The whole experience was the hardest thing I've ever done.
It was also one of the most fulfilling professional experiences of my life.
I intentionally stepped off the corporate ladder to pursue this dream. But because of my prior commitments/obligations, I wasn't able to drop everything and go all in. That was a hinderance. It made things harder. It put a strain on my family. But it was doable. And even though we didn't achieve our ultimate goal, these complications were not the reason for failure.
I became an independent consultant that gave me an income with some flexibility to allow me to asynchronously lead our startup. I called the time outside of my consulting work "the nightshift". We raised a seed round that allowed my younger and less encumbered co-founders to work as FTEs. We took in more funds that added another six FTEs and an offshore team. Over the 10 years we existed, I never took a salary. When the chips were down and I needed to be 100% dedicated, I emptied my retirement account.
This arrangement was far from ideal, nor do I fully recommend it, but it gave us a shot. We built, tested, and learned our way to a product that served several million (non-paying) customers. We made plenty of mistakes. But we learned from them. We learned to be so frugal, so resilient. So incredibly nimble and innovative. I yearn for that kind of creative power again. It has prepared me to take on anything in life. I've never been to war or faced death with my comrades on a daily basis, but in business terms, I imagine startup life is as close as you can get. The experience has made me a better husband, father, friend, and colleague.
I've since returned to corporate life (for now). There I am invincible. None of it scares me. Corporate politics, bureaucracy, and general bullshit pale by comparison. My startup experience has become my superpower. Because I know I can help raise our game, knowing how to bring out the best in our people and to keep perspective on what is truly "hard" and how to get things done with less and under far less ideal circumstances.
So I say go for it. But go in with your eyes open. The odds are long no matter what. Might as well take your shot. At the very least you'll learn a lot. And someone with your talent, as long as you continue to hustle, rarely go hungry in this world. And if you succeed, well then, you might get a book deal in the process.