What do you mean by succeed? To me, it's very specific. It is to live without debt or a mortgage in a safe place where I can afford medical insurance (which currently costs me $65,000/year). It also meant being able to spend as much time with them as my children required.

I guess you could say it took me from ages 21-38. If you count study as a child, 12-38.

However by the time I was 23 I was already super happy. I had a good job and could afford to take my girlfriend out a couple times a week. So the times from 23-38 were fulfilling and very enjoyable even though I didn't feel I "made it" until 38.

12: Started reading business books & biographies

16: Kicked out of high school

21: Dropped out of college & started to teach myself programming.

21: Fired from my first job as programmer

23-31: Worked as computer programmer, moonlighting journalist & got lots of free learning materials. Also spent all extra money on books.

25: Got angel funding for a business that sort of failed 3 years later

28-31: Programming jobs. Fired from another one.

34: PM job at Microsoft. Everyone sold their stock options due to dumb things Marc Andreesen said but I kept it all. Stock went up 1300% in the next 4 years. My friends who had been there much longer all seemed to listen to Marc.

38: Retired to due handicapped kid born. Stock was worth $1 million, had to sell it when I left. So $600K after taxes.

40: Bought a business, fixed it up, and it supported us beautifully for the next 20 years. Spent a lot but also saved a lot. HN calls it a lifestyle business. I made, say, minimum salary for an NFL football player. We bought our house for cash in a neighborhood where one of my favorite guitarists lived, but they couldn't make the house payment and moved out. Same for a local newscaster. I bought another house in the neighborhood for cash as an office.

60: Sold the business, now live off investments. Traded the houses for a farm in town.