From failing grades and scooping ice cream to running one of the top mortgage teams in Massachusetts — Kyle Regan’s comeback story is proof that the right mentor, mindset, and grind can change everything.

In this episode, Kyle shares how he:
• Grew up watching his dad in sales at WB Mason and caught the “professional friend-maker” bug early
• Struggled with school, grades, and depression, feeling counted out and underestimated
• Worked in warehouses, scooped ice cream, and waited tables — until one regular at Bertucci’s changed his life forever
• Got pulled into mortgages by a mentor who taught him mindset, real estate, and discipline
• Went sober at 24, putting down alcohol and drugs to give himself the best shot at success
• Built a half-a-billion-dollar branch, recruited 60+ people, and cleared $400K+ annually before age 30
• Rode the refi boom, sold the company, and faced his toughest years when rates spiked and his mom passed away
• Dug back into the fundamentals — cold calls, networking, goal sheets — and came back with his best purchase year ever
• Built a portfolio of multifamily properties and learned the power of real estate for long-term freedom
• Shares raw advice for anyone stuck in the “safe” route but hungry for more: find a mentor, ask better questions, and don’t let fear run your life

Guest: Kyle Regan — Mortgage Loan Officer
📍 Groton, MA
IG: @mortgageswithkyle

Timestamps:
00:00 Cold open — Kyle flexes making $400K before 30
02:10 Early jobs: Stop & Shop, scooping ice cream, Bertucci’s
07:50 Struggling with school, depression, and finding purpose
13:25 Meeting his life-changing mentor at a restaurant
19:40 Breaking into mortgages — the “get it done card” and learning on the fly
25:55 Sobriety, sacrifice, and building discipline
32:15 From $60K first year to $400K before 30
38:50 Building and scaling a 60-person mortgage branch
45:20 Riding the refi boom, selling the company, and losing his mom
52:40 Market collapse, losing momentum, and finding his grit again
59:25 Best purchase year ever — why hard work still wins in a tough market
01:04:10 Sales as relationships, real estate as wealth, and happiness as the real goal
01:09:30 Advice to the next “Bertucci’s kid” — take every shot, find mentors, and bet on yourself

Welcome to The Breakout Bunch — where real stories from real entrepreneurs come to life.

Hosted by Austen Tucker, this show cuts through the fluff and gets straight to the heart of what makes business owners tick. These are honest, unpolished conversations with self-made founders who are in it for more than just the money — they’re chasing purpose, impact, and something bigger than themselves.

New episodes weekly on Spotify, Apple, and YouTube.