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.

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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.