Sure, you could always be saving more money. But in the end, we’re not going to remember the cash we hid away, but the things we bought, and the experiences they gave us. Spending can be a positive, life-affirming thing, as long as you’re being smart about it.

But here’s the big question: What’s worth paying for? Twenty years from now, what are you going to remember as the best buck you ever spent? Was it the money you spent on a new car? The big house? The vacation in the Bahamas? Or something you never would have guessed would be so important?

We invited a panel of big spenders—investors, entrepreneurs, actors, and even an astronaut—to tell us about their favourite, most memorable purchase. Was it something with a price tag in the millions? Or less than you’d find between couch cushions? Some of their answers might surprise you.

Steve Woz” Wozniak
Co-founder of Apple Computers with Steve Jobs and Ronald Wayne

AMOUNT SPENT: $52 

“A ticket to the largest hedge maze at Longleat Castle in the U.K. You run this maze for what seems like an hour and eventually you luck out and solve it. I ran the maze time after time and still do so until this day. I have made it to the elevated finish point and tried to conduct friends with walkie talkies as to how they could solve it, only to see those friends sometimes give up and take the easy exit.

“Eventually, my son Jesse and his friend Kenny made a list of directions—like, left-left-right-middle-right-left—and it almost worked. A few years ago, I paused for a long time at the elevated finish point and scanned and scanned the large maze and determined the shortest solution and the easiest set of two rules to get there. I could have used Google Earth or a satellite image to find the best path but I did not do it that way.”

Charlie Sheen
Actor, Master of “Winning”

AMOUNT SPENT: $250,000 (+ – R 3.4 million)

“Babe Ruth’s 1927 world series championship ring. I’ve owned a lot of baseball memorabilia, but it remains the most significant artefact of an era. It’s kept in a vault and I visit it every February 6th, the Babe’s birthday.”

Mark Spitznagel
Founder of Universa Investments, a multi-billion dollar hedge fund company

AMOUNT SPENT: $750,000 ( +- R10.2 million)

“It was 2009, near the depths of the last financial crisis, and I found myself wandering over an old run-down farm in northern Michigan. It had been badly neglected over the years, a shadow of its once glorious past, with old farm buildings on the verge of collapse filled with unidentifiable rusty machines, countless pitchforks, and one mummified cat. But the farm’s rolling pastures, woodlands, and antique apple orchard were incredible; you could smell Lake Michigan in the breeze, and even see it from a ridge.

“Best of all, the farm was for sale, and around these parts farmers just don’t part with their family farms, run down or not. It was a once in a lifetime.”

Leroy Chiao
PhD, former NASA astronaut

AMOUNT SPENT: $1,600 

“When I was already a pilot, but before I was selected as an astronaut, I was looking to acquire the ultimate ‘pilot’ wristwatch. I was in Davos, Switzerland for a week on business. I passed a small watch shop every morning, and would take a few minutes to look at the beautiful Rolex GMT Master in the window.

“On the last day of my trip, I walked into the shop, asked to see the Rolex, and bought it from the pretty blonde saleswoman. Since then, it has been a good luck charm of sorts. I was selected into the Astronaut Corps just a month afterwards, and I wore the timepiece during every one of my spaceflights. It is still the watch I wear daily, 24 years later.

“I plan to pass it on to my kids. But, I wonder if they will appreciate it? After all, by then, we’ll be way beyond the iWatch. It will probably be a thought-controlled direct brain implant, which continuously puts the time tag in the lower right field of view of the virtual heads-up display.”

Sir Richard Branson
Founder of Virgin Group, a British venture capital conglomerate

AMOUNT SPENT: $295,000

“The best money I ever spent was on my family home, Necker Island, which we purchased from a British lord for a remarkable knocked down price. Having originally been told that it would cost £3 million, something well out of our price range at the time, my wife Joan and I didn’t take no for an answer.

“We held on for three months, during which time I found out that the owner needed a quick sale to fund the construction of a building in Scotland. Knowing the owner required £200,000 for the build we upped the starting offer of £150,000 to £175,00, before a phone call arrived informing us that it was ours for £180,000. Deal.”

Gurbaksh Chahal
Multimillionaire entrepreneur and CEO of RadiumOne. (Oprah Winfrey called him “the wealthiest entrepreneur on the planet Earth.”)

AMOUNT SPENT: $1 million

“My parents came to this country with $25 in their pocket. So we grew up pretty much poverty stricken, living in the projects in low-income housing. You learn to appreciate every dollar.

“Well, three months after I turned 18, I sold my first company for $40 million. When the reality sank in that I was actually a millionaire, I immediately bought a house for my parents, paid off the mortgage, and got them a Lexus. It was the most satisfying thing I ever purchased.

“If you ever get a chance to spoil your parents or give back to them in some way, you really should. It’s the meaning of life.”

Jim Cramer

Host of CNBC’s Mad Money and author of the new book Get Rich Carefully

AMOUNT SPENT: $238

“In May of 1985, I finally finished paying off all of my loans; my college and law school debts, as well as personal loans, credit card debt, and collection agency bills. I wanted to do something frivolous to celebrate. So I went to the decidedly non-ascetic 42 Street Photo and bought myself a boom box.

“My apartment was 30 blocks away and I couldn’t find a cab, and after a couple of blocks I decided, to heck with, I was walking with it on my shoulder. Why not? I was, at last, emancipated, and there was no gaudier, no bombastic and, yes, no sweeter way to celebrate than having a boom box swinging in the breeze, saying, free of debt at last, for all of New York to see.”