00 · always
The itch
I have always questioned things, and I have always enjoyed it. Why is it done this way? Who decided that? Most of the time the honest answer was “nobody thought about it.” So I stopped waiting for better solutions and started making my own.
01 · 7th grade
Candy
Every kid I knew ate their Halloween candy. I kept mine. The next October, in the days right before Halloween when every house on the street needed candy, I went door to door and sold it to my neighbors. Inventory cost: zero. That was my first business.
02 · 9th grade
Hours vs. ownership
My first job was coaching tennis the summer after 9th grade. I hated getting paid by the hour. So I started my own private coaching and kept the profit. Same work, different math.
That year I also shipped my first online product: a Roblox game, published under gamer748393. Over 10,000 lines of code. Over 1,000 visits. Zero dollars. I learned more from it than from any class I was taking.
03 · 10th grade
The API
When AI started taking off I learned how to call an API and built a small chatbot for fun. Then I took that and a Raspberry Pi to PI Kids, a nonprofit I was part of, and started a new AI division there, leading six students across California, India, and Brazil.
04 · clubs
Waffles
I founded Waffle Club. The entire pitch was free waffles. Within one quarter it was the third-largest club on campus. It also lost money every week, and I shut it down within a semester.
But I had bought something: attention. I spent it on my second club, AI Business Club, teaching how business and AI work together. We built a clothing brand with AI tools and took it past $8k in sales. One student I mentored there started a dropshipping business with the same tools and passed $50k.
05 · 11th grade
City hall
I led my Samsung Solve for Tomorrow team to the California state finals and my Real World Design Challenge team to a national honorable mention. Then I decided to start a nonprofit and had no idea how a 501(c)(3) worked. So I biked to city hall and asked the front desk. They walked me through all of it.
Apprentice AI grew to a team of 15+, raised over $10k, gave most of it away, and reached more than a thousand students.
That summer I co-founded my first real app, Skillbridge: hyperlocal tutoring that matched students and tutors by shared interests. I raised $1.5k from angel investors, meaning uncles and family friends. The app processed over $10k in sales. I paid every one of them back, plus 20%.
06 · UW
The safe path
At UW the goal quietly changed. Internships. Offers. Something stable. Everyone was doing it, so I did too: LeetCode, résumé projects, repeat.
Something still itched. I entered the Lavin startup competition with Compass, an AI companion for Seattle's dark months that suggests things to do when the rain starts and pairs you with people who want to do them. We won, which put me straight into the final round for the Lavin Entrepreneurship Program. I got in. Best decision I've made at UW.
Then Claryvn, a drug-interaction checker for dentists and orthodontists. A month of market research told us the truth, and we scrapped it. Then Equidar, a marketplace for buying and selling a percentage of a home's equity. Third place at the Buerk showcase.
07 · SF
The 9 to 5
Summer came, and with it my first taste of San Francisco tech life. I shipped production LLM features and cut inference latency 35%. I got tasks, finished them, went home. The pay was great. Nothing to worry about. And I could feel the spark going out.
08 · now
Back to building
When it ended I went to Berkeley Haas for Calvanize and built BioLay, the AI back office that independent rehab clinics can't afford to hire. We took first place and a spot in the StEP Incubator.
Back in Seattle I put all my time into building. I made Lobb: neighbors in the same building buy and sell everyday items, delivered to your door in about ten minutes. It's live. We'll see how it does.
None of the things that died were wasted. Each one taught me something the next one needed.
The biggest one starts now: Arlyn AI.