"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.

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

"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

"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.

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

"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.

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

“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.

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