[Driven] Aaron Jun: This Humble Risk Taker May Be Boston's Next "It" Entrepreneur banner image

[Driven] Aaron Jun: This Humble Risk Taker May Be Boston's Next "It" Entrepreneur

This post appears as part of our Driven profile series, spotlighting some of the hottest movers and shakers from all corners of the Boston tech and startup space.

Aaron Jun has the makings of everyone’s favorite kind of success story. The plot line? Smart, motivated South Korean immigrates to the U.S. as a kid. Grows up in California with Apple headquarters for a neighbor, moves to Boston with nothing but a few pieces of luggage and a guitar. Secures a successful career early on. Gives it all up to launch a company of his own.

There’s more to Jun than that, though. Most notably, he’s exceptionally self-aware and humble, with the tendency to take the kind of risks others would balk at.

Playing it safe

Aaron Jun immigrated to the U.S. from South Korea in 1994 at 8 years old. He spent the rest of his childhood in Silicon Valley - Cupertino, to be exact - right in the shadow of Apple headquarters.

But unlike today, as a child Jun avoided risk at all costs.

“I think it had to do with my immigrant experience,” he reflects. “I barely spoke English when I got here. I had a year of ESL [English as a Second Language] classes, then they put me right into the mainstream.”

He says it was traumatic and recalls a time when he had to read out loud in class. He still had a thick accent and was learning the idiosyncrasies of English. He read word island as “izz-land,” and the class erupted into laughter.

“I got trigger shy,” Jun says, and after that opted to play it safe.

He attended the University of Southern California, initially entering as an English major with aspirations to become the next great American novelist. After seeing the first tuition bill, though, he changed majors to finance. The safe bet. (In an ironic turn of events, the economy was shot when he graduated in 2009 and “the safe bet was a very weird place to be,” he says.)

After a couple of quick stints on the West Coast post-grad, a buddy referred Jun to Boston startup Fiksu, where he landed a job as client development manager. With just one friend here in Boston, Jun packed his life into two bags, grabbed his guitar, and hopped a plane to Logan.

It was then that his track record as a risk taker kicked off.

“At some point on that plane ride, I realized whatever it was I thought I had to be afraid was a fabrication - non existent,” Jun says.“Basically everything I ever said I couldn’t do was so false.

“The moment I decided not to play by those rules, I could do a lot of things I never thought possible,” he adds.

Mind over matter (& marathon)

Moving to Boston wasn’t the only thing that changed Jun’s outlook. He also credits the shift to running. He took up the sport on what seems like a whim. After finishing a handful of half marathons, he decided it was time to go big or go home and in 2014 ran the Boston Marathon.

Unironically, it’s distance running that showed Jun what he was really made of.

“I realized what I always felt in the past wasn’t fear,” he explains. “It was a reaction that happens when you’re close to the edge. It’s like when you’re at mile 22 in a marathon. Your body tells you, ‘Stop and rest. No one will care if you stop.’ But in reality, you’re not going to die.

“When your mind tells you to back off, you still have 25 percent left,” he adds. “But your body doesn’t want to tap into that. Just tell yourself no. Keep going. You’ll be fine, your mind will accept it, the fear will go away, and you’ll move on to the next milestone”

Out & back

After over two years at Fiksu, Jun received an email from one of the company’s execs (the two had bonded over karaoke at the Hong Kong some months earlier) about an opportunity to serve as director of client management in Fiksu’s London office. Another location he’d never visited and where he knew next to no one, Jun jumped at the chance. He packed up the same two bags and guitar he’d come to Boston with and jetted off to the UK.

Twelve months later, he was back in the Hub - this time working for Jana as senior account manager. But he quickly found himself itching for more.

“At the core of it all was this inclination to make something,” Jun says, referencing his old dream of writing a novel. “I wanted to build something from nothing, and see what happens, and see what I could do.

“When I made the decision [to start Gatsby Social], it felt like something I had ignored or put off for years. So when I decided to do it, it was natural,” he added.

Party with Gatsby 

In December, Jun jumped head-first into his startup Gatsby Social, an on-demand concierge service that aims to make discovery easier by helping couples find new things to try and places to check out. The company launched early last month and has seen its user base grow 60 percent week over week since then.

Let’s say you and your significant other are looking for a place to eat on Friday night. You turn to Yelp - but the number of options are overwhelming and so many of the rankings and reviews are based on bad experiences. You play the “I don’t know, where do you want to go?” game for a while. Eventually, you’re both so hungry, annoyed, or both that you throw in the towel and head to the same spot you eat every other Friday night. Gatsby aims to eliminate all that.

As Jun so accurately puts it, “I think what people really want is for there to be a limit on their options, so the tyranny of choices is removed from their lives. So they don’t need to spend an hour to figure out what to do on Friday.”

Couples categorize their identities into buckets like “outdoorsy hipsters” or “adventurous foodies” and select their preferred neighborhoods. They then text what they’re looking for to the app - whether that’s a restaurant for date night or something new to do on Sunday afternoon - and Gatsby uses “foodies and computers and algorithms and hipsters” to curate a list of option based on that couple’s identifiers within minutes. Just like the curation algorithms behind Spotify, the more a couple uses Gatsby, the smarter the suggestions become.

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“We're basically trying to build the simplest, most conversational recommendation app out there,” says Jun. “And our goal is to find our users something perfect to do in less time than it takes to microwave leftovers for another night of Netflix.”

Next week, Gatsby opens up for beta testing, and anyone - whether in a relationship or flying solo - can sign up to access it. Along with prepping for beta testing, Jun and his team have been building relationships with key players in the Boston hospitality industry, like Citizen Public House in Fenway and Trina's Starlite Lounge in Cambridge. The plan is to team up with these partners for exclusive Gatsby user events, like cocktail classes and tastings.

Digging in 

As co-founder and CEO of Gatsby Social, Jun’s not afraid to get his hands dirty. In fact, at the start he was hand curating suggestions to pass along to couples. For example, around Valentine’s Day one user texted in about looking for a “luxurious vegan recipe.” A pretty broad request for sure, but fortunately Jun had just made a vegan risotto the week before and was immediately able to share his recipe.

Another time, a couple texted Gatsby looking for a spa to visit while in Vermont. That kind of request is a bit outside of Gatsby’s typical scope, but not wanting to disappoint or discourage early users, Jun took a few hours to do some digging and passed along suggestions to the couple. Talk about personalization.

Try to point out Jun’s humility, though, and he’s quick to dismiss it.

“Moving to America stripped any arrogance away,” he explains. “I stated Gatsby and those last bits of arrogance were gone. It’s funny how quickly ego gets stripped away.

“It’s a good exercise,” he adds. “Most successful people remember what it was like to have nothing to their names except a belief or an ambition. They remember those who gave them a hand.”

Kaite Rosa is Director of Content & Marketing at VentureFizz. Follow her on Twitter: @KaiteRosa