Episodes

Ryan Gariepy 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. (If you’re looking for inspiration and lessons from other founders, Founders in Arms is hosting a founders roundtable with Raja...

Emmett Shear is the founder and CEO of Softmax, an alignment research company, and previously co-founded and led Twitch as CEO. He was also a Y Combinator partner and briefly served as interim CEO of OpenAI. What you'll learn: Why AI alignment and AGI are fundamentally the same problem How theory of mind is the critical missing piece in current AI systems Why continuous learning requires self-modeling capabilities The dangerous truth: alignment is a capacity for both great good and great evi...

Immad Akhund and Raj Suri reunite for a one-on-one conversation covering the biggest tech shifts of 2025, from Mercury's public launch of Personal Banking to the quieting of AGI doom discussions. This wide-ranging episode explores why self-driving cars may matter more than AGI, how vibe coding is changing software development, and the strategic decisions founders make when everyone else disagrees. What you'll learn: Why Immad launched Mercury Personal despite investor and team skepticism—and t...

Noah Glass is the founder and CEO of Olo, an enterprise platform for mobile and online ordering that powers digital commerce for 800+ restaurant brands and nearly 90,000 locations. Founded in 2005, Olo went public in 2021 at a $3.5B valuation and was acquired by Thoma Bravo in 2024—a 20-year journey from scrappy startup to category leader. What you'll learn: Why Olo's first 10 years required extreme "pain tolerance" waiting for product-market fit The B2C to B2B pivot that transformed their uni...

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: Why everything built for human web consumption will become irrelevant when agents bec...

Nicholas Rudder is the co-founder and CEO of Sphere, an AI-powered cross-border tax compliance platform that helps businesses navigate international sales tax, VAT, and GST regulations. After pivoting from a failed EdTech marketplace and losing his technical co-founder, Nicholas just raised $21M in Series A funding from Andreessen Horowitz—a remarkable comeback story that includes selling his first five contracts using only a Figma prototype. What you'll learn: How Sphere is becoming the "Deel ...

Sumir Meghani is the founder and CEO of Instawork, a staffing marketplace connecting 9 million hourly workers with businesses that need flexible labor. Starting with just line cooks in San Francisco restaurants, Instawork now serves warehouses, stadiums, hotels, and hospitality businesses across the country, creating what Sumir calls "employment at the touch of a button." What you'll learn: Why starting "boring and narrow" (one city, one job type) is the key to marketplace success How Instawor...

We're reposting this episode following major news: Pebble officially relaunched its companion app on iOS and Android, bringing exciting and new apps and watch faces to both new Pebble devices and original watches. The Pebble 2 Duo has begun shipping to customers who preordered earlier this year. Eric Migicovsky is the Founder of Core Devices, and the original founder of Pebble, the pioneering smartwatch that raised $10 million on Kickstarter before being acquired. Eric has launched Core Devices...

Iqram Magdon-Ismail is the co-founder of Venmo and current founder of Jelly, a video-first social app. After building Venmo from a text-message prototype to a verb used by millions (ultimately acquired by PayPal via Braintree), Iqram is now tackling what he sees as social media's biggest problem: it became all ads, influencers, and flexing instead of genuine connection. What you'll learn: How Venmo started from forgetting a wallet at dinner and evolved into a cultural phenomenon The near-shut...

In this one-on-one episode, Immad and Raj catch up on what's happening in tech, and what founders should actually be paying attention to right now. Fresh from DC, Immad shares a surprising disconnect he observed about AI regulation and market sentiment. The conversation moves through whether we're in another bubble, the startup metrics that are being gamed again, and the infrastructure realities that might change everyone's timelines. They also get into the fundamentals that separate sustainab...

Dan Wang is a research fellow at Stanford's Hoover Institute and author of "Breakneck: China's Quest to Engineer the Future." After spending six years living in Hong Kong, Beijing, and Shanghai (2017-2023), Dan witnessed China's technology growth, the US-China trade and tech war, Xi Jinping's increasing authoritarianism, and three years of zero-COVID pandemic controls firsthand. What you'll learn: Dan's framework of "engineering societies vs lawyerly societies" for understanding the US-China co...

Iñaki Berenguer is a serial entrepreneur with three successful exits: Pixable (sold to Singtel), Clink (sold to Thinking Phones), and CoverWallet (sold to Aon for $300M). He's now a partner at Flive Ventures, a $100M fund investing at the intersection of AI and healthcare, and president and co-founder of Ipronics, an AI infrastructure company for data centers. What you'll learn: How Iñaki built CoverWallet from 0 to $100M in premium revenue and 400 employees in just 4 years Why he'd rebuild hi...

Andrew D'Souza is the founder and CEO of Boardy AI, an AI "super connector" that helps founders, investors, and operators make high-value introductions through voice conversations. Previously, Andrew co-founded and scaled Clearco (formerly ClearBank) from a YC Fellowship company to over $100M in revenue and 600 employees across 11 countries before stepping down as CEO to pursue AI innovation. What you'll learn: How Andrew pivoted Clearco through three different markets before finding product-m...

How do you build a sustainable AI business when investors are throwing money at anything with "AI" in the pitch deck? We're bringing back one of our best episodes featuring Jesse Zhang (Decagon AI CEO). This is a strategic conversation that centers on the business challenges of building an enterprise AI company that can sustain beyond the current hype cycle. Jesse reveals how AI moves beyond being a mere chatbot to become a "system of intelligence" that encodes complex business logic, creating...

David Gu is the co-founder and CEO of Recall.ai, building conversation recording infrastructure that powers over 1,000 AI companies. Fresh off announcing a $38 million Series B led by Bessemer, David shares the journey from a Winter 2020 Y Combinator call recording tool to becoming the backbone of AI conversation intelligence. What you'll learn: How David pivoted from application to infrastructure after spending 80% of engineering time on recording problems Why the social shift toward recordi...

Bill Clerico is the founder and former CEO of WePay, which he sold to JPMorgan Chase for $400 million, and is now founding managing partner of Convective Capital, investing in wildfire risk management and physical resilience technologies. Starting WePay during the 2008 financial crisis when VCs said "no one makes money in payments except PayPal," Bill built one of the pioneering fintech companies alongside Stripe and Square. What you'll learn: Why VCs avoiding entire sectors often signals the ...

Joris Poort is the CEO of Rescale, a digital engineering platform that provides supercomputing capabilities for engineers and scientists designing rockets, drugs, and computer chips. Starting from Y Combinator in 2012, Rescale has grown over 14 years to serve major aerospace and life sciences companies with over 200 employees and a platform that combines high-performance computing with AI physics capabilities. What you'll learn: Why "Default Alive" means cash flow positive, not just having runw...

Ian Tien is the co-founder and CEO of Mattermost, an open-source collaboration platform that has evolved from a Slack alternative to essential infrastructure for government and defense organizations worldwide. Starting from a failed HTML5 gaming platform at Y Combinator, Mattermost now serves over 4,000 contributors, employs 120 people, and operates profitably while powering sovereign collaboration for national security agencies. What you'll learn: How Mattermost pivoted from gaming to defense ...

Arvind Jain is the founder and CEO of Glean, building enterprise AI that connects to all internal company data, and co-founder of Rubrik, which recently went public. Starting as an enterprise search company in 2019, Glean has evolved into what Arvind calls "a more powerful version of ChatGPT inside your company," now approaching 1,000 employees and serving the world's most iconic companies. What you'll learn: How Glean evolved from search to conversational AI without pivoting by riding AI mode...

We’re bringing you a rerun of one of our most well-received episodes, featuring the incredible insights from serial entrepreneur Hiten Shah. What happens when the ultimate startup veteran joins a 3,000-person company after 20 years of founding his own? In this candid conversation, Mercury CEO Immad Akhund and serial founder Raj Suri sit down with Hiten Shah (Crazy Egg, KISSmetrics, Nira—acquired by Dropbox) for an honest exploration of founder identity, business fundamentals, and the reality o...

This week, we're re-airing our conversation with Reddit CEO Steve Huffman about building one of the internet's most essential platforms over 20 years. Steve Huffman is the co-founder and CEO of Reddit, one of the internet's most essential platforms with 100 million daily active users and a $20 billion public market valuation. Over 20 years, Steve has guided Reddit through multiple existential challenges, from early acquisition to content moderation crises to competing with AI-generated content....

Bringing back one of the most loved episodes of Founders in Arms! In this episode, Immad and Raj welcome Silicon Valley legend Paul Buchheit. As the creator of Gmail, an early Google pioneer, and a Y Combinator partner, Paul shares his unique perspectives on the rapidly evolving AI landscape and its implications for startups and society. The conversation covers the current state of large language models and their potential future developments, opportunities for new social apps in the age of A...

Trip Adler is the founder and CEO of Created by Humans, a new marketplace helping rights holders license their works for AI training, reference, and transformation. Before this, he spent 17 years building Scribd, pioneering book subscriptions and navigating complex copyright challenges. Now, he’s tackling one of the most urgent questions in AI: how to fairly compensate creators when AI models train on human work. What you'll learn: Why the future of AI and human creativity depends on solving c...

Ryan Westerdahl is the founder and CEO of Turion Space, designing and building satellites for resilient space infrastructure with a focus on space domain awareness and orbital debris removal. After nine years at SpaceX working on failure analysis across multiple departments, Ryan founded Turion in 2021 with the ultimate goal of asteroid mining. The company now operates 120 people across hardware and software platforms, with two operational satellites in orbit and over $10 million in revenue. Wh...