All founders have a sickness

Your sickness drives you, so be sure to understand it.

It is January 2025, and I am catching up with one of my tentpole investors from Workstream.

He is one of the smartest, most successful and savvy people I know. He was a true believer in our vision, and despite our shutdown continues to be a champion of mine. He wants to hear what I am thinking of next.

The conversation naturally turns to the financial realities of being a founder, versus joining something.

"The NPV (net present value) of being a founder is great," he says.

"But not when you factor in probability!" I counter. "When you add-in the probability of success for a new venture, versus joining something, the NPV for founding is wildly negative."

With a smirk and biting wit, he replies: "This is the business you have chosen."

And he was right. This is the business that we founders have chosen — a choice that by the numbers does not make a lot of sense.

So what does it say about us? What compels us to so knowingly pursue entrepreneurship when it is so uncertain and illogical? What is the sickness lying in each of us that drives us forward?

We are all ill, myself included

Consider this: 72% of founders self-report experiencing mental health concerns. Breaking it down further:

• 49% report having one or more lifetime mental health conditions, 32% report having two or more, and 18% report three or more.

• 23% of founders are asymptomatic members of highly symptomatic families.

So the next time you attend a founders’ event, take a moment to reflect that half the people in the room have faced serious mental health challenges. And that a quarter of those sitting around you come from troubled family backgrounds.

Founders are certainly brilliant and capable, but we are not, on the whole, well-adjusted individuals.

So what about me? I have written before about my family’s long history of depression, bipolar disorder, and addiction—though I have been fortunate to avoid these struggles personally.

But I have still faced crises that pushed me to the edge. When serving as the Founder and CEO of Workstream, I experienced a time where I felt completely overwhelmed and incapable as a founder.

When reflecting on that time, I wrote: "If I’m being honest, much of what has driven my career has been a desire...to be a self-made, wealthy entrepreneur…I wanted to build a company, have power, succeed, and make money to fulfill the needs of my ego — to prove to myself and others that I was uniquely capable."

Today I see a founder who was suffering from a number of sicknesses:

A lust for power; a hunger for fame; a greed for wealth and riches; and a thirst for authority.

The need for power

So what are these sicknesses that I think plague all founders? Let's start with power:

Power is downward-looking — it is about how you interact with and influence those who work for you.

Power is about your ability to control others, to command what they do; at its most raw and aggressive form, power is about dominating others and controlling them to fulfill your whims.

Power wielded to its extreme is ethically fraught and dangerously intoxicating as a motivator; but having power is unfortunately often seen as zero sum, and therefore what so many young professionals aspire to.

For this reason, a great question I have always asked aspiring managers is: why do you want to manage?

The best answers, of course, would be that one loves teamwork and finds purpose in mentoring others. Or that one can make a greater impact through leadership. But let’s be honest—those are rarely our first answers. If you asked my 22-year-old self this question, I would have been nonplussed for a good reply.

The true answer is that we simply crave the ability to command, to be the one in charge. This fraught desire is deeply ingrained in our animalistic, mammalian brains.

The need for fame

Unlike power, the need for fame is outward-looking: it is about how others perceive you. Are you recognized by others on the street or online? Are you respected as an expert? Do people you admire also admire you?

It is worth reminding ourselves that aspiring for fame for itself is deeply flawed. When as founders we feel this urge, it is worth challenging ourselves as one ought to challenge a child who says they want to be famous. A healthy response might be: I love acting, so I want to be a great actor whose movies are loved; or I love basketball, so I want to win more NBA championships than LeBron James.

But those are rarely the answers we give. For most of us, it is most often tragically simpler. I want admiration because it makes me feel good.

The need for riches

Money, as my business school macroeconomics professor once put it, is a future claim on goods and services provided by others.

So the need for riches is thus inward looking — it is about the things we yearn for, and ability to make future claims on them.

This essay is not a diatribe against capitalism. I like money as much as anyone; I am fortunate and wealth has provided comfort for my family.

But while capital is a helpful and necessary element to living in our society, it also does nothing to guarantee happiness. Show me five happy rich people, and I will show you ten mentally ill and addicted richer people. In the context of providing happiness, money does relatively little beyond representing our mostly unfulfilled future desires.

Yet all founders pursue entrepreneurship, at least partially, as a means to acquire wealth. I certainly did and do. And again while this is only human and natural, it is important to recognize that the only monetary equation that really matters is whether your family income > family expenses.

And when we view money this way, the future promises of acquiring luxury goods like mansions, yachts and fast cars are far less important than your ability to afford groceries and a comfortable lifestyle for you and those you care for.

And while there are those who truly struggle, let's be brutally honest — the aspiring technology entrepreneurs among us have many options that are better than founder salaries to meet our most basic financial needs.

The need for authority

Unlike power, which is about control over others, authority is upward-looking. The need for authority is our refusal to be controlled by anyone else. This manifests in founders who just cannot have a boss or take orders. It is exemplified by a founder's desperate need to be king, and refusal to submit to others.

Many of the most beloved and eccentric founders embody this trait — could you imagine Steve Jobs, Elon Musk, or Mark Cuban working as a cog in someone else's machine?

The need for authority drives us, but is also deeply flawed. At one point my six year old son was fond of bragging that "my daddy has no boss." He was proud, and it was funny and cute, but I normally responded: "everyone has a boss."

Even those with immense authority, like Mark Zuckerberg, are not free from answering to others. Despite his absolute control over Meta through super voting rights, he still faces pressure from shareholders. He is subject to governmental pressure and the shifting political landscapes.

As ruler of a 3 billion user social-media kingdom, Zuckerberg has as much authority as any founder on the planet — yet if he must answer to others, then so do we all.

Antidotes

These are some of the many sicknesses that drive founders, myself included. And for all of us, Lord Acton’s words should serve as a warning: “Power tends to corrupt, and absolute power corrupts absolutely.”

There is no inherent virtue in acquiring power, fame, wealth, or authority. The real measure of success is not what you acquire, but how you wield it.

So what can we do to counterbalance these unhealthy drives? Here are a few antidotes that I have found helpful:

Self-Work: Take the time to clarify what truly matters. Understanding your purpose is crucial. Ambition is important, but it should be balanced with goals that are not purely dependent on luck or external validation.

Presence: Be content with the moment you are in. Not just the fleeting present, but your season of life and the stage of your startup journey. Learn to embrace where you are.

Learning: Adopt a relentless learning mindset. Entrepreneurship is about continuously growing into who you are becoming.

Some final thoughts

Before parting today, I will leave you with this:

If you are a founder, ask yourself: what does my journey reveal about me? And I remind you with love: be honest.

Be honest about the ways in which you are sick. For only then will you know what to do about it.