The Deep End by ODF

CEO of Cal.com Bailey Pumfleet: building an open source rocketship ("Stripe for Time") | ODF alum

Cal.com CEO Bailey Pumfleet turned a side project into one of the most ambitious infrastructure companies ever. His mission: powering a billion connections by 2031 Rather than just another Calendly alternative, they're building the "Stripe for Time" - scheduling infrastructure that powers everything from doctor's appointments to refugee services. We get into: [3:56] How startups get open source wrong [10:46] Launching the v0 of Cal (called Calendso) [24:32] Why open source is crucial for infrastructure companies [36:30] The journey from MVP to enterprise-grade platform [39:29] Building trust through radical transparency [46:46] How their "longevity guarantee" wins enterprise deals [47:15] Running a fully remote global team [53:00] Handling compliance and security at scale This is a must-watch for anyone building infrastructure, open source, or startups in general.. Enjoy! Links mentioned: ODF: explore starting a startup in SF and figure out co-founders, customers, and more at https://joinodf.com StampList: browse breakout companies with a track record of sponsoring visas for exceptional talent at https://landing.club/stamplist https://cal.com https://x.com/BaileyPumfleet https://x.com/peer_rich (Bailey's co-founder) https://x.com/julianweisser The Deep End is available on YouTube and other podcasting platforms: https://www.youtube.com/watch?v=V2Pripb427E Apple: https://podcasts.apple.com/us/podcast/the-deep-end-by-odf/id1568752165 Spotify: https://open.spotify.com/show/4TWOlf80GM1Pml8fGUO8KK

Eoghan McCabe: moving to America to build Intercom into a unicorn + the benefits of naivety, hard work, and rejection.

Eoghan McCabe [https://twitter.com/eoghan] is the CEO and co-founder of Intercom [intercom.com] This 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 Superpower 7:58 - “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 So 10:05 - “If you talk to 100 funds right now and you can’t raise money, change the damn idea.” 3/ In-Person Work is Better 11:55 - “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 Fail 17:55 - “Please follow your passion. Please do the thing that you love.” 5/ Great Companies Ride Multiple Waves 21:23 - “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 Essential 23:37 - “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 Diversity 25:03 - “In early-stage startups, you want extreme homogeneity. You want people who believe what you believe.” 8/ Customer Intimacy Over Everything 26:29 - “They’ll obsess about talking to customers… getting inside not just their heads but their hearts.” 9/ Early Failure and Rejection Strengthens You 29:08 - “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 Idea 41:51 - “The people who put that team together had an eye for that X factor.” -- If you're exploring starting a company apply for ODF [joinodf.com] - our 23rd cohort kicks off November 8th in San Francisco

Deep Dive: Find the right co-founder and idea with Mo El Mahallawy, CTO and co-founder of Shepherd

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.com [http://beondeck.com/] * Mo on X/Twitter [https://twitter.com/MoFromYYZ/status/1755277489876930753] and his company Shepherd [https://shepherdinsurance.com/]. * beondeck.com [https://beondeck.com] * On Deck on X/Twitter [https://twitter.com/beondeck] * Julian on X/Twitter [https://twitter.com/julianweisser] and blog [https://textswithfounders.com] * Podcast episode archive and show notes [https://ideas.beondeck.com]

Deep Dive: Shutting down a startup, doing right by your team, and founder identity with Stevie Cline (VC at Vol. 1 Ventures)

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.com [http://beondeck.com/] * Stevie on X/Twitter [https://twitter.com/steviemctweets] and her newsletter Highly Regulated [https://www.highlyregulated.xyz/] * beondeck.com [https://beondeck.com] * On Deck on X/Twitter [https://twitter.com/beondeck] * Julian on X/Twitter [https://twitter.com/julianweisser] and blog [https://textswithfounders.com] * Podcast episode archive and show notes [https://ideas.beondeck.com]

Control Your Financial Destiny: Runway, Metrics, and more with Puzzle's CEO Sasha Orloff

ODF is thrilled to announce its partnership with Puzzle — all ODF participants and alumni now save hundreds of dollars, To learn more go here [https://community.beondeck.com/perks?q=puzzle]. -- Are you exploring starting a company? We’ve got a program for that! ODF has helped 1k companies—like Puzzle which was ODF8—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.com [http://beondeck.com/] * puzzle.io [https://puzzle.io] * Sasha on X/Twitter [https://twitter.com/beondeck/status/1724857047361990889] * beondeck.com [https://beondeck.com] * On Deck on X/Twitter [https://twitter.com/beondeck] * Podcast episode archive and show notes [https://ideas.beondeck.com] For this episode of the Deep End, Sasha dropped by On Deck co-founder Julian Weisser [https://twitter.com/julianweisser]'s house in SF to talk about why he decided to decade his next decade to building better accounting software for startups. Sasha realized that building Puzzle [https://puzzle.io] was essential for startups to have the best chance at thriving in an increasingly complex world. Puzzle puts accounting on autopilot and enables founders to be able to zoom in on any area of their business, model out scenarios, and plan for the future. It also makes the diligence process during finance and acquisitions go smoother.