The Man Behind Two Unicorns and the Hard Lessons That Come With Them

Most founders spend years chasing billion-dollar company success without ever stopping to ask what they actually want from the journey.

Jason Cohen built not one, but two billion-dollar companies — SmartBear and WP Engine — and he will tell you directly that the biggest mistake founders make has nothing to do with product, marketing, or fundraising.

It has everything to do with a choice most founders never consciously make.

The choice between being rich and being king.

And if you have never sat down and decided which one you truly want, there is a very real chance you will end up with neither.

That is the warning Jason carries with him every time he speaks to founders, investors, and startup communities around the world in 2026.

He is not speaking from theory — he is speaking from two full cycles of building, scaling, and navigating the emotional minefield that comes with running a company worth billions of dollars.

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What “Rich vs. King” Actually Means for Founders Building Billion-Dollar Companies Today

The Framework That Started It All

The phrase “Rich vs. King” did not come from Jason Cohen — it actually originated with Harvard Business School professor Noam Wasserman.

Wasserman’s research showed clearly that founders face a fundamental trade-off: you either optimize for being rich, meaning you prioritize the financial outcome above all else, or you optimize for being king, meaning you prioritize control and staying at the helm of the company you built.

His research also showed something even more alarming — founders who never consciously choose between the two almost always end up with neither outcome.

They stay too long hoping for a bigger payday, or they sell too early because they never defined what they were actually building toward.

Jason took this framework seriously, and it shaped every decision he made at SmartBear, his first billion-dollar company venture, from the very first hire.

Before anyone signed an employment agreement at SmartBear, Jason sat them down and told them plainly that the plan was to sell the company eventually.

He was not itching to get out.

He was not running from something.

But if a good offer came along, they were going to take it — and everyone with equity was going to benefit from that moment together.

Why Transparency About the End Game Changes Everything

Most founders treat the question of selling as something to figure out later, as a back-burner conversation reserved for the moment a buyer shows up with a check.

Jason flipped that completely on its head, and it made SmartBear’s culture cleaner, sharper, and more aligned from day one.

By telling people upfront that the company had an intentional endpoint, he attracted the kind of employees who were motivated by the mission of building something valuable rather than people who wanted a forever home.

It is a subtle but powerful difference, and it is one of the core reasons SmartBear grew into a billion-dollar company acquisition target in the first place.

He described his approach with a quiet confidence: “If you want to join a little company and stay there for 20 years, that is amazing, but it is just not this company at all.”

The people who joined SmartBear after hearing that were self-selecting into a shared vision.

They understood they were building something great with the intention of one day releasing it into the world and walking away richer for it.

And paradoxically, that clarity made everyone work harder, not less.

The Box Game: The Simplest Tool for the Hardest Founder Decision

How Jason Cohen Decides When to Sell a Billion-Dollar Company

When the time came to evaluate whether to sell SmartBear, Jason did not build a complex financial model.

He did not hire an investment banker to run scenarios on a spreadsheet for six weeks.

He invented something he calls the box game, and it cuts through every noise-filled conversation about valuations, multiples, and market timing with a kind of brutal simplicity that most founders are not used to.

Here is how the box game works.

You have two opaque boxes sitting in front of you, and you have to pick one.

Box A contains ten million dollars, guaranteed, no conditions, no catches.

Box B contains either twenty million dollars or nothing at all, with a fifty-fifty chance of each.

You pick one and you live with whatever is inside.

The question Jason asks every founder who plays the game is simple: which box do you want?

Why Almost Every Founder Chooses Box A (And Why That Is Usually Right)

The answer, for most founders, is Box A — the guaranteed ten million dollars.

And Jason says that is almost always the correct answer, for one very specific reason.

Ten million dollars moves you across what he calls the freedom line.

The freedom line is the point after which you can do whatever you want with your life — start another company, travel, invest, support causes you believe in, spend time with your family — without money being the constraint that shapes your decisions.

Below the freedom line, every choice you make is filtered through financial survival.

Above it, you are free in a way that very few people ever experience.

The difference between ten million and twenty million dollars does not meaningfully change your life if you are already above the freedom line.

But the difference between ten million and zero changes everything.

That is why Box A wins almost every time for a founder who has not yet crossed that threshold.

Jason used this exact framework when SmartBear received its acquisition offer, and he chose Box A.

The deal was done.

The fax machine printed the final signed page.

And then something completely unexpected happened.

He felt sad.

The Emotional Reality Nobody Tells You About Selling a Billion-Dollar Company

Your Brain Treats Your Company Like Your Child — Science Confirms It

Jason Cohen felt sadness the moment the SmartBear deal closed, and he did not know what to do with that emotion.

He had made the right financial decision by every rational measure.

He had achieved the goal he set out to achieve.

And yet, he sat in front of a fax machine feeling a grief he had not prepared for.

What Jason later discovered is that this reaction is not only normal — it is predictable, documented, and rooted in actual neuroscience.

A study using MRI brain imaging showed researchers something remarkable when they put founders in the scanner and showed them various images.

When founders looked at landscapes or neutral images, their brains settled into a calm baseline state.

When they were shown pictures of their children, their brains lit up in a specific pattern associated with parental attachment.

And when they were shown the logo of the company they founded — just a logo, nothing else — their brains did not just activate.

They activated in the exact same pattern as when they saw their children’s faces.

Why Founder Depression After Selling Is More Common Than Anyone Admits

The phrase “it’s your baby” turns out not to be a metaphor at all.

Your brain is literally treating your company the same way it treats your child, and when you sell that company, your nervous system registers it as a genuine loss.

One referenced study of twenty-three entrepreneurs found that twenty-one of them experienced a form of depression after selling their businesses — something Jason describes as almost identical in character to postpartum depression.

He is careful to note that twenty-three people is not a large enough sample to draw sweeping conclusions.

But the pattern is consistent enough that he considers it the norm rather than the exception.

Founders who sell and then feel hollow, purposeless, or unexpectedly sad are not weak or ungrateful — they are human beings responding to a genuine neurological loss event.

Jason’s honest experience with this after SmartBear shaped how he approached WP Engine differently in almost every way.

What Jason Cohen Did Differently Building His Second Billion-Dollar Company

Lesson One: Build to Maximize Optionality

When WP Engine began to take off — and Jason describes the early growth numbers as beyond anything the standard startup benchmarks prepare you for — he made a conscious decision not to lock himself into a single exit strategy.

At SmartBear, he had operated with a plan to sell.

At WP Engine, he operated with a philosophy of staying open to everything.

Maybe they would go public.

Maybe they would sell to the right buyer at the right price on the right terms.

Maybe they would run it for twenty years because the cash flow made that the most rational choice.

The point was not to pick a destination before the road had been built.

The point was to build a company so genuinely excellent that every option would remain available when the time came to choose.

Jason’s definition of a great company is refreshingly human, and it goes beyond margins and growth rates.

It includes customers who love the product so much they stay and upgrade — not because they are locked in contractually, but because they actually want to be there.

It includes employees who do not leave, who recommend their friends to join, and who feel like the company is worth their long-term investment of energy and talent.

That is what he calls a great billion-dollar company builder foundation — and it is the foundation that keeps all doors open.

Lesson Two: Peel Yourself Out of the Company Before You Burn Out

One of the most counterintuitive moves Jason made at WP Engine was hiring a CEO in 2013 — years before he felt ready to step back.

He did it because he recognized something honest about himself: he hates managing people.

Not in a casual way, and not in a way he tried to hide.

He describes his dislike for people management with a quiet bluntness — “with a burning fire” — and he understood that if he stayed in a role that required something he deeply dislikes, burnout was not a possibility, it was a schedule.

So instead of white-knuckling his way through a job description that did not fit him, he gave pieces of it away.

First he stepped back from the CEO role.

Then from the CTO responsibilities.

Then from direct reports entirely.

Over the years, he sculpted his role at WP Engine into something that played to his actual strengths — the strategic, visionary, founder-level thinking that he is genuinely good at and that the company genuinely needed.

By the time Jason stepped away from WP Engine full-time — fifteen years into the journey — it did not feel like losing a child the way SmartBear had.

It felt like finishing a chapter.

He had already grieved and released the pieces of the company gradually, one role at a time.

And when the moment came to fully step away, what was waiting for him on the other side was time with his daughter, college visits framed as vacations, and a rest that felt earned rather than forced.

Lesson Three: Play the Box Game Differently When You Have Already Crossed the Freedom Line

When acquisition conversations started appearing around WP Engine, Jason ran the same box game he had played at SmartBear.

But this time, the boxes meant something different.

Because he had already crossed the freedom line after SmartBear, a guaranteed ten million dollars no longer moved the needle in a meaningful way.

He had already won that game.

So at WP Engine, when offers came in, he chose Box B every time — the higher-risk, higher-reward option — because the downside of zero no longer threatened the life he had already built.

He cannot share the specific details of those conversations publicly.

But the result is visible: WP Engine became a billion-dollar unicorn, eventually receiving a major growth investment from Silver Lake in 2018, valuing the company at over one billion dollars.

The box game did not change.

His position on the board did.

The Final Lesson: Build a Strategy Around Who You Are, Not Just What the Market Wants

Jason is currently working on a book that captures what he has learned across more than twenty-five years of building companies.

The final chapter, he says, is about the founder as a person — not the founder as a function.

His argument is that a strategy built entirely around market needs without accounting for the specific strengths and limitations of the person executing it is a strategy that will eventually break.

You cannot build a great billion-dollar company success story on a foundation that requires you to be someone you are not.

If a strategy depends on turning your weaknesses into strengths, it is not a good strategy for you — even if it would be brilliant for someone else.

The product has to make internal sense.

The market has to actually want it and be willing to pay for it.

The founder has to be someone whose natural abilities, personality, and working style are genuinely additive to the vision rather than constantly fighting against it.

All of those things have to mesh together not just adequately, but seamlessly — and that is exactly why strategy is hard and why so many companies that looked good on paper fell apart in execution.

Jason says you can start with the market — find a need and then ask whether you can build something to meet it.

Or you can start with yourself — identify the things you would genuinely crush, and then find the corner of the market that needs exactly that delivered at exactly that level of excellence.

Either direction can lead to a billion-dollar company outcome.

But only if the founder is honest enough with themselves to make the road match the person walking it.

We strongly recommend that you check out our guide on how to take advantage of AI in today’s passive income economy.