Founders in Arms

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 to continue building the smartwatch platform he believes in, complete with Google's newly open-sourced Pebble operating system.What you'll learn:1. The Kickstarter phenomenon: How Pebble became one of the first massive Kickstarter successes, raising $600K in the first day with a $100K goal2. Hardware's inventory trap: Why missing revenue projections by 20% ($80M vs $100M target) created a $20M inventory crisis that nearly sank Pebble3. The sustainable hardware model: Eric's new approach of targeting profitability at 5,000 units and eliminating inventory risk through pre-orders4. Inventor vs. founder mindset: The difference between building products you love versus building scalable companies5. Fighting Big Tech: How Eric's Beeper Mini challenged Apple's iMessage monopoly and led to DOJ antitrust action6. Getting software from Google: The surprising story of how Google open-sourced Pebble's operating system to enable Core Devices7. Hardware manufacturing today: Why building smartwatches is easier now than in 2011, and what's still challenging8. The artisanal hardware movement: Building premium, limited-run products for passionate niche audiences9. Regulatory battles: Apple's API restrictions and how they limit third-party smartwatch functionality10. AI integration: Adding ChatGPT and voice capabilities to modern smartwatchesIn this episode, we cover:(00:00) Introduction and reconnecting with Eric(01:18) The Core Devices relaunch and getting Pebble IP from Google(02:33) Eric and Raj's Waterloo connection and early entrepreneurship(04:48) From Pebble's precursor to YC and the smartwatch vision(09:30) The legendary Kickstarter launch day and calling Raj at 2am(14:00) Five years of overnight success and authentic marketing(16:07) Inventor vs. founder mindset and product obsession(19:21) The 2015 inventory crisis that changed everything(27:20) Eric's new sustainable hardware model with Core Devices(32:00) Using existing Pebble cases and Google's open-source software(36:58) The artisanal approach: 3 people, no VCs, limited production runs(41:14) AI integration and ChatGPT on the wrist(49:36) Secondary markets and public company trading restrictions

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 phenomenonThe near-shutdown moments when Wells Fargo threatened to close their accountWhy Venmo raised only $3.4M total before the Braintree acquisitionThe strategy behind keeping Venmo invite-only for five yearsHow the team's close friendship shaped Venmo's personality as a productWhy Iqram believes AI made startups polished but soullessThe shift from building for purpose (helping musicians) to building for metrics (ARR, funding)What it's like working at PayPal after selling your startupHow Jelly uses crypto infrastructure to enable global money movement through videoWhy immigrant founders bring a different hunger and work ethic to building companiesIn this episode, we cover:(00:00) Introduction to Iqram and his founder journey(00:49) The origin story of Venmo - forgetting a wallet(03:08) Building on Google Voice and eating credit card fees(08:40) The near-death moment with Wells Fargo(12:01) How the Braintree acquisition saved Venmo(16:56) Working with Bryan Johnson at Braintree(18:57) The regret of not having more equity in Venmo's success(21:06) What makes Venmo feel different than other payment apps(22:16) Why modern startups lost their personality and purpose(26:00) Life at PayPal after the acquisition(27:38) Consumer vs B2B founder-product fit(30:23) Social media became a nightmare of ads and flexing(32:20) Demo and vision for Jelly(39:06) Using crypto and meme coins in social apps(41:15) Why invite-only launches create quality users(42:38) Rapid fire questions on inspiration and mistakes(45:28) What it means to be an immigrant entrepreneur

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 sustainable companies from hype-driven ones: why retention matters more than growth, what to do after raising at a high valuation, and the frameworks they actually use to make spending decisions.Plus updates on what they're building at Mercury, Tribe, and Lima—and the lessons they're learning along the way.A candid founder-to-founder conversation about navigating uncertainty and building for the long term.

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 competitionHow China deliberately promoted engineers to power—by 2002, all nine Politburo Standing Committee members had engineering degreesWhy the one-child policy and zero-COVID demonstrate the dangers of literal-minded engineering applied to societyHow America transformed from building the transcontinental railroad and Apollo missions to being unable to fix its subway systemsWhy lawyers took over American governance in the 1960s and created a self-reinforcing systemThe stark reality: China builds 500 gigawatts of solar capacity annually vs America's 50, and has 30 nuclear plants under construction vs zeroWhy China's electricity advantage could determine who wins the AI race—not just better modelsHow American AI leadership is threatened by power constraints and Chinese researchers potentially returning homeWhy robotics applications of AI matter more than reasoning models for geopolitical competitionThe dual reality of America: trillion-dollar tech companies exist alongside broken infrastructure that only works for the wealthyDan's writing process: traveling, eating (twice), reading novels and history, and being deliberately provocativeThe future of US-China competition in semiconductors, aviation, manufacturing, and whether America's technological lead is sustainableIn this episode, we cover:(00:00) Introduction and Dan's AI/electricity thesis(01:15) Dan's journey from San Francisco tech to China analyst(03:40) Engineering society vs lawyerly society framework(04:21) Why engineers running governments can be dangerous(05:46) The one-child policy: designed by a missile scientist(06:56) China's path from Mao to engineering-focused leadership(09:51) America's transformation from builder to regulator (1960s shift)(11:08) Can the pendulum swing back? Housing, transit, and infrastructure failures(13:12) The self-reinforcing nature of lawyerly societies(14:12) Yale Law ambition vs Stanford engineering ambition(16:13) Is there bipartisan consensus on building?(17:41) Why left and right can't agree on solutions(19:32) China's engineering design flaws and authoritarian feedback loops(22:19) US technological advantages: semiconductors, AI, aviation(23:07) The electricity bottleneck: China's massive power advantage(24:31) If AI is everything, what should America do?(26:29) Why Dan doesn't buy the "AI is everything" premise(27:27) Robotics as the real AI battleground(29:35) Silicon Valley codes, China builds power plants(30:37) Anti-AI populism emerging on left and right(33:41) Dan's meta process: philosophy, eating, traveling, reading, being provocative(37:20) China's rural infrastructure and redistribution through building(40:39) Peter Thiel question: acknowledging China's dual reality(44:54) America's core tension: works great for the rich, broken for everyone else(46:35) Will China get stuck in the 2010s like Japan in the 1980s?

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 yearsWhy he'd rebuild his 250-person company with only 10 people in the AI eraThe hidden time cost of scaling teams: 40% of CEO time spent on HR, hiring, and one-on-onesHow strategic partnerships with potential acquirers create acquisition optionalityWhy investment bankers matter: the difference between 3-month and 8-month due diligence timelinesThe critical mistake of taking common stock vs. preferred in acquisition dealsWhy "paranoid optimist" is the ideal founder mindsetThe lifestyle reality check: VC work vs. founder intensity and what actually counts as "high pressure"Reference check strategies that reveal integrity under pressureHow luck and timing determine exits more than founders want to admitIn this episode, we cover:(00:51) Iñaki's journey: three companies, three exits across different industries(03:21) Why Pixable's "always on" consumer product was harder than enterprise(09:04) The decision to sell CoverWallet despite investor pressure to keep building(12:20) Product-market fit doesn't exist in AI: markets change faster than products(19:43) How Iñaki would rebuild differently: from 250 employees to AI agents(22:32) The real time cost of hiring: 100 employees = 1,000 interviews(27:16) M&A lessons: why time kills deals and investment bankers matter(29:03) Building optionality through strategic partnerships with potential acquirers(32:37) The fulfillment of building vs. investing: team wins and external validation(36:23) Why founders struggle to celebrate wins that took years to achieve(40:25) The "paranoid optimist" mindset: assuming someone is always working harder(42:14) AI in healthcare: the most underhyped opportunity(45:20) Comparing entrepreneurial cultures: Silicon Valley vs. New York vs. Europe(46:16) The biggest mistake: not doing enough reference checks on people(48:44) What drives founders: proving doubters wrong, not money

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-market fit with e-commerce financingWhy customers who "want to be found" create fundamentally easier go-to-market strategiesThe psychology behind why financial incentives destroy natural networking behaviors and trustHow the best companies now generate inbound investor demand instead of running traditional fundraising processesWhy Andrew learned to trust founder intuition even when he couldn't articulate it to stakeholdersThe technical and business model evolution from merchant cash advances to AI-powered networkingHow Boardy uses voice AI to create more human-like relationship building at scaleStrategic insights on building in regulated industries like financial servicesThe transition from scaling a fintech business to creating AI characters with their own objectivesWhy VCs don't actually remember your previous pitches and how to leverage that realityIn this episode, we cover:(00:00) Introduction and Andrew's journey from Waterloo to YC(02:32) Clearco's evolution from Uber driver financing to e-commerce(04:27) The pivotal board meeting and Series A pivot decision(05:25) Finding product-market fit with customers who "want to be found"(09:35) Scaling Clearco to $100M+ revenue and 600 employees(11:08) The COVID boom and building Clear Angel with GPT-3(13:31) Andrew's decision to step down as CEO(15:58) Introduction to Boardy AI and the AI super connector concept(18:43) Live demonstration of Boardy's voice capabilities(26:33) Business model and the "economy of Boardy" vision(29:09) Why financial incentives destroy network effects(33:36) Fundraising evolution from process-driven to inbound demand(37:13) The reality of investor relationships and memory(43:00) Rapid fire: biggest mistakes, inspiration, and founder psychology(47:29) The creative expression of building AI characters

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 moats for companies that implement it effectively. The conversation also explores the realities of implementation, adoption, and enterprise sales strategies that actually work.Technology founders, customer experience leaders, and investors will find this episode particularly illuminating as it bridges the gap between AI hype and practical implementation. Whether you're evaluating customer service AI, selling enterprise technology, or navigating fundraising, this conversation provides the strategic context and tactical insights needed to make better decisions.

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 problemsWhy the social shift toward recording acceptance created a massive infrastructure opportunityThe systematic approach David used to learn enterprise sales with zero experienceHow Recall's desktop recording SDK eliminates the need for bots in meetingsWhy Series B fundraising still requires a 100x growth vision even at scaleThe framework David uses to validate new products and channels before investing timeHow Amanda Gu built 45,000 LinkedIn followers and turned social media into a lead generation engineWhy David records and reviews every sales pitch to improve his closing rateThe mental shift from seeking external validation to embracing continuous failureHow the conversation data revolution will transform every B2B software applicationIn this episode, we cover:(00:00) Introduction and David's Y Combinator background(01:30) Announcing Recall.ai's $38M Series B funding round(03:18) The pivot from call recording app to infrastructure platform(09:42) Why recording infrastructure became their nightmare and salvation(15:36) Learning enterprise sales as a technical founder(22:13) Amanda's LinkedIn growth and social media lead generation(28:26) Systematic approach to testing new products and channels(34:52) Why Series B still requires 100x vision and growth story(42:17) The social transformation that made recording acceptable(48:23) Working seven days a week for three years in the early days(53:05) The framework for embracing failure as a learning tool

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 biggest opportunitiesThe unconventional partnership strategy that led to WePay's $400M JPMorgan acquisitionHow to position strategic partnerships as pathways to acquisition rather than just revenueWhy WePay's delayed pivot from consumer to developer APIs cost them market leadershipThe specific tactics for getting enterprise buyers excited about acquisition vs. partnershipsHow to navigate the early fintech landscape without established banking infrastructureWhy timing strategic decisions matters more than perfecting the original planThe 12-18 month timeline required for enterprise acquisition conversationsHow crisis-driven industries create first-time openings for technology adoptionBill's contrarian thesis on investing in utilities, insurance, and government sectorsIn this episode, we cover:(00:00) Introduction and Bill's journey from investment banking to entrepreneurship(08:13) Starting WePay during the 2008 financial crisis in Boston(12:00) Getting into Y Combinator and the early pivot struggles(17:37) The acquisition strategy and JPMorgan partnership approach(24:38) Lessons on founder burnout and sustainable company building(36:19) Convective Capital's thesis on physical risk management(42:38) Building an insurance company for high-risk California properties(46:35) The future of wildfire risk and climate resilience investing

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 runway or theoretical profitabilityHow to avoid false trade-offs by asking "why not both?" instead of accepting either/or decisionsWhy the biggest startup mistakes are always people, especially bad executive hiresThe hidden advantages of grinding through difficult early years versus overnight successHow to maintain frugal company culture while scaling from 4 to 200+ employeesStrategic approaches to long-term R&D investments, including AI physics and Department of Defense contractsThe difference between executives who built systems versus those who just ran themWhy promoting internal talent often works better than external executive hiresHow to structure resource allocation decisions to force proper prioritizationThe psychology of founder endurance and why some businesses are intentionally harder to buildIn this episode, we cover:(00:00) Introduction to Joris Poort and Rescale(01:04) Meeting Raj at Paul Graham's place in England(04:36) What Rescale does: supercomputing platform for engineering(08:02) How modern AI impacts scientific computing and physics(12:31) Building for 15 years: the ups and downs of long-term company building(14:20) The moment of becoming "Default Alive" and what it really means(16:49) VCs versus founders on spending and growth philosophy(22:03) Implementing frugal culture and budget discipline at scale(26:56) The challenge of promoting internal talent to executive roles(32:28) Interviewing every hire up to 200 people and building relationships(34:30) Rapid fire: riskiest bets, biggest mistakes, and hard-won lessons(42:31) AI investments, Department of Defense contracts, and strategic moats(48:45) Why the hardest path often creates the strongest business

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 tech through bottom-up adoptionThe concept of "sovereign collaboration" and why governments need independent AI systemsIan's framework for hiring executives with "scar tissue" from diverse experiencesWhy he regrets spending $270,000 on internal swag after taking VC moneyThe unique language and procurement challenges of selling to government customersHow open source enables PLG motion in highly secure environmentsThe difference between "butts and seats" contracting vs. commercial off-the-shelf solutionsWhy most successful founders are in their 30s and 40s, not college dropoutsIan's "daddy daughter days" approach to work-life balance as a CEOThe emerging landscape of sovereign AI and national security technologyIn this episode, we cover:(00:00) Introduction and Ian's Tools for Tech Leaders podcast(04:05) Mattermost's evolution from Slack alternative to sovereign collaboration(08:09) Bottom-up adoption in national security environments(14:23) Learning to sell to government customers and navigate defense acronyms(24:49) Executive hiring philosophy and building long-term relationships(30:47) The sovereign AI landscape and government investment trends(38:53) Defense tech opportunities and getting started in the space(42:57) Palantir's business model and government contracting dynamics(51:18) Rapid fire: Walt Disney as tech founder inspiration and personal lessons

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 model capabilitiesWhy making it easy for customers to leave can be a competitive advantage in enterprise salesThe challenges of competing against every major software company building similar productsHow to recruit from FAANG companies when you can't match their compensationThe difference between building for established markets vs. creating new product categoriesWhy enterprise buyers are tired of AI overpromising and prefer honest positioningHow to stay close to product development while scaling to 1,000 employeesThe transition from Google engineer to startup co-founder and the skills you have to relearnWhy customer success and shared roadmaps are critical for complex AI implementationsThe decision framework for staying independent vs. acquisition when building at scaleIn this episode, we cover:(00:00) Introduction to Arvind Jain and his journey from Rubrik to Glean(01:27) Lessons learned building two different types of enterprise companies(03:09) How Glean works as enterprise search and AI assistant(06:00) The natural evolution from search to conversational AI(08:00) Navigating the AI hype cycle and competitive landscape(11:04) Competition strategy and staying ahead of major software companies(16:40) Honest positioning vs. overpromising in AI sales(20:01) Building enterprise reputation and customer relationships(24:41) Motivation for continuing to build after previous success(26:56) Staying close to product at scale and avoiding bottlenecks(31:08) Using Glean internally and rapid iteration cycles(32:18) The decision to stay independent vs. acquisition(37:24) Transition from Google to startup founder(43:45) Rapid fire questions and leadership lessons(48:31) Uncomfortable feedback about constraining team speed

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 of life after exit.Hiten brings a unique perspective as someone who's built both venture-backed and self-funded companies, including Crazy Egg, which has been running profitably for over 20 years. The discussion covers his contrarian takes on fundraising strategy, why he believes "there's no better hack to product market fit than someone else's product market fit," and the surprising challenges of transitioning from founder to employee.The conversation explores practical frameworks for choosing customers, the hidden truths about venture-backed versus bootstrapped companies, and why Hiten's official title at Dropbox is "Chief Troublemaker." Whether you're building your first startup or considering an exit, you'll gain insights from three founders who challenge conventional wisdom while sharing hard-won lessons from decades of company building.This episode offers essential lessons for entrepreneurs at any stage, covering everything from the psychology of startup building to the practical realities of product-market fit, customer development, and maintaining founder DNA within larger organizations.

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.What you'll learn:- How Reddit achieved product-market fit in just 2 months and the early signs that indicated massive potential- Why Steve sold Reddit for $10 million after 18 months and what he learned during his 9-year absence- The existential crisis that brought him back as CEO in 2015 and how he rebuilt the platform- Reddit's evolution through three distinct eras: link aggregator, intentionally not social media, and authentic human content in an AI world- The strategic decision in 2008 to let users create subreddits and how it transformed the platform- Building content moderation and safety infrastructure from scratch while preserving free speech values- The challenges and benefits of taking Reddit public while maintaining community ownership- How Reddit is addressing AI-generated content and the fight for human authenticity online- The business model evolution from advertising to AI data licensing partnerships- Steve's vision to make Reddit "universal" and expand from 100 million to billions of usersIn this episode, we cover: (00:00) Introduction and Reddit's 20-year milestone(02:40) Early product-market fit signals and the $10M acquisition (06:25) Steve's 9-year absence and return in 2015 (08:30) Content moderation challenges and building safety infrastructure (14:10) Reddit's three evolutionary eras and strategic positioning (16:40) The subreddit explosion and community self-organization (18:08) Positioning as the human platform in an artificial world (19:15) Human verification challenges and potential solutions (25:22) AI partnerships, data licensing, and monetization strategy (29:02) Search evolution and Reddit's role in the new ecosystem (35:07) Leadership philosophy and staying true to company values (37:43) The decision to go public and community ownership (42:18) Managing public company pressures while maintaining long-term vision (48:27) Steve's vision for Reddit's universal future

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 AI, and the impact of AI on search engines and Google's business model. Paul highlights the importance of open-source AI in preventing centralized control, and shares thoughts on how the interplay between truth and narrative shapes our perception of reality. This episode offers valuable insights for founders and aspiring entrepreneurs from one of the most experienced builders in the tech industry, discussing common pitfalls in startup narratives and the importance of seeking disconfirming evidence.