From Bertucci’s Waiter to $400K Before 30 — Kyle Regan’s Mortgage Come-Up

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

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.

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