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:

1. Why choosing a co-founder from your existing network can lead to weaker outcomes
2. The data behind why strangers can make better co-founders
3. What actually makes a billion-dollar founding team
4. Why Andy evaluates the team before the idea when investing
5. The key ingredients: skill, interest, and timing alignment
6. Why solo founders rarely build generational companies
7. How AI is enabling a new wave of high-revenue, small-team businesses
8. The evolution of venture capital — and what might come next
9. 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:

1. Why Weebly stayed cash flow positive from early 2009 and what that meant for how they built the company
2. How David thinks about dilution — and why inefficient spending is where founders actually lose equity
3. The three headcount breaking points every CEO hits and how your role has to change at each one
4. Why small businesses need owned channels and how marketplaces eating their margin is the defining tension in that market
5. What clean tech investing looked like during the Vinod Khosla era vs. how David approaches it now
6. Why solar's cost curve looks nothing like oil's over the last 100 years — and what that means for timing
7. How David thinks about nuclear's role alongside renewables
8. What made the Weebly acquisition to Square work when most acquisitions don't
9. How word of mouth drove 80%+ of Weebly's growth and why that's hard to explain to investors
10. 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:

1. Why Marco believes Thumbtack is still pre-product market fit at $500M in revenue
2. How AI is shifting Thumbtack from a search engine to a matchmaker
3. Why word of mouth is still the biggest competitor to every home services marketplace — and how AI finally evens the score
4. Why convenience doesn't win when someone's spending $1,000 and entering your home
5. Marco's take on practitioners vs. projectors — and why he doesn't trust most AI predictions
6. Why AI agents won't disintermediate high-trust marketplaces
7. How Thumbtack's operating model evolved from Google to Facebook to their own matrix structure
8. What's kept Marco going for 17 years — and why he scores zero on neuroticism
9. Why Marco wants to stay private a little longer before an inevitable IPO
10. 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

Noah Smith is a writer and Substack blogger behind Noahpinion, known for his contrarian, data-grounded takes on economics, technology, and geopolitics.

What you'll learn:

1. Why the viral Citrini "2028 Global Intelligence Crisis" post moved markets — and whether it should have
2. The psychology behind why "AI causes 2008" scared Wall Street more than killer robots
3. Why Noah thinks an AI-driven financial crisis is possible but unlikely
4. How a productivity boom could paradoxically trigger a mild recession through "sticky prices"
5. Why AI-enabled bioterrorism — not economic disruption — is Noah's biggest fear
6. What Block's 4,000-person layoff and Mercury's hiring shifts reveal about AI's real impact on jobs
7. Why software job losses in 2023-24 may have been driven by uncertainty, not AI capability
8. Noah's take on deflation, GDP growth, and where inflation goes from here
9. Why intellectual humility has been Noah's biggest edge as a forecaster
10. The "dinosaur and the meteor" theory — why we're worrying about the economy while a much bigger threat flies overhead

In this episode, we cover:

(00:00) The meteor meme — AI's real threat vs. the economy

(01:07) Introduction to Noah Smith

(02:14) What the Citrini post actually argued

(04:30) Why markets missed Covid — and what that tells us about AI

(06:17) Why Citrini moved markets: the power of pattern matching to 2008

(07:51) Breaking down Citrini's financial crisis domino theory

(08:38) Noah's verdict: possible but unlikely

(11:04) Block lays off 4,000 — how does AI-driven unemployment play out macro?

(17:42) How a productivity boom could cause a recession: sticky prices explained

(19:46) Noah's real AI fear: vibe-coded bioweapons

(24:55) Has bioterror surpassed China-Taiwan as Noah's top worry?

(25:10) The economy today: inflation, deflation, and GDP

(28:44) What Mercury's hiring strategy reveals about AI's effect on headcount

(31:32) Why software job losses in 2023-24 may have been forward-looking uncertainty

(34:38) The threat to blue collar jobs — are truck drivers next?

(35:52) Why intellectual humility is Noah's competitive edge

(39:26) The meteor meme closing: we created zombie gods for a 2.7% productivity boost

We're bringing back one of our most loved episode on Founders in Arms.

Parag Agrawal is the co-founder and CEO of Parallel, building infrastructure for the agentic web. Previously CEO of Twitter, Parag now leads a company architecting how AI agents will interact with the open web at orders of magnitude beyond current human scale. Two years after founding in stealth mode, Parallel recently announced a $100M Series B co-led by Kleiner Perkins and Index Ventures.

What you'll learn:

1. Why everything built for human web consumption will become irrelevant when agents become the primary users
2. How Parallel's APIs enable agents to search, fetch, and monitor the web with unprecedented scale and speed
3. The evolution from simple tool calls to autonomous sub-agents with real decision-making capability
4. Why the web must transition from "pull" (searching on demand) to "push" (alerting when conditions are met)
5. The new business models needed to compensate content creators in an agent-driven web
6. Parag's counterintuitive approach to fundraising: why VC rejections don't sting but customer rejections do
7. The rational game VCs play that founders misinterpret as genuine enthusiasm
8. Why Parag believes we're not in an AI bubble—but an overreaction is coming (and it'll be faster than dot-com)
9. How Parallel built quietly for a year before product-market fit arrived with the agent explosion
10. The operational philosophy of extreme in-person collaboration that shaped Parallel's early culture

In this episode, we cover:

(00:00) Introduction and Parallel's mission

(01:02) What Parallel's APIs enable for AI agents

(02:43) Practical examples: coding agents, sales automation, research

(04:57) The conviction bet on agents before the market existed

(10:54) New business models for content in the agentic web

(20:22) The $100M Series B fundraise and going public

(23:03) Why Parallel built in stealth with carefully chosen early customers

(24:55) Current scale and product offerings

(30:42) The evolution from tools to sub-agents to push-based web

(33:13) Are we in an AI bubble? Parag's nuanced perspective

(36:34) The mental models behind fundraising vs customer rejections

(38:37) Why VC enthusiasm is rational strategy, not signal

(45:37) Biggest career mistake: delaying Twitter's algorithmic timeline

(48:28) The compounding cost of six-month delays

(50:09) Finding inspiration in "re-founders" like Satya Nadella

(51:54) The most rewarding part: watching customers do unexpected things

(52:43) In-person culture and the transition to remote-friendly

Vishwas Prabhakara is the co-founder and CEO of Honey Homes, a subscription home maintenance service that's reimagining how Americans care for their homes. After spending four years at Yelp running the restaurant business, Vishwas saw firsthand why marketplaces fail for skilled home services—and built a contrarian solution. Now operating across San Francisco, LA, Chicago, Dallas, and Austin with 3,000+ members, Honey Homes creates quality jobs for skilled workers while delivering consistent, reliable home maintenance to homeowners.

What you'll learn:

1. Why the marketplace model fundamentally fails for skilled labor and home services
2. The counterintuitive insight behind every successful consumer business (the Airbnb lesson)
3. How Vishwas discovered workers were shocked that "nobody's yelled at me yet" after joining Honey Homes
4. Why solving both sides of the market—customer experience AND worker quality of life—is essential
5. The role of AI in leveling up service workers and automating operations without replacing humans
6. Why early compromises on hiring and standards compound into major problems later
7. The distribution challenge: getting consumers to prioritize chronic home maintenance needs
8. How altruism, not just incentives, drives consumer referrals and growth
9. Why companies like Yelp, Peloton, and Lyft deserve more respect for building culturally relevant businesses
10. The mental model shift required to sell subscription home services vs. one-time fixes

In this episode, we cover:

(00:00) Introduction and the respect successful companies deserve

(01:12) YC batch memories and feeling "late" to tech trends

(03:05) The genesis of Honey Homes and why Immad and Raj invested

(04:50) Growing up with a handy dad and discovering the home services gap

(06:30) The counterintuitive consumer insight behind Honey Homes

(07:03) "Nobody's yelled at me yet"—the worker experience problem

(08:11) Why marketplaces don't work for skilled home services

(09:48) Hiring only 1% of handyman applicants

(14:07) Building trust through consistent quality and W2 employment

(19:31) How altruism drives consumer referrals, not just incentives

(21:51) Getting AI-pilled at Vinod Khosla's CEO retreat

(23:01) Using AI to level up workers and automate operations

(27:54) Overcoming the mental model barrier for subscription home services

(30:07) The vision compromise lesson: don't settle on quality early

(31:44) The critical importance of distribution for consumer businesses

(32:26) Why partnerships aren't the answer (yet) for Honey Homes

(38:41) Defending Yelp, Peloton, and Lyft against Silicon Valley discourse

(42:18) Unit economics challenges in services businesses

(47:10) Role models: Jeremy Stoppelman and Ramit Sethi

(48:08) Hope that divisiveness is a passing trend

(49:35) The daily challenge of building before the world sees it

(51:04) Getting feedback about being "unpredictable" and staying in your head

(52:33) Bringing people along for the journey in your mind

What does it take to build a company in a category where everyone says the idea is dead? In this special live recording from Mercury's San Francisco office, Immad Akhund and Raj Suri sit down with Max Mullen, co-founder and former Chief Product Officer at Instacart, for an honest conversation about the founder journey.

Max shares how Instacart started in 2012 when there was no gig economy, no Uber X, and investors repeatedly told them grocery delivery was a dead idea after Webvan's failure. The conversation explores the controversial early days of building Instacart, why Max believes founder pain tolerance is the biggest moat, and the critical importance of market timing even when you're executing well.

Max opens up about the challenges of being a technical co-founder without deep technical skills, navigating co-founder dynamics, and the reality that many startup outcomes are heavily influenced by timing and luck. The discussion shifts to AI's transformative potential, with Max offering a compelling framework: software engineers are experiencing "the tip of the spear" of AI capabilities today, and this same 10x productivity leap will soon apply to lawyers, doctors, accountants, and every other profession.

He explores what AI-native companies will look like and why the next wave of startups will be built around professionals orchestrating fleets of agents. This episode offers essential insights for founders building in challenging markets, navigating co-founder relationships, timing market opportunities, and understanding where AI is creating the biggest opportunities for new companies.

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:

1. Why SaaS companies are struggling and what survives
2. The real reason enterprises buy software (risk offloading, not features)
3. AI agents in practice: what works, what doesn't
4. Google's strategic win with Apple's Gemini integration
5. How to pitch VCs when expectations are 5x higher than before
6. Why crazy promises and long timelines still attract capital
7. The shift to leaner startups and API-first business models

Mehul Nariyawala is the co-founder and President of Matic Robotics, a home robotics company building what he calls “robotics 2.0” — intelligent, vision-first robots designed to actually work in real homes. After early careers at Nest and a prior acquisition by Google, Mehul and his team spent seven years building Matic, challenging the assumptions behind robot vacuums, consumer hardware, and how robotics companies should scale.

In this conversation, Mehul breaks down why robotics is far harder than software, why most home robots quietly fail, and how Matic approached everything differently — from vision-only robotics and in-house manufacturing to avoiding subscriptions, ads, and premature market creation.

What you’ll learn:

• Why robotics is “100× harder than software” — and where most teams underestimate the work
• The difference between automation and true intelligence in home robots
• Why negative-NPS categories can hide massive opportunities
• How Matic beat entrenched incumbents like Roomba by fixing fundamentals, not adding features
• Why vision-only robotics was a risky but necessary bet
• The real reason humanoid robots are still far from consumer-ready
• Lessons from Nest on why some hardware categories stay defensible for decades
• Why creating a new market can be fatal for hardware startups
• How Matic built robots in-house in California instead of outsourcing manufacturing
• The tradeoffs between subscriptions, ownership, and consumer trust
• Why great hardware products must earn word-of-mouth before growth

In this episode, we cover:

(00:00) Introduction to Mehul Naryawala and Matic Robotics

(01:10) Why robotics is dramatically harder than software

(03:00) The failure modes of early robot vacuums

(05:10) Identifying opportunity in negative-NPS markets

(07:45) Automation vs. intelligence in consumer robotics

(10:15) Why vision-only robotics was a foundational bet

(14:00) Lessons from Nest on defensible hardware categories

(17:30) Why Matic avoided creating a new market

(20:45) In-house manufacturing and vertical integration

(24:30) Scaling hardware without inventory risk

(28:10) The long road from demo to product

(32:00) Why humanoid robots are still overhyped

(36:20) Word-of-mouth, product-led growth, and brand trust

(40:15) Subscription fatigue and consumer psychology

(44:30) The future of home robotics and where Matic goes next

Jack Zhang is the co-founder and CEO of Airwallex, a global payments and financial platform valued at $5.5 billion. Founded in Melbourne, Airwallex processes billions in cross-border transactions and serves businesses expanding internationally. Jack shares his journey from starting the company to competing with giants like Stripe, navigating the complexities of global payments infrastructure, and building across multiple regulated markets.

What you'll learn:

1. Why cross-border payments remain broken despite decades of fintech innovation
2. How Airwallex competes against Stripe and other established payment platforms
3. The challenge of building financial infrastructure across multiple countries and regulations
4. Jack's perspective on fair competition versus FUD (fear, uncertainty, doubt) tactics in business
5. Why Airwallex is deploying $1 billion in the US market over the next three years
6. The reality of being a foreign founder building in America during geopolitical tensions
7. How payment infrastructure for global businesses differs from consumer fintech
8. The trade-offs between growth velocity and sustainable business building
9. Jack's philosophy on money, success, and what matters after achieving wealth at 30
10. Why he chose to stay in Melbourne instead of relocating to San Francisco

In this episode, we cover:

(00:00) Introduction to Jack Zhang and Airwallex

(02:34) Early days of Airwallex and the founding story

(05:12) The problem with cross-border payments

(08:45) Competing with Stripe and other payment platforms

(12:18) Building in regulated markets and compliance challenges

(16:23) FUD (fear, uncertainty, doubt) tactics in business competition

(19:13) Raj's experience with FUD at Lyft vs Uber

(22:47) Navigating geopolitical tensions as a Chinese-Australian founder

(25:36) The $1 billion US market investment commitment

(27:41) Product philosophy and fair competition

(31:15) Going upmarket vs staying with SMBs

(35:22) Life choices: Melbourne vs San Francisco

(37:49) Perspective on wealth - "not about the money"

(42:18) The future of payments infrastructure

(45:30) Advice for founders building in competitive markets