The Bossticks - Evolving Like a CEO: Jason Feifer on Leadership, Growth, Boundaries For Success, & Building a Life That Scales

Episode Date: October 9, 2025

#893: Join us as we sit down with Jason Feifer – Editor in Chief of Entrepreneur magazine, startup advisor, keynote speaker, and a widely recognized authority on business and communications. Jason has interviewed some of the biggest names in entrepreneurship & witnessed firsthand how the world's top founders scale from the ground up. In this episode, Jason gets real about the power of vertical thinking, the value of respecting others' time & setting boundaries, the truth behind hustle culture, and how the most influential leaders continuously evolve, adapt, & strategize for long-term success.   To Watch the Show click HERE   For Detailed Show Notes visit TSCPODCAST.COM   To connect with Jason Feifer click HERE   To connect with Lauryn Bosstick click HERE   To connect with Michael Bosstick click HERE   Read More on The Skinny Confidential HERE   Head to our ShopMy page HERE and LTK page HERE to find all of the products mentioned in each episode.   Get your burning questions featured on the show! Leave the Him & Her Show a voicemail at [phone].   Visit http://OneThingBetter.Email To join Jason's One Thing Better Newsletter.   Visit https://cpgfasttrack.com to get involved with other CPG Founders.   To check out Lauryn Bosstick's feature on Entrepreneur Magazine and the Problem Solvers Podcast visit https://bit.ly/LB-Entrepreneur.    This episode is sponsored by The Skinny Confidential  Wear with intention. Wake up with ambition. Shop The Skinny Confidential's latest drop - The Fall Edit, featuring Uniform and Blanc. The limited-edition Mouth Tape made for those who take their beauty sleep seriously. Available now at https://bit.ly/TSC-NEWNEW.   This episode is sponsored by AG1 Go to drinkag1.com/skinny to get a FREE Frother with your first purchase of AGZ.   This episode is sponsored by Jolie Head to jolieskinco.com/SKINNY to try it out for yourself with FREE shipping.   This episode is sponsored by Function Health Visit functionhealth.com/SKINNY or use gift code SKINNY100 at sign-up to own your health.   This episode is sponsored by Branch Basics  Shop Branch Basics in 600+ Target stores nationwide, or http://Target.com. Use code SKINNY15 to get 15% off at https://branchbasics.com/SKINNY15.    This episode is sponsored by Coterie Head to http://coterie.com and use code SKINNY20 at checkout for 20% off your first order at http://coterie.com.   This episode is sponsored by Beekeepers Naturals  Go to http://beekeepersnaturals.com/SKINNY or enter code SKINNY to get 20% off your order.   This episode is sponsored by 7Diamonds  Use code SKINNY for 20% off your first order at http://7Diamonds.com.   Produced by Dear Media

The following podcast is a dear media production. She's a lifestyle blogger extraordinaire. Fantastic. And he's a serial entrepreneur. A very smart cookie. And now Lauren Everts and Michael Bostic are bringing you along for the ride. Get ready for some major realness. Welcome to the skinny confidential, him and her.

Hello everybody. Welcome back to the skinny confidential, him and her show. Today we're sitting down with Jason Pfeiffer, editor-in-chief of Entrepreneur Magazine, and someone who has a front row seat to the most influential founders and CEOs in the world. Jason has interviewed some of the biggest names in entrepreneurship, such as icons like Gary V, Ryan Reynolds, The Rock, and Jimmy Fallon. He has seen businesses scale from the ground up and studied the cultural shift shaping entrepreneurship today. In this episode, he's giving us the ultimate insider's guide to entrepreneurship with tangible tips for anyone,

even if you're not an entrepreneur. Surprising stories and tricks you can apply right now to build, adapt, and succeed in your career and in life. With that, Jason, welcome to Skinny Confidential, him and her show. This is the skinny confidential, him and her. All right, Jason, you've had a front row seat to the most elite entrepreneurs in the world. From your perspective, what truly separates them from everyone else? It's one thing, adaptability. That's it.

We equate change with loss, right? Decades of psychological research have confirmed what's called loss-aversion theory. Like, our human brains are programmed to protect against loss more than to seek gain. So when something changes in our work or in our work, lives. The first thing we do is just like freak out because we're thinking about all the comfortable, familiar things that we have in our lives and our business that we're going to lose. And then we start really freaking ourselves out because we start to extrapolate the loss. We're like, if I lose this, I'm going to lose that. I'm going to lose that other thing. The most incredible

entrepreneurs I've found get to pause that natural human reaction and start to think, what is the next opportunity? Because this thing is changing, how can I think about what people need next? can I move there faster? They're not afraid to abandon what came before to the benefit of what came next. Over and over again, that is what separates successful people from unsuccessful people, not stop. That's really interesting that you say that because I noticed during COVID when everyone was freaking out, running around like, without chickens without their heads on. Yeah. That the ones that really succeeded were the ones that took COVID and used it to their advantage. So like we just had Rebecca on of Love Shack Fancy.

And she saw it as an opportunity to, you know, maybe like lean into her e-com store and blew that up. And she got some commercial spaces and some leases that she couldn't get pre-COVID. You know what I always think of with COVID was the conversation, the last conversation I had with an entrepreneur before everything shut down. So my friend Nicole Lapin, who I co-host a podcast with called Help Wanted, she hosted a little dinner for her birthday, like right before COVID. It was the last social thing I did before COVID. And I was sitting next to a friend of hers named Megan, and Megan ran a live events company. And we didn't know what was happening, right?

We were still out and about, but things were starting to shut down. Like the NBA had stopped playing. And I said to Megan, you run a live events business. Are you freaked out about what is about to happen here? And she said, you know what? I'm not. And that's because we spend so much of our energy, all of our energy at my company.

producing these live events. And we have all of these other ideas for how to grow the business. And we're never able to actually implement any of them because we're absorbed with the live events. And now if the live events hit pause, we can shift our energy and explore some of these other things. And at the time, I thought, this is a woman who has no fear. Like, this is like an inhuman thing.

But the more I thought about it over the next year, year and a half of the world imploding, I realized, no, Megan is not a person with no fear. Megan is a person with the right kind of fear. I think there are two kinds of fear. There is fear of losing what you already had, which is what forces people to hold onto what came before. And then there is fear of not finding the next opportunity fast enough. And that is an optimistic fear,

because that is rooted in there is something else. If everything is changing, if your industry is changing, that doesn't just mean that you're being impacted. That means that all of your customers are being impacted and that all of your competitors are being impacted. And people need things. In a world of change, people need things. They need new things.

And they're looking to you or somebody to create that solution. And that is the kind of fear that I think we all should have. What do you define entrepreneurship as? Like if you were to give a definition in your own words? I think that an entrepreneur is someone who makes things happen for themselves. And the reason I define it like that is because I don't think that you have to have built a business

to be an entrepreneur. I know that may be controversial, but the reason is because I see people who work in a corporate environment who can draw lessons from entrepreneurs. Probably a lot of your listeners are not quote-unquote entrepreneurs in the traditional sense.

They're not building businesses, but they love the conversations about entrepreneurship because they can absorb that lesson and that mindset, that way of thinking, and then they can apply it to things that they build. To me, the difference between an entrepreneurial mindset and a non-entrepreneurial mindset is what I call vertical thinking.

So I became entrepreneurs editor-in-chief in 2017, 2016, something I don't know. I lost time. Well, almost a decade now. Yeah, it's kind of crazy to think about. And it's possibly the longest, it's certainly the longest job I've ever held, but it's also probably one of the longest

just holding of any seats in media these days considering how much turnover there is. So when I entered entrepreneur, I had been working with my wife for a couple of years on something totally different, a romantic comedy. We had this novel that came out. It was called Mr. Nice Guy, totally different than entrepreneur.

Each week, two people sleep together and then critically review each other's performance in a magazine. That was the premise of Mr. Nice guy. How was my performance last night? Performance is pretty good. Good. A plus. That's why we have three children.

A negative answer would have been more interesting. I was like, well, I really? Yeah, that was the premise of the show. I'm going to keep it on track. What would happen if people were like giving real talk to something that nobody's ever super real about? Anyway, so this book comes out and I'm at Entrepreneur Magazine. And I was getting two totally different reactions depending on how I knew somebody. So my writer friends, they would hear that I wrote this book with my wife, it came out at St. Martin's Press.

and they would say, that's so awesome that you wrote this book. Congratulations. And then I would talk to entrepreneurs, and they would say, well, that's interesting. What are you going to do with it? And I didn't understand the distinction

between those answers until a little later. When I realized what was happening was that writers and the world that I came from, think horizontally. You do a thing, you put it out in the world,

and then you move along. And then you do another thing, and then you move along. And you just keep doing that. And that is what most people do. But entrepreneurs think vertically. They think the only reason to do something is because it is the foundation upon which the next thing will be built. And that forces you to think incredibly intentionally.

And people get it wrong. I just, I like looking at Jill because that's how we're thinking about my next book. This is cool. I like this. Keep going. Yeah. So where people get it wrong is that they think they have to know exactly where they're going to at the beginning. and then they lock themselves into a specific path, that is the mistake, right?

Like Malcolm Gladwell said to me, self-conceptions are powerfully limiting. Like, if you have too narrow an idea of what you do, you will turn down all of these incredible opportunities along the way. So you don't want to know the end goal because you will limit the opportunity, but you do have to think intentionally about how one thing can lead to and should lead to the next. and that starts to help you filter the opportunities that you actually pick. And that, I think, is the distinction between, like, non-entrepreneurial thinking and entrepreneurial thinking. It makes a ton of sense.

And I was just, like, even thinking about, you know, when we started this show, it wasn't because we wanted to be necessarily, like, stars in the podcast world. It's because we looked at it as, like, the foundational thing to go and build other things. And even, you know, like, then it, like, extrapolated into dear media and some brands. Right. And even funny, and we'll talk about this when you and I talk, like, I still have no, interest in building a podcast network or business. It was just the Trojan horse in order to get me into the thing that we're ultimately doing now. It was like it's a foundational piece. Right. And I think, you know, sometimes I struggle with people when they're like, when they come and it's

like, I need to make money. What's the end goal? And I'm like, well, sometimes you have to build the building blocks in order to get the thing that's actually doing. And sometimes that initial building block is not a net positive. Right. But entrepreneurs think about it in that way. It's like it's a piece of a puzzle where sometimes a lot of people who it's like, I need to be paid for everything before I do anything. Right. And so much of early stage entrepreneurship, and I would argue actually the entire journey is just data gathering, right?

You launch something to learn how people react to it and to see what other opportunities it creates. And that is incredibly valuable. And another reason why you don't necessarily need to know what happens next, I mean, Lauren, you and I spoke earlier, and you were talking about how you believe that entrepreneurs today should build the audience before you even build the brand. And what you're really saying is that you're building an asset and that asset is usable in all sorts of different ways. But really, building an audience is just building a massive data set. And you're getting tons of

people who are going to share all sorts of things about what they see in you and how they perceive your value to them, and then you can build upon that. That's incredibly smart. That's really interesting because I will literally have the audience sort of tell me what to launch. And so what ends up happening is they're like the co-creator in the product. So when the product launches, they feel like almost invested in the process and almost like an investor in a way. And so when we launch, it's like it makes total sense. And what's so amazing about the internet is you get that immediate feedback right away. And Michael, this, I'm going to play this clip over and over and over to you when I'm telling you about, I don't have like a roadmap of like all the

products I want to launch. I have to like feel the audience or the data, as you called it, and then adjust and pivot from there. That's right. That's right. And you will learn so much. Let me, let me translate this for folks who feel like they're listening and they're like, well, that sounds cool. But what if I don't have a gigantic audience? I started without any kind of audience. I mean, now I have some audience, but I had this really valuable realization in the very early days of entrepreneur.

And just to like explain myself here a little bit, so I am the editor-in-chief of entrepreneur, which is a job. Like, it's not my company. I'm an employee. But after 10 years of running this and absorbing the way that entrepreneurs think, how can you not also then become an entrepreneur?

So at this point, I now have a couple different companies and a whole lot. I'm like juggling a lot. And I think of entrepreneur as one part of a portfolio, basically, that I have. But at the very beginning, I had a media job. It was just, you know, I was a magazine guy. I run or edited a bunch of magazines, and then I came over here. And I was trying to think, who am I to this audience and what can I build for them? Like, how can I think of entrepreneur as both a place where I succeed, but also a platform for myself? And I started to listen to the questions that people would ask me, either out in the world or coming on a podcast. And what I realized was that if you listen to the questions that people ask you, you discover that what

you're really hearing is people telling you what they think your value is to them. Huh. And what I was hearing over and over again was a version, Michael, of what you just asked me at the very beginning, which is like, what do the most successful people have in common? And I thought, why is that the question that everyone's asking me? And I realized it's because people perceive me as a pattern matcher, because I have access to so many incredible people. So I need a good answer to that question. And if I can find a good answer to that question, then I probably have a product to build on top of it. The answer that I came to was the answer that I gave you 10 minutes ago, which was adaptability. I started to lean into that. What can I do with that answer? What can I do with that insight? Can I build

frameworks out of it? Can I teach it? I wrote a book about adaptability that led to a really robust speaking career where now I travel and I speak to companies about adaptability and thriving and change. And now I've built other things on top of that. That's like the core of my social media and my newsletter and all that. All is rooted in basically data gathering. What are people asking me? And then what is that revealing about how they perceive my value? Very smart. How do you thrive and change? Well, the starting point is that you have to develop what I call a unique personal relationship with change. You have to understand who you are in times of change. And I believe that most people, if not all people, have made this same mistake, which I have made throughout my career,

which is that you identify too closely with the output of your work or the role that you occupy, which is to say that if someone came up to you at a party and asked what you did, your answer would probably be some version of like, I do blank at blank, right? I do role at company or something like that. And that's fine, but the problem is that that is changeable. Even if you stay at your company your entire career, that way of doing that work and the role that you hold will change. And when it changes, it feels like a challenge, not just to your work, but to your identity. And that's scary. And that forces us to hold on to what came before. So we need to do is reorient our identity towards the thing that does not change in times of change. The starting point for that

is a challenge everybody to think of this for themselves is come up with a personal, come up with a personal mission statement for yourself in which it's a short sentence starts with I and then every word is carefully selected because it is not anchored to something easily changeable. So it is the difference between I am a magazine editor, deeply changeable, a deeply changeable sentence. Right now, as you and I are talking, my phone is on silent. My boss at entrepreneur, Bill, could be calling to fire me. You just could. That could happen at any time.

There's nothing stopping him. Don't do it, Bill. I appreciate that. And if he calls me and fires me, I'm not a magazine editor anymore. So that means my identity is dependent on one phone call, bad place to be. So here's how I think of myself. Seven words. I tell stories in my own voice.

And I really like that because the word stories, again, every word carefully selected because it is not anchored to something easily changeable. I tell stories is something I can do anywhere. I've done it with you. I do it when I advise companies. I do it on stage. I can do it in books, whatever. I control that.

In my own voice is me setting the turns for how I want to operate at this stage of my career. I do this exercise with senior executives and I hear really cool things. Like I help teams achieve greatness. I solve the most complex problems. There was this woman in Chicago at an event I spoke at who came up afterwards and she said, I built this consulting business. And then I put it on hold to stay at home and raise my first child. And although I am gratified by that, I do not know how to think of myself right now

because I don't identify with the phrase, stay-at-home mom, even though that is literally what I am right now. And the mission statement exercise helped her get to, I help people become the best versions of themselves, which applies to consulting and to raising a child and to anything that comes next. Very, very smart advice.

So you don't get so attached to the identity. Because that makes people anxious, I would think. Makes people super anxious. Out of all the people that you've interviewed, you've interviewed, Ryan Reynolds, The Rock, Jimmy Fallon. You mentioned Gary Vee. You also interviewed.

I don't know if you've been interviewed yet, but you've interviewed. Going to. Yeah. In the near future. Put that one at the top of the list. Absolutely. What are some takeaways from all these incredible people? Maybe you could give specifics.

Yeah. Yeah. I've learned so much from all of these people. Where to start? I'll start with Jimmy. Okay, so I interviewed Jimmy Fallon for the cover of Entrepreneur Magazine. It's typically why I'm interacting with these folks. And I went to his office, which is super cool.

It's in 30 Rock. And we spent, I don't know, an hour and a half or two hours or something talking. And by the way, I did the mission statement thing with Jimmy. And his answer was really interesting. He didn't follow the exact format. But he said that his mission statement is asking, does this bring people joy? And that's the filter through which he used. Right.

Smart. Yeah, which is great. Right? Because, by the way, the mission statement thing, I should have just said is the Point of it is that then you discover that you have transferable value and that anything that changes is just a new opportunity to do the thing all you already do best. I think that's really solid advice what you said. Thank you.

Yeah. So anyway, I talked to Jimmy for a long time for this magazine profile. And at the end, I'm leaving. And he says, he was like, hey, it was great talking to you. If you need anything else, if you have any follow-up questions, you just want to talk a little more. Like, just reach out. And I said, I appreciate that, Jimmy. I am not going to do that.

Because you've already given me so much of your time. And I really, I interact with a lot of very busy people. And I want to be super respectful of their time. Because I'm busy. Jimmy Fallon's busier. Oh, can someone, can you teach a class on that? I would be glad to. It's really important.

The number one thing that people want is for their time to be valued. No, I think it's just like. Like a little quick tangent, I think what's frustrating is when you do give someone time. Yeah. And then they abuse it. Yes. Like, we're wasted. Uh-huh.

No, meaning like, like, I'll give you an example. Hey, I have, I can do what you're asking of me. Like, I can go get coffee. Sure, you can pick my brain from three to four. And then at four o'clock, they're still talking to 4.15. And then it turns into 430. And then they also want to know if can you call their friend and give them advice. It's like, it's almost like an ask, but like a sandwich with like another ask and another ask.

Yeah, yeah. So I appreciate that. If you give a mouse a cookie. If you give them a cookie. That's what it is. We read that to our kids. Yeah. That's why that book is so successful because that's what people do.

If you give them something, they ask them more. Yeah. The giving tree. Yeah, you have to be careful. Right. You have to have boundaries. Okay, so I like that. Which is really important.

By the way, people are afraid to draw boundaries because they're uncanny. comfortable saying no. No is a gift. Remember that. No is a gift because most people will either ghost you or they'll say, oh, maybe some other time, then they'll just do that forever. Or they'll say yes and then they'll mail it in or do a crappy job. Like, if you say no to somebody, you are giving them a definitive answer. You're allowing them to move on. People thank me when I say no to them. You're good at that. Well, by the way, and this is like, I don't know, like I also think it's good to let people go in an organization that shouldn't be there quickly. And my perspective is, of course, you want to keep people employed and you want that a job. But if it's not the right

fit, I think it's selfish sometimes for people to avoid that confrontation and maybe drags them along that they know they're never going to give opportunity to that are not going to advance. And you're wasting their time for them to go find the thing that is the right thing for them. You're talking about. Yes, 100%. You absolutely are wasting their time. That's why I never feel bad letting me go because if I know that I look at it as like I know I'm going to be saving you time and creating maybe a better opportunity for you in the future. Is this how you broke up with girls? Yes. I'm so, I'm so glad you said that. I could see you break. I could actually see you breaking up with a girl like this. Well, I didn't break up with like, no, but I look at,

I look at this as, I look at as, well, that's a good topic too for dating. Yeah. It is selfish to string someone along that you have no intention of being serious with. I'm still stringing people along and I've been married for 10 years. We all know people that do that. I was just going to reveal myself as someone who did that. Like that is what I was thinking. I mean, we'll, I guess, eventually get back to Jimmy Fallon. But like, I started dating a girl's sophomore year of college. And then we stayed together for nine years.

And, you know, I just, I had done this thing that people do, which is that I got comfortable in this relationship. I knew it wasn't ultimately the right one, but you get into these things. Well, why would I break up when it's like fine? And you just stay. And at some point in that journey, my mom said, to me, if you are not interested in marrying her, you are wasting her time. She's just getting, she's just getting older. You're getting older. Like, stop wasting her time. And that haunted me.

Like, that was so true and it haunted me. And she was right. And eventually we did break up. And I think that that same lesson applies in business too. Don't waste people's time. Go back to Jimmy. We had to do a little caveat. Yeah, right. I also think in hiring, too, if you're, dragging someone through an interview process that you, I don't think that's good either. No. Don't waste people's time. Okay, so Jimmy Fallon.

So I said, Jimmy, you've already given me so much time. I don't, I'm not going to take any more. And I left and I went home and I started to write this piece. And I got to the final act of this profile that I was writing of Jimmy. And I realized, damn it, like, there is one other thing that I really should have asked Jimmy. Like, he made a point. And if I could just ask him a follow up, the ending of this story. would be so much better. And I agonized over it. I was like, I promised him that I wouldn't waste his time. And I don't want to waste his time. But also, this piece will be much better if I just waste his time. And so I reached out and I was like, Jimmy, can you get back on the phone? And a week later, I'm back on the phone now with Jimmy Fallon. And I'm on the phone with Jimmy Fallon. And I start by saying to him, Jimmy, I am so sorry that I have to take more of your time. Like, I, I'm on the phone with Jimmy Fallon. And I start by saying to him, Jimmy, I am. I am so sorry. I have to take more of your time. Like,

I told you I wouldn't do this and now here we are. And he said, are you kidding me? He said, whenever I enjoy talking to someone in an interview, I always make that offer to reach back out if you need something. And nobody ever takes me up on it. And you did. And what that tells me is that you are thorough. And thorough people are the people I want to talk to. You want to get it right and you want to create something great. And that's why you ask for more of my time. And I see that as an additive. And the reason I am telling you that story is because that jolted me, because it made me realize that a lot of the things that we may have told ourselves are bad are actually good. And we don't know unless we've tested them out in the real world. We're carrying around all these assumptions

about what we should and shouldn't do and what's good and what's bad. And we may be wrong about that. And in this case, because I went through my own barrier, I discovered that Jimmy Falun. thought well of the thing that I thought ill of. And that means there's got to be a lot more like that out there. Quick break to talk about AGZ. Yes, you heard that correctly. It's not AG1 that I'm talking about today. It is AGZ. Not that I don't already have my morning routine down pat with AG1, which I've been taking for years now and that we've talked about on this show for such a long time. But now I'm so excited to talk about this groundbreaking new product that they have called AGZ. AGZ is a nightly drink that helps you wind down and rest up. It's a melatonin-free formula with clinically studied herbs, adaptogens, and minerals. I cannot be more excited about this because for years now I've been starting my day every single day with AG1, but now I can also wind down and set my night up for success

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with milk or water, whatever you want. And AGZ is one of the few sleep supplements that contains both magteen, magnesium, L3a, and saffron, two high quality ingredients at amounts supported by research that together support the bodies need to calm and ease into natural sleep. I highly suggest pairing AG1 in the morning with the AGZ at night. Of course, we've got an incredible offer for you. If you're ready to turn down the stress and focus on the rest, head to drinkag1.com slash skinny to get a free frother with your first purchase of AGZ. That's drinkag1.com slash skinny. Everyone is spending so much money on skin care and hair care, but I feel like there is something we're not talking about. And that is the water that you're showering in,

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So all of these things I wanted to just deal with. So like I said, I switched. Jolie's filtered shower head is amazing. It's best in class. It removes chlorine and heavy metals. Jolie is a beauty wellness company that purifies the water we shower in for better skin, hair, and overall well-being. It also has a beautiful sleek design, so it's really like the perfect combination of form and function. Jolie will give you your best skin and hair guaranteed.

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And ever since we've figured out that Branch Basics makes a better for you cleaning alternative that does just the same thing, if not more effectively, we have not looked back. We made the switch and we feel good about it. Why would you want to have harmful cleaning chemical supplies in the house that can wreak havoc on your system, your loved ones, your kids, your pets, especially if there's a product out there that's a better alternative with healthier ingredients that does the same job. From countertops to bathrooms, even tough stains, Branch Basics all-purpose cleaner, bathroom cleaner, and their new stain removal tackle it all, plus their gentle on sensitive skin and safe

for babies and pets. So check them out, like I said, once you make the switch, you won't look back. Shop Branch Basics and 600 plus Target stores nationwide or Target.com. You can also use our code Skinny 15 to get 15% off at Branchbasics.com. slash Skinny 15, again, Skinny 15 for 15% off at branchbasics.com slash skinny 15. One of the topics that comes up on this show from time to time is hustle culture. And I'm wondering in your interactions with entrepreneurs over the years, have you ever encountered like anyone where hard work and hustling are not part of the criteria?

Meaning like how much do you really need to hustle and work like that in order to get ahead? Like, is that, are there people that can do it without that? Or is it the barrier to entry? Well, so I think that hustle means too many different things to too many people to have one answer to it. When we talk about hustle culture, I think we're often talking about like hustle porn, right? Which is just people rise and grind in on social media and they're just constantly showing off how much they're working and they're bragging about how little sleep they're getting. Like, dude, you need sleep. Like sleep is a good thing.

I get plenty of sleep and I also juggle a lot. So I don't think that performative hustling is good for anybody. I think that that is a narrative that has been told and has gotten some people ahead, but that it is ultimately not all that productive. I do think that if you're going to build something, you need to work really hard, harder than you think you're going to need to work, and you're going to have to make sacrifices about how you spend your time.

Like to me, hustling is not a word that I identify with, but prioritizing is a word that I do. And being intentional is, I mean, you guys, I'm sure are very, very well aware of this as parents, as I am of a 10-year-old and a six-year-old that when I had kids, I was really worried that I'm an ambitious person, I have a lot going on, that I was not going to have the time that I had before to grow the things that I was. wanted. And I will tell you what happened, which is that over the last 10 years, as long as I've had children, my career has significantly accelerated. Why is that? The answer is because I've become, I've been forced to be more intentional with my time. Totally. We just talked about this. Totally. This is such a good conversation. You are forced as a parent to be more intentional because you don't have as much time before, which is, it's weird. Yeah. But it's right. Yeah. But it's right. yeah, you know what it is? Time, this is a weird metaphor, but it helped me. Time is like a balloon.

So when people think about doing something new, trying something, you know, maybe you start a side hustle, see if you can become an entrepreneur, what people often say is, oh, but I don't have the time. Oh, I don't have the time. But nobody has the time, right? Nobody's walking around with like three free hours in the day. I'm not, you're not. So how do we add things? Well, similarly, you don't, how do you inflate a balloon?

You don't make space for the air in the balloon and then blow air in. That's not how it works. You just blow air into the balloon and it expands because a balloon expands under pressure. Time expands under pressure the same way, which is to say that if I add something to my busy and constricted schedule,

because I've got family time that I will not bleed into, then what happens? What happens is that it forces me to reconsider everything else that I'm doing and ask, is this commitment still really moving the needle for me? Could I be doing this other thing in a more efficient way? Is it time to add a team member to that thing so that I'm not doing that and somebody else is? Time expands under pressure. You add more things and then you reconsider every other thing that you're doing.

and some things are going to have to go. I have killed projects that I loved because they weren't advancing me far enough and there were other things that were going to take priority. And that is just what it means to prioritize and grow. And to me, that is healthier than like hustle. Yeah. No, I was curious on how you thought about it was a great answer.

You've seen a lot of mistakes as well. Yeah. From maybe companies that are started or founders. What are some of the most common mistakes where maybe a company gets an initial buzz is doing well and then crumbles. What do those look? I think one of the biggest mistakes companies make is that they're not actually talking to their customer. They think they're talking to their customer, but they're actually talking to themselves

and they're not. So a story brings this to life. My friend Rochelle DeVoe is a Consumer Insights researcher. She gets hired by companies to go and survey consumers and understand what they're all about. And she was once working for this company. She tells this story publicly, Vim and Vigour. They make compression socks. And they were started by an athlete who couldn't find a compression sock that she loved on the market. And so she made her own compression sock company for athletes. And the company started growing and it kind of flatlined. Couldn't figure out what was wrong.

Hire Rochelle. Rochelle goes out and talks to the consumer. And then comes back to Vim and Vigour and says, have information. And that information is this. You have made a company for athletes and you're marketing to athletes, but your best customers are not athletes. They're not. They're like nurses and teachers and people who have to work on their feet all day.

So you are succeeding despite yourself because you're talking to the wrong people. And so Vim and Vigor changed. If you go to their website now, the first thing you'll see is a photo of like feet in dirt withholding like a rake, you know, very far away from athletes. Because they weren't in touch enough with

at that stage of their company, they're a consumer. And I see that over and over and over again, where I'll talk to a founder, maybe somebody I advise, and they're under, they're not clear why the company is stalled, or they're not clear about how to make a certain decision. And I'll start asking them questions about what their customer responds to or what their customer values or what problem exactly are you solving for your customer. And they can't articulate it because they're talking to the customer. So you need to do that over and over and over again. And I see way too many companies think the CEO is like, well, I just know. I know. I built this company. I know what it's for. No, you don't.

You don't unless you're talking. What do you think is a good exercise for someone who wants to launch a business now? Like, what's, is you have like a vision board? Like, what do you start with? You start by talking to people about their problems. Like, the, The major mistake someone makes at the very, very, very beginning is that they have an idea for something and then they have to go around convincing people that it's useful. So you have to flip that. You have to instead talk to people about their problems and then find a problem to solve and then build it with them.

So there's nothing more magical, truly, than finding a problem, even a small set of people and then saying, I will build this for you, but I'm also going to build it with you. you. So you're now my customer advisory board. And I'm going to build this and I want to bring it to you and I want feedback so that I can make it even better. And if you create that feedback loop based on a problem that you solve for people, you guys had Donald Miller on the show. I love Donald. Great guy. Great guy. You know, his whole thing is about communicating the problem that you solve. That's the core of marketing and messaging in a business. Like you have to be able to articulate to people, what problem do you solve? As Donald said, everyone wants one of two things, to survive or to thrive,

or both. And so you have to communicate that. But at the very, very, very beginning of conceptualizing a business, you still have to do that. You still have to find the problem that people already want to be solved, and then you solve it. And then you're already valuable. You cannot go around trying to convince people of something that they don't understand. That is a wasted effort. I also think that if someone asks you what your business is or what you do and it takes you 10 minutes to explain, we got to go back to the drawing board. I always tell like if I'm mentoring someone, it's like how do you explain your business to an Uber driver in three seconds? Yeah. Because it should be that tightened up with a bow on it.

I'll give you a formula for it. If you want to sell anything to anybody, then you have to be able to fill out the follow. Madlib's style sentence from their point of view. Good idea. I love Madlibs. What's what is it? Also I picked this up from my friend Rochelle. So shout out to her. When context, I want solution so that benefit. Let me break it down. So when context, when there's a problem, I want solution, I want something that solves that problem so that benefit so that I get what I actually wanted in the first place. So if the three of us started a company

selling Zit cream to teenagers, then the way in which we would articulate from our consumers' point of view, that sentence could be, when I have a big pimple on my forehead, I want something to get rid of that pimple as fast as possible so that I can get to school more confident. Now, the reason to go through this exercise is because most people stop on solution. They talk about the solution, the thing that they've built, the thing that they spend, all their time thinking about how to create and market and all that stuff, where solutions oriented people. But the problem is, nobody cares about solutions. Nobody. They do not care about your solution. What they care about is benefit. They care what they can get from it.

And so if you can articulate that in their language, from their point of view, they trust you. So if you're trying to sell to teenagers, don't start talking about the chemicals in your zip cream, they will not listen to you. But if you start by talking about getting them to school more confidently, now they think you understand them and they're on board with how you're going to do that. Really interesting. Yeah, just listing all the features and functions you lose people. You know what? He would be a good speaker to your company. Like, I feel like, and I think you do that. Yeah. He would be a good speaker to come in and talk to your media and stay confidential. Thanks. It's interesting. Like, you know, we have a nice audience. I mean,

it's a wide audience at this, we're doing a long time. And whenever we're having conversations around entrepreneurship, I'm always hesitant, like, how to title them. Because I think sometimes see entrepreneurship, and they kind of say, like, well, that's not for, like, there's some segments, like, that's not for me. I'm not an entrepreneur. But there's so many messages in this topic

that are universally applicable to anyone in any stage of life or with any kind of thought process or function. Do you get what I'm saying? Yes. It's not just this narrow box of like you're an entrepreneur or not. There's a lot of lessons in here for life in general. Which is, that's why when Lauren asked me how I define entrepreneurship, I define it as someone who makes things happen for themselves. But that, that thing that you just said there, like, don't breeze by that because what you just said is really important for anybody making anything, which is that you are anticipating what I call the first question. The first question anybody will ask about anything that they ever encounter, whether it's something you made or elsewhere, is, is this for me or is this not for me? And you have to anticipate that they're going to ask that question. And then you have to answer it before they ask it. That's the only way to connect with people.

So, like, just think about it for yourself. You go on to Netflix. Everything that you're seeing, you're just like, is this for me? Is this not for me? Is this for me? You're walking down Whole Foods. Is that for me? Is that not for me? Like, we're asking that all the time, but we're not often proactively answering it. It's interesting that you say that because if you look at Netflix and you look at Instagram, there's a for you page. That feels like very strategic that they called it that. Yes, absolutely. They're signaling for you. Yeah, that's no accident that it's called For You. Even they have that on Netflix too.

I noticed that. I love like looking at the little hidden messages like that. And thinking about how that is the product of a market. Like this is, I love seeing that kind of stuff out in the world because the reason that that's on Instagram and the reason that that's on Netflix is because that was A-B-tested to death.

And that was the language that worked. And that tells you a lot about what works in other mediums. You know what you should title this episode? I swear, for you. your guide to like starting your own business. You should title it for you. No, but it's so interesting. I mean, like, we're going in the niche of like podcasts or YouTube show titles, but that's the whole thing that you're trying to do is you're trying to create the title that signals that this is in fact for you and not not for you. Right. What entrepreneur advice did The Rock give you? Because he's built quite the impressive octopus of a situation.

Oh my God. A very impressive octopus of this situation. It's funny because the memorable, that was a weird metaphor, but I'm going to roll with it. His metaphor to me was when I asked him about the mission statement thing, as you can see, I kind of love doing that with people. He said, I am a 10-lane highway moving through the world, which is a very intense thing to think. Jesus Christ. Oh, God, Michael loves it. So here's what I learned most from the rock.

First of all, super nice guy. Have you talked to him? No. No, I'd really like to have him on the podcast if he wants to go on. Open invite. Yeah, open invite. Anytime. Antoine, Duane.

Super nice guy. Really smart, really thoughtful, really listens. And so we had a nice conversation with him and his business partner, Danny Garcia. And then we talked about a whole lot of things. It was great. But the thing that stood out was what happened afterwards, sort of like Jimmy. So I interviewed The Rock. And then a year later, I write this book.

And I include in it. a single paragraph of something that I learned from The Rock. And when the book comes out, I ask his publicist if I can send him a copy. I do not think anything is going to happen here, but I just wanted to send him a copy. And she gives me an address, I don't know what it is, an office or something. And I put the book in the mail and I send it off, and then I forget about it. And then nine months later, I open Instagram, and I've got a DM from The Rock. And it's a voicemail.

And I hit play on it. And then there he is. And he says, hey, Jason, what's up? It's DJ. That's how he goes away. He's like, it's DJ here. I just wanted to tell you, man, thanks so much for sending me the book. And thanks so much for including me. It really means a lot. And then he, like, reflected on things that we talked about, which at this point was years earlier. And the whole thing was 52 seconds long. And it made me feel like a champ, you know? And here is the lesson that you should take from. The single easy, and greatest thing that you can do to make a fan or a customer for life is to respond to them. People do not respond enough. You email somebody you never hear back from them. I don't know why. Responding, I get a lot of DMs, I get a lot of emails. I respond to you literally everybody. It takes me a while, but I do. And when I do, what I hear back is, oh my God, I never thought I'd hear from you. And then sometimes years later, somebody will say, you know, I just bought that thing.

of yours because years earlier, you responded to me. It matters so much because the one thing people want is to feel heard. That's it. If you can make people feel heard, you have won them over as a customer, as a fan, as a friend, as whatever, as a partner. And if Dwayne the Rock Johnson, surely one of the busiest people in the world, can spend 52 seconds sending me a voice memo just to make me feel good, then you can do it for any. I also think there's a savviness to that that he knows that that 52 seconds will then be on a podcast. Do you know what I'm saying? And I don't mean that he did it like out of that.

But I think he's smart enough to understand that you are going to go do your own octopus with that 52 second voice, which you have. Do you know what I'm saying? Yes, absolutely. Like he's smart enough to know that it's like it's worth his time. it means a lot to you. Like he understands it from a 360 approach. It's a situational awareness. Yes.

It's a win for everyone. Right? Like you felt good. He gets spoken out nicely. He gets to also be a good person. Yeah. Acknowledge your book. It's a win-win.

It's a win-win. What has Gary V taught you? So I've known Gary V. A long time. But the most memorable thing that he has said to me haven't. Okay.

So I don't know. This could have been eight, ten years ago. Gary reached out and he said, let's get a drink. Is it all right? Did he give you seven minutes? Yes. No, he didn't. Not seven minutes, but it was like that. It was like a super specific amount of time at a super random time.

You know, it was like, I'll see you from 815 to 8.37. It was so random. Did this happen to you too? I just know he does this. I just know he does this. Go ahead. So we have had that happen. to us with him. Not with him. No, we have. We went on a show early, early days.

It was a very, it was a very specific amount of time. I just know how he is with his time. So go ahead. Yeah. I asked him, Gary, how do you generate ideas and know what's going to connect with audiences? Because that's something I do as well, and I'm always interested in how people do it. And he said, he's like, I have a system. And the system is functionally a system of graduating ideas through the ecosystem. So, you know, back then it was Twitter, not X. So he's like, the first starting point is Twitter. He's like, as soon as an idea pops in my head, I just tweet it.

And that is basically a market test for ideas, which ones get reactions and which ones don't. And the ones that get reactions, he might expand upon, might have it turn into a longer, you know, post on LinkedIn or Instagram or something like that. And then the ones that generate a lot of attention, maybe he'll go on a rant on on a podcast somewhere. And he's just kind of constantly graduating his ideas through his ecosystem. And I started to do a version of that too. And it works. I mean, more or less, everything that I've said to you is in some way or another, something that I've pressure tested in the market.

Like, it was an idea that started somewhere that maybe I started on LinkedIn and then people responded and then I like wrote about it in my newsletter and that worked and then I said it on a podcast and maybe I've said it on stage and I'm refining how I say it and how I think and then I'm adapting to the individual experience but that's the way to develop ideas in a low stakes environment and make sure that they're ready for a more high stakes environment and that was an incredible lesson. Was it literally seven minutes that he gave you or was no it was more than that. Okay, it was a little longer. Yeah. He let you have a drink. It's now not some flimbinger the idea that, you know, someone pushes back on just a little bit and the whole thing

falls apart. Like you said, it's been pressurized totally by getting this kind of feedback and all that kind of refined. He's got, he's got the data like you said earlier. He's gathered it and so he can know what's going to hit. He knows what his, he, everything is a market, you know? Like, everything is a market. And so you can test ideas in a market too. And you can see, do people respond to this idea? And if so, then let me lean into it more and develop something that's even more meaningful for people. If you listen to me on the toast with Jackie, you know I do not mess around when it comes to a diaper wipe. I do not screw around.

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and we have a code for you. You can use new, new at checkout, and you will get 20% off. Use the code new new at checkout to get 20% off. Shop skinnyconfidential.com. Out of all the newsletter topics that you've done, what has been the one that's sticky, like what he said? What is stuck? Of my own? Yes. I wrote this newsletter a couple years ago about how to figure out the problem you're actually trying to solve.

And it was like the number one thing. People keep coming back and referencing it to me. So I'll tell you the story and then the framework that came out of it. So there is a advert, there was a young advertising guy who booked a call with me. I do these one-on-one consulting. And he said,

he's like, I work at this agency and I cannot get my ideas through. I just can't get them through meetings, but they're good ideas. And so the thing I want to ask you is, should I just execute my ideas without telling anyone, because then they'll see how good it is. And I said, no, like, don't do that.

But instead, what you need to do is you need to figure out what the actual problem is. So we see the result of a problem, which in his case is that he's not getting his ideas through. But he doesn't actually know what kind of problem he has. So here's what you do. Whenever you are facing a problem, you aren't sure how to diagnose it,

try to come up with a whole bunch of hypotheses for what kind of problem you have and give each of them a single word name. So for example, this guy could have all sorts of problems. He could have a articulation problem. He has good ideas, but he doesn't know how to share it. He could have a teamwork problem where actually the way to get ideas through with his organization is to partner up with other people and he's going solo. He could have a hierarchy problem. where at the company that he is, people just don't listen to the junior people. And so you're going to have to work with the senior people.

He could have a visualization problem where his ideas are too complicated to verbally communicate and he needs to start coming up with better visualization. The reason to do this is because then, once you have identified every kind of problem, you can start to experiment with solutions for those problem sets. Right? Like, when it's just like, people aren't listening to me.

You don't even know how to begin to solve that problem. But if it is a visualization problem, well, what would be a solution to that? Try making some visual. See what happens. Is this a hierarchy problem? Start trying to partner up with some more senior people. See if that moves the needle. You can start running down the list and seeing which of these is actually my problem.

Because once you figure out what your actual problem is, you can solve it. I think the vast majority of people, when they're trying to solve a problem in business or just generally speaking, are coming at it too broadly. They're looking at it as a giant soup and they're not breaking down what the actual problem is. And the only way to do that is to run through like a whole set of hypotheses. So the next time that you or I have a problem, we're going to just make a list together on a poster board. What is my actual problem? The list is going to fill up. No, we do this a lot in the sales organization.

Like if someone says, we're not closing sales or like I didn't close a deal. It's like, well, we diagnose why. Like, is the messaging wrong? Is the pitch wrong? Did you reach the wrong person? Is the product not good? All these things. And it's funny in the world that we live in and like just call it in podcasts in general.

If someone starts the conversation with Dear Media and the first question is like, well, how do I make money? I'm like wrong problem. Right? Like more like how do you create something that people deeply care about? Because does that make sense? Yeah. Well, you'll make money when you have a solution that someone's willing to pay for. Jason, we have some rapid fires.

Okay, hit me. I'll let Michael start. biggest entrepreneurial myth. The first thing I was going to say was something that you just said a second ago, which is you're going to make a lot of money. You're not going to make a lot of money. Maybe you will, and that would be great. But you have to do this for something other than money.

You have to do this, I think, because you want autonomy and because if you can do anything else, go do that. This is what I always tell entrepreneurs. is if you can do anything else, go do that because it's easier. So the reason to be an entrepreneur is because you literally can't do anything else. That is the only thing that will keep you in this path. One trend in entrepreneurship that you think is here to stay. The obvious answer is social media, which is so boring. But the more nuanced version of that is that if you are not putting yourself out, as a face of anything that you've built,

then you are missing an opportunity, and that opportunity is here to stay. People connect with people more than brands. Your story is the largest asset that you will have, especially in the early days, that is never going away. You have to build yourself as someone that people can connect with.

Most underrated skill every entrepreneur should master. Level-headedness. That's a good one. I am, I'll tell you, I cannot tell you too many details about this, but literally after this taping here, I am hopping on an extremely high stakes call with a founder who I have been on the advisory board of his company for five years. He has a massive, massive investor who is so close to a deal. And the investor kind of changed the terms on the deal with him last minute.

And he called me up a couple of days ago, and he was freaking out. this is so disgusting and they're trying to take it. And I was like, dude, if you get any hotter, you're going to blow this and you're going to lose the whole company. So I, I'm just a non-emotional person. I was like, I'm going to join this call and you're going to introduce me and I'm going to, I'm going to be a part of this conversation with this investor and we're going to save this deal. Like, he is too hot. And that hotness is going to make him lose things. You have to treat everything, everything as if it is just one part of a much longer story. Everything that happens today, tomorrow is just one random bump along a far longer continuum.

And you cannot think of what happens today as that important. It's not. It feels important. It is important. Whatever. It's not that important in the grand scheme of things. When Netflix tried to sell itself to Blockbuster for, $50 million, which is a thing that happened, right?

People forget that. Yeah. Reed, Reed Hastings and Mark Randolph walked into Blockbuster and tried to sell that little startup Netflix to Blockbuster for $50 million. And Blockbuster laughed them out of the room. And those guys could have thought, Netflix founders could have thought, well, gave it a good shot. Like, that was the end.

You know, we failed. But instead, they built a multi-billion dollar business, transformed in industry. And now you look back on that moment and you say, well, that was fun. You know, like that's the only way to think about this stuff. I don't think those blockbuster executives. No, they didn't think it was funny. Remember when you had to go rent the Netflix from the, the kiosk? Yeah, but you know, like we're old enough to, I remember going into the blockbusters and getting

the VHS. Nothing better. That wasn't, nothing better. You get some candy when you were in line. Grab a couple. My dad devastated me because I got to watch Star Wars, the original Star Wars. Oh my God. He talks about this every day.

Ph.S. And I was like, dad, we need to go see. I was like, there's three of them. He's like, yeah. And I was like, okay. So he took me to Blockbuster. And they were missing the Empire Strikes back. And he's like, cool, we'll just grab Return of the Jedi.

No. So I turned, I went from Star Wars to Return of the Jedi as a kid. And I was so lost and confused. And I feel like that's a devastating moment. To be honest, too, that has set off a chain of events for your entire life. Because now if anything's out of order, like he can't take it. And I'm realizing it's all from your childhood Star Wars. My daughter tried to watch like Harry Potter four the other day, but she hadn't seen three.

And I was like, you're not doing that. I was like, don't know. I'm like, yeah, right. I support this. No, and then when is the other one, it was like, I don't know. But yeah, I will not allow it. I'm like, listen, I'm saving you from what the, you know, the neuroses that exists now. Jason, where can everyone find you?

Subscribe to your newsletter, listen to your podcast. Yeah. To view me on the cover of Entrepreneuram Magazine. I know. I'm excited to see it. So, all right. At the risk of, so there's this thing called the tyranny of choice, right, which is that if you give people too many options, they'll choose none of them. And I'm going to violate that right now by giving you three things, but hopefully at least one is relevant.

So number one, you mentioned my newsletter. I appreciate that. It's called One Thing Better. Each week, one way to be more successful and satisfied and build a career or company that you love. And you can find that at One Thing Better. Email. That's a web address, plug it under browser. One Thing Better. Email comes every week. And by the way, I said about replying with Dwayne the Rock Johnson, if somebody replies to that news like, if you heard something on this show that you liked or didn't like, reply to the newsletter, it goes to my inbox. I swear to God, I will reply to you. That's cool. Number two is if you're building a consumer package goods brand. So, you know, snacks, beverage, cosmetics, I have a company called CPG Fast Track where we help early stage consumer package goods founders grow, basically giving them the network that they don't have at the very beginning. So go find CPG

fast track and get in touch. It's a great service. I built it with a couple other friends who have built incredible brands. Does it help you basically find the resources to build the products that you want to build and put you in touch with the right kind of packages or producers? Yeah, exactly. So it's a, so when you join, you get put into a small group that meets twice a month of founders at a similar stage. And your small group has a leader who is an experienced CPG founder. So I'm working with my friend Lisa, who's the co-founder of Little Spoof Children's brand, Marcus, who was the founding team of Four Sigma, Dave from O2 Hydration, some other folks, like incredible.

So you have the small group, and then we just bring in amazing operators, the head of marketing from Liquid Death, the head of partnerships from OliPOP, founders, and help people just give these really interactive sessions. It's like, we had Donald Miller, actually, and he started creating on the spot Donald Miller, who wrote building a story brand for those who don't know, incredible brand marketer, started building on the spot taglines for our members. It was awesome. That's cool. So anyway, so yeah, and then there's a bunch of other stuff, but that's what CPG fast track is. And then finally, Help Wanted, which is that podcast that I host with Nicole Lapin, where we talk about

sticky work problems. And we want it to feel like work therapy. So if you've, if you're going through hard work things, if you're trying to build something, or if you're trying to advance your career. We tell you what we have really struggled with ourselves and we bring on callers who have their own struggles and we try to help them. Jason, thank you so much for your time. Pimp your Instagram out real quick. Just tell us where to find you and say hi. Okay, sure. Yeah. It's at Hey, Fiverr, H-E-I, F-E-I-F-E-R, or find me on LinkedIn, Jason Fiverr, which is actually where I'm more active. Guys, such a play. Like, I am so delighted that you had me on here and this is fun. And this was different. We've been doing these. We've been batching them this week.

And go listen to me on our. entrepreneur on your podcast. You interviewed me. I also was a podcast with entrepreneur called Problem Solvers, which is far more like build a business specific. Had you on, Michael, you're about to be on. We had really, really great. You and I talked about building the audience before the brand. You're going to give me case studies about how you guys are like building incredible brands here at Dear Media. I'm really excited. Thank you. Thank you, man. It's great. Thank you.