Earlier this year, I began a journey. I set out to interview entrepreneurs who had achieved something extraordinarily rare: breaking through $500 million in revenue, with many going on to scale their companies past $1 billion. So far, I’ve spoken with about 20 CEOs who have done it, and the lessons emerging are profound.
I’m drawn to this stage of growth because the divide between “entrepreneur” and “enterprise” is wide. There are millions of books written on entrepreneurship, most aimed at founders looking to reach $100 million. There are also thousands of MBA programs and case studies on enterprise management once a company has already surpassed the $1 billion mark.
But the path in between? The evolution from entrepreneur to enterprise? The critical leap from $100 million to $1 billion? That path is less studied and even less understood.
And maybe that’s why so few make it.
The Odds Are Against You
McKinsey & Company studied 3,000 high-tech companies and found that while nearly 30% reached $100 million in revenue, only 12% of those went on to $1 billion. That’s just 3% of the total pool. Think about that: if you are leading a company that has reached $100 million in revenue, your odds of reaching $1 billion are slimmer than 1 in 10.
McKinsey’s dataset included tech giants like Adobe, Amazon, Nintendo, and Tencent, but I suspect the pattern holds across industries. The lesson is clear: as hard as it is to scale a business to $100 million, turning that business into a billion-dollar enterprise is even harder.
And yet, it can be done. Some leaders figure out how to cross this chasm. The question is—how?
Over the coming months, I’ll continue to explore this question. The work will culminate in a book I’m co-authoring with Verne Harnish. We’re also beginning to convene growth officers of sub-$1 billion businesses through our new Outthinker Growth Network. This peer community is designed specifically for this stage of growth, much like our existing Outthinker Strategy Network is for multi-billion-dollar enterprises.
Because here’s the truth: if you can decode the patterns, if you can learn how billion-dollar insights are formed, your odds of joining the rare 3% rise dramatically.
The Power of the Billion-Dollar Insight
The first and most consistent theme emerging from my interviews is this: every founder who built a billion-dollar company can point back to a pivotal insight.
These are not just clever ideas. They are revelations big enough to support the weight of a billion-dollar business. And remarkably, the process of generating these insights is not random. Patterns emerge. They can be repeated. In fact, I believe they can be engineered.
Take Brian Scudamore, founder of 1-800-GOT-JUNK?, now generating more than $1 billion in system-wide revenue. His billion-dollar insight came not in a boardroom, but in a McDonald’s parking lot. Broke and uncertain, he spotted a beat-up junk removal truck. He realized there was an overlooked opportunity to professionalize a “dirty job.” That was the seed.
Or Matt Wallach, co-founder of Veeva Systems, now a $2.5 billion enterprise. His insight came from listening to customers at his then-employer. Their tech teams were asking for features he knew their users wouldn’t really want. His company kept saying “yes.” He said, “What if we give them what the people on the ground actually want?” The insight into verticalized enterprise software became the foundation of Veeva.
Neil Balter, founder of California Closets, had his insight on an airplane. He realized people weren’t just buying cabinets; they were buying a lifestyle. That shift in framing unlocked exponential growth.
And then there’s Radek Sali.
Case Study: Swisse Wellness
When Sali took over as CEO of Swisse Wellness, it was a small Australian vitamin company with $15 million in revenue and about 30 employees. Ten years later, he scaled it to $650 million and sold it for nearly $2 billion.
Where did his insight come from? Not from spreadsheets or strategy decks, but from walking the aisles of pharmacies.
He noticed two things.
Insight 1: Aspirations, not claims.
The entire industry marketed vitamins through scientific claims: “supports collagen production,” “aids energy metabolism,” “contributes to immune system health.” But customers weren’t buying science. They were buying aspirations: to glow, to thrive, to live longer.
Sali rebranded Swisse products around higher-order desires, such as Beauty & Self-Confidence, Health & Longevity, Energy & Performance. He shifted the language from chemistry to identity.
Insight 2: Recognition beats quality.
Talking with pharmacists, he assumed Centrum dominated shelf space because it paid more or offered better products. He was wrong. Centrum simply sold more because it was better recognized. Recognition drove sales. Sales earned shelf space. Shelf space fueled recognition. It was a flywheel powered by bold marketing bets.
Sali realized Swisse was underinvesting in brand awareness. He pushed for celebrity endorsements and major partnerships, including with the captain of the Australian national rugby team who was so influential he was called “the second most powerful man in Australia.” Swisse surged. Expansion into Asia followed, built on the same formula.
Was this luck? No. It was insight, engineered by immersion in the customer’s world.
Can We Engineer Billion-Dollar Insights?
The good news is yes. We can.
In 1926, Graham Wallas, a professor at the London School of Economics, published The Art of Thought. He described the creative process in four stages:
- Preparation – immersing yourself in the problem, gathering inputs.
- Incubation – stepping away, letting the subconscious connect the dots.
- Illumination – the insight emerges, sometimes in fragments, sometimes in a flash.
- Verification – testing and refining the idea until it works.
Sali’s story, along with those of Scudamore, Wallach, Balter, and others, fits this model perfectly. These founders immersed themselves, let ideas incubate, recognized when sparks appeared, and then verified through bold execution.
The Entrepreneur-to-Enterprise Gap
Here’s where the connection to scaling comes in. At $100 million, most companies are still led by entrepreneurs. Strategy is driven by intuition, by founder vision, by hustle.
At $1 billion, companies operate as enterprises. They have systems, teams, and processes that institutionalize insight generation. They don’t wait for lightning strikes; they engineer storms.
The gap in between is perilous. Too many companies stall because they haven’t yet learned how to make insight-generation repeatable. They rely on the founder’s instincts long after the scale requires a broader system.
That’s the unique challenge of the $100M to $1B journey: shifting from relying on individual flashes of genius to building organizational muscles that continuously surface, test, and scale insights.
Steps You Can Take Today
If you’re leading a company on this journey, here are four practices to increase your odds of crossing the chasm:
- Collect relentlessly. Get out of the office. Walk your customer’s aisles. Observe. Ask questions. Don’t filter too soon.
- Activate incubation. Build space into your days for the Default Mode Network: bed, bath, bus. Let your mind wander.
- Capture sparks. Write down fragments of insight as they come. Notice when patterns converge.
- Test fast. Build prototypes, run experiments, iterate quickly. Treat insights as hypotheses to be validated.
The more inputs you gather, the more sparks you catch, the more tests you run and the higher your odds of engineering your billion-dollar leap.
The Path Forward
I believe the journey from $100 million to $1 billion is not a mystery. It’s a discipline. A way of seeing. A set of practices you can adopt today.
Over the next year, I’ll continue to interview the leaders who’ve made this leap. I’ll share what I learn along the way, and the work will become a book. In parallel, we’re building the Outthinker Growth Network to help leaders like you: ambitious, sub-$1 billion companies with billion-dollar aspirations.
The gap between $100 million and $1 billion may be wide, but it is not uncrossable. With the right insight, the right system, and the right mindset, you can make the leap.
And when you do, you’ll find that the billion-dollar journey isn’t the end. It’s just the beginning.
Explore the strategies that help leaders cross the $100M–$1B chasm. Visit Outthinker.com today.