How to Bounce Back After Losing Everything: Craig Berberich’s Journey from NYC Bar Owner to Insurance Expert
On this week’s episode ofMoving Mountains, I sat down with Craig Berberich of National HR for a conversation that was nothing short of a masterclass in resilience, reinvention, and the power of showing up. Craig’s story is proof that success isn’t a straight line—it’s a winding road full of wild detours, hard lessons, and eventual clarity.
Whether you’re an entrepreneur feeling the weight of a business venture, or someone navigating a career pivot, Craig’s journey offers valuable insights on how to rebuild after life knocks you down.
From Bartender to Bar Owner (Accidentally)
Craig’s entrepreneurial story began in the most unlikely of places—a nearly empty bar in New York City. While working a side gig as a bartender, a stranger walked in demanding payment from the owners who were behind on their bills. Seeing an opportunity, Craig skipped the middleman, paid off the debt himself, and bought the bar outright.
But here’s the twist: the space was a former famous gay bar, and despite Craig’s initial vision of a happy-hour spot, the existing clientele kept coming. Rather than fight it, he embraced it, turning it into a successful, full-fledged gay bar. The business was a hit, but the grueling hours—working 4:00 p.m. to 4:00 a.m., six days a week—took a serious toll on his health. Eventually, he sold the place, but even that didn’t go smoothly, leading to legal headaches when the new owners ran into trouble.
Takeaway:Sometimes, the business you end up running isn’t the one you planned. Listening to your market can be more profitable than forcing your original vision.
The “Regular Job” Trap and Losing a Loved One
After the bar, Craig craved stability. He took a $15-an-hour job in the shipping department at a printing company, grateful for the lack of stress. But his work ethic quickly pushed him up the ranks to manager, dealing with high-pressure clients like Nike and Louis Vuitton. The stress returned.
A subsequent job with a vendor in Trenton meant a brutal three-hour daily commute and a toxic work environment. It was during this difficult period that Craig faced his deepest personal loss: his sister passed away. The company’s lack of support made the decision to leave easy. He never went back.
Takeaway:No amount of money is worth sacrificing your mental health or missing the moments that matter. Sometimes the hardest decision is walking away, but it’s often the most necessary.
Real Estate, 300 Doors, and a Partner Who Stole Money
Returning to what he loved, Craig got his real estate license—in March 2008, right as the market crashed. Faced with sellers who were underwater on their mortgages, he pivoted to property management. Within three years, he was managing300 doors(individual single-family homes). It was a successful business, but he was burning out, acting as the sole point of contact for angry owners and tenants with broken air conditioners on the 4th of July.
He sold the business to a larger brokerage for a management position. It seemed like the perfect exit until he discovered the broker was stealing from clients. She went to jail, and Craig was left in the basement office, watching the chaos unfold.
Takeaway:Growth without structure and delegation leads to burnout. Also, thoroughly vet your business partners. A high-level position means nothing if the leadership is corrupt.
Partnering Up and Building a Seven-Figure Empire
Amid the rubble of the failed brokerage, a colleague across the hall saw potential. She had a massive book of business managing foreclosures for Fannie Mae but needed to move to California for her husband’s residency. She asked Craig to partner up. They formedCB Flity Group, operating under Keller Williams, and grew the business to nearly seven figures in revenue.
This success forced Craig to confront his introverted nature. He struggled with holding team members accountable and dealing with conflict. His solution? He hired a coach. That decision helped him develop the leadership skills necessary to manage a growing team.
Takeaway:Your natural tendencies don’t have to limit your growth. Hiring a coach or mentor can provide the tools to overcome personal hurdles that are holding your business back.
The Current Chapter: Navigating a New Industry with an Entrepreneurial Mindset
Today, Craig is withNational HR, helping small to mid-sized businesses navigate the complex world of health insurance. It’s a new industry for him, and he admits it’s humbling. After being an expert in real estate, he’s now in rooms where clients sometimes know more than he does. The sales process is long, filled with "no’s," and requires a thick skin.
So how does he handle it? He’s leaned back into the habits that keep him grounded:
Rituals:He goes into the office every day, even when he doesn’t have to, to create a clear separation between work and home life.
Fitness:He hits the gym straight after work and coaches his son’s lacrosse team, using the field to relieve stress.
Mindset:He’s a big proponent of meditation and continuous learning, consuming podcasts like "Outbound Squad" to sharpen his skills.
The Grind:He emphasizes that success comes from putting in the reps. “If you want something, you got to grind.”
Takeaway:Entering a new industry later in your career is tough. Humility is required, but so is the willingness to keep learning and practicing every single day.
Final Advice for Entrepreneurs
When asked what advice he’d give to others, Craig kept it simple:
Keep Learning:You have to be the smartest person in the room to be successful. Education doesn’t stop after school.
Grind It Out:There’s no substitute for hard work. Identify what you want and commit to the work required to get it.
Serve the Small Guy:At National HR, Craig loves helping small “mom and pop” shops. Saving a business $5,000 a year might mean a car for a teenager or a semester of college tuition. Those wins are what drive him.
Craig Berberich’s story is a testament to the fact thatresilience is built, not born.From a bar in NYC to a real estate empire, from losing it all to finding his footing in insurance, he has consistently shown that the ability to pivot, learn, and keep grinding is the ultimate key to success.
If you want to get in touch with Craig or learn how National HR can help your business save on health insurance, you can reach him atNationalHR.comor find him on LinkedIn.
