Founders in Arms

Andrew D'Souza, Founder and CEO of Boardy AI, dives into transforming networking with voice-driven high-trust introductions. He shares how Clearco’s pivot to e-commerce financing led to rapid growth and illustrates the psychology behind networking and financial incentives. Discover how Boardy uses AI for richer relationship building, the importance of allowing mutual willingness in introductions, and why savvy founders leverage inbound demand to attract investors. D'Souza also reveals lessons learned from trusting intuition and his vision for the future of AI in networking.

Jesse Zhang, CEO and co-founder of Decagon.ai, discusses the challenges of building a sustainable AI business amidst the hype. He reveals how AI can evolve beyond chatbots into a true 'system of intelligence' for enterprises. The conversation dives into effective AI implementations, the realities of enterprise sales, and strategies to create defensible business models. Jesse also shares insights on credible growth metrics, adoption timelines, and the risks in fundraising, providing invaluable guidance for tech founders and customer experience leaders.

David Gu, co-founder and CEO of Recall.ai, shares his riveting journey from a university dropout to leading a company that recently raised $38 million in Series B funding. He discusses the key pivot from a call recording application to a conversation infrastructure leader, uncovering how societal acceptance of recording transformed the market. David reveals his approach to mastering enterprise sales, strategies for leveraging social media for lead generation, and the importance of continuous self-improvement through pitch reflections, shaping the future of B2B applications.

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.