Partner Chris Ahn sat down in our Los Angeles office with Proskauer alum Doug Bouton, founder and CEO at GATSBY Chocolate and co-founder of Halo Top Ice Cream. Connecting around the bond they formed while working together in the Firm’s Corporate Department, Chris and Doug discuss their shared passions for living purpose-driven lives and embodying innovation and entrepreneurship wherever you are. The following Q&A is an excerpt from their full conversation. 

Chris: You started at Proskauer in 2009. What was your experience like as a summer associate at that time?

Doug: In ‘09 it was the thick of the financial crisis so rather than having big, glitzy events, our class had intimate dinners and softball games. Not only was it really fun but it also seemed to bring us closer together, allowing us to develop real relationships. We genuinely became friends and we would always go to happy hours and hang out after. It was a really, really tightknit class and we are still very close.

Chris: You have talked to me about knowing you wanted to pursue another path quite early on in your career. Tell us a bit about what it was like take a leap from law into business and your adventure into launching Halo Top.

Doug: While I loved my time at Proskauer and the collaboration I felt with my teammates, including you of course, I did know pretty quickly that I wanted to start my own business. After two years at Proskauer I decided to give my notice and take another chance, and the Halo Top idea was presented to me by my now former business partner Justin Woolverton, who’s the founder of Halo Top. Looking back, I quite naively thought it was going to be easy and like the best thing since sliced bread and we’re going to be millionaires and this is great. And then reality hits you really quickly that that’s not how the start-up world works. But there was a ton of excitement in that period of the next chapter and what are we going to do.

Chris: What do you think you learned at Proskauer that you’re applying today?

Doug: Whatever you want to do in life you still have to work your tail off at it and you have to show up every day and you have to be consistent. I learned about attention to detail, critical thinking; and how to manage people. It was really formative in terms of how I want to lead and not micromanage but also, demand responsibility and accountability in kind of this really productive way. You can come to Proskauer and develop these skills and then take them whether it’s going in-house, whether it’s going into business, or whether it’s staying at the Firm and becoming the best you can be.

Chris: And that all touches on the principles of entrepreneurship. What are some of the ways that you keep yourself motivated and your energy and spirits high?

Doug: It can be hard. We’re all human and I think it can be a grind, like anything. I heard a quote the other day that basically said, I’m slightly smarter than those who won’t grind as hard as I will and I’ll grind harder than those who are smarter than me; that’s my sweet spot! I don’t really care what I’ve done. I really think it’s about what you’re going to do. So I talk about Halo Top. I know that’s what people want to hear about, I know I wouldn’t be invited back here or anywhere else if Halo Top didn’t sell or become what it became. But I truly have moved on from that. I want Gatsby to be successful. If this isn’t successful I want it to be the next thing. I think you have to earn respect every day and it’s not about what you’ve done, it’s about what you’ll do.

Chris: What’s your process when confronted with a problem or a challenge that you don’t know how to solve?

Doug: You can use the tenets of what I would call entrepreneurial thinking in whatever you’re doing whether it’s law, business, making a cup of coffee, I don’t care. One of the foundational tenets for me is thinking outside the box. I focus on how to find the edges of the box, so that I also know how to stay outside of that. And that’s not to say you throw everything out that’s inside the box because a lot of it’s there, it works and is there for a good reason so don’t throw the baby out with the bathwater but if you’re not outside of the box I don’t think you’ll be able to see the opportunities and what may seem impossible to other people will seem very possible to you. And I think that outside-the-box thinking, particularly being able to recognize when you are just kind of doing what conventional wisdom says you should do without questioning should I still be doing that, is critical.

Chris: What are some things that you try to do to balance your responsibilities at home versus at work?

Doug: It’s a great question. I got this wrong in a big way when I first launched Halo Top. I got married and had two kids right at the same time the business was taking off. So I had this crazy business ride, I was flying around the world with a wife and two kids at home. And even when I was home I wasn’t present, and I was exhausted. I didn’t hold up my end of the bargain there. Second time around here with Halo Top International and Gatsby and anything else that we do, it’s just making sure I prioritize my family. If I say that’s my priority then the actions have to follow it, and they will. But I didn’t get that right. I learned that one the hard way and it was really, tough on the family, on our marriage. For anybody who becomes a partner or who has success in business…behind that person I assure you there is a spouse and a partner who probably is not getting nearly enough credit, recognition, or love that they should because it’s hard.

Chris: So the last question is for those just starting their professional careers, at least in the law, what advice do you have for them?

Doug: If you want to be a lawyer you’re obviously in the right place. You have a lot of fantastic people here at Proskauer. But if you don’t or, you know, 10 years from now don’t see yourself practicing law or being a partner at a big law firm you can still develop incredible relationships here, develop incredible skills that will just help in whatever you want to end up doing.