Want to Scale? This is the Way to Entrepreneurial Success

September 22, 2026

Published in:

Business Strategy & Growth

Barry Raber sits on a park bench with his cell phone and dog. — Barry Raber and Ripley. Photo courtesy Barry Raber

“Oh wow, that’s it! That’s the answer.”

“Every entrepreneur I know who scaled way up and eventually exited for millions did this exact same thing. Holy moly — that’s it! And if that really is it, then all the entrepreneurs in my scaling cohort have to do is that one thing.”

I literally stopped in my tracks when I had this epiphany.

I was walking my friendly Labradoodle, Ripley, on a trail through the woods, listening to an audiobook. I stopped and rewound the recording 60 seconds to hear it again. Then I listened one more time. And then a third.

I couldn’t believe it: That’s it. The one big idea.

I wasn’t looking for it, and I didn’t even believe there could be such a simple answer to the question I had been studying for years: What separates the entrepreneurs who build something good from the ones who scale way beyond what initially seemed possible?

I sat down on a nearby bench and started thinking through the path of every highly successful entrepreneur I knew.

I’ve been a member of EO Portland for 24 years—longer than anyone else currently in the chapter. During that time, I’ve probably met, heard speak, participated in workshops with, or otherwise been exposed to 500 entrepreneurs. I’ve also spent years reading about many more.

So, I started mentally clicking through the people I knew who had scaled beyond Portland and eventually cashed out for multimillions.

"If your goal is simply to build a good business, there are lots of ways to do that. But if you want to build something exceptional, start by choosing a destination that your current business has no idea how to reach."

— Barry Raber, EO Portland

Eric? Yep.

Dave? Yep.

Kim? Andrew? Roger? Tom? Jill?

Yep, yep, yep, yep, yep.

Travis? Mike? Paul?

Same.

Then I thought about my own history.

Yep. I had done it too, with the same kind of outsized result.

For the past three years, I’ve been researching and writing articles for business magazines, interviewing entrepreneurs, and trying to understand what works and what doesn’t. Yet somehow this idea—which suddenly seemed incredibly obvious—had never occurred to me.

And I wasn’t even looking for it. It just showed up.

Then I reversed the test. I thought about entrepreneurs I knew who had built good businesses but had not experienced that level of financial success. At least among the people whose stories I knew well, the pattern held. They did not set the Impossible Goal.

Now I was convinced.

This was the answer.

The Search for the Scaling Formula

Earlier this year, I helped form an eight-entrepreneur scaling cohort in Portland. Our goal is ambitious: To help these companies grow from where they are to $20 million-plus in annual revenue within three to five years.

To prepare for co-leading the group, I read everything I could find about scaling and revisited the teachings of many of the best-known thinkers in the space: Gino Wickman and Traction/EOS, Verne Harnish and Scaling Up, Dan Sullivan and Strategic Coach, Jim Collins and Scale or Fail, and others.

All of it contained useful ideas, many of which I used.

The cohort was two meetings into the year and working through strategic growth plans when an EO Portland member, Ryan, attended EO’s Entrepreneurial Masters Program (EMP) at Harvard. He emailed my co-leader, Richard, and me saying he had just heard Ben Hardy speak and thought Hardy’s latest ideas might be worth sharing with our scaling cohort.

"The idea that grabbed me was remarkably simple: Set an Impossible Goal!"

— Barry Raber, EO Portland

Ryan described it as “pretty good” and a fresh take on scaling. That turned out to be a considerable understatement.

Richard and I immediately ordered Hardy’s book, The Science of Scaling, and read it that week. I listened to the audiobook while walking Ripley.

And that was when I stopped dead on the trail.

The idea that grabbed me was remarkably simple:

Set an Impossible Goal.

After finishing the book, it was clear that we needed to get this into the hands of every member of our group immediately and discuss its main ideas at our next meeting.

Which is exactly what we did. And, to a person, the book and its central premise resonated the same way.

Why This Is Different

Most books, experts, and systems on scaling teach you how to scale. They give you processes, systems, scorecards, meeting rhythms, hiring strategies, and execution tools.

Those things matter.

But Hardy’s premise struck me as different because it starts one level higher. Before worrying about how to achieve your goal, choose a goal so large that your existing way of operating cannot possibly get you there.

That changes everything.

If your goal is incremental, you can probably accomplish it by working a little harder and improving what you already do. An impossible goal doesn't allow that. An impossible goal forces a new dynamic in your company:

It forces you to rethink the business.
It forces you to stop doing small things that consume your time but will not get you where you are going.
It forces you to develop capabilities you don't currently have.
It forces you to find people, systems, capital, relationships, and knowledge that don't yet exist inside your organization.

Most importantly, it forces you to become a different company.

Another Realization: I Did This, Too

Years ago, I set what felt like an impossible goal for my Bargain Storage business: Acquire 30 properties in three years.

At the time, I had very little idea how we were going to do it. We had almost none of the infrastructure necessary to accomplish something that large.

So, we had to build it.

We had to learn 10 western U.S. markets. We had to develop broker relationships in all those cities so we could find the best deals. We had to start a property management company from scratch and hire great people who could then hire other great people. We needed a CFO. We had to raise $10 million from 20 partners. And on and on.

Almost none of that would have happened if I had set a comfortable goal. Had the goal been to acquire three or four properties, we could have kept doing essentially what we were already doing.

Thirty properties required us to become something entirely different.

In retrospect, being somewhat naïve about how much work would be involved was probably a good thing. Pairing that naïveté with a goal that felt beyond our capabilities forced us to figure out things we otherwise never would have attempted.

That, I now realize, was the formula.

This Is Not for Everyone

Not every entrepreneur wants this.

Some are perfectly happy building a smaller, more local company, and there are enormous advantages to doing that. I wrote about those advantages in Bigger Is Not Always Better.

Scaling way up requires sacrifice, particularly in the short term.

For me, though, that challenge is fun. It is invigorating. And organizations like EO provide the peer support, perspective, and tools that make the journey much less lonely.

Our Portland scaling cohort revised the plans and goals we had already been developing. In some cases, those plans had essentially been finished.

We made them bigger.

Much bigger.

Maybe it was just good timing that Hardy’s book showed up exactly when it did. I tend to think it was something closer to divine intervention. I have had a few moments like that in my life—when the right idea appeared at precisely the right time.

I believe this was one of them.

Five to seven years from now, we will know whether I am right.

But after sitting on that bench and mentally running through decades' worth of entrepreneurs, I am willing to make a pretty big bet on it.

If your goal is simply to build a good business, there are lots of ways to do that.

But if you want to build something exceptional—something with a much bigger impact, something far beyond what your company appears capable of today, and potentially something that creates a life-changing exit—start by choosing a destination that your current business has no idea how to reach.

Then figure out who you have to become to get there.

As The Mandalorian says:

This is the Way.

Contributed by Barry Raber, EO Portland, who is president of Carefree RV Storage and Bargain Storage, the founder of Business Property Trust, and an EO Portland Entrepreneur of the Year. He shares his successful business secrets at Real Simple Business.