The point where you can get off the ramen diet and start buying all those toys you promised yourself you'd buy when you "made it"
Long answer - when your piece of art is complete. A great book, 'Finite and Infinite Games' lays out my feelings on this. Your first STEP in success is when you are really in the game. I've launched a few companies that nobody cared about. Got no traction. There was very little reason to keep revising the product/project because I wasn't in the game. Other times you hit on something that people care about, and that is making a difference. You work like mad to churn out new products and satisfy the demand. You are in the game. That is success level 1, and it goes from there.
I think the big problem with saying "how do you know when you've made it?", is that this isn't a sprint or a marathon. It's a life. You've never 'made it' in life, if you're done, then you're dead. When do you know when you have breathed enough? When you have eaten enough? If you stop working on your product/business, it will go stale and die.
You can 'get out', sell, hire others to take over the day to day tasks, but what do you do with yourself then? I think some of PG's comments regarding the 'artist' in programmers/innovators is just that. An artist doesn't stop painting once they have sold one painting. So your current project leads to the next, etc.
I would say to answer your question, that only you can decide when your current piece of art is done. If you're making great money, fantastic. If not, maybe you love this project so much that you'll continue with it anyway.
Basically, have an exit strategy, targets, goals, etc. But none of these are 'finishing lines', they are markers on the coarse. Like aid stations on a cicuitus marathon coarse. They let you know that you have reached a significant marker, but don't stop running, 'cause you are still in the race.
There are still things to do, problems to solve, art to build. The journey is the destination.
Edit: Issuing dividends to our investors would be great, but probably isn't a requirement.
Must... resist...
Free time + stuff to do + safety net + support family = ~100k per year. YMMV.
But thanks for the good news anyway. :)
As an aspiration, it's noble, but when pressured people nearly always find a reason to make more money instead of taking the time ;-)
Short answer: we live in a spacious dumpy place a 15 min walk away from Davis Sq (Boston area), have shitty health insurance, rarely use a car, keep the temperature low (read: cold) in the winter, don't go out to eat much and cook our own healthy food from the grocery/bakery. Despite all this, we still live like relative kings.
It's sort of cheating though because in terms of clothes & tech I came to Boston with everything I need so I spend literally no money on them now.
The secret is really roommates + no car + long walk to mass transit + cheap food. If you're willing to walk about 20 minutes to the nearest T stop, you can get quite a few places in the Boston area for ~$400/month. Eat vegetarian with a lot of rice & pasta dishes and you can probably squeak in under $10k/year, particularly if the university provides health insurance.
"Making it", as far as I am concerned is having a steady stream of people coming through my door through personal recommendation with really interesting problems - enough in fact that I can turn the less interesting ones away to other people.
I get to make money, I get to help people (I know it sounds sappy, but I love it) and I get to think about interesting problems.
It doesn't get much better than that for me, it really doesn't.
No. I haven't quite "made it" yet, I only started out as an independent a few months ago, but I've had enough of a taste of it to make me a very happy bunny.
By this logic, as a founder you may realize you've created something successful and fun but it's time to bring in different people to do things that you are no longer economically optimal to do.
Jeff Bezos is a great example of someone who clearly has a fun time every single day and whose creativity is still vital to Amazon's performance.
Unless I really really want to.
1. Realizing you haven't been checking price tags on food or household items for a while now.
2. Making money faster than you can find things worth spending it on.
3. Being well-off without having to work full-time.
4. Being well-off through actively-managed passive income.
5. Being able to sail around the world and come back richer (through passive income, not sea trade nor piracy nor fortune hunting ;).
6. Being able to do what you want, where you want, when you want, without the permission or approval of anybody.
I'd be fairly happy at number four already, because I could just decide to go hang out in various countries for x months at a time without having to worry about money.
Financially: $1,000,000/Year in passive income.
Socially: The Espada brand being universally recognizable and associated with my name.
Automotivally: Lotus Elise, Bentley, the biggest legal monster truck I can find.
Personally: Having no fear
Some might think this is superficial, though I know precisely what I want and don't apologize for it.
after that, i agree with others that it is nice be able to ignore money -- to me that again speaks to peace of mind.