Every’s First Entrepreneur in Residence, Brandon Gell

Former Clyde CEO will help us incubate new software and services businesses

Photo: Sarah Halliday.

TLDR: We brought on our first entrepreneur in residence, Brandon Gell. Previously, Brandon was the cofounder and CEO of insurtech startup Clyde, where he raised $50 million and built a team of over 100 people before selling it to CoverGenius in March 2023. He’s joining us to help us incubate new software and services businesses that we will bundle into paid Every subscriptions. 

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(Subscribers get access to all of our content, discounts on courses, and access to our AI writing app Lex.)

Why we brought Brandon on board

A note from Dan Shipper, CEO of Every

An essay is a great MVP for a product.

Writing an essay requires clear thinking. There’s a reason why Jeff Bezos instituted strategy memos instead of slide decks at Amazon: Writing exposes bad ideas and elevates good ones. 

When you’re writing, it’s also easy to tell when we’ve hit on an idea that resonates. Your audience will let you know. 

At Every, we believe that this cycle creates a great opportunity to incubate new products. Our writing provides a pipeline of good ideas that we can validate quickly. Subscribers like you become early adopters. And each new business gives us new things to write about—and affords the opportunity to bring in more talented writers. 

If that wasn’t enough, AI has dramatically decreased the cost of building new businesses, so small teams like ours have an incredible amount of leverage to build more with less capital. 

We’ve also done this before. In the fall of 2022, we incubated Lex, an AI writing app built by my cofounder Nathan, which we spun out as an independent company last year. Lex has raised almost $3 million from True Ventures and others, and is shipping beautiful software used by writers all over the world.

We’ve known for a long time that we wanted to do more product incubations. We just needed the right person to work with.

That’s why I’m excited to bring on Brandon as our first entrepreneur in residence. I met Brandon seven years ago when he was raising money for his last company, Clyde. Every investor has deals that they kick themselves for not jumping into—and Clyde was that for me.

I ended up on Brandon’s investor mailing list and received his updates every month. His notes struck me: They were concise, level-headed, and honest. Clyde’s growth was fast, especially in the early days, and even though Brandon was in his early twenties, the picture of his business that he painted in words felt rare. One especially notable detail: Despite being the driving force behind Clyde’s early success, Brandon’s updates almost never used the word “I”—he only used the word “we.”

I think that says something important about him. He’s one of the smartest and most ambitious founders I’ve come across, and he’s also a kind and empathetic human being who knows that company-building is a team sport. It’s a special combination. I’m psyched to have him aboard.

If you want to get early access to everything we build, subscribe below. Our products will be bundled into your Every subscription, along with:

  • Access to all of our articles
  • Discounts on courses
  • Access to our AI writing app, Lex

Why Brandon joined

A note from Brandon Gell, entrepreneur in residence

Reading Every changed my life. That sounds hyperbolic, but it’s true.

Over the past seven years, I started, scaled, and eventually sold Clyde, a platform that enables any business to launch and implement a product warranty program. As a co-founder and CEO, I experienced the entire startup lifecycle—from the early, 0-to-1 days of product discovery and selling it myself, all the way through launching multiple product lines, raising over $50 million, scaling to more than 100 people, downsizing to 50, and eventually selling. The ups were thrilling, and the downs were devastating. When people ask me what it’s like to be the CEO of a startup, I tell them it’s like getting punched in the face with a smile on…every day. 

But waking up each day and experiencing exhilarating progress followed by the inevitable challenges took its toll on me. I became more serious. I spent less time exploring new ideas with my colleagues and more time stressing about finishing tasks. What tasks? All of them. That was the problem. And when I wasn’t working, I was distracted. My wife could see it in my eyes while she was talking to me—I was only half-there. I was always thinking about work. Clyde had become not just my company, but my identity.

One morning an email from Every with the subject line "Be Sincere, Not Serious" arrived in my inbox. Intrigued, I opened it and started reading:

"Most of the time work was fun. Even when I clocked long hours on challenging projects, I enjoyed myself and looked forward to doing it again the next day. 
Other times, I was a tightly wound ball of stress who sucked the joy out of a room like a Dementor from Harry Potter. Even when my workload was lighter, things just felt difficult. Eventually, I realized the work itself wasn’t to blame—it was my attitude that was triggering one state or the other. For a long time I wondered what was going on."

I recognized myself in these words. I, too, sometimes sucked the energy out of a room, even when I knew I should be fueling it. I read on. 

The piece, written by Michael Ashcroft, is about how in life, you get to choose your perspective—you can be playful, silly, understanding, and joyful. You can enjoy the ride and be present, which, I think, is another form of sincerity. Or, you can be serious. You can cut out play in favor of execution. You can use up energy instead of giving it. Rather than lecture how people can or should live their lives to combat this feeling of seriousness, Michael discusses changing the lens through which we can view life itself. 

“Be sincere, not serious” became my mantra. I wrote it on a Post-it-note and stuck it to my computer. Later, when that fell off, I made it the wallpaper on my phone and computer.

Source: Brandon Gell.

It was an aha moment—a psychological unlock—of such magnitude that it has shifted the way in which I approach my life. I was still focused on the destination, but by continually returning to this mantra, I was able to be more present in the moment and get more enjoyment out of the journey. It helped me stay grounded.

A few months ago, another Every email caught my eye—“The One-person Billion-dollar Company” by Evan Armstrong. I had recently sold Clyde and was exploring what I wanted to do next. In his piece, Evan argues that when the cost to build and manage a business becomes so low because of AI that virtually anyone can do it, value accrues to those who own distribution. I finished the piece, reached out to Dan (an old friend), and proposed we explore this concept together.

I believe that negative CAC businesses—those that are built atop a distribution network where subscribers pay for content—are the future of SaaS. Dan, Evan, Kate, and the rest of the team have built an amazing foundation, and I think that Every can be the poster child for this model.

As an entrepreneur in residence at Every, I’ll be exploring the many ideas we have across the company. I see a special path forward for Every. You’ll see new business units launched, new products for our subscribers and beyond, and, hopefully, new ways to think about the future. We have a lot in store, and I sincerely can’t wait to share it with you. 

If you want to get early access to everything we build, subscribe below. Our products will be bundled into your Every subscription, along with:

  • Access to all of our articles
  • Discounts on courses
  • Access to our AI writing app, Lex

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@chewmattst 13 days ago

Fascinating can wait to read about the journey here; and excited to use the products and services!

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