Thanks for sharing this — I think bootstrapped companies get way too little exposure so people think raising money is the way to go. For 99% of companies it’s not AND the reason has nothing to do with anything the entrepreneur can change. It’s about the business model.
I say this as someone who A) has started, run, and lived off bootstrapped companies since 1979 and B)been an angel investor and mentored more than a few startups.
To your questions of how to grow this thing. I can’t make any recommendations without understanding more details about your unit economics, your business model, your goals and some other stuff. Be happy to chat in a more private way if you want — john (at) CEOBootCamp (dot) com.
But I can say this. The best money comes from customers. People have grown billion dollar companies that way. Almost any other source of funds comes with strings. Those strings are different for each funding style but all can turn into nooses more easily than you think.
With very few exceptions, you can’t go wrong selling customers something they like to pay for, at a profit. Those exceptions have to do with the context (business model and sometimes competitive space) but don’t apply to most situations.
You ask for a family-centric path. I know of none better than being in control of a lifestyle business at the proper scale. The critical phrase in that sentence is not “lifestyle business” which is often used in a demeaning way. But it’s actually a way that a lot of wealth (financial and otherwise) has been generated. The critical phrase is “at the proper scale”. The wrong scale (sometimes too big, sometimes too small) has tripped up many a family-centric company, in my experience.