors make: not knowing when to exit
Why analyst ratings and price targets often can’t be trusted
How platforms like Robinhood actually make money (and what it means for you)
The shift from software → data as the real moat in AI
Why AI stock-picking tools are dangerous in volatile markets
The psychology of investing: why most people need to lose before they learn

What we cover:
00:00 Should You Pick Stocks or Just Buy ETFs?
00:50 Meet George Kailas (Prospero AI)
01:30 Beating the Market with Data Signals
02:15 From Mortgage Models to AI Founder
03:20 Why Data Will Matter More Than Software
04:20 Why People Don’t Trust Analyst Ratings Anymore
05:00 Who Is Prospero Actually Built For?
05:45 Value Investing vs Modern Momentum
07:00 The Big Debate: ETFs vs Stock Picking
07:35 The 1-Hour Rule: When You Should NOT Pick Stocks
08:30 Retail Investors Are Driving the Market Now
09:30 How to Actually Learn Investing (Without Losing Everything)
10:40 Why Exiting Trades Is the Hardest Skill
11:25 Are Public Markets Really Mispriced?
11:55 Why Analyst Price Targets Can’t Be Trusted
13:05 Inside Prospero’s 10 Signals System
14:10 How They Simplify Complex Market Data
15:10 Risk Signals: When to Exit a Trade
16:30 How Traders Use Options, Sentiment & Dark Pools
17:30 Are Apps Like Robinhood Good or Bad?
18:10 The Hidden Cost of “Free” Trades
19:30 Why Retail Investors Lose Power Through Brokers
20:10 Better Alternatives to Robinhood
21:40 AI, Data, and the Future of Investing
23:00 Why Intent Data Could Change Everything
24:40 AI, Layoffs & Wealth Inequality
26:00 The Rise of Crypto Traders & Risk Culture
27:10 Why Some Investors Need to Lose First
29:00 Why AI Tools Are Bad at Risk
30:00 Mercury’s Investing Strategy (Simple ETFs)
31:30 Why They Avoid Complexity in Investing Products
31:45 Fundraising Journey: From Angels to Crowdfunding
33:00 Lessons from Running a Crowdfund
34:10 When Crowdfunding Actually Works
36:00 Mercury’s Acquisition Strategy Explained
38:00 Building an All-in-One Financial Platform
41:00 George’s Founder Journey & Early Exit
42:30 From “Sharky” to Self-Aware Leader
43:30 How Meditation Changed His Leadership Style
45:00 Managing Teams: Autonomy, Mastery, Purpose
47:00 Long-Term Vision for Prospero AI
49:30 Rapid Fire Begins
49:40 Founder He Admires (Jensen Huang)
50:40 Trends That Won’t Last
51:30 What He Changed His Mind About
52:05 Closing Thoughts

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 outcomes
The data behind why strangers can make better co-founders
What actually makes a billion-dollar founding team
Why Andy evaluates the team before the idea when investing
The key ingredients: skill, interest, and timing alignment
Why solo founders rarely build generational companies
How AI is enabling a new wave of high-revenue, small-team businesses
The evolution of venture capital — and what might come next
Andy’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 company
How David thinks about dilution — and why inefficient spending is where founders actually lose equity
The three headcount breaking points every CEO hits and how your role has to change at each one
Why small businesses need owned channels and how marketplaces eating their margin is the defining tension in that market
What clean tech investing looked like during the Vinod Khosla era vs. how David approaches it now
Why solar's cost curve looks nothing like oil's over the last 100 years — and what that means for timing
How David thinks about nuclear's role alongside renewables
What made the Weebly acquisition to Square work when most acquisitions don't
How word of mouth drove 80%+ of Weebly's growth and why that's hard to explain to investors
Why David moved from operating to investing — and what the coach-on-the-sidelines framing means to him

In 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

This week, we're bringing back one of our most loved episodes on Founders in Arms. Ryan Gariépy is the co-founder and former CTO of Clearpath Robotics and Otto Motors, acquired by Rockwell Automation for $600M+ in 2023. He bootstrapped the company for five years with only $300K in funding, reached profitability in 18 months, and spent 14 years building mobile robotics platforms that became the industry standard for research and industrial automation.
What you'll learn:
Why robotics is a systems discipline where progress stacks rather than explodes
How to bootstrap a hardware company to $10M revenue before raising venture capital
Why robotics follows 20-50% sustained growth for decades vs. software's boom-bust cycles
The "promise problem" with humanoid robots and why form factor shapes user expectations
How manufacturing in Canada (not China) became a strategic advantage for Clearpath
Why founders overestimate 2-year progress but underestimate 10-year impact in robotics
The real economics of humanoid robots: $20K cost becomes $80K landed price
How robotics investment differs from software: less competitive, more defensible
Why experience compounds in hardware but expires in software careers Investment criteria for robotics: engineering risk vs. technical risk and go-to-market strategy
In this episode, we cover:
(00:00) Introduction and live event announcement (03:29) Ryan's background: Clearpath Robotics and Otto Motors (04:06) Building two brands under one company (06:29) The 14-year journey: challenges and non-linear growth (07:11) Bootstrapping robotics when "nobody thought you could make money" (08:17) Reaching profitability in 18 months with research customers (10:28) Building robotics platforms for MIT, universities, and research labs (11:03) Manufacturing in Canada vs. outsourcing to Asia (15:05) Reconnecting after 20 years: the Waterloo entrepreneurship connection (16:17) Working at Kiva Systems (now Amazon Robotics) (18:10) Why robotics is more exciting now than ever in history (19:21) Robotics as systems discipline: no single breakthrough technology (21:22) The overhype cycle and realistic expectations (22:14) Software explodes then crashes; robotics compounds for decades (23:36) Why hardware is harder but more mission-driven (25:27) The talent pool advantage: people irrationally love hardware (27:30) Physical AI and real-world impact beyond software optimization (28:07) Humanoid robots: incredible tech, miscalibrated expectations (32:41) The "promise problem": form factors make promises to users (34:35) Consumer robotics examples: Matic cleaning robot (35:59) Asia leading in restaurant and airport robotics deployment (38:37) Training challenges and precursor technologies needed (39:20) China's role in robotics and humanoid development (41:08) Venture capital structures forcing "ridiculous things" in robotics (42:36) Robotics for entertainment vs. utility as consumer use case (43:52) Imad's robotics investments: Embark, Gecko Robotics, vertical AVs (45:23) Why robotics is less competitive than software (47:21) Operational design domain and technology risk assessment (48:19) The AV journey: Waymo, Zoox, and the importance of experience (49:39) Experience compounds in hardware, expires in software (50:31) Rapid fire: biggest mistake, following gut over charisma (51:47) Founder inspiration: Rodney Brooks (52:20) Uncomfortable feedback at Honda co-op job (53:17) Investment criteria: engineering risk, go-to-market, team understanding

Marco Zapacosta is the co-founder and CEO of Thumbtack, the home services marketplace connecting homeowners with local pros for everything from plumbing to renovation. Started three weeks before Lehman Brothers collapsed in 2008, Thumbtack has grown to over $500M in annual run rate across 17 years of building.
What you'll learn:
Why Marco believes Thumbtack is still pre-product market fit at $500M in revenue
How AI is shifting Thumbtack from a search engine to a matchmaker
Why word of mouth is still the biggest competitor to every home services marketplace — and how AI finally evens the score
Why convenience doesn't win when someone's spending $1,000 and entering your home
Marco's take on practitioners vs. projectors — and why he doesn't trust most AI predictions
Why AI agents won't disintermediate high-trust marketplaces
How Thumbtack's operating model evolved from Google to Facebook to their own matrix structure
What's kept Marco going for 17 years — and why he scores zero on neuroticism
Why Marco wants to stay private a little longer before an inevitable IPO
Why AI applied to robotics is overhyped and synthetic biology is massively underrated

In this episode, we cover:
(00:00) AI as substitute vs. complement — the flaw in our collective thinking
(01:00) Introduction to Marco Zapacosta
(02:12) Practitioners vs. projectors on AI
(04:14) Real anxiety about AI job loss — engineers at birthday parties
(07:21) Why Marco doesn't trust Block's layoff messaging
(09:46) How AI is a massive accelerant for Thumbtack
(10:02) Why home services is still pre-product market fit at $500M
(11:02) Word of mouth is Thumbtack's biggest competitor
(12:40) Will AI agents disintermediate marketplaces?
(15:17) Why choice still matters in high-trust purchases
(17:34) Why humans still want to read reviews themselves
(19:15) Thumbtack's origin story — starting 3 weeks before Lehman collapsed
(23:16) What's kept Marco going for 17 years
(24:42) Entrepreneur parents and raising entrepreneurial kids
(30:20) How Marco runs the company — the matrix model explained
(35:25) Four co-founders: how responsibilities divided over time
(37:02) Is Thumbtack going public?
(39:33) The real downsides of being a public company
(45:21) Rapid fire: who inspires Marco, what's overhyped, what's underhyped
(47:12) The hardest part of leadership is self-awareness, not skills
(49:02) Why struggling early builds staying power