By most measures, Jason Green had made it. Multiple businesses built. Multiple exits. His latest company is growing steadily, and turnover is climbing, with a team around him doing the work. From the outside, it looked exactly like the kind of entrepreneurial success people spend years chasing, but inside was a different story entirely.
By the time Jason found what he was looking for, he had spent nearly a decade building something that was quietly draining everything from him, even though it didn’t show up on a balance sheet.
In this episode of Unfiltered with Brij, Jason Green, certified EOS implementer, sits down with Brij Thankey for a conversation that moves quickly beyond business success and into something far more honest. Having built and exited multiple companies himself, Jason knows what it feels like when growth comes at the expense of everything else.
His story isn’t about building a bigger business. It’s about finding a way back to the life he thought entrepreneurship would give him. Some founders talk about struggle in the past tense, like a chapter safely behind them, but Jason Green talks about it the way someone talks about something they still feel in their bones.
A Decade Inside the Trap, Six in Denial
Jason has built and exited multiple businesses. By the time he found what he was looking for, he had spent roughly ten years inside what he now calls the TRAP.
The early years were energising, with a small team, plenty of momentum, and the particular clarity that comes with building something from nothing. That carried him through the first couple of million in turnover.
Then the business grew past what energy alone could sustain, and that is where it got complicated.
More people on the team meant more responsibility, heavier payroll, decisions coming at him from every direction, and a growing pressure that followed him home, where he was supposed to be fully present but never quite was.
“Not wanting to get out of bed in the morning… it was just a really oppressive weight.” — Jason Green.
He was in the business every day. There at home, sometimes, but mentally, as he now admits, he was somewhere else entirely, unable to put it down, unable to separate himself from it, carrying the company into every part of his life, whether he meant to or not.
“I may have been there in body. But I wasn’t there with my heart and my mind.” — Jason Green.
How Jason Green Found a Way Out
For years, Jason’s response to the pressure was the same: work harder, move faster, and take on more responsibilities. Which is what most founders do, and as Jason says, is the wrong answer when the real problem isn’t effort.
“I was on a little mouse wheel, working harder, running faster, expecting things to change, doing the same thing over and over again.” — Jason Green.
He was one of the most involved people in his own company, hands in everything, present at every decision, unable to delegate and unwilling to let go. Which turned out to be the problem.
What eventually broke the pattern was serendipity: a business exhibition led to an invitation to Florida, led to a conference in Philadelphia, which led him to a book called Traction, which he read cover to cover on the flight home.
He walked into the office the next day, slammed the book down and told his team they were doing this. They rolled their eyes because they were used to seeing him return from conferences with new ideas before. But this time, something was different.
The Real Reason Founders Stay Trapped
Jason now sits with founders every week, and he watches the same pattern repeat itself across rooms, industries and company sizes. Intelligent people, capable builders, the evidence right in front of them, and still they wait years to see it.
When asked why, his answer was direct, ego. That quiet belief that tells you needing help is a sign of weakness, and that the right answer is always one more push away.
“It was about, I know best. I can figure this out. I don’t need anybody’s help, and if I do, that’s just a sense of weakness.” — Jason Green.
Breaking through that, he says, is where everything begins, and it doesn’t start when the right framework arrives, but the moment the founder is honest enough to name what they’ve been avoiding by saying, “I am the ceiling.” The person holding the business back is the same person trying to fix it.
What it Feels Like to Finally Breathe
What EOS gave Jason isn’t really a system; it was space, and for someone who spent years suffocating inside a business they built, that distinction mattered more than any framework.
“It’s almost like being business asthmatic. It just gives you space. And that space opens your mind to your own development, your business’s development.” — Jason Green.
The business that once needed him for everything gradually became able to run without him. He started choosing who he worked with, started seeing the impact of his work stretch beyond his own walls, and for the first time in years, he genuinely enjoyed it.
When Brij asked what success feels like to him now, his answer came without hesitation: “Happiness.”
Watch or Listen to the Full Conversation
This article only scratches the surface of what Jason and Brij explore together. From founders’ burnout and decision fatigue to EOS, and building businesses that create freedom instead of consuming it, this is a conversation that will resonate with anyone carrying the weight of growing a company.
If you’ve ever felt trapped inside a business you once loved, this episode is worth your time.
Watch the full episode on YouTube, or listen on Spotify and Amazon Music.
More conversations like this are coming. Find everything at brijthankey.com
