Around 1998/1999 when I was a Senior in high school. The .com run-up. I had been doing all of this volunteering to score $$ for a big high school band trip over to Europe. I remember collecting newspapers and pop cans that somehow got turned into $$$. I had been slaving away for almost a year until one day my dad came home and said "I just paid off your band trip."
I was like what do you mean? Don't I have to keep collecting these newspapers and pop cans like my other band mates? He said nope, don't waste your time, I just paid off your trip for you.
I was enamored and he explained how he bought a semi-conductor stock (computer chip) I think it was like 3dFx or NVidia or something like that and it shot through the roof so he cashed out enough to pay the trip off ~$2000 at the time.
He had always had a rental property but I never really knew the mechanics of it all until I was in my 20s. Then, we went in together on a 6 plex when I was about 24. I didn't have a college degree, but I owned a 6 plex and always thought it was neat.
That 6 plex was A LOT of work. I turned to the internet to see if there was an easier way. Low and behold ER.org...some time around 2007 I found this forum. Someone was kind enough to point out that a 25/26 year old need not hold bond funds...that is when I learned about the different "phases" of FIRE...accumulation, and SWR etc.
I was sitting in a target date fund stricken with fear of doing something wrong when I married my wife. Once we were married her mom refused to continue to manage her money and was pushing her to do it on her own. She was not interested at all and when she let me login to poke around I was overcome with envy. She had 2x the amount of $$ saved and I had always made more $$ in the 6 years I knew her.
That was an eye opener that her mom self managing had done better than my target date fund. I hit the books, talked to an FA, some friends, family and basically went 'all in' on the DIY side of the house. For the past 10 year's we have been enjoying beating the market on a consistent basis and I am certain we have the foundation we need to propel us into ER.
My only regret, not investing sooner. Not being frugal sooner. My biggest assist
Marrying the love of my life.