CLASSIC 09: OPRAH WINFREY

WHAT I KNOW FOR SURE

28 February 2022

On today’s Classic episode, Preston Pysh and Stig Brodersen decided to read billionaire Oprah Winfrey’s book, What I Know for Sure, that originally aired back in March 2016 as episode 77. 

This was such a surprisingly wonderful book. It’s not the book you want to read if you want to be successful in business, but the book everyone – really everybody – should read to be successful where it really matters, to be successful in life. 

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IN THIS EPISODE, YOU’LL LEARN:

  • Why Oprah turned 40 before she learned how to say no, and why you should practice it now.
  • Why you shouldn’t enter any relationship with the intention to change that person.
  • Why what you fear the most always materialize if you let it cloud your mind.
  • Why you should embrace the truth of your past and let it set you free.
  • Why you should show true gratitude without expecting anything back in return.
  • And much more.

TRANSCRIPT

Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

Stig Brodersen 00:00

On today’s Classic episode we decided to read billionaire Oprah Winfrey’s book, What I Know for Sure, that originally aired back in March 2016 as episode 77. 

This was such a surprisingly wonderful book. It’s not the book you want to read if you want to be successful in business, but the book everyone – really everybody – should read to be successful where it really matter. To be successful in life. 

We will learn: 

  • Why Oprah turned 40 before she learned how to say no, and why you should practice it now.
  • Why you shouldn’t enter any relationship with the intention to change that person.
  • Why what you fear the most always materialize if you let it cloud your mind.
  • Why you should show true gratitude without expecting anything back in return.
  • And much more. 

So with all of that said – I hope you enjoy the episode as much as Preston and I did it reading the book. Here we go. 

Intro  00:06

Broadcasting from Bel Air, Maryland, this is The Investor’s Podcast. They’ll read the books and summarize the lessons. They’ll test the waters and tell you when it’s cold. They’ll give you actionable investing strategies. Your hosts, Preston Pysh and Stig Brodersen!

Preston Pysh  00:29

Hey, how’s everybody doing out there? This is Preston Pysh. I’m your host for The Investor’s Podcast. And as usual, I’m accompanied by my co-host Stig Brodersen out in Denmark.

We’ve got an interesting billionaire to talk about for this episode. And it’s not somebody that we’ve ever talked about on the show before, and that’s Oprah Winfrey. I know some people might be, “Really?” Oprah Winfrey is a billionaire. I’m seeing $2.9 billion is how high her net worth is. And she just has an amazing story and to be quite honest with you, I’m a huge fan, absolutely huge fan of Oprah Winfrey. I’ve been impacted by a lot of the books that she’s recommended through the years. And we’ll kind of get into that as we go through the episode.

But she wrote a book and so we’re reading her book. And the name of the book is “What I Know for Sure,” by Oprah Winfrey. Fantastic read. I’m just thoroughly impressed with her in general. So I’m not surprised that her book was so good and beneficial, but we’re going to go through that. And we’re going to talk about the different things that we learned in her book, and it should be a pretty fun episode.

You know, I think a lot of people in our audience are value investors and people that are probably more on the accounting side of the house. And you know, not every person that you study has to necessarily be this mathematical kind of figure out the intrinsic value of something to necessarily add value. And so that’s why we’re kind of stepping away from that for one episode. And we just want to dive into just looking at things from maybe a different perspective and kind of seeing how she kind of rose to the top and maybe some of the ideas that helped her rise to the top A lot of that is covered in this book. So it should be pretty good.

I wanted to talk a little bit about her as a person, and how she grew up and what kind of background she came from. And unless Stig has any opening comments that he wants to throw out there. Do you want me to roll right into that, Stig?

Stig Brodersen  02:16

Yeah, that sounds cool.

Preston Pysh  02:18

I just wanted to talk about how she came from nothing and created this multibillion-dollar empire. I think that that’s just so fascinating. One of the things that I don’t know if you’ve noticed this or not, but one of the things that Stig and I like to focus on our show, is we want to focus on billionaires that created everything from the ground up on their own. We don’t focus on the Walton children, for example. I mean, they’re billionaires, but their dad, Sam Walton, was the one that created all the value and them just kind of fell in on it. So we like to find self-made billionaires or people that have kind of created all the value themselves. And that’s whom we try to like the study.

So Oprah would definitely fit into that category. She was born in Mississippi. She was born to a single mother. Her mother was a maid and just came from not too much. And there was a part that I read that her grandmother used to make like dresses or something like that out of potato sacks for her when she was a kid. She was so poor. And so what’s amazing, as she went into broadcasting, and she started off as kind of this radio announcer and she talked about this a little bit in the book of just how much she loved doing that. And she talks about having, you know, a couple of different jobs like working in a store, like stocking the shelves, and like after the second day, she’s like, “This was just so miserable.” And then she had this opportunity to tour a radio station and the gentleman who was giving the tour offered her the ability to go up there and read something on the audio and she was just hooked.

She was hooked from that point forward and just quite an amazing story. She just talks about the feeling that she got when she was doing it and how much she just loved it. Well by 32 years old, she had her own talk show, and her kind of had progressed on to TV. But when she was 32 years old, she became a millionaire at that point, and then by age 41, just a decade later, she had a net worth of 340 million dollars, which is just incredible. By 2000, $800 million. And then she was negotiating her own deals, own the rights to the programs and all sorts of things.

Now, let me get the number here for you. 2008 I think there’s an interesting number. It says her yearly income had increased to $275 million a year, by 2008. So Oprah Winfrey was able to create an enormous amount of value by the way that she’s talking on the show and just the ideas that she presents.

04:42

Now, one of the interesting things about her is she talks about this experience, and some people might have heard this in the media before, but she talks about this experience where she was on the show, and there’s a little bit of this in the book, and she was there interviewing this woman and she brings out this man on the show. Just kind of like straight like the 1990s.

Oh, who’s the guidance? Stig probably won’t know, because he’s never watched some of these shows.

Stig Brodersen  05:07

Unfortunately.

Preston Pysh  05:08

She’s talking about how she had this woman on her talk show. And they brought out this gentleman who was the husband of this woman that she was talking to. It just turned into this big eruption. And just like, she was looking at this lady, and she could see that she just like totally destroyed her entire life right in front of everybody, in the whole nation. And she remembers that feeling and just feeling just so bad and horrible about it. She had vowed to herself, “I am never going to do this ever again in my life.” And it was this major changing point for her that she realized what kind of reach, I guess, that she had, and she has the opportunity to either create good for the world or create badly.

So that was a huge turning point for her and she kind of went on this excursion of trying to understand how can I do that with this enormous audience that I’ve been afforded? How can I do good instead of bad? And I just have so much admiration for a person that doesn’t look at that. It just shows you how empathetic she is. And it shows you how she’s kind of looking at things like, “Hey, I’m doing bad here.” Like she can feel it. She can sense it. She has a very strong intuition. She talks a little bit about that in the book as well. So that’s kind of the intro of how she got her start. And what’s great is the name of this book. So let’s just dive into how she structured this book and what it’s all about.

The book is structured in a manner that each little tidbit isn’t that long. It’s probably like two to three pages, each little thing that she’s saying that she knows for sure, but she has them arranged in a manner that kind of makes a lot of sense, and it’s only a few chapters. So I’m going to read what the categories are in the book. The first one is joy. The next one is resilience. The next one is connection, attitude, possibility, awe, clarity, and power.

05:57

So she has little things that that are like little stories that fit in each one of those categories throughout the book. And to be honest with you, after reading this book, it was just phenomenal. I absolutely loved this book. So I’m curious, Stig, did you like it as much as I am boasting about this book?

So the name of the book is “What I Know for Sure.” So how did she come about with that title? So at the start of the book, she says that she was interviewing a very famous film critic from the Chicago Tribune, and many people might know who this is, Gene Siskel. At the end of the interview, Oprah says “Everything was going perfectly smooth until the time came to wrap things up. Then he said something that I would never forget. He said, ‘Tell me, what do you know for sure?’ And he just kind of said it again. He says, ‘I’m asking like in life, what do you know for sure.’” And she was just so floored by the question just like, “Wow, did you ask a deeper, profound question?”

And so she didn’t have a good answer for him. She said what she did do after that question, it has made her think. And she was just like, that was such a profound question. She started writing down little tidbits. As she went through her life, she would write them down, like what she knew for sure. And so that’s what this book is all about is what does she know for sure about life.

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BOOKS AND RESOURCES

  • Oprah Winfrey’s Book: What I Know for Sure – Read reviews of this book.
  • Raymond Moody’s Book: Life after Life – Read reviews of this book.
  • Gary Zukav’s Book: The Seat of the Soul – Read reviews of this book.
  • The Investor’s Podcast’s executive summary of the book, What I Know for Sure.
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