The Entrepreneurial Power of Embarrassment

As entrepreneurs we’re always talking about Failure. Failure as the opposite of Success, which is money and fame and a 16-core Mac Pro, and maybe a helicopter. Failure is the opposite. Running out of money, no one using your app, selling your office furniture on Craigslist.

There’s some debate about whether you should be ashamed of Failure — or celebrate it. Well, while I’m not here to talk about that, I’m sure you can find many wonderful Medium posts on that subject, but I will discuss a very related topic: embarrassment.

(When I say embarrassment, I don’t mean how you felt at age 12 when your Gran dragged you to her Red Hat Society meeting and you ended up covered in wet, red granny kisses from strangers.)

No, I’m talking about the feeling you get in your gut when you take a calculated risk and know you might seem silly but that the payout will be worthwhile. It’s a specific kind of embarrassment, that I’ll call entrepreneurial embarrassment.

The first time that I realized the power of calculated embarrassment was in China. I’d left for a year, thinking that I’d just pick up the language naturally. Instead, what I got really good at was conveying a message without any language at all, like a mime but with sound effects.

When I found myself wildly gesticulating with one arm in the air whilst making a loud trumpeting noise in order to find the elephant exhibit at the zoo it hit me: sometimes a little embarrassment can really take you places.

With startups, it’s embarrassment that you have to quash when you push submit on that new app, or when you cross your fingers and/or pray that your site does well on HackerNews. Quashing the alarm that goes hand-in-hand with anticipated embarrassment is a skill.

Reid Hoffman, of LinkedIn, has famously said:

“If you’re not embarrassed by the first version of your product, you’ve launched too late.”

Undoubtedly true.

(Although it’s clear from the state of LinkedIn that every version of their app launched right on time to be embarrassing, so…)

If you’re not embarrassed by your product at first you’re overly perfecting it. It’s taking too long to come out.

And embarrassment doesn’t just benefit product development — it’s also KEY for marketing purposes. If Richard Branson can cross dress and serve drinks on a competitor’s airline, then you can certainly go give your business card to a speaker at a conference. You can make a YouTube series on using your product. You can dress in a chicken suit and slingshot stressballs with your company’s name on them into a crowd.

Like Nike says:

“Weigh the risk against the reward and calculate your odds of success and remind yourself that embarrassment is temporary.”



Why? Little known fact here: embarrassment won’t kill you. It’s not a fatal condition. The next time you’re forcing yourself to do something, just think, would Richard Branson do this? Undoubtedly. Hell, he’d do it in a skirt and your Gran’s red lipstick.

Your startup needs you to quash that embarrassment. No shame, all gain. Be bold, ye entrepreneur, for a Blue Ocean is thine. Be *that guy,* the one who will do anything to promote their startup. Shout your URL from the rooftop. Wear your T-shirt to weddings. Beg developers on bended knee, if you have to, to join the team.

Embrace entrepreneurial embarrassment: have no shame.

And go download Fittr. ;)