Julia Shapiro, founder and CEO of Hire An Esquire sat down with Doug Bouton, President & COO of Halo Top Creamery, No. 5 on Inc.’s 2017 list of the fastest-growing private companies in the U.S.. Formerly an attorney on the Hire An Esquire network, Bouton tells us how he went from Biglaw to a big bet on ice cream, the kind of company he’s trying to build, and how other lawyers might break into startups.

JS: Thanks for talking to us, Doug! The last time we spoke you had just left a big law firm, Proskauer, and were trying to get your ice cream company off the ground. What made you decide to make the leap from Biglaw to entrepreneurship?

DB: It certainly wasn’t a straight line, but I think I knew the day I stepped into law school, I wasn’t interested in practicing law. I went to law school at UVA, which was a pretty social place, and there were a lot of aspects about the social life at UVA I did enjoy. But I never wanted to be a lawyer. Like a lot of us, I got caught up in the “Big Law” thing at law school and ended up accepting a position at a big law firm. Not surprisingly, as a young associate, I didn’t enjoy my job and knew very quickly that it wasn’t for me. So in those early days of my career, I was always asking myself: what’s next?

JS: So you worked at Proskauer, and left to make low-carb ice cream? How did that happen?

DB: For me, Halo Top happened by circumstance, actually; I was part of a pickup basketball league with some other lawyers in L.A. and that’s where I met my business partner, Justin [Woolverton]. About the time I was quitting, he told me that he had started a company and about the concept of Halo Top. It was getting to the point where he needed a partner to really help him get it going, and so it was the right time and the right place for me. I jumped at the opportunity, and we haven’t looked back.

JS: You worked with Hire An Esquire as a contract attorney after that. Were you doing contract work while you were trying to get Halo Top off the ground?

DB: Yes, exactly. Around the time I left Proskauer I actually started my own law firm—Bouton Legal—I didn’t have an office or any real overhead. Halo Top wasn’t making enough money for us to take a salary consistently, and even when we did, it definitely wasn’t enough to live on in Los Angeles. That’s where Hire An Esquire really came into play for me. It became an efficient way for me to get some billable hours whenever I needed them. I could turn the spigot on and off, as needed, so I could grab some hours of legal work for the weekend if I had time.

That was a lot more efficient for me than trying to drum up business on my own—all the networking, time and effort, travel, and facetime that takes. I was putting in 80-hour weeks at that point trying to get Halo Top off the ground, so I didn’t have time for business development when it came to legal work.

In fact, Hire An Esquire helped me find a solo attorney who already had business and clients, and she needed an associate for lower-level matters, so she started passing work off to me to do. I’m sure if you look back at my Hire An Esquire days, most of work was done for her. It was really very useful, a critically timely service that Hire An Esquire provided me.

JS: That’s interesting, we see this happen a lot—a lawyer breaks out on their own and quickly needs to connect with another lawyer for overflow work. In fact, our fastest-growing segment is law firms of 1-40 people who do exactly what you were doing.

DB: Well, I certainly didn’t do any research, and it kind of just fell in my lap—but it was very useful. It paid the bills, and I didn’t get evicted!

JS: So you worked with this one client primarily, but at some point Halo Top took off and you left the practice of law completely. What’s the story behind that?

DB: Halo Top really started to take off in 2016. We got two big PR hits early that year: one online feature in GQ and another in BuzzFeed. Both pieces were within weeks of each other, and it was the perfect time for us: we had just reformulated and rebranded Halo Top. We were in enough stores that when people read those pieces, they were able to go out and buy the product right away, which is important when you get good PR like that. That’s when it really started to snowball—revenue started doubling month over month. Justin and I were finally able to take salaries from the company, and we’ve been growing ever since.

JS: Have you noticed your legal training show up in your work now?

DB: Oh sure, in a few ways—the most concrete being when we first formed the company. The documents and contracts, the D/B/A, raising money for the company, drafting the operating agreement — those were all things I could do myself, and it saved us thousands in legal fees. We didn’t have the cash flow for those legal expenses, so that was a big benefit to us.

Also, the network that I built as a lawyer helped with seed money. We’re proud at Halo Top that we’ve never taken outside investment from a venture capital or private equity firm. All of our early investors were friends and family—including friends from my old law firm and friends from law school—and they had the disposable income to take a risk on our company.

Another thing about our background that’s served Justin and I well [editor’s note: Justin Woolverton is also a former attorney] is our ability to critically think about issues that come up in company. We question everything, especially conventional wisdom. It doesn’t matter where you sit on the org chart; we want to hear what you think, and the reasoning behind it. And if you don’t agree with something we’re doing, tell us why.

JS: That brings us to our next question: what kind of company are you trying to build at Halo Top?

DB: What we’re trying to build is a place where other entrepreneurs would want to come work. Whatever role we hire for, we want that person to be the CEO of that role. Nobody has time to micromanage, and we’re really looking for people who can wear multiple hats, think outside the box, and be willing to challenge conventional norms—just like entrepreneurs do. We want that spirit everywhere in this company, and we’re not afraid of it. We try to stay flexible and nimble and ask our employees what they think we should do differently. We want candid dialogue, not “yes-people.” And hopefully, through doing that, we come up with the right answers, solutions, or execute on the right strategies to move forward.

JS: What advice would you give to other attorneys who want to jump to entrepreneurship?

DB: Like I said, mine is the story of Justin and I meeting—meeting him was a lucky break for me. But if I was still an attorney, just starting from scratch and wanting to break into this area, I would focus a huge part of my practice around startup companies. I’d advise people about forming their companies, drafting those partnership or operating agreements, and raising money—do that, because inevitably these startups will be willing to take you on, if you show your value on not only the legal side, but the business side as well. You might start as an outside lawyer but that could quickly evolve into a relationship, a larger role, and you can find opportunities to get in at the ground stage with a lot of these companies.

One thing I will say: a lot of people romanticize startup life—I worry that happens quite a bit these days, so I want to manage expectations here. Startup life is hard. It’s not sexy. Things need to get done, and there’s nobody to do it but you. Just because you start something doesn’t mean you’ll be successful. Sure, we worked off our asses off, and I think the idea and concept behind Halo Top were great—but those weren’t necessarily enough to make us successful. We got to where we are because of a lot of lucky breaks, especially that free PR in early 2016. There was a lot we didn’t have control over and things that had to go our way to even be sitting here talking to you today.

I’d also tell people to figure out what stage of startup they’re comfortable in. There are so many different stages of startup companies that the word “startup” is almost meaningless now. Uber and Halo Top might both be considered startups but we’re obviously vastly different in terms of the stages we’re in. That initial “garage” stage is tough—it’s risky and you’re losing tons of money—not everyone has an appetite for that. You might want to work with a startup that’s a little more established, a more mature company, but still get a piece of the startup action. Just know what you’re comfortable with.

JS: Have you noticed any slowdown in the growth of sales as more low-calorie products enter the market? And what’s next for Halo Top?

DB: Well, no company can stay on the hockey stick curve forever, but I think as companies like ours mature, you start to focus more on the bottom line than the top one. Top line growth has somewhat stabilized for us within the grocery channel in the U.S., but there remain tons of opportunities in the U.S., including channels like the convenience store channel and launching new products. We’re also actively expanding in international markets which represents a huge growth opportunity for us. We’re really excited as we look towards the future and see a lot of opportunity.

JS: Last thing: can Halo Top send us a case of ice cream?

DB: [laughing] Sure, of course. Just let us know where to mail it.

Read more about the Halo Top story in Inc. or visit their website for more information.

---