My Story — Why I Built iBD
My nIndependence by Design™ the founder of Independence by Design™.
Before you go deeper into the system, I want to give you the full story behind it. Not the highlight reel — the raw truth. Because if you’re an owner-operator, you deserve to know that the person teaching you has lived the same chaos you’re trying to escape.
Growing Up Searching for the Bigger Picture
I grew up in Mahtomedi, Minnesota, and for as long as I can remember, there were two questions that wouldn’t leave me alone: Why are we here? What’s the point?
If I couldn’t answer those questions, I checked out. I got C’s and D’s in school. I got a D in economics and a C in math — which is hilarious because I now talk about monetary policy, macroeconomics, and business finance for a living. But that’s the thing about entrepreneurs: when we have context to the goal — when we know what the game is and how to win — we can execute like sons of guns. Without that context, we rebel.
I put my soccer picture in the original video because it captures this perfectly. When I know where the goal is and how the game works, I’m relentless. Every owner-operator I’ve ever met is wired the same way. That entrepreneurial seizure Michael Gerber writes about in The E-Myth — getting sick and tired of someone telling you what to do, and deciding you’d rather take all the risk and work 80 hours a week to control your own destiny? That’s me to a T.
My Dad Mortgaged Our House to Buy Copiers
My real entrepreneurial journey started with my dad. He barely graduated high school, crushed it in sales, and then mortgaged our family home to buy 300,000 worth of Panasonic copiers. I was in elementary school. He had one employee. It was the early nineties.
He always told me: “You can do whatever you want, Ryan.” And he meant it — because he was living it. He wanted his own company, his own destiny, his own independence.
Every night at nine o’clock he’d come home and I’d hear the play-by-play — getting the Canon license, moving locations, hiring people. Those people became part of our family. They came on hunting trips and fishing trips. I had internships selling copiers at 19 and water units when we decided to get into water, which was a bad idea.
The company became very successful. We hit the Inc. 500, the Fastest 50, grew to $21 million in revenue. I worked in and around that business my whole life.
I Swore I’d Never Work for My Dad
My dad and I are oil and water — very similar, very different. Still best friends. He lives five minutes down the road. But I am professionally unemployable. I have a visceral reaction to people telling me what to do, especially my dad. I swore on my grave I’d never work for him or any family business.
Then 2009 happened. I graduated from St. John’s University. The world had taken a shit. The 98% placement rate inverted to 2%. I was probably one of the only people out of all my friends with a job offer because I was willing to work for $1,500 a month. The GM recruited me to be a “solutions sales person” — which was just copiers with a fancier name.
As a second-generation family member, you have two options: be the entitled prick everyone thinks you’re going to be, or work twice as hard to earn the same level of respect everyone else already gets. I started in sales because numbers are objective. I made more phone calls than everyone. I exceeded quota and made real money selling copiers while everyone I graduated with was broke. I liked making money and I loved being responsible for my own destiny.
Then I got pulled into the bank and CPA meetings.
We Lost 21 Million of Revenue
I’ll never forget sitting in that bank meeting with my dad. We lost 21 million in revenue. Bad deal.
There were a lot of reasons — the financial crisis, industry margin compression, a manufacturer distribution model where everyone had your money but you. But the primary reason was that my dad had been distant from the company for about five or six years going through personal stuff. There was a ton of cash flow in the business for years on the equipment and service margins, and he just wasn’t going into the office. The GM was running things. There was no ownership operating system in place — which is exactly why I built what I’m talking about now. We were focused on top-line revenue and gross profit, and everything else was out of whack.
When you hear that news in a bank meeting, you only have so many choices. For the next six years, it was the bank versus us. Hit the $240,000 payroll every other Thursday. Collect receivables. Push off payables. Turn inventory. Make sure there was cash in the bank when the wire hit. We’d make payroll, immediately get in the car, drive to the cabin in Wisconsin, and pound Captain Morgan. Then do it all over again.
My dad’s visual still sticks with me: “I feel like I’m driving a dump truck full of water down the highway, and we hit the brakes, and everything just came right over us.”
That’s exactly what happened.
Rebuilding Through Grit and Zero Margin for Error
The real entrepreneurial spirit is that you just never give up. Your options when you’re in that deep are stark: do a fire sale, shut the doors, eat the personal guarantees, and tell 115 families that depend on you it’s over? Or do you gamble it all — double down on personal guarantees, scrounge for every penny, and keep the machine going?
We kept the machine going. With duct tape, grit, and no line of credit.
We built an org chart from scratch. Sold two branches for cash. Installed a new ERP system — $350,000, total nightmare. Changed comp plans. Launched managed IT services. Rebranded the entire company. I fired 55 people by the time I was 25. We won the Minnesota Wild as a full technology provider — one of my favorite wins of the entire journey. I read Delivering Happiness and we built a culture that went from toxicity to one of the best teams I’ve ever been part of. People I still talk to today.
I tried to quit three times. My dad and I fought constantly. My wife would find me crying at home because we were fighting with the bank and fighting with each other and the weight was unbearable.
But we were also making serious progress.
The Conflict That Broke Us
As I was effectively running operations as EVP — the integrator and the visionary rolled into one — my dad and I kept bumping into each other’s needs.
I wanted to reinvest. I had a vision of a $100 million multi-state technology company. We’d already put a few million dollars back into IT services and software automation.
My dad wanted more distributions. He was sick of it. He wanted to retire.
We were arguing over reinvestment versus distributions because our cash flow and our time were all commingled together. Employees had opinions. Family members had opinions. My parents were going through a divorce in the middle of all this. Our Vistage peer group had opinions. Canon had opinions. Consultants pretended they could solve everything. Customers could never know any of this was happening. We had no wealth manager because we had no liquid wealth. We had no CFO — just controllers juggling cash flow and a CPA who was one of the dominoes that started this whole chain.
And our banker was my mortal enemy.
That right there — the landscape of advisors and stakeholders all pulling in different directions with no unified framework — is why I created this system. If you’re an owner-operator with a job and an asset, throw in one partner or two and it gets convoluted incredibly fast.
We Sold to Escape the Trap
The feeling of being trapped was the exact opposite reason we became entrepreneurs. You can see the opportunity, but you’re stuck. It was exhausting. After years of fighting and rebuilding and getting to a healthy seven-figure trailing twelve months of EBITDA, we sold to Loeffler in 2014. Great company — most of my employees are still there.
It was a multi-eight-figure deal. And it was one of the hardest days of my life.
We signed the purchase agreement, went back to the office, and told 90 employees they had to interview for their jobs. Only 34 got positions. College buddies of mine. People who went on my bachelor party. People who’d been coming to our family get-togethers since I was twelve. Stan, who’d been with the company forever. All the barbecues, the President’s Club trips, the charities we supported together — all of it, gone in a day.
The day we got an eight-figure bank wire, I had to fire 60 of my employees. I went home, sat on my bed, and bawled my eyes out. My wife sat next to me and I just kept saying: “What the hell was that?”
My entire identity was tied to that business. And in one day, it disappeared.
75% of Owners Are Unhappy After They Sell
Shortly after, I read a book by Bo Burlingham — the editor of Inc. Magazine for years, author of Small Giants and Street Smarts. Out of interviewing 300 owners, he found that 75% were unhappy 12 months after they sold, regardless of how much money they made.
I didn’t need a statistic. I was living it.
What he discovered is that owners didn’t know who they were, what they wanted from their business, and why. That resonated so deeply it changed the trajectory of my life.
I lasted 60 days at the buyer’s office. They were great to me, but I’m professionally unemployable — I have a visceral reaction to being told what to do unless I know the purpose and the game. So I quit and went on a mission: what could I have done differently?
The Eleven-Year Search
That mission has now spanned eleven years. I started a podcast — now over 460 episodes — interviewing the smartest owners, operators, and experts I could find. I became a wealth manager for a couple years, which was my least favorite thing I’ve ever done, but it taught me how money actually works. That was the chain of events where the lightbulb went on: our business is an asset. Private equity. Cash flow. Valuations. Business operations plus investment thinking. It was like a series of bells going off.
I built a consulting firm doing business valuations and growth/exit planning — and quickly learned I’d engineered a business nobody wanted to work with, because the word “exit” attracted people who wanted to put lipstick on a pig and repelled the people who actually wanted to grow.
I kept learning. Gina Wickman. John Warrillow. Mike Michalowicz. Chris Voss. Jack Stack. I launched a CFO services business because I fell in love with the lens of financial modeling — seeing future cash flow, distributions, and valuation as an integrated picture. Hit seven figures. Got out of that in early 2024 because I’m not built to run a professional services firm where you’re constantly reinvesting to hit other people’s payroll.
Through all of it, I ran workshops for EO and Vistage. Over 3,000 business owners went through those workshops. I won the Vistage Top Speaker Award. And the reason I mention any of that is because I’ve been testing the ideas inside this system for over a decade, in front of real owners, with real businesses, in real time.
What I Learned
The pattern became unmistakable: owners don’t fail because of strategy. They fail because no one helps them understand the relationship between their time, their cash flow, and their wealth — and how to design the business to serve those goals intentionally.
We had every advisor imaginable — CPA, banker, wealth manager, consultants, peer group — and still no clear path. Because none of them were operating from a unified framework. We were trying to solve an ownership problem with business tools, and it doesn’t work.
Business operating systems — EOS, Scaling Up, OKRs, Great Game of Business — they’re incredible for running operations. I love them. But they don’t ask you what you want out of your time, cash flow, and wealth. They don’t use those goals as the frame of the puzzle. They go straight to strategy, growth, and scaling — and then you’re three years in wondering why you’re burnt out and your cash flow still doesn’t make sense.
The iBD Ownership OS™ is the foundational layer that was missing. It’s the system that sits above the business operating system and governs it from the owner’s perspective. Your time, your cash flow, your wealth. Your business as an asset. The private equity meets family office playbook that allows you to extract yourself from the operations, reach Independence Escape Velocity™, and run the company from the boardroom with complete optionality.
Why I Believe Business Is Worth It
I’ll end with something that might sound philosophical, but I mean every word of it.
I think owning a company is one of the most amazing vehicles for realizing your truest potential as a person. Alan Watts. Joe Dispenza. Carl Jung. The thinkers I keep coming back to all point at the same truth: experience is the point. We have a finite amount of time, and if we can come up with a noble aim — a goal that’s truly ours — and orient everything around it, the business becomes a platform for self-authorship instead of self-destruction.
That’s what I wish I had understood before we sold. Not just the financial math, but the deeper question: What do I actually want? What are the choices? How do I get aligned with my partner, my family, and my goals so that the business serves all of it?
I believe there’s a world where you come up with your goal, push it down through the operations, and build a business that allows you to reach independence — whether you scale, step back, or sell — and not regret it.
That’s exactly why I created the iBD Ownership OS™.
What Comes Next
In the next lesson, I’ll walk you through the system itself — the Ownership Operating System, its three phases, and how it all fits together. That’s where the framework becomes tangible.
See you in the next one.
Connections
OS Overview: [[iBD Ownership OS — _Concept Libraryship OS™]] Production System: Canon Production Checklist, _Concept Library