Reverse Resume

Inspired by Dave Cahill’s post on his Reverse Resume I thought it was an interesting time to reflect on my own journey. I particularly like that it helps to capture the non-linear and unique experiences that are often omitted in one’s journey.

So here we go —

I grew up poor. Life was full of scarcity. I knew I wanted to remove that scarcity from life, and the only path I knew out was to become a Medical Doctor, so I pursued a dual degree in Virology and Biochemistry. Then two crazy things happened:

  1. I met a medical student told me it would cost ~$500K in additional tuition/expenses, and I would be roughly 30 before I started practicing medicine.

  2. The financial world collapsed, which destroyed my ability to work and save up for this overwhelming financial and time commitment.

My one saving grace, I was good at writing software. So I loaded up on coursework and graduated early, while simultaneously landing a Bioinformatics internship at amongst the top Medical Center in the state. Turns out, software engineering pays way more than computational Genomics research.

Shortly after the collapse of Bear Stearns and a ~50% decline in the stock market, I was lucky enough to get my first job out of college as the second engineer at a startup building software for municipalities, paramedics, and firefighters. This was amongst the most humbling experiences of my professional career. Every bug is impactful, not just because of the lost revenue but because there’s a First Responder on the other end, for which frustration manifests as a distraction from preventing loss of life/property.

When the iPhone came out in 2007, our team was absolutely floored. I distinctly remember walking into my CTOs office, and we instantly knew we had to figure out how to scale the system to the iPhone and make it available more broadly. Porting our software to Objective-C was simultaneously fun and incredibly frustrating…and then serendipitously I discovered Xamarin. For me, it was more than just a developer tool, it was a community of the quirkiest runtime engineers and open-source enthusiasts working to make a delightful developer experience. I had found my tribe, racked up thousands of StackOverflow points, and gigabytes of IRC logs working with the community. What impressed me most as a young engineer — I would show up with a multi-threading issue and would be greeted with deeply helpful questions, and an enthusiastic curiosity about my experience.

It was incredible scaling out one of the first apps on iOS to thousands of Emergency First Responders, despite the many squeamish ambulance rides of user research. But the most fun was still engaging with developers in the Xamarin community to enable them to build amazing products.

In the Fall of 2011, Nat Friedman reached out to me and offered me a job…in San Francisco…in the Sales organization. As much as I admired Nat and wanted to work at Xamarin, I was terrified of moving from my hometown to an expensive city like San Francisco. More importantly, it was tough to shake my biases and preconceptions of a Sales role. Unsurprisingly, Nat is an incredibly charismatic entrepreneur and San Francisco was a super expensive city. I figured, worst case the cost of the flight back was $150, so I packed everything I had into two suitcases.

Being an early employee at venture backed startup is not easy. But when you’re passionate about the product and the customers, and you work with people who share a similar philosophy around impactful work, your brain becomes enamored with waking up to the daily challenges.

I was too naive at the time to recognize this — but I was working side-by-side with senior executives who were patient mentors to a young person beginning to reason about the world outside of his comfort zone. I learned to think critically, build passionately, listen intentionally, write effectively, navigate super complicated systems and relationships. I grew so much during this time, I barely recognized myself every year as I constantly evolved personally and professionally.

Almost exactly 4 years after moving to San Francisco, Microsoft acquired Xamarin. The oscillation between the joy of solving another problem and the feeling of exhaustion doesn’t go away when you get acquired, but there is a stillness. I was thankful for that stillness. It gave me the space for the rest of my life: my marriage, my health, my finances. Simultaneously, I had also moved across the Bay from San Francisco to Oakland. Just moving across the bridge, being exposed to a group of people outside of tech, made me acutely aware that “techno-maximalism” is an isolated phenomena. Technology is just a tool to empower people, to improve the experience of life in the universe.

However, the stillness didn’t last long. The transition was a cacophony of decisions: figuring out how to navigate a new role/culture, deciding whether the work was purposeful, and the politics in a large organization. These things were too foreign to me, and unlike others I didn’t have a bearing on my “philosophy for living.” My work had consumed most of my energy. Ultimately, I renewed focus on the one thing I knew worked for me: solving problems for customers. There is incredible purpose in making others successful, empowering them to achieve their goals.

In my time at Microsoft I have racked up more time in planes and hotels than I had ever imagined possible. But the ability to learn from such a diverse set of people has been a gift. There’s so much more behind every person and organization that simply requires meeting them where they are.

Just like clockwork, almost exactly 4 years after the Xamarin acquisition, my life changed again — 

I often joke — being a father is the most important “software” I will ever contribute to the world. It is invigorating to watch the world through our daughter’s eyes. It challenged me to think about my purpose, the skill I want to cultivate, my philosophy of life. And professionally, and how I leverage the investment in my work to enrich the world and improve the quality of the human experience.

Shortly after having our daughter, COVID-19 spread around the world. I started investing more in my work to help people organizations cope with the needs of a brave new world. I’m proud of what we’ve accomplished in just the last 6 months. I’ve also learned to say, “No” more often. And be confident that how I prioritize my time/impact may be incongruous with others expectations. Earlier in my career, it would’ve been hard to be so disciplined. But even if some of those “No’s” end up being mistakes, that’s good:

“Some mistakes will be made along the way. That’s good. Because some decisions are being made along the way. We’ll find the mistakes. We’ll fix them.”

— Steve Jobs at WWDC (1997)

I’ve learned some hard lessons this year, and simultaneously feel more gratitude and joy than ever.

In writing this, I’ve realized that the milestones in my journey don’t align to the roles or companies in my resume. But instead…to what I’ve learned, the ideas I’ve been exposed to, and the amazing people along the journey with me. This post is a celebration of those people and ideas.