The Press Box - MS NOW’s Stephanie Ruhle on Trump’s Billions, the Biggest Issues of the Midterms, and Moving From the Business World to Cable News

Episode Date: July 23, 2026

Today on The Press Box, Bryan is joined by MS NOW's Stephanie Ruhle. They talk about the money Trump has made in office, working in investment banking before getting into media, the purpose of cable news, and much more.Host: Bryan CurtisGuest: Stephanie Ruhle Producers: Isaiah Blakely, Jon Jones, and Lucy Brick Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Hello media consumers. Welcome to Pressbox. I'm Brian Curtis and I am back at Spotify headquarters as we continue New York month here on the press box. We've heard from the movie critic Richard Brody from Frank Miller, the comic book God who was shaped by New York's main streets. But New York is also the headquarters. of cable news, and I wanted to talk to somebody from that world. I wanted to talk to MS now host

Stephanie Rule. Stephanie Rule hosts a show every weekday morning at 9 a.m. called Money Power Politics, but she's had at least two careers. See, fresh out of college, Rule spent more than a decade in investment banking, and then at age 36, she suddenly decided she wanted to be a media person, and she became one almost instantly. In 2016, she joined what was then known as MSNBC. in the middle of one of the most consequential elections in American history. Now, part of the reason I wanted to talk to Rule was a question I've been thinking about this month, one that ties her two careers together. Last year, when he was president, Donald Trump made nearly $2 billion.

It's a mind-blowing amount of money. How do you explain it so viewers can truly understand it? Fortunately, our Trump self-enrichment explainer has arrived. Here's Stephanie Rule. Stephanie, thanks for coming by our New York headquarters. How nice were they? Thanks for having me. You reminded us on TV today that there are just 104 days until the midterms. And tomorrow I'm going to remind you there's 103.

Three days until the midterms. What do you think the midterms are going to be about? What I actually think everything is about, which is money. 16 years ago, Citizens United was signed. There's an unprecedented amount of money in these elections. Right. Thomas Massey in Kentucky just had the most. expensive primary race just a few weeks ago, I would argue the biggest donors to that race that

led him to lose have never set foot in Kentucky, nor will they ever. We are living at a time where we are seeing an enormous amount of money from the tech community, from the AI community, from the predictive markets community, right? It was just reported that CalShe, in the first half of this year, put $1.8 million towards their political lobbying efforts. That's more than double they spent all of last year because we're in a unique moment with the president where you can truly influence policy with money and we're seeing it play out. Do the Democrats have a unified rallying cry about money or is the rallying cry vote for us? We're not Donald Trump. They don't have a union. Listen, I think for any Democrat that wants to win, there's two things. It's affordability and

accountability. What are you doing to make life more affordable for the American people? Right. We already were dealing with an inflationary. environment during the Biden administration. We had a K-shaped economy where the rich we're getting richer, the poor getting poor. That's supercharged in the era of Trump. And if you can actually address affordability, and listen, everybody blames whoever's in the White House if they're having economic struggles. You can't normally point to a president for what's happening in the economy, but this time you actually can because the president's signature policy, his first year with the tariffs, that's made life more expensive. The signature thing that he's working on right now is the

war in Iran. That's making life more expensive. So they have to address affordability and then accountability. All that the president is doing, whether it's the grift or amassing more power, the American people want him held accountable and Democrats need to articulate how they're going to do it because Joe Biden did not do that. When he was running against, I was going to say when he was running the first time, but that would be 50 years ago. But when he was running against Donald Trump the first time, he said, look at all this self-dealing. Look at all these attempts at Gryft. Look at all this family members around him.

I'm going to close these loopholes so whether it can't be Donald Trump or anyone else to do this again. Democrats didn't do anything about it. And now Donald Trump has torn that open as he's making and his family billions of dollars. So Democrats who want to win, I think you have to lay out those two things. But they absolutely don't have a unified message. And the other thing that I don't know how they address, many Democratic candidates are picking up a lot of steam when they're saying, I want to get money out of politics. I want to get corporate donations out of all. But here's the thing. How do they do that?

This falls into like a hate the game, not the player. A week ago, the Supreme Court made a decision that only makes it easier for big money, dark dollars to go into politics. So you can talk a big game and say, I don't want those corporate dollars. And for some unique political candidates here in New York city, Zora Mamdani, whether you like him or not, has unique and extraordinary political power to rise to the prominence in the way that he has. There's not a lot of politicians. Again, you could like him or hate him. You could like Donald Trump or hate Donald Trump, but much like Mamdani, they're uniquely talented politicians. So if you figure that the majority of politicians do not have that charisma, do not have that branding ability, do not have that

ability to sort of connect with the American people like those two have successfully done, then you need a lot of money to win. And so I don't know how you can say, I don't know how, listen, I would love to see big dollars out of politics. I would love it more than anything. I don't know how you can do that and win at a time when there is so much money coming in on the other side, like a title wave. Two questions about money and accountability.

I want to ask you about this as someone who is in the business world and understands how a trading desk works. What did you make of the news that Trump is going to sell early access to his true social posts? I mean, it's so next level. I mean, it's like we're not even doing this quietly. It's so crazy because let's just explain what they're, the president has proven, right? Back when the tariffs, back during Liberation Day and, you know, when they coined the term Taco, Trump always chickens out, right? suddenly the markets are shaky and that the one guardrail Donald Trump has shown himself to have

is when those markets drop, he will run in with an announcement and fix it because that's the one thing he doesn't want to mess with. He has now seen time and again he makes an announcement and it moves markets. Now, if you were to run a long-term business, Donald Trump's erratic statements, his zigzagging on policies would make it so difficult for you to run your business to figure out what your supply chain looks like, what you're ordering, who you're hiring, if you're growing, if you're laying off. But if you're an investor, if you're a trader, if you're a trading platform, and a trading platform, remember, you're the ticket taker. You're just a middleman. You get paid no matter what. The volatility is great for you. So now you have truth social, right? Where the parent company

that Donald Trump is the largest shareholder of, now looking to potentially sell for a cool 100 grand a month to give you early access to his social media posts and others, when those posts, if you have that information early, can make the difference with you. Suddenly, if they're going to announce, we're not going to let any foreign drug companies sell drugs in this country, and we're going to go only U.S. manufacturers and the U.S. is going to invest in them. I'm making that up. But if we're the president, if you were to lay that out, boom, you would move markets. And imagine if you had that information before I did. And there's been a lot, I think it was the Washington Post that reported it last week. D.C. is getting trading fever. More and more people in the

government universe are just sort of adopting like that if you can't beat them, join them. And they're starting to play in these predictive markets. And it's funny, you know, last week when Donald Trump's teleprompter operator was put on leave and he's being investigated for making $100,000 for for making bets on things Donald Trump is going to say, that to me, they made that boy the sacrificial lamb. Okay. so, so, so, so many of them are playing this game. And they're like, who's the lowest man on the totem pole? Let's let him go down for everybody. So they're trying to put on a show like, well, we've got ethics here, but like, my gosh.

Would you make of Wall Street and the business community's reaction to the news that Trump is selling those? It blows my mind. They said nothing, nothing, nothing. And it's hardly like big-time investors. It's hardly like bank CEOs or private equity giants don't like the spotlight. You have some private equity firms that now have their own TV studios in their offices. You've got their CEOs making funny Instagrams. You've got them getting interviewed running in the park and not one of them.

Lots of them like to weigh in on all sorts of issues where they have absolutely no expertise, but they believe because they're titans in business that they're experts at everything. Yet this, what they actually know about, what they've live and died by their entire careers, they're not saying word one. that is so telling whether it's of them or the environment that we're in, that it is true when you do say something critical about this president, he comes for you. Elsewhere in money and accountability news, for those people who missed Donald Trump's financial disclosures earlier this month, how much did Donald Trump make last year?

Well, a billion eight, I want to say. It's well over a billion. And the money came from? A large portion of it was from crypto. I mean, some of it is an old school real estate holdings, but so much of it is coming from crypto and investing. And if the White House were here, they would quickly have the disclaimer and say, the president has his money in a blind trust. He doesn't have anything to do with the investment opportunities.

However, here's what's really important about it. There are many, many business people that have gone into politics. There are. And there's many business people that after they're in politics make a lot of money. Right? I was at an event not many months ago in the Treasury Secretary who was asked about this general subject got super defensive

and said, well, what about Obama? When he left office, you know, he got that Netflix deal. After he left office. Seems like an important point. When the president, and the president says it often, like, listen, people don't mind if I'm making money as long as they're making money. Look at the markets.

Here's where he's mistaken. This is not just about who's making money. When the president is making deals that we're concerned that he's not putting country first, that he's putting sell first, that's when there's a national security risk. That's when there's a transparency risk. When suddenly he's saying, we need these drones.

We're going to, the Pentagon is going to commission this drone company. And then you find out Don Jr. is invested in that drone company? Then the question is, is this the best company we should be doing business with? The issue more than anything is transparency. No one is saying, I'm certainly not anti-capitalism by any means, right? I have the pleasure, the honor of getting to live the American dream. I want the next generation to get to do so. This issue is we are watching this administration time and again.

It's one of the reasons why the president loves tariffs, because it's not just what country is being faced with tariffs. The real reason he likes it are the exemptions. It's what actually gives Donald Trump the feeling of being a kingmaker that he can sit on his essential throne in the White House and foreign leaders and business leaders come in and saying, please, sir, give me an exemption. And the answer is, what can I give you on the other side?

I know CEOs who have met with Howard Ludnik, who have met with Scott Besson and their teams. And the message that comes out is sort of like, well, is there something that you could offer this White House in no uncertain terms? And imagine if you're not the biggest company out there. Right? So just think about the tariffs.

If I'm Walmart, if I'm Target. And people say, well, the tariffs didn't really impact them. They didn't raise their prices that much. Babe, they didn't have to. They control the supply chain. They knew the tariffs were coming. They could pre-order every Christmas toy there is. They've got massive warehouses to do that.

What if you're a toy store on the Upper West Side? What if you're a bookstore in Philadelphia? You cannot control the supply chain like that. So what we actually end up seeing is the big companies get bigger and more powerful. And the small companies simply say, I'm a tiny business. I don't have a war room to figure out how do I redirect my supply chain to change from producing toys in Vietnam and now Guam. They can't do that.

But if you're the biggest retailers, if you're the biggest businesses, you could figure that out. And the sad thing is half of this country is employed by small businesses. We talk such a big game that, like, we love small business in this country. We want to keep Main Street USA, you know, alive. And as we say that, as we write that tweet, we're stepping over seven Amazon boxes to get to our cars. And again, I'm not trying to say, I'm not shopping at Amazon. I certainly do. There's probably nine in front of my door right now.

I'm just saying this is the reality of what we're living in. Does profiting from being president, at least on this scale, go away when Trump leaves office or has he changed things? Do you think for future presidents? That all depends on who's elected next. Like, as I said earlier, I think the American people are sick of this. Donald Trump can say all day long this isn't bothering anyone, it is. And when we, there are more and more people saying

this system doesn't work for me, right? It's why you're seeing, right? And it's not just like, oh, is this Democratic Socialists getting ahead? It's more and more voters just saying this system. Lawmakers on both sides of the aisle, when we just looked at these primaries, you had people like Michael Bennett in Colorado, who's a longtime centrist Senator Luz to the Attorney General in Colorado,

who wasn't a super progressive, but that attorney general said, I'm not a Washington insider. I'm going to get something done and I'm going to fight Donald Trump. And I'm a big Michael Bennett fan. I'm just trying to say like this snapshot. It's not that the Democratic Party is unified, that they're all going the way of Mamdani. But I think that so many voters are just saying,

this stinks. This system does not work for me. And the funny thing is, that's how Donald Trump originally rose to power. His original base was decrying so many of the same things that we hear now from people with no affiliation with MAGA. Young people were saying, hold on a minute. We just got another report that said the Social Security Trust is going to run out one year sooner than we thought it was. So if you're a young person now, you're like, why exactly am I paying into Social Security?

If you're a young person now, right, how old were you when you bought your first apartment or your first house? I bought my first house in my 40s. In your 40s. Yeah. So right now, that's where we are. Right now, the median first-time home buyer, or that could be an apartment, is 40 years old. It was 33 years old five years ago. And when people are buying their first homes later and later, it's not just about them not making roots.

That impacts a whole economic ecosystem. People aren't moving to towns. Then they're not buying a washer and dryer. Then they're not buying a car. They're not being part of communities. And so as the world is getting more and more expensive for people to start out, that's why so many people are saying this system doesn't work for me. And I do, I'm not going to say worry, but I observe, it does feel like a reckoning is coming. So with that reckoning, what do you think Donald Trump has permanently changed about politics?

What will not go back to, quote, unquote, normal after he leaves office in 2029? I don't know the answer to that, because in many instances, I think he's one of war. one. I think Donald Trump's unique combination of brazenness, shamelessness, and his real talent for feeling the heartbeat of a room, like feeling the energy, like knowing where the grievances and tapping into it, is unique. Like, I can't point to that many other lawmakers that connect with people in the way that he has. What's the best thing Trump has done in the second term? For him or for the country?

For the country. Made people learn and care a lot more about civics and democracy. We had a dose of that in the first term. We had a dose of it. People caring more is a good thing. People wanting to be educated more is a good thing. Listen, I worry so much about disinformation and misinformation.

But I think more and more people, right, I look at my own kids. I look at my own teenage sons, and I could be panic-stricken over where they get their news from, or I could feel somewhat excited, which I do, that my boys are engaged. And trust me, there's a lot of fights at our kitchen table

when I'm like, I'm sorry, you think what? And where'd you get that information from? But I can tell you, there's a lot of topics that my kids know about and care about that I wasn't thinking about when I was 19, spent my summer on the Jersey Shore. Let's talk about your life and career. Grew up in Jersey. Sure did.

You once said performers grow up performing to be loved. Were you a performer from a young age? Always. And I think it's an asset and a long, sad liability when you think about the long arc of your life. I think that when all of your confidence comes from performance, right, you're not performing for yourself, you're performing for others. You're performing for others to say you're smart enough, you're funny enough, you're cute enough, and most importantly, you're good enough.

And I think that's a huge driver and a motivator. You see tons of really competitive people that have that in them. But I certainly hope and pray for most of those people, and I pray for it for myself every day that I can get past that. because I think that people who actually have success and peace in their life are people who aren't performing for anyone. They're people who believe that they're good enough. And when I think about a lot of the people who I've covered in business, something that makes me sad is I look at some of the most successful guys I've covered, and I look at them, and they're just performing for others, right?

And it's not on a stage, and it's not with a TV camera, but it's a number next to their name. And I look at these guys who have more money than they could ever imagine. Their grandchildren's grandchildren will not ever have to work. But instead of them sitting on their 70-acre estate in Sun Valley, they're on a plane, three out of every four weeks a month, trolling for more deals, trolling for more deals, because they're performing for others. And I think that actual success shouldn't just be about this public achievement. And when we think about what success looks like, it should really be.

about finding some level of peace. And I know, like, for me, that's certainly what I'm aiming for. I've definitely not achieved it. But even just think about this show. You think about this show that you're doing. If you actually believed in yourself, it wouldn't be this panic of who am I going to get on the show? If I get a big guess on the show, the show is going to matter. If I get a big guest, then I'm going to make news, then it's going to matter.

When I was launching Money Power Politics, just a few weeks before the show launched, somebody in my family got really sick. And so for the three weeks leading up to it, I get really distracted. And normally, like, I'm a hustler. I'm a power booker. You know, when it comes, like, who are you going to get on your show? And it was a few days before the show, and a mentor of mine was like, your show is about to launch. Like, what do you want?

What do you hope? And I was just like, I was thinking about so many personal things. I was like, I don't know. Like, I don't know, the night before Trump calls me and says, like, what does he call me? Stone Cold Killer. Hey, there, you're a stone cold killer. You got a show launch tomorrow. I'm going to come on.

And I said to this mentor of mine, I don't know, I guess I'd like to have Trump. I guess like I'd love it if Jamie Diamond would come on with me. And this person said to me, God, I wish you would stop thinking that way. And I was like, why? Everybody wants a big guest. And he said, yes. But if you actually believed in what you're making, then somebody would tune in for you. And not because like, you're amazing and you're dazzling, you're this, but because you trust

them and you care about them. In the 1980s, America's most trusted person that took a poll was Johnny Carson. And you know why? Because people when they watched Johnny Carson were in their beds, they were on their couches, it was 11 o'clock at night. The show that I just slept was on at 11. It was one of my favorite parts of the show

that people aren't watching it in the back of, you know, as background noise or it's not on in the dentist office or in the chair, they're choosing to watch it when they're home. And I'm just saying when you look at people who in media long term, you really grow to trust and care about, and I think about people I look up to Hoda,

I look up to Lester Holt, I looked up to Savannah. I look up to Rachel Maddow. And when I think about, oh my gosh, what did Rachel do on the show that was amazing? It was never, remember that day she had that big guest. It was no. Over time, you're watching this person

that cares about the content, that understands the content, that understands the truth, and they care about you. You know, like for Hoda Kotby, she was in the business for, I think she was at NBC, maybe for 18 years before she got the Today Show.

And all those people now want to develop a brand. She didn't develop the brand of joy. She is joyful. She truly cares about the people around her. And it emanates. And so I think people who are really successful at life. And when you're successful at life, I don't think that there's lines between personal and professional.

It has to do with believing that you're good enough and just having that joy inside of you. When you were in college, you did study abroad. For a long time. You did enough studying abroad for about four people. I did. Italy, Kenya, Guatemala, Costa Rica. Where did that urge come from?

When I went to college, I was in my first year. I went to Lehigh University in Pennsylvania, and it's in a small steel town. And I had a sister who was just graduating from architecture school. And she just got her first job and learned that you got two weeks vacation a year. And she called me on the phone, and she was like, do you like school? yeah, it's fine. And I'm like, you know, fraternity parties, blah, blah, blah, blah, blah. And she said, I have two weeks vacation a year. And she said, you have four years. She said, go everywhere

you possibly can. Live all the lives you possibly can because once it's over, we've got to make rent. We have bills to pay. And so I did. I mean, the second my freshman year was over, I'd met the dean of the School of International Business at Lehigh. And I'm like, I want to go. And he helped me sort of create a program and I left and it was the greatest thing. I would never ever have ended up with my career in investment banking had I not. Had I gotten, let's say, I certainly did not get into Wharton. Had I gotten into Wharton, I wouldn't have gotten a job in investment banking. Because if I was a student at Wharton, I wouldn't have been in the top 10 or top 20 percent. I would have been in the bottom half of my class. And not every kid at Wharton gets a job in

investment banking. But then there's me, right? I'm living in Italy. I want to stay out of the country and I have no money. And I'm like, well, what can I do for a job? So I write Lehigh alumni who work in banks, letters. Because I'm like, well, they have banks all around the world. And I got a job at Merrill Lynch. And it turned out the job I thought was going to be overseas, but it wasn't. It was in New York.

And that just snowballed for me to end up in banking. And that resume that I had, that kooky weird resume, because I went to a non-target school that no one would have normally looked at if I just stayed at Lehigh and been in the journalism club. But they were like, who's this weirdo? who lived in Kenya and Guatemala and Costa Rica and Italy, let's bring her in for an interview. And it was that sort of unconventional background that got my foot in the door. And then it was me just being an unrelenting workhorse that helped me drive through it.

But I didn't have a background in finance or I didn't have an extraordinary expertise. And so there's very few things we have no control of. We have no control of time. We have no control of the weather. And the truth is we do not have control of our health. And to me, those are the three things that no matter what you have to honor. And so when I think about what I do with my time, I want to max it out and make the most of it. And I think, like, my college experience is the best example of how that started for me.

You've told a funny story about being at Merrill Lynch and helping a bunch of middle-aged dudes get dinner reservations. How did that work? I mean, that was honestly the secret of my success when I was really young. when I ended up on a trading floor, and a mentor of mine at the time was like, just figure out what they need, right? Like, you are not the person who's coming up with trade ideas. You are not the person who's writing a research report.

You're a 22-year-old girl sitting on a trading house. What do they need? And what do they need to do? They need to entertain four nights a week in New York City. And besides going to Nick's game or Yankees games, they want to go to hot restaurants and they want to go to hot nightclubs. And when I was 22 years old, yep, I read Barron's. Yes, I read the Financial Times.

No, I didn't know what I was reading in either one of them, but I read Timeout Magazine every single week. And I memorized Zaggots from the front to the back. And I met every doorman and every Mater D. And I figured out, and I got reservations at every hot restaurant, and I humiliated myself doing it. And I even convinced them, you guys definitely are not getting into this nightclub, the four of you wearing fleece vests and khakis before you head home to New Canaan. And I'm like, you're going to have to have a girl at the table. And it worked for me because then there I was, 23, 24. years old, but some of the biggest investors in New York. And like, my other option was being the person

on the phone saying, hi, Credit Suisse, and maybe someone would say two things to me, or you were sitting next to these people for three hours a night at restaurants. And I would leave, someone had given me the advice, never stay out after midnight, never drink, never drink at a work event, and never stay out after midnight. So I would go out, I'd set everything up, I would drink waters and say that they were vodka sodas. When I was old enough and they would give me a moment, and they would giving me one, I would either leave my corporate card there and get it the next day, or I would shimmy out at midnight and hope somebody was going to get the next bar tab. Welcome aboard Via Rail. Please sit and enjoy. Please sit and sip. Play. Post. Taste.

View and enjoy. Via Rail, love the way. Grigos believes in the art of living in choosing the pleasurable over the practical. It's why we craft our premium vodka in France using pure spleen water from Genzac. And why you hear the celebratory pub of our quirk, reminding us to make every martini cocktail count. So go on and make every moment count, because there's no better time than now. Grey Goose, make time wait.

Sip responsibly. The Hulu original series Furious is coming to Disney Plus, Starring Emmy Rossum, Furious follows FBI agent Alice Black on the hunt for a mysterious and calculating serial killer. Both walk their own paths toward justice, and as their lives start to intertwine, the line between right and wrong begins to blur. Don't miss the three-episode premiere of the Hulu original series Furious on July 27th, only on Hulu on Disney Plus. During your years in business, you were interested enough in a potential TV career that you tried to. out as the guest host on Live with Regis and Kelly, what happened there? Well, obviously, I didn't get it.

When I was 26, I was actually leaving Credit Suisse where I worked, and I was signing a deal to go work at Deutsche Bank, and it was a really big deal for me. And at the time, it was, I had a lot of early success in banking. I had, my most surprising success was sort of like my first five years, was like, I really shot out of the gate big. and I was leaving Credit Suisse to go work at Deutsche Bank and I was at this lawyer's office signing the contract and I'd never even met with a lawyer before

and first of all I call my parents to tell them I'm like signing this to your deal and I'm like, Dad, you would not believe how nice this lawyer's office is and like I didn't know, there was no camera phone yet but I'm like I'm like you know we're on the 48th floor and like they've got a fruit platter and they have this and my father's like you paid for the fruit platter do you have any idea how much this is costing you

he's like there's fruit there's cheese wrap it up and take it with you you just paid for it But anyway, I said, I'm leaving tomorrow. I'm resigning for my job tomorrow. I'm going to go work at Deutsche Bank. And I don't know how my parents heard it or how they knew it, but they heard on the radio that the next day there was an open call for someone to fill in for Kelly Rippa for a week when she was on maternity leave with one of her children.

And they said, the timing is perfect. There's an open audition tomorrow. How could you not go to it? So I'm like, you know what? You're right. So I go home My husband goes to bedbath and beyond To buy two like lawn chairs

We show up at ABC Studios at like 3 o'clock in the morning We sit there, we wait for hours He's like buying coffee and hot chocolate over everybody else in line I end up making it to the finals Like I make it to and when you make it to the finals You have to sign a contract that says If I win this I have to commit a week to ABC

Right so now I have to call Deutsche Bank on the phone Right? They're thinking we're taking a flyer on this 26 year old girl Who everyone says she's great in business but I'm not really sure, and we're paying all this money. I have to say, so I know we just went through all these negotiations and da-da-da. So by the way, I've got something going on, and if it works out, I'm going to need you to give me an extra few weeks before I show up. And this guy named Boaz Weinstein, who I was going to work for,

is still a great friend of mine. I tell him the story, and he's like, I'm sorry, what? And he's like, you've just sold yourself as like the greatest credit derivatives, hedge fund, saleswoman, since sliced bread. And now you're telling us you're not going to show up because you might get a gig on TV for a week. I'm like, yeah, I'm actually telling you that. And he was like, you know what? That is so crazy.

That is so like out there, but like, I don't know any chicks in TV. That would be really cool. Good luck. So lo and behold, of course, I do not win. But I always wanted to do it. And I think that people don't pursue their dreams when they have a day job because they have a day job. And then I had a couple of kids, but it was always like eating away at me. And I used to do TV as a guest.

I used to do some financial news. I used to do a lot of public speaking to try to get women to. to go into finance, to get girls, to want to study math and science. Because it's not that, I mean, especially because like when I worked in banking, I was in sales. I wasn't in trading. I wasn't in investing. And I'm kind of like, ladies, if you're going to sell something, sell the product

that pays you the most amount of money. Because, well, it's really fun to work in other industries where you might get free boots, work in an industry where you can pay for your own. And that was just like my feeling. And I felt like, I wasn't trying to say finance was a better industry than others, but I looked at my husband who went to an Ivy League school and played a sport at an Ivy League school. And if you did those two things,

there is an embedded, my husband played lacrosse in college. When he and I set foot on a trading floor, we were in the same training program that's where we met at Credit Suisse, when the two of us set foot on that trading floor the first day, there was a universe of 40 guys in the business that were in his network, and I'm not begrudging it, I'm honoring it, that were in his network who were like, Andy Hubbard just got here from Princeton.

I want him to come sit on my desk and I'm going to teach him about this. I'm going to help him out. Nobody was looking over at Stephanie Ruhl with her Ann Taylor Navy suit and her, you know, polo bag that she got free with a fragrance at Lord and Taylor in Paramus, New Jersey. And I envied and admired what they had. And I'm like, women deserve this. Not because not for some like giant DEI initiative that we've been wronged, but I was more just like, this is awesome.

I want to have this for my crew. And so I used to do, like I founded the Women's Network that we had at Deutsche Bank, and I just thought, this isn't an either-or, but what can we do to help one another, like get in this game and win this game? And so by doing a lot of public speaking and some media, it was just making me feel more and more like, that is this thing that I want to do. And I never really said it out loud that much,

because no one wants to say their dream out loud, because you feel embarrassed. You feel like a loser, and people make fun of you. Lots of people make fun of you, and it's not about you, though. It's because they're on a New York City diamond-encrusted gerbil wheel that they're afraid to get off of, because they have a job that they don't love anymore, but they now live an expensive lifestyle, and they can't leave that job that they don't love. But I worked in banking for a long time, and I was really practical, and I saved my money,

and I was married, so I wasn't all the income in my house, And then when I was 36, I was speaking at an event for a women's group. It wasn't a political group, but they were called the White House Project. It was a women's leadership group. And the woman who ran it, she now runs Tori Birch's Foundation. Her name is Tiffany Dufu. She said women and minorities always get lumped together. But if you take the 50 most powerful black men in the United States, they do more for each other than the 50 most powerful women.

She goes, women aren't out to get each other anymore, but we're not like really thinking strategically. And she said, everybody in this room, and we were all on the advisory board for this charity, she said, you each need to say what you want to do next, and someone else has to get you there. And I didn't even know what I was going to say. I honestly was like, I don't know, like play tennis with George Soros. I didn't know what it was. And I was like, actually, I've always wanted to work in the media. Since the financial crisis, banks have done the worst job rebranding themselves, telling their story,

and the truth is they finance the American dream. And there was a woman there who happened to run human resources. of Bloomberg. And she said, me, I'm going to be that person. And a few days later, I met the head of Bloomberg TV, who later took over NBC News, a guy named Andrew Morris and Andy Lack. And Andy said, in the new world of TV, there's no more teleprompter presenters. You're certainly not one. You came from print. And he said, in the new world, you have to know the content, love the content, and the audience has to want to have a relationship with you. And I said, I don't know about number three, but I have one and two, better than anybody else who works here.

and I would walk away from my career and do this, and you can pay me nothing to do it. And you can give me no contracts, you can fire me at any time. Because either way, I was taking a giant career leap. Like, tons of people want to say, like, I want to start over, I want to make that transition. People have to realize when they start over and they make a transition,

their income is going to go from here to here. Nobody wants that part of it. They're like, wait a minute, what? So how far down did it go for you? 50% pay cut? 95%? 95% pay cut from business. You got your last year in business to your first year in television.

90%? Yeah. Wow. And I had saved money for a long time. And again, I am lucky. I have a spouse who worked in finance as well. But that wasn't my idea. I actually, after I met with Andy, I went to go see a great guy in business. His name was Todd Bowley.

He owns part of the Dodgers, the Lakers. And he and I worked together at Credit Suisse. He then became extraordinarily successful, much more than me. And he said to me, everything is about risk management. And he said, you want this job in TV. You need to lower the risk for them, so it costs them very little for them to give you what you want. And I remember, I didn't even understand what he meant at first. And he said, tell them it's going to cost them nothing.

They could fire you at any time. But what are you going to get on the other side? Because you need more than just a job in that newsroom. And so I went back to Andy and I said, I know this is crazy. I've never really been on television. I need you to give me a show to anchor. But if it's a failure, you can fire me any time because that's the thing in TV. Everybody's on these long-term contracts.

Like once you're working somewhere, they can never get rid of you or it takes years. And so I said, pay me the lowest number, give me no contract. And the minute you don't like it, send me packing. Lucky me, they said yes. And as soon as I came, I co-anchored a show with an amazing guy named Eric Chatsker and two of their women. And I was sort of off to the races. And Bloomberg is a phenomenal place to work. and it was much easier for me to go to Bloomberg than NBC

because the thing in media is, I think the most important thing, is knowing your audience. And Bloomberg was a very easy transition for me because I was the audience. Before I went to work in television, I never even had an email address because I worked in finance,

so to my husband and everyone else. All I ever had was a Bloomberg terminal. All I ever had was a Bloomberg address, and I'm like, a Gmail account, I don't even have that. And if you understand the audience, if you speak their language, if you're bringing on the guests that they care about,

if you're telling the stories that they care about, and that was easy for me to understand because I was them. Fast forward, when I left Bloomberg and I came to NBC, my first job at NBC was one of the weekend anchors of the Today Show with Chanel Jones and Craig Melvin, who are phenomenal people and amazing colleagues. That was actually, even though in theory the content, is much lighter, easier content,

it was a much harder job for me because I struggled with who that audience is and what they want and where they are. And that's like what you really have to solve for, which is different from working, breathing, living in New York, in finance for a completely financially focused audience. And so then once I was at NBC, I did the weekend Today show for about six months. And I was also an MSNBC anchor, which was hard because I had no background in politics. and then Donald Trump became the nominee, and I was, dare I say, uniquely qualified

to cover Donald Trump, but I was in that I had no game with early Clinton, I was obviously not a DC insider. And I remember when I was first covering politics, I went to Brooklyn to Hillary Clinton's headquarters, and I had an appointment there, and I couldn't even get in the building. Like, I waited for an hour,

I didn't use any connections, and when I got there, they had me meet with like the interns, interns, interns, intern, and that was sort of Trump's magic sauce, his first time around, you could call him on the phone and he answers. And sort of that directness, you know, when people did like the Hillary Clinton autopsy of like the Hillary Clinton went to the Hamptons that August and she never went to Michigan and Wisconsin, I can tell you from like a coverage perspective, I can see it. And that like there was this giant political establishment that's like up here that like you can't even touch. And Trump was just like in your face, in your kitchen. And then it was, dare I say, uniquely beneficial for me.

Then he wins. And he's got the likes of Gary Conan's administration and Dina Powell and Steve Mnuchin and Jared Kushner. People either, I had either known for years or covered for years at a time when very few people knew them. And just from a, from a, I never covered Donald Trump when I worked at Deutsche Bank, but Deutsche Bank was even the place where he did all those banking. So I had like these strange threads to pull on and these strange advantages that I had a banked on because I was definitely an outsider covering politics. And so was he and so were many people in his administration. You said in an interview that the TV world is meaner than the business world. It is. How so? Well, it's different. It's passive aggressive, not aggressive aggressive. And I think

there's lots of people who would prefer passive aggressive. I'm just not one of them. And so I think in the world of TV, it's funny because, like in finance, there's more money to be made. And you might want to make the most, but everybody can, there's more deals to be had.

Everyone can make money. In TV, only two tushies fit in front of that camera. And TV is far more passive-aggressive in that, like, there's people in talent management. And then there's agents for agents and managers, and in banking, it's aggressive-aggressive. You don't like something?

I mean, it's obviously testosterone-led, but you are duking it out, fighting on the trading floor, and then the next day you're coming in and you all have a common goal of making more money the next day. And TV is just, I don't know, it's more slow pinpricks to death versus being bludgeoned in your heart. Both industries that I absolutely love in their own ways. You've also talked about having dyslexia. I do have it. A term that I think is really misunderstood by people. they think of, you know, sentences going backwards and numbers flipping.

Yes. How does it affect the way you prep for a show? So, I mean, I think that's a great example, and I think that's why so many people are undiagnosed. I mean, I wasn't diagnosed until I was an adult, until my oldest child was, in that we think, oh, it's got to be none. But for me, I have zero reading comprehension skills, none. And so the good part about it in TV and in life, it forces you to be a very active listener. and it forces you to be a performer. So like when I was in school, I was always,

and I didn't know as a dyslexic, but I was always gaming the system of, how do I take the class where there's a debate? How do I take the class where there's a presentation? How do I hustle this teacher and go to office hours to triangulate for them to tell me what's going to be on this exam? Because God help me if I have to read this textbook, I can read it 17 times and nothing is going to slide into this head.

So I just think that you find ways. I mean listen in TV it's so funny when I when when when I watch you know heroes of mine a lesser hold Dave Muir like I'm not your evening news anchor

who can who can present like that teleprompter no matter how many years I do this when I sit down that teleprompter is no friend of mine that is my enemy and I'm you know I look like I look like I'm in the movie a beautiful mind prepping for a big interview because I'm just writing my questions over

I'm writing the same questions over and over over and over and over. So when it's time for the interview, all I have is one index card with a few words and bullet points, and then I know where to go. And that's the same thing if I'm giving speeches and in the show, it's tricky. And when we prep the show, I don't read the scripts.

I talk about the show with my team, and I'm sure they're like, we're sick of doing this, but it's just the way it works for me. And I actually think the timing is right for dyslexics, because look at what you and I are doing right now. Look at where we're just having a conversation. And I think that that conversation is what resonates with people. It's what they, it's when we're not sitting up perfectly straight and reading a script,

when we are awkward and talking and saying, hold on, say that again, I don't understand. As a viewer and as a listener, that's when I become more engaged and less engaged with the white noise of TV presentation. So while being dyslexic doesn't make it easy. It's not the debilitating hurdle that one could think it is. Your network just celebrated its 30th anniversary. And the front end of those 30 years, cable news has this lock on everybody who wants news during the day. You're either watching cable TV or you're listening to the radio, basically. Now we live in a country of politics and the internet and social media and everything else.

What's the point of cable news in 2020 since? I don't think it's about a point of cable news versus network news versus podcast, versus radio, I think the barriers of entry for media have never been lower, which is extraordinary, because years and years ago, right, there were three newspapers of note. There was three television networks of note, and if you couldn't get into those organizations, you had no shot. I mean, I think it's beautiful that the barriers of entry are, I mean, listen, I bring so many people on my show today that come from the audio world, that come from the YouTube world. I think that's amazing. The fact that cable news doesn't have a lock on an audience means life's harder

and it means you got to be better. What do viewers want from you at 9 a.m. in the morning? I think people want to get smarter and better. I think people want to be informed. This idea that everyone is so angry, this idea that everyone is so biased or that the media is biased, yes, I think there's portions of it, absolutely. But I think a misnomer is this idea that the truth is bias. It's not. People just don't want to hear the truth. Some people don't want to hear the truth. And I think that I get that the excitement of going viral. I get that saying over the top incendiary things makes lots of headlines. I don't, I think that's a really, and you know, listen, maybe someone saying, you know what, 70, you're saying that from the cheap seats. You wish you're on

page six every day. I don't. I think what makes for like a long, beautiful. life and the privilege that we have to work in media, we have a chance to inform people. We have a relationship with our audience. And while we don't have the privilege of this being years ago when people had no choice, but to watch cable news or network news, I think the challenge now is to make something better, and we should rise to the challenge. You once said, I don't have any political ideals that I'm tied to. Is that still the case? I don't. And you look, what are you talking about? You work at MS. It's totally progressive. sure I want the world that we live in I want the world that I'm handing to my kids that you're handing to your kids is better than the world that you've got

and does that mean that we're calling leaders out whether they're in business or politics sure and I think it's exciting that we no longer live in a world where media is just a 29 minute show and we're just presenting a story and not giving any analysis right the beauty. is we can say, here's this unbelievable story that Peter Baker from the New York Times broke today. And then Peter and two of their analysts can come on and say, here's what this means. And so I think it's fair to say lots of people don't have an ideology. They want the world to be better and smarter, right?

And I think that over time, and these aren't my words, maybe they're Barbara Walters, but maybe not. Someone far greater and smarter and more accomplished than me once said that over time, they're not surprised that journalists become more progressive because they cover the human condition. Because every day, they're covering health care, education, crises around the world. And when you see what people experience, you care more. I remember the presidential historian, Doris Kerns Goodwin. I interviewed her at a private event a few years ago. And she had profiled and covered sort of every living president. And President Trump had won. And her,

concern was the one thing she didn't see in him that she saw in others was a lack of empathy. And she said other presidents, once they win and they actually get on that train and go across the country and go to hollowed out towns and see people after natural disasters, even if they were super privilege or disconnected, suddenly they really start to understand the human condition. They understand the awesome responsibility of their job, and that's when they really start to care for the country and govern the country. And Lawrence O'Donnell often says, once you win, your first job day one as a first term president is to win over the rest of the country. So you can now win your second term. And I remember Lawrence saying that was the difference he noticed in Donald Trump, because Trump one and two, his inauguration speeches, both times were a, or a,

Fire and brimstone, dark and furious, you know, antagonistic. And there were these moments of like, oh, he's not looking to win over the other happen. It was funny. After Trump won this second time, I called someone very close to him, who I knew from the first term. And I actually said, I'm like, you know what, we got it wrong. I definitely got it wrong covering. And I said, do you think this is, and it was an off-the-record conversation, off-the-record. I said, do you think this is going to be an opportunity?

for the president now that he's won, now that the pendulum has swung, and the country said, like, this is too much, we've gone too much in one direction. Like, do you think he's going to sort of pivot to the middle here? Or he's going to keep going as far as he is? And this person close to him was exploding

with anger on the phone to me. Like, why would he ever do that? Like, we have been vindicated. We are justified. Everything that was said about him is a lie. You were wrong. Now we've won. And I was like, oh my goodness, gosh. And then suddenly Doris Kern's Goodwin was in my mind. again of like now he has this chance like he won and but like this goes back to like I look at Trump

pushing these election fraud theories again and I don't understand it right like from a political perspective I think an amazing story if I were him would be like I won you guys made a mistake you voted me out of office you didn't have me for four years you knew you made a mistake and despite everybody going after me you voted me back in you saw the air of your ways I'm the man like the greatest comeback story. But instead of leaning into that, he's fixated on relitigating these election fraud lies, right? He's going down to Georgia to give a speech today about affordability, but you know he's going to be taught. I mean, like, this is where he started with Find Me the Votes. And so I think that it's funny he could tell this incredible story, but right now he's so fixated on being beloved and

winning and vindicated. I just go back to you don't have to have an ideology. You can root for America. And I think rooting for America and rooting for humankind is not a politically motivated or a biased thing. Just like I don't think the word patriot should be coded to one party or the other. And I certainly don't think the flag should be. All right, last one for you. You mentioned you were in sales when you were in business. We're all in sales every day. So that's where I'm going. You're doing a podcast. You're doing a TV show. You're selling the show. You're selling yourself. Did you find being a saleswoman in business? business was the same as being in saleswoman immediate?

I think they're all exactly the same. How's it? I think everything is about building relationships. And if you can build a trusted relationship, I think that's everything. And that doesn't mean you're not going to screw up. You can screw up. You can get things wrong. And I think it's the opposite of the desire to have a giant launch and go viral and be the

hottest thing. I think rather than break down the front door and say, I'm here, I'm winning, get used to it. What if you came in the side door? And what if six months in, suddenly somebody's saying like, wow, you're sitting next to me in my kitchen and you're my girl. You're the person I trust. You're the person I really like. Come with me. Tell me more. And so I think that everything, everything in life is how do you build trusted relationships. Media execs are okay with this coming in the side door, taking six months to build an audience and all that stuff? media exec should prefer it rather than someone's saying I'm banging down the front door and I want 17 billboards with my face on it

and 16 profiles. If you build it over time, doesn't that create a stronger foundation? Stephanie rules money power politics. It's on MS now, weekdays, 9 a.m. Eastern. Stephanie, thanks for coming on the press box. Thank you for having me. All right, that's the press box. I'm Brian Curtis.

Who makes it magic? by Isaiah Blakely and John Jones. Coming up tomorrow, Joel Anderson is back and we've got a special guest from the world of politics. Yep, the press box primary rolls on. We'll see you then with more good warm takes about the media. Before you knew what a stock was, you traded snacks, cards, turns.

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