What is Rock Bottom, Fear, Risk & Financial Ruin? (From the Founder of Bonobos)


The wisdom of pants? Isn’t that a book or something?

Somebody posted one of my new favorite stories of success, risk, and world openness this week on my Facebook feed.  The story was written by Andy Dunn, one of the co-founders of the uber-hip e-retailer, Bonobos on the collaborative platform, Medium. It is aptly titled The Risk Not Taken  (Mini-love plug: Their pants fit better than the one’s you wear to work).

In the beginning of the story, Andy quite transparently breaks down his financial situation during the infancy of Bonobos:

For the first three years of Bonobos, I lived with $3,000 in the bank, a $3,000 apartment, and $150,000 of debt. During that time – 2007 – 2010 – I was only a month away from being out of cash. I was paying myself, initially, $70,000. This is plenty of money in most places, but in NYC it can fly you pretty close to the trees on just rent and alcohol.” 

Hmmm, living a month away from personal financial ruin and spending most his money on rent and alcohol? Sounds a lot like….everyone who works and lives in a city during their twenties.

His story then works its way anachronistically to his travels all over the world where he began to discover the thrill and enlightenment that can be reached when making decisions that define our life and career paths.

Founded in the reality of imperfection, we can make strides to take the risky route. Understanding how other people have done it, can help us to feel more comfortable with these daunting decisions. This is one of those articles that supercharges my own motivation. Here are some of my favorite quotes, (supplemented with my commentary) from Andy’s article.

“Very little is obvious in the research on human decision-making and happiness. Very few things are proven. One thing that is proven is this: the only regrets octogenarians have are for the risks not taken.” 

-If you’re not going to take it from me, take it from the 80 year olds

“It turns out there is risk in taking the steady job. The risk is generally not financial. It is spiritual.” 

-Yes, I will get hippie on you from time to time

..After he informed his friend that he wasn’t going to take a steady job, and rather, he’d help jumpstart Bonobos among a heap of financial debt, his friend said, 

“You’ll never starve, and you’ll always have a place to sleep. Worst comes to worst, you can always stay on our couch.”

…”It was a passing comment, but it stayed with me. There is protection for you in this world if you make it known that you need it. I stayed on that couch many times.”


     The worst that can happen: The Rock gently guides you back to Earth

And my personal favorite, mostly because it’s fairly contrarian relative to how many of us live our lives.

“Don’t ask your parents what to do. Instead inform them of your plans, and ask them what risks they took at your age.”

That is powerful.  Seek not for advice on your decisions, rather, understand the perspectives of elders through their  past experiences. Indirectly, through this storytelling, it can help to shape your direction, while not completely informing it. Listen to your gut, don’t steal someone else’s.

Read, this unconventional tale here: The Risk Not Taken.

…And more great advice from a founder: Reddit Founder Explains How Not Knowing Anything Can Be Your Greatest Advantage (VIDEO) 

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