"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

"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 Profit Producer) and former independent agency owner—who now teaches agency owners how to grow their business, create wealth, and live life on their own terms.

Mike breaks down:

• Why he's NOT an insurance agent—he's a marketer who happens to own an insurance business (and why that shift changed everything)
• The simple 3-step blueprint that took him from broke to multi-million dollar exit: People, Processes, Promotion (in that order)
• Why "good enough is good enough" when delegating—if someone can do it 80% as well as you, let them do it

Plus, Mike shares why he makes chili rellenos from scratch and how his "IDGAF muscle" got stronger with age.

If you're an insurance agency owner buried in minutiae, working 14-hour days on $15/hour tasks, or convinced that nobody can do it as well as you can, you can't afford to skip this one.

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

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

"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's spent the last 8 years helping 720+ independent agencies scale by a minimum of 15% every year.

Keith breaks down:

• Why complacency is the #1 killer of agency growth—and how to recognize it before it's too late
• The "run your agency like it's for sale" philosophy: what it means and why it matters even if you never plan to sell
• How to stop working IN your business and start working ON it (hint: build your org chart 5 years out and hire into it)
• The truth about hiring out of desperation—and why most failed hires are a process problem, not a people problem
• Why you need to start planning your exit 10 years before you think you'll need it (or you'll lose all control)
• What the 2022 merger with Marshberry taught him about culture fit, asking the right questions, and being willing to walk away

Plus, Keith shares why he'd rather sit down for dinner with a candidate than trust a resume, how he almost became a sports agent, and why technology without a customer-first mindset is just expensive clutter.

If you're stuck at 3-5% growth, tired of being the bottleneck in your agency, or wondering how the hell to build a team that doesn't need you for every decision, this episode is for you.

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

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

"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 year to running a fully virtual agency powered by 7 VAs.

Rich breaks down:

• Why door-to-door sales was the best (worst) training of his career—and the mindset that kept him going after getting doors slammed in his face
• How he bought the agency in 2006 after putting in 14 years of grinding it out in a small-town, old-boy network
• The brutal truth about staffing in rural America post-COVID—and why he ditched the brick-and-mortar office entirely
• His "captain of the ship" philosophy: if you're the owner doing certificates of insurance on Sundays, you're not steering—you're missing the iceberg

Plus, Rich shares his biggest hunting win in the Adirondacks and why his son just decided to get licensed after four years in construction.

If you're drowning in agency operations, struggling with staffing, or wondering if going virtual could actually work in your market, this episode is required listening.

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

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

"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 franchise organizations in the country.

Jay breaks down:

• Why he was born into insurance, vowed never to do it, then became obsessed with it anyway
• The sales reciprocity strategy that generated 100% referral-based growth (and why timing matters more than the ask)
• How he went from a bug-infested office above a granite store to building a $32M insurance empire in 10 years
• Why virtual assistants are the "sweet spot" between licensed reps and automation—and how they transformed his service model
• What he looks for when signing new franchisees (hint: it's not insurance experience)

Plus, Jay shares his signature dish (24-hour brined buffalo wings made from scratch), why golf changed his business career, and how got the nickname of "Samuel L. Jackson of Insurance."

If you're thinking about starting an independent insurance agency, buying an insurance franchise, or scaling with virtual assistants, this episode is required listening.

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

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

"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 corporate ladder had a ceiling—and he didn't own any of it. So he walked.

Allen breaks down:

• Why "Jane and John Doe Insurance Agency, Inc." is dead, and what replaces it
• The shocking reason his first US-based hire quit after 3 months
• How he's scaling by having senior team members build and train their own teams
• Why specialization is the only path forward for agencies trying to compete
• His advice for both brand-new agents and 25-year veterans who've been doing it the same way forever

Plus: Why Red Robin became his go-to meal, how he got banned from almost every bar at UMD, and why entrepreneurship dropped his golf handicap from 6 to 11.

If you've been waiting for the "right time" to go independent, this episode will make you rethink everything.

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

If you're an insurance agency owner or entrepreneur who wants straight talk and stories from the trenches, hit play.

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