She Left Real Estate Twice. The Second Time, She Did It Her Way | Megan VonDeylen episode artwork

EPISODE · May 11, 2026 · 48 MIN

She Left Real Estate Twice. The Second Time, She Did It Her Way | Megan VonDeylen

from Outside The Corporate Box · host J Squared

Megan VonDeylen got into real estate in 2008 during the market crash. She built her business over ten years, reached the top of her brokerage, then walked away because her family needed her. She went back into corporate, turned around departments faster than anyone expected, got passed over anyway, and then walked away again.The second time she returned to real estate, she made one decision that changed everything: she was going to do it as herself.No cardigans. No slipping into the persona her first broker told her to wear. Ball cap, boots, tattoos, and the kind of honest client communication that comes from someone who isn't spending energy managing their image.In this episode, Megan and the hosts talk through what it actually costs to rebuild something from scratch, why imposter syndrome hits hardest when you're most qualified, how she built a veteran-focused niche out of personal experience rather than marketing strategy, and why she's still working through the ceiling she built for herself inside her own brokerage.This is not a highlight reel conversation. This is what building looks like in the middle of it.Chapters:00:00 — Intro & Sponsor Welcome00:41 — Megan's Origin Story: Real Estate in 200803:38 — The First Exit: Corporate, PTSD, and Stability09:46 — The Second Corporate Run: Materials Management & Glass Ceilings14:36 — Coming Back: Who She Was vs. Who She Became19:07 — Results as Security: Leading from Shared Success22:27 — Why She Left Corporate the Second Time26:35 — Veteran Real Estate & Serving Those Who Served34:27 — The Real Cost of Building a Business36:29 — Imposter Syndrome, Self-Imposed Ceilings & Growing the Brokerage45:28 — The Last Question: What She Would Tell Herself on Day One46:17 — Where to Find MeganFOUNDING SPONSORS: 1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% offOutside the Corporate Box airs every Monday on all major podcast platforms and YouTube. Share this episode with someone who is in the middle of their own reinvention moment.Guest Bio:Megan VonDeylen is the broker and owner of Stone Realty Group in Michigan, a real estate educator, and a specialist in veteran homeownership. She entered real estate in 2008, built her career through two departures and two returns, and launched her own brokerage after nearly two decades in the industry. She holds a degree in accounting and a degree in finance and business management, both earned while simultaneously selling real estate, raising three children, and managing her household through her husband's combat PTSD. She mentored multiple agents to six-figure GCI in their first year and one to seven-figure GCI within five years. She is also a co-founder of a youth rodeo operation and an active advocate for veteran homeownership. Connect with Megan: https://meganvondeylen.com/Linkedin: https://www.linkedin.com/in/meganvondeylen

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Megan VonDeylen got into real estate in 2008 during the market crash. She built her business over ten years, reached the top of her brokerage, then walked away because her family needed her. She went back into corporate, turned around departments faster than anyone expected, got passed over anyway, and then walked away again. The second time she returned to real estate, she made one decision that changed everything: she was going to do it as herself. No cardigans. No slipping into the perso...

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She Left Real Estate Twice. The Second Time, She Did It Her Way | Megan VonDeylen

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