Entrepreneurship Burns Your Ego

An output more precious than any success or failure...IF you let it happen

Welcome back to The Workaround. I’m Bob, your host 👋

You’re in good company with thousands of fellow entrepreneurs and innovators who read (or listen—see play button above) to my stories from a career in tech startups and corporate innovation.

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We must play with fire to grow up

“I’d love to start a business, but I think my ego is holding me back from giving up my current position.”

“I can’t share this idea until it’s perfect. My ego is getting in the way.”

“I’m afraid this will fail, and I’ll look like an idiot in front of my peers. I guess it’s my ego again.”

These quotes are a sample of what people said to me last month—just like the month before and the one before that.

Each individual I spoke with is a strong, proven mid-career leader with a robust network. They are tempted by an entrepreneurial path, and they could easily return to a traditional job if the leap doesn’t work out, but a voice in their heads blocks them.

You’ve noticed this Ego holding you back. They still try to stop me.

That voice—The Ego—is not us. We even call it by a separate name! Yet, we still allow it to hold us back from professional and personal growth.

I’m declaring “Ego” the word of the decade.

We live in a time when people are finally awakening to a truth religious prophets spoke about thousands of years ago: We must manage our minds to break bad habits, make effective decisions, and discover true happiness.

Books, coaches, and therapy can help. Watching others can also open our eyes. I’ve been inspired by learning people's number one regret on their deathbed is that they didn’t take enough risks. 

But first-hand experience is a much better teacher.

Choosing the career path of an entrepreneur has forced me to understand and overcome my Ego. It has been a wild ride of two steps forward and one-and-a-half steps back.

You might choose to start a company someday. Or you may have no choice—forced into a freelance or contract assignment in a corporate environment that increasingly drives us to fend for ourselves. Either way, I’d like to share what your Ego is in for.

Despite the risk of making entrepreneurship seem an even scarier proposition, I hope to share an under-reported payoff that is more valuable than any financial windfall that may result.

How the Ego Gets Installed

Here’s the instructional walk-through I wish we received as children:

“Welcome to Earth! Allow me to introduce you to your Human form!

You have a body. It allows you to run, jump, throw, play…and do some other really fun stuff that we’ll explain when you reach puberty.

You also have a mind, which works with the body to help you understand the world through the senses—smell, taste, feeling, hearing, and vision.

Unlike other creatures on Earth, your mind also comes with a helpful Artificial Intelligence that continually suggests proper ways to behave. This is called your Ego™.

The Ego is a voice you will “hear” speaking inside your mind. The Ego aims to ensure you survive on Earth for as long as possible. Lots of bad stuff can happen, so you’ll hear its voice a lot. Apologies in advance! 😀

Since Humans are a social species that must cooperate to survive, The Ego is especially tuned to how you fit among other Humans.

You’ll notice that the Ego grows with you over time—using past situations in your life to adapt its voice as you go. For example, if people laugh at you during a book report presentation in 3rd grade, your Ego will warn you about speaking in public the next time—for the rest of your life. Or if your parents didn’t give you much attention early in life, your Ego will seek more attention from other people—forever.

To ensure that you stay confident in your Human form, your personalized Ego will say lots of things to make sure you feel as good as or better than other Humans you meet. For example: “You deserve more things than they do,” “Other people should listen to what you have to say,” “That person just got lucky,” and “I should acquire more things to ensure others respect me.”

Unfortunately, your Ego exists only to help you survive. It is not programmed to make you “happy.” Apologies in advance!”😂

(Side note: Wouldn’t having a tutorial like this be great? Instead, we get parents and teachers telling us, “Life isn’t fair” and “Turn off the lights!”)

Ego Pulls Entrepreneurs

Now, if you just had a personal awakening by learning what that little voice in your head is, you have my permission to stop reading now and get thee to a Buddhist monastery.

Everyone else—whether you are an entrepreneur, tempted to become one, or just curious about why we are so crazy—should keep reading…

“Ego” is thrown around often when we look at famous company founders with private lives we are too familiar with. You'll find giant egos in Elon, Zuck, Jobs, and Gates.

Or go to the people you know who have succeeded or failed in starting companies. We’ve been just as full of ourselves—but with fewer rockets, yachts, and media platforms.

According to a study of successful startup founders by Edwin A. Locke and J. Robert Baum, “Among many common strengths found in entrepreneurs—independence, self-confidence, drive, tenacity, etc.—was ‘egoistic passion’ or a focus on proving themselves through their work.”

This sure nailed me. I have always considered starting a company the ultimate challenge and chance to prove myself. However, it also takes a big Ego to be confident enough to go for it. Like Broadway or NBA hopefuls, you must become convinced of your greatness to ignore the unbelievably poor odds of success.

But when you choose to “make a dent in the Universe,” the Universe smiles, pats your head, and says:

“You’re going to have to work for it, pal. I’m a complex, adaptive, emergent system that you can’t boil down to numbers on a spreadsheet and steps to follow from a Startup Accelerator. I’ve been around billions of years and have been doing just fine before you turned up. So if you want to dent me, I will make you suffer.”

Watch the Ego Burn

It’s funny how people on the outside say, “I’m sure a startup is hard work!”

When I hear “hard work,” I think about my first job as a kid, mowing neighbors’ lawns in Atlanta's 100-degree summers. The guys who had to climb over snowbanks to collect our trash yesterday do hard work.

Adjusting the position of slides on a pitch deck or sending emails to potential clients is not hard work in the traditional sense. However, entrepreneurship is very hard Ego work.

First, you leap and wave goodbye to all the cozy trappings that made you feel like a productive business person. Give up your title, salary, bonus, vacation days, and health insurance. Vendors will no longer wine and dine you. Airline upgrades are over.

Say hello to being repeatedly turned down by everyone: investors, clients, partners, hires, pitch contests, landlords, friends, and family.

You both wake up and go to sleep wondering why that client didn’t reply with the next step when they said they would—and whether you should nudge them again on Monday or wait until Wednesday.

You watch competitors raise more money and get more press than you. Their name is on a Times Square billboard, and you’ve got a 10x10 booth in the back corner of the conference hall—where no one is stopping by for your branded water bottles.

You exaggerate and promote any shred of good news. A big company says they want to have a second meeting! We got listed in the annual Top 50 Most-Promising Startups in Southwest Ohio! It’s all in hopes that clients and investors will pay attention—and that it helps convince your team to return to the office the following day.

You drag yourself to local startup founder pitch nights and happy hours. Everyone else there is “killing it.” You must nod, smile, say the same, and stay the whole time. After all, you heard a junior analyst from a VC firm might show up.

You spend precious dollars attending a “speed dating” event where clients promise to hear your pitch. One-third don’t show up. Most others aren’t buying. However, two are interested and promise to set up a follow-up meeting. They both eventually ghost you.

You beg everyone you’ve ever met to take a meeting or introduce you to a prospect. Almost none reply. People you’ve helped get jobs and whose jobs you’ve saved suddenly lose your contact info.

You’ll do mindless tasks for 80 hours a week and wonder if that’s enough time spent on the business. You question whether you’re trying hard enough or if you truly want it enough. Work 100 hours, and you’ll feel the same.

If you haven’t guessed, “You” includes “Me” here, as this has been my experience multiple times. This is just a mere sampling of the dirt you must crawl through to get something off the ground.

Just as nothing above is “hard work” in the sense of physical effort, the pain we experience as entrepreneurs is not physical. It’s much worse: it’s mental pain.

Our Egos stretch and strain under pressure. One minute, we’re king of the world; the next, we're the biggest loser. This cycle happens… oh, about every five minutes.

Multiply this by years, and eventually, something happens…

Success and Failure Both Burn

Your company fails.

You feel like a complete loser and long to bury your head under the covers for the next few months.

Alas, the founder cannot escape. We must make proper arrangements for our own funerals with all of the former clients, partners, employees, and investors. As much as investors say they are in the business of making bets that mostly fail, some can’t help but guilt you into searching for a way to claw back a half-penny on every dollar they invested.

I recall feeling shunned at startup events—“Dead Founder Walking!” No one gives you a hug or a pat on the back. Peers seem to edge away in fear of being infected by your failure. For those who did approach, I had a canned speech about all the “great lessons” I learned. I didn’t want to bring them down.

But, boy, a failure sure resets your mind. It’s finally over—what a relief! In the company’s death, we eventually experience a rebirth. We step out of the costume of that company and leave it in the past. We realize that we’re still alive and able to play again. But this time, we’re armed with so much more wisdom—mostly the wisdom how our Ego led us to our greatest mistakes:

I hired too many, too fast, and with too fancy resumes

I raised too much money, and I was afraid to push back on the people we raised it from

I believed our hype—and my own bullshit—rather than listening to the customer

My friend, Nadja, recently shared a German saying: “Once your reputation is ruined, you can live freely.” She wasn’t sure what the English equivalent would be. I think it’s: “What doesn’t kill you makes you stronger.” Either way, after failure, much less ego drives your life.

“There are many accounts of people who experienced that emerging new dimension of consciousness as a result of tragic loss at some point in their lives. Whatever they had identified with, whatever gave them their sense of self, had been taken away. Then suddenly and inexplicably, the anguish or intense fear they initially felt gave way to a sacred sense of Presence, a deep peace and serenity and complete freedom from fear.”—A New Earth, Eckhart Tolle

Or, through luck, pluck, or pivot, you beat the odds and succeed—usually by accepting an offer to be acquired by a much bigger, more established company in your industry.

Cue the world’s tiniest violin: This usually crushes your soul, too.

You’re stuck in an earn-out agreement for years—working for people who have never made a decision in their careers without calling McKinsey. You sit in on leadership team meetings with an incompetent CEO who doesn’t remember what your product is or why he bought it. That’s OK—he doesn’t know the profitability of his own core business, either. The line between dreams and reality gets fuzzy. How did I get here?

You continuously swing back and forth in searching for a path forward. One morning the Ego says you should learn how to suck it up and stick with this company. An hour later, you want to flip the table over in that soul-sucking meeting and prove that F.U. money is for saying F.U.

Each day your once-successful business dissolves into the common crappy denominator of its new ownership, and you’re strapped into a front-row seat for the slow death spiral.

Eventually, you get fired despite leading a business with the company's highest profit and revenue growth. It’s unsurprising—due to the ineptness of its leadership and your inability to play nice in their sandbox.

You say goodbye to the remaining members of the original team and watch them change the name on the door.

Getting a big number in your bank account solves many problems and opens many opportunities, but money can’t fix the inner demons that can haunt you.

Yesterday, I spoke with a brilliant private equity leader who has made millions of dollars. He said he feels unworthy of the money because it came from today's unfair winner-take-all finance industry. This man is making big, reckless bets, hoping he finally loses it all and can somehow save his soul. The only problem is his reckless bets keep winning even bigger.

Here’s another, and another. Or take Vinay Hiremath, cofounder/CTO of Loom, who shared:

“Life has been a haze this last year. After selling my company, I find myself in the totally un-relatable position of never having to work again. Everything feels like a side quest, but not in an inspiring way. I don’t have the same base desires driving me to make money or gain status. I have infinite freedom, yet I don’t know what to do with it, and, honestly, I’m not the most optimistic about life.”

Whether it ends with success or failure, the entrepreneur must start from zero all over again. The titles and trappings are gone, the buzz moves to something new, and we’re sitting in front of a laptop with a blank calendar again, wondering what to do with the rest of our lives. Our spouses and children wonder, too…

Growing Up is Burning it Up

Who am I?

What do I do now?

Every human has these questions, but they are usually lodged deep inside and covered by layers of protective Ego. The Ego is afraid of what we might find, so it would prefer that we get right back into the game of seeking external rewards and recognition.

However, post-end entrepreneurs can no longer hide or fake it. There be dragons in the lies we tell ourselves, and we must slay them to move forward.

I let myself get caught up in dreams instead of minding reality.

I did this to push back demons in my past.

I shouldn’t have listened to what all the “experts” told me.

I wanted to become someone else because I’m not happy being myself.

If you let it*, so much bullshit washes off your soul in the weeks and months it takes to process and integrate the intensely personal experience of entrepreneurship.

And here, dear reader, is where owning a business is so much different than working for anyone else: It’s all about you.

If you work for someone else, there is always an Egoic buffer. You can have fantastic success launching a new initiative at your company, but it’s their company. Or you can get a sudden Zoom invite from HR and become the victim of another corporate restructuring. Your Ego will console you with the knowledge that its leaders are fools.

But if it’s your company, you own it all. Now you have to own putting your pieces back together.

*…If You Let It

Some entrepreneurs avoid soul-searching and, win or lose, return to the game—only this time with an even bigger chip on their shoulder and a more powerful Ego running the operation.

Their motivation swells to achieve success so they can rub it in others’ faces—including the high school girlfriend who dumped them. Some think just one more zero in their bank accounts will allow them to finally relax. Others love the attention, power, and status of being at the top of the org chart they created. I can tell you, it can make you feel better, for longer, than any drug peddled on the street corner.

When I meet fellow founders, it’s pretty easy to see who is Pre-Ego vs. Post-Ego. It rhymes with the quote:

“Nearly all men can stand adversity, but if you want to test a man's character, give him power."—Abraham Lincoln

Those still stuck in Ego-land love to talk about their latest toys, compare valuations like measuring their manhood, and complain about how much their former spouses wrung out of their investment accounts. Those spouses used to be the only ones who could tell them “no.”

They may think they have more freedom than ever, but this is another lie the Ego tells you. How free did Musk, Zuck, and Bezos feel kissing the ring of our new President?

“The problem for them is that their status as the richest of the rich is, in ego terms, all they have left, which leaves them far more vulnerable than they would be if they were just run-of-the-mill billionaires.”—The Pathetic Billionaires’ Club, Paul Krugman.

Again, the Ego latches onto money and power in many corners…

I recall sitting at a dinner with startup leaders and investors at the annual Consumer Electronics Show a few years ago. Across from me, a repeat founder bragged about raising more money, saying, “This time, if there’s not a ‘billion’ in the exit, it’s not interesting to me.”

My friend works at a company that just achieved the dream of going public. To celebrate, its CEO organized a PR strategy with a primary talking point about how much money he made in the deal. This CEO now spends all-hands calls bragging about what he’s bought—and demanding to know why people don’t respect him more. Less than a year in, its stock is down 31%.

I know four creative agency founders who sold their agencies and turned their companies into a personal dating service.

Some quip that VCs look to back founders with Daddy Issues. There’s a lot of truth in this joke. Our childhood demons can feed an Ego that will move mountains. I’ve been here. And no amount of money or power can fill the hole some of us have inside.

But left unchallenged, the Ego Debt keeps piling up. A big bill will come due at some point in this life—or the next one. The Universe is a brutal loan shark.

What’s sad is they never get a chance to evolve their consciousness to higher levels of understanding and love. Money and power go to their heads, making their egos too big to fit through these doors of perception.

On the Other Side of Ego

Other post-exit founders I’ve met behave more like monks. Their presence rhymes with what I’ve seen in people who have survived a near-death health scare or have seen action in their military service.

Their eyes are wise, and their mannerisms are relaxed. Whether they win or lose the game, they have been humbled by the journey and are happy to be playing again. They exude gratitude and genuinely enjoy spending time with other people. These founders avoid comparing themselves to others and turn conversations toward curiosity.

Their suffering provided the impulse for awakening into consciousness.

I’m trying to learn from these peers. It’s a process of examining your mind and historic decision-making as a third party, like how a social scientist might study us or how a friend would console us.

We begin to see through and laugh at the bullshit our Ego shouts at us. It has to shout to get our attention now because it’s losing its grip. As its influence fades, we get closer to seeing ourselves and the world as it is, a perspective that helps us in countless future business and life decisions.

We become more comfortable with our new selves, caring less and less about how others see us. All news is good. Problems are expected and solvable, each a learning opportunity and a test to see if we’ve improved our reactions.

“The lifeforce I’m not using to project a false self is now available for much more fun and interesting purposes. It’s a whole different universe once all that petty self crap has been left behind.”—Jed McKenna, Spiritually Incorrect Enlightenment.

Because the Ego can no longer erect protective walls of separation, we grow curious, understanding, and appreciative of other people. Looking back, we see that none of our success was “self-made.” People become the purpose in our lives—both at work and home. We spend more time with others and are more present when with them.

Finally, we discover more of the creative Muse as a source of inspiration. She was always part of our entrepreneurial dreams, but free of the Ego, our work gains purity and purpose that was lacking before. We are more inventive, resourceful, and personal in what we build next.

Entrepreneurship is not the right therapy for everyone, but it has worked wonders for me. I’ve started more businesses than I can count. A few have done well, and many more have not. Either way, my ego is a little smaller each time.

“What if success is just about you, who you become, and how you change in the process? What if entrepreneurship is just an elaborate prop within which you can become who you are?”—The Entrepreneur’s Weekly Nietzsche

I’m still a work in progress, which is one of the reasons why I am continuing to choose this startup path. No matter what happens with my current projects and the next ones, I know I’ll be a better person on the other end. And I am grateful to the people who have and will join me along the way.

Now it’s your turn…

When you hear a friend say “ego,”—stop everything and help them see through it. If you catch yourself thinking it, step back and be your own friend. Realize you’ve taken a big step towards life's number one skill: Managing your mind.

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How we might work together…

• Fleet is our holding company for services businesses. We invest in leaders who are ready to start their own companies (we also do some M&A). If this might be you, Hit my Office Hours link.

• Revelin is our consulting practice that helps with revenue alignment, growth management, and other RevOps functions. CEO Jess Shuman is standing by to share a no-cost assessment of your business.

• Shipwright Studio is our software development agency led by Ross Lewellyn, a CTO who has led multiple successful startups. He loves helping turn your dreams into reality, and our clients trust us for software built to last.

• A2 Influence is our content development agency that helps some of the biggest brands and retailers create and distribute authentic content at scale, including social+influencer. The team just scored a partnership with Walmart. CEO Rob Reinfeld would love to share our approach.

• Hearty is our boutique recruiting service. Our difference is that you get C-level partners—including me!—to source and screen, resulting in killer talent in less time. When you’re ready, let’s chat.

• Feel free to schedule a chat during my Office Hours to discuss questions, feedback, networking, or any other topic. Seriously, any topic! You can also reach me on LinkedIn or by email.

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BONUS: Cool Content of the Week

A little something I found meaningful. You might agree…

How Meditation Deconstructs Your Mind

My understanding of my Ego and my journey to overcoming it started in 2019 when the stress around selling my company finally prompted me to try meditation. I described my early experiences in one of my first posts on Substack.

Nearly six years later, I continue to explore. Science and spirituality align in similar directions in this field, and their findings are increasingly accessible to non-monks like us. A recent example is the Vox article “How Meditation Deconstructs Your Mind.” The author uses straightforward language, scientific research, and personal experience to outline the levels and benefits of meditation. 

If you’ve begun a meditation journey, this might help convince you to stay on the path. If you’re new to the practice, this article could help your rational mind buy into the habit. One of the few regrets I have in life is not beginning a meditation practice many years earlier. But starting today will give you plenty of time to realize significant benefits.

As a special bonus, this is a link to a 30-day trial of the Waking Up app. It’s my favorite for starting the journey and further exploring self-understanding.

I hope to see you sitting!

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