From Pixels to People: How I’m Designing a New Chapter at Enjoy The Work

My career began at the crossroads of design and technology, when the internet was young and it felt like everything was possible. In the last two decades, I’ve been a designer, a manager, an executive. I’ve been a mentor, a coach, an advisor, an investor. I’ve founded multiple companies, had the privilege of speaking to people all over the world, and even hosted a podcast. I’ve been a vocal advocate for design leadership and the power of walking your own path.

When I look back, I can see that so much of my life has been about “doing” in order to prove my worth; this belief that I’m valuable because of the things I do, how I do them, having the right answer at the right time, etc. Along the way, I realized that BEING is what I’m most concerned with. I didn’t need to do more, I needed to trust myself, step into my own power, and lead. And in doing so, create an environment where others could do the same. 

After we sold Abstract at the beginning of 2022, I found myself wondering what I was going to do next. I had been angel investing for a while and often helped founders with Design and Product, Go-to-market, intros to VCs, tightening up their pitch, how to be effective leaders, etc. Deep down, I thought it would be amazing to be a VC who had been through the founder journey and could really support CEOs from that perspective. So I joined the team at EQT Ventures and got to see what it was like on the “other side of the table.” I learned a lot from some very talented folks (h/t to Ali Mitchell, Laura Yao); and I also learned that late-stage investing was less about supporting the founders in the way I wanted to than I had imagined—which makes sense in retrospect!

During this time, I would often get off a Zoom call with a founder I was helping and my wife would say, “You know… you are always so full of life when you have these calls. Maybe that’s a signal worth paying attention to?” And as usual, she was right! 

So I started to look for the things that truly brought me joy, gave me energy, and felt authentic. This reminded me that people and connection are at the center of who I am. Being a safe space for people to have vulnerable conversations and deepen their own compassion and conviction. Yes, companies can be giant hairballs, but it’s the beautifully complex, ambitious humans that are making impossible things happen every day. These are the people I want to connect with—the people that believe that we can operate with candor and vulnerability, make space for each other’s gifts, and learn from our mistakes. 

Every startup founder faces the daunting challenge of transforming a promising idea into a sustainable business, and if they’re lucky, an enduring company. This kind of evolution demands both strategic acumen and intense personal growth—areas where many founders find themselves struggling alone. Having navigated these waters as a founder, an operator, an investor and an advisor, I deeply understand this journey and believe that it doesn’t have to be lonely or filled with anxiety. And I could not be more excited to bring all of that hard earned experience into my next professional chapter at Enjoy The Work.

So why Enjoy The Work?

I mean, aside from a great name and an awesome mission, it was this group of incredible people who are some of the most genuine, open, and insightful people I’ve met in a long time. I was reminded how important it is to find people that we can learn from and grow with. And this group of partners obsesses over teaching, coaching, and mentoring founders across both the soft and hard skills needed to become a truly great CEO. This intersection is where I continue to find myself and where I believe I can help others “enjoy the work.” 

Setting out to build a successful venture-backed business is one of the bravest and most foolish things you can do. You have to believe things that no one else does, have the energy and fortitude to will something into existence—all while projecting unwavering confidence. You must eat ambiguity for breakfast, be comfortable with not ever having enough information, and be self-aware enough to ask for help when you need it. It’s definitely not for the faint of heart. And I know firsthand that having the right support at the right time can make all the difference—to the business and to the founder! 

When I look back, I am grateful for the totality of my experience—all of it: the ups- and- downs, the successes and the mistakes. Every part of me was pushed to the edge. This is the hero’s journey that every founder embarks upon. An often lonely path that will test your character, push you beyond your comfort zone, require you to get up again and again and again, dust yourself off and ask, “What can I learn from this?” If you can adopt this mindset and surround yourself with those that can help you see the things you might not be able to see, this path can lead to profound personal growth and professional success. 

There were a few people along the way that had a huge impact on me as a CEO. One of them was Doug Knopper, CEO of Freewheel, who helped me to embrace the role as a massive learning opportunity. Aileen Lee, who led our Seed round, and impressed on me the importance of operational rigor. We behaved like the kind of company that we wanted to be and it paid off. As I begin my journey with Enjoy The Work, I am excited to extend these lessons and more to the founders with whom I’ll work. 

I’ve always tried to make myself available to founders who could use some help, so if any of this resonates and you’d like to talk, reach out anytime! 

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