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