Partner Profile: Meet Watermill Group’s Dale Okonow
Providing internships to students interested in the private equity industry is an important part of the Watermill culture. Recently our intern Paul had the opportunity to sit down with Dale Okonow for an interview.
How did you get into private equity?
I went to law school and business school with the idea to practice law for a little bit. I always felt I needed to understand the role a lawyer played because legal is always involved in business. When you get into law, it can be challenging to transition into business, but I knew that’s what I wanted to do. The predecessor to Watermill was one of my large clients and they offered me a job originally as in house legal counsel, then eventually as CFO. One thing led to another, we started investing outside money and Watermill was born. It couldn’t have worked out better; I practiced law for 5 years and was able to use that background to transition into other things.
What is your favorite thing about Watermill?
The culture and the people. We always have a lot of fun. It’s a collegial group, very hard working. It’s not a culture where you must stay until a certain time, or you must stay until your boss leaves even if you don’t have anything you’re working on, but when we have a transaction, it’s all hands-on deck 24/7. I like the adrenaline of working on a deal and closing a deal. When that’s over you can relax a little and try to find the next one, which is nice, but I’m a transactions junkie.
What are you most excited about for Watermill in the coming years?
The private equity business is undergoing a huge transition. There’s lots of money chasing deals. The competition is becoming more and more challenging, but Watermill has always been able to find a way. We will always do a few deals a year and if we continue to have our strategic focus, stay true to our guns, and be patient, we will find a lot of opportunity in our particular niche. Watermill will never be a fast-growing firm, but we will be a very successful firm. We are not going to put out dollars for the sake of putting money to work, but rather invest in deals that we like, that make sense, and that will have a good return to our investors.
Just 10 years ago, the smart phone came out and it revolutionized the world. What’s the next game changing advancement?
Technology improves every single day. I can’t answer what the next thing will be, but I know it will be there. We always have to stay ahead of it. You can’t ignore technological advancements in what we do. When I look back to when we first started, there were typewriters, no cell phones. We sent things through fed-ex and not email. So much has changed in so little time. The hardest thing to do as an investor is anticipating what could hurt you from a technological point of view, even if it doesn’t exist or hasn’t been thought of yet. We have to be aware and think ahead of our time.
As an avid Boston sports fan. If you could pick one team to be on which would it be and why?
I would love to be on the Celtics because, first of all football scares me I don’t want all of those concussions, and second NBA basketball players are the greatest athletes ever, they are so incredible to watch. They run, jump, they are so athletic. Their hand eye coordination is unbelievable. I think playing in the NBA would be top notch, it would be a thrill. Baseball is fun, I would do that too, but as athletes, NBA basketball players can do it all. Lebron could be a tight end, he could be as good as Gronk, he could be a defensive end, he could be a linebacker, he could be anything. They’re just incredible athletes.

There are a few tokens of Watermill memorabilia throughout the office, including a framed $100 bill. What’s the story?
Well we had these interns here, before your time, and we gave them a project. We said, what’s the largest search engine in the world? Steve (Karol) goes, “its YouTube.” I say there’s no way its YouTube, its Google, everyone uses Google. You would say Google too right? How many people actually use YouTube as a search engine? So, I bet him $100 the largest search engine was Google and not YouTube. It was a big deal throughout the office. The interns came back, and what do you know, it was YouTube. I said go back that can’t be right. There’s no way, it can’t be YouTube, no way! It’s not possible, how is that possible! I lost the money, but I still think I’m right.