What You Can Learn From Successful Failure

 “Shame clouds our memories, rewrites history.”

So says Lauren Kay, Y-Combinator graduate and founder of failed startup Dating Ring. Reading Lauren’s essay about her failure inspired me to come clean about my shame.

I started an institutional money management firm with literally zero assets under management. 

I was one of the few women of color to own her own firm in the mid ’90s. Over the following 25 years I grew Daruma to $2.5 Billion under management. It was a huge success.

I closed it 2019, walking away with nothing.

I did not sell it or monetize it, a cardinal sin for capitalists. I paid off a $600,000 lease liability and walked away with nothing. I could have sold, but only if I agreed to indentured servitude. My grandparents did that in Hawai‘i’s sugar plantations. Not me.

I felt like a total loser until I read Lauren’s essay.

Her courage in sharing the shame she felt for having failed (even though 90% of Y-combinator graduates fail) inspired me. She was successful in all the ways, until she failed. Her failure shouldn’t have been a source of shame. Neither is mine.

It doesn’t matter if you beat the odds and accomplish more than most people.  When it doesn’t end well, you are ashamed.

I succeeded until I failed. I built an institutional money management firm from nothing and put up awesome performance numbers until I didn’t.

Lauren’s essay made me realize that I should celebrate everything, because my failure, like hers, wasn’t possible without all of our success.

Auguste Rodin, Public domain, via Wikimedia Commons