"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 the country, to co-founding GNN Insurance and scaling it to an Inc. 5000 agency three years running, to selling in 2019 and launching Legacy Advisors—Matt has lived every phase of the agency owner journey. 🏆

In this episode of Elevate the Hustle, Stan and Dom sit down with Matt to talk about building, scaling, selling, and starting over smarter.

Matt breaks down:

• Why the most impactful early hire he ever made was someone who could remove him from the minutia—and why VAs are the modern version of that
• How GNN landed on home buyers as their niche (hint: it started with bobbleheads)
• The biggest mistakes agency owners make before going to market—and why your financials need to be buttoned up before you're ready to sell
• What a real sell-side M&A process looks like, step by step, and why going in eyes wide open changes everything

Plus, Matt shares why his competition isn't other advisors—it's agency owners who don't know companies like his exist, and why asking more questions is always the right first move.

If you're an agency owner who's ever wondered what your business is actually worth, thought about selling someday, or just wants to build something you'd actually be proud to hand off—this episode is for you.

Real talk, real stories, and occasionally real bad language.

🌐 Website: elevateteams.io
📷 Instagram: @elevateteams
🔗 LinkedIn: Elevate Teams
🎙️ YouTube: @ElevateTheHustlePodcast

"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 NO to the opportunity three times, and went on to help scale Elevate Teams from 5 clients to 95+ in her first year alone. 🦒

Today she's the company's Head of Talent Curation—the Insurance Matchmaker—and the reason agencies keep coming back for VA #2, #5, even #15.

In this episode of Elevate the Hustle, Stan and Dom sit down with Cari to talk about hustle, reinvention, and what it actually looks like to find work that lights you up.

Cari breaks down:

• Why she turned down Elevate multiple times, and what finally flipped the switch
• The matchmaking process that goes way beyond resumes and why culture fit changes everything
• Why 99% of agencies say "we're not ready" to hire, and how Elevated+ is fixing that
• Her advice for entrepreneurs who have 25 things going on and no focus

Plus, Cari shares why the best placements happen when agencies stop thinking "VA" and start thinking "team member," and what it feels like to go from selling booze to changing lives on both sides of the border.

Real talk, real stories, and occasionally real bad language.

🌐 Website: elevateteams.io
📷 Instagram: @elevateteams
🔗 LinkedIn: Elevate Teams
🎙️ YouTube: @ElevateTheHustlePodcast

"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 Dom sit down with Al to break down what actually makes agencies valuable—and what kills their worth. Al breaks down:

• The 3 non-negotiables buyers look for
• Why most agency owners get the timing wrong—and how waiting too long can kill your multiple
• Why you don't sell to get out—you sell to scale up (and how the right partner multiplies your wealth)

Plus, Al shares why he's been working off a yellow legal pad for 37 years, his philosophy on giving equity to the people who help you build, and why he'd rather outwork everyone than be the smartest guy in the room.

If you're an agency owner wondering what your business is actually worth, thinking about an exit someday, or convinced you need to wait until you're "ready" to retire before selling—this episode will change how you think about building value starting TODAY.

👉 Check out Al's podcast, Leaders & Legends: ‪

https://www.youtube.com/@sicafletcher

Real talk, real stories, and occasionally real bad language.

🌐 Website: elevateteams.io
📷 Instagram: @elevateteams
🔗 LinkedIn: Elevate Teams
🎙️ YouTube: @ElevateTheHustlePodcast