5 Things I Learned By Watching 5 Startups Succeed and Fail in 5 Years

Kindness doesn't cost anything.

Mark Rothko, Untitled, 1958

For the last 5 years, I have been working primarily for tech and media startups. I’ve worked as a contractor, a part-time employee, and a full-time producer and strategist. I’ve worn all the hats one can fit on their head and then some. I’ve taken calls at 2 in the morning, while out sick, and I’ve traveled on my own dime at the demand of founders who made certain to remind me they sign the checks.

I’ve been along for the journey as one startup transitioned from a tiny outfit of funny, kind-hearted, ambitious Millennials to a large tech company run by Gen Xers and Boomers focused on cutting costs and labor. I also experienced working for startups unable to gain any significant traction after years despite very long days, meandering calls at odd hours, stretching of resources, constant shifting of priorities and product goals, and utilizing every resource and connection possible to grow.

In many ways, working for startups made sense for someone like me who is obsessed with failure. The reality is, 90% of startups fail. I knew that when I first started working for them and it scared me as someone without a safety net or inherited wealth. But, I also love creativity and innovation, so I accepted failure as part of the bargain since failure and rejection are part of the process of what a creative life involves.

Those who have been following this newsletter since its beginning in December 2021 know I was publishing every week until I finally hit a point of severe burnout at the start of this year, which I have been struggling to recover from. I felt like I had nothing left to give to myself or anyone else between the demands of a work schedule without boundaries and navigating some big losses in my personal life.

Then, this summer, I finally left a failing startup and another startup that had been acquired shortly after I joined (yes, I got some money, but only enough to keep me afloat after they outsourced all of us who helped build the product for cheaper labor abroad AND it should be said that money was only made by possible through the labor of union organizing). It’s taken the past 6 months of prioritizing more rest and sorting through everything I’ve experienced these 5 years to have any perspective on what I learned.

For the below, though I focus on two startups as case studies, the examples I share are a composite of experiences from working with five different startups in media and tech before taking a break from the industry.

Here are five things I’ve learned in five years about failure by watching startups fail and succeed (at least according to the goals of capitalism!):