From Mafia Moves to Business Boss: The Wild Ride of 2 Sisters Sports Bar
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From Mafia Moves to Business Boss: The Wild Ride of 2 Sisters Sports Bar
I thought I had life figured out at 22. I was sharp—so sharp I could remember not just people’s names, but their drink orders, their kids’ birthdays, even their dogs' favorite chew toys. I was invincible, running my own sports bar, juggling chaos like a seasoned pro.
But the truth? I wasn’t supposed to own a bar. I was supposed to be in St. Thomas, sailing the seas and spearfishing for my dinners. Instead, I got robbed—literally—and found myself playing mafia with my sister, chasing down the bandits who stole my life's savings.
Lesson 1: When Life Steals from You, Sometimes You Gotta Steal Back (Figuratively… Mostly)
It started with $30,000. That was my golden ticket—meant to build a guesthouse on my parents’ property so they’d finally stop calling me a flight risk. But instead, some low-life (we'll call him Life Lesson Lizard) swindled me, and suddenly, my dreams of island life were circling the drain.
So what did two young, dumb, but determined girls do? We went full mafia. We found some of the biggest, baddest guys in Lawrence, MA, to be our ‘muscle,’ put up a $1,000 reward, and started breaking into houses looking for our Lizard. Not our finest moment, but hey—it worked. Sort of. We didn’t even have to spend the money, just some dignity and a few legal gray areas.
But by the time we got to him, my $30,000 was long gone. Instead, I got a pile of abandoned, worthless restaurant equipment in a sketchy storage unit on the wrong side of Haverhill.
Lesson 2: Sometimes You Pivot... Straight Into a Business You Never Wanted
What does one do with two U-Hauls of useless equipment? Enter my uncle, a pawn shop owner and local ‘big deal.’ He hooked me up with a restaurant equipment dealer who, out of pure pity (and maybe my uncle’s influence), offered me a whopping $5,000 for the lot.
I was officially screwed.
No guesthouse. No island escape. Just me, a failed dream, and a pile of junk.
So I did the only thing I knew how to do—make it work. I found a landlord willing to let me put the equipment to use, and suddenly, I was opening a sports bar, despite my only experience being a short stint at Hooters.
Lesson 3: Passion Isn’t Always About the Business. Sometimes, It’s About the End Goal.
Did I dream of slinging beers and arguing over liquor licenses? No. But I had a goal: Make my money back, finish the guesthouse, and get my butt to the Virgin Islands. That fire in my belly is what got me through the endless hoops the town put in front of me, trying to keep another sleazy dive from opening.
I had to learn everything—fast. From town ordinances to business licensing, fire permits to occupancy limits, even how to form a legal entity. Pro tip: When registering a business, have at least three name options ready. Otherwise, you’ll end up stuck with whatever your friend randomly shouts out, and that’s how you end up explaining a name you don’t even like for the next five years.
Oh, and you’ll need to know the difference between an LLC, S-Corp, and C-Corp. (Hint: An LLC protects your personal assets if things go south, and for most small businesses, it's a solid choice. But talk to an expert before deciding.)
Lesson 4: Entrepreneurship Is Just a Series of ‘WTF Do I Do Next?’ Moments
Step by step, I figured it out:
- Registered my business.
- Got my EIN from the IRS (free, by the way, so don’t fall for scams!).
- Opened business bank accounts (yes, plural—you’ll need an operating account, a payroll account, and a tax account at minimum).
- Designed a logo (thank you, Freelancer.com).
- Hired employees… or, well, accidentally hired the wrong ‘Jessica’ and just rolled with it.
Speaking of hiring—entrepreneurs, listen up. You can Google all the quirky interview questions in the world, but at the end of the day, you’re going to have to make gut calls. People will surprise you. The wrong hire might be your best employee. And sometimes, you just have to go with the flow.
Lesson 5: Every Business Needs a Bible (a.k.a. The Business Plan & Employee Handbook)
If you take nothing else from my story, remember this: Have a business plan. Even if you change it a million times, you need a map. And for the love of legal safety, have an employee handbook. Outline everything—expectations, responsibilities, policies—then make them sign it. Protect yourself.
Lesson 6: Adapt or Die (Or At Least, Adapt or Go Bankrupt)
From getting the wrong ‘Jessica’ to learning that beer distributors don’t always offer credit (so I had to scramble for cash-on-delivery payments), everything about running 2 Sisters Sports Bar was a crash course in rolling with the punches.
When I finally got that ‘OPEN’ sign up, I felt like a badass. And for two years, I ran that bar, making back my money and then some. It wasn’t easy. It wasn’t my dream. But it was a steppingstone.
I sold the bar, got back on track, and finally set my sights on that guesthouse and my island escape.
What happened next? Well, that’s another story for another Post. From that moment until today, I've undergone several more even wilder business endeavor rides—spanning a wide range of industries. Along the way, I've experienced so many more WTF moments and Ah-Ha revelations. I'll be sure to post about them shortly, sharing not just the stories but also the valuable lessons, resources, and networks I've gained—so you, too, can benefit from the journey.
Final Takeaways for Aspiring Entrepreneurs:
- Shit will hit the fan. Expect it. Have a backup plan.
- Passion doesn’t always come from the business—it comes from what it allows you to do.
- Know your legal and financial basics before jumping in. Or, at the very least, find someone who does.
- Your team will make or break you. Choose wisely.
- Adapt, pivot, and be ready for the unexpected. Because it’s coming, whether you like it or not.
And if you need guidance on any of this, check out The Yoga Entrepreneur Blueprint. Because if I can go from mafia tactics to running a legitimate business, so can you.