Founders in Arms

Immad Akhund and Rajat Suri

In this weekly series, fellow startup founders Immad Akhund (Mercury) and Rajat Suri (Presto, Lima, and Lyft) explore current events in the world of tech, startup, and policy, offering insights from their distinguished careers and an array of expert guests. YouTube: youtube.com/@FoundersInArms Substack: foundersinarms.substack.com Instagram: instagram.com/foundersinarms TikTok: tiktok.com/@foundersinarms_

  1. HACE 3 DÍAS

    The AI Superconnector Transforming The Future Of Networking With Andrew D’Souza (Founder & CEO, Boardy)

    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 reality In 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

    51 min

  2. 19 SEP

    Building an AI Business Beyond the Hype with Jesse Zhang from Decagon

    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.

    49 min

  3. 12 SEP

    Inside David Gu’s $38M Raise: The Pivot That Put Recall.ai on the Map

    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 recording acceptance created a massive infrastructure opportunity The systematic approach David used to learn enterprise sales with zero experience How Recall's desktop recording SDK eliminates the need for bots in meetings Why Series B fundraising still requires a 100x growth vision even at scale The framework David uses to validate new products and channels before investing time How Amanda Gu built 45,000 LinkedIn followers and turned social media into a lead generation engine Why David records and reviews every sales pitch to improve his closing rate The mental shift from seeking external validation to embracing continuous failure How the conversation data revolution will transform every B2B software application In 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

    55 min

  4. 5 SEP

    Building and Selling in "Impossible" Markets with WePay's Bill Clerico

    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 opportunities The unconventional partnership strategy that led to WePay's $400M JPMorgan acquisition How to position strategic partnerships as pathways to acquisition rather than just revenue Why WePay's delayed pivot from consumer to developer APIs cost them market leadership The specific tactics for getting enterprise buyers excited about acquisition vs. partnerships How to navigate the early fintech landscape without established banking infrastructure Why timing strategic decisions matters more than perfecting the original plan The 12-18 month timeline required for enterprise acquisition conversations How crisis-driven industries create first-time openings for technology adoption Bill's contrarian thesis on investing in utilities, insurance, and government sectors In 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

    47 min

  5. 29 AGO

    Frugality, Grit, and Scale: Inside Joris Poort’s Founder Playbook

    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 profitability How to avoid false trade-offs by asking "why not both?" instead of accepting either/or decisions Why the biggest startup mistakes are always people, especially bad executive hires The hidden advantages of grinding through difficult early years versus overnight success How to maintain frugal company culture while scaling from 4 to 200+ employees Strategic approaches to long-term R&D investments, including AI physics and Department of Defense contracts The difference between executives who built systems versus those who just ran them Why promoting internal talent often works better than external executive hires How to structure resource allocation decisions to force proper prioritization The psychology of founder endurance and why some businesses are intentionally harder to build In 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

    51 min

  6. 25 AGO

    Building in Defense Tech and Sovereign AI with Mattermost's Ian Tien

    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 technology In 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

    55 min

  7. 18 AGO

    Building Enterprise AI That Actually Works with Glean's Arvind Jain

    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 scale In 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

    52 min

  8. 8 AGO

    The Best Hack to Product Market Fit With Hiten Shah (Crazy Egg, KISSmetrics, Nira, sold to Dropbox)

    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.

    55 min
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In this weekly series, fellow startup founders Immad Akhund (Mercury) and Rajat Suri (Presto, Lima, and Lyft) explore current events in the world of tech, startup, and policy, offering insights from their distinguished careers and an array of expert guests. YouTube: youtube.com/@FoundersInArms Substack: foundersinarms.substack.com Instagram: instagram.com/foundersinarms TikTok: tiktok.com/@foundersinarms_

Información

  • Creador
    Immad Akhund and Rajat Suri
  • Años de actividad
    2023 - 2025
  • Episodios
    78
  • Clasificación
    Apto
  • Copyright
    © Copyright 2025 Immad Akhund and Rajat Suri
  • Mostrar sitio web
    Founders in Arms

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