My Corner of the Web

Defying the Imposter Within: Embracing Discomfort and Growth on the Path to Leadership


I have many reasons to feel like the ultimate imposter.

I dropped out of high school because I was afraid of failing. I had recently failed Math. My teacher even came to my house to try to convince me to go and write the exam. I declined.

I knew a lot about computers because I always tried to get my video games to run faster. I reformatted and reinstalled my machine several times a month.

That led me to technical support.

While supporting, I started hacking together training guides using HTML/CSS/JavaScript. It saved agents time because they could open the resource on their computers instead of putting customers on hold.

I was more valuable in coding than answering phones.

That led me to web development.

I often read that front-end development was scripting, not "genuine" programming. This sentiment persisted even as browsers grew powerful.

Finally, my frustration with depending on others prompted me to take action, and I decided to learn Ruby on Rails.

It turned out it wasn't so different after all.

That led me to backend development.

I struggled with showing up on time. I liked to pick my hours (actually, that's not true. I was usually hungover). Finally, I realized it would be easier if I were the boss.

I had a side hustle freelance job making $6k per month. I told a friend I'd split it with him if he started a business with me.

So we did.

That led me to become an entrepreneur.

I spent years working for clients, building their products. It's funny; I stopped coming in late and started to realize the value of discipline.

My business was simple—fee-for-service software development. But we had no intellectual property. So we thought we could learn more if we had "skin in the game."

So we started Kera to help SaaS businesses increase user engagement.

That led me to venture-backed startups.

Our business failed before it took off. We struggled to balance product development, traction, and fundraising and ran out of runway. Yet, Autodesk, one of our clients, came to our rescue. They were building a web version of AutoCAD and decided to integrate our technology.

So we picked up and moved our family.

That led me to Silicon Valley.

But, the software engineers didn't champion us. I reported to the UX leadership and became the sole developer within that team - a circumstance that led to my isolation.

Despite this, we integrated our technology into AutoCAD 360 web. It was a terrible codebase, an acquired mishmash translated from C++ to Java and JavaScript. Throw in a sprinkle of outdated Angular.js, and you get the picture.

AutoCAD 360 lacked love and ownership.

I was a strong advocate of the web as an app platform. I was sad because the web project was failing. The company had invested significant resources into it. I heard whispers of a better way to architect it by leveraging the C++ source code of genuine AutoCAD.

As luck would have it, a reorganization caused the head of UX to take over the web initiative. She came to me for advice. I seized the opportunity. I used my little political capital to elevate these whispers into "the next generation" initiative.

That led me to lead 5+ teams across three continents.

It took years to rebuild the product. But we did it. It was a marvel. We launched the first large-scale Web Assembly product in the world. It debuted on stage at Google I/O in 2018.

Meanwhile, a friend was taking a new startup through YC and was looking for a technical cofounder. I knew nothing about AI, which was the startup's primary goal. I expressed my concerns, but he said it didn't matter. I'd learn on the job. I was getting good at doing that.

So I left Autodesk and moved my family back home to start Delphia.

That led me to lead an AI startup.

I started by reading the thesis of each of the PhDs on our team (7 of them). I learned a ton. Yet, we failed to bring an AI product to market for many reasons.

We pivoted to FinTech using AI as a differentiator. We had zero leadership at the company with experience in FinTech. So I went and found the Investment Advisers Act of 1940. I started reading yet again.

That led me to FinTech.

Within a few months, we built a competent team. Each day, my work stretched the boundaries of my comfort zone. Finally, despite the complexity and difficulty, we launched. We delivered a world-first. A Robo-advisor that featured active management backed by a quantitative model. Anyone could invest for as little as $100.

And then my world changed again.

At Autodesk, I used to joke that the only way I was lucky enough to work there was via an acquisition. I wouldn't have made it through the standard hiring process. This joke was my anxious way of expressing my feeling of being an imposter.

Yet, today, I'm not so sure. Instead, I'm starting to feel a genuine sense of competence.

My story isn't over.

Every day is a step out of my comfort zone, an opportunity to learn, grow, and defy the imposter within. From fearing high school failure to leading a pioneering FinTech startup. I've learned to embrace discomfort and see it as a gateway to competence. The journey continues, and with it, my evolution as a leader.

So embrace your challenges, keep learning, and you can defy your imposter.

Remember, in discomfort, there is growth.