Bailey Pumfleet, CEO of Cal.com and an innovator in open-source scheduling, shares insights on building a groundbreaking infrastructure company. He discusses the importance of transparency in a remote work environment and the challenges and strategies of launching an open-source project. Pumfleet emphasizes the analogy of 'Stripe for Time' to highlight efficient scheduling solutions. He also touches on fundraising strategies, customer understanding, and the impact of open-source technology on community empowerment. This conversation is rich with entrepreneurial wisdom!

Eoghan McCabe is the CEO and co-founder of IntercomThis was an incredible talk recorded live during the ODF22 cohort. Thanks again to Intercom for hosting.10 important ideas (and timestamps) from this conversation:1/ Innocence and Naivety Can Be a Superpower7:58 - “There was a phenomenal amount of naivety that allowed people to do things that were kind of like conventionally the wrong thing to do.”2/ Be Contrarian, but Not Recklessly So10:05 - “If you talk to 100 funds right now and you can’t raise money, change the damn idea.”3/ In-Person Work is Better11:55 - “In person is better. And I think that the people who promote remote working are lazy and antisocial.”4/ Find Your True Passion—or You'll Fail17:55 - “Please follow your passion. Please do the thing that you love.”5/ Great Companies Ride Multiple Waves21:23 - “Great companies are built on successive waves… secular movements. They either create them themselves or they jump on ones that have started already.”6/ Hard Work is Under Attack—But It's Essential23:37 - “Most likely you’re going to want to need to work seven days a week and 12 hours a day to get your thing off the ground.”7/ Extreme Homogeneity Early On Beats Diversity25:03 - “In early-stage startups, you want extreme homogeneity. You want people who believe what you believe.”8/ Customer Intimacy Over Everything26:29 - “They’ll obsess about talking to customers… getting inside not just their heads but their hearts.”9/ Early Failure and Rejection Strengthens You29:08 - “The things that bruise our egos the most tend to eviscerate the parts of our ego that were making us so fragile in the first place.”10/ Hiring Brilliant People is More Important than the Idea41:51 - “The people who put that team together had an eye for that X factor.”--If you're exploring starting a company apply for ODF - our 23rd cohort kicks off November 8th in San Francisco

Today we’re chatting with Mo El Mahallawy, CTO and co-founder of Shepherd.Shepherd is all in one commercial insurance platform focused on high hazard industries. The company is on an absolute tear and this month they announced a $13.5M series A.Mo and I decided to sit down and record a conversation because the journey of Shepherd will resonate with many potential founders who are try to find those two key missing pieces: who might I start a company with and what might we build together?Right as the world was shutting down due to COVID, Mo joined ODF3 where he met one of his co-founders at Shepherd — Justin Levine. Mo and Justin soon embarked on a journey to determine what they could build together that had potential to solve a real customer problem.After pivoting through several ideas across a variety of sectors, they honed in on an area where one of them had a unique insight — construction insurance.This is an instructive story about how to find co-founders and how to build a great business together. Enjoy!Are you exploring starting a company? We’ve got a program for that!ODF has helped 1k companies like Shepherd (ODF3) find their co-founders, get started and go on to raise over $2B. Applications for our IRL cohorts in San Francisco are now open. Learn more and apply at beondeck.comMo on X/Twitter and his company Shepherd.beondeck.comOn Deck on X/TwitterJulian on X/Twitter and blogPodcast episode archive and show notes

Today’s conversation is rare but vital — we spend much of our time talking about the challenges around shutting down companies. While I spend most of my time writing about how to build towards success, the stark reality is that most companies fail. Shutting down your company is incredibly painful but it’s particularly lonely — you often feel like you have limited support and guidance.That’s why Stevie and I felt it was so important to record this episode. We hope this episode is a resource to every founder in the years ahead that makes the decision that it’s time to move on. It’s packed with personal stories from Stevie, tested tactics, and best practices.We also spend some time talking about startups, identity, and the long arc of ambition. Contrary to what you might expect, I found this to be an inspiring and entertaining conversation — I think you will as well.Are you exploring starting a company? We’ve got a program for that!ODF has helped 1k companies get started and go on to raise over $2B. Applications for our IRL cohorts in San Francisco are now open. Learn more and apply at beondeck.comStevie on X/Twitter and her newsletter Highly Regulatedbeondeck.comOn Deck on X/TwitterJulian on X/Twitter and blogPodcast episode archive and show notes

Sasha Orloff, Puzzle's CEO, talks about the importance of accounting for startups and how Puzzle's software simplifies financial management. They discuss the challenges of fundraising, the need for a strong network and compelling story, and the importance of passion and curiosity in building a successful company. They also explore the pain of scaling and the opportunity in the accounting and finance industry.

AI expert, Matt Rastovac, discusses building AI-powered workflows with Respell, educating customers about breakthrough technology, transitioning into a CEO role, and unique talent evaluation. They explore the empowering aspect of automation, the potential implications of AGI and automation, and the role of talent in AI development. They also discuss Respell's talent acquisition strategies, the difference between horizontal and vertical AI solutions, and the benefits of the ODF program for starting a company.

Celine Halioua, Founder/CEO of Loyal, announced FDA approval for a drug that can extend lifespan, a groundbreaking milestone in longevity biotech. The podcast explores the pursuit of immortality, targeting root causes of aging, challenges in aging research, and a young female founder's experience in the biotech industry.

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.Defense Tech is a big deal. We’re just now starting to see it be thought of as a more feasible sector to build startups. Mike might be one of the best people in the world to learn about opportunities to build tech and services that support America and our allies.Before co-founding Shift, Mike felt a calling to serve and joined the United States Naval Academy and was a bomb disposal officer for half a decade.Mike’s first experiences with business go all the way back to when he was a kid helping his grandma Betty run her toy store. As a teenager he became an eBay power seller to generate an additional income stream for their business.In just under 10 days Mike is hosting the Defense Venture Summit, convening founders, operators, over 100 VC funds, and members of the US Military. It’s likely sold out as of publication. But if you are interested feel free to DM Mike on Twitter to see if you can be included.In this episode, Mike and I discuss opportunities in defense tech, a history of the sector, what he’s learned building a premier talent org, hiring veterans, and much more.Are you exploring starting a company we’ve got a program for that.ODF has helped 1k companies get started and go on to raise over $2B.I’m actually recording this podcast intro at our partner Carta’s office as they are hosting us during the 19th cohort of ODF happening right now. The energy is incredible — I’m excited to see what this cohort builds.We’ve just started reviewing applications for our 20th cohort taking place in San Francisco in late January. Learn more and apply at beondeck.comWithout further ado, here’s my conversation with Mike Slagh

In this episode of The Deep End, Max Greenwald, co-founder of Warmly, shares the mistakes and lessons learned on the journey towards building a product that customers love. Topics discussed include communicating changes to investors and teammates, avoiding the sunk cost fallacy, working with initial design partners, and more.

Elaine Zelby, co-founder of Tofu and a VC, talks about startup priorities, evaluating co-founders, fundraising in 2023, and the capabilities of generative AI. They discuss the challenges of transforming written content into audio, tool coordination in organizations, starting a company, and the potential of generative AI models in text, image, and video. Fundraising strategy and lessons learned are also shared.