Elevate The Hustle

Elevate Teams
  • 5.0 (2)
  • ENTREPRENEURSHIP

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, principals, and operators who want real leverage—better processes, better people, better outcomes. What you’ll get: Actionable hiring and ops strategies, culture-first leadership insights, and memorable stories that push you to think bigger and build bolder.

  1. Your VA Could Be Your Next Leader ft. Gabriela Rodriguez

    MAR 17

    Your VA Could Be Your Next Leader ft. Gabriela Rodriguez

    "This is not the ceiling for me. I need more, I want more, and I've always worked for that." Gabriela Rodriguez started as a virtual assistant in Venezuela in 2017. $1 an hour. Paid in a collapsing currency. Her first client? Cold calling people in Mexico to book appointments. She got removed from the placement—couldn't hit the goals. But she didn't give up. She got placed with Stan doing marketing work for his production company. Then COVID hit in 2020, and Stan's production business went to zero. He kept just one employee through it all: Gaby. When Stan and Dom started Elevate Teams, Gaby wasn't supposed to be part of it. Just budget and marketing help. But she kept getting pulled deeper—more meetings, more responsibility, more seats. Marketing. Finance. Sales. Operations. She did it all.  Nine years after starting at $1/hour, she's the Head of Operations. She built the systems that run the company. She trained the team. She's the soul of Elevate. And she's still not satisfied. This isn't her ceiling. In this episode of Elevate the Hustle, Stan and Dom sit down with Gaby to talk about never settling, working your way up from the bottom, and why ambition doesn't care where you're from or what you're paid. Gaby breaks down: What it's like to go from $1/hour to running operations for a US companyWhy consistency and showing up ready for anything is what separates good from greatHow she learned English from YouTube (shout out to Logan Paul)Why stability and opportunity mean everything when you're building from Latin AmericaPlus, Gaby talks about being Stan's toughest critic, why she still dreams bigger, and what it takes to inspire an entire team across borders. If you've ever felt like you're stuck, like your ceiling is determined by where you started, or like you need permission to want more: this episode is for you. Real talk, real stories, and occasionally real bad language. 🌐 Website: elevateteams.io 📷 Instagram: @elevateteams 🔗 LinkedIn: Elevate Teams 🎙️ YouTube: @ElevateTheHustlePodcast

    49 min
  2. Why Most Agency Owners Hire the Wrong People ft. David Ragno

    MAR 10

    Why Most Agency Owners Hire the Wrong People ft. David Ragno

    The best investment you can ever make? Yourself. "I took a 70% pay cut at 25 just to get my foot in the door. Whether I made money at it or not, it was going to provide me tremendous value long term." David Ragno started at Travelers crunching big data and analytics—making good money, safe career path, comfortable future. Then he walked away from it all to work an entry-level role at Keys Coverage in South Florida.  70% pay cut. Zero title.  He just wanted to understand insurance at a micro level, not from a spreadsheet. Nine years later, he's the CEO. Fifteen acquisitions. Expanding across Florida and into the southeastern U.S. Launching a substance abuse-focused MGA. Building a real estate portfolio on the side. And he's never hired a single experienced producer—not once. In this episode of Elevate the Hustle, Stan and Dom sit down with David to talk about falling in love with problems, sacrificing for mentorship, and why the agencies stuck at $1M, $5M, and $12M all made the same mistake: they built for today instead of tomorrow. David breaks down: Why he hires for grit and trains for skill The glass ceilings agencies can't break through, and why reinvestment is what separates growth from stagnationHow transparency and trust unlock speed in your business Plus, David talks about getting sober at 25, why YPO membership changed how he thinks about business, and how blending personal passion with professional work unlocked a level of success he couldn't fake. If you've ever tried to do it all yourself, built your org chart for where you are instead of where you're going, or convinced yourself you need "experienced" hires to scale—this episode will challenge everything. Real talk, real stories, and occasionally real bad language. 🌐 Website: elevateteams.io 📷 Instagram: @elevateteams 🔗 LinkedIn: Elevate Teams 🎙️ YouTube: @ElevateTheHustlePodcast

    50 min
  3. Don't Wait for a Promotion. Take it ft. Sonya Horton

    MAR 3

    Don't Wait for a Promotion. Take it ft. Sonya Horton

    "I promoted myself to COO. See, when you don't want to promote me, I promote my damn self."  Sonya Horton started as a receptionist at a Brooklyn livery cab brokerage in the '90s—answering phones for quarters and dimes, reading BOP policies on the train, learning insurance line by line because there was no ChatGPT, no LinkedIn, no shortcuts. Just work ethic inherited from immigrant parents who said: stand on that line.  Twenty-five years later, she was COO of Mogil Organization. Now she's at The Cody Group—the company founded by the same kid she trained 20 years ago when he was "staring into space" at his desk.  In this episode of Elevate the Hustle, Stan and Dom sit down with Sonya to talk about taking what's yours, letting go of what's killing you, and why the best managers don't throw people away—they find the right seat.  Sonya breaks down:  How she promoted herself to COO Why confidence isn't arrogance when you know your value The control freak mentality that ruled her for 30 years and what finally changed her mind about delegation (spoiler: it was an Elevate Teams VA) Plus, Sonya shares how her psychology degree became her superpower in insurance, and why her daughter Samira is probably going to run the White House someday.  If you've ever been the bottleneck in your own business, waited too long for someone to recognize your work, or convinced yourself you're the only one who can do it right—this episode was made for you.  👉 Check out Samira's music: ​  ⁨https://www.youtube.com/channel/UCgIL1rnS8d-Lntdu9BZwLHQ Real talk, real stories, and occasionally real bad language. 🌐 Website: elevateteams.io 📷 Instagram: @elevateteams 🔗 LinkedIn: Elevate Teams 🎙️ YouTube: @ElevateTheHustlePodcast

    1 hr
  4. What Really Happens When You Sell Your Agency ft. Matt Naimoli

    FEB 23

    What Really Happens When You Sell Your Agency ft. Matt Naimoli

    "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 thatHow 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 sellWhat 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

    49 min
  5. Why the Perfect Time to Hire is a Myth ft. Insurance Matchmaker Cari Gelber

    FEB 16

    Why the Perfect Time to Hire is a Myth ft. Insurance Matchmaker Cari Gelber

    "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 switchThe matchmaking process that goes way beyond resumes and why culture fit changes everythingWhy 99% of agencies say "we're not ready" to hire, and how Elevated+ is fixing thatHer 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

    54 min
  6. What Drives Insurance Agency Valuations ft. $19B M&A Expert Al Sica

    FEB 9

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

    "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

    50 min
  7. You Never Lose—You Either Win or Learn ft. Mike Stromsoe

    FEB 2

    You Never Lose—You Either Win or Learn ft. Mike Stromsoe

    "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

    48 min
  8. Run Your Agency Like It's For Sale ft. FirstChoice's Keith Captain

    JAN 27

    Run Your Agency Like It's For Sale ft. FirstChoice's Keith Captain

    "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 problemWhy 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

    45 min
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Ratings & Reviews

5
out of 5
2 Ratings

About

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, principals, and operators who want real leverage—better processes, better people, better outcomes. What you’ll get: Actionable hiring and ops strategies, culture-first leadership insights, and memorable stories that push you to think bigger and build bolder.

Information

  • Creator
    Elevate Teams
  • Years Active
    2025 - 2026
  • Episodes
    14
  • Rating
    Explicit
  • Copyright
    © 2026 Elevate Teams
  • Show Website
    Elevate The Hustle