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How to be the Most Interesting Person in the Room?
*In our best Elle Woods impression* what, like it’s hard?
Whether you’re trying to make an impression on a date, in a boardroom, or a networking mixer, there’s one thing that can make you stand out from the crowd…
Asking damn good questions.
But how? Fortunately, our guest Danielle Robay is an expert. With a long history in journalism and hosting TV, Danielle has learned the art of asking good questions.
Danielle also shares her love for pop culture (and a celebrity sighting that Tori simply *cannnot handle*), how she deals with the bullshit of being a woman in media, and how she made herself stand out when she moved to LA.
Danielle Robay is a TV host and journalist, creator of the video podcast PRETTYSMART, and the best selling card game QUESTION EVERYTHING: 52 Cards For Deep(er) Conversation, acclaimed by Forbes as a “game changer”. You’ve seen Danielle on IMDb, NBC, E!, EXTRA, Entertainment Tonight Online, HLN’s Dr. Drew, The Steve Harvey Show and NBC’s 1st Look, and Defy Media where her daily news segments and interviews received over 100 million views a month online. In 2016, she was named co-host of WCIU’s Chicago-based, 2 hour-live morning news program making her the youngest morning TV host in Chicago’s history. With a loyal social media following of over 300,000 followers, she’s chatted with everyone from Taylor Swift + Michael B. Jordan, to Helen Mirren + Tom Hanks. Even Larry King has commented on her compelling interview style: “Danielle has the ability to make people feel seen.”
Welcome back Financial Feminists. Have you ever been in a room with new people or people you really want to impress? Or, maybe you’re out on a date, maybe this is a first date, maybe this is a date with somebody that you’ve known forever, and you’re wondering, “How can I ask better questions?” How can I get past all of the like, “The weather today was beautiful,” kind of bullshit and actually create real connections with people? Today’s guest is here to not only assist you in that vulnerability, but to help you ask better questions so you can not only be the most fascinating person in the room, but also be the most empathetic person in the room.
Danielle Robay is a TV host and journalist, creator of the video podcast PRETTYSMART, and the best selling card game Question Everything, 52 cards for deeper conversation. You probably can’t see me right now, but I have been living in her merch. We had a great conversation and literally I have not taken her sweatshirt off since she gave it to me. I wore it on the plane to get to New York, I’ve worn it two days in a row. This is my second day and I’ve not washed it, and it definitely needs to be washed.
You’ve seen Danielle on IMDb, NBC, E!, EXTRA, Entertainment Tonight Online, HLN’s Dr. Drew, The Steve Harvey Show and NBC’s 1st Look, and Defy Media where her daily news segments and interviews received over 100 million views a month online. In 2016, she was named cohost of WCIU’s Chicago-based 2 hour-live morning news program, making her the youngest morning TV host in Chicago’s history. With a social media following of over 300,000, she’s chatted with everyone from Taylor Swift and Michael B. Jordan, hello, to Helen Mirren and Tom Hanks. Even Larry King commented on her compelling interview style quote, “Danielle has the ability to make people feel seen.”
Danielle is one of those women who just dazzles you with her wit, her intellect, and the way she communicates through thoughtful questions and compelling interviews. We dive into sexism in the entertainment industry, the future of journalism, how she moved to LA and networked with plants. Seriously, if you’re looking for a unique way to get your name out there, this episode’s for you. And, how she asks better questions to forge deeper relationships. I also always joke that I cry in every episode of Financial Feminist, and I cry in this one but for a very, very, different reason. I have a full on meltdown, and I don’t want to spoil it, I have a full on involuntary freak out with Danielle who is a complete stranger to me. Oh, it’s good, it’s a good time. You’re you’re going to want to listen at least for that moment. Without further ado, I think you’re going to love meeting Danielle. Let’s get going.
I’m so excited to have you.
Thanks. I’m so excited to talk with you.
I want to give you right off the bat, what has been your most memorable interviewer conversation? Or give me a couple, and why were they so memorable for you?
The first one that comes to my mind is Simon Cowell because of-
Is he really mean?
He looks really mean.
He’s not, he’s actually the opposite. He’s kind, charming. You could tell he cared about his staff and everybody in the room and was generous with every interviewer, he was one of my very first interviews. I would send people cookies and bamboo plants to try and get jobs because I didn’t know anyone when I moved to LA.
You got to hustle, right? People would email me back and be like, “Hi, Danielle, nice to meet you. We don’t have any positions available, but keep in touch.” I would email them back and say, “No problem, if you ever need anyone last minute, I’m available.”
Smart, so you’re top of mind, right?
Top of mind, I would email every few months. Then one day I got a call at like 3:00 PM and a digital network said, “Our host is sick, can you get to this place in Hollywood by 5:00 PM?” I was like, “Yes.” I go there, it’s the X Factor Red Carpet, and Simon Cowell gave me an exclusive. In turn, I got my first job, they ended up hiring me and I worked for $25 at Red Carpet. But without him and his sort of generosity and having connected with him, I don’t know what would’ve happened.
Walk me through that again. You get the call, hi, I need you to host a Red Carpet?
Have you hosted a Red Carpet before that day?
Probably 10 of them. I had been working for free for this random guy who, I don’t know, was sketchy.
We’re going to table that and we’ll talk about that for a second.
I had done a few. It’s funny because I grew up in Chicago and I look back at those photos and I had no idea how to do my hair and makeup, no idea what to wear. I went in, I was the most confident. I would go to these red carpets and I was like, “I have the best questions.” Looking back, I was standing next to Giuliana Rancic and all these people who had professional help and put themselves together. I think blind naivete is a really beautiful thing.
I love that. I’m a pop culture junkie, this is going to be clear as we move through this interview.
I feel like one of my beefs with interviewers is they ask the same three questions.
It is the most boring thing of all time.
Now as someone who is being asked questions by people, it seems like I get asked the same three to five questions.
What do you get asked?
You’re making notes for [inaudible 00:06:06] how do I not ask?
Tori‘s about to be on my pocket.
You’re very subtle. No, I feel like it’s like, what is financial feminism? Tell me about your money story? We were talking about this earlier, but very similar, like why aren’t women saving as much money, or why aren’t women doing this? It’s very … yeah.
It’s hard because on one hand you have to reintroduce yourself to everyone you speak to.
On the other hand, yeah, I’m with you. I also think there’s different ways to ask questions.
Tell me more about that?
If I were to ask you about your story, I think a lot of people set up questions saying … They don’t ask specifics, I think is what I’m getting at, so they’ll say, “Tell me your story?” It’s like, that’s overwhelming.
Also it’s a job interview question and it’s the worst question.
But it overwhelms your brain?
Yeah, you’re like, where do you … my personal story, my dating history, my medical chart? What do you want? I don’t know what you want.
Yeah, that’s true. But I think it overwhelms you, you don’t know where to start. If you get more specific and say, Tori, where did you grow up? Then, what’s your favorite thing about your mom that you really love about yourself that she passed on to you? What’s your first memory with money?
I love that one. There’s a whole episode about that one.
There’s just specifics that can give you the same information.
That said, red carpets are a whole different animal because you’re just trying to get soundbites, but I don’t do them really anymore.
The goal for red carpets is not … obviously, it’s not a let’s sit down and have a authentic conversation about your performance in this movie. It’s for soundbites, that’s your motivation there?
Even if it is tell me about this movie, it’s for a soundbite. I worked for IMDb, which is an awesome … It’s for cinephiles. They don’t want me to ask about your divorce. Thank God. But I still have to get soundbites about the Batman movie and things that will do well online because that’s how the media beast is run.
I’m that person that sits on IMDb while I’m watching a movie if I’m at home.
Yeah, on trivia.
You’re a nerd.
I know. For favorite movies …
I love it. I’m a nerd too.
I have so many favorite movies where my favorite person in my life will watch them with me for the first time and I’m like, you know the scene in Oceans Eleven where Brad Pitt is eating a shrimp cocktail, he ate that shrimp cocktail for 10 hours. That’s my fucking show, because it was an all day shoot.
He must have been so sick.
He ate like 20. Well, the joke is an Ocean’s Eleven is that his character, Rusty, it’s one of my favorite movies, he’s-
He’s always eating.
He’s always eating.
But it’s the Vince Vaughn thing. Vince Vaughn, any movie he’s ever in is always eating. That’s like his comedy, is eating.
Yes. Yeah, always eating. In terms of asking questions, you’ve said that asking good questions is a superpower.
How can we as non journalists take good questions and make them applicable to our own lives?
That’s such a good question. I’m going to ask you a question before I give you an answer.
Danielle strong> (00:09:16):
What do you think the number one complaint is after any first meeting, first interview, first date, first job interview?
Complaint, I’m being interviewed and I’m complaining?
Yeah, or you go on a date.
I didn’t get enough questions about myself. Or, they did all the talking, they didn’t ask me any questions about myself.
It’s exactly it. Personally and professionally, the Harvard Business Review did a study, the number one complaint is I wish they had asked me more questions.
Interesting. A lot of people go into these situations very nervous too, so it’s interesting where they’re like you could go in nervous to a date or a job interview and then leave going, but I wanted to talk more or I wanted to explain more. That’s an interesting dichotomy.
I think people just want to feel seen. Oprah has this great anecdote that at the end of every interview, even Obama, will turn to her, the cameras turn off and they go to commercial break and every single person says, “Was that okay?” We just want to know that we’re okay, seen, heard, validated. I actually think questions should be added as a love language because I think they really make you feel cared for. You’re saying to me I would rather be in conversation with you here, present, spending time with you doing this more than I would rather be doing anything else. I know I’m like dork, I have chills.
No, me too. I literally have goosebumps.
I think, what’s more loving than that? I’ll give you a small anecdote of how I discovered the power of questions, because I actually didn’t always feel this way or know about it. But I got what I thought was my dream job, an entertainment outlet hired me, I was the youngest person they ever hired. I walked in, I was like, “Yeah, this is why I moved to LA.” I was all ego, this is what all the sacrifice was for. I did it, hell yeah. I got there, I hated the job. I would break out into hives, cried in the bathroom at lunch. One of my old bosses called it the “oh shit” job, I hadn’t heard that before.
I haven’t heard that either, but it makes sense.
I think a lot of people have the “oh shit” job.
Right. Where you thought you wanted something, got into it and you’re like …
Yeah, and you think it’s going to be one thing and it turns out not to be. I ended up quitting and I was living off my credit cards. Don’t tell Tori that.
Nope. What? Sorry, I just blacked out for five seconds.
To, I think, a lot of your points that I’ve listened to in your interviews, not feeling in control of your money is incredibly anxiety ridden, so I was full of anxiety because of that and I was like, “I better make use of this time.” So I took myself to grad school, I watched hundreds of hours of Robin Roberts, Larry King, Katie Couric, I wanted to try and be the best. I looked at this Google doc that I had written, I’d interviewed athletes, celebrities, politicians, thought leaders, entrepreneurs, and I had a list of about 800 questions. I thought, “I ask questions for a living and I’ve never asked myself one.” This was pre therapy. I started asking myself about five or six questions a day, and by the end-
Are you journaling or are you just thinking about it? What is your process for that?
I love that you asked that, no one’s ever asked me that. I would do it before I went to bed and I would think about it. In hindsight, I think journaling is actually probably more efficient.
Well, and it’s also, for me, what I’ve realized about journaling is it’s the reflection in the moment versus the … One, it’s cool because you get to reflect on it later, you get to in a year be like, “Oh I was in that spot.” But it’s also the act of literally ignoring that future you is going to read this and instead writing something that present you needs to get out. It’s very therapeutic in that way.
It is. I agree with you, I started doing it more recently.
I’m a big journaler now because it was just very therapeutic. But anyway, you were asking six to seven questions a night?
Yes, and by the end I was more interesting at dinners, more practice at asking questions, I actually felt more confident in myself. But the main thing that changed was, to be perfectly honest, strangers were magnetic to me. My relationships that I had that really mattered to me like my friends and my family, I could tell that they felt closer to me.
Because you had done work on yourself.
And I started asking them these questions, because they were top of mind for me. I was like this really is a superpower. All jokes and hyperbole aside, it’s a magnet for people and anybody can tap into it. That’s why I launched this card deck, Question Everything, because I believe that everyone can tap into the power of questions. It’s incredible.
I’m sure you know about it, the 36 questions that lead to love.
Yes. Yeah, the New York Times ones.
Obsessed with those, have done them literally-
On a date?
I’ve started seeing somebody.
It’s still very early, it’s casual and nothing’s happening yet. But it’s like first date, first date-
Because I’m done with the questions of siblings, this, that. It like you just get into it.
All those are helpful, but I know for a fact within probably a half hour of meeting somebody if that person’s going to be even down to do it or not. That honestly tells me everything I need to know, of is this person interested and let’s crack this shit open. Let’s start getting vulnerable immediately. You pass the first six dates and you’re on date 7, 8, 9, just because you’re … I do these with friends, I’ve done these with a lot of people I love in my life regardless of my romantic connection to them, of just let’s talk about some serious shit. If your house is on fire and you save, what is it, your family members and your pets, what one item are you saving?
They’re even fun ones. One of the questions in my deck is do plants thrive or die in your care?
Thrive. They thrive.
See, they die in my-
They did not for a while because a good friend of mine told me that the number one rule of plant parenting is to leave them the fuck alone. That’s his quote, is you leave them the fuck alone. Because I would over love them and then it was like, no, leave them be, they’ll tell you when they need water. Because most plants don’t die from underwater, they die from overwater.
That’s how I killed my succulents.
Succulents need nothing. Leave them.
Yeah, still do that one.
I’ve killed so many plants before I got them right. When I had my apartment, 45 plants in my tiny little one-bedroom apartment.
Oh my God, 45. I have four fake ones now.
No they’re good. It’s fun, it’s fun for me and it was a good transition into learning how to take care of something. You touched on this before, talk to me about some of those early years in Hollywood? The hustling, the trying to break into this really notoriously difficult industry, and what initially drew you to journalism?
I went to college at the University of Wisconsin, Madison, and I was a political science major. I loved it because I think it taught me how to think, not what to think.
That’s a beautiful statement. How to think, not what to … No, that’s very poetic. That’s very thoughtful. Yep.
It’s really how I felt. I think it informed a lot of the way I view pop culture now. I had done theater growing up and my mom said to me … Really?
Oh yeah, I’m a theater major.
I always get along with theater kids, and camp people.
Kristin’s over here too. Kristin’s our podcast producer over here just pumping her fist.
I think people do not give theater majors enough credit.
Thank you. I’m pulling away from the mic so I can scream. Thank you.
It’s incredible training in so many ways.
Yes, think on your feet, team player, good communicator, good storyteller. People are shocked initially when they’re like, “You’re a financial expert and you’re a theater” … I’m like, “Yeah, 100%.”
Because life is a little bit of a performance, even if you want to be completely authentic and sincere.
Yep, had a whole conversation with another guest about that last week. Yes.
Yeah, I’m with you. I took a lot of theater classes in college too, I love it. But my mom said to me, to her credit, she was like, “I wonder if you would like news? It combines your love of being on camera and also politics and news.” I was like, “Okay, I’ll try it.” I lied because you couldn’t get an internship unless you were a junior, and so I made a resume that said I was a junior and applied to a bunch of news stations in Madison and I got an internship. I would bus three times a week to the Fox station and later the NBC station there, and I fell in love the first day, I have never turned back.
I loved it, I loved the storytelling. I always tell college kids there’s something that I wish people told me which is if you don’t know what to do or you don’t know what you’re going to like, think about the people you want to be around. Think about yourself at a dinner with a bunch of influencers, are those your people? If so, go try and be an influencer. Do you want to be with a bunch of accountants? Those are your people. When I’m in a newsroom, those are my people.
That’s amazing. For you getting started in journalism, much like myself now in the financial industry, I feel like … Well, journalism there’s probably more women, but do you feel like there’s not women at the top as much? Because I feel that way a little bit about finance, one, there’s not very many women at all. Two, very few women make it to the top of the traditional finance structure. Then there’s unfortunately more and more now, but very few of us actually like getting the opportunities to talk about money.
I don’t want to misquote the exact percentage, I used to know it.
We can pull the stat too.
A significant portion, I want to say it’s 60% or 70% of GMs, General Managers and news directors are men. Those are the people at the top of the food chain, the executives. While there are plenty of female journalists, there’s actually not a lot of female executives in TV news or in written journalism. I do think having worked in all different parts of TV and news that who you have in your newsroom informs the content. That’s why it’s so important to have diversity of race, gender, ethnicity, thought, IQ, experience, all of it, because you’re telling better and more diverse stories. There’s a big issue there. There’s also some sort of gap that happens between journalism school and actually getting a job. I think there are 50 something percent of journalism students are women, but then only 40% or 30%, I have to get the exact stats, there’s a gap.
So 10%, 20% fall off or don’t get an opportunity.
Yeah, there’s a gap between school and being hired.
I feel like from my understanding of journalism, especially broadcast journalism. We know this from … What was the Margot Robbie movie? Was it Bombshell, is that what it was?
Is it the one with Tina Faye?
No, the one … Charlize Theron.
It’s so good.
It felt like, and I would love your thoughts about if you still feel it’s this way. That if you are a woman or a female identifying person on camera, you don’t just have to be good at your job, you have to be stereotypically attractive.
And that if you are not stereotypically attractive, that might mean less opportunities for you.
Do you feel like that’s still applicable now?
I think it’s gotten a little bit better because our idea of what is beautiful has expanded somewhat, but yes, that is very much the case.
Especially if you have men who are making those decisions.
Exactly. There’s also an element of pressure once you’re in it too because-
Right. It’s not just when you get the job, it’s the continuation to be stereotypically attractive, skinny, made up all the time.
I did a morning show in Chicago, I had to wake up at 2:45 every morning.
What time were you in bed?
Like 7:00, it was weird. But my male co-host got to wake up at 4:45 because I had to do hair and makeup. Those two hours, sleep, study, get better at my job, all those things and there’s literally no choice. I had to wear heels, it was in my contract
And the cost, financial, of all those things.
Yeah, it’s huge.
I just wrote a section in my book talking about all of the things that had to go into the cover shoot. That men get to show up and maybe they have suit and tie and maybe they get a haircut.
I call it invisible hours.
Yep. It’s the financial cost, it’s the hours. It’s the time, it’s the energy, it’s all of it. No, you’re so right. I want to talk to you about my least favorite question on the red carpet ever.
I can guess.
What is it?
Something about who are you wearing?
Thank you. Yeah.
I’ve never asked that once.
It is horrible.
Talk to me, tell me why that question is bullshit?
Well, the question is bullshit for a few reasons. One, it’s because why would you … regardless of what the question is, why would you want to ask what everybody else is asking? Two, it’s historically been gendered, so now at least people are asking the men what they’re wearing. What I’ve learned that made me hate that question a little less is that the fashion industry really depends on celebrities wearing their clothes.
When I did my research around this too, I guess it started in the 90s. Joan Rivers actually was supposedly the first person to ask it, and it was because, especially back then, nobody knew designers. If you were going to tailor make an Oscar dress for a celebrity or for an actor or an actress, really, it was their salute, or thank you, or shout out because the fashion industry or the designer would not have gotten it otherwise.
Exactly. For that, I think fine, but isn’t that what Instagram’s for? Tag the designer, shout them out. To me, the red carpet reporters don’t need to be asking that. Historically, they were only asking women and so men were being able … were talking about their movies and their films and women were talking about their clothes.
I’m trying to remember who did it, there was a push, a very public push to stop asking that question.
If I remember correctly, it started with the MeToo movement and Time’s Up.
Natalie Portman was one of the people, I think, with Time’s Up. She was very [inaudible 00:24:51].
I think the Golden Globes they all wore black. Then it was because don’t ask me what I’m wearing, ask me about Time’s Up.
Right. Cool. I’m like, is that sustainable?
I think people are changing. I think young reporters, even though the people in charge are still a bit of a different generation, I think young reporters … When I speak to Gen Z, they change everything, they’re so cool.
Almost half of our team at Her First $100K is under the age of 23, 24.
You’re so lucky.
It’s so funny because I was so used to being the youngest person in the room, and I’m 27 so I’m still pretty young. But it’s been so funny because I’m saying the shit that people used to say about me and I hated it every time it would happen. Now I’m saying this, it feels so old. I’m like, “Why am I doing the shit now that I used to hate?”
I used to hate when people would do that to me.
Oprah always says for her whole life she wants to be both a student and a teacher, and I think about that too. Because with your team, you’re probably learning from them and teaching them.
100% learn something new from them all the time. You had mentioned already this I am going to be the squeaky wheel that gets the grease, and we’re alike in that way. Politely, but I will be the squeaky wheel until you give me some grease. At the same time we hear the word network a lot and we’re like, what the fuck does that mean? It’s very much a buzzword that I don’t know how many people can actually define. Can you define it for us, and what strategies do you either recommend or what stories, things that you did that ended up furthering your career?
I actually love talking about this because I think people … the way I hear it spoken about is so unhelpful. To me, sales is not about selling, it’s about helping people. I feel the same with networking, it’s not about what you can get, it’s about what you can give. And so, when you walk into a meeting or any room, the first thing I think about no matter who I’m meeting is I wonder how I can help them, and it’s coming from a sincere place.
One, it gives me pleasure and joy and it’s fun to be the first mover, but also that’s how you connect with people. That’s how you learn more about them, they’ll start asking questions. They’re going to care about you because they feel cared about. And so, if you walk into a meeting and you see somebody has a kid wearing a baseball uniform, oh, is that your son or who is that? Do you love baseball? Just ask questions instead of going in thinking I have to impress them, I have to tell them about myself, I have to sell this.
It’s very formal and structured.
You’re never going to win that way.
No, it’s a conversation.
That’s what we’re taught, I was taught that.
I was too. I always think of the pencil skirt, not physical, although sometimes I did wear pencil skirts. But it was that kind of energy of button up, play by the rules, you send a message on LinkedIn.
Yeah, and everybody’s human. I think if you think about how you can help them, not to belabor the point, but ask a great question that means something, you’re going to form a relationship and make a moment with them versus trying to get something. I had somebody who over time I think maybe became my mentor, it was never official but-
These things never are. They’re never like, “You are now my mentee.”
Right. That’s funny.
I would email him articles I read that I thought would be interesting to him about TV news or about something we had spoken about. And so, our relationship became beneficial to both of us instead of just me.
Which literally my next question was one of the things I hear from people early in their career or students they’re like, “How can I help this person?” That’s literally something I recommend and something I did of, oh, hey, I know the informational interview I asked you for, which we sat down for a half hour and you were kind enough to answer some questions I had about your career. I remember you talked about, I don’t know, your love of the Pittsburgh Steelers, and hey, did you see that they just traded this part? It’s great.
I’ve had probably 100 phone calls with young women, two young men, over the course of my career at this point, maybe more.
Who are coming to you to ask questions?
Yes. One person sent me a thank you.
I’m not upset about it, because to each their own. But I think a thank you note, oh my God, goes such a long way. Even a thank you email.
In 2022, I could not agree more. I did an informational interview every single week of my senior year of college. Even if it was the middle of finals I was like, “Thank you for taking time, I really appreciate it.” I probably attached my resume and I was like, “Let me know if there’s anything I can do or any opportunities for me.” Oh man, really?
Yeah. I think just little things really go a long way.
I’m not surprised that a good chunk of them didn’t but only one out of … Wow.
Yeah. I know.
I have to sit with that for a bit, I’m shocked. I also grew up in a household where my mom was like, you were writing a thank you note for anything.
Yeah, it’s nice.
You wrote a thank you note for a thank you note, I’m like …
Yeah, that’s my grandmother.
My mom was like, “I don’t care, you get a $10 check, you’re writing a thank you note.” I’m like, “All right.”
That’s nice. It’s good practice.
Yeah, I know.
Write a thank you note, guys. Oh man. We talked a bit briefly about this … not only the pay inequity in journalism, but just the lack of opportunities. Have you been in workplaces where you knew for a fact that you were paid less?
I quit my job because of it.
We might have known that when we were settling down for questions, but talk to me a bit about that experience? Were you able to advocate for yourself, how did you even discover you were not being paid and compensated fairly? Because I feel, again, common question for me is it’s I just discovered, or I have an inkling that Chad is making more money but he has been here two years less than I have. Talk to me.
I actually don’t know if I handled any of this right, I think about it all the time. Use this story as a teachable.
[inaudible 00:31:35] here it’s beautiful even if I don’t know if any of this is correct. It’s great to talk about and I appreciate you being vulnerable of like maybe I didn’t do correctly.
Well, I think we all have to talk about it so we can learn from each other’s mistakes. I was living in LA off my credit cards.
Blacked out for five seconds.
Yes. I get this job opportunity in Chicago to host a morning show. I had fallen in love for the first time and so I did not want to move because I was like, “I’m in love.”
You were in LA, you got an opportunity in Chicago and you’re like, “I don’t want to leave.”
I don’t want to leave, I’m in love. It took me years to set my life up in LA and I had a woman that I really admire call me and say, A, if he’s the right guy he’ll be the right guy in two years. He was not the right guy.
We always find it out, don’t we?
We find out. And B, if you can cover a funeral of a mayor in Chicago, you can cover Michael Jackson’s funeral, go take this job and get the practice that you need. She was right on both accounts.
Did it feel like a step back for you because you were in Chicago and then moved to LA, right? Or, you were in Wisconsin?
I grew up in Chicago.
Okay. Got it.
Went to Wisconsin for school, moved to LA, lived in a garage, and then ended up moving back to Chicago for this job.
Got it. Did it feel a bit like a step backward?
I don’t know, I think I was excited about the opportunity but it was scary to leave LA. Would I ever come back, and I took this big risk to move there.
Well, LA I feel like is bigger than the city, it’s like the promise of what a Los Angeles is, right?
Yes, that is a great point. I went to the gym this morning and met Childish Gambino, AKA Donald Glover.
That doesn’t happen not in LA.
No, you did not.
Do you love him? Oh my God. Tori, you’re having an actual meltdown, this isn’t an acting … Are you crying?
I was listening to him on the [inaudible 00:33:38]. Was he nice?
The kindest. I can’t believe you’re actually crying. Are you this good of an actress or are you for real?
No, I’m actually crying [inaudible 00:33:56].
This is incredible, now I’m sweating.
I’m sorry, we have to pause, tell me everything. He was at the gym, what gym? I’ll show up tomorrow, what gym?
It’s a small training gym so he was about to work out with a trainer.
Did he have the beard, how long was his hair?
His shaved head, have the beard. So present, kind, asked questions.
Of course, he was. Great.
Beyond lovely spirit, wonderful.
you go up to him, did you talk to him?
It was like a 30-second interaction, maybe a minute.
Yeah, but you were like hello?
What did you say, what did he say?
We talked about Chicago and Atlanta, so I said, do people feel like it’s a love letter to the city? We were just talking about cities and where you [inaudible 00:34:45].
Because of course you’re an interviewer, you’re like let me drop some great … boom.
Yeah, so anyway.
I don’t even remember what we were talking about, I need a second.
I need water.
No, please take one.
How funny, because it could have been anybody [inaudible 00:35:00].
I literally was rapping Sunrise before I walked in here.
Why do you love him so much?
It’s really interesting because there’s still a lot … I’ll be honest with you, I’ve only seen an episode of Atlanta. But I got really into Community during quarantine.
He was great in that.
Also got really into his music. 3005 was my most played song of last year and it got me through some shit, I don’t even know why because that song’s just a bop.
One of my favorite, this is a whole deep dive, one of my favorite things about art or one of my favorite kinds of art is art that is just entertainment. But that if you want to strip it back, you can. The Great Gatsby is my favorite book because if you just read Great Gatsby, it’s an entertaining book where it’s got murder, and it’s got lust, and intrigue, and …
Yeah, and people growing up together and leaving and then coming back, and fashion and all these things. Parties, but then of course you can do the English class shit of what is the green light symbolize? What is the clock on Gat
sby’s mantle? All of that shit. I feel like he does a beautiful job of making music that is so infectious and so fun, and then if you want you can strip it really back. 3005, even that, the title is supposed to be symbolic of the infinity symbol. Usually you have three and five and if you were to close the loops on those, it becomes the infinity symbol, because he talks about be right by your side until 3005. It’s just so smart, and that’s my favorite art or entertainment where you can just do surface level and it fucking slaps, or you can do more intentional deep dive stuff and it’s still so good. I’m so excited.
That was awesome.
That’s so cool, man.
I’m so glad we brought that up.
I usually never drop those types of things. That was great.
I’m still like, okay.
It’s so good.
That’s so fun. I don’t even remember what we were talking about.
What was I talking about?
I don’t know.
The promise of LA.
Yes, LA does have a thing.
Yeah. It’s more than just I’m moving to a new city, it’s like, I’ve made it.
Yep. I move to Chicago, I take this morning show job. The male co-host that they hired we had tested together so we had each other’s cell phone numbers and were friendly.
It’s never occurred to me that you have to test with your co-host. I don’t know why I didn’t think about, that’s very like theater.
You have to test with your co-host. That’s so interesting.
You audition, because there’s a chemistry test.
That’s so obvious but I don’t know why I didn’t take … Yeah, because sometimes you’re right for the role but you don’t test well with this other person.
Danielle strong> (00:37:59):
Or they’re right but you don’t test well with … or whatever?
Interesting. I didn’t even think about that, but that’s so obvious.
Yeah. We were chatting during this whole process and he told me what he was getting and I told him what I was getting, and so I went into negotiations knowing that what they offered me was so much less. Then when we tried to push for more, it was like take it or leave it. I had a long conversation not just with myself, but with other people because I thought, okay … I think I was making $105,000, and he told me he was making $170,000.
Oh, so it’s not …
It was a third, if not more.
105 to 170, so it wasn’t like $5.000 or $10,000, it was …
No, it was significant.
Oh my God.
I think it’s important to be pragmatic about these things too, I don’t think it’s fair to not assess other variables. For instance, does he have more followers? No. Does he have more years of experience? No. What are you bringing to the table? Because those do matter.
Does he have a master’s degree and I don’t?
Exactly. That matters, I don’t think it’s fair when people don’t take those things into account regardless of gender. It ruins our argument as women, to be honest.
The only thing he did have was he was a few years older than me, but he had started later in broadcast because he was an athlete at one point and so we did have commensurate experience in years. I went into it knowing that, but I also said to myself, “Is that $65,000 going to change my life?” It would help a whole hell of a lot. It was difficult in Chicago to pay my rent and do all the things I needed to do, as crazy as that sounds, but it really was, and be comfortable. So yes, it would’ve enhanced my life. Was it going to change my life? No, and I wanted the experience. I wanted to get better.
Which it’s not your fault, but that fucking sucks.
Because it’s also, I don’t want to go on a whole rant about it, but it’s also not just you losing out on 70K now.
It’s the opportunity to make-
Compound interest, all of that.
All of it. Yeah, it sucks.
Oh man, I’m sorry.
Thank you. There’s no silver lining, it sucked. Found that out and then when Catt Sadler quit, I reported on that live and I remember my eyes welling up. I watched the clip back and if you know me well, you can see it, if you don’t, you can’t really tell. Because I was sitting thinking to myself, “I’m the Catt, I feel like such a fraud right now reporting on this.”
Eventually my contract was up and my boss at the time, I think, offered me like a 3% or 5% raise. I didn’t even go into it because I realized that they were never going to see my value, and so they were using me and I needed to use them for what I needed. I had done that, so my time was up and I left. Honestly, the show eventually got canceled. I don’t know what would’ve happened had I stayed, but we had nice chemistry. I don’t know, I think it was there loss, honestly. I was a really good employee, I wrote, produced, I worked really hard.
100%. I’m sorry that happened, unfortunately, I think that’s all too common.
It’s the story of so many women and it’s getting better because we’re talking about it and getting better because we’re helping each other, but it’s still not quite there.
Well, that’s why my big thing is we need to just talk about money more. This whole talking about money narrative it’s ridiculous, it’s perpetuated by the patriarchy to keep us quiet.
Don’t you think it’s interesting that we talk about sex way more comfortably?
We literally have that on one of our episodes. We’ll talk about sex, we’ll talk about politics, religion, death, any other uncomfortable topic before we’ll talk about money.
Yep. It’s so interesting it’s so taboo.
We’ll literally … I was about to say be penetrated by somebody, but literally we’ll be naked with somebody a million times before we’ll have a conversation with them about money.
Yeah, it’s the number one thing couples fight about too.
Number one reason for divorce as well.
Yeah, money. I still, Gambino, I can’t get over that. I’m trying to keep it together.
You got it, girl.
Again, briefly discussed this in terms of what you said, invisible time. What burdens do you think women experience that men just don’t in the way we have to present ourselves in the workplace?
How much time do we have? My podcast is called Pretty Smart and it’s literally stems from this. I read a book called Beauty Sick and Dr. Renee Engeln is the author, she’s a professor of psychology at Northwestern. The book opens and says 54% of women would rather be hit by a truck than considered fat. When I read that-
One more time.
54% of women would rather be hit by a truck than considered fat.
Considered fat by whom, do we know? Society, men, I’m assuming, themselves?
Great follow up though. When I read that, my heart sunk because in high school I would’ve for sure said hit by a car. Or I would’ve been like, how fast is the car going, or is it a truck or a Prius?
Have you watched Fleabag? Have you ever seen Fleabag?
Yeah, I love Phoebe Waller-Bridge.
They’re like, what is it worth? She’s like I’ll gladly take a year off your life to be, what is it, 10 pounds? Both of them were like, yes, then they realize no one else is raising their hands.
Yeah, it’s that?
It’s also extremely fat phobic, which I think is very [inaudible 00:44:02] to highlight.
Horrible. But also I think in the time that we were growing up, I didn’t even know any of those words. Fat phobic wasn’t even a word when I was in high school. Paris Hilton was the thing, and now we know that all the people that we were looking at in magazines for the most part have come out and said they have eating disorders, issues with drugs. All those things were not attainable.
Also money with which to invest in chefs, and trainers, and drivers, and all of these things to make them make … make up artists, Botox, all of these things.
Yeah. But the book, Beauty Sick, if anybody’s more interested in this topic is life changing. But yes, the podcast is based on that because I’ve also experienced it in my career. It’s definitely amplified the amount of hours, and time, and money and just focus that I have to spend on clothing and having the perfect shoes. I realized that I didn’t like packing for trips, I wo
uld get anxiety for trips when most men would be excited to go on vacation. Most women can’t pack, they freak out. Almost all of my friends, my mom, I had this at one point, I’ve since fixed it, because you have to have the perfect outfit. You have to have the right outfit for the beach, and then the right outfit for dinner, and the right outfit for this. It’s with Instagram, that’s amplified.
Well, and you can’t because, God forbid, you repeat an outfit.
Which is such bullshit for so many reasons.
But if you let go of that, your life is so much better.
Totally, but also society refuses to allow us to let that go.
Right, it’s our currency.
Right. Because if I show up at work, if I were to show up at this interview non made up, I would get comments that would say, “She looks tired. She looks unprofessional.” It’s the double standard of the very thing that we get shamed for as women, which is you spend too much time on your hair, you spend too much time on your makeup, is the then thing-
It’s so interesting.
… the thing that then is a double standard.
I saw a video online the other day, an outlet I used to work for did so I follow them still even though I normally wouldn’t follow them. They did a three minute video on if Kendall Jenner had gotten lip filler or not because people online recently thought she did. I was about 30 seconds into the video thinking to myself, I’ve never seen a video similar to this about a man questioning if he had surgery or not. The idea of whether she did or not, who the F cares? Also, the fact that we’re talking about it is making whoever’s watching this think, do I need lip filler?
I literally talked about this with Victoria last week so it’s so funny. We were picking on the Kardashians a little bit, because they’re an easy target, unfortunately. But I do think one of the issues, though, with celebrity, with fame, with being professionally hot, is that people who are professionally hot very rarely actually discuss what went into them becoming professionally hot.
But there’s so much misogynism built into that.
Totally, I completely agree. However, if I’m a young girl, if I’m me looking at Kendall Jenner going like, “Oh my God, she’s so beautiful,” and I’m thinking that’s attainable. I agree with you 100% on your three points you just made, I also think there is a potential where I’m watching that video and going, “Oh, so it isn’t obtainable,” and that comforts me in a weird way.
Yeah, totally. I agree there should be transparency, but we don’t have the same obsession with men’s appearance. We have obsession with their money, which is also not fair. That’s a lot of pressure for them, it’s not fair. I think if we’re stripping away gender issues for women, we should strip them for men too.
Yeah, masculinity and undefining masculinity affects men as much as it affects women.
When you look at money magazines, I actually did this in Chicago. I held up all the most famous magazines of men on t
he cover and women, the women were almost all in bikinis or really skimpy clothes.
Sometimes even naked.
Yeah. The men were all in suits looking really dapper with a briefcase like it was about power versus sex.
They’re crossing their arms or it’s … Yeah, totally.
I think it like shows our value system so blatantly.
We’re okay with men having money and we applaud men who have money, but when women have the audacity to say, yes, I would like to be rich, I would like money, we shame her.
Yeah. Oh God, yeah.
I feel like we don’t. Like Bethany money, Sarah Blakely, or Hugo.
Well I believe Bethany, is Bethany a white woman? Both of them are white women, so that’s one thing.
Sure. I think what happens, though, is either women who have money become caricatures, real housewives, they become caricatures of women who have money where they’re catty, and they’re yelling at each other, and they’re having frivolous Beverly Hills lunches where they scream. Or what happens, which is what I’ve experienced, is this double standard of altruism.
The idea you can’t negotiate for yourself but you can negotiate for your team.
Yes. Or, I can’t want money just because it makes my life better, I have to want money for a higher purpose. Now, I want to be clear, donating, 100%. That’s what financial feminism is to me, is it’s get your own shit together so that you can help others. Get your own financial foundation and bring everybody else along for the ride, I 100% believe that. I think donating, especially if you’ve built some sort of wealth is extremely important and something that I 100% do. That being said, we do not have that same expectation for men. My TikTok comments, every time I talk about money or me building wealth is immediately like, “Yeah, but what are you donating?” Immediately, and I’m not seeing this for men.
I agree with that point.
We weaponize women’s altruism, which is a beautiful trait that I think a lot of … we’re conditioned to have as women, but then we weaponize it. So we’re like, okay, we’re only okay with you having money as long as you do something good with it. Or, we’re only okay with you being a CEO as long as your company does something.
Do you think that the media women consume is belittled?
What an interesting question?
What media are women consuming?
When I wrote this question, when we wrote this question, it was more I think … You’ve talked about how pop culture is a currency, or having the knowledge of that. But yet I feel like that is not as impressive or that is … you’re almost demeaned if you have. If you can answer all of the jeopardy questions about The Bachelor, but you can’t answer all the questions about the capitals of the world.
That’s funny. I don’t know if I would put those on the same playing field. I know what you’re saying, but if we’re being stereotypical about what men and women are watching, which I think we have to be for a minute. It’s like video games versus pop culture.
Or sports versus-
Sports is a great one. Sports versus The Bachelor is a great example.
Again, we’re being very stereotypical, we are playing into very stereotypical gender roles for this thought experiment.
Totally, yeah. I love that you’re into sociopolitical stuff, this is fun for me to do with you. I do think it’s belittled in that sense, like sports is thought of as having more gravitas. It’s okay to be really into sports, it’s okay to bet on sports.
It’s okay to cry when your football team loses.
It’s the only “acceptable”, I’m putting acceptable in quotes, time for men to cry is when your team loses and when your dad dies. it
Oh my God.
It’s the two times.
Yeah, just watch the movie Rudy and you’re good.
Tin Cup, my dad every time will cry, every time.
I agree. But at the same time, if I’m being fully honest, I think The Bachelor’s so stupid and I don’t think sports are stupid. From a personal perspective-
I think Bachelor’s stupid as well. But my best friend who’s my favorite person in the entire world loves The Bachelor.
Yeah, so do a lot of my friends and we fight about it. Because I’m like, you’re playing into all of this stuff that’s so bad for women in our society. They’re like, “I work 50 hours a week, I’m tired.” I’m like, “Okay, fine. You’re right. Enjoy.”
forgot I used to do this until just now, I worked at a hardware store, it was my summer job in college. If I didn’t have a customer I’d be sitting reading the news because that was the only thing you could do. You could be on social media, but I’m like, okay, I can read the news. I’d go to Google News and I’d read the headlines and then I would scroll until I got to pop culture. I didn’t read politics, I didn’t read anything. I was 19 and I was like, I just want to know what movies are being made, who’s talking to who, who’s dating who? I feel like that is largely read by women, one. And two-
I don’t know, The Shade Room now, I think they have a very male audience.
Do you think so?
Okay. I might be wrong, maybe it’s changing. Do you feel like it is, do you feel like it’s transitioning? Because I feel like your knowledge of these things, if I bring out a cocktail party has more stereotype … I guess, thoughtful people who are more academic, my knowledge of, I’m trying to think, again, Community. Or my knowledge of, I don’t know, who won the Best Picture Oscar for the last 20 years is less quote unquote “impressive” than the more academic perspective.
You’re right. I used to have a big insecurity about that when I did entertainment news because I was-
That’s what I mean. Maybe it’s not a legit a journalist if you’re not doing the hardcore like you’re reporting on wars and you’re … I don’t know.
But I then did pieces on gun violence for Planned Parenthood and I realized it was harder to put those pieces together, I did have to do more research and learn more. There is a difference and that’s okay, it’s okay to be into frivolous stuff. If we’re calling sports and entertainment frivolous.
Well, we’re putting frivolous in quotes.
But yes, I actually just had a job interview for a serious network and the guy called me a red carpet girl.
Which girl, first of all you’re not a girl, you’re a goddamn woman. Jesus Christ, I hate it when they do that.
For sure. That felt demeaning.
Yeah, because red carpets are what, I don’t know. Would you say that if I was on the sidelines at a football stadium, which I have been? Right. I don’t know. There’s definitely a pieces of that, for sure.
Or even beyond football, but are you saying that if I’m in war torn Syria-
Then he’s definitely not saying that, but also that’s harder.
No, sure. 100% sure. Talking to Leonardo DiCaprio is slightly easier than fearing for your safety every moment.
No, that’s valid. That’s valid. What do you hope for the future of journalism?
Oh man, this question is really meaningful to me because I believe in our democracy, I’m a real patriot. I always have been, the card deck I made is made in America even though it costs 10 times more, it was really important to me. I believe in the power of the press, I wouldn’t be a journalist if I didn’t believe in it and I have worked alongside some incredibly talented people. Journalists don’t make a lot of money, for the most part, and they spend so much time at their job.
If we broke down how many hours we work versus what we’re … the actual pay is not very high. These people not just love what they do, but also do it as a public service in a lot of ways, specifically local journalists. The issue with journalism and fake news is money. It is the system behind news, the system behind media that makes media run. And so, my hope is that somehow we can figure out how to fix how money and media coexist. I don’t know how to do it, it is the ad revenue that is the issue.
Right. Well, and so much of media is owned by people who have billions of dollars and who are actively swaying elections with those billions of dollars. And are not just of course donating to these campaigns, but are using their media outlets to continue pushing an agenda.
There’s so many great examples of this, but I think Trump having been so bombastic during his campaign in 2016, I forgot the exact … I don’t have any exact statistics clearly on this podcast. The stat was the amount of media coverage he received by being bombastic equated to hundreds of millions of dollars. He just did that, the press played into it.
Because it felt like a reality show because that’s what he did for, what, 15 years was host reality shows. And so when he said something crazy, especially under the guise of this is a race for the presidency, which it was supposed to be at a level of decorum. And so, he would say crazy shit and we would all lose our goddamn minds over it.
But the press played into it.
They played into it because it got clicks because it got clicks and eyeballs. And so, how do we separate those things? I don’t know.
Well, it’s the conversation about how do you separate money and politics? They’re so interwoven.
That’s also the fundamental issue with politics. Democracy’s actually amazing, it’s just how do you take overspending? How do we give regular people a chance to become politicians?
Well, and how do you allow regular people and their vote and what they believe to actually have a sway as opposed to, again, these billionaires who can just go in and dump a bunch of money?
But that’s where you come in, we got to figure out the money piece.
I’m trying, I’m trying slowly but surely. Thanks for being here. I appreciate it.
You’re such a great interviewer.
Thank you. That’s so kind. Where can people find out more about you?
At Danielle Robay, R-O-B-A-Y on everything. The Question Everything card deck is on my Instagram and on Shopify and it’s-
I’ll have to snag one. I’m excited.
I’ll send you one. It’s the best thing I’ve ever done.
Yey, I love that. Cool, we’ll link it. Thank you for being here.
Thank you so much again to Danielle for sitting down with us. Make sure to check out Pretty Smart wherever you get your podcasts. I’m also on the show, we did a little show swap, so feel free to check out my episode as well as her other episodes. Follow Danielle on Instagram @daniellerobay, R-O-B-A-Y. Also check out her question card deck, it’s called Question Everything: 52 cards for deeper conversation. As always, everything is linked in the show notes. I’m going to do a nice seamless transition here and say, if you would like to be the most sophisticated, interesting, well-rounded person in the room.
Well, one of the ways you can do that is continuing to learn and continuing to know more about the topics you’re going to talk about. That’s part of why we build the show notes for you all, is we don’t want you to just listen for an hour, we want you to be able to dig in deep. We give you so much more research, ways to connect again with our guests. More information about how to better your money, all of that linked @financialfeministpodcast.com or at least in the description for this episode. So please check that out. Also, Donald Glover, if you listened to this episode, no, you did not.
Thank you for listening to financial feminist at Her First $100K podcast. Financial Feminist is hosted by me, Tori Dunlap. Produced by Kristen Fields, marketing and administration by Karina Patel, Olivia Conning, Cherise Wade, Alina Helzer, Paulina Isaac, Sophia Cohen, Valerie Eresco, Jack Conning, and Anna Alexandra. Research by Ariel Johnson, audio engineering by Austin Fields, promotional graphics by Mary Stratton, photography by Sarah Wolf, and theme music by Jonah Cohen Sound. A huge thanks to the entire Her First $100K team and Community for supporting the show. For more information about Financial Feminist, for Her First $100K, our guests and episode show notes, visit financialfeministpodcast.com.