I will try to answer multiple questions here because I am being throttled:
> How do you handle support with just 3 people? I imagine at that scale you either have a lot of customers, or small number of customers with very specific needs.
We are highly automated. Very very few queries get through and they are contracted out.
> what is the skillset of 3 people? 1 product, 1 sale/market, 1 developer or something else? how complex is the product in terms of technology?
2 developers (I am 1 of them) and 1 person for everything else.
> Are you in a large market with competitors but still plenty of room, or have you more or less cornered a smaller one?
It's a large market with 20+ competitors. Because our operational costs are so low and we are highly automated we could take over big chunk of business from our competitors. Essentially the dynamic is like Altavista vs Google.
Our competitors sometimes do some really dark patterns. I am realizing that almost all companies do that (Google incognito tracking, Facebook charging kids in games etc). Somehow I can't get myself to do that. So I am thinking of moving to Saas so that I can deal with mature customers and ideally provide them value.
> What are your skillsets? How did you get there?
I am a programmer as my core skill. But I have also played product, marketing, sales, hiring through my career. To get good a these, I worked in my jobs as if I was the owner. That helped get me experience faster.
If people want to do a startup, best advice for them would be join a startup with good team at an early stage. Bonus points if that startup is in a space you like. Learn, make good friends and then then do your own startup.
I really recommend Naval's "How to get rich" podcast. It's as if he is talking about my life. He decided to move to more investing, but I still like building stuff myself.
> What distinguished the successful attempts from the unsuccessful ones?
> How did you know when it was time to move on?
If I don't know how to keep growing the business, it's a dead-end and time to move on.