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by Darrah Brustein

Taking the leap to be your own boss can be scary. Very scary. This is especially true if your background is in one industry, but your dream is to start a business in another.

I speak from personal experience: I went from a career in the wholesale apparel business to a whole new enterprise, when I launched a credit-card processing company. And I’m not the only career-changer: Recently, I wrangled an impressive crowd of entrepreneurs to tell their own, similar stories. All of these folks risked leaving stable jobs to go it alone in a world completely different from the one they knew. But they learned some important lessons along the way.

Here are those inspiring tales.

1. Cape Ann Brewing Company: from Wall Street to the brewery biz

Many a Wall Street employee hits the bar after work, but not many do what Jeremy Goldberg did and start their own! Describing the birth of Cape Ann Brewing Company, Goldberg remembers how, “During the late ’90s and early 2000s, I was working in the district of Manhattan, brokering bonds and trading stocks.” Like so many others downtown, he was a firsthand witness of the 9/11 attack on the Twin Towers, “and it affected me profoundly.”

So, rather than continue to “push money around,” Goldberg, then age 27, left Wall Street to help produce a documentary about U.S. craft beers. Right afterwards, he set to work opening the Cape Ann Brewing Company in Gloucester, Massachusetts.

Fast-forward 13 years. “Today, I’ve got a brick-and-mortar brewery and a restaurant on Gloucester’s working waterfront, and employ almost 50 people,” Goldberg proudly reports. “We’ve had our ups and downs, struggles and triumphs; but in the end, I know I’m doing something now that while unconventional — particularly for someone who at the time had no business taking on this kind of challenge — I am passionate about and allows me to look around and see evidence of a real accomplishment.”

Takeaway: Life-changing moments like 9/11 are just that: life-changing. Take those cues and follow your passions.

2. 2 Hounds Design: from physicist to dog collar extraordinaire

Alisha Navarro went from getting her master’s in physics and spending a year working as an engineer to chucking it all to found 2 Hounds Design. “My specialization was in electronics engineering, and I did a lot of work building and programming circuit boards,” Navarro explains. “Back in my day, I was definitely more of a -head and was fluent in several programming languages.”

Today, she says, “I am way out of my field of study, as we manufacture dog products, almost more of a designer field now, with the collars, even though the harness is a little more technical — and patented.”

Takeaway: Like Navarro, find ways to incorporate your skills in unexpected ways that best fit with your interests.

3. Click Intelligence: from corporate financier to marketer

Sharing his experience in and growth as a result of leaving corporate finance and diving into his own company, Simon Brisk says of his former life at financial house Eagle Star: “There was a lot of red tape in this role due to a long list of compliance [requirements], and it was very formal. I felt like a small cog in the wheel, not really understanding how I fit into the bigger picture! I then chose to leave the role to work in a field in which I had no previous experience: marketing with Click Intelligence.

“The landscape and thought-process were a million miles away from that of when I used to work for Eagle Star,” Brisk continues. But once he’d made the change, he discovered who he really was: “I had the freedom to be creative, to offer my viewpoint on internal processes and, most of all, feel that I mattered for the first time in my career.”

Takeaway: If you’re feeling like a small cog in a giant wheel, consider making a change that allows you to feel like you’re growing and using your talents as Brisk did. 

4. Sin City Cupcakes: from legal HR VP-turned-“adult”-cupcake-baker

Lisa Song Sutton went from working as an associate and VP of human resources in a law firm to founding Sin City Cupcakes, which specializes in alcohol-infused versions of this popular dessert. Explains Sutton: “When I transitioned from working as an associate and VP of human resources in a law firm to founding an alcohol-infused cupcake company, the hardest part wasn’t walking away from the salary, the steady job or the perceived prestige of my occupation; the most difficult part was telling my parents!”

Turns out her parents, who had put Sutton through college and law school, were happy to hear she was fulfilling her dream of being of own boss. They’re just as glad to hear that business today is booming.

Takeaway: Disappointing one’s family can be a real barrier, but keep in mind that most families just want you to be happy. 

5. Big Machine Parts: from banking exec to ecommerce guru

How do you go from founding executive at a tech-focused  community bank to founder of an ecommerce company whose focus is easing the process of buying the right heavy-duty part?

Jeff Chambers of Big Machine Parts has the answer: “Opportunity and curiosity,” he says. “We started the bank with a clear strategy of staying focused on entrepreneur-led companies and distributing services through technology rather than brick-and-mortar branches. After we sold the bank, I knew my time in heavily regulated industries was over, but my desire to apply the same principle of ‘clicks over bricks’ didn’t change.”

Finally settling on transportation, and trucking in particular, Chambers says he found his “white whale” in the discovery that the $20 billion after-market parts market was being “grossly underserved” by technologically efficient distribution companies. So began, “And we set out to make the process of finding the right part, right now, as easy as taking a picture.”

Takeaway: Allow “opportunity and curiosity” to fuel your career trajectory. 

6. VenturePact: from private equity to tech entrepreneur

Randy Rayess, CEO of VenturePact, says that “regret minimization” was what first persuaded him to take the leap. He had previously worked in private equity as part of a team that looked to invest in large tech companies. “While the team was great, starting VenturePact with a good friend allowed me to work on a problem I was very passionate about,” Rayess says.

“Given the amount I could learn as an entrepreneur, and the contribution I could have when starting a new company, I decided to make the jump into the startup world,” he continues. “While this was considered very surprising to my colleagues and friends, and seemed very risky, it felt like the right thing to do.”

Still, doubts lingered. But those doubts disappeared, says Rayess, when he watched a video by Jeff Bezos about what Bezos calls his Regret Minimization Framework; Rayess says the video provided context for his own decision. “I knew that if I was going to look back at my life in 50 years, I would regret not pursuing VenturePact, so I made the jump.

“The last few years have been an amazing ride and learning experience.”

Takeaway: Consider “regret minimization” to help you map out your next steps.

7. Beacon: from the Pentagon to the airline industry

In 2011 Wade Eyerly was working at the Pentagon for an intelligence agency. “I loved many of the people with whom I worked, but I was scared by the career path,” Eyerly remembers. “I could spend the next 15 years sitting in the same seat. So, in 2012 I packed my bags.”

He started two companies. His second, and current one, is Beacon. “The transition was interesting because I was excited to be doing something that seemed to better fit my personality, and nervous about the risk I was taking, the stresses that it would put on my family.” Eyerly adds that he also had to “un-learn the process focus” that government work creates and become very “outcome focused.”

“Transitioning from the government to startups is a strange kind of culture shock, but it was one of the best decisions I’ve ever made,” he says.

Takeaway: It can be scary to go from a rigid structure to none at all. If you’re the type to thrive with your own rules, take a note from Eyerly’s journey.

8. Goza: from stock broker to tequila connoisseur

It’s not every day that a well-paid up and leaves to launch a tequila company. Unless, of course, you’re Jacob Gluck, founder of Goza, the tequila company. “Though I loved the stock market — and still do — the job lacked the creativity I craved in my professional life,” Gluck says. “If anything, I learned on Wall Street that everyone wants the reward, but few will take the risk.”

It also became clear “that the real risk for me was not following my gut — which was to be my own boss.” In spring 2012, he moved back to his hometown Atlanta and into his parents’ house. “Especially for the first year, when it was just me trying to do the whole ‘tequila thing,’ I felt very isolated and alone.”

He also faced a steep learning curve. “You can’t just  ‘how to start a tequila company,'” he says. But, “If I was going to bet on anyone, I figured it best to bet on myself.” Today, for the first time, he feels that he is doing “exactly the thing I was meant to do.

“Professionally, there’s nothing else I want to be doing. It really is true: A little ‘Goza’ long way.”

Takeaway: It’s challenging to leave an industry you enjoy and a cushy salary, but like Gluck, if you find that your gut is leading you in another direction, it’s generally best to listen to it. 

9. Nomaterra: from dream fashion gig to fragrance startup

Agnieszka Sygnarowicz Burnett, co-founder at Nomaterra, had a “dream job” out of journalism school working at Glamour magazine, but left to follow her newer dream of becoming a startup founder. The editorial beauty world had been fast­-paced and intense, she says, but, “I’ve never been one to follow the herd.”

So, following a subsequent stint at Columbia University, in a post-baccalaureate science studies program, she and her husband Benjamin founded Nomaterra Fragrances. The two had met in physics class at Columbia, and after founding their company, “We worked out of our tiny New York City apartment. I was the happiest I’d ever been.”

That happiness helped launch a fragrance brand. “I trusted my nose to steer me in the right direction,” Burnett jokes. “I utilized my knowledge of chemistry, my experience in beauty and my passion for nostalgic travel, to create ‘scentsory’ experiences that transport one to a different time and place.

“It was the best decision, to make the leap from a traditional career path to one where we are in complete control of our company, its integrity and ethos.”

Takeaway: Even a dream job isn’t always fulfilling. Take stock of how to combine your dreams with your skills and demeanor and you’ll find success, just as Burnett did.


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