Founders in Arms

Bill Clerico, the founder of WePay and now managing partner at Convective Capital, shares his journey from building a pioneering fintech startup during the 2008 financial crisis to selling it for $400 million. He discusses why avoiding certain sectors can reveal hidden opportunities and highlights the unconventional partnerships that led to WePay's acquisition by JPMorgan. Clerico also reflects on the importance of timing in strategic decisions and explores innovative solutions for high-fire risk insurance, revealing insights on navigating challenges in crisis-driven industries.

Joris Poort, CEO of Rescale, shares insights from his journey building a digital engineering platform that powers industries like aerospace and pharmaceuticals. He discusses the importance of being 'default alive' for startups, emphasizing cash flow over theoretical profits. Poort explores how maintaining a frugal culture while scaling is vital, and why internal promotions often yield better results than external hires. He also highlights the significance of resilience in hiring and the strategic risks involved in long-term R&D investments, especially in AI.

Ian Tien, co-founder and CEO of Mattermost, shares insights from transforming an HTML5 gaming concept into a vital collaboration tool for defense and national security. He delves into the intriguing idea of 'sovereign collaboration' and the necessity for governments to have independent AI systems. Ian discusses his lessons learned in navigating VC funding, hiring executives with diverse experiences, and the unique challenges of selling to government customers. He also emphasizes work-life balance through his 'daddy daughter days' approach.

Arvind Jain, Founder and CEO of Glean and co-founder of Rubrik, shares insights on revolutionizing enterprise AI. He explains how Glean transformed from a search tool to a powerful conversational AI without pivoting. Arvind discusses the significance of customer relationships in competitive markets, the challenge of attracting talent from major tech firms, and the balance between innovation and product alignment in a growing team. He also delves into the delicate decision between remaining independent or considering acquisition as the company scales.

Hiten Shah, a serial entrepreneur renowned for founding Crazy Egg and KISSmetrics, shares his insights on transitioning from startup founder to corporate employee at Dropbox. He reveals how to leverage existing product-market fits for new ventures, discusses the stark differences between self-funded and VC-backed paths, and emphasizes the importance of aligning passion with business. Shah also explores the cultural shifts post-acquisition, navigating the tech landscape, and the psychological aspects of building startups, providing invaluable lessons for entrepreneurs at all stages.

Steve Huffman, co-founder and CEO of Reddit, shares his journey in transforming one of the internet's most essential platforms over two decades. He discusses how Reddit achieved rapid product-market fit and the lessons from his early sale of the company. The conversation dives into Reddit's evolution, from a link aggregator to a space prioritizing authentic human content amidst AI challenges. Huffman also reflects on community ownership, navigating public offerings, and the future vision of making Reddit a universal hub for connection.

In this engaging conversation, Paul Buchheit, the creator of Gmail and a tech pioneer, shares his insights on the evolving AI landscape. He discusses the potential future of large language models and their impact on startups and society. Paul emphasizes the importance of open-source AI to prevent centralized control and addresses the changing dynamics of search engines. He also elaborates on the interplay of truth and narrative, urging listeners to confront false narratives for personal and entrepreneurial growth.

Trip Adler, Founder and CEO of Created by Humans, creates a marketplace to help rights holders license content for AI. He dives into the urgent question of how to fairly compensate creators whose work is used for AI training. Adler compares the current landscape to the music industry's transition from Napster to Spotify, discussing three types of AI rights: training, reference, and transformation. He shares lessons from his Scribd experience, the challenges faced by authors versus publishers, and the future of human-AI collaboration in creativity.

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:How Turion's "droid" satellites provide space domain awareness and anomaly resolution for other spacecraftWhy orbital debris removal serves as the stepping stone to asteroid mining operationsThe engineering culture principles Ryan brought from SpaceX to build a flat, department-driven organizationHow Space Force contracts provided early validation and multi-million dollar revenue opportunitiesThe difference between hardware and software engineering talent pools and motivation levelsWhy Ryan believes asteroid mining could be the economic forcing function for humanity's galactic expansionThe technical challenges of capturing uncooperative space objects at 35,000 mphHow a $400 quintillion asteroid could reshape precious metals markets like aluminum did historicallyThe 15-year timeline to meaningful asteroid mining revenue and building for the long termWhy mission-driven engineering culture attracts top talent willing to work on decade-spanning projectsIn 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

In this discussion, Adam Nash, the Founder and CEO of Daffy, a platform making charitable giving accessible, shares insights on revolutionizing philanthropy. He highlights the enormous potential of donor-advised funds, emphasizing emotional connections in giving. Adam explores how subscription models build customer loyalty and trust, key for startups. He also dives into the challenges of securing B2B clients and the importance of planned giving, showcasing how small steps can lead to meaningful generosity. His vision revolves around making charity simple for everyone.