25 Individuals Lift The Curtain On Their Rich Friends’ Careers

Published 4 weeks ago

In the expansive realm of Reddit, discussions often lead to fascinating insights and unexpected revelations. Recently, a Reddit user sparked an intriguing conversation by posing a simple yet compelling question: “What does the wealthiest person you know do for work?”

The responses that flooded in were as diverse as the Reddit community itself, unveiling a kaleidoscope of occupations that contribute to financial success. From nepotism-tinged narratives to unexpected enterprises like selling Runescape gold, the anecdotes shed light on the manifold paths to affluence.

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Image source: bbbbbthatsfivebees, Mika Baumeister / unsplash (not the actual photo)

A family friend retired after being a COBOL programmer for 30 years. About 2 years after his retirement, a company came to him and said “Name your salary” and he requested around $1.5 million/year. He was hired on the spot and still works there.


Image source: Apprehensive-Crow-96, Caleb Ruiter / unsplash (not the actual photo)

Truck driver. Starting his own trucking company.


Image source: tic-a-boo, Géry PARENT / unsplash (not the actual photo)

Found a diamond mine in the NWT.


Image source: AnAussieBloke, Giorgio Trovato / unsplash (not the actual photo)

I work for a lady who inherited ~100 mil.

She just buys real estate and sets them up as rentals, I just do general maintenance on them (I also rent from her)

She lives like she’s on a pension and pays me in magic beans half the time.

A true embodiment of money does not buy happiness.

I have tried many times to push her to go enjoy being so wealthy, but she lives with the mindset that because she does not have a partner, why bother buying a villa in Tuscany or jump on a flight to Bora Bora just to enjoy the beach and a nice seafood banquet.

So she tends to sit on her couch and drink wine with the tv on in the background.

I got a shock one day when she emptied a pillowslip of Krugerands onto her kitchen bench, as it turns out she has somewhere in the range of 2.5mil in Krugers, Maples and Sovereigns just sitting in pillowslips in her walk-in wardrobe.


Image source: Ligmartian, PhotoMIX Company / unsplash (not the actual photo)

My Dad, he does a bunch of random things. He retired from the Navy and uses his retirement pay to invest in real estate. He became a photographer after retiring and did really well for himself. Now he has contracts with a load of schools and sells off temporary subcontracts to budding photographers for schools he doesn’t have the time to work with. He flips cars in his spare time, but right now his day job is high school business teacher.


Image source: CoolJeweledMoon, Life Of Pix / pexels (not the actual photo)

The first is a self-made multimillionaire who’s owned his own concrete finishing business since he was about 19.

The second is a self-made millionaire who became a very successful accountant who was continually promoted at work, & he consistently bought stock & real estate from a young age.

The last person is a millionaire who will inherit family money, & she’s a high-end real estate agent.


Image source: OT-35, Yiorgos Ntrahas / unsplash (not the actual photo)

It’s a guy I work with. He started with one Jimmy John’s franchise and turned it into 10 franchises. Ran them for 10 years then sold them all and dumped the money into the stock market and real estate. He did this all while working as an airline pilot, currently still working at the airline. This dude owns and flies his own private jet on top of all that.


Image source: ThaiLassInTheSouth, Sigmund / unsplash (not the actual photo)

My buddy owns a cybersecurity and general tech firm here in town. (Small town, hardly any competition.) He’s a badass marketer so he has contracts with the state’s NFL team and the largest Porsche dealer in the Southeast.

He also owns a salvage yard, oddly enough.

He balls and he’s so fkn cool. His employees all get a track day once a year and box seats to the biggest games. He’s also generous with in-town initiatives, like toy drives and tech donations to public schools in the ghetto and the town’s “sped” school.

Additionally, he invites the community out to free meals he hosts in his office space (which is gorgeous). He hires pizza and hotdog carts and lets people walk up and get a plate! For his buddies, he turns the office-space (which has a friggin’ basketball court in it) into movie-viewing // MMA fightnight watchspots. There’s a theatre in there. He charges NOTHING … has stuff catered in and has a full bar … wants nothing in return but for everyone to have a good time and get home safe.

He’s a fantastic father to his teenaged daughter, too. The way she adores him, dotes on him, picks lint off his suit, fixes his hair. He’s been so gentle with her all her life and she’s growing up to be just as gentle as cool as her Dad.

(Damn. I just wrote a love letter lol. But naw: I just admire someone who GENUINELY cares about people and doesn’t let money go to his head. He’s fkn awesome.)


Image source: SCP_radiantpoison, JESHOOTS.COM / unsplash (not the actual photo)

She’s a doctor, an immunologist and a damn good one! She’s been involved with the WHO, CDC, EMA and other three letter agencies. Has published papers and does community outreach with a foundation for immunocompromised kids or kids with deadly allergies.

She doesn’t really need to work, her family is super rich, between a rancher, an oil industry consultant and a local politician as brothers she’s comfortably off but she’s passionate about this and actually nuked her personal life and family for it.


Image source: HybridTheory23, Norio Nakayama / Wikipedia (not the actual photo)

Friend got lucky with TSLA. Invested early and retired at 35 a multi millionaire.

Now owns a bar in San Diego to stay busy.


Image source: Ok_Lifeguard_6508, Ruthson Zimmerman / unsplash (not the actual photo)

CFO of a large public company. He works 80 hour weeks. F**k that.


Image source: ShipJust, Jezael Melgoza / unsplash (not the actual photo)

Inherited small factory from his father. Developed it to huge nationwide company. Still goes to work there everyday despite being worth hundreds of millions.


Image source: LadyCordeliaStuart, Amber Kipp / unsplash (not the actual photo)

Pig farmer. I kid you not. He’s my father’s old friend. I visited him once when my father and I were passing through the state. He lives in a modest classic farmhouse with his wife, both in their seventies. I mentioned I was starting a school in West Africa as we were catching up. A few weeks later I got a text asking how much it would cost. I told him 40k, thinking it was really nice of him if he wanted to send a few dollars.

I got a check for 40k. I thought it would take me years to raise that. I’m typing this from Sierra Leone because he also paid for the house I thought would take years to raise funds for.


Image source: thecasualchemist, Matthew Manuel / unsplash (not the actual photo)

One of the first 100 employees of Microsoft.

I was friends with a guy from a rich family; they lived on a lake with a private dock, multi-million dollar home. Microsoft guy was their neighbor.

They used to have these game nights where we’d all get together, have cocktails and play pretty silly games – cards against humanity, pictionary, that kind of thing. I was really, really good at these games, and it impressed Microsoft guy. He wrote me a *glowing* letter of recommendation praising my intelligence because of this.

It helped me, an immigrant, land an engineering job at a huge aerospace company.

I’ve worked on multiple satellites that are currently in orbit, and I’ve touched stuff that’s on the surface of Mars now – hell, I was able to buy a house before i turned 30 – all because this man thought i was clever and witty, and wanted to help me out.

Needless to say, the imposter syndrome I feel every day is unbelievable.


They owned plots of land all over a county.

They lease them to cell phone companies for more than my monthly income x2 per plot.

I’m usually careful what I say around them because I once said I wanted a new fence but we were going to wait until prices came down… I came home from work and someone was putting a new fence up.

Image source: MadeMeStopLurking


Image source: Former_Situation2826, Jeriden Villegas / unsplash (not the photo)

They own a large construction company, based in rural NZ. Employ heaps of people, are very generous to their home town, humble too


Image source: IBringTheHeat1, Gavin / unsplash (not the actual photo)

Wealthiest I know is myself. Make a little over 120k being a ups driver.


Image source: Ptatofrenchfry, Etienne Martin / unsplash (not the actual photo)

I know the CBO of an international bank. He works a minimum 12 hours a day, 6 days a week. On Sundays he “only” works 6-8 hours. In his downtime he’s on standby for any issues that may crop up, to the point where he once responded to a client within 15 minutes. At 3.45 am.

He’s working when I’m sleeping. He’s working when I’m at lunch. He’s working while flying abroad to visit family. He’s working during car rides in between meetings with said family. He’s working while working (co-attending 2 separate meetings while replying to clients).

I have no idea how he works so hard and yet remains so calm. He’s basically a Swiss Army C-suite, since he does everything from sales to tactical planning to IT support to shareholder discussions. When I talk to him about it, his response is “I’m only 51, I’m still young.”

He also has a high-needs child, so his work hours are 6.30 am to 6.30 pm so that he can fetch his child from the daycare, since his office is closer to the daycare than his wife’s.

That man is borderline superhuman.


Image source: omniumoptimus, cottonbro studio / unsplash (not the actual photo)

The wealthiest person I know (and hang out with regularly) built a company (IT services) and then sold it for several hundred million dollars.

He now runs a company that does the same kind of IT services in a different field. (He figured out a winning business formula and is just repeating it in a different market.)


I used to work with a hydraulics technician. He did property development as hobby. He started by flipping houses and grew from there. He mentioned that he couldn’t resist buying 200,000 shares of the company we worked for because it was such a good price at $3 per share. That company eventually went private at $60 per share.
Honestly, one of the nicest and most humble guys I’ve ever worked with, and I hope that every cent made him happy.

Image source: LionNo3221


Image source: TakeMe_To_Eisengard, Markus Winkler / unsplash (not the actual photo)

Own their own conveyor belt business. Makes almost 2 mil a year after it’s all said and done.


Buying every beautiful, historical house in town and turning them into small, tiny rooms to rent out, ruining my towns real estate market. F**k him.

Image source: Upstairs_Cost_3975


Image source: I_Have_A_Name37654, Robert Boston / unsplash (not the actual photo)

My neighbors son works for the space force and makes six figures.


Image source: Ms-Proteus, Louis Reed / unsplash (not the actual photo)

Laboratory medical director. She earns $500,000 annually.


Image source: somethingcanadian

my friend sold runescape gold. He made a fortune.

Saumya Ratan

Saumya is an explorer of all things beautiful, quirky, and heartwarming. With her knack for art, design, photography, fun trivia, and internet humor, she takes you on a journey through the lighter side of pop culture.

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