The AI First Document Editor on a Quest to Disrupt Google Docs -

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.

Screenshot of a tweet by Declan Gessel that says, "My girlfriend just texted me this...." An additional image says, "Hey, need to talk. Could you jump into this Google Meet in the next 10 mins? — Don’t get the joke? Sam Altman was fired on Google Meet.

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.

Screenshot of the JotBot homepage. A heading on the page reads, "JotBot Writes Like You." To the side is an image of JotBot-generated text. — Used from the JotBot website with permission.

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: Lol

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.

-Raj

Interested in studying business or tech? Check out our lists of the best schools for business and the best schools for computer science and engineering.

Sarah Gooch

Essay Editor

Q:How many total years of experience do you have in your current role, including but not limited to ReadyEdgeGo?

A: I have five years' experience in coaching student writing, but this is my first year with ReadyEdgeGo.

Q: What about working with students do you most enjoy?

A: I love helping students find depth and meaning in their own stories—but I also just love it when they make me laugh!

Q: What do you like to do in your free time?

A: In theory, I enjoy painting and writing poetry, but these days I actually spend most of my free time socializing or watching movies with my husband.

Q: What is your one piece of advice for high schoolers?

A: Don't just focus on achieving top grades and credentials because they look good on applications, or your education will be meaningless. The numbers and awards have their place, but stay connected to your sense of curiosity, discovery, excitement, and wonder so that the content you're learning is constantly transforming you—it's something you care about, something you remember after the final exam. Work on the aspects of yourself no one can measure, like integrity, wisdom, kindness, and compassion, so that you're not only developing your academic and career potential but also investing in the type of adult you're going to be, the person you'll have to live with after you clock out every day for the rest of your life.

Doing the hard inner work of building your character and learning deeply instead of just earning grades will set you up for a satisfying, well-rounded life. Strange as it sounds, it will also put you ahead in your academic and career goals, because colleges and hiring managers aren't looking for an empty set of data on a spreadsheet; they want a fully fleshed-out person marked by passion, creativity, and a story no one else has lived.

So go on studying hard for tests, but also spend some time asking yourself what matters in life and who your role models are. Read up on topics that amaze you, and build something incredible just for fun. Cultivate that spark of joy you feel when you're immersed in a subject that fascinates you. If you can hit that balancing act of doing your homework and meeting deadlines but also investing in the kind of person you want to be, then trust that all the rest will follow: schools will recognize you as a dynamic, all-star person, and you will also build a life of happiness, close relationships, and peace.

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