1. This is probably a strange answer, but joining the military.
I was able to mature and save up a small nest egg, get access to the Post 9/11 GI bill, and some combat wounds were 100% worth it for the disability check and healthcare lol
That let me go to to college and a great law school with no debt, and led me to where I am today.
Plus, I wouldn’t trade the experiences for anything. Home run.
2. Starting my own business. I went from being stuck grinding day after day to make someone else rich, to taking the lion’s share of my efforts and being in control of my own schedule. I work 15-20 hours a week and earn 3x more than I ever did as a W2.
3. Finding the right partner … and only being married one time. Spouse and I had a similar worldview and thoughts about money and spending habits. When I got laid off years ago, to no surprise she was supportive, hid her worries about it at the time and even helped me make the list of all the things that we were going to cut back on for the time being.
Starting my own company after the above layoff happened during a sector downturn when no one was hiring. It had always been on my list, but I wasn’t aggressive enough to take that step on my own. Had to be pushed into it apparently. It took about 12 months for me to get to the stage where I was actually happy that the layoff had happened. Since then the net profits in the business, which all flow through to us, have been top end 32x old salary, and are more typically 14-20x.
4. Getting into real estate and working for myself and out of accounting slaving away for partners to line their pockets working 60+ hours a week. Buying a house with 3% down in 2018 leasing the extra rooms to people to offer all of the mortgage. Doing that four times in a row, reinvesting the savings into stocks and crypto. Saving/investing > 50% of take home pay since i started working out of college. NW is 2.3m or so at the age of 32
5. Getting into medical school. Didn’t have a single interview the first time I applied. Got in the second go around. Glad I didn’t give up.
6. The fun ones were 1) when my husband and I went from $150-200k each to $500k+ each, at the same time, for a few years in a row. 2) A $550K check was a recent boost.
From a % of assets though, my biggest one is the most boring of all home runs. We started saving and investing early and often in our careers. Second to that is buying a very modest home for our income which allowed us to save and invest a huge portion of our earnings for retirement.
7. Insane luck. My third startup is now in the S&P 500. About 20 things in a row had to go right, any one of which would have torpedoed things had it gone wrong. So just luck that I got hired, and luck that we succeeded. Luck should not be underrated.
8. Mine was a bunch of slogging year after year. I had 32 years with the same company (through a couple of acquisitions) and pay, bonuses and RSU’s were on an upward path the entire time. I went from making $40k to $300k (well over $500k most years with bonus and stock) and saved a lot; maxed out 401k (plus a generous company plan that contributed 15% of salary each year); never sold stocks in down markets, never panicked. Actually added to stock holdings in 2010-11, and 2020. Sure there were a couple of “liquidity events” but they weren’t that significant to overall net worth. Oh yeah I also bought a chunk of Apple 20 years ago and still have it.
I retired last year. NW around $8M, not counting equity in home (another $1.5M).
9. The obvious answer is liquidity events from one of FAANG. First was $80k, second was $3M, third was north of $10. In hindsight, I really shouldn’t have taken that first $80k one 😀
But the real moments were reading Millionaire Next Door and A Random Walk Down Wall Street in high school. Although the FIRE community didn’t really exist back then, I was incredibly lucky to be exposed to the basic ideas such that I was explicitly working towards FI even in college. Having had so many years in advance to process it all made the actual transition relatively smooth.
10. Selling a house in Austin at the height of the bubble.
11. First was starting to buying apartment buildings for myself rather than others. Started really adding a lot of NW with that.
2nd was having one of my businesses explode during Covid (3-4x net income of pre COVID).
3rd was having liquidity finally that let me buy very opportunistic deals. (Doubling my principal in 2 years)
It’s funny because it all snowballs. The first step is the hardest. Getting to $1m felt impossible. Getting to $2-5m felt hard but easier. Getting to $10m wasn’t that bad. My plan now is to get to $20-30m within 5 years and it’s funny bc it doesn’t seem that difficult anymore.
12. Joined a boutique investment fund as a software enginer. We put 40% of our NW into it when allowed to invest, and it had massive returns. We made it to just past 8 figures, retiring next year.
13. Bought a bunch of bitcoin when it was $500, bought a bunch of Tesla stock when it was cheap (basis of $12), bought and held Nvidia when it was at around $7.30 (pre-splits) back in 2003.
I bought Nvidia because I’m a gamer and thought it had potential, no idea it’d eventually blow up like it did.
14. Sorry, but my home run was staying put and slogging it out. There were several times when opportunities came up to change (especially tempting during the Dot Com boom), the home run decision for me was not changing, just slogging.
Theodore Lee is the editor of Caveman Circus. He strives for self-improvement in all areas of his life, except his candy consumption, where he remains a champion gummy worm enthusiast. When not writing about mindfulness or living in integrity, you can find him hiding giant bags of sour patch kids under the bed.