Once again, brand-new college alums everywhere are grappling with the inevitable graduation-season question: What’s next? There's the obvious—"get a job"—but for some, working on a product or service that’s already established isn’t ultimately the right path, nor is it gratifying enough. I’m talking about the kind of people who have an idea—and a lot of conviction that it’s going to take off. The kind of people who want to be a part of creating something that could become really big down the line, but can still handle the very real possibility that it might never take off. Clearly, startup jobs are not for the kind of people who are looking for the easy or sure path.
Starting your own business comes with inherent risks, but for this handful of Boston entrepreneurs, it was perhaps the best decision they ever made. Here's their advice.
The truth is, Barry’s career began at a hedge fund in New York, where she was responsible for originating and executing high-return strategic investments. From there, she went onto become a project associate at Athenahealth. Now, though, she’s the founder and CEO of ZappRx—a digital health startup that she founded in 2013. The company’s prescription management system is aimed at simplifying and streamlining the way specialty medication is managed.
"Steady jobs are just that - steady,” she explained to BostInno. “That translates into monotonous, tedious and dull over the decades. Comparatively running a startup is an absolute roller coaster — the highs are epic and lows give you grit. I never realized how much I was capable of until I bolted from the corporate world and founded ZappRx. As a first time CEO, I forced myself to learn how to fly a plane while simultaneously building it. Don't sit under florescent lights from 9-5 for a steady paycheck. Life is too short. If you have an idea, found a startup and find out what you are capable of.”
Jonah Lopin, co-founder of Crayon
"Founding a startup or joining one early is not an economically rational thing to do. But economists are boring, life is short, and it's not the average outcome that matters, it's your outcome."
When Lopin graduated from MIT Sloan School of Management in 2007, he turned down offers from both eBay and Deloitte to join a little startup no one had ever heard of at the time: HubSpot. He was the sixth employee. “People thought I was crazy,” he says. But eight years later, HubSpot is worth $1.6 billion and is even picking up its growth pace as a public company. Lopin worked for HubSpot for five years as VP of customer success, and last year, launched the marketing design search startup Crayon.
Here’s his advice:
“Founding a startup or joining one early is not an economically rational thing to do. Don't kid yourself. The expected value of your earnings is much higher if you go work on Wall Street or climb the corporate ladder. But economists are boring, life is short, and it's not the average outcome that matters, it's your outcome. I left the HubSpot management team and co-founded Crayon in 2014, and here's what I know for sure: if you build a product people love and attract a big audience, you can change millions of lives, reshape an industry, ride the steepest learning curve of your life, have a ton of fun, make a bunch of money, and live a life of ‘actually doing stuff’ without the hassle of politics and corporate BS.”
Ross Brockman, co-founder of Downeast Cider
Here’s an atypical professional journey: One day Brockman was studying to be a lawyer at Bates College, the next he was cleaning kegs and checking fermentation cycles for his craft cider company. Downeast Cider House, which he co-founded with Tyler Mosher during their senior year, was launched in Maine and eventually moved its operations to Massachusetts in 2012. And while their ciders were initially only available on tap at bars and restaurants, you can now find them at a ton of liquor stores across the Northeast.
So, does he regret the unconventional path he took after graduating college? Not one bit. He told BostInno:
"Hey graduating senior! Turn down the job offer and start the business with your buddies. If you don't, you'll only regret it forever and ever."
Elias Torres, co-founder of Driftt
"There’s nothing you’ll learn at a big company that you won’t learn at a startup at a much faster pace."
Torres knows a thing or two about making the jump from big corporate job to startup. As of now, he’s working on the mobile collaboration startup Driftt, which is his fourth company. He also co-founded Performable, which was acquired by HubSpot. But for a full decade, he was working as a software engineer for IBM. While watching so many friends joining the startup world during that period of his career, he was tempted to do the same—but IBM kept making tempting offers every time he wanted to leave.
“That’s a problem with big companies,” he told BostInno in a phone interview. “They lure you in. And you get comfortable.”
Eight years in, he got the startup bug once again. And then one dinner with a group of entrepreneurs solidified his hunch about what path he should take: They insisted that he simply didn't belong in the corporate world. So, he decided to take a risk.
“I wanted to be known for what I contributed to the company, versus the politics that played out at a there,” he said. “There’s nothing you’ll learn at a big company that you won’t learn at a startup at a much faster pace. At a big company, you learn to play the game, to conform. Things move much more slowly. And you don’t get to see how a company gets built, funded, marketed, grown. That’s the most exciting part.”
There are two things, though, that Torres says you need to succeed at a startup: an ability to always take responsibility for your work, and an ability to deal with failure very well.
Catherine Havasi, co-founder of Luminoso
She’s CEO of the Cambridge-based artificial intelligence-based text analytics company Luminoso and was recently named one of the 100 Most Creative People in Business. She also co-founded and directs the Open Mind Common Sense Project, one of the largest knowledge bases of its kind in the world. Havasi built Luminoso based on nearly a decade’s worth of research on machine learning and neuro-linguistic programming, which she conducted the MIT Media Lab. And she’s a big advocate for working at a startup straight out of school.
She told BostInno:
"Keep learning and be creative. Get out into the woods or make something, and find ways to learn in everything you do. Stay open-minded: you never know where things might take you."
Ryan Wright, founder of WrightGrid
It was back in 2012 that Wright, then a Babson MBA student, founded Sol Power—which has since been renamed WrightGrid. And it was his passion for entrepreneurship coupled with his interest in improving environmental sustainability that led him to take his idea from an initial concept to a full-blown product release. His cleantech company, which is based at Boston’s Greentown Labs, specializes in designing and developing solar powered charging stations for mobile electronic devices. But before that, Wright worked as an engineering project manager at an Andover software company for a little under two years. So, why did he decide to leave?
"I left my 9-5 job to pursue my startup because I was tired of working towards someone else's vision and dream,” Wright told BostInno. “If I was going to realize anyone's dream, it was going to be my own."
Photos provided by the interviewees.
