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 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 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.”

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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.com

• Mo on X/Twitter and his company Shepherd.
• beondeck.com
• On Deck on X/Twitter
• Julian on X/Twitter and blog
• Podcast 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.com

• Stevie on X/Twitter and her newsletter Highly Regulated
• beondeck.com
• On Deck on X/Twitter
• Julian on X/Twitter and blog
• Podcast episode archive and show notes

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 and show notes

For this episode of the Deep End, Sasha dropped by On Deck co-founder Julian Weisser'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 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.

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 his experience as a second-time founder.

With his new company Respell, Matt is building AI-powered workflows and agents to assist on tasks enabling individuals and teams can be more effective than ever before. During our conversation Matt shares how he thought through building the first version of Respell, how to educate potential customers about breakthrough technology, and what he’s learned about sales.

Prior to Respell, Matt was the co-founder and CTO of Atmos a vertically integrated solution for building a custom home. Matt shares what he learned at his first company, how he’s transitioned into the CEO role at his second one, his unique and compelling method of hiring and evaluating talent, and much more.

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 start selling the drug yet - we need to complete the safety and manufacturing technical sections - but this represents the lions share of the 'existential risk' of both the drug program, and of Loyal AKA - we are doing it!!!”

Laura Deming is a longevity biotech investor with an incredible batting average. 5 of 18 startups she’s backed so far have gone public. She was the first investor in Loyal and had this to say:

"This just dropped - the most important milestone in the history of longevity biotech. put simply, this is the FDA’s first-ever formal acceptance that a drug can be developed and approved to extend lifespan. the longevity field is evolving quickly. No one I know in the field would have said this was possible 5 years ago. Celine got it done in 4. It’s a massive win for both biotech founders and regulators, in establishing a pathway by which drugs (initially for dogs) can get approved for lifespan"

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.

Congrats to Celine and the entire Loyal team on what is truly an unparalleled milestone.

Are you exploring starting a company we’ve got a program for that?

ODF has helped 1k companies like Loyal which was ODF2 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

• loyalfordogs.com
• Celine's personal website
• Celine on X/Twitter
• beondeck.com
• On Deck on X/Twitter
• podcast episode archive and show notes

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.com

Without further ado, here’s my conversation with Mike Slagh

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

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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 his co-founder Alan through ODF.

Warmly’s path has not been a straight line. This conversation with Max is candid. He shares the mistakes and lessons learned on the journey towards building a product that customers love.

This might be one of the most useful episodes we’ve recorded on the deep end in terms of giving actionable guidance for founders.

In this episode, we discuss how to communicate changes in direction to investors and teammates, how to avoid the sunk cost fallacy, how to work with initial design partners, and much more.

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 marketing, growth or go-to-market.

In this episode, Elaine and On Deck co-founder Julian Weisser 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.

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