Work and Pursuits of Toil

Both of my parents were self-employed growing up, giving them flexibility in their day-to-day. But that flexibility came at the cost of self-reliance, financial uncertainty, and unconventional work schedules (my dad for example, would sometimes go TO his studio after dinner to start a recording session). It instilled in me what I'll wince and call an entrepreneurial spirit.

Humor me - let's start at the beginning!

When I was 13 I learned how to piece together computer components in my school's computer club. Games like World of Warcraft dominated the back-of-bus conversations, so there was a demand for high-powered gaming computers. I'd meet with a classmate and we'd customize the specs together, a setup replete with color-changing fans of course, and then I'd assemble and configure them. I think I charged a 10% fee. There were certainly some challenging builds and ongoing support issues - I remember spending hours at a kid's house troubleshooting a boot problem that at the time was far beyond my ability to comprehend, another time an errant screw caused a motherboard short during boot sometimes. This was, depending how you squint at it, my first foray into - echem - capitalism.

Around the same time, I started building websites for individuals and businesses. Sometimes it was exciting and creative, other times they'd ask me to clone, style for style, another company's website.

What really felt like the first "business" was Computer Camp. For a few years, I ran a summer camp for 4th through 8th graders with different technological themes each week: video editing, website development, Lego robotics, engineering, etc. It was a hit, we'd have 40+ kids per session, two sessions (morning and afternoon) per week. I hired all of my friends, rented the computer lab at my high school, and hired our math teacher to chaperone (and make it minimally viable for an insurance policy). I had spreadsheets to run our expenses (spare Lego motors, snacks, wages) and revenues (camp fees). At the time I had no idea what I was doing but in retrospect it was very much like my job is now as a CEO. The best part of it all was of course the actual teaching - the pure joy when a campers website rendered a list of favorite dragons, their Lego robot completed a tricky task, or the egg they armored and tossed off the school roof survived the fall.

Between camp and graduating college, I worked a series of summer jobs - I did two summers at Emma Email Marketing, the tech company in Nashville, TN in '09 and '10. I got some exposure to IT and infosec, with some exciting visits to the data center!

That work on my resume helped me get an internship the next summer at Microsoft where I was tasked with automating vulnerability discovery on Bing.com. It was a weird summer in Bellevue, WA. The following summer I spent in San Francisco at Mozilla building process-sandboxing into Firefox (with mixed success).

Towards the end of my undergraduate degree I began working part-time at Redstar Ventures which incubated a number of companies. I got to work on one of the early-stage products. All the while during college I also worked on side projects with my classmates, TA'd for Machine Structure and Assembly Language and Programming Languages, and started the Tufts Hackathon. A constant figure in all of these pursuits was Alden Keefe Sampson, another Computer Science student in my graduating class.

As graduation neared, Alden, who had previously interned at a small Boston-area company called Crashlytics, urged me to apply to work there. At the time they were 15-20 people and quickly becoming the defacto mobile developer platform. I got the job, somehow, right before the company got acquired by Twitter. I was lucky to build relationships some incredible mentors in my time there - Matt, Fiona, Jeremy and Rich to name a few. At some point, the big company culture of Twitter became inescapable and the pace and energy waned. Politics and posturing began to seep into product decisions, so I decided it was time to find something that rekindled the pace of learning I found when I first joined the team.

Somehow, I ended up in the Cambridge office of Elias Torres. Elias, the current VP of Engineering of Hubspot, was about to leave with David Cancel, the VP of Product, to start a new company. They weren't sure what the company would be, but they were starting to assemble the team and "hey, let's see if you have what it takes."

For a few months, I resembled a fictional silicon valley bro (which, you'll just have to take my word or peruse the rest of the site, I am very not). I did three things:

1. Work during the day
2. Rock climb in the evening
3. Work on a project with Elias at night

Gosh, I remember even ending a date because I had to "get back to work." I'm sorry!

I had what in retrospect looks like endless energy to build build build. I'd finish work, exercise, get home to the apartment I shared with the aforementioned Alden, slap down a bag of cherries on my desk next to my laptop and get back to work. This continued until the time came to start the company and yes, it would appear I had what it took. A few months in we hired Alden and boom, the company was off to the races. We had no idea what we were going to build but we had plenty of money to build it.

The team (first called Driftt then Drift) grew quickly and we cranked out MVP after MVP. Consumer mobile apps, something that sort of felt like a social Dropbox, annotation tools, and finally B2B marketing tech. By the time it became clear the latter was going to be the direction of the company, there were dozens of employees housed in a large office in Cambridge. I had a challenging revelation: for me to truly take my craft to the next level, I realized, it had to be something that I believed deeply needed to exist. And marketing tech -- I will not dunk on it if it is your passion -- does not speak to me. What could I work on, I wondered, where I would be proud to explain it at a party, on a date, to my parents?

In 2017 Alden and I left Drift to start {Upstream Tech}.