Judi Holler – CEO of HOLLA!, Comedian and Author of Fear Is My Homeboy

Episode 117

Judi Holler shares all of her awesome fear-crushing advice on this episode of #TheKaraGoldinShow. Exec turned comedian, she shows us all how fear can actually help you to be braver than ever. Her new book, Fear Is My Homeboy is so good!

Listen as we hear more of her personal story and how she finally stopped allowing fear to call the shots in her life. So much to be inspired by in this interview. Listen to this episode to find out!

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Kara Goldin  00:00

Hi everyone, it’s Kara Goldin. And I’m so excited to have my next guest here who is not only a total badass keynote speaker, podcaster, comedian, CEO, and author of the book fear is my homeboy how to slay doubt boss up, and succeed on your own terms. Welcome. Welcome, Judi. Oh, thank you, Kara. So good to be here. And it seems like people have a love affair with slaying doubt, and overcoming doubt, and moving through it and moving with it. And so it’s just, it’s an honor to be here for real. I absolutely. If you go to JudiHoller.com. She has just a few videos there that really talk about your backstory. And I remember looking at it and was just blown away, and I knew who you were. But actually, I mean, you just did an amazing job on that as well. But also just it’s so inspirational on so many levels. So, Judi, is, as I mentioned, has done a lot. She wears a lot of hats, like many of us, but she’s also a jack of all trades and truly embodies the spirit of the creative entrepreneur. And her company that she’s the CEO of is called pull up productions and Holla Holla Holla Holla sorry, CEO of holla productions. And she as I mentioned, as a podcast host and author of the best-selling book fear is my homeboy how to slay doubt Bossip and succeed on your own terms. And if that isn’t enough to impress you, then we’re just going to keep chatting a little bit about some of the other amazing stuff that she’s doing. in her own words. She’s a bonafide improv nerd, who is obsessed with helping people live a braver life and lead brave braver teams as well. So anyway, thank you so much for joining. So let’s dive right in. You started out studying and performing Improv Theater. Talk to me a little bit about that. How did you get there? First of all, like, Where did you grow up? All of that kind of

Judi Holler  02:24

All the things okay, so I am a St. Louis girl born and raised in the Midwest, by the way, my husband’s an ASU guy so funny story, we have a connection to Arizona as well. And so my husband told me to tell you to go devils, but I have no connection to Scottsdale or Arizona or that area. But I grew up in the Midwest, and moved from St. Louis, Missouri, to Chicago, Illinois, by way of a big promotion and sales and marketing. I worked in the hotel industry, hospitality was sort of my background. And I grew from property-level sales working in big convention hotels, booking big conventions to regional sales, where I represented companies like Marriott Starwood, back when there was a Starwood ami, etc. And I was responsible for bringing and growing business in that hotel collection. So I opened hotels and was based in Chicago. And it was an incredible career. And I knew that when I got to Chicago, I had this feeling that I was going to have to try improv. So I have a little bit of theatre background. But I was never a theater kid. I did like the speech. And I loved the sales presentations. When I was working in sales and marketing. I loved storytelling. I loved finding unique ways to get people’s attention. And I’ve always naturally love to worry, I love to talk. I love to tell stories. And I love to find a way to do that differently. And so I thought improv could help me sharpen that skill. And little did I know that just going to take a class, though basic classes, the classes, anybody could go take, by the way, at the age of 30. So I think that’s important. I think a lot of people think oh my god, I’m too late. Or my I’m too old, or you know, everyone’s gonna make fun of me. And I’m not smart enough. I’m not funny enough. All this stuff, right. And I tell this story in my keynote, one of my signature stories is the story of how I went it 30 karas, and then I left like I quit. I lied. I said I was in the wrong place. I was supposed to be at Starbucks and I left and it took me two years to go back to the second city. So at 32 essentially, I took my first ever basic improv class, caught the bug, and ended up auditioning for the Conservatory, the professional program after a few years got in stayed in, and am an alum.

Kara Goldin  04:47

Can I jump in for a second? So when you left to did you leave because you were booed off the stage or what? What kind of a question yeah, what happened?  I was so afraid. It was fear and fear alone, I was afraid that I was too old that I was too late that all these 20 somethings were going to boot me off the stage or make fun of me, or that I had missed my chance. And so I quit. And, you know, the big idea is, would it be great if we could stop, you know, allowing fear to make our decisions to stop missing opportunities, because fear, you know, has started to call the shots in our life and, and I quit that day, and I regretted it for quite some time and went back two years later. And it’s funny in my keynote, I end up flashing this photo on the stage, but it’s the photo of my very first ensembles. So when I went back at 32, I mustered up the courage. I was reading a lot of Bernie brown and books on courage, I finally mustered the courage up to go back. And the first human being I saw in that room was a woman named Shelly, who at the time was a 55-year-old University of Chicago Professor taking improv to think on her feet. And there was a guy named Frank who was 56 years old sales guy taking improv to become a better presenter. And it was this melting pot of humans all looking for something different. What I found what I went for was presentation skills and have some fun and meet people. I was single and living in Chicago. But what I got was courage in a way that I never thought I’d get because here I was doing things on the improv stage that made me really brave in front of hundreds of people with no script. And you know what it did Kara? It made me boss up in the boardroom, I started, asking for raises, I started speaking up to that toxic person at work, I moved to New cities, I left bad relationships, I sit in the front row. So yeah, there it all began. There. It all began and I just started talking about it. I asked my sales director, can I lead the sales meeting, I learned this really cool thing at improv, I think our team could use it. And I would just speak for free to anyone who would listen and I have turned it into a full-time speaking and creating and writing career on fear, courage, and confidence. That’s amazing. That is so great. So did you like growing up? Were you funny? Did your friends think you were funny? I mean, it’s, uh, I mean, it’s funny, a lot of my friends Today, well share stories where they all knew I was going to be an entrepreneur, but I always call myself an accidental entrepreneur. There were like, you were planning a kid’s camp at age 12. You know, and you were just like, Come on, I’ll be fine. We’ll charge five bucks. You had no idea what you were talking about. But I just was able to kind of convince people, you know, I was leading them. But I didn’t call leading then. And I was like, I, you know, was my idea. And I would, I would do it. But anyway, I’m, I’m so curious. Like, did you think you were like, Did people think you were funny? Or did you think you were funny, or I still know that? Like, it’s so funny. We’re our toughest critics. And we’re the hardest on ourselves. Humor has always been a part of my life. And I’ve always made people laugh. And I, I feel like the energy is my superpower. And so I work really hard to generate energy. You know, I think power plants don’t wake up with energy. They generate it right. And so I work hard on that knowing it’s my superpower. But comedy.

Judi Holler  08:32

You know, I’m not, I’m definitely not a stand-up comedian. But I think I know how to make people laugh. I think I know how to trust myself enough to turn the volume up on the gifts that I have in the things that I see in the world that may be humorous, right? And so it’s been fun for me to use comedy and use humor to help people have more fun, playful conversations about fear. Because why do we allow fear to call the shots? Why do they have to be scary conversations? Why can’t the title of my book be all about befriending fear? That’s what it means to consider it a friend to invite it into your life and sort of throw a party for it because it’s either going to keep you alive, right? Or it can do really good things for us. Or it can point you in a direction maybe you need to go and you know, speaking of books as I was reading your book, I mean, I heard story after story after story of you doing that time and time again, right? Having that playful conversation. You know, okay, here’s what we can’t do. But what can we do? What can we do? And that is the yes and mantra in the Improv Theater that allows me to stay in forwarding momentum. So am I funny? Maybe I just do what feels right. And if I’m not having fun, what’s the point, and when I think we see people be joyful, that that’s kind of contagious. You know, I see so much of your journey. Like there are so many parallels.

Kara Goldin  10:00

To your point, and in my book, I talk about this. But I talk about fear all the time that it’s that what I’ve gained from it. And I learned it early on as an athlete, as a gymnast. And, you know, I learned lots of things like, there would, I’d always want better people on my team because I’d be learning from them. And that’s how we ultimately won. And by having better people, and also just the idea that you’re, you know, you’re going to be good at things. And there are other things that you’re not going to be that great at. And you should just enjoy yourself. And I try and keep learning along. Yeah, you have this section, you know, in your book that really, really why underlined and highlighted because it’s all about the power of the ensemble, one of the things you you train in your company. And this is a great lesson for everyone to remember because Improv Theater is not a nice sport. It’s a wee sport, it’s all about the ensemble I, I cannot improvise alone, I need the ensemble. And I my only job when I am there on stage, and I translate this into my life being here with you on this podcast, when I’m with a client when I’m serving a keynote audience, it is never about me, it is how, how can I make this human being? How can I see them? How can I make them feel incredible? And when I’m on stage as an improviser, my only job is to make them look amazing, which makes me look great. That’s a cool side effect. But when you have in your heart the intention of protecting your ensemble and really looking out for other people. It’s really hard to lose. And is it easy to do? No, but it’s a powerful thing that a lot of people don’t remember, right. It’s not about you, because we never get anywhere alone. So you have a lot of those tenants in your book do the ensemble and how you train your team, you know, how can you make your supervisor? How can you help them? How can you solve a problem? How can you make their life easier? Yeah. And I think it’s also about I mean, call them customers or audience. I mean, they’re all kind of they’re similar in many ways that people have always asked me, What would you? What would you not do? Or I don’t know how you phrase it. But I think for me, just having a feedback loop. And where while some people are really afraid of that, yeah, right, that they’re afraid of going on stage I used, I was always a very social person. But until I actually started doing public speaking, and frankly, I felt like I kept getting asked, especially in building my company hint, being a female entrepreneur there, you know, lots of different opportunities. And finally, I just said, I need to just get over this. And people thought it was ridiculous. Because I was so social. They’re like, of course, you can go do this. And the thing that I realized in my public speaking, that I was, or really my fear was that I read audiences like I’m always really wanting to understand before a keynote. Exactly. Who’s here? Are they entrepreneurs? Are they executives? Are they moms? Are they? You know, what, what’s going on here? Are they college students? Are they you know, who is this that that’s here? And so the problem with that, is that for me to have a deck is very confining. And so when I started to figure that out, then I started being the keynote speaker that I don’t have a deck. Isn’t that great? I love that when I yeah. And so yeah, and so I don’t have a deck, and all of a sudden, it was like, liberating. I don’t know the deck, I’m like I’m, and then I just started trying to bid because people said no, you have to have decks. And then I have actually changed conferences now, who had, like, not been comfortable with the idea that I was not going to do a deck. And then they said, your keynote actually shifted our mind because you’re having a conversation with the audience. And anyway, so for those of you who fear public speaking, check into whether or not it’s the deck situation and how much you want that feedback loop but the audience and, and all that, but I love how humor has played such a critical part of your work because I think its humor is happiness, right? Like for people and especially if you’re the recipients of it and you’re able to allow people to laugh with you laugh at you along the way. I just think it’s something where you leave audiences feeling hopeful. Do you receive a lot of comments back from people as well and emails and It feels great, right? Like to know that you’re actually just by being in front of them, you’re actually helping them understand that. Yes and right that they can go on. That’s, that’s so super, super awesome. So you and I have shared thinking on smashing comfort zones, obviously. Oh, and I’m gonna quote you on this fear isn’t the enemy. Comfort is I’m obsessed with high-performance habits and helping people get more comfortable about being uncomfortable. Can you share a little bit about what you mean by that? Yes, I absolutely can. And I 100% believe

Judi Holler  15:44

fear is not the enemy comfort is and so many people come to our community. We call ourselves fear bosses. This means we’re the boss, not our fear doesn’t mean don’t be don’t get afraid. It doesn’t mean that fear doesn’t exist, but we have chosen, to face it. And so I think we have to first start with the rants on fearless, but I think you and I both agree on I do not believe fearless exists right? There is no feeling there’s some in this great book. Have you read the book Big Magic by Elizabeth Gilbert yet?

Kara Goldin  16:18

I have not. And I love Elizabeth Gilbert. She’s amazing. But I have not read it


on your list. It’s, it’s

Judi Holler  16:26

It is incredible. It’s big magic, subtitle creative living beyond fear. So it’s a really beautiful book on fear and its journey in her life. And she wrote this about it and it was the book I was reading. On my honeymoon, what I came up with the idea for fears my homeboy, so that book forever is like the sort of, you know, ingrained in my heart and in my life, but she said, Listen, the only fearless people I know are five-year-olds and sociopath. So I definitely don’t want to be five. Again, not a good five-year-old, we don’t want to be five and we’re not a sociopath. So the goal should be fearless, it should be figuring out how to fear our fear just a little bit less. So the way we do that in the fear boss community because people come to our community, they read the books, they buy the planner, they go through the course whatever it may be. And they want to be braver, and they want more freedom, and they want to smash those comfort zones. But what they find out they really need and these are the tools we provide. And I bet you’ll agree, they find out they need energy, stamina, focus, competence, and the high-performance habits that are going to get you brave and keep you brave. So the way we do that, in the fear, Boss community is we encourage people, this is our idea on fear, our twist on fear, we encourage people to become fear scientists with us. So this means that we are out there conducting fear experiments on the regular in order to get more comfortable being uncomfortable. So we are putting ourselves in uncomfortable situations to get braver, so those chairs could be really big things right. So maybe it’s a big fear experiment is like quitting your job, getting a divorce, writing a book, starting a company, selling hit water at Whole Foods on the back of your Jeep, right or betting, putting it all on red, right and hoping this works. Those are big ones. But you don’t need to jump out of a plane or free solo a mountain to be brave. You can do small mid-day things. So for the person listening that’s like, oh, how can I work that because its muscle courage is a muscle like creativity is a muscle so you got to use it. And so maybe tonight you cook something new for dinner, maybe you listen to a new Spotify station, maybe you change your hair color, maybe on your next zoom, you go on camera, if that is uncomfortable for you, maybe you start an Instagram account, maybe you send an email to someone new on your team and ask them for a virtual coffee. Big and small things matter but they don’t have to be huge. So we are always encouraging our community to get braver by getting uncomfortable regularly on purpose because comfort is the enemy, not fear. And the more we do this, the braver we get so fear experiments are kind of our little fear. I love it.

Kara Goldin  19:25

I absolutely love it. The other thing I talk about a lot actually is that part of my issue when I was leaving AOL prior to starting hint was I was managing and I didn’t feel like I was learning anymore and I couldn’t articulate why I just was grumpy and you know, I’d start blaming and I don’t know like I would find reasons why it’s someone else’s fault, not mine or you know, very subtly but at the end of the day. What I thought finally came to the conclusion, and it took me a couple of years was that I just wasn’t learning anymore. So a lot of my friends who were intact, and again, I live in the Bay Area, it’s like, all my friends, I’d grown up in tech, but all my friends that I was living by were in tech companies. And I’m starting a beverage company. And they’re like, Okay, I know, you have four kids under the age of six. And you know, Is everything all right? Do you see what I mean? Like, it seems a little off. And I think that the thing that I was so fascinated by in starting this company was that I just didn’t really understand it, right? Like I didn’t, there were so many things, I didn’t know how to create a shelf-stable product, I didn’t know how to do distribution I didn’t. And so I was learning. And so today, I always push on this concept, not only with my team, but also with people who are not quite happy that sometimes by not actually putting yourself in situations where you where you’re a little scared, but also where you’re just where you just have no idea what you’re doing. Those are the places where, ultimately, maybe you’ll fail at some of those things. But other things you’ll figure out along the way. And that’s what I found is really the happiest people, I think, are the people that are learning as humans, I fundamentally believe that we are here to learn, when when we get into situations, where we’re co CEOs, I have friends that are C suite executives that are I’m so jealous of you, you’re out there, you’re learning. And you you know, it’s so exciting. And I’m not that good boys, that right? It’s a choice, right. But I think that that’s the thing. And I’ve talked on college campuses about this, that nobody taught me this. And I think you have learned this on your journey as well. I mean, I’m so excited because we really are speaking the same language on this. But that’s the thing that I think is, is really not focused on in sort of schools along the way where the Mecca is you become a manager, you become, you know, whether you’re in sales or operations or whatever, or and then you become a CEO, and you’re supposed to be really happy. And there’s a lot of people who really aren’t that excited about managing people all day long. They actually want to learn, and, unfortunately, that the second step of that for a lot of C suite executives is okay, well, maybe I’ll go join aboard. But when you join aboard, as I share with people, you don’t necessarily operate, right, you’re not learning in some way, you’re actually teaching. Not a bad thing. But you’re teaching. Right. And so that’s not necessarily going to solve the problem, either. So anyway, it’s something that I think I think about it a lot. And I think that people think that not being afraid, like they don’t fear anything, I think, to your point it just doesn’t exist. Well, maybe you should, maybe you should go find some fear

Judi Holler  23:14

in your life doing wrong, right? I was people come to me, and they’re like, oh, I’m stuck, stuck in a rut in my marriage, in my business in my company with my team and I was my first, my knee jerk reaction care every single time is when was the last time you tried something new. When was the last time you’ve done something for the first time because what happens? It’s easy to do the same things. We the things the same way, we’ve always done that that’s a correlate. So it’s way more terrifying to walk out onto the karaoke stage, the proverbial karaoke stage of life, and pick up that microphone, and belt out your first tone. And you know, it’s something else to your point, I wish they taught me in school. And I learned this in improv. And it was a fundamental game-changer for me. And you have themes of this in your book because it happened to you time and time again, we have a mantra that is no mistakes, only gifts. So we’re either going to go out on that stage, and we’re going to win, or we’re going to go out onto that stage. And we’re going to learn something that didn’t work that we won’t do again. And that set me free. Because now failure shows up. We just had this happen with a product we launched on December 1. There are some things that didn’t go right. And we made some mistakes. Oh, but we learned, and guess what? That gives me the power. It gives us the power to make things better next time to do things differently next time and we put it you know, improvisers live for the plot twist. We don’t run from it. We choose to see possibility and positivity. It doesn’t mean things aren’t going to go wrong. But I control that narrative, no one else right and I can either turn it when you The bottom line is when you are in an environment of Second City where you’re literally going on stage and minutes before you go on your instructor. Your coach is literally tapping everybody in the back going Guys, I want you to go out there and I want you to fail so hard, I want you to bomb I want you to mess this up. And in the corporate and in corporate America Kara I’m being told to like, be myself but not too much or, like, do whatever you want with the PowerPoint, but like, call me first. But in improv, it was so opposite is so it doesn’t mean we don’t follow the rules and be respectful of the things happening inside of our companies. But we now in my company, and in any board that I’m a part of, we throw mistake parties on the regular we celebrate the courage it takes to try something new. We get people into a room with music and cake pops and confetti, masks now and some of that’s virtual, but we literally throw mistake parties, failure parties, whatever you want to call them. I write about it in my book, and that is empowering.

Kara Goldin  25:48

and empowering. Yeah, that is that’s so great. So your book, which is amazing. Everybody needs to purchase it. And it’s called fear as my homeboy how to slay doubt boss up and succeed on your own terms. You talk a lot, obviously about the fear side of things. What what’s your advice for people who are currently kind of feeling stuck? like not being I mean, what step what should they get out there and do tomorrow morning? Yeah, if they’re feeling like they just can’t really move up?

Judi Holler  26:24

Yep, I love this question. And the most tactical, practical, life-changing thing you could do in the next 24 hours, is to conduct your very first fear experiment, to literally do something different to maybe tomorrow, wear a color you’re not used to or take a different drive to the grocery store or go on camera. Like I said, for your zoom call someone that you pick up the phone and call someone versus texting them. You know what I did yesterday, I went on a walk without my phone. And it was amazing.

Kara Goldin  26:55


Judi Holler  26:56

I mean, we don’t, anytime you were doing something just a little get that cavity filled. That’s a big appearance experiment for some of us who hate the dentist. But you get my point mixed it up. If you are in a rut, if you want to start having more playful, more empowering conversations with your fear, you have to choose to have a different relationship with it. And the easiest way to do that is to start playing with it, start dancing with it, start inviting it into your life. So that when it shows up when the real stuff shows up, because real things are gonna happen, like COVID, like a pandemic, like loss of life and business and things are going to happen. We can’t avoid that. But the constant in every scenario is you and how you show up to that. And so far experiments have just been something that’s changed my life. And when I feel stuck, I go out there and mix it up.

Kara Goldin  27:49

I love it. That’s so great. What do you think people fear the most

Judi Holler  27:53

people are so afraid to be seen starting small.

Kara Goldin  27:56


Judi Holler  27:57

People are so afraid to start small and they look at people with these big followings are these best-selling books? And they think Oh my God, who am I? And listen, if you’ve got 25 views on your tv? That’s the classroom? Yeah, a couple of 100 views on your store?

Kara Goldin  28:14

That’s a quote from you. Yeah, that’s Yeah. That’s awesome.

Judi Holler  28:19

We all start with one, we all have that first follower. So that’s number one. And the second one, I’d add, and it’s the one thing you and I, we certainly have a lot of things in common. But failure, people are afraid to fail. And they are afraid of judgment, and they are afraid of other people. And their opinions have been saying and perceived as failure. So we have to remember, and this is a great way to sort of wrapping it up when we are so afraid of what other people are going to think we’re so afraid people aren’t going to like us. We’re so afraid people are gonna judge us. And the cold hard truth is this. And I hate to break it to you. But people already don’t like you. People are already judging you. And they’re already making fun of you. So who are you running your business for who you raise those kids for? who is living your life for you or everybody else? And the final point, and this is one of the mantras that hangs really big in my office. If people are already talking, let’s go give them something to talk about. Let’s change the world. Let’s lead with love. And make sure we’re happy with it at the end of our lives.

Kara Goldin  29:21

I love that. That is so great. And you also have a podcast. Yes. And with Judy Haller. So good. Yeah, you’re gonna be on it. Yeah, we’re

Judi Holler  29:34

doing podcast swap.

Kara Goldin  29:35

I know. It’s super, super great. But I love that and I feel like so many of the guests that you have very similar to what I try and do is not only introduced cool people to my audience but also people who are really authentic and who are just sharing it as it is and this is the I talk about about this a lot these days, I really believe that 2021 I mean, you talked about people don’t want to show their flaws, right? They fear being too small or not having an audience or whatever. I think 2021 is going to be a year where the top leaders, the top authors, the top, you know, the most successful people I put in quotes are the ones that are actually real. And, and, I mean, I think that that is, wow, look, I’m an early adopter on so many things. Like my whole life, I’ve been a little ahead of the curve, which you know, is it sounds great, but it’s actually hard on so many levels, but I really, really believe that 2021 is gonna be a time when people are saying, take me as I am, right, and this is what I’m trying to do. And I’m trying. And I think that that and that is so much what I see and you and everything you’re doing and I am so excited that you came to share with us today. I love Love, love it. So very great. So where do people obviously the book where’s the best place for you for people to

Judi Holler  31:20

get that? Thank you for asking and Instagram’s probably my favorite place to hang out. I’m at Judy Haller, j u di h o Ll er I’m sure will link up in the show notes. And then my website has all kinds of great information. I’ve got a book a workbook, a brand new planner and vibe and thrive Academy Academy that just rolled out so teaching people how to use the science of goal-focused planning in order to thrive in life but also protect their mental health along the way. So we do a lot of work in the mental health area and really proud of that and love to see people continue to be successful. So Instagrams probably my favorite, but my website has all the good information. That’s so great. Okay, great. So

Kara Goldin  32:03

Judy holler at its h o l l. e r Dolla. Yeah. Thank you so much. God, this was so super, super great. So thanks, everybody for tuning in, and like this episode, and subscribe, and all that stuff. And we are here every Monday and Wednesday with all kinds of amazing guests that really make you think and inspire and all that good stuff. So thanks, everybody. Have a great week.