I wasn’t intentionally seeking out the co-founder of an up-and-coming AI first document editor. I was simply scrolling through Twitter a few months back, and I saw a funny post about the Sam Altman Open AI debacle.
I click on the account, and it’s this tech bro type who happens to go to the same university as me. He has the coolest personal website I’ve ever seen, and his projects catch my eye. His undertakings weren’t corny, and they surely weren’t the typical “generic SQL projects” meant to impress college admissions officers; they exuded genuine passion. This guy seems like he is passionate about what he does.
Declan Gessel is a junior at UC Berkeley, originally from Pennsylvania… but that intro doesn’t reveal the real Declan. Let’s try again.
Successful Entrepreneur Turned Berkeley Student
Declan Gessel is the Co-Founder of JotBot, an AI first document editor that’s looking to disrupt Google Docs and Notion. Curious, I cold emailed him, asking if he’d like to be featured in REG’s Fireside Chat series. Thanks to my @berkeley.edu email address and handsome profile pic, he responded, and we set up a time to chat.
Rajveer: Hey man, thanks for taking the time out to do this. How’s it going?
Declan: Good. (Takes a sip of his flavored sparkling water.)
I learned that his entrepreneurial story doesn’t start with JotBot; it instead starts with Rubik’s cubes. He used to import them from China and sell them to his middle school classmates at a markup. The assistant principal was, predictably, not too happy about this and shut down Declan’s suburban Temu.
Instead of giving up, he started flipping sneakers. Declan quickly realized that selling pickaxes and shovels would be far more lucrative; henceforth, he launched steadysoles.com, a $25 monthly membership for sneakerheads. Steadysoles provided services to sneakerheads to make it easier to buy exclusive shoes. They scraped websites and created a unified platform to view the restock and release dates of shoes. They also built auto checkout functionality and even provided 1 on 1 customer service to their users.
Coming off the high of these successes, college application season rolled around for Declan. Although he was engrossed in his entrepreneurial ventures, his parents were adamant that he at least apply to school. Declan applied to 20+ schools with the editing help of a dynamic one-woman team (his mom). Adamant on remaining in the startup ecosystem, Declan wanted to attend college in California. Rejected from Stanford, but admitted to UC Berkeley, he packed his bags for the West coast. (If he had REG counselors, he may very well have gotten into Stanford… but I digress).
Co-Founding an AI First Document Editor
While at Berkeley, Declan built a social alarm clock app that allowed users’ friends to record audio and send it to them as their wake up call in the morning. The app blew up, with thousands of downloads in the first week. The team quickly noticed that users dropped off after using the app for one week, indicative of the social friction involved in sending audio messages on a frequent basis. Most people would have given up, counted their chips, patted each other on the back, and moved on. Not Declan and his co-founder. They pivoted, instead building an AI alarm clock whose wake up calls featured auto-generated voices of celebrities. This solution retained the functionality of a personalized voice alarm clock while solving the problems associated with social friction.
Raj: A lot of people say that they want to build a business or make an app, but very few actually do it, and even fewer actually succeed. How did you manage to get this stuff off the ground?
Declan: Just grinding.
And the grind has continued with JotBot, the AI first document editor. It can summarize recorded lectures and talks, generate content that is unique to your writing style, and help you generate relevant contextual information. Declan and the team continue to ship features frequently, earning millions of impressions on their short-form marketing content. Now, they are taking time off school to go all-in on their startup.
The purpose of this Fireside chat isn’t for me to just butter up Declan and his Co-Founder; it’s for learning. What can we learn from Declan?
Raj: What advice would you give to high school juniors and seniors?
Declan: Build cool stuff, and put it out there for others to use, because it feels so good to have other people using your product.
He explained how students realize that they need a portfolio, and they end up making a website or doing some SQL project that will likely fool admissions officers and interviewers. He goes on to explain that it’s much more worthwhile to instead make something fun and useful. Most importantly, put it out there for others to use, because having people use your product “feels so good.”
Rapid Fire Q’s
Raj: Favorite Podcasts?
Declan: Huberman Lab, Lex Friedman, Diary of a CEO. Also, I hate the All In Podcast. You can put that in the article.
Raj: Favorite Book?
Declan: Can’t Hurt Me – David Goggins
Raj: Where (geographically) are you gonna build your startup?
Declan: SF (the vibes are awesome).
Thanks for reading, and go use JotBot.