Last man standing

My first job was an internship at a New York City-based startup. The company had funding from A-list investors, a cool logo, lots of swag, and, I felt, smart people working there. Underneath the veil of office-wide happy hours, free merch, and a collegial “we all eat lunch together” culture, however was a general sense of nervousness. Would we hit our metrics this quarter? Would we run out of cash by Q2 next year? Should we be working harder because we heard at Uber they pulled all-nighters for the first few years? 

If, as a company we were a bag of nerves, individually, things were even more up in the air. Many of us weren’t sure how to do our jobs and certainly had not been taught in school what needed to be done. A year later, when I joined an internship at a VC firm, the feeling was similar: What companies should I be looking at? Should I still be looking at SaaS companies? What about consumer? Or marketplaces? 

As time went on in my VC job, I noticed I questioned myself less and less and it was around the four year mark that I distinctly remember a new feeling arising: confidence. I had a point of view about markets, could openly disagree with senior partners, and felt like I might just be getting the hang of things. 

I’ve been a founder for a little over 2 years now and I’ve gone on a similar journey, first imposter syndrome, then the initial surge of confidence, then the “this-is-going-to-be-harder than-I-thought” trough.

Each month, quarter, and year that has gone by, however, I’ve become a little more sure about what I am doing. I’ve built conviction in why I am following certain practices while forgoing others. I’ve clarified who I am building my product for, so much so that I recently invited a paying customer to leave. I couldn’t imagine having that kind of clarity about my business a year ago!

We’re constantly bombarded with this idea that things should grow faster and be solved quickly. However, most of the big problems our world faces today are complex and will take decades to solve. If you are tackling such problems, hunker down and prepare to build for the long run. Time is likely on your side and the winner is often just the last man standing. 

Thanks to Caroline for the inspiration for this post.