The Emotional Toll of Selling a Startup

The journey to a calm, profitable business in the AI age

We’re building a mini-AI media and software empire at Every. 

Today on AI & I, Brandon Gell joins the show to turn the tables on me and act as podcast host to explore what we’re doing as a company, how we got here, and where we’re going.

Brandon is Every’s first entrepreneur in residence, and he was the perfect person to host, because he’s one of the key reasons for our recent acceleration.

Before joining Every, Brandon was the cofounder and CEO of Clyde, a startup that helped brands launch their own insurance and warranty programs, where he raised $50 million and led a team of 100 before selling it to global insurance tech company Cover Genius in early 2023.

In this episode, he interviews me about how I learned to code in middle school, how I built and sold my first startup coming out of college, and how it all led to Every.

We also talk about Brandon’s story. He joined Every just four months ago—and it feels like we’ve done the work of years since. We’ve launched two new AI products, an incredible amount of great writing, a new course, and more.

We get into:

• My candid thoughts on entrepreneurship in the AI age—including why you should ship fast, and how not to be misled by metrics like TAM 
• How AI startups can find valuable niches—and live demos of our apps Spiral and Sparkle
• Brandon’s hard-earned lessons from running a insuretech business for seven years
• The confusing realities of being an exited founder, and how we navigated through those times
• What brought Brandon to Every—including the email he sent me before joining
• Every’s master plan and what we hope to build over the next few months and years

This is a must-watch for anyone interested in building a calm, profitable business empire in the age of AI. 

If you found this episode interesting, please like, subscribe, comment, and share! 

Want even more?

Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It’s usually only for paying subscribers, but you can get it here for free.

To hear more from Dan Shipper:

• Subscribe to Every: https://every.to/subscribe 

• Follow him on X: https://twitter.com/danshipper 

Timestamps:

1. Introduction: 00:00:56

2. Dan’s childhood dream—to build a Microsoft competitor: 00:03:36

3. The first app Dan built in middle school: 00:07:07

4. The story of Dan’s first company that he sold in college: 00:18:52

5. How Every came to be: 00:33:56

6. The start of Brandon’s journey as a builder: 00:49:15

7. Brandon’s first software app—and why you should launch first, and iterate later: 00:57:05

8. Everything Brandon learned from running a B2B business for seven years: 01:08:49

9. What brought Brandon to Every—and the email he sent Dan before joining: 01:18:00

10. Every’s master plan to be a successful creator-run business: 01:29:15 

11. Live demo of Spiral, the app that automates 80 percent of repetitive creative work: 01:38:11

12. Brandon and Dan’s take on how AI startups can find a valuable niche: 01:44:00

13. Live demo of Sparkle, the app that organizes your files for you: 01:50:52

Links to resources mentioned in the episode:

• Brandon Gell: https://twitter.com/bran_don_gell
• The piece Dan recently published about Every’s master plan: https://every.to/chain-of-thought/every-s-master-plan 
• Dan’s piece about the unbundling of Excel, and why it serves as an important story in the age of AI: https://every.to/chain-of-thought/the-great-ai-unbundling 
• Tomasz Tunguz, the VC who has also written about Excel: https://tomtunguz.com/ 
• Every cofounder Nathan’s word processor, Lex: https://lex.page/ 
• Spiral, the app that automates 80 percent of repetitive creative work: https://spiral.computer/ 
• Sparkle, the app that automatically organizes your files: https://makeitsparkle.co/