Outside The Corporate Box
Outside the Corporate Box is for leaders, builders, and thinkers who knew they were never meant to stay inside someone else’s blueprint. Hosted by JMan and Jeffrey, this show explores what happens when ambitious professionals step beyond traditional titles, rigid systems, and inherited definitions of success to build a life and business that actually reflects who they are. These are conversations about reinvention, courage, identity, entrepreneurship, leadership, and the messy, beautiful work of becoming fully yourself. From executives who walked away from the boardroom… to creators who turned expertise into influence… to entrepreneurs who chose freedom over comfort… This is where modern thought leadership gets honest. Because sometimes the most powerful move isn’t climbing the ladder. It’s realizing the ladder was leaning against the wrong wall.
Episodes
Tezeta "Tez" Roro had everything the blueprint promised: the MBA, the six-figure salary, the recognized company name on her badge. She was so proud of that job she wore her badge to the grocery store. Then came 10:00 PM on a corporate campus, nine months pregnant, working through a capital budget crunch, and the moment she realized the structure she had spent 12 years climbing was fundamentally incompatible with the life she was ac...
Jackie Phichith spent nearly two decades inside Fortune 500 boardrooms helping McDonald's, Merck, and Pfizer navigate transformation. Then she realized the framework she had been teaching organizations was the same one she needed to apply to herself. What she learned next might change how you think about the career decision you are sitting on right now.
What You'll Learn:
1: Why 70% of enterprise transformations fail...
Lauren Dunkle Dlugosh was one of the top billing recruiters at her firm in Rochester, regularly placing $550K to $650K in fees annually. She had great colleagues, a strong reputation, and no real reason to leave. And the night before she quit, she slept perfectly.
That is what this conversation is really about. Not the business plan or the LinkedIn announcement. The moment before all of it, when everything felt right even th...
Donna Baker spent 30 years climbing the corporate ladder as an executive assistant — all the way to one of the highest-paid roles in Los Angeles. She was brilliant, organized, and on the verge of becoming a paper millionaire through stock options at an internet incubator.
Then the Nasdaq crashed in 2000, and within seven months she had no job and no stock.
At 50 years old, she got into real estate with zero clie...
Most episodes of Outside the Corporate Box feature guests who stepped away from someone else's structure to build their own thing. This one is different.
This week, JMan and Jeffrey Scott Stanton turn the mic on themselves.
For over a decade, Jeffrey was the Executive Vice President of Learning and Development at Douglas Elliman Real Estate, shaping the careers of 6,000 to 7,000 agents across one of the most recognize...
She started at the front desk of a small-town brokerage in 2005, took a pay cut to do it, and had no idea she'd still be there 20 years later — as co-broker owner.
Lindsay Hart is a licensed REALTOR and Co-Broker Owner at RE/MAX in Ithaca, New York, and the host of the podcast Under Contract Taking Backup. In this episode, Lindsay joins JMan and Jeffrey Scott Stanton on Outside the Corporate Box to talk about the slow,...
She walked away from a tech career, raised her kids while working weekends for a builder, and built her real estate business with doorknob bags and laundromat flyers because she had no marketing budget. Twenty-nine years later, Carrie J. Little is a managing broker in Illinois and Florida, a national speaker, bestselling author, and one of the most trusted educators in real estate technology.
In this conversation with JMan a...
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 ...
Eric Winegard didn't start his entrepreneurial journey until the age of 40. He was making $500,000 a year as a sales leader, living comfortably — and he walked away from all of it. Today, as CEO and co-founder of Rare Blue Moon Marketing, he runs an 8-figure digital marketing agency serving 300+ clients, built alongside his wife, and powered by an unshakeable belief in reinvention.
In this episode of Outside the Corpor...
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