Elevate Teams

Elevate The Hustle

Business EN ↓ 36 episodes

Elevate the Hustle is the bold, founder-to-founder show for leaders who want to stand tall and scale smart. 🦒 Hosted by Stanley Meytin and Dominic Piccirillo , co-founders of Elevate Teams, the show dives into the real journey—growth, chaos, culture, and the systems that unlock time and revenue. You’ll hear from independent insurance agency owners, entrepreneurs, and operators who are in the arena: how they hire, how they lead, and how they use world-class talent to level up. It’s fast, funny, and practical—no jargon, no theory, just the plays that actually work. Who it’s for: Owners, princip...

Be sure to visit the podcast's website and support the creator: www.buzzsprout.com

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Elevate Teams

Episodes

What Really Happens When You Sell Your Agency ft. Matt Naimoli 23.02.2026 48:36

"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...

Why the Perfect Time to Hire is a Myth ft. Insurance Matchmaker Cari Gelber 16.02.2026 54:16

"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...

What Drives Insurance Agency Valuations ft. $19B M&A Expert Al Sica 09.02.2026 49:35

"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 Learn ft. Mike Stromsoe 02.02.2026 48:17

"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...

Run Your Agency Like It's For Sale ft. FirstChoice's Keith Captain 27.01.2026 45:13

"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...

From Door-to-Door Insurance to Fully Virtual ft. Rich Nesbitt 19.01.2026 43:13

"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...

The Samuel L. Jackson of Insurance ft. We Insure's Jay Wolfberg 12.01.2026 38:35

"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...

Leaving a $65B Insurance Program to Start From Scratch ft. Allen Hudson 05.01.2026 45:16

"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...

Starting an Insurance Agency at 50 ft. Rob Bowen 29.12.2025 28:59

"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....

The Queen Bee of Insurance Recruiting ft. Kelly Bailey 22.12.2025 49:35

"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...

We Brought a REAL Giraffe to an Insurance Conference 15.12.2025 33:57

“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...