Over Coffee

Sometimes people ask to hear my story. This is what I'd tell you over coffee.

I grew up in the U.S. Virgin Islands. My first real paycheck was as a dishwasher in my dad's restaurant when I was 12. $340 something. I bought a camera.

At 18 I walked into The Breakers of Palm Beach as a server. Eventually I got my first shot at leading. It wasn't perfect. I almost got fired. Twice. Learned hard lessons. Got a shot to build L'Escalier from the ground up and we won the AAA Five Diamond award with an incredible team.

The Breakers taught me that it's all about people. Build the team, give them the expectations, processes, voice, and care, and you will find that team has superpowers. I can still hear the click of the heat lamp as the chef turns it on. The glance from a teammate across the room. The almost indistinguishable nod to the table we needed to clear. The words that didn't need to be said. Some of my best friends to this day.

Two weeks after we invaded Iraq, at 26, I enlisted in the U.S. Army. 18X program. With a motto of De Oppresso Liber—free the oppressed—I was all in. A need to serve, a bit of an adventure deficit, and a romantic idea of war, and off I went. Green Beret. 18E communications sergeant. Four deployments to Iraq and Central Asia. I was incredibly lucky to work with amazing men and women. In Baghdad, Kurdistan, Tajikistan, Afghanistan. With people from every agency and a dozen countries. Relationships I'll never forget.

The army was an important time for me. I entered focused on me. I complained about the bureaucracy, the red tape, the food. One day driving through Baghdad, a buddy looked at me and said, "Dude, stop." He was right. I had a chow hall, a hot shower, and coffee every morning. This was combat. Not war. My grandad went to war. People were barely making it a few hundred meters away. There are usually worse things happening to better people.

That's where I came to truly understand this idea of we, not me. When we accept that we're really all just making it up as we go, you can check your ego. Humans. Strengths. Weaknesses. Hopes. Dreams. Together, cutting a path.

From that moment on it was clear to me that I must do things with people that matter to me and work on things that matter. Mission. With a team.

Brandi and I had three boys during those years. I loved the mission but I couldn't be a husband and a father and a Green Beret. Some guys can. I couldn't. I'd been mostly gone for five years.

I was in Tajikistan when my old AGM from L'Escalier called. He had a job for me—VP of Operations at BR Guest Hospitality in New York. Twenty-plus restaurants, three thousand people. I'd been out of the game for almost a decade. Now I was in arguably the most competitive restaurant market in the world. The pressure was real. The transition was so important to us as a family. Brandi reminds me of the PTSD. Small kids. Those times were tough. But I was so grateful for it. Learned so much. And very proud of that team.

Every role I've taken has come from a relationship. Even the army. My grandfather was a Colonel—WWII, Korea, Vietnam. Small farm in the Blue Ridge Mountains. Married 65 years. Grandkids running on green hills and eating tomatoes like apples. I think I'm just trying to be him when I grow up.

A close friend called me to leave BR Guest and come run the Boca Raton Resort & Club. Our families had always been close. A chance to do something together wasn't something Brandi and I could turn down. Hilton property, Blackstone portfolio company. Two hotels, 1,047 rooms.

It was there, 39 days in, sitting on my office floor. It was a Sunday. 67 projects on a whiteboard. The pressure hit me. I could feel my heart beating. I didn't want to let Rick down. I didn't want to let the team down. There was no way we could do all of this.

Then I said out loud: do what you can every day. If we get 1% better each day, it compounds. That's more than 3,600% better in a year. Calm, steady progress. That became Better Today Than Yesterday. That's how I try to run my life now. Just get a little better. And help others do the same if you can.

From there, Hilton asked me to move to Chicago to build and open the Conrad. I ran the Waldorf Astoria Chicago while we built it. Then came StuyTown.

We built a team and called ourselves Good Neighbors: Kind. Helpful. Thoughtful. Respectful. Providing homes for people was a mission we took very seriously. Very complex. If it happens in America, it happens in our communities. Build a team. Build a team. Build a team. That's what we did. We knew it was possible to do well and do good at the same time.

StuyTown is the largest rental community in the country. 11,241 apartments. A city. We turned it into Beam Living and grew it to 15,000 apartments across New York. In August 2020, middle of COVID, Blackstone asked me to also run LivCor, their national multifamily platform. CEO of both. Over the next four years we grew LivCor from 40,000 to 175,000 apartments. Much of it during COVID. We hired a CEO for Beam, acquired Preferred Apartment Communities, and hired a president for that. A lot of building.

My time with Blackstone, over 12 years, in the room with some of the smartest people I've ever worked with. And people that really cared about doing the right thing. We always tried to do the right thing. I'm not sure we always did. But we tried. For our guests, residents, and team.

An opportunity with an old friend came up that was a chance to run something global. Brandi and I decided to give it a shot. SafetyCulture was a company I'd been a customer of since 2012. A SaaS operational platform that helps frontline teams execute a standard and get better every day. These are the people that make the world work that most people don't remember. They make things, move things, and serve things. I love technology and building product. When you can enable humans with technology, they can do their best work. That was this chance.

The role was supposed to be President, based in the U.S. Two months before my start date the founder called and said he couldn't be CEO anymore. "It's yours."

Customers in 180+ countries. We had teams across APAC, EMEA, and North America. After a year on the road, 250,000 miles, and a platform that needed a full rebuild, it was obvious they needed a CEO in Sydney full time. That's where 500 of the 800 people are. We did that in the army and it wasn't something I would do again. My relationships at home will always be my priority. The team needed someone there every day. Hard decision, but easy decision. I'll miss the team and the mission.

Today we're in New York City. Princess Buttercup (Brandi), three kids (21, 19, 15), two dogs, a cat, and a turtle. I'm working on a few personal projects that I've always wanted to give time, adventuring with my cameras and humans, and trying to get a little better every day.

Maybe we should do something together.