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#817: 4-Hour Workweek Success Stories — Charlie Houpert on Building “Charisma on Command” to 10M+ Subscribers, From Charging $10 for Seminars to Making Millions, Living in Brazil, Critical Early Decisions, and The Secret to Freedom - The Tim Ferriss Show | Wave AI Podcast Notes

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#817: 4-Hour Workweek Success Stories — Charlie Houpert on Building “Charisma on Command” to 10M+ Subscribers, From Charging $10 for Seminars to Making Millions, Living in Brazil, Critical Early Decisions, and The Secret to Freedom

The Tim Ferriss Show

Wed Jun 25 2025

Summary

Episode Summary: #817 – 4-Hour Workweek Success Stories with Charlie Houpert

Introduction to Charlie Houpert and Charisma on Command

In this compelling episode of The Tim Ferriss Show, Tim Ferriss welcomes Charlie Houpert, the co-founder of Charisma on Command—a leading platform dedicated to developing confidence, charisma, and strong social skills. Originally inspired by the principles of the 4-Hour Workweek, Charlie's journey is a testament to perseverance, adaptability, and authentic entrepreneurship.

Meeting Tim Ferriss: An Unexpected Encounter ([07:05] - [09:52])

Charlie recounts the first time he met Tim Ferriss, a moment that would later shape his entrepreneurial path.

Charlie Houpert ([07:46]): “I went to dinner with my company... Tim Ferriss walks in and the blood drains from my body. I go cold.”

Despite initial nerves and a shaky start, Charlie reflects on the meaningfulness of that encounter and how it planted the seeds for future collaboration.

Early Struggles: From Management Consulting to Parkour DVDs ([10:11] - [15:19])

Charlie's professional journey began in management consulting, a role that felt misaligned with his passions and the libertarian ideals presented in Ferriss's 4-Hour Workweek.

Charlie Houpert ([11:45]): “Every day it felt like a self-betrayal... having read the Four Hour Workweek at that point.”

Determined to break free, Charlie ventured into launching a Parkour training DVD, inspired by popular culture references like Casino Royale. Despite initial modest profits, the endeavor highlighted the challenges of balancing a side project with an unsatisfying day job.

Transition to Entrepreneurship: Moving to New York ([16:13] - [19:03])

Faced with the reality of his unsustainable side gig, Charlie took a daring step inspired by Ferriss's philosophy.

Charlie Houpert ([16:13]): “My friend was like, why don't you just quit and go to New York and figure it out there?”

Negotiating a remote work arrangement with his employer allowed Charlie the flexibility to pursue his entrepreneurial dreams in New York, marking a pivotal shift towards building his own business.

Building Charisma on Command: Rebranding and Growth ([19:27] - [42:15])

Charlie delves into the evolution of his business from early coaching sessions to the rebranding that would define his company's success.

Charlie Houpert ([31:14]): “If it works, what's the 1 to 10 impact positively if it fails, what's the sort of transient...”

The rebranding to Charisma on Command significantly boosted conversions, moving away from a generic name to one that better resonated with his target audience. This strategic pivot, combined with authentic content and testimonials, led to exponential growth in subscribers and course enrollments.

Navigating Challenges: Authenticity vs. Growth ([42:15] - [84:41])

As Charisma on Command expanded, Charlie encountered the common entrepreneurial dilemma of maintaining authenticity while scaling. He discusses the temptation to "jazz up" content to attract more views, leading to burnout and misalignment with his core values.

Charlie Houpert ([77:26]): “It was, I don't feel good about that. Confronting that...”

This period was marked by internal conflicts, both personal and professional, culminating in a tense split with his co-founder. The experience underscored the importance of aligning business practices with personal values to sustain long-term success and personal well-being.

Key Insights and Critical Decisions ([84:41] - [112:51])

Charlie shares transformative moments that shaped his approach to business and personal growth. From embracing fear-setting exercises to participating in an ayahuasca retreat, these experiences were instrumental in overcoming avoidance and fostering genuine connections.

Charlie Houpert ([86:51]): “I needed to have a conversation with my co-founder that said, hey, I think we're no longer in alignment.”

The decision to part ways with his co-founder was a painful yet necessary step towards creating a business that truly reflected his vision and values. This period of introspection and courage highlighted the essence of Tim Ferriss's mantra:

Charlie Houpert ([06:22]): “The secret to freedom is courage.”

Final Thoughts and Recommendations ([112:51] - [128:51])

In the concluding segments, Charlie emphasizes the importance of continuous learning and authentic self-expression. He recommends influential books like "Six Pillars of Self-Esteem" by Nathaniel Branden and "The Prophet" by Kahlil Gibran, which have profoundly impacted his personal and professional life.

Charlie Houpert ([124:56]): “It's been a minute since I've read it, but I was just like, I'm in that zone of what moved me.”

Tim Ferriss echoes the sentiment, highlighting the enduring relevance of foundational business and personal development books.

Tim Ferriss: “Once you have an understanding of some of these core fundamental concepts, then you can experiment to your heart's content and you can start to break stuff.”

Conclusion: Embracing Authentic Entrepreneurship

Charlie Houpert's journey from a management consultant to the co-founder of a multi-million dollar platform underscores the importance of authenticity, courage, and continuous growth in entrepreneurship. His candid discussions about overcoming personal struggles, navigating business challenges, and staying true to one's values provide invaluable lessons for aspiring entrepreneurs.

Key Takeaways:

Authenticity Over Popularity: Staying true to your values is paramount, even when tempted to compromise for growth.
Courage to Confront: Facing internal and external conflicts head-on leads to sustainable success.
Continuous Learning: Embrace books and experiences that foster personal and professional development.
Value Relationships: Building genuine connections both personally and professionally enriches your entrepreneurial journey.

Discover More:

Charisma on Command YouTube Channel: charismaoncommand.com
Charisma University Course: Available through the Charisma on Command website.
Follow Charlie Houpert on Instagram and X: @charliehoupert

This summary encapsulates the essence of Episode #817, providing insights into Charlie Houpert's entrepreneurial journey, the challenges faced, and the lessons learned along the way. For a deeper dive, listening to the full episode is highly recommended.

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Transcript

Tim Ferriss (0:00)

Hello boys and girls, ladies and germs, this is Tim Ferriss. Welcome to another episode of the Tim Ferriss show where it is my job to interview and deconstruct how high performers do exactly what they do, how they arrived, where they are, the skills, the habits, the tools, everything that went into their journey to mastery of some type. And this episode is an experiment. I've done this long ago, once or twice, people enjoyed it. So I am doing a four hour workweek and case study a success story and this is a fun one. Charlie Hubert is the guest's name. You can spell his last name H O u P E R t He is co founder of Charisma on Command, a company that helps people develop confidence, charisma and strong social skills. His journey from step one is pretty fascinating. There are a lot of challenges along the way, ups and downs, and I think it mirrors the paths of many who have implemented the four hour workwee including sticking points and some people don't overcome those. But he was able to problem solve or at least endure through some of them. So it's very, very instructive. Now. Charisma on Command, originally launched as a four hour workweek inspired muse, has since grown into one of the largest platforms for social skills and confidence training with more than 10 million YouTube subscribers worldwide and more than a billion views across its content in six languages. His flagship course, Charisma University has guided more than 30,000 members through practical step to become more magnetic and I'll give you a teaser, it didn't just work out of the gate, it didn't initially have that branding and there were many side alleys, many attempts example parkour, VHS tapes, instructional and a whole bunch of other stories and examples that I think people will enjoy. Charlie was once voted most likely to break out of his shell and began studying charisma to overcome his own social anxiety. He now explores the deeper roots of confidence through archetyp, disciple psychology, embody practices and much more. You can find Charisma on command@YouTube.com charismaoncommand and you can find Charlie harleyhoopert h o u p e r t harleyhoopert on Instagram and X and now just a few words from the people who make this podcast possible before we get to a wide ranging conversation with Charlie. Thanks for listening. I am always asked by listeners, readers, you name it, what helps me to reset, feel grounded in a world of chaos and doom scrolling, recover from setbacks, we all have setbacks or simply feel at peace. And without a doubt the Answer is always the same, that is going into nature, usually with my pup Molly, ideally. But I do a lot of solo journeys as well. Solo trips out into the wilderness. And for many millions of Americans, myself included, our national park system is the best single place to do just that. Which is why what I'm going to tell you is very, very important to me, very near and dear to me. So I appreciate you paying attention. So let me just mention a few things. Our public lands cover nearly a third of our country's landmass. And with more than 433 national park sites, there's a ton to explore. Whether you're fishing, hiking, or just camping with family. I've been all over the place. I have actually planned trips just around visiting national parks. And the best thing about our parks is that as Americans, we collectively own them. This means we can visit and enjoy them anytime we want. And you may not realize this, but this is a uniquely American invention. And in fact, there is a documentary series by the legendary Ken Burns called the National Parks America's Best Idea. And you can check that out for more. But the point is this. For more than a century, our government has protected our public lands by holding them in a public trust. But it's becoming harder and less safe for us to access these awe inspiring places. And now we are at a precipice. We are at a really key inflection point. And whether it goes up or down will depend on what people like you, people like me do. Congress is preparing to vote on a bill that would force the sale of millions of acres of public lands to, among other things, fund tax breaks for billionaires. So don't love the sound of that. And if approved, the bill would trigger the largest single sale of national public lands in modern history. So this is a big deal and it is very timely. So please join me and many thousands of other Americans who are speaking up to protect our public lands. Visit patagonia.com Tim to learn more. One more time. Check it out, please. Take 10 seconds and do it. Patagonia.com Tim, this message was brought to you by Patagonia Traditional budgeting apps. They can be interesting. Yeah, they can be helpful. I've tried out a bunch, but they don't compare to the complete financial command center that you get with today's sponsor, Monarch Money. And a number of my friends have recommended them publicly have recommended it to me and I had my entire team basically test this app out and they're all still using it. Monarch is like your own personal CFO Giving you full visibility and control so you can stop merely earning and start growing. For instance, one person on my podcast team has tried four other budgeting apps. Said linking his accounts, which includes banking, investments and crypto, had never been easier. And Monarch had the cleanest, simplest, yet most complete UI he's ever seen. It made him want to track his finances. Monarch was named the Wall Street Journal's best budgeting app of 2025 and it's the top recommended personal finance app by users and experts with more than 30,000 five star reviews. So get control of your overall finances, the whole shebang with Monarch Money. 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Charlie Hooper (11:45)

Oh, every day it felt like a self betrayal. So I read the Four Hour Workweek when I was in grad school. And I was in grad school because I was a philosophy major as an undergrad and graduated in 2009, where not only were they not hiring philosophy majors, they weren't hiring anybody. So hit out in business school for a year, wound up as a consultant because that's what you do when you don't know what you're supposed to do with your life. And every day putting on that suit felt like a betrayal of myself, especially having read the Four Hour Workweek at that point. And so there were these minor rebellions that I would stage. Like I had a faux hawk and I wouldn't cut it and I would put it down. There were these subtle, passive aggressive. I let my shoes fall apart. I had my business shoes, but I wouldn't get new ones. They were like ratty and crappy. And it was just these ways of like, this is not me. This is not right. And then I would come home from that after sort of sneaking out as early as I could, and I would write in just my own little journal about like, this is not what I want. I don't want this life. I don't want to be the guy who is my boss or the guy who is his boss. And so was in this period of time that I was noticing and experimenting with coming out of my shell at the same time. So I was able to make friends with not just my boss or his boss, but like I was got close with the President of the company. And it was through just talking about the bars and clubs I was going to at Saturdays. And he was vicariously, you know, we'd meet Monday morning be like, so would you get into this weekend? And we had a little, a little rapport there of, you know, I rem remember the good old days type of a thing. And so had that job wasn't right. Had our fruitful encounter which didn't wind up selling anything. And at the time I was my first business was a Parkour training dvd. I think I even used a service that you'd listed in the four hour workweek to try to do it and was trying to get that off the ground, you know, selling it through Google AdWords very like step by step, four hour workweek. Like it could have been a chapter had it worked. And it was starting to go. But it wasn't something I loved and I was struggling with it because my co founder and best friend was in New York. I was in Washington D.C. how did.

Charlie Hooper (16:13)

It was an integral step. I very much agree with you. I needed the experience of disliking consulting and then the experience of disliking my side gig to go okay, the next side gig has to be something that I would do for free or am paying to do. And so then it was okay, what am I spending money on? It's like, well, I go out to these bars and not to drink, to talk to women and try to get them to like me and to make friends. And I put way more time, effort, attention into studying how our interaction went. I can't tell you how many times I chatted with my best friend about like what if I said this? What if we were. We were putting far too much energy relative to others into understanding people and how to connect better. So there was a transition of my best friend and co founder was in New York, he was an investment banker, I was in dc, I was a consultant. We would talk every day after work for an hour about the interactions we had. And I was just aching like I didn't have other friends in D.C. so I went to this president who I had been close to and there was this moment where I was trying to get the side gig and trying to get a job in New York. And it was, I Went to skillshare and they didn't want to hire me. And I went to all these companies, they wouldn't hire me. I was taking weekend trips. And eventually my friend was like, why don't you just quit and go to New York and figure it out there? So having settled with that and done the fear setting exercises and what's the worst thing that can happen, I came in and I made a pitch to my president, which was it's, I mean, a lot of four hour workweek things, which is, once it's already done, people get out of your way. So I was, internally, I was like, this is done. I'm. We're not talking about if I'm going to New York. So I sat down, I said, hey, you guys have been really good to me. I appreciate it. I just cannot be in D.C. any longer. I feel socially like I'm missing something. I want to be with my friends in New York, but I want to transition in a way that is really good for you, to repay the kindness that you guys have showed me. Which was true. And we sat there and he's like, you know what? Let's work something out. So he winds up saying, instead of being an analyst, let's make you a contractor. Except if you're a contractor, the base rate that we pay contractors is twice as much as we pay analysts. So we'd have to give you basically like a 90% raise in order to do it, but you'd have no job security and no healthcare. Month to month, you could get fired. So I'm like, wait a second, I get to go to New York, double my pay, and no healthcare? This is incredible. So it worked out really well. And I wound up keeping that job, working remotely from New York and making one trip every two weeks for a few months as I did this.

Charlie Hooper (27:46)

Hitting that button, oh my gosh, right. Psychologically, yeah, I'm willing to be seen is the emotional thing. That is, I think for me has been the challenge endlessly in entrepreneurship, the way that I've chosen to do it. So we got that post out and then nobody, of course, read it. And then the next step was, okay, I'm going to promote this. I'm going to go to Reddit, I'm going to go to the forums that are most related. Every man should know. There was a seduction subreddit, there was a New York City related subreddit and I started posting my own things and now comments start coming in and so it's thank you, I like this, or don't promote your own stuff here or, you know, now I'm actually dealing with feedback. But the next stage was posting, posting. I wrote a little short pamphlet book, but the real thing that actually started, I Think early, you might even know. I think you probably know him. I hired Neville Medora for like a day of copywriting to help me design the website and wound up with the first actionable, real thing that I did was okay, I've got people that read my blog. There's like, you know, 30 recurring viewers. And I want to host an in person class that will talk about how to talk to a woman in the park in New York City, which is something that I'm doing with my friend going out and we're breaking it down and how did it go and all that kind of stuff. So we rent out a room in one of these office buildings for like 60 bucks for an hour, an hour and a half or something like that. I go to the New York City subreddit, I give away five tickets. They are sold. People like sold people accept them, right? They accept the five free seats and then I sell the remaining five seats for five or ten bucks. I think I might have sold them for ten bucks each. And like an hour before the class, we sold the last one. So we had 10 people in this class, made 50, lost 60 plus cab fare down 15 bucks, whatever. Go in and give an hour and a half presentation with a PowerPoint on. You know, this is what to wear, say, do stand. Here's how to deal with the fear that's going to come up if she rejects you. Here's how to address that feeling. All of that sort of stuff. Stuff. It was just thrilling to do it. But afterwards, four of the 10 people stayed after and were like, do you do coaching? Do you guys do this? And the answer was, now we do. Right? Like, funny you should ask. Yeah, funny you should ask. So really had no intention of, you know, there was not a business idea of there to be an upsell, but there was enough asking. So then it evolved into, oh, now we're doing traditional. What was around at the time, dating, coaching in New York City. And we're finding our rates as we did that. And that was tough. That's a gig where like you're going out with a dude who's having the most fearful experience of his life and he's paid you to encourage him and support him in facing that fear, which is, I'm going to go speak to that woman that I'm attracted to at the bar in the park, wherever. And it's not fun to like push someone to do something that they're really like they say they want to do, but they're, they're really grappling with. And Then, you know, you go out, you show them. Yeah, it could look like this, it could look like that. So we did that for a while and we're charging, I don't know, a hundred bucks an hour as we did. But again, something else that crept in. Same thing with the Parkour was this wasn't the dream. When I'd sat down and I'd done the fear setting, there's another piece of it, which is you write the 10 out of 10 upside down.

Charlie Hooper (39:01)

So at the time, there's this program, I think it was called Clarity or something. Whereas you could pay people per minute for advice and they would get on the phone with you and, and I don't know what Tucker was 15 or 22 per minute or something like that. I don't remember exactly. And so said I had no money. I was like, okay, 200 bucks. Let's get this done in whatever, 8 minutes, 12 minutes. So call him up, say, hey, can you help? We're having trouble getting customers. Can you take a look at our business? What do you recommend? And he goes, and he goes onto our homepage. It's called kickassacademy.com it's me and my co founder. He's got hair down to his shoulders and he's wearing like a pink tank top. And I've got a neon green pink top and, you know, frizzy hair, hair. And he says, you guys look like douchebags. No one over the age of 26 is going to want to associate with this. It was so true. It wasn't packaged in a very digestible way. But in time, as I started to get other points of feedback, I was able to integrate that. And there was a transition from, oh, wow. What I realized is all the guys who had come with Me, they were like, one of them was the captain of the Princeton football team when he was at Princeton, like, these were successful, cool dudes. But they all had this thing where it's like they didn't really want it to be public that they were learning this kind of a thing. And so we talked to him. We're like, well, you like us, but you don't want anyone to know what's going on. And we learned that, yeah, you know, I do want to get better in my relationships and learn how to talk to women, but I don't want to broadcast it that way, essentially. And I also care about work and I also care about friendships. And so we did a bunch of interviews and I started tracking, like, what word are you comfortable with? Like, what's the 10 out of 10 word that you're down for? And I had a long list. It was lifestyle, design, confidence and charisma came back as like a 9 or a 9.5 out of 10. And so I'm going through this marketing course. Eben Pagan's marketing, step by step. Oldie, but a Grady. Excellent.

Tim Ferriss (42:15)

Let me sprinkle in just a little context on a few things you've said. So, one is Tucker Max. For people who don't know the name, he wrote a number of books. I believe his first mega bestseller was I Hope They Serve Beer in Hell. And he was the first person, actually I would say the only person. In early 2007, I approached Tucker Max, who was part of a panel at south by Southwest. And I was like, okay, there's this long line of people I already know. Tucker's pretty prickly, can be, and very direct. And I somehow heard through the grapevine that he was interested in jiu jitsu or something like that. And at the time I had been doing a lot of training, training. So when I got up there, I was like, oh, have you ever trained with so and so or so and so? And I used that as a wedge in. And he agreed to have coffee or lunch, I can't remember what it was, one of the two. And I gave him a early galley copy of the Four Hour Workweek. And a day later or two days later, whenever we actually met up in person, he came in and he had a research assistant who was named Ryan Holiday, who later went on to become a mega best selling author. Actually one of his books behind me somewhere here. And Tucker said, okay, okay, let me explain what's going to happen. And he's like, I can't prepare you for it because nobody can prepare you for it. And he just went step by step and basically predicted the next year of my life. He's the only one who did that. Now Tucker at the time also was, I think rightly considered a marketing genius and very good at promotion and positioning. Had at the time a massive community, which I believe was based on V Bulletin or something like that. So his vote of confidence, maybe it was a self fulfilling prophecy on some level, but that's just a snapshot of Tucker. Then you also mentioned interviewing people. And I want to emphasize that interviewing various folks because the thing that doesn't scale in the beginning often helps you to scale later. And for people interested in how, for instance, Brian Chesky and the founders of Airbnb applied that, one of the very early masters of scale podcast episodes, episodes has one talking about doing the things that don't scale. And that led to the rebrand, at least on some level, 100%, you change the positioning and the branding charisma on command and everything improves. All the metrics of the website Improve. And in the meantime, though, you are still in the servants quarters in Brazil.

Charlie Hooper (46:49)

So each stage is important. Like, so I'm Dialing it in until I get bored of like, okay, this is what works, this is what creates transformation. But now my role is just robotic at this point. It's not as dynamic as I'd like it to be. So given that I can do it once and be done, maybe I should just make an online course. Thank God for this pre selling thing though, because it runs you through this process. This time I've been posting on the blog, I think we have 5,000 people on the email list. And I follow this template, which is something like, hey guys, I was about to go into a cave and make this online course and I remembered that that's stupid because I'm making it for you. So before I sit down to record it, I just want to know what is the biggest problem you're facing related to charisma? If you reply to me, I'm going to make the whole course, but I'm going to make a piece of it for free that I'm just going to give everyone who replies. So they come in, they give me all their answers. Step two, you take all of those things, you bucket them and categorize them and you put them into like radio buttons. Ranking things in one of those survey monkeys, whatever you want, say, hey guys, thank you so much for writing in. I think I have the top things. If you would just vote on which one you most want me to actually make the free piece on. That would help me to decide which piece to make for you. So then I get back and the first thing it was how to make an amazing first impression. How to feel unshakably confident, how to have a conversation that flows effortlessly, how to tell great stories, how to have body language that's magnetic, and how to be a good leader. And in that order is what they ranked them. You know, number one, first impression, number two, confidence. So I get this and they just gave me the outline of my course in addition to all of the specific phrases, questions, things that, well, need to be answered. So I say, hey guys, I'm making a course. It's going to cover these things. First impressions, how to be unshakably confident, effortless. You know, all this stuff it's going to sell for eventually. I think I started it at 800, we lowered it to 600, but it's going to sell for 800 bucks. You can get it for $500. But here's the catch. One, you're going to have to do a one on one call with me, right? Which is exactly what they want to do. Two, there's going to be group interaction throughout the whole time. And three, I really want your feedback throughout the course so that I'm building it exactly to be what you want. And so we offer 25 seats like this and, and that's the most money we make. $12,500. We sell out, people are stoked. And for us it's oh wow, I was going to make this course and what I learned. Now each week I get on a call, I talk to several people one on one and I develop the content that I then send to them and they give their questions and it's this iterative interactive thing over six weeks. And they, with their questions, completely reshaped the course. I thought I was going to make. I thought I was going to make a course about all these advanced tips and tricks. And of course, if you've done something for a while, you always overlook the beginning phases, you overlook the fear, you overlook all of those things. So we focus way more on getting through that. And the course as a result is tailored to where my average audience member is. Right. The guys that I wanted to work with that I started filtering by calling the company Charisma on Command. And I have all these surveys that have language that then become the sales page on the back end. So like, do you want to walk into a room and be the guy that people instantly notice and that they're drawn to magnetically? Like that's phrases that they wrote in their descriptions of what they were asking for and wanted. So on the back end of this, I have my outline, I have my course, I've gone through it, and so now I can go record this thing and offer it on the website. So all of a sudden these blog posts, which had nothing to sell to have something to sell to, so now like actual money can start coming into the business while I sleep. So we're selling this course, we're getting, you know, one a day or one every other day that's going to pay.

Tim Ferriss (65:06)

I want to touch on maybe a few expansions of that just briefly for folks. So you might recall back in the day, this is, let's just say, maybe even pre Eben Pagan and so on. If you were to look at different types of online marketing, a standard operating procedure was long sales letters with lots of yellow highlights. And that was how you did it, period. That was the scripture of online marketing. But lo and behold, that isn't the only way to do things. And in fact, you can approach it completely differently. Now, if you go through almost any website now that sells software as a service, you'll see somewhere on the product comparison or on the checkout portion. When you're selecting features or plans, they'll have three options. The middle will say most popular. There's a very cheap one with half the features you need. There's a super expensive one that only 2% are ever going to consider. And then there's most popular in the middle. And while the presentation changes, I would say there are a few takeaways. Number one is you can always experiment and break the rules. Number two is there's certain things that don't tend to change that that much. So you can still look at caples on advertising for copy editing. You can look at old print advertisements from Ogilvy. You can read for instance, influence. So there are certain things you can study. Like if drawing is learning how to see. Sure, you might have a Crayon, a pencil, a paintbrush, piece of charcoal. But those are tools that can be adapted based on certain base principles. Then you can feel free. Once you have an understanding of some of these core fundamental concepts, then you can experiment to your heart's content and you can start to break stuff. I don't know, I mean a lot of it. Because platforms have so much value capture and are so powerful now, if they do decide they want to promote X, Y or Z and they have a template for making you conform to that, then I would imagine, imagine there's a decent amount of pressure to be pushed in that direction lest your videos or tweets, whatever tweet is called on X or whatever it might be, doesn't get the distribution that you would like. Now, you mentioned shorts or shorter clips, not needing maybe the type of sell to be watched, ostensibly because they're shorter duration. Do you see much of a conversion from shorter clips to viewing of longer clips or subscribers? I don't know which metric is the one that matters, but I'm curious.

Charlie Hooper (68:00)

We ran a little experiment. I have not put a lot of energy into shorts because the answer was there's a couple of things to your first point and I'll come to shorts with all of those ogilvies. Whatever. What I've found is that if you take the tried and true ways of doing it and you run it through your own value system and you don't allow for things that don't align with yourself, so I'll just give you. For instance, we used to do discounts because that was what you were. That's what you do. You do a discount. And I got an email from a guy who was like, hey, I love your stuff. But like last week my friend who didn't buy your thing and was on your email list for 30 days got offered this thing for $400 and I bought it immediately for 600. And I realized that we were, in a way, we were penalizing our most strident, ardent, willing customers for not sitting on the fence and offering discounts down the line line. So made the decision to chop off discounts. It hurt the business by 20%. But you get an audience of people that has a different degree of trust with you. And so all of these rules, like, you can win short term by doing a lot of different things. You can do clickbait titles, you do all sorts of things, but you're establishing a relationship with every business decision. So I find that like running all of those things through the center is helpful. So when it Comes to short, one of them is I don't really like shorts. I find that I've never really gotten tremendous amount of value from a short. I've gotten value from YouTube videos, blog posts, videos, all sorts of things, but I don't connect with them. So I haven't pushed shorts. We did a few experiments and what I found for the way that we do things is no, that we didn't see. We got a ton of subscribers, but we didn't see a strong connection between long form and short form and purchases. I'm sure that somebody else could make that happen. Even though that was the way the wave was going, that's not the way that my wave breaks. That was not a particular trend I was interested in.

Tim Ferriss (71:11)

The podcast, I've thought, especially with the 10 year anniversary not too long ago and hitting some major milestones in terms of total downloads and listens and so on, I thought, well, if I were going to pack up my 10 content and move on, this would be a decent time to do it. However, I suppose for myself, I just realized, well, even if I weren't recording conversations, I would still be having these conversations. And therefore for the cost of a microphone and using an online service to record a podcast with some basic. I mean, it's not fancy lighting as Anyone can tell if they're watching me right now, right now, but for the minimal cost of production, especially when you consider that a lot of these conversations I would be having would be via Zoom or FaceTime video. I might be walking around outside having this conversation, but I could also have a headset on where I'm recording. So the lifestyle inconvenience to me of recording the conversations I would have otherwise is close to zero. And I would say success is having thought provoking conversations. Ideally, I learn something or feel something from those conversations, maybe both, and then I get to share them. Because the origin of the podcast, I mean, it's easy for me to forget, but there are a lot of factors that contributed to it in 2014, but one of them was I was living in the Bay Area, in San Francisco at the time, and, and I was having the most incredible conversations with brilliant people. At least people I thought were brilliant. The density of intelligence there is so high. I mean, there are a lot of issues as well, but it just seemed like such a shame, not too dissimilar. I mean, it's slightly different, but it's closer than people might realize where it's like you're doing the one on one coaching. It's like, yeah, it's good to help one person, but then if I want to convey this to a second person, let alone 200 people people, I have to repeat it. And for me, these conversations were like sand through the fingers that I could not in any way convey to someone else. And I was like, well, let me just try to record some of these. Which is why the first 10 to 15 were with friends of mine also to make the lift as light as possible. And I feel like I would definitely miss recording because I would, let's just say I quit the podcast today. Next week I would have an amazing conversation with someone and I'd be like, God damn it. I'd like be, be like, it's so selfish of me not to just click record on an iPhone with a half decent headset to record this thing, because fuck, it's a real privilege to have access to the network that I have access to. Which doesn't mean, by the way, that everyone's going to know every person I talk to. I prefer strongly if they don't. But success, to me right now, it's honestly scratching my own itch. For instance, I'm thinking of potentially compiling a whole lot of four hour workweek related case studies because very early, very early in my entrepreneurial journey and I'm not recommending people go buy this book. I think it's out of print anyway. But Entrepreneur magazine had this book called Young Millionaires. And it was like two to three pages, profile of each young millionaire, which meant somewhere between 20 and 35, I suppose. And it was like, how much it cost to start the business? $200. How much they made last year in revenue, next year, estimated revenue, type of business. And it ranged from pest control to crime scene cleanups.

Charlie Hooper (83:07)

Yes. And I'd been doing it weekly. There was an authentic drive to do it weekly. That's then slowly shifted and it became I don't want to do this. And then it was, I definitely can't do this. And I at the time, so many other things were going on in my life. We can go into it or not. But there was a moment probably in 2018 where I needed to have a conversation with my co founder that said, hey, I think we're no longer in alignment. Alignment with this business. Like I've been driving the growth with these videos. Your projects have not succeeded in the same way. Not for the sake of money, but for the sake of honesty. We have to have a talk about our 5050 split. But money was never the drive. The drive was always be with my friends in Brazil. And so I didn't care. But there was a. As my own inability to have sincere, authentic conflict crept into the business, it cascaded downwards. So I'm avoiding having a difficult conversation with my co founder. We hire somebody else to cover that up. Turns out years later that we hire somebody who fabricated a bunch of stuff and stole money from the business. And all of it was just from this core pattern of not wanting to face the problem and just wanting to squint at it and say, everything's good, you know, like the money's coming in, people like it, it's sad, etc. And so what happened was, and again, I was so happy, broke in Brazil, sleeping on the ground, unable to afford food. And then I had the experience, the cliched one of I've made more money than I've ever made, everybody wants more, they think it's all great and I feel like shit, I feel awful. And then I have a breakup right before my 30th birthday and I'm going to collapse. Some things we can go into anything. I am invited to an ayahuasca retreat. I have been in, you know, having these issues that have not surfaced. I don't smoke weed, I don't drink, I'm straight edge. But it, I'll give it a try. I go head first into this ayahuasca experience with no idea what's coming. And that starts what has now been a seven Year process of completely turning my life upside down and having to face everything that I hadn't looked at, which was of course these things in the business, but even more importantly the patterns of avoidance and people pleasing and seeking that had been birthed in my childhood. And so happy to touch on all of that. I know it's a broad spanning.

Charlie Hooper (88:19)

It was pieces. First it was oblique conversations like, hey, I'm not feeling. This isn't feeling great. And then seeing what I got back. And then it was more confrontational. And the essential problem was I did not know how to have a boundary and tried to negotiate boundaries endlessly with people that I loved instead of saying, I love you, but, like, past this line is not okay with me and I will not comply. It was, well, can't you see why that would be fair for me to. To have this perspective? So if there was a shift, it was. The big thing that happened was over these years, I had started to develop a therapeutic relationship with a therapist and a number of friendships where I was being met in ways that I did not think were possible and to not use therapy language, language. Like, I felt that people wanted to hear the ways in which I was upset with them or angry and wanted to repair in ways that actually didn't just paper over the problem, but felt good. And when I brought that possibility, I was like, holy shit, this can happen. Let me bring myself. That was not the result of my conversation with my co founder. It did not go that way. And knowing that it existed now and then not getting it there made it like, okay, this is no longer working. We need to separate. Separate. And so what happened was, first it was with the friendship, but secondarily with the business. It was tough for me to come back to. To say, I don't want you to make videos anymore for the business. I don't feel that they're aligned with what I want to say. I made videos for, I don't know, the first 3ish years, and then got burned out. Was like, will you please step in? And always didn't want to look at the videos. Like, whatever the money's coming in, I don't want to see. And when I. I actually had to sit down and literally watch them. And not that there's anything objectively wrong with them, but they weren't aligned with what felt right for me. And I had completely Abdicated that responsibility of saying, this doesn't feel good. Confronting that, I felt so evil and awful and bad for having that perspective. Like I was being too cruel or too mean. But I had become more grounded in not saying that you shouldn't make videos ever. I'm not saying that you shouldn't do this, but this doesn't work for me. So we just paused. Literally making videos on the Chann channel for one year. Business starts to nosedive, right? Like, not immediately, but the videos don't get views forever. Business falls off 20%, 30%, 50%. And it was again a question of like, which. It wasn't a game. It was, I just don't feel good about that. And so through that process, we were talking about the future of the business and what I buy, would he sell. We couldn't find an agreement on who would do what. And I can talk about the negotiation if you want. But we finally settled on, I'm going to buy the business all out. I'll pay you for the piece and you'll have no restrictions. You can make any sort of content that you want on any other channel. But this is going to go, I'm going to take this, I'm going to give you cash. And honestly, it was, it's what both of us wanted. I think the thing that we didn't acknowledge is that we had fundamentally different drives. Whereas mine was more creative expression and his was more financial security purity. And that split, it's very tough. It just doesn't align well. Especially when what you said, I did not feel he has a different opinion that we were equally contributing to the financial success of the business. So yeah, it was harrowing. More importantly than the business split was that it was my best friend and we're not that anymore. And so it was going through the ringer, it was dark, night of the soul type challenges. So grateful for it. And it was painful as hell. Hell to experience.

Charlie Hooper (102:38)

Yeah. So I went back and filmed it. And I still have insecurities and this and that, but I did my best effort to make it okay for Tim, for you. And when it was done, the next video that I made, I spoke about it and I said at the end of the video, I said, this is the best I can do. This is the greatest thing that I can possibly make for you guys on this topic. And Converge exploded. And every ad read after that had a Significantly higher, like 2x or more lift in conversions. And we started getting more testimonials and it was this, like, if you don't believe in it fully, you're going to sell it with hesitancy. So being able to tell the truth and the truth was not, this is the greatest thing in the world. It's, this is my absolute best. If you like this blog, this is the best I can all offer you. And at this point, the truth is, it's no longer true. I feel like I can do something better now, so I need to go back, do it again and then be able to honestly say, this is the best I can do. And I'm sure that will have the same impact because I subtly shy away from selling, from offering the thing that I don't fully believe in. So that was a big one. It's tough. I don't know how to parse it out. But this plus adding Testimonials was a 4x conversion lift when we started adding those at the end. So we used to add, have our call to action. It was a 10 minute video. And then like, hey, if you want to buy Charisma University, it does this, it does this, it does this. It's, you know, it's got all this, here's what's in it. And then it became, hey, do you want to buy Charisma University? Here's what somebody said about it. This helped me get a promotion. It did this. Here's what somebody else said about it. I got a girlfriend. Here's what somebody else said about it. And they were just literally photo comments that People had left in the comment section or emails that they sent in. And that combined with the I care about this more was a 4x total conversion lift, which was huge. There was the avoidance was something that I had to pay for on the backend, the avoidance of conflict. And I think this is one I didn't know how to just allow people to know that I was disappointed or upset or hurt or angry. I had to fix everything very, very quickly. A lot of people pleasing tendencies, those compounding over time created a lot of issues. There was not firing the person who wound up stealing. I knew that I needed to. There was a lot of like not firings that were huge. And then there was the walking away and the returning which was really, really important. And they were both honest. The one was like, I'd rather not have this thing send me money than post videos that I don't feel aligned with. Which made me like, oh my God, when you do stuff that isn't aligned for money, it signals such a lack of self belief and self love. This is in the six pillars of self esteem book. Like when you start trading your beliefs for cash or approval, you're just sending a signal that I can't be relied on to be myself and be safe and earn. But when you do things that are detrimental to income, like not offering a discount, like saying, I don't want these videos to go up, not to punish anyone, but just because it doesn't feel aligned, I have felt every time where I've dropped into that this pattern, power arises in me. And so that was like, oh, holy shit. I felt like a beggar in a weird way. I'm making all this money, but I'm like feeling unsafe that I need to beg for more and ride the coattails of this thing that I built that I can no longer do. And as soon as I said I don't want this, I felt a surge of like, oh fuck, I have more to say. I have more to contribute. So that was huge. And then in the negotiation, the big moment was two things. Things. We'd been at deadlock for two years. I made him an offer. It was nowhere near what he wanted. We were just not able to meet. There were two things that happened. One was we're starting to get into these circular spirals of things aren't working. And I paused and I said, hey, it sounds like you're really scared. And we just talked about our feelings and the fallout of the friendship and the fears that we both had and. And acknowledging the emotional intensity of this that was essential. Like pretending that this was a business transaction, that we were like, that's a lie. That's not what was going on here. We were both really afraid. And speaking to that and bringing it to light moves things tremendously. And then the second one was honestly going to him and saying, I am willing to sell the business, I'm willing to sell it, but I need one thing which is I need a no non compete. I need the ability to go and make anything that I, I want anywhere. And that moved us from, I'm trying to buy from him. He wants more money. I don't want to give him the money to okay, make me an offer. He made me an offer then for that and I said, I'll give you 20% more than that. And it was done, deal over.

Charlie Hooper (107:57)

Joe's awesome. You know, it's funny, I got, I have to admit this, it was Father's Day last Sunday and I was making the joke. I'm like, I'm meeting all my dads in one week. It's my dad and Tim Ferriss. And Joe Hudson is going to be here in two days. And it's, for me, it's a significant thing because the truth is, and I told you I had a ton of projections onto you, you know, like if Tim helps me, it'll save me. And I had the same thing with Joe because Joe's work was also deeply important to me. And so it's just really cool to like, you know, drop some of the projections and meet the people. So all my dads, Joe Hudson's my third dad. He's great. He has a thing called art of accomplishment. And he acknowledges the emotional aspect of business and not only acknowledges it, but points to the fact that if you ignore it, you will either not do as well as you could or you will do as exceedingly well and feel that empty, burnt out thing that awaits everybody who trades the inner asset for the extra external one. So his work was extremely helpful. I'd gone through his courses and he offered me because we'd been in contact, a private coaching session because I'd helped him with some YouTube stuff. And on that he literally suggested, he said, offer to sell. Like, are you willing to sell? And I was like, then make the offer. Do a shotgun deal where you guys both write a number on a piece of paper and the person who is willing to spend more will take it. So just knowing that I had that, I brought that to my co founder and said, look, I'm willing to make a binding agreement about, about this where I am genuinely willing to buy or sell. It was that shift of like, it was, I needed to buy. He was like, well, give me more. And when it's like, look, I don't need to buy, but let's get our way out of this thing, his number came down essentially is what happened. And there was one final thing that was I, based on loving advice from people who were supporting me, had wanted to buy the business out of net revenue, which is to say with safety valves on, if it doesn't perform, I don't have to pay pay you. And that we couldn't find a number for. It just didn't feel good. And I had a number come through, a literal number that like came to me and I was like, that's way more than I've been offering him. And he said no. And the next follow up was, yeah, because you're going to take all the risk. And I felt a surge of fear and then that self belief energy come back and like, oh my God, yes, I want the risk. I don't want this if it works. I want this through rain or shine, good or bad, like, let me pay the price for not succeeding and I'll take you back to one. It was the burning the boats that finally made the business work. At every stage, it was taking the steps that got me to not have the contracting job to move to Brazil. I'm committed. I care about this enough to suffer and hurt if this doesn't work out. Right. And so that was also huge in that. And it was huge at the beginning of the business.

Tim Ferriss (112:17)

Yeah, totally. I've been asked so many times, as you would imagine by publishers to go back and kind of of fine tune rewrite that book and I don't want to touch it mostly. I mean, I appreciate you saying that it somehow captured lightning in a bottle and I'm like, Look, I'm 47 right now. I wrote that when I was 29. And sure, if I read it now, there's a little bit of chest puffing and there's shit in it where I'm like, oh my God, it makes me face palm a little bit. But. But for whatever reason, that book has just stood the test of time, at least over 20 years or close to it, and resonated with people from so many different age brackets, going from 15 all the way up to retiree. I don't want to touch it. And to your point though, fundamentally it's about calling into question all the basic assumptions of career return, retirement slave save, retire, the deferred life plan, and looking for alternatives that you can effectively prove are, if not realistic, at least possible vis a vis these case studies that are already in the book. And the vast majority of those case studies predated the publication of the book. So I do myself also, I Mean, I think that's a byproduct of enjoying books that do that on some level. Let my people Go surfing. I think this is the title of the book by Yvon Chouinard. I remember reading books by Ricardo Semler and Branson, Losing my Virginity, where it's like, okay, everyone says an airline is suicide. He workshopped it, in a sense, because a flight got canceled. He walked around with a sign at an airport offering charters. And then once he had people booked for a charter, he chartered a flight somewhere, then figured out how to work with, I think it was a Boeing at the time to effectively cap his downside so that his losses were contained. But the upside was attractive. And you look at how he structured some of these deals and it's like, oh, yeah, it wouldn't have occurred to me that that was possible. But of course, when you have someone like that who is scrappy and also had the life experience of having to pick himself up by his bootstraps and work with next to no money, it's like, oh, wow, you just had to ask and you had to know the right way to ask. And these apparent miracles can happen. It's just wild. So we'll see. Maybe I'll put together that book of case studies. I think it'd be fun.

Tim Ferriss (121:11)

Right. And for me at that time, keep in mind it's a few that was however many years, not that many really. I mean, we're talking five or six years after for my purposes in life, lifestyle design, cracking the code or at least figuring out elimination and automation and all these various things to an extent that seemed very unusual at the time. I was still really high on that experience. And you can't be a lukewarm evangelist or lukewarm teacher. I didn't really view myself as an evangelist, but the harder the subject is, the more enthusiastic you better be. Or at least enthusiastic and effective teacher. If the subject matter takes care of itself, then there are lots of ways that you can perhaps compromise or not be up to snuff. But entrepreneurship is a full contact sport, as you know. And the chapter that I think gets the least attention, if I were to expand something that I would expand is the Filling the void chapter at the end. People miss that and it's so important. It's like, look, if you just create a lot of empty space in terms of time, humans are not really designed just to be idle and go spend some time with any reasonably intact kind of hunter gatherer society that might have some plantains and cassava or something like that. And you'll see, yes, they do rest quite a bit, but they're also by and large very active. Might be just household stuff, might be chores, might be any number of duties, church, et cetera, especially these days. But idle hands or the devil's workshop applies to the mind as well. So for mental health, I think that that chapter is particularly important and maybe could have been positioned a little bit differently to underscore it. But that's the type of chapter also that number one, most readers don't assume they're going to have to deal with because they're like, well, that's like once you've won the race. I'll worry about that once I've won the race. Unfortunately, if you build a business and a machine to serve lifestyle, but then it becomes inverted, it's not exactly straightforward or it's certainly not pain free to fix it at the 11th hour after the fact. So I relate to the book well. It is funny to me when I look back at some of the tech recommendations and I'm like, oh my God, this is just like going to the Natural History Museum and seeing dinosaur bones. I mean, most of these are completely extinct.

Tim Ferriss (128:51)

Maybe a framework or two to try to calibrate, to learn how to do that. She's a very good teacher. And I suppose we'll cap it there, man. Thanks so much for taking the time. Really had A lot of fun and for everybody listening. As always. We'll link to everything in the show notes at Tim Blog Podcast. Not too many Charlies on the podcast, so if you just search Charlie Hone. Yeah, Charlie Hone. Charlie Hone might pop up on the blog, but other than otherwise, Charlie Hoopert will be the one and only. And until next time, as always, be just a bit kinder than necessary. Not just to others, but to yourself. And thanks for tuning it. Hey guys, this is Tim again. Just one more thing before you take off and that is five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the week? Between 1 and a half and 2 million people subscribe to my free newsletter, my super short newsletter called five Bullet Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I found or discovered or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums, perhaps gadgets, gifts, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange, esoteric things end up in my field. And then I test them and then I share them with you. So if that sounds fun, again, it's very short. A little tiny bite of goodness before you head off for the weekend. Something to think about. If you'd like to try it out, just go to Tim Blog Friday, type that into your browser. Tim Blog Friday. Drop in your email and you'll get the very next one. Thanks for listening. I am always asked by listeners, readers, you name it, what helps me to reset, feel grounded in a world of chaos and doom scrolling, recover from setbacks, we all love setbacks, or simply feel at peace. And without a doubt, the answer is always, always the same. That is Going into nature, usually with my pup Molly, ideally. But I do a lot of solo journeys as well. Solo trips out into the wilderness. And for many millions of Americans, myself included, our national park system is the best single place to do just that. Which is why what I'm going to tell you is very, very important to me. Very near and dear to me. So I appreciate you paying attention. So let me just mention a few things. Our public lands cover nearly a third of our country's land mass, and with more than 433 national park sites, there's a ton to explore. Whether you're fishing, hiking, or just camping with family. I've been all over the place. I have actually planned trips just around visiting national parks. 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