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What have been the best and worst investments of your adult life?
DerekJohnson
Administrator, Swaye's Wigwam Posts: 66,644 
in Tug Tavern
Guessing this will stimulate some interesting conversation…
Comments
Best investment: buying luxury watches before Covid and then selling them for 3X what I paid for them to morons.
Worst investment: The time and energy I put into UW football for 30 years. Ok Ok no jokes I owned a sizeable (for me) investment in Bear Sterns when they went tits up. That was a giant fuckup.
Best investment - dinner and drinks at O’Dohertys begat Mrs Throbber v2.0. Nothing else compares.
Worst investment. - none. There are no bad investments. Just educational events.
Zen
I bought a jump rope a few years ago
Fitted ski boots by a top-tier place in Bozeman. Cost a shitload but so worth it.
Life-changing, even.
No horrible investments for me because I play the long-game and primarily safe. I don't treat my retirement like the lotto or casino.
Good investments? The best, by far, was buying our house in 2018 and watching the appreciation pour in. Best part is that there will be no new neighborhoods almost anywhere in Western WA that offer what ours does in terms of lot size due to all the infill zoning changes, etc that have been rolled out the past couple of years. Want a house with a big yard that isn't on 5+ acres? Won't be finding that with much new construction.
Chines AK 225.00. Closing in on 6k.
How much?
Horrible investments? Beanie babies...
Good investment michael Jordan autographed Jersey....
Or my mark Mcguire mother's cookies signed advertisement display
Right around $1000 for the Lange boots and custom fitting. Did it in late 2023.
My feet never hurt anymore even on a full day of backpacking a lunch away from the crowds and Jerry lifts.
That's not bad
Worst investment: Been in 20 weddings over my life. Best man in 10 of them. I blew enough on bachelor parties to put a kid through two years of college at UGA or GA Tech. I keep in touch with only about 6 of the grooms.
Best investment: Real estate. Bought my mother a house for 84K some years ago. Sold it last year for almost 700K. Not the best return but a great savings plan. We have owned 8 homes and made money on all of them.
Second Best: Invested in a company called Machismo Mouse a 100 years ago. $1500 turned into $15,000 in two days. Pulled my money out and promptly got a call a year later from the SEC investigating me and several others of insider trading. I hadn't and it went nowhere.
Second worst: Loaned an old girlfriend $2,200 bucks for stripper tits. Motor boated those things for about 6 months before she started banging her ski instructor at Snoqualmie Summit and never paid me back. I think she is on husband #4 so I dodged a bullet there. I am sure those tits have been a landing spot for many a guy.
My annuity from 2009.
I might buy some rural land over the summer. Some day a developer will pay me five fold for it.
I had a girlfriend from 2006-2008 who "borrowed" thousands. I can't even remember how much, but probably way over 10k in today's money. Some of this were things like car payments and other bills which I covered. Lazy, dumb, couldn't hold a job...it was great to dump that bitch but I think the remnants affected me for two or three years.
My mom’s aunt died in the late 90s. Had a five unit rental in Auburn. My dad tried to talk my sister and me into buying it from the estate for 165k. I was only in my 20s and didn’t really understand how I could afford that, never realizing he would have financed it for us until years later. Told him nah, not interested.
City of Auburn bought the property to build some parking for the train station like 15 years later for 1.1 million dollars
So I got that going for me. Which is nice.
I'd say property as well. I just sold 2 of them and purchased another in SD. Buying into this down market will pay off some day as well.
I remember that name Machismo Mouse. Remind me what they were all about.
Best investment: hijacking the UW EE lab to mine a whole bunch of bitcoins
Worst investment: losing the hard drive with my ill-gotten gains
Worst miss was my grandpa’s house in Red Lodge, Montana in 2002 after he died. My brother and I could have bought it for $40,000/each. Didn’t buy because he lived in Seattle and I was in Portland.
My mom and uncle sold it for about an $80,000 profit 15 years ago.
Today, after minimal work, it’s a $600,000 home near downtown of a niche little town with a decent ski mountain, and Yellowstone Park is a few hours away over the Beartooth Pass. The owners AirBnB it for $200-300/night all year long.
Haven’t made any bad investments ever as I always bought at the right time in both Portland and Bend. Stock investment for me is minimal risk as I was fortunate enough to get some real estate that I sold in Bend and put into some land here in Montana.
Worst- "loaning" money to acquaintances for business upgrades. That money won't ever come back
Best- Giving my mother-in-law the down payment for her condo after she got out of an abusive relationship with her second husband. Built in baby-sitter three miles from the house, Sunday dinner for nearly 15 years.
When she passed, she gifted it to our daughter who will graduate with no debt and will have a paid off 2/2 condo as she begins her career.
Small world. Machismo Mouse was founded by Tiger Warren who ended up piloting a float plane that crashed into the Columbia River killing himself and his three sons. I picked up his ex-wife as a client prior to that event.