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 infrast...
Dec 13, 2024•1 hr 9 min•Ep. 129
Eoghan McCabe is the CEO and co-founder of Intercom 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 ca...
Sep 30, 2024•1 hr 19 min•Ep. 128
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 ...
Feb 12, 2024•54 min•Ep. 127
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 e...
Feb 06, 2024•55 min•Ep. 126
ODF is thrilled to announce its partnership with Puzzle — all ODF participants and alumni now save hundreds of dollars, To learn more go here . -- 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 puzzle.io Sasha on X/Twitter beondeck.com On Deck on X/Twitter Podcast episode archive a...
Jan 19, 2024•50 min•Ep. 125
Are you exploring starting a company? We’ve got a program for that! ODF has helped 1k companies—like Respell which was ODF17—get started and go on to raise over $2B. Applications for our 20th cohort in San Francisco are now . Learn more and apply at beondeck.com respell.ai Matt on X/Twitter beondeck.com On Deck on X/Twitter Podcast episode archive and show notes For this episode of the Deep End, Matt Rastovac dropped by On Deck co-founder Julian Weisser 's house in SF to talk all things AI and h...
Dec 07, 2023•1 hr 5 min•Ep. 124
Earlier this week Celine Halioua (ODF2), founder and CEO of Loyal — a dog longevity biotech startup — announced something truly groundbreaking. 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. As Celine says in her announcement; “I started Loyal 4 years ago with the explicit goal to get the first drug FDA approved for lifespan extension itself - no disease, just healthy, longer"..."We can't st...
Dec 02, 2023•1 hr 8 min
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 ...
Nov 11, 2023•55 min•Ep. 123
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 19th cohort in San Francisco are due this week. Learn more and apply at beondeck.com -- Joining me in the deep end is Max Greenwald — co-founder of Warmly a startup that helps businesses turn warm leads into sales. The company recently announced their series A. I’ve known Max for years and watched the Warmly journey unfold — Max even met hi...
Oct 27, 2023•22 min•Ep. 122
Joining me in the deep end is Elaine Zelby — co-founder of Tofu ( https://www.tofuhq.com/ ) — a powerful generative AI platform that enables marketing teams to repurpose their content and run more successful campaigns. Tofu recently announced their $5M seed round led by Index Ventures. We’ve known Elaine for years — first as a friend, then as a participant in ODF2, then as an investor in On Deck during her time as a VC at SignalFire. She’s the first person we refer founders to when it comes to m...
Oct 24, 2023•39 min•Ep. 121
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 → beondeck.com
Oct 23, 2023•22 min•Ep. 120
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 i...
Aug 16, 2023•30 min•Ep. 119
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 l...
Aug 03, 2023•46 min•Ep. 118
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 ...
Jul 27, 2023•44 min•Ep. 117
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...
Jul 27, 2023•9 min•Ep. 116
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 retr...
Jul 19, 2023•45 min•Ep. 115
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 ...
Jul 12, 2023•24 min•Ep. 114
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 g...
Jun 29, 2023•36 min•Ep. 113
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 importanc...
Jun 15, 2023•41 min•Ep. 111
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 sp...
Jun 08, 2023•39 min•Ep. 110
Joining us today in the Deep End is Lauren Self. Lauren is the founder of Roots Homes, a fractional home ownership company, that allows you to build equity in your home while paying rent, which recently raised a $2.2M seed round. In this conversation we explore how Roots is finding the missing middle between renting and buying, helping ensure home-ownership comes with flexibility and how Roots is increasing access to the American dream. ---- View the full series on Housing: https://www.beondeck....
May 31, 2023•36 min•Ep. 109
Joining us in The Deep End today for our housing series is Kim-Mai Cutler, a partner at Initialized who invests in proptech, real estate, and climate. Kim's background as a financial markets reporter and early-stage venture startup enthusiast, allowed her to broaden her reporting to include the intersection of the industry and public policy. In 2014, her essay on TechCrunch titled "How Burrowing Owls Lead To Vomiting Anarchists (Or SF’s Housing Crisis Explained)" sparked almost a decade of publi...
May 24, 2023•41 min•Ep. 109
Over the past two years, we've interviewed 100+ people for our podcast, The Deep End. Now we're relaunching The Deep End as a multi-media publication, focused on problems worth solving. In the first series, we are tackling an issue that affects us all: access to housing. Our house provides us with a sense of belonging and serves as a sanctuary where we can retreat from the chaos of the world. Once we accept the importance of housing, our focus needs to shift to how we can make it more accessible...
May 24, 2023•10 min•Ep. 108
Joining us in The Deep End today is Vignan Velivela. Vignan is the co-founder and CEO of AtoB, a fintech payments platform modernizing the trucking industry’s financial system, which raised a $155M Series B last year. He was also a part of the On Deck Founders’ third cohort. We are taking a short break from our series on access to housing, to talk to Vignan about one of the biggest challenges facing us at the moment: transportation and logistics. In this episode, we cover the central and essenti...
May 10, 2023•50 min•Ep. 106
Joining us in The Deep End today is Tory Reiss. Tory is the CEO and co-Founder of Equi, an alternative investment hedge fund. Tory previously co-founded Archblock, a decentralized alternatives marketplace, and Harvest Money, an AI-driven debt management platform. We’re taking a quick break from our series on starting companies, to take a quick dive into the world of fintech. Our conversation with Tory today centers around how you can take control of your financial destiny and Tory’s journey from...
May 03, 2023•48 min•Ep. 107
Navigating the Idea Maze to The Unlikely Birth of Finch Finch, a platform providing a unified API for employment data, was born out of failure and uncertainty. Ansel Parikh and Jeremy Zhang, the co-founders, first met during On Deck's second cohort. Both were passionate about solving the plumbing behind big problems and gravitated towards challenging infrastructure issues. Finch was born out of failure. Initially, they attempted to launch an embedded lending platform, but the COVID-19 pandemic d...
Apr 27, 2023•44 min•Ep. 104
Gina Gotthilf is the co-founder and COO at Latitud, a platform helping build the next generation of iconic tech startups in Latin America through products, a dedicated fellowship and fund. Gina met her co-founder, Brian Requart, through On Deck. Before Latitud, Gina was the VP of Marketing and Growth at Duoloingo, helping scale the company from 3 to 200 million users, and worked on the Mike Bloomberg presidential campaign. Continuing with our series on the meta-problem of helping people start co...
Apr 05, 2023•45 min•Ep. 103
Joining us in The Deep End today is Sophie Alcorn. Sophie is the founder of Alcorn, a Silicon Valley immigration law firm that helps tech talent immigrate to the US. She is also the host of the podcast Immigration Law for Tech Startups and author the TechCrunch weekly immigration advice column “Dear Sophie.” Continuing with our series on the meta-problem of helping people start more companies, we talk to Sophie to understand why immigration is a bottleneck to company creation, and what founders,...
Mar 29, 2023•41 min•Ep. 102
On The Deep End today, we welcome Sasha Orloff, the Founder and CEO of Puzzle, a modern accounting software package for startups that recently raised $15 million in series A. Sasha joins us to discuss the use of accounting as a powerful decision-making tool and the creation of infrastructure to start and scale businesses, as part of our series on meta-problems to help founders start more companies. Despite advances in financial technology, Sasha believes that core accounting software remains out...
Mar 22, 2023•40 min•Ep. 101
Joining us on the Deep End today is Minn Kim. Minn spent a few years as an investor at Ridge, Bloomberg Beta and On Deck, backing founders as early as possible and is now building Plymouth to help extraordinary talent immigrate to the US. In this conversation we go deep into Minn’s core belief – that technology enables step changes in human agency. We discuss navigating the idea maze, picking who to start a company with, why immigration is key to innovation and so much more.
Mar 08, 2023•40 min•Ep. 100
