Here's how Cal.com CEO Bailey Pumfleet turned a side project into one of the most ambitious and fastest-growing infrastructure startups ever.

Eoghan (CEO and co-founder of Intercom) joins ODF for a wide-ranging conversation about his experiences building a successful startup in San Francisco and his advice for other founders.

Discussion focused on finding your co-founder and navigating the idea maze.

Deep Dive with Stevie Cline (ODF4) — managing partner at Vol. 1 Ventures — on shutting down startups, founder identity, and the long arc of ambition. Prior to VC, Stevie was a partner at a major law firm and her blog Highly Regulated covers regulatory and compliance in tech and is read by tens of thousands of subscribers each month.

Sasha Orloff is the co-founder and CEO of Puzzle, a company that builds modern accounting software specifically for startups.

Matt Rastovac is the founder of Respell, a company that builds AI-powered workflows and agents to assist on tasks enabling individuals and teams can be more effective than ever before.

Loyal (ODF2) has earned what they believe to be the FDA’s first-ever formal acceptance that a drug can be developed and approved for lifespan extension. Truly groundbreaking. You’re about to listen to an archival interview with Celine just one and a half years into starting Loyal which is now 4 years old. It’s an incredible conversation with interviewer Marshall Kosloff and shows just how much can be accomplished in a few short years.

Joining me in the deep end is US Navy veteran Mike Slagh — founder of Shift — an organization that has built the most significant bridge between the Department of Defense and the startup ecosystem.

Max Greenwald met his co-founder Alan via ODF (applications for ODF19 close this week) and co-founded Warmly—a startup whose path has been anything but a straight line. After a few years of pivots they've come out the other end and have a product that customers absolutely love and are eager to pay for. In this candid conversation, Max generously shares his experiences alongside actionable lessons earned from navigating the journey to building a successful product.

Elaine Zelby just raised $5M from Index Ventures to empower marketers with generative AI. She sits down with On Deck co-founder Julian Weisser to discuss how to decide what your startup should build first, what to consider when evaluating potential co-founders, how to think about fundraising in 2023, and the current capabilities of generative AI. ODF has helped 1k companies get started and go on to raise over $2B. Applications for our 19th cohort in San Francisco are due this week. Learn more and apply at beondeck.com

On Deck launched the latest iteration of On Deck Founders (ODF), doubling down on an intensive one-week, fully-IRL experience in San Francisco. On this episode of The Deep End, Julian Weisser – co-founder of On Deck – sits down with Marshall to discuss the latest from a program that has helped launch over 1,000 startups. Applications for the next cohort of On Deck Founders close on Tuesday, October 24th at 23:59 PST. If you’re exploring starting a company and want to figure out what to build and with whom, we’d love to chat. Apply today at https://beondeck.com

Joining us in The Deep End today is Amrit Singh. Amrit Singh is the co-founder of Loop Health, the fastest-growing health insurance startup in India. Loop Health has raised over $40M, led by General Catalyst and Elevation Capital. As we delve deeper into the meta-series of longevity, we engage in a captivating conversation with Amrit, exploring how Loop Health incentivizes health for its users. We'll also venture into the exciting frontiers of the longevity movement and the pivotal role health insurance plays in ensuring our well-being for the long term.

Joining us today in The Deep End is Wallace Torres. Wallace is the Co-Founder of WellTheory. WellTheory is an early-stage startup with a pretty powerful mission: combating the autoimmune epidemic through the use of food as medicine, community care, and personalized insights based on health data. During our conversation, we delve into the story behind WellTheory and the positive impact the startup has had on its customers: helping them decrease fatigue, minimize pain interference in their daily lives, and achieve higher overall life satisfaction. We also explore the various models present in the digital health space, take a closer look at WellTheory's recent pivot towards partnerships, explore the importance of community in the digital health space, and reflect on the challenges of implementing and sustaining community spaces effectively.

Joining us today in The Deep End is Viswa Colluru, the CEO & Founder of Enveda Biosciences. Enveda has raised $175M in their quest to translate nature into medicine. Before founding Enveda, Viswa obtained a PhD in cellular and molecular biology, and started his career as a product manager at Recursion Pharmaceuticals. As our first guest in this series focusing on longevity and health, we speak to Viswa on why nature holds the great untapped potential for new drug discovery, why most drugs don’t work in human trials and what role artificial intelligence will play in unlocking biological and chemical data. We hope this conversation will give you a deep insight into nuances of the pharmaceutical industry, what the future holds for drug discovery and his advice for founders interested in this space.

Welcome to a new mini-series of The Deep End! In these mini-series we explore some of the most complex, societal problems facing us at the moment - helping listeners gain a nuanced understanding of a complex topic - and then be inspired and equipped to build, invest or support startups and founders that are aiming to solve these challenges. In the last mini-series, we looked at the meta-problem of access to housing. We looked at the main bottlenecks holding us back from achieving more accessible and affordable housing, and we spoke to the founders creating a new reality in this field. If you missed any of those episodes, head to wherever you find your podcasts and have a listen. For this mini-series, we are focusing on longevity: the pursuit of longer, healthier, and more fulfilling lives. The idea of living longer has captivated human imagination for centuries. While researching longevity, we identified eight bottlenecks holding us back from achieving longer and healthier lives, and we chatted with On Deck community members and founders to explore them.

Hey everyone, as we gear up for the launch of a new series on longevity next week, we wanted to re-publish this really timeley episode with Eugenia Kuyda, the founder and CEO of Replika, an AI companion company. Our conversation centers around the different use-cases of AI, from task-oriented chatbots to emotionally-supportive AI companionship. We delve into the current state of conversational tech, including how chatbots can become good listeners, and why Replika used a mixture of scripted retrievals and generative AI models for their product. We also discussed the past and future of AI and chatbots. Eugenia explains why task-oriented chatbots like a restaurant booking bot she had worked on previously didn’t catch on in the past, and the future she envisions where you can have an AI co-pilot of your life, like Jarvis from Iron Man, and how this can interact with her conception of the metaverse which she calls the “embodied internet”. This is a great episode for anyone who’s interested in possible futures of how AI can become a part of our lives, not only in helping us do things but in supporting our emotional and social lives. Let's dive in.

Joining us today in the Deep End is Julian Weisser. Julian is the co-founder of On Deck, and a prolific angel investor with over a hundred angel investments including Loyal, Level, Atmos, and more. Every few months, we invite Julian to the podcast to get a sense of what's going on in the world of venture, and this conversation is not different. We look at the growing importance of profitability and revenue generation for investors, as well as the importance of founders aligning their trajectory with investor expectations. We also look at alternative funding models, with Julian discussing Zapier and Bubble’s model of prioritizing revenue and profitability over heavy venture funding. This episode is a must-listen for anyone interested in understanding the evolving venture capital landscape or thinking about fundraising.

Joining us today in the Deep End is Varun Bhanot. Varun is the co-founder and CEO of Magic AI, a home fitness system that uses AI to give you personalised training on a beautifully designed mirror. Prior to building Magic AI, Varun was the co-founder and CEO of Unhoused, a non-profit that leveraged technology to reduce homelessness. He also participated On Deck Founder’s third cohort. In this conversation, we discuss Varun’s approach to health & longevity. We cover his personal weight loss and gym journey, why European health tech startups have received less attention from the market and what the future holds for longevity companies.

Joining us in The Deep End today is Will Jarvis, co-founder and CEO of Valuebase. Valuebase is building land-centric models to improve property valuations and mass appraisal modeling. Valuebase recently secured $1.6 million in funding, with Sam Altman's Hydrazine leading the round and On Deck participating. Prior to Valuebase, Will served as a Researcher in Residence at On Deck, making today's conversation particularly noteworthy. As we continue our series on housing, we'll discuss the importance of land, Georgism and taxation, navigating the intricate world of ideas, and much more. Let's get started.

Joining us on The Deep End today is Ryan Delk. Ryan is the CEO & Co-Founder of Primer, a startup creating a new education system for children, centered around microschools. Last year, Primer announced that they’ve raised $15M in new capital. Ryan previously worked in Growth + Partnerships at Gumroad, and then joined another marketplace company, Omni, and became COO. In this conversation, we explore where the inspiration for Primer came from, how Primer is overcoming regulatory barriers in the space, and why Ryan believes the best education system is a world-class teacher in as small an environment as possible.