Red Pill, Blue Pill
Being a founder is a lonely journey
TLDR: The culture of starting companies is changing.
“It’s so lonely being a founder.”
This is one of those phrases.
Every time I share this with an audience of founders, there is a collective head nod.
It’s one of the few sentences in my repertoire where I am sure to get a predictable reaction.
The thing is, I’m not even sure if founders fully know why they’re nodding.
Sure it’s lonely starting a business for the obvious reason: at day one, it’s usually a company of one. And of course, there’s also self-imposed pressure to execute, uncertainty over what to do, very few people who truly believe in you, endless no’s from users, customers, and investors, and the list goes on.
But what people don’t always talk about is everything else in life that’s impacted by choosing the founder path. Leaving behind old friends. Losing predictability in your income and a quality of life you’ve become accustomed to and that others rely on you for. Prioritizing work to a level that your sanity is questioned. Walking away from a successful career, leaving behind a personal brand, and relinquishing the recognition and self-worth that comes with it.
It’s objectively crazy to give up these things in favor of venturing into the unknown.
Early on you don’t yet have the outcomes or proof that you’re going to succeed, or even that you know what you’re doing, so it’s difficult to fit into new professional circles or feel any sense of confidence. You can’t afford to pay yourself yet, so you’re living off your savings, or if you’ve raised a bit of money, off a dramatically reduced salary. Everything takes longer and is more expensive than you think, so your emotional fortitude is tested. These are just a few of the things that contribute to a feeling of loneliness and demand an incredibly high level of self-reliance.
I think it’s the depth of that topic that creates that visceral reaction I described.
Even if a founder tells you, “ya it’s lonely being a founder,” they themselves may have not even explored the deeper sense of isolation that comes with the territory.
That’s why resilience is such a profound trait in founders, and a hard one to underwrite.
When there’s a $500K investment on the line, most every founder will tell you that this is their life’s work, that they’re never going to give up, etc etc. And they may truly believe it at the time, but even with the best intentions, it’s impossible to know if you’ll be able to persist.
The determination you need to have to knowingly subject yourself to abject isolation, and the discipline you need to have to do it every single day for years on end is one of the more talked about, but still deeply underappreciated elements of being a founder.
This isn’t the experience for everyone, but certainly for the vast majority I’ve come across. It may not be isolation on every dimension, but there are almost always bouts of imposter syndrome, uncertainty, and the experience of a bruised ego from time to time.
However, there are also people who enjoy chewing on glass. They relish in the pain of doing hard things, knowing that they’re proving to themselves what they’re capable of, knowing they will never give up, and in turn, giving it everything they have to build a world that they know is possible.
They’ve stared down the option of Neo’s red and blue pill, and they know where the blue pill leads. They know they can stay inside the illusion, remain at their current job, do something less challenging for more money, or have a better work-life balance, but they choose the red pill. They choose to forge a new path, they choose to see what’s out there and if they can really change the world. They choose to find out what they’re truly capable of.
It’s admirable and it’s sad. It’s inspiring and it’s devastating.
We should instead create a world where founders are celebrated for taking risk, admired, encouraged, and recognized for doing something crazy, and there should be destinations all over the world where these ambitious people can work together to support one another to succeed.
It’s already here, it’s fairly unknown, but soon it will be ubiquitous.
See you Monday.
you kinda touched on it, but for me, the loneliest part was not sitting in the office at midnight putting together desks, or dealing with customers or lawyers or bankers or investors alone, but keeping the stress inside. I knew no one else, except other founders (who were busy with their own problems), could identify with it, and I couldn't let the employees or my family know how tenuous were the threads holding the company together. Dealing with that stress, almost on a daily basis for years, was the loneliest part of founder life for me.