My story
From VC to bootstrapping, building outside the hype, and introducing our new collective
My first job out of school was with Bessemer Venture Partners. I joined as an analyst intern in New York in 2016. Oddly enough, I was the only intern that summer, but that sort of reflects what venture was like back then.
I had one objective as an analyst: source deals. Doing so involved talking to 15-20 companies each week, followed by an adrenaline-inducing weekly sessions pitching two precious logos to a live audience of partners.
Back then, capital efficiency was king. We literally had a set of criteria each company had to meet: bootstrapped, profitable, cash flow positive, $5M+ in ARR, etc.
For several years, the VC industry felt sustainable, a healthy mix of competitive firms and founders building enduring businesses. By 2020, however, it started to change. I had just moved to London to help open an office, and as more capital came into the industry, the hype started to follow.
By 2022, things went from bad to worse. A guy named John from a firm called Tiger Global was DMing founders with checks on WhatsApp before even meeting them. Capital efficiency went out the window. It was time to leave.
After quitting, I initially experimented with raising some money from an angel, only to realize after 6 months that 1) I had no idea what I was doing and 2) I did not want to get on the venture track right away. I returned the money and decided to go another way.
I knew I wanted to build a company on my own terms and eventually ended up starting an IRL social club. Our group initially met on Wednesday evenings, the name stuck, and Wednesdays was born.
Unlike the companies I used to work with in venture, Wednesdays is not in a “hype” category like Crypto or AI, and it’s small by VC standards. For a while, I felt ashamed of this. Lately, however, I’ve been feeling proud.
Proud of myself for building something I love. Proud of myself for not giving in to the latest hype, and proud of myself for writing about the journey here.
As a former VC and now solo bootstrapper, I believe that we entrepreneurs can help each other, which is why I'm thrilled to share the first launch of Seeking Solutions Collective (SSC), a private community dedicated to entrepreneurs building on their own terms.
Whether you're exploring building something new or are already on your way, our first product is an online space to discuss and help each other, share inspiration, meet other like-minded founders, organize meetups and masterminds, and more.