An Opportunity Too Good to Pass Up

Why I’m joining startup advisory firm, Enjoy The Work

I grew up playing soccer. It was an everywhere activity, I loved it — soccer balls scattered the house, every wall was a new surface to practice the perfect pass or goal.

One sunny day at practice, my coach shared a framework that I will never forget and have always carried forward. He said his job was comprised of three core elements, and that he would take care of each of them:

1. He would remove the tedious items so I could focus on my craft and skills
2. He would show me how to build good habits, and
3. He would also show (not tell) the players why they need those good habits.

Intuitively, even at the moment, it just made sense to me and, later, as my career progressed I often thought about those learnings.

Today I’m joining the startup advisory firm, Enjoy The Work, and those words from that soccer coach remain an orienting premise.

About Me

A bit about me: over the last 20 years, I’ve founded and successfully exited three venture-backed startups. First was Qloud, a B2C on-demand music streaming service that grew to over 10M monthly unique visitors. Next was Kapost, a B2B SaaS company that we grew to over $12M in revenue and 100+ employees. My most recent was Onward, a ride-sharing service for seniors that was acquired this past summer.

Alongside the startup efforts, I experienced hyper-growth at Airbnb. From 2015 to 2019, I served as Head of Product for Airbnb for Work and Airbnb Luxe. While there, the company grew from 500 people to over 9000 and we grew our department’s bookings from zero to over $2B.

Although each company created value in unique, and interesting ways, I realized that many of the business tactics stayed consistent. These tactics included hiring and empowering a high-functioning team, finding product-market fit, shipping quality products, experimenting on go-to-market strategies, refining a sales motion, raising capital, etc. Looking back now, the tactics and practical anecdotes I’ve learned as both a startup founder and product specialist amount to a knowledge base that is surprisingly wide.

So, Why Enjoy The Work?

As I thought about my next chapter, I was brought back to the words from that soccer coach. Ultimately I wanted to move off the playing field so I can help impact others as he had done with me.

Just as that coach had made me understand how to get better by removing the unnecessary distractions, codifying good habits, and educating me on how the game works, I too want to pay these behaviors forward and do the same for the next generation of players/founders.

Additionally, to do anything great it is always better to do it with a great team. Collaboration with awesome, thoughtful, and dedicated teammates only makes you stronger, the game more fun, and victory more likely (shoutout to the Dartmouth soccer team that was top 25 in the country for 2 years).

I found teammates like this at ETW. I’ve worked with advisors and been one before, and it was clear that ETW almost doesn’t belong in the “advisory” category. Their approach is an entirely different take on founder and CEO support, in all the right ways, and the quality of each partner is top-notch. Every interaction with them enlightening and high quality.

I’m looking forward to getting into the trenches with the CEO’s and founders of the Enjoy The Work community, and working together to bring their innovation into the world.