My Story

After serving in the US Navy during WWII, my great-grandfather Robert Bailey founded Dick Bailey Service, Inc., to provide specialized printing services to a small niche of appellate attorneys in NYC. Robert’s founding team consisted of his four sons and would later expand to his grandchildren, and great-grandchildren.

Like many small businesses, the 2020 pandemic rattled the company. Within the first few months of it, the company headcount had quartered, and a new 13,000 sq ft office in Brooklyn was left vacant. The company was in the midst of a literal crisis.

At the time, the business was supporting the lives of 15 family members, including employees (current and former), spouses, and children. The business simply could not fail.

By the power of sacrifice, hard work, and sheer will, the company persisted, but the crisis threw workflow into a spiral. The company was forcibly transitioned from physical workflows to its first ever all-digital workflow. It sufficed for a while, but was implemented during crisis mode.

By 2022, it was time for a revamp, and the company chose monday.com. They experimented with some consultants for building out this new comprehensive internal workflow, but they were expensive, and required a lot of resources to get into the weeds on the complex legal processes that the business deals in.

Enter, me.

I had been working part time with the company since 2020, working on odds and ends while I was wrestling in high school. I was extremely lazy and took the whole opportunity for granted (normal 15-16yr old behavior), until I started tinkering with monday.com in late 2022 and early 2023.

My time with the company to that point gave me good enough context to build workflows, I just needed a bit more technical know-how. Luckily, I was literally at peak neuroplasticity. Within a year, I became one of the top monday.com experts on the planet, rocketed forward entirely by this new positive feedback loop that emerged for me.

Learn more > Work hard to help the company > Be valued and relied on > Derive purpose

At 18 yrs old, this was a humongous unlock for me. It started me down a beautiful path of entrepreneurship and adventure.

While this flywheel was going on during my senior year of HS, my groundbreaking rationale about what to study in college was essentially “I like sports and I’m interested in business, so I’ll study the intersection of the two”. Kidding aside, I had been (and still am) a lifelong fan of the UFC, and was targeting a career in the UFC.

I decided that I’d go away to the University of South Carolina for school and I’d be pursuing a Sports Management degree. To my credit, UofSC did have the literal best Sports Management program in the entire country, and I would have definitely achieved that goal of working for the UFC if I stuck to it.

I left NYC for South Carolina, and in my first month of freshman year I started six things in parallel:

I started a company, building software plugins for the monday.com app marketplace.
I started a job with a monday.com implementation partner agency as a workflow architect.
I started training Brazilian Jiu-Jitsu at a local martial arts school.
I started a club at the school for UFC fans to get together and watch the live events together on campus.
I started lifting weights every single day
I started college

Here’s how each of the six things looked at the end of my freshman year.

I partnered with a UofSC CS student, then created and launched 3 apps into the monday.com marketplace, generating actual paying customers. I was also the youngest monday partner ever.
I was promoted to lead architect at this agency within ~2 months, and subsequently led around two dozen workflow design projects for small businesses.
I trained jiu-jitsu relentlessly (sometimes 8x a week), and received my blue belt in a remarkably fast 6 months of training.
I hosted three events for my UFC club around three UFC live events. Had dozens of attendees. An employee of the UFC reached out to me and asked to chat towards the end of the year.
I lifted weights every single day of my freshman year (~250 days).
I had a 4.0 GPA.

Pretty solid year for me. Around January of that year I decided I wasn’t going to continue at UofSC because it was a waste of money. I was on a 30% scholarship, split the remaining balance with my parents, and still spent 20k out of my own pocket to pay for that first year. Also, the whole sports management idea lost its sparkle after I started having the tiniest bit of success in tech.

I decided that I’d transfer to a school closer to home for Sophomore year. I transferred to NYC’s Baruch College, which would be about a quarter of the price and an arguably stronger business school than UofSC.

During this semester at Baruch I was mainly working on the building and launch of my fourth monday.com app. Around this time I discovered the YCombinator YouTube channel. Solely because of that discovery, I ran probably a 10x better project/launch.

I started a waitlist, interviewed users on it, and built the product based on what the users wanted. Had a beta before launch, talked to users during the beta, then had a successful launch in Oct. 2024. Since then that specific app has grown about 10% MoM since launch with thousands of ARR.

By the end of the Fall 2024 semester at Baruch, I was pretty unhappy with school. I did well (3 A’s and 1 B), but felt like I was getting nothing out of it at all. To be fair I wasn’t putting much into it, but comparatively with the other things I was working on in my life, it was far and away the most dull and uninteresting.

Those feelings were like kindling, and then I had a conversation with my father that was the spark.

I was working in-person one day with the team from the family business. My Dad and I were in the car on the way home, and he said something along the lines of: “You should be doing this somewhere else, somewhere bigger and better.” The ensuing conversation was long, but that quote captures the essence of it. In an extremely unselfish moment, my own father told me to stop helping him and the family business, because I was capable of something greater.

I obliged.

After some careful thought about my options, I landed on tech startups as being my best bet. I think I was pretty on the money with that assumption.

Within a week I did about 80 cold reachouts to recently funded startups that I thought were cool. I got two replies, one in NYC, and one in SF. I visited the team in NYC, and they would have taken me in, but the opportunity in SF was more grand. More accomplished team, more funding raised, and it was also in the tech capital of the world.

I met the founder on video call three days in a row. 12/31, 1/1, and 1/2. These were three of the most emotional days of my life. I was extremely anxious and nervous in the time before our calls, and after they each went well I’d felt relieved, but also increasingly anxious as I confronted the reality that if I turned this opportunity down I would probably regret it for the rest of my life.

Within two weeks of the email reply from this SF startup I said goodbye to my family, dropped my classes for Spring 2025, and flew across the country.

In the almost nine months I spent in San Francisco with Endeavor, I learned more than any other nine month period in my life, by far. I spent almost every waking moment with the smartest people I ever met and got to travel to twelve different US cities.. I made lifelong friends, and spent enough time in an office building to hold me over for a few years.

I regret nothing, and I’m extremely grateful every day to have been born in the only country in the history of the world where risk-taking and ambition are as revered as they are here in the United States.