Elevate The Hustle

"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.

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

"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. They met at a golf outing in Nashville (where Dom barely made the tee time after "networking" until 3 AM), and what started as a round of golf turned into a years-long partnership. 

Rob breaks down: 

• Why he left a stable job at 50 to become an entrepreneur, and what finally pushed him to do it 
• The military leadership lesson that changed how he runs his agency 
• How he went from doing certificates of insurance himself (badly) to delegating outcomes, not tasks 
• Why most agencies are busy doing "busy work" instead of revenue-generating activities 
• The real reservation he had about hiring remote workers, and how it became a non-issue fast 
• What it's like preparing to sell your agency after only 5 years of going independent 

Plus, Rob shares his go-to golf club (a 15-year-old Nike hybrid), why he'll never do another certificate of insurance, and the one book every agency owner should read. 

If you've ever thought "I'm too old to start over," this episode is for you.

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

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

"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 of failure keeps people from starting, and why Kelly did it anyway 
• What actually drives people to leave their jobs (spoiler: it's not always money) 
• The "vibe check" that matters more than checking boxes on a resume 
• Why most agency owners are hiring the wrong people for the wrong jobs 
• How Stan finally convinced Kelly to stop working until 1 AM and hire her own VA, and what happened when she finally did 

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

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

“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 how they do business.

From there, Dom takes you back to the early days:
- Starting an insurance agency from scratch in New York
- Working 70–80 hour weeks and burning out
- Trying offshore help in India and realizing what doesn’t work
- Discovering Latin American talent and building a hybrid team that helped him scale and eventually sell his agency.

Stan and Dom break down how that experience turned into Elevate Teams—matching insurance agencies with trained, vetted virtual assistants from Latin America—and why they believe delegation, process, and culture are the real unlocks for growth.
 
They also dig into:
- The simple exercise that showed Dom he was doing “intern work” as the owner
- Why most agency owners stay stuck in the weeds
- Why sometimes, in business, you have to do something so bold people can’t forget you (like, say, rolling a giraffe into a ballroom)
 
The episode wraps with a rapid-fire round so you can get to know them—golf handicaps, Jets fandom, guilty-pleasure Starbucks orders and all.

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

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