Elevate The Hustle

"In Sales, the better you work, the harder you work, the more input you have, the better output you get. There's a level of justice to it."  Matt Naimoli knew he was built for entrepreneurship before he even knew what that meant—and a career aptitude test in elementary school that made him cry proved it.  From Division I catcher at UVM to Liberty Mutual's top 1-2 sales rep in t...

"If it doesn't keep you up at night and you're not excited to go to work on Monday, then it's not your thing. It's not your why."  Cari Gelber spent 20 years in events, hospitality, and the music industry—touring with bands, nearly landing a Disney movie deal, and selling out nightclubs in Manhattan. Then she pivoted into insurance staffing with zero experience, said...

"I was determined to play at the highest level, and I did."  Al Sica is talking about Division I baseball—but he could just as easily be talking about insurance M&A. Today, he's the founder of Sica | Fletcher , the #1-ranked insurance M&A advisory firm in the country, with over $19 billion in agency deals closed since 2014. 🏆  In episode 9 of Elevate the Hustle, Stan and Do...

"You never lose. You either win or you learn."  That's the philosophy printed on Mike Stromsoe's favorite travel shirt—and it's the mindset that took him from working nights at a bowling alley bar to building and selling a multi-million dollar insurance agency. 🚀  In episode 8 of Elevate the Hustle, Stan and Dom sit down with Mike Stromsoe —founder of UPP (Unstoppable Pro...

 "If you're not growing, you're dying."  That's not just a saying—it's Keith Captain's operating principle as President of FirstChoice , the #1 largest insurance network in the country. 📈  In episode 7 of Elevate the Hustle, Stan and Dom sit down with Keith Captain —former sports management student turned insurance claims adjuster turned network president—who&ap...

"I don't even know where the F your office is. I just need to know that I can get you."  That's what Rich Nesbitt's client told him when he was nervous about going fully virtual. 💻  In episode 6 of Elevate the Hustle, Stan and Dom sit down with Rich Nesbitt—34-year insurance veteran, owner of Johnny Walker Insurance, and a guy who went from knocking doors for $12,000 a ye...

"I quit my job, bought a house, and bought a franchise all in the same week. We had 45 days to make the mortgage."  That's how Jay Wolfberg went all-in on insurance. 🔥  In episode 5 of Elevate the Hustle, Stan and Dom sit down with Jay Wolfberg —, founder of We Insure 's largest franchise at $32M in premium, and now President of We Insure, one of the fastest-growing insurance...

"I was making someone else a lot of money. I was making good money, but the amount of money I was making someone else was considerably more."  That realization changed everything for Allen Hudson. ⚖️  In episode 4 of Elevate the Hustle, Stan and Dom sit down with Allen Hudson , founder of Community Risk Advisors . Allen was running a $65 billion insurance program when he realized the cor...

"A lot of people get paralyzed and they don't make a decision, but that's a decision."  Rob Bowen learned that in the Navy. At 50 years old, he decided to stop waiting and start his own insurance agency. 🎖️  In episode 3 of Elevate the Hustle, Stan and Dom sit down with Rob Bowen , Navy veteran, owner of Patriotic Insurance Group , and one of Elevate's very first clients....

"Do you know Kelly Bailey?"  If you're in Florida insurance, the answer is yes, and you're probably best friends. (And if not, you will soon.) 🐝 In episode 2 of Elevate the Hustle, Stan and Dom sit down with Kelly Bailey —founder of Hive Recruiter and serial connector who turned decades of "side hustle" placements into a full-time business.  They dig into:  Why fear...

“A giraffe walks into an insurance conference…”   Sounds like the setup to a joke, right? Except this actually happened. And we were the ones who brought it. 🦒   In this first episode of Elevate the Hustle, founders Stan Meytin and Dom Piccirillo tell the real story behind the 16 foot giraffe they brought into the FAIA conference in Orlando—and why it wasn’t just a stunt, it was a statement about...