Getting to Hell Yes! with Jason Hull from DoorGrow

There’s something instantly settling about Jason. He’s got that mix of calm confidence, curiosity & intention. The kind of person who’s seen the chaos of business up close and still believes in its beauty. You can feel the years of trial and teaching in every sentence.

When we first connected, we could have talked for hours about scaling property management companies, about why most entrepreneurs hit the wall between 200 and 400 doors, and about what happens when you build a business that doesn’t love you back.

This conversation wasn’t just about growth; it was about freedom.

“DoorGrow was built on thousands of mistakes.”

Jason laughs when he says that, but he means it.

He didn’t start out planning to coach property managers. In fact, it all began with a website.

“My brother bought a property management franchise back in 2008,” he told me. “He asked me to help with the website the corporation gave him. I looked at it and said, ‘This doesn’t look that great.’ I built him one and then all his fellow franchisees wanted one too.”

Before long, Jason’s web design business was ranking nationally for “property management website design.” But clients weren’t really buying websites; they wanted leads. They wanted growth.

“So we started focusing on growth,” he said. “And pretty soon, we became like Bar Rescue for property managers. We were redoing pricing, branding, systems, everything.”

That pivot became the foundation for DoorGrow: a coaching organization built specifically for long-term residential property managers. Not a tech company. Not a marketing agency. A growth lab for entrepreneurs stuck in the grind of a business they built but no longer love.

“The fantasy gets you started. Reality makes you grow.”

Pause for a sec. There are so many pitches to get started in real estate investing. They activate the fantasy, then you get to reality, and that can get very expensive.  

Every founder I know, myself included, starts with the same intoxicating mix of optimism and ambition. You can see the freedom you’re chasing. You just don’t see the boulder rolling behind you.

Jason’s version of that metaphor is pure gold:

“Remember Indiana Jones and the Raiders of the Lost Ark?” he asked. “He steals the statue and then the boulder starts chasing him. That’s entrepreneurship. Revenue is Indiana Jones. Expenses are the boulder. And the space between them? That’s cash flow.”

We both laughed, but it’s true and deadly accurate. Most business owners spend their early years making the boulder bigger without realizing it. More overhead. More complexity. More debt.

“Entrepreneurs don’t realize they keep adding to their burden,” he said. “They make decisions that make the boulder heavier, not the running easier.”

Jason’s framework for fixing that is deceptively simple: focus on four things every entrepreneur actually wants: fulfillment, freedom, contribution, and support.

But you can’t have any of those if you’re wearing every hat.

“The slowest path to growth is doing it alone.”

That’s one of Jason’s truths. Reminds me of the saying, “you can be rich, or you can be king, but you can’t be both.” 

He’s worked with hundreds of property management founders, the solopreneurs, the burned-out operators, the accidental landlords turned reluctant CEOs. And almost all of them think they can “figure it out.”

“I used to believe that too,” he said. “If I watched enough YouTube videos and read enough books, I could do it all. But that’s the slowest path to growth. Coaching collapses time.”

That phrase: “coaching collapses time” really got me thinking. I’ve been very lucky to have amazing coaches in my life.

Because it’s not about shortcuts; it’s about perspective. A good coach shows you where the system is broken, not where you are broken. Jason’s clients don’t come to him because they’re failing. They come because they’re stuck usually in that dangerous middle stage between 200 and 400 doors, what he calls “the second sand trap.”

“Most property management companies never get past that,” he explained. “It’s where the worst teams live. The systems aren’t mature enough to scale, but the problems are too big to ignore. That’s where DoorGrow helps people rebuild from the inside out.”

“If your business is a hell yes for you, it’ll be a hell yes for your clients.”

He said that near the end of our conversation, (I was closed!).

Jason’s philosophy on sales, leadership, and growth all orbit around one thing: alignment. Reminds me of Allan Klassen’s show and how he spoke about ‘clarity’. 

He teaches a framework called The Golden Bridge Formula. Connecting your personal why to your business why to your client’s why.

“Everyone expects everyone else to be selfish,” Jason said. “I just tell my clients how, if I’m selfish, it benefits them.”

It’s radical honesty that works.

He shared his own example:

“My personal mission in life is to inspire others to love true principles. I love figuring out what works and sharing it with others. That’s why I created DoorGrow to feed my addiction to learning and give me a vehicle to share what I learn. That’s why you can trust me. Because if I’m selfish, it means I’m going to help you grow. That’s my reward.”

That’s Getting to Hell Yes in its purest form, not by convincing but by connecting.

“Realistic goals are a grind. Impossible goals make you grow.”

Jason calls this his “Science of Scaling” mindset.

He challenges his clients to stop setting “realistic” goals based on their current level of thinking and instead create “impossible goals” that force the brain to innovate.

“Impossible goals are a playground for your mind,” he said. “They make your brain find new paths.”

He told me about a client named Darius who wanted to grow from 100 doors to 1,000 in a year — an impossible leap. Instead of working ten times harder, Darius started walking letters into his competitors’ offices, offering to buy their businesses. Within a year, he did.

“Impossible goals change the way you think,” Jason said. “It’s not about working harder. It’s about thinking differently.”

“Enjoy uncomfortable feedback.”

Of all the wisdom Jason shared today, that one is something I thrive on.

He told me about a coach who once said, “You’re one of my least coachable clients.” It gutted him. But he sat with it. Chewed on it. Let it shape him.

“I realized I was trying to please everyone,” he said. “I learned to value feedback that hurts. It’s how you grow fast.”

That’s become one of his leadership principles, building a culture where feedback is fuel, not friction. DoorGrow runs on a system Jason created called DoorGrow OS, a recognition-based operating rhythm that aligns personal wins with company goals.

“Most people aren’t motivated by money,” he said. “They’re motivated by recognition. Entrepreneurs forget that.”

Every week, his team shares their wins, gives each other credit, and publicly tracks progress toward goals. The cadence creates the culture.

That’s not just a management hack, that’s a life principle!

From my side of the mic…

Here’s what I’m still thinking about after this conversation with Jason Hull:

• Coaching doesn’t just accelerate progress, it collapses time.
  
• If your business isn’t designed to give you freedom, it’s a job in disguise.
  
• The space between the boulder and the dream is cash flow. Guard it fiercely.
  
• Realistic goals maintain; impossible goals transform.
  
• The only real objection in sales and life is trust.
  
• And maybe the most important one: if your business is a hell yes for you, it’ll be a hell yes for your clients too.
  

Jason reminded me that the goal isn’t just to grow a business, it’s to grow yourself through the business. When that alignment happens, everything else – the clients, the systems, the success starts to take care of itself.