The Entrepreneur’s Leap

“Entrepreneurship is jumping off the cliff and building a parachute in the way down.”

We like to celebrate this idea ☝️, but it’s not real.

• At best, it’s fantasy fiction.
• At worst, real life tragedy.

For every one person who “builds that parachute,” many more hit the ground at full speed and don’t get back up. The culture would have you believe that those who lay motionless on the pavement just didn’t have what it takes to succeed, and that their failure proves how exceptional those that “make it” truly are.

But look closer…

What we rarely talk about is how the person floating safely to the ground had a backup chute the whole time, or how their parents owned a parachute manufacturing plant. They took the leap, but they were never in danger.

Here’s the uncomfortable truth about success that flies in the face of the lies we’re told.

Parachutes vs Safety Nets

What so many of the “self-made” try to downplay, or in some cases seem completely oblivious to, is how different it is to take risks or struggle, when you don’t know for certain that you’ll be ok.

So, they gloss over some “small” details of the story.

• They started out with just “a small loan” or self-funded their first venture using the proceeds from a a teeny-tiny “apartheid emerald mine.”
• They dropped out of school to start their company, but miraculously succeeded anyway.
• They “got their foot in the door” — conveniently with one of their family friends

I don’t mean to suggest that these advantages mean these individuals didn’t work hard, have good ideas, or struggle on their path to fame, fortune, and wealth.

Sure, they (probably) worked hard. They likely had good months and bad ones. Sometimes they had to pivot, and yes, they were often, genuinely, pursuing their dreams.

Some make it. Some don’t.

Among this group, those that don’t make it might move in with their parents, pull from their trust fund, or resign themselves to getting a job. Luckily, they’ve got a few good interviews lined up (thanks, dad).

Those that do make it, often go on to be celebrated. They get invited on late night talk shows, become coveted podcast guests, or grace the stages of conferences to explain the source of their bravery and resilience.

• We hear about how these winners worked so hard, but less about how hard their teams worked.
• We hear about their long hours, but less about their partners who took care of the kids and the household.
• We hear about their brilliant ideas, but less about how being free from the concerns about making rent or putting food on the table allowed them space to think creatively.
• We hear about the risks they took, but less about how those risks carried significantly less danger to their survival.

They will gladly tell us a story about the parachute they built on the way down, but we rarely hear about the safety net that was right underneath them the whole time.

There are no islands

Adam Smith wrote The Wealth of Nations, which is widely considered the foundational text of Capitalism. In this book, he lays out much of the basis of modern day economics steeped in the principles of rugged self-interest. Remarkably, the role of the home, and specifically the (unpaid) contributions of women, are noticeably absent. All the while, his own needs were being tended to by his mother. Curious 🤔, isn’t it?

Jeff Bezos, Elon Musk, Mark Zuckerberg, and the like, are nearly all the product of gigantic safety nets. Few of them were in any real danger of falling into poverty. They all had food, water, shelter, and medical care. Yet, the narrative about each of these titans of industry paints them as an island of brilliance and resilience through adversity.

“Look at how smart they are. They did it all on their own.”

When they speak in public, they don’t interrupt the fawning over them to point out the many contributions of others that made it all possible. Yet, take away their advantages and their safety nets, and they are forgotten people of history. I wonder how many we’re leaving behind right now.

A First Hand Account

I’ve been working for myself for most of my adult life. I’ve failed a lot. Here and there, I’ve had some success.

I know I’m smart, and I’m good at some things, bad at others. While I have played my part in whatever success I’ve had, none of my success is entirely my own. Nearly all of it is because I’ve been lucky enough to have safety nets.

• I’ve been bailed out of financial trouble by my parents, a lot.
• The only reason my agency survived the early years, was due to my ex-wife carrying the family.
• The only reason my agency survived the later years was because of the great work my team members were doing that kept the agency afloat.
• The only reason any of my current initiatives have taken off and become successful, is because of the incredible support I’ve gotten from my wife, the inheritance I got from my mother, the pure excellence of my business partner, and the support I’ve gotten from my many friends and industry peers.

Even when I thought I was building a parachute on the way down, I was reminded that I had a safety net.

Years ago, I remember having coffee with one of my closest friends, Naomi. I was in a particularly rough patch where my agency was surviving but I was burning out. I confided in her that I was fearful of losing everything, burning out struggling to keep up, and struggling under the weight of my financial obligations. I was scared that if one thing went wrong, I wouldn’t be able to pay my rent and that I would become homeless. Without skipping a beat, she rewrote that narrative by reminding me that I would always have a place in her home, on her couch, for as long as I needed until I got myself back on my feet.

After that, I started playing the game differently. I felt safer, knowing that I always had a place to go.

More safety nets, less bullshit

This bullshit narrative about successful people doing it on their own, should not be allowed to continue unchallenged. We should press these self-made people to reveal their true stories, forcing them to wade into the uncomfortable place of acknowledging the support systems they benefited (and currently benefit) from. Because whether the safety net is familial or systemic, we need to be more honest about it.

In the same vein, we shouldn’t keep asking communities who have been systematically excluded from building generational wealth (safety nets), why there aren’t more successful (fill in the blank marginalized groups). The answer is clear: people keep setting their safety nets on fire.

We should be consistently reminding everyone how success is truly enabled…by making it safe.

If we all really understood this fact, maybe we’d change what we do, and who we celebrate. Maybe we’d stop engineering and perpetuating a society with winners and losers, where we force people who are falling from the sky to build a parachute on the way down. Maybe instead, we’d start putting up safety nets everywhere.

Perhaps it’s time we spend less time — metaphorically and literally — cleaning up bodies off the street, and more time celebrating the accomplishments and contributions of a healthy society, where everyone has the safety and freedom to be creative and take risks like the entrepreneurs we currently lionize.