Building an AI Media and Software Empire

TL;DR: Today we’re releasing a new episode of our podcast AI & I. I go in depth with Brandon Gell, Every’s first entrepreneur in residence, and the former cofounder and CEO of insurance tech startup Clyde. We get into our journeys into the startup world, everything we’ve learned about entrepreneurship, and our philosophy around building at Every. Watch on X or YouTube, or listen on Spotify or Apple Podcasts.

We’ve been moving quickly at Every lately. In the last two months we’ve shipped:

• A new long-form essay about business and technology every weekday
• A new AI app to automate repetitive creative work, Spiral, which has 4,000 signups
• A new AI file cleaning app, Sparkle, which has already organized over 1 million files
• A new column with a talented writer about going 0-1 with AI, Learning Curve by Rhea Purohit
• A new cohort-based course to teach you how to write with AI taught by Evan Armstrong

It’s a lot! And there’s a lot more going on behind the scenes that I can’t talk about yet. I wrote an essay about Every’s “master plan” a month ago that explores some of what we’re doing and where we’re going. But I wanted to go deeper in a podcast episode. That’s what today’s show is all about. 

I invited Every’s first entrepreneur in residence, Brandon Gell, to come on the show and turn the tables. For the first half of the episode Brandon interviews me about how we got here—starting from when I learned to code in middle school, to how I built mobile apps to help pay for gas and food in high school, to the startup that I ran and sold coming out of college, to the early days of Every.

Brandon was the perfect person to act as interviewer, 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.

We dig into Brandon’s own story before joining Every and talk about the work he’s done since he’s been here, including how he got started building startups in college, how he founded Clyde, and what he learned building and selling it over seven years.

It’s the longest episode I’ve ever recorded, and it’s packed with lessons we’ve taken from founding and running startups over the course of our careers. We also talk extensively about how we think AI startups can create value, our recent product incubations, and the philosophy that underlies everything we do: to be ambitious, curious, and have fun while building. Here’s a link to the transcript of this episode.  

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

Watch on X or YouTube, or listen on Spotify or Apple Podcasts. 

If you want a quick summary, here’s a taste for paying subscribers:

My candid thoughts on being a successful founder  

The first time I sold software was in high school, and it was an app I built called “Find It.” I kept losing my Blackberry in my house, and I built a program where if you sent your Blackberry an email with a certain subject line, it would ring even if it was on silent. Given the rising popularity of smartphones, I had a feeling that software built on top of them would be valuable. I went on to build a few more side projects in college, like a web app that puts all your Facebook friends on a map, and one that reviews websites, before cofounding Firefly. Firefly was built around a technology called cobrowsing—screen sharing but instead of your desktop, you’re sharing a web page—that helps businesses provide instant support to their customers. It was acquired in 2014. 

After graduation, I spent some time “proverbially wandering the desert” before realizing that I wanted to start another company. Specifically, a company that gave people tools to organize their thoughts. I decided the best way to go about doing that would be to start a newsletter where I interviewed smart people about how they organize their thoughts, and then use those insights to build software, which I could sell back to the audience. “And what I tell people is for a long time, I just got stuck on building the newsletter,” I tell Brandon. 

Here are quotes from Brandon’s interview with me about how to thrive in your role as a founder: 

• Find meaning in the ambiguity. Founders are inherently curious people who thrive on the challenge of problem-solving in unfamiliar territory. As I would describe this mindset: “There's no manual, there's no instructions, I'm pretty behind, and I need to figure this out—and this is actually appealing to me instead of being so overwhelming…that I don't want to do it,” 
• Nurture a sustainable, enduring ambition. All the same, being an entrepreneur is stressful, and it’s important to be aware of what you’re experiencing to make sure you don’t burn out: “If you're a founder you get very used to running toward the stress, and to some degree it's exciting to have so much going on…[but] if you take it too far, it gets too much.”
• Launch first, perfect later. My advice for aspiring founders is to take action on their ideas and resist the temptation to overthink them because “it’s so easy to psych yourself out and convince yourself it's a bad idea…and the whole point of doing stuff at that early stage…is just learning how to make any kind of business.”
• Being everything for everyone is the same as being nothing to anyone. I believe that niching down to focus on a segment of the market can be more profitable than pursuing a broad market appeal. Even if the “total market size is bigger, it’s deceptive because the divided effort means you don’t get as far.”
• Finding yourself in the post-exit vacuum. It’s important to acknowledge that founders often continue to grapple with uncertainty even after they have exited the company. This is because there isn’t a “playbook” to deal with the fact that you “just lost [your] identity and the thing [you] do every day.” 

Brandon’s hard-earned lessons about B2B businesses  

I do, eventually, take back the mic as host of this podcast, and interview Brandon about his journey to entrepreneurship. Brandon studied architecture in college, where his early experiences “building” involved making physical objects, like furniture and a sustainable solar-powered house. His entrepreneurial journey in software began with an app called Photon, which made it easy for people to print photographs; progressed to insurance tech startup Clyde; and continues in his role as entrepreneur in residence at Every. This is what he’s learned about running a successful B2B business:

• Sharpen your problem-spotting radar. A big part of being a founder is being able to identify the right problems to solve. Even if there are “infinite numbers of problems” in existence, it’s “a muscle to recognize that something that you are experiencing is even a problem versus just your lived experience,” Brandon says, and then to define the scope of the problem. 
• Embrace and enjoy being in flux. After identifying the right problem, Brandon’s background in architecture equipped him with an important skill to find the solution: being comfortable in a constant state of iteration. “[M]y first design is going to be the worst or the best, I won't know until I throw a bunch of stuff at the wall, and it would be a big mistake to get stuck on what my first solution is,” he says. 
• Lead with your authentic strengths. Brandon challenges the notion that scaling a startup requires founders to trade in their passions for conventional CEO duties. He recommends a different approach: “You should just do the thing that you’re really good at and you like to do…it feels like such an unlock to do that with confidence.” 
• Prioritize what you believe in. A growing pain for young startups is their ability to stay true to their vision, even if that means turning down opportunities. For instance, in the early days of Clyde, Brandon stood firm against insurance companies pushing for exclusive deals that undermined their commitment to cheap consumer solutions, noting that if he gave in, “it felt like it wouldn’t be worth it.”
• What not to do after you raise money. Reflecting on Clyde’s early days, Brandon identifies three mistakes they made after their first round: underestimating competition, “which didn’t exist when we raised, but existed soon after”; misjudging time to value, “which when you close a deal, how quickly that business will start generating money for you”; and overspending. “We had money to spend and therefore we spent it.”
• Navigate retail’s fragmented ecosystem. Brandon identifies two challenges for B2B businesses selling implementation-heavy products to legacy retailers: the internal misalignment within client companies—“the right hand's not really talking to the left hand…so we'd have to resell” to different teams—and the industry's lack of standardization. “Retail is just a freaking mess,” he says. ”People use different ERPs…different headless software, and different e-commerce platforms.”

How AI startups can find a valuable niche—and demos of Sparkle and Spiral

As we talk, Brandon echoes an idea I recently wrote about: that LLMs will spawn niche startups, just like Excel did for B2B SaaS. He says that the future of AI-driven startups is to build “functionality on top of something that you could probably use Claude for, but you won’t.” In this vein, Every recently launched two AI products, and we demo them live on the show:

• Spiral is an app that automates repetitive creative work. You can train it to process input (like podcast transcripts) to generate output (like a tweet about the podcast). Brandon describes how it really works: After you copy and paste the transcript into the Spiral, “it takes this super prompt that we’ve built…[from] the bunch of examples that we’ve trained the Spiral on, send it to Claude, and return with output, which is a tweet.” 
• Sparkle is an AI file cleaning app that organizes your computer for you. Brandon explains: “Any file that you recently add to [your computer]...stays in Recents; the Manual Library is the place you can use if you don't want sparkle to organize…[certain] folders…and then, the AI Library is the magical place where I had thousands of files on my desktop and now they're just organized in my AI library.”

You can check out the episode on X, Spotify, Apple Podcasts, or YouTube. Links and timestamps are below:

• Watch on X
• Watch on YouTube
• Listen on Spotify (make sure to follow to help us rank!)
• Listen on Apple Podcasts

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

What do you use AI for? Have you found any interesting or surprising use cases? We want to hear from you—and we might even interview you. Reply here to talk to me!

Miss an episode? Catch up on my recent conversations with star podcaster Dwarkesh Patel, LinkedIn cofounder Reid Hoffman, a16z Podcast host Steph Smith, economist Tyler Cowen, writer and entrepreneur David Perell, founder and newsletter operator Ben Tossell, and others, and learn how they use AI to think, create, and relate.

If you’re enjoying my work, here are a few things I recommend:

• Subscribe to Every
• Follow me on X
• Subscribe to Every’s YouTube channel

Dan Shipper is the cofounder and CEO of Every, where he writes the Chain of Thought column and hosts the podcast AI & I. You can follow him on X at @danshipper and on LinkedIn, and Every on X at @every and on LinkedIn.