To be honest, I would never do something that requires a single employee ever again. I sold my first company because soon enough, all you get to do is manage politics and not the thing you signed up for — Sounds infantile but at some point you have to stay true to yourself no matter the benefits. If you're more of a team-player, there are obviously better options today (remote, etc.) — The only thing I would recommend is not getting too romantic with a co-founder, having clear responsibilities from day one and don't try to make friends along the way — in the end it's all about building success.
It is now a year later and I'm still wondering the same thing as I was back then (as in, I haven't changed up my work setup at all / haven't hired people). I do rely on contractors here and there, but it's rare.
I quite enjoy the peace and quiet that comes with no employees. These days I just do a bit of focused work each day, prioritise spending time with my family, and enjoy sticking to my daily training regiment (the latter has been a key aspect of my life ever since I started my entrepreneurial journey).
Every time I consider hiring people for the sake of more growth, I find myself asking if it'll be worth it, and whether I'll regret it.
I doubt I'd be able to enjoy the work/life balance I currently have if I were responsible for managing people at scale.
Perhaps I'm being narrow-minded here, but it's good to receive affirmation from someone whose done it all before.
Sounds good to me — Feeding one or a thousand employees doesn't make a lot of difference because you can lose only so many hours of sleep over it each night.
FWIW I know a handful of people of all ranges of success in the tech startup world, managing tens to hundreds or thousands.
Some of them are very driven by the stress of management, and seek it out. Their mentality is that a work situation isn't worthwhile if it isn't pushing you to your limit.
But they're the minority. I feel like you either know that you're this kind of person or you're not.
The rest feel burdened by their situation, and would happily trade for yours 300 days out of the year. They not-irregularly make comments, in private to friends, along the lines of "sometimes I wonder if I'm living life wrong? maybe I should be in the park with my kids instead of on the nth investor call or one-on-one with a direct report".
Like most questions, I think you can answer this with a mixture of experiments and introspection. You say you've manage contractors, for example.
Do you ever feel like you wish you had more responsibility for their lives? The urge to give mentorship is real, do you wish you could do that in a professional setting?
You can probably find ways to scratch those itches that are outside your company, too, for what it's worth.
You're in a good position where you get to "choose your own adventure", so you should experiment with it! Document your feelings, find somebody to talk it through with, iterate towards a happier spot. There's always ways to test your curiosities without sacrificing everything, if you get clever with it. :)
Thank you for posting this and previous year's Ask HN. Knowing that it's possible to run some successful && semi-passive && one-person && work/life-balancing SaaS businesses for such a long time is inspiring.
I've been through a number of startups and there are jobs that I really really dislike down to my core.
My 2nd startup I did the CEO role and i hated every day of it -- I really respect those who can spend day after day in investor meetings, sales calls, marketing catch-ups; that person isn't me.
My 3rd startup I decided to stick to technology - with a heavy dose of management - and partner with someone who could do the above.
Startups are already barely tolerable as it is, you can at least help yourself a little by being able to focus on the areas that bring a little joy into your life.
