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What 10 extremely successful people were doing when they were 25

Who wants to be a billionaire?

EVERYONE’S PATH TO success is different.

For some, it can be straight forward enough but others encounter more twists, turns, and bumps along the way.

Billionaire Mark Cuban, for example, faced hardship when he first started. When Cuban got to Dallas, he “was struggling — sleeping on the floor with six guys in a three-bedroom apartment,” he wrote in ”How To Win At The Sport Of Business.” On the other hand, Starbucks CEO Howard Schultz was a salesman dreaming of good coffee.

To prove that no two paths to success are the same, we’ve highlighted what Cuban, Schultz, and 8 other successful people were doing at age 25…

1. Oprah Winfrey was co-hosting a local talk show

YouTube / OWN TV YouTube / OWN TV / OWN TV

According to the Huffington Post, Winfrey was fired from the 6 p.m. news slot at Baltimore’s WJZ-TV in 1977 at age 23.

In 1978, a 24-year-old Winfrey was recruited to co-host WJZ’s local talk show ”People Are Talking.” While there, she also hosted the local version of “Dialing for Dollars.”

Winfrey remained in Baltimore throughout her mid- and late-20s, until moving to Chicago in 1983 to host “A.M. Chicago” for WLS-TV.

2. Richard Branson had already started the Virgin Records record label

Courtesy of Richard Branson via LinkedIn Courtesy of Richard Branson via LinkedIn

At age 20, Branson opened his first record shop, then a studio at 22, and launched the label at 23. By 30, his company was international.

Those early years were tough, he told Entrepreneur: “I remember them vividly. It’s far more difficult being a small-business owner starting a business than it is for me with thousands of people working for us and 400 companies. Building a business from scratch is 24 hours, 7 days a week, divorces. It’s difficult to hold your family life together; it’s bloody hard work and only one word really matters — and that’s surviving.”

3. Tina Fey was a childcare registrar at the YMCA before joining famed improv troupe Second City

YouTube YouTube

After graduating from the University of Virginia, Fey moved to Chicago and hung around acting workshops and even worked as the childcare registrar at a YMCA before improv troupe Second City invited her to join.

Fey told The New Yorker that she joined Second City because she “knew it was where a lot of SNL people started,” and in 1997 she sent scripts to “Saturday Night Live” producer Lorne Michaels, who then hired her as a writer.

4. Mark Cuban was a bartender in Dallas

Daveynin / Flickr Daveynin / Flickr / Flickr

At age 25, Cuban had graduated from Indiana University and had moved to Dallas. He started out as a bartender and then a salesperson for a PC software retailer. He got fired because he wanted to go close a deal rather than open a store in the morning. That helped inspire him to open his first business, MicroSolutions.

“When I got to Dallas, I was struggling — sleeping on the floor with six guys in a three-bedroom apartment,” Cuban writes in his book ”How to Win at the Sport of Business.” “I used to drive around, look at the big houses, and imagine what it would be like to live there and use that as motivation.”

5. J.K. Rowling came up with the idea for the Harry Potter series on a train

Wikimedia Commons Wikimedia Commons

Rowling was 25 years old when she came up with the idea for Harry Potter during a delayed four-hour train ride in 1990.

She started writing the first book that evening, but it took her years to actually finish it. While working as a secretary for the London office of Amnesty International, Rowling was fired for daydreaming too much about Harry Potter, and her severance check would help her focus on writing for the next few years.

During these years, she got married, had a daughter, got divorced, and was diagnosed with clinical depression before finally finishing the book in 1995. It was published in 1997.

6. Jay Z was already in the rap scene but was relatively anonymous

Wikimedia Commons Wikimedia Commons

Born Shawn Carter, Jay Z grew up in a housing project in Brooklyn, New York, and became known as “Jay Z” at the age of 20. For the next few years he appeared alongside various other rappers, but “remained relatively anonymous” until he founded the record label Roc-A-Fella Records at the age of 27 with two other friends. The same year, Jay Z released his first album, “Reasonable Doubt.”

7. Marissa Mayer had just started her job as Google’s 20th employee

Hubpages Hubpages

At 24, Mayer became employee No. 20 at Google and the company’s first female engineer. She remained with the company for 13 years before moving on to her current role as CEO of Yahoo.

Google didn’t have the sorts of lavish campuses it does now, Mayer said in an interview with VMakers, “During my interviews, which were in April of 1999, Google was a seven-person company. I arrived and I was interviewed at a ping pong table which was also the company’s conference table, and it was right when they were pitching for venture capitalist money, so actually after my interview Larry and Sergey left and took the entire office with them.”

Since everyone in the office interviewed you in those days, Mayer had to come back the next day for another round.

8. Mark Zuckerberg’s Facebook was cash positive for the first time and hit 300 million users

BusinessInsider BusinessInsider

Zuckerberg had been hard at work on Facebook for five years by the time he hit age 25. In that year — 2009 — the company turned cash positive for the first time and hit 300 million users. He was excited at the time, but said it was just the start, writing on Facebook that “the way we think about this is that we’re just getting started on our goal of connecting everyone.”

The next year, he was named “Person of the Year” by Time magazine.

9. Hillary Clinton had just graduated from Yale Law School

The William J. Clinton Presidential Library The William J. Clinton Presidential Library

At age 23, Hilary Rodham Clinton began dating fellow Yale Law student Bill Clinton. She ended up staying at school an extra year to be with her boyfriend, and received a JD degree in 1973, just before turning 25. Clinton proposed marriage after graduation, but she declined.

That same year, she began working at the Yale Child Study Center. Her first scholarly article, “Children Under the Law,” was published in the Harvard Educational Review in late 1973, when she was 25.

After moving to Arkansas in 1975, Hilary finally agreed to marry Bill.

She’d go on to become the First Lady of Arkansas, The First Lady of the US, a US Senator, and US Secretary of State.

10. Starbucks CEO Howard Schultz was a salesman

YouTube YouTube

After graduating from Northern Michigan University, Schultz worked as a salesman for Xerox. His success there led a Swedish company named Hammerplast that made coffeemakers to recruit him at age 26.

While working for that company, he encountered the first Starbucks outlets in Seattle, and went on to join the company at age 29.

On his job in Xerox, Schultz writes in “Pour Your Heart Into It”: “I learned more there than in college about the worlds of work and business. They trained me in sales, marketing, and presentation skills, and I walked out with a healthy sense of self-esteem. Xerox was a blue-chip pedigree company, and I got a lot of respect when I told others who my employer was … But I can’t say I ever developed a passion for word processors.”

And there you have it folks. There’s hope for us all.

– Jacquelyn Smith

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    Mute Mr. Biggins
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    Mar 22nd 2025, 7:02 AM

    Another great gone, RIP George

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    Mute tony hilton
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    Mar 22nd 2025, 7:47 AM

    @Lance Taylor: must give that a watch today.

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    Mute brian o'leary
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    Mar 22nd 2025, 7:10 AM

    Rip George, I might grill a few sausages for breakfast, in your honor.

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    Mute Buster Lawless
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    Mar 22nd 2025, 1:02 PM

    @brian o’leary: sausage egg bacon cheese and mushrooms all place in a baguette then pressed in the Georgie! Yes sireeee

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    Mute John K
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    Mar 22nd 2025, 7:25 AM

    Down goes Frazier, down goes Frazier, down goes Frazier!! Get chills when I think how easily Foreman beat prime Joe Frazier, who himself had beaten Ali and was thought unbeatable! Absolute legend of the sport!

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    Mute John Bathe
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    Mar 22nd 2025, 7:16 AM

    Sad news, great boxer and a great guy by all accounts.

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    Mute Paddy Ryan
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    Mar 22nd 2025, 7:16 AM

    Tough as nails, rest in peace sir.

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    Mute Me Me
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    Mar 22nd 2025, 7:53 AM

    Watch ‘When We Were Kings’. The days when the title ‘Heavyweight Champion of the World’ actually meant something.

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    Mute paul hayes
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    Mar 22nd 2025, 11:17 AM

    @Me Me: “Champions forever” is a little older but a hell of a watch too. Probably on YouTube

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    Mute Dermot Blaine
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    Mar 22nd 2025, 12:29 PM

    @Me Me: that’s one of the greatest sport documentaries ever

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    Mute Brian Dunne
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    Mar 22nd 2025, 7:40 AM

    Any man that beats Joe Frazier twice is some man! To come back from Zaire the way he did was inspirational, and to win a world title 17 years after that was the stuff of fairytale. RIP George, one of the very best.

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    Mute Fergus O'Donnell
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    Mar 22nd 2025, 7:05 AM

    A great guy. RIP.

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    Mute did you every wonder
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    Mar 22nd 2025, 7:26 AM

    A true legend. Both in and out of the ring. RIP

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    Mute brian o'leary
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    Mar 22nd 2025, 7:16 AM

    I remember watching the Moorer fight, he was 20 years younger than George and had an unbeaten record, but still ended up on the deck.

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    Mute Phillip Smyth
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    Mar 22nd 2025, 8:41 AM

    Good old George great boxer and a gentleman many a toastie I had on your machine, lovely man
    R. I. P. Champ.

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    Mute common sense
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    Mar 22nd 2025, 8:29 AM

    I watched a film about his life on Netflix recently. RIP

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    Mute Colm Doyle
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    Mar 22nd 2025, 7:43 AM

    Rest in Peace… True Legend

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    Mute Brian O'Connor
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    Mar 22nd 2025, 9:45 AM

    Poor children of Gaza. Ethnic cleansing before our eyes. Same on us as human race. History repeating!

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    Mute Thomas O'Brien
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    Mar 22nd 2025, 10:48 AM

    @Brian O’Connor:
    Shame on you for using the death of a boxing legend to make a political statement.

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    Mute Lin
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    Mar 22nd 2025, 11:33 AM

    @Brian O’Connor: take a day off Brian, this is about a boxing legend not your soapbox.

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    Mute Alan Ely
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    Mar 22nd 2025, 7:44 AM

    Ah no absolute savage in the ring pure humble gentleman outside it . If I remember correctly won his last heavyweight title in his forties against shannon briggs. Another legend gone, RIP big man.

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    Mute Daniel Gilroy
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    Mar 22nd 2025, 8:56 AM

    RIP Big George. Thank you for the memories. Sleep well.

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    Mute Brian O'Connor
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    Mar 22nd 2025, 10:09 AM

    And yes RIP George. Hopefully now looking down and put stop to killing of innocent civilians in Gaza, Ukraine, Russia and many innocents of Africa. What has this world come to. Anne Frank doesn’t need a diary .. she needs a phone . I wonder has anyone read her book. Has anyone read “my struggle” by that evil man, it’s so ironic ! I see it both ways and what’s going on now is devils holocaust without the fire. the most ….. that suffered now put their suffering on .,.,,, Jesus weeps today. It’s a shame if a true American president of peace was true he/she would call a halt now to death of innocent children. Shame on US saying soldiers killed on open fields but not a word of children born and unborn laying dead in mothers arms or dying in mothers womb because the vessel has died. I am for freedom and protection. Same on us as a world of supposing humanity. Same on us. As da Vinci said “I open my arms, my legs for world all to see, only you can draw perfection or imperfection” same on us as a human race. A world of love is needed right now ! Has there ever been a time in history of love.? I think Anne Frank is hoping some day.

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    Mute Phillip Smyth
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    Mar 22nd 2025, 10:27 AM

    @Brian O’Connor: time and a place{champ}

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    Mute Thomas O'Brien
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    Mar 22nd 2025, 10:30 AM

    @Brian O’Connor:
    Jesus Christ , is nothing sacred.
    You forgot about the innocent people murdered by Hamas.

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    Mute damien leen
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    Mar 22nd 2025, 11:07 AM

    @Phillip Smyth: Normally I’d agree however try reading the article from a bit earlier labelled Palestine, a report from an English doctor at an A&E during the recent attack by Israelis…deeply disturbing! Needs to get highlighted everywhere at every opportunity.

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    Mute Thomas O'Brien
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    Mar 22nd 2025, 11:19 AM

    @damien leen:
    Rest in peace George Foreman.

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    Mute damien leen
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    Mar 22nd 2025, 11:20 AM

    @Thomas O’Brien: So you condone this response by Israel? This is Genocide you absolute muppet. These people are being bombed out of existence. They were dumped into Gaza, described by outsiders as an open air prison after they had their lands illegally taken off them & and when they fight back this is what happens!
    You are Irish yes? Do you have any clue of Irish history?! Armed resistance, armed struggle…

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    Mute Mr. Biggins
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    Mar 22nd 2025, 12:27 PM

    @Brian O’Connor: wtf is actually wrong with you? Are you related to Sinead, the header of this low grade rag?

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    Mar 22nd 2025, 12:34 PM

    @damien leen:
    7th of October ring a bell.

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    Mute Phillip Smyth
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    Mar 22nd 2025, 1:32 PM

    @damien leen: so normally you don’t agree when legends die to highlight your platform, so your selfish and foolhardy.

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    Mute damien leen
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    Mar 22nd 2025, 4:11 PM

    @Phillip Smyth: Toughen up a bit you child!

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    Mute Setanta O'Toole
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    Mar 22nd 2025, 9:06 AM

    Poor ol’ George. He was one of the good guys. RIP.

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    Mute Michele Milne
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    Mar 22nd 2025, 9:01 AM

    Ahh bless him!. I’ll always have a little piece of him in my kitchen ….rest in peace George ps thanks for the yummy toasties!!

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    Mute Bren
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    Mar 22nd 2025, 8:22 AM

    What a loss such a legend, RIP

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    Mute paul hayes
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    Mar 22nd 2025, 11:20 AM

    Remember watching him win the world title at 45. I thought 45 was so ancient. 47 year old me regrets such thoughts

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    Mute Robert Halvey
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    Mar 22nd 2025, 8:29 AM

    Oh what a boxer ,thanks for all the memories, and love and respect to your family and friends

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    Mute Oh Mammy
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    Mar 22nd 2025, 7:23 AM

    Rumble in the Jungle. I will.never forget it. RIP Sir. Say hello to Mo when you get there.

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    Mute Dermot Blaine
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    Mar 22nd 2025, 4:07 PM

    @Oh Mammy: Muslims can’t get into christian heaven, apparently.

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    Mute Rory Murphy
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    Mar 22nd 2025, 10:07 AM

    An icon of the sport.. Rest easy George.. A true legend and gentleman. Followed his career and interacted with him on Twitter .. feels like I knew him personally.
    What a great great man..Rest in Eternal Peace.

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    Mute Jack Schitte
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    Mar 22nd 2025, 12:44 PM

    R.I.P. George.Another Legend Gone.

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    Mute Geraldine O'Riordan
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    Mar 22nd 2025, 11:09 AM

    God love anyone trying to trace that family tree in the future.
    5 sons, all named George.
    A brick wall for future family historians

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    Mute Manc Chris
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    Mar 22nd 2025, 12:03 PM

    A Boxing colossus that returned to the ring in his 40’s to win it again. Truly amazing. RIP.

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    Mute Kieran Stafford
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    Mar 22nd 2025, 10:54 AM

    Would have reigned for 10 years if not for ali

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    Mute William Jennings
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    Mar 22nd 2025, 1:00 PM

    I actually think that George Foreman was the greatest boxer to ever step into the ring. His granite chin was simply unmatched and he had the most powerful punch out of any of the big boxers. To retire and then come back to become the heavyweight champion at 45 showed this. Foreman demolished every fighter that he came up against and had a reputation for being one of the most decent and kind individuals in professional sport. I’m also indebted to him for the Foreman Grill, it really helped me lose weight. RIP George Foreman, you will be missed.

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    Mute Kieran Horgan
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    Mar 22nd 2025, 1:12 PM

    A brilliant man George inside and outside the ring what he did for the young people in Texas with a hard upbringing was inspiring, that is why George came back to boxing in the eighties to help them because what money he had made was gone. A legend rip George you will be sparring with Ali and Fraser in heaven

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    Mute Dermot Blaine
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    Mar 22nd 2025, 4:08 PM

    @Kieran Horgan: Ali was a Muslim who rejected jesus . Can he get into christian heaven?

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    Mute Alex Marquis
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    Mar 22nd 2025, 10:10 AM

    A fantastic athlete. Just a question, how did he name his daughters? Georgina?

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