Stay ConnectedIn 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.
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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:
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
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:
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
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 users
In 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.
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 copyright licensing
How Created by Humans is building the "Spotify for AI rights"
Why books are the starting point—and the most complicated use case—in AI licensing
The three types of AI rights: training, reference (RAG), and transformative use
Why authors—not publishers—hold the keys to AI rights for books
How lawsuits between AI companies and authors are shaping the market
The long game of building two-sided marketplaces in emerging industries
Why Trip is prioritizing standards over fast ARR growth
Lessons from Scribd and why founding a second company feels different
How AI-human collaboration could reshape the creative economy
In this episode, we cover:
(00:00) Introducing Trip Adler and Created by Humans
(01:10) The explosion of startup culture since 2006
(03:26) Copyright in the AI era: the core problem
(07:13) Building a licensing marketplace for AI rights
(09:47) Author reactions: skepticism, enthusiasm, and early adoption
(10:48) Why this is like the music industry’s Napster-to-Spotify shift
(12:23) The future of licensing for video, music, and social media content
(15:34) The value hierarchy of data: books vs. tweets
(16:47) The three AI use cases: training, reference, and transformation
(20:32) Will AI replace authors—or collaborate with them?
(23:30) How AI might change the way we read and write books
(27:09) Lessons from Scribd: Why starting a second company feels different
(31:09) Avoiding short-term thinking and playing the long game
(35:25) Why founder journeys are marathons, not sprints
(37:40) Licensing clauses AI engineers need to read
(38:23) Authors reviving dead characters with AI
(39:13) Final thoughts: Building a creative economy that lasts
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.
What you'll learn:
In this episode, we cover:
(00:00) Introduction to Ryan Westerdahl and Turion Space
(01:31) Turion's satellite operations and space infrastructure mission
(07:18) Long development timelines and staying motivated through multi-year projects
(08:27) Ryan's journey from age 11 space obsession to SpaceX to founding Turion
(14:21) Engineering culture and the "hardcore" mentality required at SpaceX
(17:01) Building flat organizational structures and engineering-driven decision making
(22:30) The economic case for asteroid mining as humanity's galactic forcing function
(25:16) Hardware vs software engineering talent dynamics and motivation
(28:06) Early fundraising challenges and the importance of actual contracts over LOIs
(31:21) Current satellite operations: anomaly resolution and space domain awareness
(33:06) Immad's space investing thesis and evaluation criteria
(35:33) Science fiction culture at Turion and book recommendations
Adam Nash is the founder and CEO of Daffy, a donor-advised fund platform that's democratizing charitable giving for everyday Americans. Previously, he served as CEO of Wealthfront, where he helped grow the robo-advisor from $80 million to over $80 billion in assets under management. Before that, he held senior product roles at LinkedIn, eBay, and Apple.
What you'll learn:
In this episode, we cover:
(00:00) Introduction to Adam Nash and Daffy
(04:19) What donor-advised funds are and why they matter
(06:32) How Daffy is democratizing charitable giving
(12:23) The emotional connection behind successful products
(15:05) Wealthfront's journey from $80M to $80B
(21:14) The trust-building strategy that worked for fintech
(28:12) Subscription vs. transactional business models
(34:08) Designing organic network effects
(38:20) Adam's giving philosophy and approach
(44:18) The remote work fraud problem and trust issues
(52:00) Building ownership culture in startups
Alec Stapp is the Co-CEO of the Institute for Progress, a non-partisan innovation policy think tank in Washington D.C. works to accelerate and shape the direction of scientific, technological, and industrial progress. Headquartered in Washington D.C., IFP works with policymakers across the political spectrum to make it easier to build the future in the United States.
What you'll learn:
In this episode, we cover:
(00:00) Introduction to Alec Stapp and Institute for Progress
(02:02) Progress studies vs. progressive politics clarification
(05:08) What America is doing right in AI competition
(08:05) Immigration policy disappointments and opportunities
(10:02) Why government science funding matters for innovation
(13:52) The federal budget reality: entitlements vs. R&D spending
(16:20) National debt concerns and productivity growth solutions
(18:00) AI's economic disruption and the care economy transition
(23:16) Building stronger institutions for technological change
(25:47) Fertility rates, immigration, and America's competitive advantage
(29:13) U.S.-China relations and cultural similarities
(33:09) Solar energy, battery storage, and Republican energy policy
(39:06) Nuclear power's regulatory challenges and state-level solutions
(42:03) The Techno-Industrial Policy Playbook overview
(47:04) X Labs: Reforming how we fund scientific breakthroughs
(49:11) Naval shipbuilding procurement reform opportunities
Topher Haddad is the co-founder and CEO of Albedo, building satellites that fly in very low Earth orbit (VLEO) at 275km—twice as close as traditional imaging satellites. This proximity enables commercial imagery at resolutions previously only available from classified government systems or expensive aircraft operations.
What you'll learn:
In this episode, we cover:
(00:00) Introduction to Topher Haddad and Albedo
(01:04) What is VLEO and why fly satellites so low
(03:09) Engineering challenges of atmospheric drag and atomic oxygen
(06:12) Solar activity cycles and satellite lifetime considerations
(07:30) Commercial use cases replacing planes and drones
(11:41) Timeline from quitting Lockheed to first satellite launch
(13:24) The surprisingly low barrier to entry for simple satellites
(14:22) What space markets actually work today vs. future bets
(17:08) How launch cost reductions enable new business models
(19:04) Navigating defense sales and government relationships
(25:23) Why space startups survived the 2022 market crash
(38:41) The importance of pre-sales and customer deposits for deep tech
(46:03) Rapid fire: skateboarding, support systems, and space observations
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