Leap Academy with Ilana Golan - How Case Kenny Turned His Podcast into a Multi-Million Dollar Brand | E121

Episode Date: August 19, 2025

After 12 years of working in corporate advertising, Case Kenny launched a podcast, New Mindset, Who Dis? as a personal experiment. In its first month, the show drew 57,000 downloads, yet Case kept it hidden, afraid it didn’t fit his professional image. Over time, he embraced his vulnerability, created bestselling guided journals, and built a brand helping millions live more optimistic and mindful lives. In this episode, Case joins Ilana to share how a side project turned into a multi-million-dollar portfolio career, why regret is his decision-making compass, and how choosing the right words can change the way you live. Case Kenny is an author, entrepreneur, and host of the globally recognized podcast, New Mindset, Who Dis?. Known for his work in mindfulness and personal growth, he has built a multi-million-dollar brand through writing, guided journals, and speaking engagements. In this episode, Ilana and Case will discuss: (00:00) Introduction (01:42) From Language Studies to Corporate Advertising (05:07) Starting the Podcast Without Clarity (07:43) Overcoming the Fear of Vulnerability (09:04) Stepping Fully into a New Identity (14:14) When Passion Becomes a Business (16:53) COVID, Journals, and a Turning Point in Sales (18:10) Why Journaling Works and How to Start (25:01) Building a Connected Portfolio Career (27:40) Business Challenges and Six-Figure Losses (33:09) Battling Expectations, Regret, and Trust as a Default (42:10) Defining Mindfulness and Advice to Case’s Younger Self Case Kenny is an author, entrepreneur, and host of the globally recognized podcast, New Mindset, Who Dis?, a podcast with tens of millions of downloads. Known for his work in mindfulness and personal growth, he has built a multi-million-dollar brand through writing, guided journals, and speaking engagements. His work has been featured on The Today Show, Good Morning America, Forbes, and NBC. Connect with Case: Case’s Website: casekenny.com Case’s LinkedIn: linkedin.com/in/casekenny/ Case’s Instagram: instagram.com/case.kenny Case’s YouTube: youtube.com/c/CaseKenny Resources Mentioned: Case’s Podcast, New Mindset, Who Dis?:  pod.link/1383599078 The Opposite of Settling by Case Kenny: https://www.amazon.com/Opposite-Settling-Everything-Without-Losing/dp/1401995918 The Soul’s Code by James Hillman: https://www.amazon.com/Souls-Code-James-Hillman/dp/0517271036 That’s Bold of You by Case Kenny: https://www.amazon.com/Thats-Bold-You-Thrive-Vibrant/dp/B0BRDFLJNZ Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Reserve your 24-HOUR PASS today at https://webinar.leapacademy.com/24hr-pass1

Wow, this show is going to be incredible. So buckle up, and I'm sure you're going to enjoy it. But before we get started, I want to ask you for a favor. See, it's really, really important for me to help millions of people elevate their career, fast-track to leadership, land dream rules, jump to entrepreneurship, or create portfolio careers. And this podcast is all about enabling this for millions of people to see a map of what it actually takes for big leaders to reach success. So subscribe and download.

never missed it. Plus, it really, really helps me continue to bring amazing guests. Okay? So, let's dive in. Faith in yourself that you will figure it out is the more overriding masculine quality that reveals itself when you say, I don't know, but I'm going to figure it out. I'm figure it out. Case Kenny is an author, entrepreneur, mindfulness expert, and the host of the very popular podcast, New Mindset. Who's this? There's still days where I don't want to do it. But for me, like, regret is a powerful compass. I remember doing the podcast. And And yeah, it started to get out and trickle out that case has this podcast on the side. And I remember I would always diminish it.

I would always be like, oh, no, no, no, that's just goofy. I'm just playing around and forget about it. I wish I hadn't downplayed it. I wish I had stepped fully into it. What would you say to yourself? Where are some of the things that you wish you'd known? The one that I come back to that's become a little bit of a soundbite that I repeat because I wish I would have told myself this. Case Kenny is an author, entrepreneur, mindfulness expert, and the host of the very popular

podcast, New Mindset, Who's This, with tens of millions of downloads. So how does a corporate guy leave everything and jumps to be the mindfulness guy? Stay tuned. It's going to be in a fascinating. fascinating, fascinating episode. I'm really excited for it. Case. Thanks for being here. Thanks for having me. I'm excited to chat. So take me back in time. You grew up in Chicago. Was there a moment in time where kind of shaped you as an entrepreneur, as a mindfulness person, like that you are today? Well, there's a couple different things for sure. I would say the first is on the more

material front of like what I do, entrepreneurally, but like the substance of it is I've always had a very intense draw to languages. And it only makes sense now at 37 and many career shifts later of why that's the case. Like even in high school, I was always really good at Latin. I took five years of Latin, took like AP Latin. I don't know if they still teach Latin anymore. Anyway, I was always like strangely good at it and was like one of like four people in those classes. And then I went to Notre Dame and I majored in Chinese and Arabic because I was drawn to it. And I frankly wasn't like smart at other. I tried premed because my brother's a doctor. and I just like, this is not for me. I took accounting. I was like, it's not for me. So I was always

drawn to those things. Pause. And then after I graduated, I went into advertising. It was 2011 still somewhat of a tough job market and, you know, I was struggling to get a job as a Chinese major. And I ended up getting a job in advertising technology, strategy for Procter & Gamble and at an agency in Chicago. And it was great. And that led to a 12. year career in advertising. Eventually, I worked in advertising technology sales, worked my way up from account executive to a regional vice president. I mentioned all that as background for now being someone who I say, I share my feelings for a living. That's what I do creatively. It's what I do entrepreneurally. It's all about language and human emotion. And now it makes sense about how those

things came to be. But I think, to answer your question, I mean, I think sales in particular is what led me down the entrepreneurial path. I never, I wasn't like a lemonade stand kid. I never like really had a huge entrepreneurial drive, but sales will will really make you realize what you're capable of, how you could literally start at zero and build something huge, how you could evangelize for a product and maybe even build one better yourself. And so it, it really opens your eyes. And I think that's what really enabled me at a certain point because I, the short version of it is I started my podcast when I was amidst that career, because I was trying to know myself better. Wait, wait, wait, I don't want to go, don't go there.

We're going to go there slowly, slowly. Okay. Because I think your shifts are actually incredible, but I agree with you on sales. And I think this is actually a really important distinction because I think even when people really love a certain thing, like you may love mindfulness, et cetera, they don't realize that they actually going to put a lot of hats on, especially in entrepreneurship. Like, you're going to be also the salesperson and the marketing person. And so you can love, you know, a certain thing, but eventually you put different hats on.

And if you actually have the sales background, that's incredible. I mean, I talk to a lot of younger people and they're like, oh, I want to do what you do. And I support anyone who has the drive to do something like this. But it really becomes a conversation of, okay, well, are you willing to write every day? Are you willing to promote every day? Are you willing to market every day? Are you willing to keep an update P&L every day? Are you willing to pay your estimated taxes on time once a quarter?

like the things that you think you escape would you do turn into a creative or entrepreneurial endeavor certainly are there to your point and so take me there so you have this comfortable career it pays the bills was there a moment that you're saying you know what i need more than this was there like a certain thing that attached you to like what what made you do such a shift well i think it was a couple things i mean i so i started the podcast while i was working the job and i and i started to build a business while I was working the job. And it gave me some fulfillment, right? Because it wasn't like I was drained at my job necessarily. To my point, I think it was an incredibly powerful evangelizing part of my life and taught me so much about myself. But I was missing the clarity personally. And then I was

also missing, I think, some of the fulfillment of being my own boss and, you know, steering the ship in the direction I wanted. So starting the podcast, starting to write, started to create some products while I was working that job really started to give me the you know some of that that that itch and I was scratching that itch and it was great but tell me tell me I'm taking you slower and for a reason like our audience want the same thing that you did but they don't know how to take the first step so there's a reason why I'm slowing you there because because even to create that podcast when you're not sure what it is that you want especially clarity clarity is something that we're seeing in Leap Academy I think probably about 80% of the client that come in have no clue what they want to do next and deciding what they want is probably one of the hardest thing and making that jump when it's not a thousand percent clear that this is what they want to be known for is actually really scary so how did you start like how did you start doing that podcast yeah well i think that's an important context too because i think people put a lot of pressure on themselves to want to find the thing that will define them and put a label on it as

quickly as possible that was never my intention like i started the podcast because I wanted to know myself better and I was like, well, I can't just read another self-help book and listen to someone else's podcast and call it a day. I was like, that's my frustration because I was so sure in my career about what to do to be successful. But as a person, I was like, I don't have that clarity. So I need to figure this out. So it was a very self-centered in a good way endeavor. And I was like, I will figure it out. I never set out to be a professional podcaster. I never set out to be a writer full time. Never. It was not even on my radar, frankly. So tell me about the first episode like I want to hear like that first episode what do you even talk about I wonder I wonder what

I did frankly I would probably honestly well I know in the first five I do remember talking about like confidence and like how I was developing confidence and then how I would encourage other people it was like well if I can describe my experience and then share that back simply maybe that maybe that shows that I explain it that makes a lot of sense because I was feeling unconfident in various areas of life and And I think I turned around and would share that from an eye perspective. How did it not scare you? How did it not scare you to be so vulnerable? No, it sure did.

I mean, I even remember, like, to my recollection of cringe being like, I was really good at sales and you can make a lot of money in sales. And it's very like, bling, bling and who you know and all that kind of stuff. And I remember doing the podcast. And, yeah, it started to get out and trickle out. That case has this podcast on the side. And I remember I would always diminish it. I would always be like, oh, no, no, no, that's just goofy. I'm just playing around and forget about it.

Whereas it was important to me. It wasn't important professionally yet, but it was important of why I was doing it. But I would always downplay it to protect myself because it was a vulnerable thing. It was a vulnerable thing emotionally, creatively, but also professionally. It was the opposite of what my career represented, which was put on your business casual, go close the deal, collect your commission, take clients out and entertain them and swipe the MX. And it was the opposite of that. So I think, you know, I wish I hadn't downplayed it. I wish I had stepped fully into it. But at a certain point, after I'd been doing it for a while, 50 episodes, 60 episodes, and I was like, wow, people are actually listening to it. I remember my first month of the podcast, I got 57,000 downloads, which is a lot in podcasting land, especially for a first time podcaster with no real, like, social presence. I was like, wow, okay, so some people are caring. And at a certain point, I was like, no, I'm going to step into this. And that's when I adopted the moniker of Case is someone who shares his feelings for a living. And I was like, I'm just going to go hyperbole. If I've been afraid of owning this thing, what would be the pendulum swing all away to the other

side? Case shares his feelings for a living. So I think that really helped me, like, ownership-wise. And then it became the funniest thing, too. Like, I would go into client meetings. And people were like, oh, your case, I listened to your podcast. I was like, well, that's freaking cool. Our worlds are colliding. Maybe this isn't something I should hide in my closet after work and do. like it became something I was more proud of and then obviously you know things happened after that but like that shift emotionally was was big and that's huge like and again like kudos to you like I think there's like that first step is usually the hardest thing and I think there's also an element like when you don't have a full clarity of what it is that you want to do first of all everybody wants

to check all the boxes right they want the full confidence like I know exactly where I'm going and that's not how it goes the thing is that being vulnerable When it's still, there's a little bit of a wound, like, it's really, really scary. It's easier to be vulnerable from a scar. So how did that open up for you? Like, was there moments of like, am I kidding me? Like, am I doing the right thing? Oh, my gosh. Yeah. I mean, I still have those every day. I mean, I think one of the great checks and balances in wellness professionally and personally is like, how humble has your work made you become? Like, especially in wellness. That is people who give life advice or suggest reflection prompts and like, these things. Like, the ultimate way to see if someone is doing the work is how humble have they become as a result of their work? Hopefully so, it's unearthed the fact that they don't know a whole lot. And to me, not to sound noble, but I'm very much in that space. The more that I do this thing, mindfulness certainly is a muscle. I've done hundreds of podcast episodes, thousands of books and pages. Like, if anything, it's just made me realize how much I don't know, which is a beautiful thing,

though. That is a beautiful thing. It has shown me the space that I can fill with clarity and then introduced another space that I could do that with. It's shown me the beauty of in-between moments and transitional phases in life. And to me, that's not an insecurity that you need to cover up with bravado or charisma or ego. It's like a beautiful, beautiful space. And in that sense, it's become easier to be like, I don't know the answer, but I'm going to talk about what I think might help me find out the answer. And creating from that place and also creating expertise. from that place, I think is what the world perhaps needs. It's what I need, at least, as opposed to here's the rules, here's things, the ability to reinvent yourself, like leaning on that as

opposing to want to have a static identity and figure it out and own it. To me, I think that only is that the gift of life, but it's a requirement of entrepreneurship and, you know, being a creative professional as well. And it again, I think there's an element of for driven people to admit that they don't know or, you know, they don't have all the answers is not simple. And maybe I'll say something, I don't want to take it in the wrong way, but I feel like for men, it's almost even harder to admit that they don't know. Am I right? Is there? No, yeah, because I think certainty and confidence are inherent masculine qualities, as they should be, I suppose, but I think humility amongst that, that is faith in yourself that you will figure it out, is the more overriding

masculine quality that reveals itself when you say, I don't know, but I'm going to figure it out. I'm going to figure it out. So I think that's a higher energy state to operate from. Amazing. So was there a moment that kind of like hard moment that, you know, shaped you? Or was it a slow thing that you wanted to do? How does that happen? I mean, no, I think, I think like many things, it's a slow burn, right? You know, it's, you know, for me, I was the frustration perhaps of not knowing myself. It was compounded by unfair self-judgment, pressure to be a certain person, a certain way. I think if you go deeper and deeper into therapy time, there was probably a reflection of just emotional lack of emotional self-sufficiency, my relationship with emotions. So I think

all those things combined. But I mean, I'm lucky to have a somewhat type A mentality where I was like I have this mess of confusion. I need to do something about it. Luckily, that's the way I'm wired versus creating an identity from the confusion. So I think, you know, that pushed me to start. And then that led me, I mean, I've changed course so many times since then. But I think the evolution came from just like that place of frustration. So you start entrepreneurship. Do you understand that you're starting entrepreneurship? Or again, at that point, I know that you're kind of doing the podcast on the side and you're starting to write. But do you understand that this is starting to be a whole journey?

And when do you actually leave everything and say, okay, this is my time to go all in? Because at that point, you didn't have 1.3 million followers or whatever and tens of millions of listeners. I think sometimes we compare our beginning to someone else's success. Well, I think lucky for me, again, you talk about having a why and having the why drive your business and have it be what makes a business sustainable. I never intended to make any money or a career from it. So I did 200 episodes before I was even like, oh, wait a minute, maybe there is a professional future here. So truly. So I think that was really helpful for me.

But then, you know, I also am somewhat contrarian. And, you know, luckily I worked in advertising. So, like, I had a pretty good understanding of marketing, products, e-commerce, creator economy. And I was like, okay, well, people are listening to the podcast. People are starting to care about what I have to say. I was like, well, everyone is like, oh, you should start doing brand deals and make money from sponsors. And I was like that feels like, it feels like a low leverage game to get involved in, right? And it is a fine business model.

It will get me wrong, but it is part of a larger wheel. So at the time, I was like, okay, well, I'm not in a rush to do this necessarily. I have this other job. Let me think about how I could build something, entrepreneurially, a business, instead of just doing what's obvious. You have impressions, monetize the impression. And so I was like, what can I build for people who are interested in what I have to say? And I landed on these guided journals because a lot of my work is around written reflection. And at the time in 2018, I went out and bought a bunch of journals.

And I was like, none of these speak to me. These all stress me out. The journals were like, do this, do that. Come back later and hold yourself. I was like, man, this is not clarity. This is pressure. And that was at the time. Frankly, at the time in 2018, there weren't that many guided journals.

as crazy as a thought that as that sounds um so i was like oh maybe i will create my own so i spent a year just developing my own style of journaling that was a mix of just like clarity and repetition and i was like let's see how this goes and i did an indigogo kickstarter campaign for it and frankly it didn't do that well it raised how much did it raised i think it was 37 000 which is fine of course But, like, I wanted, like, hundreds of thousands of dollars. So, and the way I worked with Indigo is people back it before, and then you send out the, send it out. So I used the money to, I worked with a printer in Canada, designer, a warehouse, a 3PL company that shipped them out. It was all very one-to-one.

It wasn't, like, print on demand or a publisher or anything. It was a literal printer in Canada who I sent the files to, they would print it in bulk. So I ordered, like, it was like 3,000 journals. The campaign ended. I sent out the journals to everyone. who ordered them and then I was left with like a thousand because I was in the whole money at this point. And then COVID hit. This is the COVID timing. And so I just had a lot of time in my apartment in Chicago because I was no longer able to travel for work because I managed a team

in the Midwest and managed the whole region. And like we couldn't go and travel, which is a big part of our work. So I was like twiddling my thumbs. So I was like, well, I've got all these journals in a warehouse in Cicero, Illinois. How do I get rid of these things? So they're not burning a hole in my wallet. So I just literally just started to post them on Instagram. And at that time, I think I had like 20,000 followers. And I don't know, just something happened. I remember at the time I had my Shopify notifications on my phone and it would go ping, ping. I was like, what? This is crazy. It was like a very baffling moment, frankly, because again, I wasn't entrepreneur e-commerce guy. But frankly, the rest is history from there. I'm happy to go into more detail. But eventually that

that turned into my life's work before moving more into like book and traditionally published books. But yeah, it was, it was that moment during COVID. And then between 2020 and 2022, I created three more skews of different journals. And I sold like a little close to 300,000 individual units of them. So it blew up. Incredible. And I will want to go there a little deeper. What did journaling specifically unlock in you that you felt like this should be a tool that you want to stand behind. Yeah, well, my world, the world's favorite question for me, because my whole life's work now, I do them for corporate, I do them,

my own events is taking people through basically guided general prompts. Well, I think it accomplishes a couple things, not only taking advantage of the neuroscience of mind and body, but also just the essence of what happens when you sit down and you choose your words carefully, like when you choose 14, 16, 20 words to describe something. It taps into what I think is the essence of mindful practice, which is mindfulness isn't just listening to yourself. I think we're in an amazing age

where we're encouraged to sit still and feel and feel and surrender to your feelings and be non-judgmental of them. Yes, it's an amazing practice. But I think a lot of us skip the second step, which journaling helps bring to light, which is mindfulness is listening to yourself, but mindfulness is also perhaps most importantly,

at least in my world, it's talking to yourself. How do you talk to yourself about the feelings? Specifically, as practical as I could be, what are the words you use to describe your feelings? Not someone else's word. Not anxious because someone else uses that word. Not unlovable because that's a social media word. Not narcissists, not this, not that what are the words that actually resonate with you? How do we honor our feelings? But then how do we create movement such that we could be optimistic in life? So for me, journaling is the ultimate conduit, not only to self-reflect and become self-aware, but it's frankly like the only way to truly become optimistic in life. That is, the words you use to describe your feelings dictate. the way you experience them out in the world. So journaling and sitting down, and I would create these 60-day journals, journaling for 10 minutes a day

in response to certain prompts, is how you actually create an internal vocabulary that is you, not someone else's, but yours. And yeah, it's something I love, and it makes sense to my opening about language, right? Chinese and Arabic and Hindi and Urdu and Latin, these languages that I've studied and the energy of language and bringing that to life in a product. And people with a pen in their hand, I think, is a superpower. And if you could tap into it, I think the only people that are really into internal dialogues nowadays are like athletes. Athletes are very much encouraged to think about how they speak to themselves in light of performance issues. The average person is told to reflect and be

honest with themselves and feel what they feel. But there's not a whole lot out there as far as training and guiding about word choice, emotional vocabulary. And that's what I love to do. incredible so for somebody um before we we go on for somebody that never journaled doesn't even know if it's not a waste of time sorry like you know like just kind of like just doesn't even like why on earth do I need to I mean I'm a grown up person like what do I like you know journaling is for kids like tell me a little bit like how do you even get started how do you even start believing in this well I understand that first of all because I think that's how I felt in my 20s like oh a journal is a diary a diary is for sad people right it's kind of a common assumption or something i don't

know that comes from a place of immaturity but uh i understand that a little bit of cynicism i mean i think the only way you'll break free of that is to try and you know i think it comes down to like the journal you get the questions you answer because if you adopt a form of journaling where it's like write three things you're grateful for write three things you want to do today that's not journaling that is that is a to-do list that is productivity that is reminders and you know I talk about gratitude about how to truly journal for gratitude I talk about other other different prompts that happen to emotions everything that I view is through the lens of contrast that is find the contrast in your life that makes you uncomfortable the transition between full-time job and

full-time entrepreneur the transition between being single and being in a relationship the transition between being insecure and having confidence that is the area we have to evaluate Just writing down things you want to be true in fantasizing about future days is not, is not, I mean, it's great, but it's not going to, it's not going to open up any breakthroughs for you. So it really is about the prompts that you give yourself, whether it's from a prompt that I've created or your own. And then it's also training that muscle. Like a big part of the work of journaling aligns with a lot of therapeutic approaches, which is how do we unblend parts of ourselves? because we are complex humans. There are many parts to us, right?

We're not just one blob of identity. There's parts from the past that are trying to keep us safe. There's parts in the future that are trying to make us productive. These parts are all competing for harmony within us. And then there's the self, which is the divine, the honest, the bold. And it's our job to restore harmony amongst all those. And the easiest way to do that is with the way you speak to yourself, such that when you have a feeling, you don't say, I am anxious. the worst way to describe your feelings and you also don't say i feel anxious the second worst way

the best way is to say a part of me feels anxious we honor the feeling but and then we do the creative and reflective work to be able to fill in that blank a part of me feels anxious but and then we we fill in that blank with something that speaks to our ability and that is how i approach journaling so it's reflection we're honoring it we're not sweeping it under the rug but we're creating space for movement with our emotions and our capacity for change. Right, right. That's strong. I get what the difference is because I think I was more looking at a to-do list.

You're right. And I think the beautiful thing is that we do see, I mean, some of our clients definitely journal. And what I love about it, what you just said is that we're probably the worst friend of ourselves. Right. Like the way we talk to ourselves is something we never talk to anybody, even our worst enemy. Right, right. And I think that's another element that, you know, just stop to think about how you're actually talking to yourself. I think is also a really big part of something that, again, will enable you to create the possibilities that you want to create for yourself.

So if you're feeling stuck, underpaid or unappreciated, or you're simply ready to take your career in life to the next level, I have the perfect solution for you. We have a program that helps you fast track and leap your reputation and career. Become the best version of yourself. Get the dream role you deserve, move up to leadership, jump to entrepreneurship, or even build a portfolio career. This program helps hundreds a year, and it will help you gain the income, influence, and impact that will transform the second part of your life.

Watch our free training today at leapacademy.com slash free hyphen training. The link is in the show notes. Now back to the show. But tell me, again, like, I think many of our listeners, one of the hardest thing for them is to maintain, like they want to create this multiple facet career, portfolio career, what we call, multiple streams of income. And you're kind of living, dreaming that, right?

Like, you're journaling and books, and we'll talk about it in a podcast. Like, you have this, like, multiple, facet things that you created for yourself, how did, did you have a vision of what this going to be? Or, you know, every time you opened up something, it created something else and you just kind of leaped into the next thing. How do you think of it? Well, I think of it as all connected. I think it's a difficult thing if you want to be multifaceted and none of it's connected. That's very difficult to have seven different businesses that do not intertwine and do not

gain efficiency because of their interconnectedness. I can't imagine trying to run seven different business models that the only tie is your holding company or something like that. That seems very difficult. For me, it's like the podcast is the center of my universe. It's where I get all of my ideas. It's where I get all of my content. It's also the center for promotional efforts. But it's very simple for me now. I do the podcast. I do it twice a week. I've done 730 episodes. I've done it for seven years, three years with Series XM. I do the podcast. because it's monetizable, but it also gives me ideas. Then the ideas that work, I'll put on social media.

Then the post that do well, I'll turn into a book. And then the book that does well, I'll create event series around it. And then the ones that really do well, I'll develop a product around it. And the ones that I really like, I'll go and work with a brand and we'll put on an event. We'll do an exclusive series together. So it's all connected. For me, the podcast is the center of the universe. And it's not difficult then to add a spoke to it, whether that's my speaking and my event.

whether that's my traditionally published books with like a penguin random house or a hay house, then it's my brand deals where I'm leveraging expertise, right? So I don't sell influence to brands. I sell expertise to brands that's created on the podcast. Then it's investments in consulting with different groups that I angel invest in and I consult with. And then it's individual, if I want to create a skew that I own, it'll come from that. So to me, it's just like it's just the wheel and spokes. and it ends very simple.

And I think it requires you then hedging your bets a little bit on one thing and saying, this is going to be the thing from which everything else will come. And I, you know, don't necessarily have a blueprint for that. But I think if you could figure that out, the multifacetedness will come much simpler because it flows together. Right. And I love that because, again, when we teach portfolio career, we always say you have to have one thing that is relatively stable and the rest create kind of more of a, you know,

snowball effect versus throw spaghetti on the wall and, you know, see what sticks. And I love that, you know, this is exactly what you've done. But I do want you to talk about maybe some challenging moments because, again, it's not easy to record 700, whatever you said. You know, I looked it up, but, you know, like episodes. Like it's not, it's like, and there's challenges, there's hate. There's like, there's, you know, things will come your way. Share maybe a moment or two that were, oh my God, this is hard. Well, yeah, I can give you multiple. I mean, I haven't shared at least two very large business flops that I tried to make spokes of that did not work and that were six-figure losses, no problem. I mean, I think the biggest first challenge I came across when I was scaling the journal business, you know, that, and again, to my point in 2020, it started to do well, I started to create these other skews, I created systems and business around it.

I had people working for me. We were doing paid ads. We were doing all the analytics. it was a full-fledged business stripping out, you know, several tens of thousands of journals a month. And a big part of that was our ability to scale

of paid ads. But then in, when was it, in 2022, 2021, somewhere in there, Apple passed a bunch of new privacy policies and it completely changed paid advertising for small businesses that relied on performance marketing. And I certainly was a victim of that. And it changed everything very quickly,

very, very quickly. Because I had a lot of inventory you would make money you would buy future inventory you would make money you would buy future inventory you put a little way for yourself but it's all reinvested and that was based on your ability to forecast how you can scale organic and paid and the whole thing and then when paid goes away and you're sitting on 100,000 journals in a warehouse suddenly the bills add up and that was a big one and you know it's somewhat of a blessing in disguise because it shifted me away a little bit from that model and more to what I'm doing now which is an amazing model.

which is my traditionally published books where I don't have any upfront cost, but the promotional strategies are the same, but there's much more upside on a branding perspective and your ability to get your books in retail and a bunch of things that weren't available to me previously. But to answer your question, I remember that one occasion quite specifically when the wheel just stopped spinning at the rate it had, and a lot of people face the same challenges. And a lot of people overcame it and figured it out for me. it was assigned to, you know, pivot a bit and to diversify a bit. And, yeah, and here we are now.

And you are coming out with the opposite of settling, which I wanted to talk a little bit about it, but it's basically, you know, very aligned with where our clients in Leap Academy, like how do you get, you know, like how do you get that spark or how do you, right? So talk to a little bit about it. How do you get everything you want, right? Every single thing. There is a large dating component to it, but I won't reference that because the core of the book is about recognizing your spark and realizing that that's the thing that needs to see the light of day in your career, in your arts, and in your relationships. But, you know, I talk a lot about, and I borrow from the work of James Hillman, who wrote a book called The Souls Code, which is basically the idea that we all have something in us, our essence.

and it's something special, even though that is a cliche, I think there is something special about everyone, maybe not overtly so, but we all have a special balance of emotions and capacities that mixture of them makes it special. And we could spend a lot of our life burying it, preferring to be normal, preferring to follow a path, preferring to date and work in certain ways. But that thing inside of us needs to see the light of day. And we'll realize that eventually, likely looking back, or we can realize it today. And the example in the book is that, you know, you, we all have this acorn inside of us and we can plant that acorn in a field and water it and we can hope that it will become a banana tree because we've been told we need bananas but it's going to it's going to become an

oak tree it has to be an oak tree there's only one thing and there obviously is an element of life of being adaptable and you know reinventing yourself but there is something about us that spark that piece of pizzazz that needs to see the light of day in our in our work in our personal lives in our romantic relationships and figuring out what that is can take a long time. And I don't necessarily think we should put pressure on ourselves to be 22 and be like, this is the thing. But I think it's our work and our duty to listen to it and try to figure out what it is and try to bring it to life in many different ways. And yeah, that's basically what the book's about, how to do that mindfully, how to use certain psychological ideas to your advantage and just make sure you

to look back without regret in regard to your essence and your spark. And I love that. And we'll have the links here to pre-order. But I think one of the, you know, I think a lot of our people are trying to find. And, you know, in Leap, we help them find that zone of genius, what I call. But it's like, you know, that is the special sauce. It's kind of that spark, right? But also it's a lot. And this is where I want to tap with you a little bit, case because I think a lot of it is based on society expects us to want certain things or society or parents or, you know, a lot of it is sometimes dictated by external things and how do you battle the external things and what people expect you to say or do versus what you truly want, right?

Like when I moved from being this business person and investor, et cetera, to start Leap Academy, I was like, what? You want to be a coach? You know, it's like, yeah, well, I want to change people's lives and I want to change thousands of lives and I'm actually a business person, but this is, you know, but I think it was the hardest thing was to recognize that I'm going to go against what is cool. Yeah. How do you do that?

I think a couple of different things. I mean, I wrote a book two years ago called That's Bold of You where I talked about conformity and like why we conform and in general, in general, in general. Now with social media and AI, who knows what they actually. answer is. But in general, we conform because we don't want to be the odd man out, alienation, or two, we have rationalized that because everyone else is doing something, that that clearly is the way forward. It clearly has a group of followers and people are doing it. So clearly success lies on the other side of that. So I've always thought that was an interesting observation.

In my new book, though, I also talk about nonconformity as a character trait, right? So maybe in light of I don't want to be the one who's the odd man out, this applies in all scenarios. And the book, I talk about it in terms of romantic attraction, but overwhelmingly so research shows that non-conforming traits are attractive, non-conforming. So being slightly different, being weird, being passionate, being intense, the spark. We always think that that's the wrongness about us, whereas overwhelmingly so, it's show that it is the attractor. And yes, it will turn off the wrong people, but it will attract the right people. So I mean, I'm not so sure I have an exact answer, other than leaning into perhaps some of the observations that say the thing about you that makes

you think different or act different, that is the thing that you need to follow, not only because maybe it is attracted to the right people, and it's important to surround yourself with the right people. But also, like, there's a lot of interesting research that shows that, like, success doesn't come from quantitative measurements. It comes from qualitative differences, right? There was this researcher who followed a bunch of swimmers across various degrees from high school to college D1 to Olympic champions, and he followed them for a long time to see, what? is the difference between a high school swimmer, a D1 swimmer, an average swimmer, and an Olympic champion. And he found that it wasn't quantitative. He found, and it's a crazy headline,

he found that Olympic champions didn't train more than the average swimmer. They trained differently. So it was a huge qualitative difference about them, not necessarily just an hours in doing the thing. And obviously there's incredible nuance there with that study, but it was, how can you do something differently? So all in all, non-conforming traits being attractive, moving differently, being the thing that helps you break through. To me, the answer is somewhat simple, then, of at least you have to try and see where it leads you. And that's true. I mean, eventually, I think when you talk about, you know, in my podcast, I remember, you know, you kind of look at, you know, the biggest leaders of our time.

And there's like, probably if I need to sum up the podcast, usually it's, I don't know, grit or tenacity or, you know, like, it's probably like it's going to sum it up. But let's talk about that for a second because, again, like, going through the motions and, you know, you shared one challenge. But, you know, sometimes, like, I don't feel like doing a podcast today. Like, I don't know if it moves the needle. Like, did you get any doubt? Did you get any hate? Where did that catch you? Yeah, I mean, all the time. I still, there's still days where I don't want to do it, right? You got to be in the right headspace to do this kind of work, right? Because it is a little bit softer than working in Excel or stocking a warehouse or moving a skew, right? inherently soft. I feel that a lot. I don't know. I mean, maybe I'm different. Maybe not everyone responds to this as a catalyst. But for me, like regret is a powerful compass. I think all the time, like, it's a compass, right? It's not something I should be averse to. And it's the simplest question of like, would I regret not doing this today? And the answer is usually always yes. And then I do the thing and then I feel good. And in fact, I did an episode recently on

using regret as a emotional framework encompass to make decisions makes you more optimistic. Like it has this interesting trickle-down effect that researchers have shown where they had these two groups of people making decisions, small decisions, big decisions. They had one group say, hey, before you make the decision, I want you to think about regret. Will you regret doing or not doing this decision? The other group, they said, hey, what's your decision? And they showed overwhelmingly so that through whatever ways that they measured it, that the group that used regret to make the decision, after them made the decision,

they were way more calm, peaceful, and optimistic because they're like, well, I did the reflection and I did the thing, what else can I do? There's nothing else to overthink. So I'm, I'm, feeling good about this. I feel hopeful about it. And not that that will necessarily create the outcome you want, but I want to live with the clarity knowing that I made the right choice and I trusted that I'll deal with whatever happens afterwards. So that's typically how I operate with the idea of regret as a compass, do the thing, and then don't overthink the thing. And then move on to the next I love that you said that. And actually we had Daniel Pink on the podcast and he has a book about regret. And he actually says people will almost always regret more the things that they didn't do

versus the things that they did do. I'm sure. I'm sure that's true, right? Which is so interesting. Yes. But having like a whole statistics about it is just incredible. So I love that you said that because I don't think I've used that as a tool in the way that you shared. But it's absolutely a motivational. It's absolutely the motivator. I'll give you another one too that it was a really big catalyst for me in all areas of life, but it started in corporate. There was these group of researchers that followed these workers in corporate jobs over a long period of time. And they basically divided them into two groups of their mindsets. The first group was filled with people who they were the, it's a dog eat dog world out there. You got to step over some people to be successful. Watch out for yourself. Watch your back. It's all about. you. You got to do what you've got to do. That was group one. The other group was people who the mindset was they may trust their default. They trusted that you and I can both be successful. There's enough promotions to go around that if you say you're going to do something, I trust that you're going to do it. Trust is your default. And they showed overwhelmingly so that the trust

is your default group made significantly more of the course of their career, was promoted much more frequently and was happier and more positive. I always thought that that was a pretty interesting thing. Make trust your default. And that's not, it's not just trust in other people. It's trust in the industry. It's trust in your sector. It's trust in yourself. I think it's interesting. Make trust your default and just, I don't know, perhaps it'll lead you in the right direction. And perhaps it'll make you less resentful and perhaps it'll make you more trusting and perhaps it'll bring better people into your life. And that is what will make you more money. It's a trickle-down effect of that emotion. So make trust your default. I love that. And I love that. And I

I think Gary V said say yes to the maybe, which is also kind of like an interesting trust factor because it's all about what you said, Case, it's about trusting yourself at the end of the day because you're the only one who needs to eventually show up again and again, despite the fear, despite the pain, despite everything, you're going to be the person that needs to show up. Yeah. I mean, when you go into the millions that you have right now, Case, there will be hate. Did you feel like you needed to create some thick skin for yourself somehow? Or not really? In a sense, yes and no. I mean, I am lucky in that people very much support me. And I tend to occupy a space to the internet that I refer to as hope core. Right. So it's not political. It's not lifestyle. It is sharing optimism and helping people feel seen. And the majority of people accept that. A lot of people are in hurt spaces. And when I remind them of something good that they don't have, there is a certain visceral reaction to it. And some people will.

will lash out at me and, you know, say that I don't understand and I'm wrong and I'm privileged and this, that and the other. And I think, you know, in light, in lieu of developing thick skin, it's more of developing a pause so I don't respond to those type of people. Because everything inside of me when someone attacks me is to defend myself. And I think that is what I have developed because, you know, I try to practice what I preach. And that's self-awareness. And to realize that I can say something that someone else does not believe to be true. And I need to accept that fact. There's still that part of me that wants to defend myself. And I think letting go of that is beautiful. And I very rarely respond to anyone. But anytime I do, it's really funny. Sometimes I'll have a lapse in

judgment and I'll respond to someone who lashes out at me. And, you know, someone will DM me. They'll be like, F you or something. And I'll respond and I'll just be like, hey, you know, something nice. Like, I hope you have a better day or something. I probably shouldn't respond. But So anytime I ever do that, I usually get a DM back a week later, a day later, and the person says, hey, sorry, I was just going through a lot. You know, it wasn't personal. It's true. It's not like I'm fishing for that as an answer, but it is an interesting observation in light of why people lash out. Usually has nothing to do with me. It has everything to do with them. That's true. Of course. But we need to, you know, get over our instinct to like, let's bash this. Yeah, there's power and pausing. And yeah, so you just close the app up, move along with. with your day. I love it. So if somebody doesn't really know anything about mindfulness, anything about what you do, what are some things that you want them to know? I alluded to it earlier, but I mean, I think there's many beautiful ways to celebrate mindfulness and mindful habits from meditation to therapy to breathwork to just grounding yourself to sound. There's, I mean,

there's so many modalities nowadays. So don't feel the need to be like, this is mindfulness and this is not mindfulness. The mindfulness that I gravitate towards is, is all about your emotional vocabulary and how you listen to yourself and how you speak to yourself. And to me, that's the most practical form. So maybe start there. If you're, if you're someone who is a little averse and, you know, you're a little cynical of like the woo-woo, that's fine. That's fine. Maybe start with me. Come on, come on over here. The water is warm. Let's start with words. You know words. We know words. Start here. And then if that opens you up, then maybe we could talk a little bit about some visualizations and some belief frameworks. And

a little bit we could throw in some words like abundance and we could start talking about the you know some of the more spiritual elements or you could stick around and just do do the words think about the words think about the language think about how can you and think about like the direction like to me it's not like i want to sit down and practice mindfulness it's i want to sit down and i want to feel at peace with what i'm feeling and i want to do that because i want to be hopeful i don't want to be burdened by my emotions i want to be optimistic that's a good motivation that's the motivation that inspires me to do the work so maybe it's like think about what is not necessarily like what are you trying to accomplish that's not like outcome oriented but like what is

the direction you want to go what is the way you want to feel and then let's work into something that will make you feel that way it could be a mix of different practices it could be one practice done every single day totally up to you and that's the beauty of it you know it's interesting case because if you would have catch me or caught me I don't know like a decade ago I was in corporate, I would totally roll up my eyes. Like anything mine, you know, related thing, you know, I was just like, this is BS. I don't believe in it. Like, you either do it or you don't do it and that is it. And I think you alluded to it a little bit, the more you learn or the more you progress, the more you understand how much you don't know. And I think this is exactly where,

you know, it actually blindsided me completely because the first time I wanted to start Leap Academy, me, the truth is I didn't miss the strategy. I thought that it was like I kept blaming people. I don't have the strategy. I don't have the strategy. It wasn't the strategy. The fear was numbing. It was all my mindset, right?

Like all I needed to do and say, I'm going to write this post because this is what I want to do now. And the fear was just overwhelming. And it is all mindset. It's all, you know, so I think it was interesting to see even my pattern around what you're just sharing. And if somebody's rolling up their eyes, like I would just want to say, I hear you. And it's incredible how much I didn't know. Yeah. And I see it a lot, too. Like, I'm lucky. I basically speak for a living. And I do these, I call them mantra where I come in and I basically do these guided reflection sessions. I do them for the NFL. So I do them for a room through a 300 men who hit each other for a living. I do them for corporate groups all the time. I did one in New York the other day for a PR firm that was 70 women. It was all women, not a man in sight. I do them for realty groups.

I do them for all different types of sectors from all men to women to everything in between. And, you know, I'm not drinking my own Kool-Aid to think I'm like the miracle maker, but every single time it is engaging for these people because it just, it allows people to interact with their emotions in a way that they haven't before. And I just, I always see some type of, of breakthrough. So I think a lot of it sometimes is like, we are averse to the things that we, haven't tried and I understand that. That was certainly me, but it's a beautiful thing to see a room full of grown athletes talk about their feelings, as is to see a bunch of realtors

do the same thing to a bunch of salespeople. Like, it is a universal language that if you just can put yourself in the position to at least try to receive it, you'll get something out of it. It might not change your world immediately, but you will get something out of it that will trickle, trickle, trickle until perhaps it helps you break through. So maybe I'm just patting myself on my back for saying I'm doing the right thing. But I don't know, I see it. I see it in these sessions. And to me, it really inspires me to continue to do them. Right. No, I love it. I kind of like to end with maybe a little reflection speaking of, like if you would have cated myself earlier on in your career, what would you say to yourself? Where are some of the things that

you wish you'd known? The one that I come back to that's become a little bit of a soundbite that I repeat, because I wish I would have told myself this, in light of all the example set for us, in light of all the pressure put on us, all the expectations put on us, all the social media shown to us. I would have told myself, I would have said, there's no right way to live your life, but there's a wrong way. And the wrong way is to think that there's a right way. That is, we live in an amazing time with there is no right way to build a career. I share my feelings for a living. I literally share my feelings for a living. And I do well for myself. In the same way, there's no right way to be a musician, a salesperson, an artist. Like, there's no, there's no right way. There's many examples set for you, but we live in an incredible time, and it's only going to get crazier with AI and all the crazy things that are happening. I just wish I would have gone back and said, hey, so you don't have to go down this path

because it's what your parents told you to do. You don't have to do this thing because that's the path to a promotion. How can you think differently? Back to our conversation about different. So there is no universal right way. In fact, there is a wrong way. The wrong ways to think that there's a universal right way, especially in light of all the amazing things we could do to stir the pot and do things differently. So I certainly would have leaned into that advice a little bit. Be inspired by other people. Absolutely. Try to surround yourself with people who can educate you and inspire you. Get a mentor, absolutely. But realize the gift it is to figure out what works for you and not to pigeonhole yourself necessarily by the burden of other people's expectations or paths and just celebrate that free. I love every word that you just said, and I would totally tap into that. Like, I think the possibilities right now are mind-blowing and just going to accelerate in a way that is hard to describe, and there's so many options on the menu, and most people

don't even know what's on the menu. And I think, you know, just tapping into that and not feeling, like I'm trying to tell it to my kids, not feeling, like, you have to get this like one thing, right, right? in college and that is the like going to dictate the rest of your life no it won't like just do your best and you know create grit and and love people and trust and yeah so all the things so it's beautiful yeah well thank you case i love it anything that you want to share with our audience i mean we'll obviously have all the cool links and thank you but anything you want to share with our audience before we hop off no i appreciate you giving me a platform to talk about the things

I'm passionate about. I mean, I genuinely love and feel privileged to be able to do this professionally and then, you know, have a great conversation with someone new in my life and to talk about it. So being here is a gift and I appreciate it. And, you know, if people want to listen to the podcast or pick up the book or read any of the quotes, I hope it brings you something into your life that you already knew, but it makes it click in a way that you're like, oh, I get it now. That would be the biggest gift for me. So I appreciate that. And I want for everybody else to just see the possibilities, right? You can take bold moves. You can leap to other things and you can create an incredible, incredible life for yourself based on something you love. Case, thank you so much.

Thank you. Thank you for having me. So if you're feeling stuck or simply want more from your own career, watch this 30-minute free training at leapacademy.com slash training. That's leapacademy.com slash training. See you in the next episode of the Leap Academy with Ilan and Godin show.