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“Run a marathon.”

Those are the first words Nick Rellas, CEO and Founder of Drizly, says to me when we met back in July. At the time, Rellas was in the process of closing Drizly’s latest round of venture capital funding. Drizly is the technology company that is disrupting the shopping experience for beer, wine and liquor. After our meeting, Drizly announced that it raised a whopping $15 million series B funding round (the company has raised $33 million to-date).

But on this day, Nick is telling me to run a marathon.

Nick wasn’t trying to improve my physical fitness. He’s was giving me advice, entrepreneur to entrepreneur, all the while providing me with a sneak peek behind the curtain of what makes him successful. And frankly, a bit extreme.

“When I was in college I just got up one morning at 4 a.m. and ran a marathon,” said Nick. “You know, just to see if I could do it. When I finished my dad picked me up and I went to class.” He explained, “I mean, I’m a pragmatic person, I have limits, but I want to find them.”

He’s not kidding. Nick works in extremes. He’s been a committed vegan, an Ironman and he even went to art school to study photography before transferring to Boston College to become an analyst. See? Extremes. Nick suffered an injury that has kept him from marathons and Ironmans for a while, but he has leveraged his experience in intense fitness to run his on-demand alcohol delivery startup:

“My dad told me to think of it like an ironman,” said Nick. “Getting [a business] off the ground is the 2.4-mile swim because honestly, if an ironman were done in any other order you wouldn’t be able to do it. The swim requires your whole body and you get warmed up. That was Drizly’s  seed stage. Then comes the long grind. That’s the 112-mile bike ride. We’ve been on the bike for a long time because we are trying to grow this thing. Then you come to the last part, the marathon, it’s the hardest but if you can do it you’re at the other side. We aren’t there yet.”

[Oddly enough, Nick is both figuratively and literally on a bike. The CEO, along with four other Drizly colleagues, commute of choice is a moped that he rides throughout the city of Boston (weather permitting). That’s right, all of the images in this piece were taken on Nick’s actual moped.]

Drizly currently delivers to 25 markets in the United States and Canada and it employes 65 people, with 45 in its Boston headquarters. Still the company, launched in 2013, is relatively young for the impact it’s had on a heavily regulated industry. Nick remembers when Drizly was nothing but he and his co-founder Justin Robinson delivering alcohol to their friends.

“To get Drizly off the ground, we worked at a liquor store for a year,” said Nick. “We really didn’t have a choice because we were the drivers. We had one store that was willing to take a chance on our idea but the catch was that we had to actually do the delivery. At some point I remember realizing we had made an alcohol delivery app for our friends. I was driving up to the parties that I couldn’t go to with the alcohol and then driving back to the liquor store.”

Interestingly enough, starting a company in the liquor industry wasn’t something Nick wanted to share with his friends. He even went off of Facebook to avoid them. “Justin and I were embarrassed,” he said. “No one took us seriously. No one saw two guys bringing technology into a regulated world. They didn’t look at it as a 20 billion a year opportunity, they looked at it as two kids running around trying to sling booze to their friends.”

At age 25, both Nick and Justin were named to the Forbes 30 Under 30 list.

But Nick doesn’t seem to care too much about that kind of recognition. He prefers the wins that we as outsiders don’t see, like:


  •      When Drizly figured out how to effectively onboard a retailer;
  •      When they received approval from the wine and spirits wholesalers;
  •      Big hires that proved they were on to something big;
  •      Evolving Drizly’s consumer experience so that shoppers can price shop across stores, etc.

“These are the wins people don’t see and that’s okay,” said Nick. “All people see is the first round of funding, the second round, the third, the city after city. The this and the that. No one sees the two years that you put in before. The years when you have no money, no funding, and you are making minimum wage.”

Those “swimming days,” as Nick referred to them, may be over for Drizly, but he keeps them close. “I think the most important and challenging thing as an entrepreneur is balancing confidence and self-awareness. You have to go forward with unwavering conviction towards what you think is right while holding a mirror out in front of you.”

Now we know what he’s really doing with that rear view mirror on that moped of his.

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