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

0:00Hey 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.

0:33Were you always this confident 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 you know 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, well, maybe everybody does or everybody hates me or would anybody even care if I was around or or in this career?

1:08I'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. 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, 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.

1:42So 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.

2:16Do you have any examples of the time you faked being confident too much? Oh, yeah, 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, Oh, it's already. Yeah, sometimes I start talking. And I'm like, what the fuck am I even saying? You know what I mean? And then I'll 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 twenties, I wasn't aware of how strong my energy was or how strong my personality was.

2:50Now I'm aware of it. So I'm like, okay, be sensitive to others. You know, be, 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 turnoff 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.

3:25And it's like, why? Because, because I'm what loud? What, what is the reason you don't like me? Well, she's, it's like loud, but you, you don't have no problem with a man that's loud. So, So those kinds of things, 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. But I'm not going to adjust my personality to please anybody.

3:51I mean, I was always loud and 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, 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.

4:26At 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 going to do things. Did your sister ever call you and be like, what the fuck, bitch? Like, why did you share that on your show? Or why did you put that in your book about me? I mean, they're used to it at this point, but there have been two periods of time. I mean, I fund a lot of people in my family and I have and I always will.

4:54But 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, I 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 yep and I said all of that on stage like at 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.

5:48I 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.

6:17I'm going to do what I want to 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 going to 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 it. I was bored. It was fun, but I was over it.

6:44I 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. I'm like, I think this is my last year. I'm going to 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?

7:14You know, you're quitting. Are you ending the show? And I was like, well, yeah, you guys, it's a wrap. Like, we're going to end it last season. And I said yes to another season. I'm like, but I'm done. And they're 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 had 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.

7:43I'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, OK, well, I'm not being strategic. I 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? He's a music manager.

8:12He'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.

8:45Then 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 I want to buy a house yeah 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 stand-up for about six years I stopped doing stand-up and stand-up is the is the very thing that got me into this business and the greatest thing about stand-up 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.

10:28That was actually a great business move without even knowing that it was a business move. I became a stand-up 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.

10:49You 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. It's like, fuck men. I don't need kids. And I was like, Chelsea reminds me so much of my aunt. Because even now, we just started our company and we've had investors ask us, 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.

11:18Yeah, 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, exactly. Where are your kids? Show me a picture of them. Do you know where they are right now? Are you on Live 360, 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. I got pregnant a couple of 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 I 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 six dollar birth control that's going to last her for years like the arm and plant how do you think about like the rollback of reproductive rights in the U.S.

12:18what 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 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 uh-oh uh-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.

13:09The idea that men are trying to 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 we can't have you in boardrooms god forbid you can't have your own companies.

14:03So 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 wither men like that. And this is not all men, obviously. I don't want to make a blanket statement because 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 going to do anything. You can knock me down, but you're not going to knock over my spirit. I'm always going to tell you to fuck off let's talk about money because i think that's what's really changed since women got access to a credit card which is crazy to me it was so fucking recently 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 you know their budget should they be investing like how should they be thinking about that are there any financial mistakes you made early on or any like 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.

15:00Yeah, 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 involved, but 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. 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 that 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.

15:58I was like, oh, if I could burn through that, I'm going to act like a rapper. You know, I can't do that. Chelsea in 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.

16:29Like so when I see meet girls like you that have already like you've started your company, you're on 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, OK, 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, OK, 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.

16:58What 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 going to 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. I was doing something that nobody was doing at the time. And so you've got to think about that. If you're a comedian, what's your POV?

17:31What are you saying? What are you talking about? For me, it was like I was talking about how stupid men were at a time before people were talking about how stupid men were. I remember I had a joke initially 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 funny. Oh, that is so good. Like that was my whole thing. I'm like, I drink, I party, I sleep around, and you're never going to shame me about it. Like I had an unapologetic attitude about it, as I always will with women.

17:59Like why are we not all talking about that? My very first book was called My Horizontal Life, 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're 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.

18:31Just because we're not all talking about you guys are so. Because we're shamed for it. Yeah. This pure old 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 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 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 like 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 like 2 a.m and i drink it and then this guy comes up to me and he's like you drink my water and i was like off like it's just a water and then he was like no you don't understand like it was my mdma water and i was like what's mdma because 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 a.m oh my god i was like the happiest person i came back to the dorm the text i'm getting from her like i'm the most beautiful woman in the world the first text was like fuck i just took molly water 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 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.

21:06But 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 of COVID. I was like, OK, we're not allowed to socialize. I'm going to have a good time. I'm going to 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.

21:35And 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 when they literally me over COVID, I was skin with the audio book in 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 have 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.

22:30I want to be intentionally open-minded. If plans don't go my way and I end up in 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 going to 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.

23:02We were in my pool. I made him a frozen pizza. 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. I learned so much about him. I would have never taken the time to get to know him in any other circumstance, but really got to know this guy. And I love that shit. I love meeting people and hearing their stories, and I love absorbing that.

23:36What do you think about like in terms of, because you've been in some relationships or you've been in public relationships, some private, and you've been in public relationships also with people you've worked with. Sophia's 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 don't have any criteria for dating. You can tell by my dating history that there is no rule that I follow. So it's basically whichever way the wind blows. Like, I wouldn't advocate, oh, yeah, you want to date someone in your business.

24:02I 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. 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 have never been a priority in my life. I don't feel compelled to pretend otherwise.

24:34It'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. Like it's it's to inject women with this unapologetic attitude. Like don't apologize for taking up space. Take up double space, you know, and then help other women take up more space.

25:10We 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 it. 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. And when I was breaking up with him because we were in a pretty toxic relationship and I had to break up with him.

25:40But I also wanted him to know like what he was missing. Yeah. 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 going to be gorgeous during every season up there because 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, 20, 15 years since we broke up. Have you ever gotten back together with an ex?

26:10I 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.