"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