Thank you, Dwolla

So… this past week was my last at Dwolla. After over 2 and half years, it’s hard to wrap my head around the fact that it’s over. It’s starting to sink in, so I figured I’d write about it.

Dwolla retreat, summer 2014

The beginning

Dwolla has been a family to me. I joined as an intern when I was 17 at the beginning of my senior year of high school. Totally on a whim, too. A school assignment whose aim was to prepare students for the professional world had me search for an internship. They wanted you to write a resume and cover letter but they didn’t want you to actually apply. They wanted you to pretend. I thought that was a bit silly, to have you go through all that trouble and not actually go for it when you’ve already the necessary work and you just need to hit send.

What caught my eye about Dwolla’s job posting was the way the application was to be submitted. Instead of filling out a form, Michael Schonfeld, the founding Developer Evangelist, asked the interested reader to create a HTTP POST request with their name, email, resume, and other info, all encoded in JSON to a toy API he set up. It was this early on when I caught a glimpse of the creativity which marks his distinct personality.

After our initial interview, it took a while to actually get hired. There were some concerns about hiring a minor, since I couldn’t legally be bound by the contracts I’d sign to join. Michael fought through to make it happen — so really, I owe to him the two and a half years at Dwolla that followed.

Michael and I, dressed as “evangelists” for Halloween

It brings me back to remember that when I started, I couldn’t work more than 30 hours, which was the maximum number of hours a minor can work per New York state law. After about 3 months, I finally turned 18 and immediately started working full-time hours. I also barely graduated from high school. I say barely because I cared more for work than school, and my grades showed it. Working was an ecstasy. It was a creative outlet which rewarded me not only with some money but a steady feeling of fulfillment. It gave me purpose.

Life on the road

A few months later, I was offered a full time position as a Developer Evangelist. I gladly accepted. My freshman year had just started at Hunter College. Working full time while going to school full time didn’t sound like too big of a challenge at the time, since I was sort of already working in high school. But this job wasn’t just about working in an office — Developer Evangelism inherently requires travel. Some evangelists travel more than others, but it’s fair to say that the majority will fly at least a dozen times a year. I hadn’t been on a plane since I was 7, so the thrill of traveling to new places was intoxicating.

SOHacks, 2014

While also going to classes full-time, I spent the next 12 months traveling on the weekends to hackathons and conferences to help developers build awesome things with Dwolla. I had the chance to brainstorm with hackers as they do their thing at some of my favorite hackathons: HackMizzou (Columbia, MI), HackTX (Austin, TX), TartanHacks (Pittsburgh, PA), HSHacks (San Jose, CA), SOHacks (San Antonio, TX), HackIllinois (Urbana-Champaign, IL), Code Day (Minneapolis, MN), PennApps (Philadelphia, PA), MHacks (Detroit, MI), Compute Midwest (Kansas City, MI), and HackUpstate (Syracuse, NY). In 2013 and 2014, I travelled about 57,000 mi in total. Not a lot when stacked against others but quite a bit for an 18/19 year old!

Along the way, I met so many fascinating people including a handful I’m proud to call friends. One of them, Ben Sammons, I met at HackMizzou in Columbia, Missouri. It’s because we met that he ended up working at Dwolla. A year later, while we hung out in my hotel room in Des Moines, he told me about his Uber ride to the airport earlier that day which he shared with a sales person at a company called Greenhouse. That was the first I’d heard of Greenhouse. Months later it ends up that Greenhouse is the company I’ve decided to join next. Life is funny sometimes.

The HackMizzou squad at HackIllinois, 2014. Ben Sammons is in the center.

Some months, I spent 3 weekends on the road. A lot of folks were astounded that I could juggle full time work and school and this travel. It was difficult, but the first 3 semesters weren’t very challenging… I simply did the bare minimum in school, just enough to get by. Considering I was working full time in an industry that is questioning the importance of formal education, it was difficult to feel motivated to try hard in school. Besides, the core requirement courses (English, Pre-Calculus, etc.) are usually interesting but that’s about it — there’s nothing to think too deeply about. This strategy of winging it would prove to be an awful one once I started taking classes that weren’t simply intro classes.

Personal growth

Dwolla gave me the opportunity to do things that were outside of my comfort zone. Having made many mistakes and a number of successes, I’ve identified some of my strengths and weaknesses. I learned some of those things you shouldn’t do, and some that you should do. I learned how much I enjoy working with other people, and how good it feels to enable someone else to do something they didn’t think they could do. Instead of just reading about it in books, I’ve seen first hand why it’s important to develop your character, and to keep a constant eye on it because you’re never done improving. I’ve learned how important it is to show enthusiasm and to give praise when it’s due.

It’s the interactions I’ve had at work that’ve shown me the value of compassion and taught me to try to see problems from another person’s lens. In these two years of early adulthood, I grew not only as a professional, but it’s through these experiences that I’ve learned what I’ve learned so far about being an adult.

Over the past year, I’ve had the great privilege to build a solid team around Developer Relations at Dwolla with Brent Baker. I can’t even begin to describe the amount of knowledge I’ve come away with working with Brent. As a first time manager, I learned that management is no easy task. You only get better with time and experience. Yet the role comes with a deluge of responsibility which can be disastrous for the unprepared. I’m glad that Brent was there to provide soothing wisdom, guidance, and support, as he does. When asked to name a role model, I’d say Brent without a doubt. I’ve even considered printing WWBD (What Would Brent Do) stickers for my laptop.

I’ve had some great experiences living and working with the people at Dwolla. Here are a few things I did for the first time ever with them:

  1. Roasted smores at a campfire
  2. Drove a car
  3. Worked a dishwasher
  4. Rowed a canoe
  5. Went on a loooong road trip
  6. Fired a gun (it was a shotgun)
  7. Went on a 350mi road trip
  8. Played yard games like ladder golf
  9. Spoke on a panel
  10. Wielded a sword

Leaving: distance makes the heart grow fonder

One thing that took me a while to realize is that leaving is just another important learning experience.

As you’d expect, leaving is an emotional challenge. I didn’t think it would be easy when I was thinking of leaving, and it certainly wasn’t, and continues to be difficult. It breaks my heart to read the stream of replies to my departure letter, many of them were heartwarming, honest, and filled with kind words and wisdom. Reading how much I would be missed made me want to turn back and stay. The other night I read through the cards I got at my one and two year anniversaries, and the feels struck. It’s funny how you really don’t know how much you value someone until they say goodbye.

I’ll never forget how proud I felt of our team when we launched our new developer portal, my final project, after staying up nearly till the morning in a blitz campaign to squash last minute bugs. It reminded me how great the team I was leaving behind was, and I felt regret clawing viciously at me.

That said, I think distance can be good. Without the anxious anticipation of the future, leaving lets me revisit decisions I made during my time at Dwolla and analyze them with the new perspective and patience of hindsight.

Looking back, my transition was a great experience. I’m glad to have done it because it’s left me with even more respect for the folks at Dwolla.

Why’d you leave? And where are you off to now?

Most folks in developer relations have spent many years in a previous life in software development. But I started the other way around. And I can’t help but feel that what’s missing is engineering experience. Deep down inside, I love to code. I love finding creative approaches to hard problems. The promise of fulfilling these desires is what draws me to an engineering role.

In a little over a week, I’ll be starting a full time engineering role at Greenhouse. And, I’ll continue to pursue my degree in computer science part time. I’m incredibly excited.


At Dwolla, I made lifelong friends. I discovered a lot of things about myself. All around, I’m lucky to have so many great memories.

It would have been impossible to predict two years ago where I’d be today. I can’t think of any company where I could have had an experience that was remotely similar. I thank my family at Dwolla and I marvel at the unlikely odds of the circumstances which aligned to lead me here. One thing’s for sure — Dwolla has set the bar high for my future endeavors.

My time at Dwolla has prepared me for life in a way that nothing else could have. And for that rare gift, I am eternally grateful. Thank you, Dwolla. And farewell.

My favorite shot of Des Moines, my second home