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How To Take Calculated Risks To Make Your Best Shot

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David Saracino/Thrillist

We all daydream about quitting our day jobs and running off to join the circus (or coding some app that turns your face into a puppy and selling it to Google). You may think it’s far-fetched, but there are real people out there who have actually done just that: risk it all on one of their lifelong dreams. How did they muster up the guts to do it, and how did they prepare themselves for that great leap into the vast unknown? We tracked down a handful of self-starting entrepreneurs to find out.

The secret is lots of small changes that will shift your attitude. You don’t have to start your own business to live the way you want. Practice these fundamentals in small ways in daily life, and you’ll be ready to make the big decisions quickly and without second-guessing yourself. Once you’ve perfected these behaviors, then you can make bigger changes. Maybe this time next year you’ll be printing “CEO” on your business cards, too.

Mark Aselstine, Uncorked Ventures

Mark Aselstine knew absolutely nothing about selling wine before he started Uncorked Ventures with his brother-in-law seven years ago. They just figured if it tanked, they might as well get stuck with a non-perishable inventory of something they actually liked.

The economy was still in recovery then, and Aselstine had seen his income reduced drastically. His brother-in-law was working in HR, where he’d just had the unpleasant responsibility of laying off more than 200 people. They were at a wedding together when they decided they would start their subscription-based, online wine club. Even though they had essentially zero wine-selling experience, they both quit their day jobs and committed to making the business work. They quickly learned flexibility and a willingness to learn are keys to success no matter what the venture.

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Connect with people who have done something truly -- not superficially -- similar
Networking isn’t just a necessary evil for moving forward at your corporate drone job. Turns out, it’s just as helpful for getting into any unfamiliar new venture.

Just make sure you’re talking to the right people. When Aselstine and his brother-in-law decided to open their business, they spent months talking to wineries. That was helpful insight into the wine industry, Aselstine said, but that information didn’t prepare them for entering the e-commerce, subscription business world. Instead, he says he wished he spent more time networking with those e-commerce entrepreneurs -- meetings that would have made him better prepared to enter into an e-commerce business, even though that business sold wine.

“If you’re opening an online locksmith referral [business],” he says, “You don’t necessarily need to talk to other locksmiths. You need to figure out what the broader category is, because you’ll get a lot better, longer-term information.”

Besides putting you at ease about the risk you’re about to take, a mentor will be able to give you advice that’s geared towards the activity you’re getting into.

Don’t be too tied to your plan
Clearly, you should have some sort of game plan if you’re thinking of taking a risk like quitting your job and running off to a new city to start the next Snapchat. But, you shouldn’t become inflexible about how this new venture should go. When you actually get your hands dirty, you may have to totally rework what you’re doing.

“People spend so much time on a business plan, and we agonized over ours for a long time, maybe hundreds of hours,” says Aselstine. “And then as soon as we opened, it wasn’t even worth the paper it was printed on.” For instance, when Uncorked Ventures first started, Aselstine said that he and his business partner weren’t entirely sure about what tools they needed to operate their business. They ended up with a few different iterations of their website, and initially used software built for the wine industry that was incredibly buggy -- because nothing else was available for them to use for a subscription business. Once they pivoted to a new website, Uncorked Ventures settled into a new plan and started on the growth path that led to their current standing.

So the best preparation? It may be to just be ready to roll with the punches... and plan how you’ll swing back.



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Chris Covelli, #GetFried

Chris Covelli was climbing pretty high up the corporate ladder, but gave it all up for one thing: poutine. He decided to leave his job as head of ADPRO Sports corporate division, which supplies sports teams (like the NFL) with their uniforms, to run his franchise #GetFried. It’s a fast casual chain that offers loaded fries and the Canadian delicacy poutine, but for Americans. He had nearly zero experience in the food industry, having only been a barback and a bus boy before entering his professional career -- but he loved the idea of #GetFried so much that he left the desk gig for dozens of fryers.

Trust yourself that you’ll land on your feet
Let’s be real: anyone reading a how-to guide to taking risks is probably pretty risk adverse. That most likely means you’re going to weigh your decision carefully before you jump in. Because of that, Covelli says you need to trust that even if you fail horribly, you’ll find a way to make the best of it. “You just have to know and trust yourself that if this doesn’t work out, you will use this as a learning experience,” he says. “And know that even in a worst case scenario, you’re going to land on your feet.” Hey, you always do, right?

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Your stress will bring out the best
Our brains are pesky, anxiety-inducing machines programmed to make you second-guess yourself (thanks, evolution!). That’s not exactly going to change just because you overcame that initial leap of faith. Long after that, you’re still going to spend some time questioning your decision and worrying if it was the right one, Covelli says.

“I don’t think it ever goes away, I think it becomes more subtle. I think you can bury it a little deeper with the more you do that helps the brand succeed,” he says.

For him, he still feels it when he has that feeling when a new franchisee comes on board and takes their own personal risk in his business. But, he turns that anxiety into motivation to keep pushing forward.

Leon Logothetis, Netflix’s Kindness Diaries

We’ve all daydreamed once or twice about dropping our regular gigs to jetset around the globe. Leon Logothetis actually did it, and pulled it off by relying on the kindness of strangers. Before he had his own Netflix series, he was a broker in London with (as he describes it) “everything you could want.” But after years of feeling unfulfilled in his job and life, he decided he needed a change, and a drastic one. So he quit and started traveling the world thanks to the help of complete strangers.

Eventually, though, he ended up back behind a desk in LA. While walking down Hollywood Boulevard one day, though, he saw a homeless man with a sign that said “Kindness is the best medicine.” He then came up with the concept of The Kindness Diaries, and left the corporate world for good to travel the world and spread kindness.

Lesson learned: it’s smart to do a test run before you gather what you’ve learned and officially embark.

David Saracino/Thrillist

If you’re really nervous, start small
Even though Logothetis dove right into traveling around the world, he suggests trying a different approach, especially if you’re anxious about taking risks.

“Taking risks doesn’t mean you have to go out and quit your job and buy a vintage motorbike and travel around the world,” he says. “What it does mean is you have to take small baby steps towards reaching your goal.”

For example, if you think you’d make a great baker, but can’t imagine dropping your day job to go to culinary school, start with just heading to the library and reading a book about baking. Then, take a weekend class. “Once you finish that risk, maybe then there’s the next risk. You keep on extending how you are opening yourself up, small little baby steps,” he says.

Make it impossible to back out
Remember that bit about how your brain is a pesky, anxiety-inducing machine? When something feels right, the best thing to do is not let your brain get the better of you, Logothetis advises.

“Once your feelings have guided you that it’s the right thing to do, your brain will do everything in it’s power to stop you from doing it,” he says. To avoid that? Put yourself in a situation where you literally can’t turn back -- sign a crucial document, tell someone who will hold you accountable, just make one key move that will make it nearly impossible to pull the plug on your plan, especially if you’re the type of person who overanalyzes situations.

If someone’s going to talk you out of it, don’t tell them
We all have a few naysayers in our lives who mean well, but just don’t always get it. (Hi, Dad.) If there’s someone close to you who will try to convince you not to take a risk, just because it’s, well, risky, then Logothetis suggests keeping your plans to yourself until things are squared away.

“Your heart is sacred, and what you want to do with your life is sacred,” he says. “And if you feel like you’re going to share it with someone else and they are going to tell you don’t do it, don’t share it with them,”

Once there’s no turning back, you can tell them about your decision -- but there’s no reason to get their input beforehand. (You’re an adult, damnit!)

Monique Bernstein and Eli Zauner, Universal Yums

You thought moving in with your SO was a leap of faith? These two started a business together when they had just started dating, and this year it broke $1M. Bernstein and her boyfriend Zauner started working in the corporate world right out of college, but quickly realized it wasn’t a good fit for either of them. After months of being unhappy in white-collar toil (like making lists of “How To Appreciate the Feedback From My Manager” unhappy) Bernstein jotted down 10 business ideas she could start in a day. That night, she shared it with Zauner, and he offered to start one of them with her.

Together, they quickly developed Universal Yums, a subscription snack service that brings hard-to-find international treats to American shores, putting up only $2,000 between them. And, yes, they are still dating.

Don’t focus on the cash
You hear a lot of stories of people who unchained themselves from their desk jobs, made a quick $1M, and now (you assume) they spend their days on a beach in Miami. That’s probably not the case, especially if you’re starting a business, Bernstein warns.

“You have to be very real with yourself about the sacrifice that it’s going to involve,” she says.

There’s going to be a lot of hard work, especially in the beginning, so if you’re only taking this risk for the cash, don’t bother. Going on vacations and partying until all hours of the night are still only the stuff of Kardashian-fueled trust funds, even in this startup culture.

Focus on what you’ll learn
Sure, if you’re only focused on raking in fat stacks of cash, taking a risk is going to be pretty frightening -- not to mention potentially disappointing. Instead, Zauner and Bernstein suggest changing your definition of success, or at least altering your perception of it. They felt like they weren’t gaining the skills they wanted in their day jobs, and that was making it difficult to go to work every day. Universal Yums, whether it failed or succeeded, was an educational opportunity to both of them.

“We felt like if we worked on a business where we were doing things that we’re going to help us grow as people, then it was going to be worth it, no matter what happens,” says Zauner. With that mindset, what is there to really lose?

Compensation was provided by Cotton. The opinions expressed herein are the author's and are not indicative of the opinions or positions of Cotton.