The 3 rules Chelsea Handler thinks you should break to make millions

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Hey burnouts. Today we are talking to the one and only Chelsea Handler, the queen of confidence about how to take your career by charge and not feel bad about it.

Chelsea has built a huge legacy for herself in the world of comedy. She has seven books, six of which are New York Times bestsellers. She is touring internationally on her comedy tour. But today we want to take you behind the scenes on her career hacks. Her advice for how to be confident and how to be true to yourself. Chelsea Handler, welcome to the Burnouts.

Oh, thank you girls. So nice to meet you.

Were you always this close or is there anything Chelsea Handler is like that still makes me anxious or embarrassed?

I hear this all the time about myself and I guess so I guess I'm confident. I mean it's just who I am. So it's not something that I'm trying to be, but I have a very clear sense of who I am. And I guess I'm not super insecure about things. I mean I have moments of insecurity where I'm like oh, I second guess things. Or I've had periods of my life where I feel like, oh wow, maybe everybody hates me or would anybody even care if I was around or in this career? I've had periods of that. But you know, I think that's important to have self doubt at certain times in your life. It helps your growth and when you come back to yourself, you are even more confident after about like that. It's like when you come back from a failure, you're even stronger, you know. So I don't look at any of those things as negatives. I don't look at failures as negatives. It's just another part of the road. And it doesn't have to be a negative part. It's actually the closer, you know, the, like, the more failures you have, the closer you are to winning because you're getting closer to the thing that you want to accomplish, which is a win. So I've had so many wins and I've had lots of failures, but I think it's a matter of how you handle those kinds of disappointments. You know, you can't just. You can have a day or two where you feel sorry for yourself. And it's. You learn this as you get older and older and you have more to, to reflect on and you have more experiences to draw from to know that not any situation is the end all, be all. If something doesn't work out, it wasn't meant for you and it's okay. And pick your, you know, put your big girl pants on and like, go out there. And sometimes you have to fake being confident in order to attain that confidence.

Do you have any examples of time you faked being confident too much? Because I've definitely done that. Like, we've been on an investor pitch and I've been like, oh, yeah, no, we got that in the bag. And they're like, oh, well, then show me that. And then we're like, it's not ready.

Yeah, sometimes I start talking and I'm like, what the fuck am I even saying? You know what I mean? And then I'd be like, you have nothing to back that up whatsoever. So, yes, I faked it. You know, when I walk into a room, I definitely am walking into a room and I'm aware of my energy now. Whereas when I was in my 20s, I wasn't aware of how strong my energy was or how strong my personality was. Now I'm aware of it. So I'm like, okay, be sensitive to others. You know, understand that some people are going to find you intimidating. Men certainly are very. Can be very turned off by a woman who feels self empowered. And that's really disappointing. You know, we want our women to be empowered. We want our young girls to be empowered. So the idea that that's a turn off is like an ick.

Maybe it's the wrong kind of sex, then in that case.

Well, the wrong kind of men. I mean, I'm not having sex with those guys typically, but I have had sex with some of those guys, you know, but just in general, like, there's a lot of men, especially in comedy, they'll be like, oh, I don't like Her. And it's like, why? Because I'm what, loud? What is the reason you don't like me? Well, she's. It's like, loud. But you don't have no problem with a man that's loud. So those kinds of things, you kind of, you know, they can throw you off balance if you let them throw you off balance. Or you can just go, good information to know moving forward, you know. But I'm not going to adjust my personality to please anybody.

I love your comedy about your family growing up and being the responsible one household. Were you always funny from a young age or did it develop at a certain point?

I mean, I was always loud and, you know, opinionated from a young age. And so that is interpreted as funny because it's precocious when you're little. So, yes, I would get attention for that. And then I liked that attention. It was better than the attention for being cute. There's a lot of cute girls. Like, I want to have something different. But I was also the youngest of six children, so I had to be loud and precocious to get what I wanted and to get, you know, you know, attention in a family that large. So it was. I mean, I was definitely born with a personality, a strong personality and a strong sense of myself. At a very young age, I felt like I was a woman. Even when I was, you know, three or four years old, I'm like, I can't wait to be a woman. And I wanted a briefcase, and I wanted my own place, and I thought my family was holding me back. From as early as I could remember, I thought, this is not how I'm gonna do things.

Does your sister ever call you and be like, what the fuck, bitch? Like, why did you share that on your show? Or why'd you put that in your book about me?

I mean, they're used to at this point, but there have been periods of time. I mean, I fund a lot of people in my family, and I have, and I always will, but I was funding my sister, and she just. At one point, I said to her, this was many years ago, probably 15, 20 years ago, and I was at. On stage at Radio City Music hall, and I was, like, talking about my sister and how she hasn't worked in five years. And when I asked her, when I asked her, I was like, do you maybe want to go back to work at some point? She's like, I'm really happy staying at home. And I'm like, yes, but I'm working to pay for you. My older Sister, like, it's been five years. I want to help you, but I don't want to support you fully. And I said all of that on stage, like, while she was in the audience. So that was bad.

It was a little rupture and repair there.

Yeah, there was a bad. That was a bad moment. And my whole family had to get involved. And then she was very upset and she was very embarrassed. And I was. You know, I shouldn't have done that, but I was. I'd had it, you know, Instead of, like, creating a healthy boundary, I had let the boundary get out of control and then resented her for it. So, like, I don't do that shit anymore, you know, I have boundaries. I tell people how I feel directly.

Especially in business, right? Like, you meet all these men. They suck. They're really rude. But how do you say fuck you in corporate speak?

Well, it's nice to say you're not interested when you're presented with a deal. If I don't want to do something, that's a big fuck you, people think that they can buy you like, that you're for sale. You're going to dangle this paycheck in front of you and you're going to say yes. And it's like, that's not how I operate. I'm gonna do what I wanna do. I'm totally happy to get a big paycheck and play along, but with my set of rules and my personality and how I'm gonna do it. Not with your set of rules.

Can you explain for our audience? You've done so many incredible business deals with E. Netflix. What does it look like? Isn't an agent involved always? Do you have to have a special entertainment lawyer? What kind of rules do you have when you're reviewing a contractor? How do those deals look? How are they even structured at E?

I think I did seven years of Chelsea lately, and I had had it. I was bored. It was fun, but I was over it. I needed something more challenging. The last thing I ever like to do is coast. Like, I always need a new appetite for something or a new interest. So I was like, okay, I think I'm done. And I was doing the Howard Stern show in New York, and I just told him on air, and I'm like, I think this is my last year. I'm gonna wrap it up. I hadn't told anyone else that, and I just said it because we were having a real conversation, like we're having now. At that time in my life when I thought something, I thought I had shared it with people, and so. But I hadn't. So when I got back and walked into my studio, you know, half the staff is like, what do you mean, you know you're quitting? Are you ending the show? And I was like, well, yeah, you guys, it's a wrap. Like, we're gonna end it last season. And I said, yes to another season. I'm like, but I'm done. And they were like, how could you not have told us before you told Howard Stern? I'm like, you're absolutely right about that. But I didn't even think about it. I just thought everybody kind of could read the temperature and that I was done. E took that to mean that I was trying to negotiate for more money. So they thought it was, like, a tactic, which is not the way I play at all. Like, I'm actually not very strategic in anything I do. I'm just very direct and real about it. I'm more like, what interests me now. I'm not looking to be a billionaire. I don't care about that. I want to just have a nice, happy life. So I wasn't being strategic, and I said, okay, well, I'm not being strategic. I'm just actually need a break. I called this guy, Irving Azoff, that was a friend of mine, and I was like, hey, can you deal with E? Because they think I'm trying to negotiate, and I don't want to talk to them about this. This is the part of the business I don't want anything to do with.

And this guy you're calling, is he an agent? What is.

Like, he's a music manager. He's a music mogul, actually. But, I mean, he manages all these bands, and he's an old guy, but I was just friendly with him, and he seemed like an asshole. Like a fun business asshole. So then he came to me. I had a few offers, and then Netflix came with an incredible offer. We just kind of negotiated what I wanted to do. They wanted me to go right back into a talk show. And I was like, no, I need a year off. I was like, I'd love to do a series of documentaries. So I did, like, four documentaries. I did this series called the Chelsea does series, and then it was a three year deal structure. The first year, I had six months off. Then I shot the documentary. So I worked like, six months of the year. The second year, I started the talk show, and then the third year was the second year of the talk show.

Our show is called the Burnouts. You have a comedy Special, seven books, you're going on tour. How do you manage all of this without burning out?

Well, that was a perfect example of a burnout because it was seven years and it's a seven year itch. And I think that applies to almost anything. If you do anything for seven years, you're going to be fucking bored by it.

Yeah.

Like, it's like a marriage. Trevor Noah left the Daily show after seven years. James Corden left his show after seven years. It's kind of a repeated cycle. So that was a total burnout. And that was a lesson because when I was doing Chelsea lately, I was. I had written, I don't know, two, three books in the period of seven years that I was on that show and did probably four comedy tours. And this was before specials were like what they were. So you didn't shoot a special every comedy tour. I think I did one special in seven years for Netflix and I was like, okay, I can't burn out again. It's so important for me to, like, have long breaks, like six months off. I want to go to Europe. I want to buy a house in Spain. I want to do this.

Did you buy a house in Spain?

I did. I bought a house in Mallorca, which was the best gift I've ever bought myself. And it's the gift that keeps on giving. And so when I went into the Netflix show, I was like, okay, I don't want to get into this routine again. I don't want to be burned out. I don't want to be working all the time. So I stopped doing standup for about six years. I stopped doing standup. And standup is the, is the very thing that got me into this business. And the greatest thing about standup is you are creating your own narrative. Like when you do stand up and you're a bonafide stand up comedian, things are created around you. You're not being cast in things. Things are like, television shows are created around you as the host or as the star. Like sitcoms are built around Roseanne or built around, you know, the star of the sitcom is usually a stand up comedian. That was actually a great business move. Without even knowing that it was a business move. I became a standup just because I didn't really want to read other people's material. I was like, I have material. Like, I can tell stories until I die about my life. Like, let me just do that.

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You have seven books. You're such a badass. And my aunt, no joke, has seven cats. She's been through two divorces. She's like a badass. Single woman is like, fuck men. I don't need kids. And I was like, Chelsea reminds me so much of my aunt because even now with we just started our company and we've had investors ask us like, what's going to happen to the company when you have kids? And I'm like, who told you I want kids?

Why are you even allowed to ask that question?

How did you develop the confidence to answer that question? I feel like when the investor said that to me, I was like, I didn't even know what to say.

Yeah, but that's such an inappropriate question. The answer back was like, would you ever ask a man that question?

And what about when you have kids?

Yeah, and where exactly where are your kids? Show me a picture of them. Do you know where they are right now? Are you on Live360, an app I don't want ever to be a part of? No. But I just never wanted kids. That was an easy decision. It wasn't a hard decision. You know, I got pregnant a couple times when I was a teenager and got abortions. Thank God my parents had the sense to make sure that that happened. And thank God as I got older and more mature I understood that that's not what I'm cut out for. That's not my lifestyle. And I'm good at a lot of different things, but that's just not one of them and that's okay. So the idea that we all have to be all of these things is just so silly.

I love how open you are too about having abortions because I feel like it's such a taboo subject. And one thing like I've really focused my advocacy work on is reproductive freedom, reproductive rights, because there's nothing more scalable than giving a woman access to $6 birth control that's going to last her for years. Like the arm implant. How do you think about, like the rollback of reproductive rights in the US what we're kind of seeing with the current administration.

I'm reading this book. I forget what the name of it is. My friend, my makeup artist in New York just gave it to me. And it's just this history of women and all of the contributions in the arts that women have made that have been erased, like by erasure, you know. So like in the 60s, this thing I read last night, in the 1600s, there was like this, you know, huge art renaissance movement in Paris and all these famous painters and oil painters. And then like women came on the scene and there were like 3:13 that were really big at that time. They had exceeded men in stills, in oils and all of these areas of art. And then like you go ahead two more centuries and they've just been completely erased. So like men caught wind of how talented women were and were like, oh, oh, we'll actually take your work and put our names on it. Which, you know, has happened throughout history, but it happens over and over and over again. The idea that men are trying to see stop women from succeeding is because we are a threat to men. We've always been a threat to men. Men don't like women that are self assured, that are self empowered. Even in the day that we are living in, even after we have modernized this country, there is still this death cough of white male supremacy where they want women at home to make babies so that they can be in charge and make decisions. The idea of another person having autonomy over your body is absolutely barbaric. And from the Middle Ages and the fact that they want to go back to that just proves how scared they are of women's success. Because now more than ever, women don't need to get married. We're weighing whether or not we want to have children. We're actually making these active decisions. And then we become their competitor. And they're like, whoa, whoa, whoa, whoa, whoa. We can't have you in boardrooms. God forbid you can't have your own companies. So you just get used to that. That aspect. And get used to standing your ground with men. Because the thing they love the most is to see you with her. Men like that. And this is not all men, obviously. I don't wanna make a blanket statement. Cause there are great men out there, but there are men that will want. They want to intimidate you, they want you to shrink. I find that to be a great challenge. And I enjoy it, you know, because you're not gonna do anything. You can knock me down, but you're not gonna knock over my spirit. I'm always gonna tell you to fuck off.

Let's talk about money. Cause I think that's what's really changed since women got access to a credit card, which is crazy to me. It was so f. As you've come into wealth, like, what financial tips do you have for young women who are like, starting their careers, learning how to manage their budget? Should they be investing how should they be thinking about that? Are there any financial mistakes you made early on or any just general advice you would give women about how to manage money? Because we know that that financial freedom is how we gain power to say, no, fuck you, I don't want to have your kids, I want to have this career.

Yeah. I think you have to be as educated as you possibly can get about money. I'm not the perfect example of that. My investments are real estate. I wish I knew more about the market and I wish I was more invol. That's just not an area of interest. I have people who do that for me. I bought a lot of homes. I bought a lot of family members homes. And that is kind of one of the best investments you can make is real estate. You know, that's never going anywhere. That's always going to increase in value over time. So as far as stocks and the market goes and all of that stuff and investing in companies, I definitely do it. But I wouldn't say that's where my strongest skill set lies.

What did you do when you got your first big paycheck? How did that feel for you?

I just wanted to buy people things. Do you know what I mean? When I started making like millions of dollars a year, I just wanted to spend it and buy people things. I bought my sister a house. I bought my other sister a car. I bought myself a house. And there was just like Kind of no end in sight. Because when you're really rolling in, you're rolling in it. But I didn't want to ever be stupid. I was like, oh, if I could burn through that, I'm gonna act like a rapper, you know, I can't do that.

Chelsea and the Chain. I would like it. I'd be here for it. I think it's really cool because when you had your late night show, you were the first woman to do that. Like, are you watching or looking at other young female talent in comedy that you're excited by?

Yeah, I mean, there's tons of. Now there's so many women and the world changes so quickly, especially since we finally fucking got an Internet, you know what I mean? It changes every 10 years and now it's changing every five years. So it's like we're watching everything change so rapidly. Like, so when I see meet girls like you that have already, like, you started your company, you're. I'm like, holy shit. I didn't have my shit together at that point. At that point I was like, out for my, you know, for myself. I was like trying to get noticed and trying to get attention and trying to get on TV and trying to get my own show. And then once I had that, I was like, okay, great, let's run with this. And then you run out of, you know, you run out of steam for that. And then you're like, okay, what's the next thing?

Entertainment industry is so hard to break into. I have friends who want to be like an aspiring actress or maybe even an aspiring comedian. What would you say to those young girls who are struggling, who really want to break in?

You have to be relentless in your pursuit of what you want. You have to move towards it like you're a bowling ball going down a lane and that anything that gets in your way is gonna get knocked out of your way. Like, you have to be so intentional about making it because there's millions of people trying to do that, you know, and I was really lucky, but I was also really talented. Like, I didn't. I was doing something that nobody was doing at the time. And so that's. You've gotta think about that. Like, if you're a comedian, what's your pov? What are you saying? What are you talking about? For me, it was like I was talking about how stupid men were, you know, at a time before people were talking about how stupid men were. I remember I had a joke initially, like in one of my first stand up sets that was Like a guy said to me, you don't have to drink to make yourself more fun to be around. And I was like, no, I'm drinking so that you're more fun to be around. Oh, that was my whole thing. I'm like, I drink, I party, I sleep around, and you're never gonna shame me about it. Like, I had an unapologetic attitude about it, as I always will with women. Like, why are we not all talking about that? My very first book was called My Horizontal A Collection of One Night Stands. And everyone in America is like, oh, we don't. It was so sanctimonious. The reception that got every American publisher was like, this is too risque. And then Bloomsbury, a British publisher, picked up the book and they were like, this is fabulous. And they sold it in like 74 countries. They translated it into 60 different languages, and it was a huge success. And then all of the American publishers, like, we want to do a book with you. And I was like, hey, by the way, every 20 year old girl is doing what I'm talking about. Just because we're not all talking about. You guys are. So. Because we're ashamed for it. Yeah. This puerile country we live in, it's just nonsense and so silly. So you kind of have to break what you don't have to break whatever business you're going into, but you have to be adding something that's not there.

I love how open you are about.

You know that.

But also, even better, drugs. I love how open you are about drugs. Like, I think you've talked about writing while you're high or, like, being creative. Walk us through that. Like, I want to hear the Chelsea Handler pitch on why drugs are great.

The kind of iterations that we've gone through with drugs and now where we are with them with microdosing and all of the data behind how helpful they've been with people who are war veterans or people who struggle with ptsd, who have real bad traumas, even brain traumas, people who have had strokes, like the, the healing components of lsd, microdose or ketamine or mdma. You know, they do couples counseling with couples and they have. They give them both MDMA because it's a heart opener. Like, we should try it. You should try it. It's fucking awesome.

Wait, I did. I did Molly by accident. I drink Molly water. I was eating a burger. I was at this club, and this is when I was sober. Literally, like, I didn't drink at all. I see this water and I'm thirsty. Obviously. It's like 2am and I drink it. And then this guy comes up to me and he's like, you drink my water? And I was like, fuck off. Like, it's just a water. And then he was like, no, you don't understand. Like, it was MDMA water. And I was like, what's mdma? Cuz, like, I didn't know. And he was like, molly. And I was like, the drug. I literally went and tried to make myself throw up because I was so scared. I was like, oh, my God. Oh, my God. And then this woman comes up to me and she's like, girl, you just need to live your life. Like, you just need a vibe. And I was like, honestly, facts. And then I went and I partied until like, 6:00am oh, my God. I was like the happiest person.

The text I'm getting from her, like, I'm the most beautiful woman in the world.

I'm like.

The first text was like, I just took Bollywater. I'm gonna die. I'm gonna die. So I'm like, calling her, calling her. Next text I get is like, please, I'm busy. I'm a goddess, and I'm the most beautiful woman in the world, so I'm gonna need tonight on my own.

I was like, are you okay? I was like, I love you so much. I love the world.

You love everyone you hate. You love them when you're on Molly. It's a beautiful, like, drug. Everyone in this administration should fucking take it. It would make the world a better place. I had a birthday party in Whistler this year, and everyone took it. I mean, the staff, the guests, everyone. We gave it to the bartenders, the servers, and we were all just having the best time. And we can all work our asses off, but the relaxation and the time off is a component of success. You have to be able to take it down a notch and to be loose and to have fun, you know, like, especially if you're tightly wound and you're an uptight person, you have to be able to loosen up.

But I need to know the story of you doing drugs with your landscaper.

That was during COVID How did it start?

Because you've talked about it. But how did it begin? Was he like, we should do drugs together? Were you like, that's a great bush? Like, did you come up with that bush design while on drugs? Like, how did that conversation start?

I was doing tons of mushrooms during this time in Covid. I was like, okay, we're not allowed to socialize. I'm gonna have a good time. I'm gonna read books. I had all these books I hadn't read in my house. And I'm like, this is perfect. So I would smoke weed or take an edible. And then I was like, I moved on to mushrooms. And then I had all these edibles that were like 90 milligrams. And I was like, ooh, I wonder if I could take that and survive. And I was like, finally, like, I built my way up through them and then I was just like, on so many, and I was still functioning. Like, I was working out and I'm like, God, you're a beast.

And then one day, this is literally me over Covid. I was skiing with the AudioBook and the AirPods.

And then one day my landscaper was there and we were just talking and I was. I think I was probably smoking a joint. And I always share my drugs. I said. He said, how have you been spending your time? And I told him. I was like, I've been tons of drugs. I'm like, if you want any, I'll give them to you, you know? And he's like, yeah, I would love to. He's like, I got nothing going on. We tripped together like three or four times. And we had a great. We had so much fun, great conversations. And it was one of those experiences. Like, I want to be more open minded with everything I do. Not narrow minded. You know, narrow minded doesn't yield all of the results. I want to be intentionally open minded. If plans don't go my way and I end up in some Spain for, you know, for example, by accident, like, say I'm heading somewhere and they're like, okay, we're landing the plane. You're. You're not getting to your destination here. Then I'm gonna have a good time there.

Like, it's always back to Mallorca for you.

Yeah, it is. I want to have a good time when things don't go my way. I don't do that all the time. It's not like I'm perfect, you know, in the bigger picture items, you really want to make an experience. Like my experience with him that first day that he and I did mushrooms together, we laughed so hard. We were in my pool. I made him a frozen pizza. Like, to me, that was like making a meal from scratch. We had just the best time and we were bonded after that. He's still my landscaper. I've moved. I mean, we are bonded. Like, I learned so much about him. I Would have never taken the time to get to know him on the, you know, in any other circumstance, but really got to know this guy and. And I love that shit. I love meeting people and hearing their stories and I love absorbing that.

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No problem.

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Of course.

More branches and ATMs.

Way more.

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Easy.

Everything right at your fingertips. And what about my business?

Always here to help you reach your goals.

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What do you think about, like, in terms of. Because you've been in some relationships where you've been in public relationships, some private, and you've been in public relationships also with people you've worked with. Sophia is dating an entrepreneur. My boyfriend's not an entrepreneur. Like, do you think it makes sense for people to date people in similar careers? Would you suggest it?

I mean, I have any criteria for dating. You can tell by my dating history that there is no rule that I follow. It's basically whichever way the wind blows. Like, I wouldn't. I wouldn't advocate. Oh, yeah, you want to date someone in your business? I mean, no, I think that kind of is narrow too. Like, you want to open it up.

What's the longest relationship you've been in?

Four years.

And that was too long.

That's how I feel.

I'm about an 11 month person. I go for about 11 months and I'm like, okay, this is getting a little, you know, I'm bored now.

Wait, how do you balance work, life, and dating? Like, you're such a badass. You have so much going on. Like, how do you make time for a man? Because we don't make time for our boyfriends. To be honest, I don't.

I slot them in. Like, it's not a priority.

Men are.

Have never been a priority in my life. I don't feel compelled to pretend otherwise. It's just not my thing. I'm not here for men. I love men. I want to have sex with lots of different ones. And I'll have relationships. And if I fall in love, great. I'm not against that. But I'm not looking for a soulmate or a partner or anything like that. I'm here for women. That's my purpose. I want to be creative. I want to help women. I want women to feel confident in the way that I feel confident when I put out a book or I put out my most recent special on Netflix. It's to inject women with this unapologetic attitude. Don't apologize for taking up space. Take up double space, and then help other women take up more space.

We need to, like, play that for our boyfriends. We are not free. We are launching our company.

Yeah, yeah, please.

Wait.

But with men, I mean, they're just, you know, you fit. Like when I'm skiing, I have a boyfriend there. If I'm in Mallorca, then there's a guy from Europe coming. You know, like, it's kind of very casual like that.

And who's the guy? You. There was something where you gave someone trees or something so they couldn't forget you.

Oh, yeah. I gave an ex boyfriend trees at like 35 Linden trees as a parting gift when I was breaking up with him. Because we were in a pretty toxic relationship and I had to break up with him. But I also wanted him to know, like, what he was missing. And I bought him these 35 trees. And he had this estate in upstate New York. The trees basically lined his driveway on either side for naming, like a canopy overhead. And I knew they were gonna be gorgeous during every season up there. Cause it's so beautiful up there in the spring and the fall. And every spring and fall, he texts me and he's like, look at your trees.

Please come back.

And I'm like, I'll never be back.

How long has it been?

Oh, it's been like 15, 15, 20, 15 years since we broke up.

Have you ever gotten back together with an ex?

I would not recommend it. I think that's bad. When we're young, we really. And hopefully. I don't know if you girls are like this, but you both have boyfriends. We take relationships so seriously. They don't have to be that serious. Like, your careers are way more important than any guy. And also your friendships with other women and your relationships with other women are way more important than any guy.

Yeah. I used to hate when people would always ask me and Phoebe in college. Well, first of all, people thought we were lesbians because we spent so much time together and we were always working. But they were like, what about the guys? And we were like, ew. Like, we have things to do. Like, we're trying to launch our company. But what would your advice be to young women who, like, do get asked about stuff like that? Like, oh, are you dating anyone? And like, they're not. Like, what's your go to response?

I have dealt with that my whole life too, where it's like, oh, gee, is there anyone saying, my Russian sister in law, like, like, it's like, know me less. Like, she hasn't learned at all over the 25 years that I've known her that I don't fucking give a shit about boys. Like, that's. I'm not boy crazy. And she's like, is there anyone, Chelsea? Is there anyone? And finally I just, I was like, I don't have to vacation with this woman anymore. Actually, like, these lines, this line of questioning is like, I feel like I'm 18 years old, she's still asking me about boys. Like, I don't want to deal with this. I have cut some people from my family, to be quite honest. Like, in terms of, like, going on vacations and stuff. As you get older, you're like, how am I spending my time? Like, I'm paying for these vacations. Then I started to think about it in a serious way. I was like, actually, I've been. I've extended my generosity enough. Now I'm gonna do what I wanna do.

Do you ever do that for your team? Like, in business where you're like, get your shit together. Like, what are you guys doing?

Yes.

Yeah, for sure.

You know, really, like, how did you find your current team?

You know, you have to make decisions at some times in your points in your career where you're like, this isn't working for me. Unfortunately, right now I feel like I have a good a Plus team bringing me opportunities instead of me self generating my opportunities. My podcast, my books, my standup is all self generative. So it's like I needed a team to come in and be like, bring me some opportunities. I don't want to just be the only one hustling here.

And walk us through how to like, you evaluate those opportunities when they're brought to you. Is it usually like, okay, payment? You get equity in the business. Like, what, what does a brand deal look like for people?

Well, sometimes it's a partnership, you know, and sometimes it's a. And it's, it's an endorsement. And this happens on my podcast a lot too. They'll be like, oh, this is a host red ad. Or do we want you to endorse it? If you want me to endorse it, then you have to pay me more money and I have to actually try the product and say that I like it. I mean, I have to like it. I'm not gonna just say, oh yeah, try this. I love this. So there's all different variables and variations of deals, but it's a matter of not just saying yes to anything that comes your way. You know, there's been many opportunities and we actually sat and talked about it. So I'm not just like, hey, pay me, I'll do this. It's like, let's talk about it. Does this make sense? Like, Gold Bond is a perfect example. Gold Bond, which is like, you know, when I heard about Gold Bond, I was like, I remember my brothers using that for their balls. It's this moisturizer. It's fucking awesome, by the way. I mean, my skin is so soft because of it. But they had this great ski campaign. They wanted me to ski in this gold bathing suit in Tahoe, Palisades, and break the skinnest book of world records. And I'm like, nobody loves skiing in their bathing suit more than I do. Like, what a great brand, like, partnership, you know, like, that was thoughtful.

What about glasses? Brand partnership? I feel like you have to. You're always classically wearing your glasses. I feel like that's one you need to do.

I got that offer actually recently, but I said no because I just don't feel passionate about that. I'm always wearing different glasses. It's really about whatever's like, available. You know what I mean?

Yeah.

And if I'm tired, you want to just cover up your face, you know, you're just like, fuck.

How can more women advocate for themselves in business to be like, I want this and I deserve this.

Well, because you have to. Because if you don't say it, first of all, you have to believe that you have value. And that starts by telling yourself that you do have value. We all do have value. It's true for every single one of us. It's all about finding out what is your value, what can you add to the situation, and having the competency to know that you are capable. And then when you believe it, like, then people can start to believe it. So when people are like, oh, nobody believes in me. It's like, it starts from you. You have to believe in yourself, and. And that's kind of like an inside job. You got to figure out what your strengths are and what your weaknesses are and go after the things that you are good at. And also let people know what you're good at. And don't be shy about advocating for yourself, because there's nobody else that's going to do that for you.

I love that. Yeah. Because I think also that's so true in the sense that I think so many women apologize, especially when we're young.

This is something I struggle with too. Like in a meeting with someone, I'm like, well, I'm sorry. Like, maybe that's on me. Or when I know it's not on me. There's one thing of saying sorry, which I love, the way that you address, like that situation with your sister where you're like, yeah, well, I did really mess up there. And that is, like, something I've learned a lot in our relationship, to be honest about that. But I feel like there is a pressure to. To, like, just say sorry when you don't actually mean you're sorry. Is that something you've ever struggled with?

Always. I mean, people say sorry all the time. All that. We always say it. Women. Women say it all the time. We're sorry. We're sorry. We're sorry. We're sorry. And I have made a cons, like, very conscious effort to not be apologizing. Even, you know, if you're interrupting someone. Excuse me. Excuse me for interrupting. Not I'm sorry. Cause you're not really sorry. You're about to talk. So excuse me, but I have a point to make. I have a friend who's a CEO, and she has this habit of when you're, you know, you're in conversation with somebody, there's a lot of interrupting that happens by nature of just talking. You're like. You say something, and I'm like, oh, I remember that. Or whatever. When that happens, she just Keeps talking, talking, talking. And it's because of her years and years of being in boardrooms and being the only female in all of these boardrooms with all of these men where she has to talk over them when they say something because she has to get her point across otherwise she won't be heard. It's one thing when you're, you know, you need people to invest in your company, but when your company is strong and you have a great business model and a great business plan or a great product, you don't have to go in and kiss ass. Yeah, you have to go in and be a badass and be like. So when you walk out, everyone's like, God, we want to be in business with them. How could we not? Look how powerful that person is. Like, that's what you have to be like. And there's no shame in that game. Men do it all the time.

It's so sad. Like less than 2% of venture capital financing goes to women. And I think it's a byproduct of just how over prepared we had to feel. The men always, they don't even have a deck. They go in and they raise capital just off of vibes. The women. It's like you have to have the answer to everything. A super long business plan. We had everything. We had the business plan, we had the financial model, we had the deck. And it still felt like it wasn't enough.

Who pitched it when you guys went in to get finance?

So our first couple pitches were horrific. I mean, we get on the phone, we had no deck. Like we were bumbling and fumbling our way through. And finally we had this great mentor named Joanne Bradford. She worked at Pinterest for a long time and at Microsoft. And she helped us like learn how to pitch. And so we honestly, when we would go and do these pitches, we were like a well oiled machine. Like one person of one side, one person another side. We had a list of like 100 potential questions they could ask us. We'd go into pitching and I felt like I wasn't a person. Like I would be like, now we're going into this like skit that we've practiced a million times.

Yeah, well that's what you would have to do. In that book I was telling you about earlier, there was this art historian and he was writing like he was trying to encapsulate like the 15th, 16th and 17th centuries of art history. And he's like, I just can't find any really good women. And this woman makes this argument like, men have access to everything that we don't have access to. And still, still, when we enter the game, we excel still with all of the barriers of entry, but with having to stay at home, with having to be a mother, with having to feed your children, with having to take care of a house, still, we can create art, and we will still excel at it. Like, with all of that, when you guys are just handed all these opportunities, you get to go to the best universities, you get to study all of these things. You get every door open for you. I mean, obviously we've heard this argument millions of times, but it's nice to hear it in every context to know that you're not just crazy, that this is a male dominated. Everything is male dominated. You have to work twice as hard to get in the door if you're a person of color or you're a woman.

I think something I struggle with sometimes is like, public speaking or walking your room. What would be your tips for someone who's like, I'm really not funny. How do I be funny?

Well, I mean, if you're not funny, then don't try to be funny. Be what you are. If you're smart, be smart. If you're innovative, be innovative. Like, whatever you are, you don't have to be funny to grab people's attention. Public speaking is very, very difficult for a lot of people. You have to be passionate and believe what you're saying, regardless of what the subject matter is. And I don't think it requires you to be funny, you know, to be captivating or compelling. Make eye contact and look at people and connect. You know, I have a friend who I saw make a speech, and she didn't look up once, and I was like, oh, my God. And I was sitting next to her boyfriend, and I was like, oh, my God, is she gonna come back here and we're gonna pretend that was good. Cause, like, I can't tell her that was good.

What'd you guys do when she came back?

She didn't come back to the table. I looked at her boyf and he went. And I was like, oh. And then I. Afterwards, she was like, how did that go? And I was like, we'll talk later.

What did you tell her?

I told her the truth. I said, you got to look up and look at people. You're in a room of, like, 500 people. Make eye contact. Make people feel like they're being seen and that you're connecting with them. You connect with someone, you make eye contact with. They want you to know that they're listening. You know what I mean? I feel very comfortable publicly speaking, but I didn't in the beginning. It was very scary. But you just. I've been doing it now for so long that it's like the easiest thing in the world.

Well, Chelsea Handler, thank you so much for joining us on the Burnout.

It was a pleasure. So nice to meet you girls, and congrats on your company.

Thank you.

Launch day.

Awesome.

So now what do you wait to happen? You wait to see how many people download the app?

How many people download? We optimize our onboarding flow. We have a lot of shit we need to improve. To be honest, right now we're a price comparison tool, but we want to expand to being truly like your own personal shoppers. Like showing you your closet. Like helping you decide, no, you shouldn't buy this because you have this in your closet already.

Personalized recommendation.

So we have a lot more to do.

That's really good because I have so much double shit in my closet, you know, so many of the same fucking black boot. And it's like, yeah, you see side and you're like, I've got to have those. And you're like, you already fucking have those.

FIA's gonna say, no, Chelsea, don't buy them.

Yeah, I love.

How can I help you today?

Hey, I need to talk about my loan.

No problem.

So I got the email. Sandy Spring bank is becoming Atlantic Union Bank.

That's right.

And will you still be your banker?

Of course.

More branches and ATMs.

Way more.

Still community driven. Still live here. Still give here mobile app.

Easy.

Everything right at your fingertips. And what about my business?

Always here to help you reach your goals.

Sandy Spring bank is becoming Atlantic Union Bank. October 2025. Same bankers you love, with even more to offer.

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