Why Me?

I’ve been working in business for more than 30 years. Over that time, I have built a lot of businesses and launched a lot of products.

I started my first company at the age of 17. I was supposed to be in High School but that wasn’t working out for me.

I moved to New York City, as one does. I worked on Wall Street for a while. Later, I got a job in a Madison Avenue advertising agency. I enjoyed being around creative people and working in client service, and I stuck around those kinds of places for a long time.

I became a manager for the first time around the age of 24 when I joined a product design firm that had merged a web agency with a motion graphics studio. It was a dodgy outfit, for sure. I became CTO of that company and before long I was leading multi-million dollar projects.

I was a little terrified. The people who I worked with at this company were the most talented I have ever met. Looking back, I think we were all suffering from impostor syndrome. I can confess this now — nobody was faking it more than me.

Over ten or so years we grew Schematic to over 400 people. We made a lot of mistakes. WPP bought the company and it became their flagship digital arm. In my client service career I worked on over 1,000 engagements for the web, mobile and other digital platforms. At its height I was leading a team of around 100 people, resonsible for double-digit quarterly revenue growth, and personally managing a book of business over $10MM.

I eventually left and in 2011, I joined a tiny startup called Typekit. It was almost immediately acquired by Adobe. This was right at the birth of Creative Cloud. It was a very exciting experience to help build our tiny SAAS software into a business with hundreds of millions in ARR.

Adobe concentrated its typographic teams under the Typekit leaders. I became General Manager of the combined team of about 50. I was with this team for a little less than a decade as it evolved from a startup to a corporate center of cloud excellence. I built millions of revenue around these products and I learned a lot about enterprise sales during this time.

As General Manager, I was responsible for all Adobe font products and technology. I left Adobe in 2019 to start Business Letters and the Safe @ Work community. Since then I’ve split my time between coaching, writing, and some product and people management jobs.

From 2021 to 2022 I led a product management team at FreshBooks. In 2022 I became a senior product leader for Amazon, where I led a product management team. I left Amazon in 2023 and became CEO of Type Network. In 2024 I left TN and am now coaching and consulting full time.

The most important lesson that I’ve learned in my travels is this: The essential characteristic of a great leader is the desire to improve.