💸 From poverty to billionaire

GM. This is Work "After" Work, the newsletter that’s freaky fast and always fresh.

Call us the Jimmy Johns of newsletters, we won’t stop you.

Here’s how we’re starting the week:

• 💸 Billy of the month

• 😂 Meme of the day

BILLY OF THE MONTH

Since you guys liked the last billionaire of the month so much, I’m bringing you another and boy are you in for a treat.

Just like last time, I’m going to give clues about this person and you try to guess who it is.

Ready? Ok, this person:

• Has a net worth of $2.5 billion

• Was the first woman to both own and produce her own television show

• Has been on over 230 magazine covers

• Has a $45M estate in California and over 1,000 acres in Hawaii

• Has given away 570 cars

Any guesses??

If you said Oprah, then you my friend are a good guesser. That, or I just give too many clues.

Everybody loves Oprah and for good reason. She grew up dirt poor in rural Mississippi wearing potato sack clothing to school because her family had no money.

Miraculously though, she still figured out how to donate $80M to worthy causes. Now that’s nothing short of extraordinary!

And today I want to unpack her story and what we can learn from it so that maybe we can have just a sliver of the wealth she has.

So let’s jump in! Here’s the cliff notes version of her backstory:

At 17 Oprah started doing beauty pageants and won Miss Black Tennessee at 18. She then went on to get a degree in speech communications and performing arts.

At 19, she became the youngest and first African American woman news anchor on TV. During this time it’s reported she struggled to show objectively. From what I can find she was showing too much emotion and they wanted her to be a robot just telling the facts.

Oprah didn’t like this very much and Ariana Grande’d them with a “thank you, next” and created a show called “People Are Talking” when she was 23.

It was a more casual and improv type show - something she could actually show emotion in and thrive.

After 3 years, she was beating Phil Donahue’s ratings, who at the time, was the biggest talk show host on TV.

She does this for 7 more years and in 1986, when she was 32, got her own show named none other than the “Oprah Winfrey Show”.

When this happens she puts on her business savvy hat and starts a production company alongside it called HARPO, Oprah spelled backwards, to produce her show.

Her show obviously crushes it. They had:

• 28,000 guests over the lifetime of the show

• 5 president on

• 20,000 fan letters

• And the finale had 16.4M views

She essentially started what it even means to be an influencer today. The real OG!

And of course, being the businesswoman she is, she didn’t stop there. At 42, she created her book club that has made publishers $175M.

Then launched Oprah magazine and started a radio show.

After a long 25 seasons on air, the Oprah Winfrey Show ended and if you couldn’t guess, Oprah’s still been winning on all fronts.

She still owns 80% of HARPO, which has collectively done $2B in profits, invested a 10% stake in Weight Watchers and the stock 6x’d within a year, and sold a majority share of OWN (Oprah Winfrey Network), a cable channel she started along the way to Discovery.

Oprah has had a massively successful career and I think there’s two big things to take away from it:

#1 Creating a brand is extremely valuable

If Oprah wanted to create a syrup, it’d be the fastest growing in the country. Why? Because she’s built a stellar reputation that people trust.

It takes time to build but once you do the margin for error is massive compared to those without it.

#2 Be Bold

I’m sure it was tough going out on her own and trying to make it work with little support, but she did! And I think the saying “fortune favors the bold” really rains true here.

It’s tough to make that first step but you never know where it might lead.

I hope you enjoyed our second “billy of the month”! Be back next month with another!

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MEME OF THE DAY

😂😂

That’s a wrap ladies & gents!!

DISCLAIMER: None of this is financial advice. This newsletter is strictly educational and is not investment advice or a solicitation to buy or sell any assets or to make any financial decisions. Please be careful and do your own research.