The upside of bootstrapping

Over the weekend I attended a non-alcoholic bar pop up in London with a few friends. The couple running the pop up was both holding down full times job while also running a full scale pop up cocktail bar that had sold out every night for a month in London.

Both in their mid thirties, they were visibly exhausted but so excited when we walked in and throughout the night I could see how passionate they were about building this bar. As the evening came to a close, one of the founders stopped by our table to explain how her husband had become allergic to alcohol after getting long covid, prompting them to start up this no-alcohol concept.

She was transparent. Starting this pop up was really difficult. They’d given up all their annual leave just to run this concept for a month, bootstrapping it almost entirely themselves. They weren’t used to hospitality work and their entire bodies ached from pulling long night shifts. Despite this, the concept was clearly a hit, and one thing that stood out to me was this quote she said to us:

“We’re doing it our way or we’re not doing it at all. There’s no in between.”

I liked that quote because I agree with the idea behind it, even if it is a tad bit idealistic. Here are two people putting out a great product into the world with real soul, a product with a real genuine founding story, started by two people who could probably make a lot more money doing just about anything else. I suddenly wanted to consume their product more, not just because I enjoyed the non-alcohol cocktails, but also because I wanted to support them.

As I’m also discovering, the upside of bootstrapping something people really want is that when you have the proof: ie sales, orders, bookings, or revenue, you enter into a special dialogue between the business and the customer. As a bootstrapped business, this relationship is almost sacrosanct. No investors are pushing you to grow faster. Its just your team, listening to your customers feedback and actually giving them what they want, when they want it. When it works, its one of the most delightful things to see and gives me hope that capitalism can still solve a lot of our problems.

As I’ve been writing this newsletter, I continue to find the “bootstrapping” term hard for me personally to describe the way I want to build. Other writers have started to chime in about one-round wonders, but personally my new favorite term is “Silicon valley small businesses”.

Terminology aside, perhaps underlying all of this talk is not just bootstrapping literally but the bootstrapping mentality: doing more with less and being totally unapologetic about the product you’re building.

As we left that night, I thought about the challenges this couple was going to face, but somehow it didn’t seem so bad looking at the smiles on their faces with loads of happy customers in that dimly room in East London. Starting a company is really hard but it seems a heck of a lot easier to bring something into the world your damn proud of.