The Skinny Confidential Him & Her Podcast - What It Really Takes To Build a Successful Brand & Business - From Scratch To Scale With Michael Bosstick

Episode Date: August 18, 2025

#877: #871: In this raw and unfiltered solo episode, Michael Bosstick breaks down what it actually takes to build, scale, and sustain a business in today’s world. Drawing from 20+ years of firsthand experience as the Founder & CEO of Dear Media, an investor in high-growth startups, and a serial entrepreneur, Michael shares hard-earned lessons from both wins and failures. He dives deep into the biggest mistakes new founders make, how to choose the right business partners, the importance of financial discipline, and how to protect your energy while building something that lasts. Whether you're launching your first company or growing your tenth, this episode delivers tactical insight, mindset shifts, and a no-BS playbook for long-term success.   To Watch the Show click HERE   For Detailed Show Notes visit TSCPODCAST.COM   To connect with Dear Media 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].   To learn more about DM IRL Dallas and purchase tickets visit https://dearmedia.com/events.  This episode is sponsored by Cotton Cotton is The Fabric of Our Lives. Learn more at http://TheFabricOfOurLives.com.     This episode is sponsored by Fatty15 Fatty15 is on a mission to replenish your C15 levels and restore your long-term health. You can get an additional 15% off their 90-day subscription Starter Kit by going to http://fatty15.com/SKINNY and using code SKINNY at checkout.   This episode is sponsored by Astral Tequila House Marg Summer is here!!! Time to stock up! Go to http://AstralTequila.com to find Astral near you - and don’t forget the limes! Please Enjoy Responsibly.   This episode is sponsored by The RealReal Get $25 off your first purchase when you go to http://TheRealReal.com/skinny.   This episode is sponsored by YNAB TSC Him & Her Show listeners can claim an exclusive three-month free trial, with no credit card required at http://YNAB.com/skinny. 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.

Aha! Hello, everybody. Welcome back to another episode of the Skinny Confidential, him and her show. today you have me, Michael Bostic once again solo while my wife Lauren is still on maternity leave. She will be back soon. But today I'm very excited to do a business focused podcast show because I haven't done one in a while. And obviously for the entrepreneurs or the career focused people out there or people that are thinking about starting a business, many of you come to this show for some of the business content.

And we have amazing entrepreneurs that come on here regularly. but I also have a thing or two to offer in the realm of entrepreneurship. For a little bit of background, for those of you that maybe don't know me, I'm sure many of you do, but for those that are wondering, you know, why is this guy credentialed to give us any advice? I've been an entrepreneur, basically my whole professional career. The last actual job I had where I worked for somebody other than myself was when I was 15 years old, working at McDonald's. It was great experience. But ever since then, I've always kind of done my own thing. I've started businesses. I've co-founded businesses. I do run and currently

run a business that I co-founded and started called Dear Media, which is, you know, the producer of this podcast and many others as well as many other things. I'm an investor in many startups and businesses that I've advised on. And, you know, I would say that I've had some luck and some success in the realm of entrepreneurship and business owning for, you know, the past two decades. So I've made a lot of mistakes. I've learned a few things. I've had some successes. But most importantly, I've made a lot of mistakes that I've continued to learn from and try to share with others so that hopefully they can avoid those mistakes or you can avoid those mistakes. So with that, today I have set up an episode all around maybe some pitfalls or mistakes

that early entrepreneurs or solopreneurs or people that want to own their own businesses make in the early days when they're starting a company or starting a brand or starting a business. I can say a lot of this has been through trial and air of me making many of these. mistakes and now me sharing them with you so that hopefully you can avoid them or at least think about them if you're starting your own business, your own brand, if you're a new entrepreneur, hell, even if you're an entrepreneur that is running your own business right now and maybe you're making some of these mistakes, maybe this can help you get on the right path. So again, I'm not going to say that I am the greatest business expert in the world because

I'm not. There's many people that I admire that are much further than me. But I have learned a thing or two over many successes over the years and, you know, building eight and nine figure businesses. So here we go. Let's jump into this solo episode. For those you then waiting for the business content, I hope you're excited. Okay, number one, and this is a big one, and it's an important one to talk about right off the bat, is mistaking self-employment for freedom, glorifying being an entrepreneur. I talk about entrepreneurship on this show a lot, so does Lauren. And I feel like being an entrepreneur,

being a business owner, being a brand builder is glorified these days. And it's great because there's a lot of people that have had a lot of success. But there's a lot of untold stories of people who have set out on their own, tried to do their own business, try to build their own brand that have had a miserable experience or have failed or have not had success going out on their own own. And I would just like to highlight that the majority of people that start their own business, their own brand, set out to be an entrepreneur. Most of those people fail, and I have failed myself at times. But the big thing to understand is like if this is a real passion, if you really feel like it's your calling, if it's something that you absolutely have to do and that you can't work

for anyone else, I always joke that even though I've learned a lot, I'm completely unemployable. I can't imagine, you know, working for someone other than myself. If you have that kind of drive in you and that perspective, then maybe you should. But here's the thing. Leaving your job and starting your own thing doesn't always equate to the freedom that many think it will, or think it that it will bring. And here's what I mean by that. Say that you are kicking ass in your company and you're like, you know, I really don't like this business. My boss doesn't appreciate me. I'm not getting what I think I deserve here. I'd be so much happier doing this thing on my own. You know, I could do it so much better on my own. That's a great perspective to have.

but now let's base it in some reality. Let's say that right now you are on a sales team at an organization and you are one of the best sellers and you haven't gotten that raise or promotion or your boss hasn't acknowledged you the way you want them to. That's a separate conversation. Let's figure out why that's happening in a different episode. But maybe that's going on with you. So you start to get the idea like, hey, I can go off and create my own company and I could

do all and I could sell all day long and I'll just kick ass doing this on my own and I'm going to build my own business. Well, now let me give you a splash of cold water. I'm sure you do that very well. But now you also have to start considering other things. You have to consider owning your own business, making your own payroll. As you hire people, what does HR look like? What is managing a P&L look like? Do you have investors? Do you want to deal with raising capital and bringing them on? Right now, you're only responsible for this one area of the business, which is sales. But now you have to build all the decks and you have to do all the pitch meetings and you have to manage the team members and you have to deal with being sued and you have to deal with managing people and you have

to also have conversations with people like yourself about managing their expectations and making sure that they're compensated fairly and you know as they push back and as for more greater raises managing that expectation and making sure you're delivering you know a fair result to them as the employer. So what happens is you become somebody who, you know, maybe you've been just kicking ass, like I said, and you're focused on one area of the business. Now you have to think about the whole thing. I talk to young people about this all the time. And I say, do you really want to go focus on the whole thing and be responsible for the whole thing? Or are you just in the wrong company? Or do you not have a different conversation with your boss? Like, do you really have a calling? Because I've

seen time and time again where people take something that they're very passionate about, whether it be sales or working with their hands or design or whatever. and they go and start their own business off of that passion quickly to realize that now you have to deal with all of the other things that you don't have to deal with if you are working in an organization. So, you know, for me, running Dear Media, I love to talk on a mic. I love to interact with people. I love all of those things. And I would say I like sales as well. But now I have to think about HR. I have to manage the culture. I have to deal with the P&L. I have to deal with all of our investors. I have to deal with production. I have to deal with all these headaches. And I have to also

make sure that everybody that works in the organization is getting what they need for me in the business. And so it's a real shift. I don't just get to sit down and talk on a mic and do that all day. I have to think about all the other things. So I guess this is me in a way talking some of you out of jumping into the entrepreneurial pool and asking yourself first if you're just unhappy at your current role, if you can make more money at another organization, or if you really, you know, have that drive to go off and do this on your own. And so, you know, it's important thing to consider I would say that another misconception about being an entrepreneur is that you get to control all your time and you get all this free time and less stress and that's true.

Listen, I set my own calendar, but I have less time today than I've ever had in my entire life and I'm arguably more quote unquote successful on paper than I've ever been. So it's just something to think about because when you work in an organization, you get to show up with your briefcase from nine and usually leave at five and you get to set hours and then clock out. If you're going to be an entrepreneur, there is no clocking out. If something goes wrong in the middle of the night, you're dealing with it. If something has to be done on the weekend, you've got to do it. If you're on vacation and something pops up in the company, you're dealing with it. There's no like, I'm out of office. You're always in the office.

You're always on call. Of course, you can try to set boundaries around it, but it's just not possible. Even though, you know, right now Lauren's on maternity leave and trying to take that time, she's quickly realizing that she doesn't get to just check out of the business or check out of company she actually has to stay involved all the time so you know there's there's pros and cons to both you know if you if you can make it work as an entrepreneur and you can have success it is the most rewarding thing in the world but it can also be extremely painful and i would argue that many people don't actually want to do all of the things that it takes to run their own business and their own company they sometimes just get frustrated with an area of their current job or employer

and then they start to look for something else and so really be clear that this is something you want to do. So a mistake, I guess to wrap it up would be mistaking self-employment and being an entrepreneur for freedom and glorifying being an entrepreneur when really you don't want to be. And the other thing I would say is there's a lot more number twos and threes and fours at other organizations that do a hell of a lot better than me and a hell of a lot better than most entrepreneurs make more money, have a greater career, more stability, greater happiness, all those things. So it's something you really have to want before you dive into it. That's number one. Okay, number two, and this is important. I see a lot of first-time business owners,

entrepreneurs, brand builders making this mistake, and it's not starting with the end in mind. It's kind of like, hey, I have an idea. I think it's kind of good. I'm just going to try that for a while and see what happens. No, this is really difficult for multiple reasons. The main one being is you don't have a goal that you're pursuing. So when I started Dear Media, for example, I never set out to just build a podcast business. I set out to build a new age media company that would aggregate a flywheel, which in our case happens to be focused on female demos, that would then have an advantage not only in media, but in commerce.

So when I thought about this great idea in my head years ago, I said, well, what if there was something that existed that married media to commerce, to investing, in brands, and you could service it all in one place for creators and entrepreneurs so that they could have a one-stop shop to do all of these things. This was really helpful because as we started the business, you know, you could get really led down the road of like, hey, what are other people in the podcast space doing and focus on that, which would take me off of my goal of, you know, marrying all the other engines and

commerce opportunities. Or you could start to say, hey, what are other typical VCs or commerce businesses doing, which would basically take my eye off of the content. And what happens when you don't have this kind of grand vision when you start a business is then when you get going, you can get distracted. and you can get pulled in 13 different directions. As you start anything, you're going to have all sorts of different voices, giving you different pieces of advice.

And a lot of that advice is great. The problem is a lot of that advice is also emulating what other businesses or other people or other companies have been doing to have success. So in my world, if I would have set this whole business up the same way that maybe a legacy podcast business set their business up, I would have missed so many opportunities. I would have been a second-rate version of those things. I would have had a really difficult time building our culture and our foundation, but because I was laser focused on the end in sight that I set for myself in the beginning, we've been able to stay disciplined

and focus on what we want to build as a company. The other thing is, say you're starting a business, and Lauren and I use an example all the time when you have a co-founder, or maybe you're doing it with your girlfriend or boyfriend or husband or wife or a co-founder, and one of you wants to build the greatest bakery in the world, and you just want to service this small community and the other partner wants to have a franchise and have hundreds of these bakeries. Well, now you have two people

that started with the kind of the same rude idea, which is bakeries, but at different scales because one has this end in sight and the other has a different end in sight. And now one or the other is better, but you have to make sure that whatever that end is, that everybody's on the same page. And so, you know, getting really clear

and caveat this with saying that there's going to be pivots and there's going to be things that you have to adjust and move along the way, which we'll talk about. But having a really solid idea of what you actually want to build and what the long-term goal is, going back to example one, maybe you're somebody that works with your hands and you're really passionate about that and you're working for an employer, but now you don't want you to start your own thing. Like, is that a hobby or do you actually want to build a business of that? And if you are building a business, like, what is the long-term goal for you?

Like, what is the end? What does 10, 15, 20 years look like? If you start with that far of a perspective out when inevitable problems arise, which they will in any business or hurdles, and you have that long vision, you're going to be able to stick with it, where if you don't and you're kind of like, let's see what happens, as soon as you get met with the first roadblocks, you're going to kind of give up and stumble and lose motivation because there's nothing greater to pursue or there's not a greater vision to pursue, I should say. So make sure when you're starting a brand or a business that you really have thought out the end in sight and work backwards. Think about what does this thing look like in five, ten years. Do you really even want to be doing this thing in five, ten years? You know, all of those things so that you have a little bit of a compass and a map to go after. Just kind of winging it, just saying like, hey, let's see what happens in a business without a plan. I'm not going to say it hasn't worked because it has worked

for some, but it's really challenging and it could be really difficult when discouraging moments in the business happen. So make sure you, number two would be, make sure you start with the end in mind and be thoughtful about that. Number three, and this is a huge, one. I can't tell you how many times I've seen this go wrong. It's gone wrong in my life. I've seen it going wrong with shows at Dear Media. I've seen it go wrong with businesses. I've literally seen things explode over this. And this is picking the wrong business partner and the wrong structure. So a common misconception is, you know, two people have a great idea. This, this happens a lot with young people or first time entrepreneurs like, hey, we have got a great

idea. Let's start this business 50-50 together. I'm at the stage of my career where I'm either in the majority and I own more than 51% or I'm in the minority and somebody else is running the business and it's their responsibility and I'm sitting along passively under 50%. Here's the thing. In a 50-50 partnership, if we set something up together and we decide that we're going left and as we're going left, the other partner says we're going right. Nobody goes right until everybody agrees to go right. If one of the partners wants to raise capital and the other doesn't, then you don't. If, you know, one of them wants to sell the business and the other doesn't, and we can't agree,

then we don't. And so I think 50-50 sounds great, equal vote in the beginning, but I would be really thoughtful about who you're making those agreements with and what that relationship is. And is it strong enough to survive 50-50 and all of that? In addition to that, you know, going back to my previous example, like picking a partner and making sure that everybody's on the same page about what the vision is, what the value is, what we're building, what we're not building, what the culture looks like, what it doesn't look like. These are all really important decisions. Additionally, as you pick a partner or a co-founder

or a group of partners, what is everybody's role sitting down ahead of time and getting very clear about that. And Lauren and I's relationship, we obviously, you know, she's not involved in the day to day of dear media and I'm not involved in the day to day of her product business. We do this show together and obviously we have multiple touch points together in the businesses. So what we decided early on is as it relates to creative and vision and branding and color and all of the stuff that she's passionate about products that she comes out with, she has final say there. As it relates to structure and finance and capital and all those things, because I have a little bit more of an expertise there, that's my world. We carved it out from the beginning. You know, as like HR related stuff typically goes with me.

Operation stuff typically with me. direction, branding, vision, all of that stuff, aesthetics of this studio, aesthetics of the office, like typically her. You know, so we both play critical parts in our partnership, but in the beginning, we carved out and said, hey, you have veto here and I have veto here, and this is what you're doing and this is what I'm doing. I think that I, you know, when I see partnerships where they don't do that in the beginning and then, you know, one person wants to be the CEO and the other person wants to be the CEO,

that could be really messy or, you know, one person wants to raise capital and the other person doesn't. So again, it's really important. I would really, really caution against doing business with close friends and family as somebody who does business with close friends and family. And here's why. It is really, really hard. And the dynamic is always forever changed because relationships are intimate at the friendship level. at the, you know, in loving relationships and intimate relationships and partnerships. And when you add in the stress of a business and the tolls that that takes on not only individuals, but relationships, it puts a different kind of pressure. Also, if you're going to be hiring friends

or working for your friends, like that creates a different strain. If you're going to bring that into the marriage, again, like Lauren and I, I think we've co-parented together. We do this show together. We've been a relationship together. The hardest thing we've ever had to figure out is, the dance that takes place as it relates to us in business. It's really challenging. And, you know, many listeners that or viewers of this show have seen me caution couples against doing business together. So, you know, really like go through all of the mechanations of what it looks like to be in a partnership with your friend or your co-founder or whatever. What's everyone doing to find the roles, you know, make sure that everybody's on the same page. Make sure we have the same

long-term vision. And if you don't, like, it's better to end that early and go your separate ways than to try to go out it together, like really figure that out. That's my advice. Just really be on the same page. Pick the right partner. Pick somebody ideally, and this is important, that complements your skills. So I'm not so creative and I don't have the greatest idea for products and I don't know these things. Lorne does that so well, but I am great with numbers and I am great logistically. So we make a great team. Figure out what you do well and maybe what your co-founder does well and figure out if those skills are complementary or if you're both kind of doing the same thing. If it's both doing the same thing, that could be problematic.

This episode is sponsored by cotton. Let's take a quick break to talk about cotton. As someone who's constantly refining my routine from what I eat to what I wear, to what I invest in, I've learned that the materials we surround ourselves with matter more than we would think. That's why I've made a conscious shift towards wearing more natural fabrics, especially cotton. It's timeless, it's versatile, and it's rooted in something real. Cotton literally comes from the earth. A flower that transforms into a soft, breathable, durable fabric. You can't beat that. Cotton is incredibly gentle on the skin. It is so hot out here this summer in Austin that you need something that breeze. It's hot everywhere, to be honest. So having something that breathes and cool and keeps you fresh and energetic

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you're choosing something that's better for your body, better for your skin, and built to last. You'll feel the difference in your skin will thank you. Cotton is the fabric of our lives. To learn more, visit The Fabric of Our Lives.com. Again, that is the fabric of our lives.com. Let's take a quick break to talk about Fatty 15. I'm so excited to share with you guys an incredible scientific breakthrough to support our long-term health and wellness. C-15 is the first essential fatty acid to be discovered in 90 years. And get this study study. have confirmed that it's three times better, broader, and safer than omega-3s. The origin story of Fatty 15 is Dr. Stephanie Van Watson, who's been on this podcast twice now,

discovered C-15 while working with the U.S. Navy to continually improve the health and welfare of aging dolphins. I highly suggest you check out the episode we did with Dr. Stephanie Van Watson. She describes this crazy story. But we don't have time for that in this read. Here's the thing. It's pretty simple. Essential nutrients keep ourselves healthy, which keep us healthy.

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I wake up in the morning, and it's one of the first supplements that I take. I did a whole episode about this. I've been taking it now for at least eight months, maybe longer now, and I feel incredible. My inflammation's down. I feel healthy. I feel energized. Fadi 15 is a science-backed award-winning, vegan-friendly, and pure C-15 supplement. The only ingredient in it is C-15. And Fadi-15 is on a mission to replenish your C-15 levels and restore your long-term health. You can get an additional 15% off their 90-day subscription starter kit by going to fatty15.com slash skinny and using code skinny at checkout. Hello, everybody. Let's take a quick break to talk about my favorite summer tequila. This

been my go-to tequila all summer long. We've been hosting a ton of events. We've sat tight in Austin this whole summer because we just had our third child. And because of that, it's been hot and we need things to cool down. So I've obviously discussed in previous spots all about my perfect margarita, which I do with the stroll's beautiful repisado. I know many people love the blanco, but I personally love their repisado for my margarita. Of course, you can use the blanco, which is also phenomenal. But today I have something even more exciting to share. There's a drink that is absolutely incredible for the summer that you can use with the Blanco estrall tequila. That is the watermelon tequila smash, which is an incredible summer drink. All you have to do

is take some watermelon chunks, some agave syrup, some estrall tequila, some ice, maybe a little bit of mint, and then you smash it all up, and it makes the most incredible cocktail. And the last time I hosted a party doing this, it was going gangbusters. People were going nuts for my watermelon smash. It was nuts. So for those of you that are unfamiliar with the straw, A straw is an incredible tequila. What I love about it, it's a premium tequila with an affordable price point that everyone can get into. And it comes in three spectacular variations. The Blanco, which I have in front of me right here, the Anaheho, which is more of a sipping tequila that I have as well.

And then the repisado, which I don't have right in front of me because I think I drank my last bottle. Please send me more a straw. And that is going to get a little bit more of like a floral taste. That's a little bit more of a spice. That's what I like to make mar and margaritas with. But you can't go wrong with any of them. Like I said, you can have this one for sipping. can even do the Blanco for sipping, or you can do the repisado for a classic margarita.

What I also love about a straw is they take their leftovers and make Adobe bricks in Halisco, Mexico, to help build homes for people that need the help. And so you can drink tequila and also feel good doing it. And like I said, it's also extremely affordable for a premium taste. So if you're out there looking for a new summer drink, a different tequila, definitely check out a straw. We have also been gifting this to family and friends. It makes an incredible gift.

It comes in these beautiful bottles, and it's a great gift to give a dinner. parties, birthday parties, any kind of party, honestly, who doesn't want a great bottle of tequila. And as I mentioned earlier, in addition to the watermelon smash, which you should definitely try, I'm sure you could just look up watermelon smash tequila recipe and then use the Blanco tequila. Definitely head over to my Instagram, Michael Bostic, and check out the tutorial I did on how to build the perfect Estrelle Michael Margarita. I did a whole video on all the steps and the exact measurements to make the perfect margarita. You cannot go wrong with that. But definitely check out the watermelon smash as well. So again, A Straw is my go-to tequila for

margaritas at home. It's an affordable, great-tasting tequila that mixes beautifully into just about any cocktail, especially a margarita. And Estrell's award-winning quality and taste has an agave-forward citrus profile that adds a burst of brightness to any cocktail. Housemark Summer is here. Time to stock up. Go to A-T-R-A-L-T-E-Q-U-I-L-A dot com to find a straw near you, and don't forget the limes. Please enjoy responsibly. And long-time listeners and viewers know, we don't just drink anything. We're very intentional when it comes to what we put in our bar, what we put in our bodies, what we give to our friends. And a straw definitely passes all of those tests. It is Dear Media's tequila of choice and the tequila of the summer.

A straw tequila. Number four, and it's been the theme of this show since, I don't know, maybe the first 10 to 15 episodes, and we've said it for close to 10 years now. When you're thinking about doing a business, stop thinking so much. Once you've got the idea down, once you've got your long-term vision, once you've got the structure, you have to launch fast. You have to get it out there and you have to adjust along the way. I've said for years, launch fast and adjust. A lot of people in the business community maybe don't agree with this advice. The world that we live in now in a 2025 world moves too fast. This is no longer Mom and Pops Corner Store where you have eight years to figure it out. Even in the restaurant space now, you see restaurants come and go.

You see bars come and go. You see fashion brands come and go. You have to be able to, when you have a good idea. You got to get it out there, throw it out there, even when you feel like you're not ready, even when it feels like you're a little bit scared, even when you feel like it's not perfect. Because here's the thing, I guarantee you it is not perfect. And you're going to get feedback and you're going to get criticism and you're going to get pushback on anything that you launch. If you go look at the early days of this show, and even to this day, constant adjustments, constant improvements. If you look at Dear Media, we've constantly evolved the business and the brand. If you look at anything that anyone's done successfully, go look at Apple, go look at Nike.

and they change. You need to get this thing out there because, one, nobody cares that somebody stole your idea. Think about how many ideas are out there that are probably the same idea. It's all about execution. I can't tell you how many times young entrepreneurs come to me for an investment and they go, hey, will you sign my NDA before I share my investment? I always say no. If your idea can be destroyed by somebody else copying your idea, it's likely because the idea is either not strong enough or you're not executing enough or you're not fast enough, right? If somebody else can hear your idea and crush you in the market, then that's a really bad business to invest in as an investor. So you have to keep that perspective. I've seen many people over the years come to me

in the podcast space, show space, particular with this idea, hey, I want to launch a show. I've got this great idea. I want to do this. What do you think? And at the time, sure, it was a great idea. Fast forward, they waited a year, two years. That same idea exists across 10 other shows and is being done better. So now that great idea they had just got basically taken over by 10 other people. So you got to get it out there, even if it's not perfect, and adjust it along the way. If you go back to the early versions of this podcast, they were fucking terrible, right? We keep them up on YouTube. It was a disaster. We're interrupting. The sound quality was bad. We had no idea about footing or format or anything. But as you see, slowly over time, it improves and proves and proves.

And now eight or 900 of these things later, we feel a little bit more confident. But we're still not perfect and we're still improving and we're still adjusting. So, you know, it's been 10 years of doing this show, hopefully for the aspiring creators or podcasters or showrunners out there, they take that as like, oh, okay, doesn't have to be perfect because we're still not perfect. But you got to get it out there. I can't tell you how many people I've seen just talk and talk and talk about what they're going to do, never doing it, and then having somebody else do the same exact thing or a version of that thing and have tremendous success. For those that are a little bit scared or nervous, just know that no matter what you launch, no matter how perfect you think it is, there's always going to be

critics, there's always going to be pushback. You need that feedback from your customer, from your audience, for your your marketplace. You need them to tell you what they like and what they don't like. And then once you get that feedback, you can continue to adjust and go along the way. So number four, taking too long, really launch fast and adjust. I've said it for close to 10 years. It's so important. If you're watching this right now and you've had that. idea and you're ready to go just go it's never going to be the right time it's never going to feel right it's never going to be perfect just go every day you waste is just another day that you're going to be behind all right next one and this is for maybe the person who has started

their company they've got their business up and running they've got that great idea they've launched fast they've adjusted they've realized now that they need to bring other people on to help them, tangent, I think it's very important to decide, do you want to build a company, which is a group of individuals moving a mission in one direction? Or do you want to be a solopreneur where you basically run a company on your own? Maybe you have a couple freelancers that help you here and there. Perfect example. You want to be a creator or an influencer. You don't really want to run a company. You want to get paid for collaborations. You want to travel when you want. You don't want the responsibility of HR or capital, all this. You just want to bring money in and

basically control your freedom and your time. That's great. great. Company, you're bringing on people, you're scaling beyond your own capabilities, you're building something bigger than just yourself, and now you're responsible for the well-being of those individuals and that company. It's an exercise people need to think about. If you do want to build a company and you do want to be an employer, this is going to be advice that I'm sure many of my fellow entrepreneurs and employers will push back on me on, but I've had this mentality since pretty much always and definitely since the entire time of Dear Media. And my theory and my theme, it goes like, I don't want to call it a theory, but the theme of

how I operate goes like this. Higher fast, fire faster, promote fastest. And here's the idea behind it. I can't tell you how much time is wasted in HR, in interviews, in back and forth, how many great team members are lost with this. ridiculous hiring process that requires 18 people to meet the person and four or five different check-ins and a long interview process, it's such a long waste of time. And what happens is you lose great candidates to other companies that are faster. And also you spend too much time going

back and forth with all these people that take you out of what you really need to be doing, which is operating and running the business. I've had job interviews and people in the company, if you talk to them would tell you, I've had interviews that have lasted two minutes. And I've had interviews that have lasted 30 minutes, rarely would it ever go there. I've had interviews where I've known within 30 seconds that I'm not going to hire somebody and I jump out in two minutes. I've also had interviews that in two minutes I know and I hire them from the gut. Getting people in the door quick once you've gone through, you know, a few of the questions,

made sure like so many employers, they don't hire from the gut. They hire from a sheet of paper. I don't know where anyone in this company went to school. I don't know what their previous capabilities are. I trust if they're applying that they have the skill set. Of course, we give them a couple tests and we have them meet a few people. But if I feel good about the person, if I feel like they're a go-getter, if I feel like they're a self-starter, if I feel like they're a self-starter,

if I feel like they have integrity and I feel like they're just kind of like the right general vibe, I'll give them a shot. But now let's follow it up with the second part. We've gotten, you know, we've got people in the door. We've not wasted a ton of time back and forth with all these hiring, losing employees, wasting your own time. We've got people in the door. Now there's the second part, which is very important.

which is remember first part higher fast second part fire faster you got to give everybody a chance but if you find out early on that they're either the wrong hire they can't do the job they're the wrong cultural fit they have a bad attitude they can't you know they're not a team player any of these things so many of my fellow employers wait too long and go through all these process to get you've got you got to get rid of people quick one you're wasting their time so from an empathetic standpoint you don't want to carry somebody along that you know does not have a future in your business you want to you know get them out the door and let them go figure out a better fit i think everybody has an opportunity to go have a great career somewhere but it might not be in your company or at this

company you've got to figure out who's right and who's not right for the company again this is these are relationships and these are daily interactions some of the most important interactions you're going to have and so if they're the wrong fit keep it tight fast get them out the door quick give them the opportunity to go get employed somewhere else give them the reasons don't waste their time. Don't drag this out for a long process where you're just stringing somebody along when you know they're not right. Listen to your gut and get them out as quick as possible if you know that you just made the wrong hire. You made the wrong choice. Super important. And then now we get to the most important part. I'm not just a cold-hearted bastard that throws people out of the

company. Actually, we rarely do that. The most important part is promote fastest. I see so many companies and they have these structures or these hierarchies where like, you know, somebody's kicking ass in the business and individuals just really delivering. You've made a phenomenal hire. Maybe that, you know, they start to really excel and people just, they lag and they lag and they don't acknowledge that person. If you hire somebody and they're kicking ass and they deserve more and they can handle more, promote them.

Get them, get them more incentivized. Get them into the business. Give them greater roles. Ask them, like, if they can handle it, ask them what else they want to do. promote these people the fastest and hold on to them as tight as you can because these are the people that are going to help scale beyond what you can do individually. So many people lose great people because they're scared to give them that promotion, scared to acknowledge them, scared to move them up quick even if they deserve it because of some preconceived notion. At Dear Media, we have a lot of

people that have really moved up very quick. We have a lot of young people that have taken on more responsibility than they would at other companies. I think acknowledging people that are really out there and going after it is important and not being set into some kind of bias or corporate structure or some kind of idea that you read in a business book. Really like, I think the silver lining here, like kind of like reading between the lines of what I'm saying is a lot of this is from the gut, right? You trust your gut when it's hiring, trust your gut when you fire out. And then if you see someone that's kicking ass, don't lose them because you're scared to promote them or acknowledge them faster. It's so important. So again, number five, hire fast, fire faster,

promote fastest. That's my motto. That's what we've done over here. That's how we have, I've personally had success. It's maybe not what you'd read in typical business books. I'm sure there's all sorts of books on how to hire people and the process and da-da-da-da. But I can honestly say, I don't think that I've ever spent more than 20 or 30 minutes interviewing an individual before hiring them. And we've had people that have been here now for seven, eight years. So something's going right. Here's what's next. And this is maybe boring to some. It's an area that, many business owners and entrepreneurs don't like, but it's a hard truth that we all have to face and that is ignoring the cash flow and financials of the business and pulling money out of the

business way too early. So let's talk about it. You've been working for somebody else for a long time. Now you've set off on your own and you're starting your own business and you're putting all your blood, sweat and tears into this new business and new brand and you're thinking to yourself, wait a minute, I was making more take home money at my job than I am in the company that I own. But look, here's a bunch of money coming in and sitting in the bank account. Maybe I should put myself on salary. Maybe I should pull some more out. In the early days of a business, I would highly, highly encourage anyone to take as little out of that company as possible. When I started Dear Media, I did not take a salary, not a single dollar for maybe

two years. I did not take a dividend for two years. We left every single dollar we could. Lauren and I had a podcast. We were monetizing off that. I had previous businesses. I was running another company and working another job and using that to survive. But as it relates to this company, for years, I didn't take a salary, didn't take any money out. And the benefit of that is all of that money was able to stay in the company to hire great people, to scale, to weather hard times when we, you know, ran into the situation where we decided to actually go out and raise capital. I owned so much of the business because I had never deluded myself and never taking stuff out. And I was in a strong position because I held on. On the reverse of that,

I've seen many situations, and I've done this in years prior to other businesses, where money starts to come in and you pull out every dollar and you increase your lifestyle and you start to use that money to live. And what happens is you're stripping the the oxygen, the cash in a business is the oxygen of the business. It's the lifeblood. If a business doesn't have cash and cash flow, it dies. That's just, you know, basic economics, basic business running. So, you know, when you pull all that cash out in the early days and you're trying to get over these hurdles and you're trying to hire the right person and you're trying to, you know, pay those legal bills or those trademark things or, you know, buy inventory and the cash is out of the

business, you start to die and you get really discouraged and you start to really stress. So in order to not do that, can you take on a side hustle? Can you work a second? second job before you start the business. Do you have savings to weather those storms? You know, what are you going to do? Or, you know, if you don't have those, like, how can you live in the cheapest way possible and cut your expenses? I see a lot of people that leave comfortable jobs to start their own thing really struggle with this because they have to decrease the way their lifestyle is. And this is just a fact, like if that's the situation you're in, again, going back to point one, do you really want to be an entrepreneur? It's really important to think about because

again, if you run out of cash, your business will die. If you run out of cash and you go to raise capital from someone else, you're going to get squeezed on worse terms. If you don't have good cash flow and you want to make hires, you can't because you can't afford great talent, which means you're going to constantly be on yourself. And this is where burnout happens, right? You have no money. You're doing every task. You're sweating and you haven't set yourself up to be capitalized, right? So there's that. Number two, and a lot of entrepreneurs don't don't like to do this. Maybe, again, you're somebody who's worked with your hands or you're been a salesperson or you've been in production, whatever it may be. And now you have to manage

that P&L. A lot of people do the kind of thing they do in personal finance where they don't look at the P&L. They don't check it every day. They get a report from a bookkeeper once a month. They mistake their cash flow for, you know, the business doing well. They don't actually look at their profit and loss. And before you know it, you are out of money, you don't have a business. you have to be good at looking at your numbers. If you're not good at it, you've got to find somebody who will help you do it. I would say, honestly, in the beginning of a business, look at it every single day, how much money is coming in, how much money is going out, what are you paying in bills, what are you paying in payroll, figure all this out, not paying attention to it and just kind of closing your eyes and hoping it takes care of itself is a sure way for a business to go under. So if you're in that situation now, get your arms around your finances.

If you're thinking about starting a business, make sure you're setting up the right structure, get your right account. count it in place, get a bookkeeper. I had some great advice early on in my career. I must have been 21 or 22 and I was talking to a very accomplished entrepreneur and I was sharing with him this idea of a business that I was starting, which was an agency at the time. And he said, set your business up as if it's already a multimillion dollar business. Bring in a great bookkeeper, get a great software for accounting, get, you know, a great, you know, fractional CFO that can look at your stuff here and there, get a great advisor so that once it does become that thing, you don't have all this cleanup and it's organized. And I think that advice has served me

because, again, finance is an area that every entrepreneur or business leader has to be aware of, whether it's your expertise or not. You have to pay attention to your money. If you're not paying attention to it, somebody else will be. And a lot of bad things can happen. And so spend that extra dollar, spend that extra time to figure out how to set up your finances in the way where you can be responsible with them. And then, again, leave as much of that money in the company for as long as possible until you really need to start taking some out because there's going to be a rainy day where you need it and you need it to hire and survive and all those things. I am a big fan of the row. It's just such a beautiful brand. I think it's understated. It's chic.

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with no credit card required at www. YNAB.com slash skinny. Again, that's YNAB.com slash skinny. All right, Dallas, it's happening on Saturday, October 11th. Dear Media IRL is coming your way and we could not be more excited to bring the energy. The real conversations and some of your favorite Dear Media hosts, straight to you, live and in person, including yours truly. We've got an incredible lineup of speakers, panels, and moments you're not going to want to miss. This live experience will bring some of the most impactful voices in media, business, and content creation, real conversations, unfiltered insights, and a chance to connect directly with the Dear Media community.

Whether you're a listener or a creator, a founder, or just someone who's interested in building something, on your own. This room is where you want to be. The energy, the people, the ideas. It's completely different when you're there live. Tickets are officially live and available, and they will go fast. All you have to do is head to Deeremedia.com to grab your tickets. Again, that's Deermedia.com. We will see you live in Dallas. I see this happen a lot with new entrepreneurs. Seizened entrepreneurs, not so much because you know, as you continue to scale, it is impossible to do everything. And it is also impossible to be the best at everything. So you have to start thinking about bringing on people that are better than you. And this is threatening to a lot of

entrepreneurs, especially ones that are a bit more control freaky or more control freaks, because one, it's a hard pill to swallow sometimes to admit to yourself, hey, I'm not the best at this and there's somebody better. And two, it's sometimes, you know, some people feel threatened bringing in people that are more skilled or more experience into their business. I know what I'm good at in my world and I know what I'm bad at. The stuff that I'm bad at, I want to go and bring the best people that I can find that are within budget into the business so that they can just do their thing. I want to give them autonomy and a little bit of direction, but I want to let them like own their area and thrive. For me, for the longest time

at Dear Media, I was doing all of the new show signings, all of the talent signings. That's not my world. I'm not the best at it. I was never like in the talent space. There's people, shout out Paige McKenzie that are much better than me, that love to do that, that live and breathe that have better relationships with agencies and management companies and have better bedside manner. I have very little patience for a lot of those negotiations. And so they run that area. There's people that are much better, you know, early days of this podcast. I used to do all of the editing and all of the production myself. I'm not an editor or producer. I did not go to school for this. I brought on people like Carson sitting there and others who are much better and

know their shit and are better like the technical stuff and have better ideas and know how to set up better structures and they can do that from a sales perspective i felt really strong at sales but as i start to do other things in the business and i can't dedicate 100% of my attention to sales because there's other things i got to focus on and some of the earlier points you have to bring people on that are not only great sellers but better sellers than than you or me to be able to scale those areas of the business so you know making sure that you empower people that you bring on people that are not only as good as you, but better than you in many areas is so important. Sometimes I see new entrepreneurs. They bring on people that are maybe weaker than them

or not as strong as them in certain areas because they feel a little bit of a threat or they feel like, you know, it's going to make them not look as great with the other employees or other team members. For me, it's the exact opposite. How do I get the best people around me who are more skilled than me, who can do better, who can scale? These people are going to bring new ideas. They're going to bring fresh ideas. And you have to be willing to let them go and let them own their lanes and their areas of the business and thrive. So a mistake I see people making is not doing that and hiring people that they know that maybe are not as good as they could be, maybe because it's a threat to them personally

or they're just scared to get better people around the table, but get the best person you can afford in an area that you're not the best out for sure, and make sure you make that a priority. Last one, but I think actually maybe the most important one, especially if you're somebody setting up a company is making sure that culture is number one. And you know these people that's like, oh, we're all culture. We're all family here. We're all, you know, they set up the fucking yoga studio in their company and like they all earn these company offsets. No, no, no. First, you have to recognize most people that are coming to work with you for you in your business are there because it's a

career for them. They have their own family. They have their own friends. They're doing their own thing. It's not to say that they don't love you and admire you and want to work with you. But let's not mistake the company as the family. They have their own family and that's likely why they're working in the first place to support themselves and their families. So that perspective, all that being said, you can create an incredible environment that is built on trust and respect and a foundation of empowerment and, dare I say, fun at times. And that is very important. And it should be above everything else. It should be, you know, when you're reviewing everything at the end of the, every of the month, talking about the culture and how everything's going

should be above the sales and the P&L and what's being produced and what's being sold and all that. And here's why. If you build a phenomenal culture, you are going to attract great talent. If you attract great talent to my point earlier, you're going to be able to build a phenomenal company that scales beyond just you because you're going to have people that want to work in the business that feel empowered. If you build a great culture and people are happy and empowered working in your culture. You will spend much less time micromanaging people

and holding people to account in HR conversations or performance reviews because people are actually happy in the environment they work in and they want to bring their best. I do very little correcting in this business like if I'm being honest.

And I think it's because we've spent a lot of time making sure the right people are in the right seats and they're empowered in the right way with the right respect. I think if you do that first and you create that kind of of culture, you're going to get the best out of people because they're happy to be there and

they're inspiring or they're inspired to be there and they feel empowered to be there. Second part of that is if you have somebody who is a super high performer, maybe they're one of your best salespeople or one of your best producers or whatever it may be, but they're toxic for the culture and people can't stand them and they're constantly dragging people down, you've got to cut those people out. It's very easy for individuals like that to really a culture. I see a lot of employers getting scared to remove those kind of people because they think, oh, well, what if I get rid of my best salesperson? What's kind of a sales? Likely what will happen is the other sellers will rise to the occasion. You don't realize the damage that a toxic

person does to a culture if you don't figure it out. Also, the people you work with will respect you more for removing people like that. So if you're an entrepreneur or business owner and you're listening and you're thinking of somebody in your company that is that toxic person, I would highly encourage you to get rid of them and watch your culture rise, watch the respect and admiration of the people around you, move up in conjunction. It's so important. The last thing I would say as it relates to culture is if you create this kind of culture, you are also going to have the opportunity to have people external of the business recognize you as a great culture and want to be in partnership with you or work with you. I can't tell you how many times

we get great inbound from people that either want to partner with us or join us or, you know, spots from us or inventory from us because they've heard good things about the culture of the business. The last thing I will say about culture is this is all rooted in personal accountability. So my personal perspective as a business owner, as an entrepreneur, as the CEO that sits on top of the organization is that everything in the business is my fault. While at the same time, all of the credibility is on behalf of the team. And I truly mean that I don't just say that. So what I think that I do at this stage of the business is I have an idea and I have a direction and I have a vision, but I'm doing very little of the legwork to get there.

It's all the team doing that after maybe setting that idea and that direction. I will take credit for starting the initial idea and creating the momentum to do that. But now that we've built this company, really, it's like I should, my job is can I have one to two good ideas a month and can I make sure the culture is enforced and can I make sure that we're all moving in the same direction? while at the same time also believing that everything that goes wrong is my fault. So I'll give you a dumb example. If somebody misses an episode, maybe one of the junior team members, they just started at Dear Media,

they work on the production team, and they forget to get an episode, Carson would never, they forget to get an episode out for one of the shows in the company. Normally, what a lot of people do is they pass blame on that individual employee or that manager or that department, and they all attack. My perspective is, first, this is my fault because I go into the space of, did I not set the right structure up properly? Did I not hire the right management structure? Did I not vocalize and articulate how this is done?

Did we not create the right procedures? I start from that perspective, because if you start from that perspective, immediately then, you can start working through how the problem happened. what this also does as a bonus, where is if the people at the top start to take ownership, then what happens beneath me is maybe the executive in charge of production start to say, you know what, Michael, actually this one's on me, I forgot to do this, and then what happens is maybe the manager says that. And then everyone starts to take accountability and you create an entity in a culture

where people want to ban together to help to solve the problem as opposed to pointing the blame game. Nothing drives me more nuts than when I go to dinner or meet with a different, you know, maybe a CEO or an executive and they're blaming all of the people that work for them for their problems or their company's issues. Everything starts from the top down. So, you know, what I see happening in the reverse is things are going well. CEO and executive takes all the credit, gives none of the credit to their team. Things going bad, they pass all the blame down. This is a really wrong way to run a business. You're going to create an atmosphere where your team members are discouraged.

Nobody's taking accountability. And honestly, nobody wants to be in the culture. So I would reverse that and watch what happens. You'll get more respect. You'll get more admiration. You'll get people that want to band together and help and create a great business. And you'll create a culture where people feel like if they make a mistake that the company has their back and that we can fix it. You'll create something where people aren't hiding mistakes and trying to get around

because people will know that the team is there to make sure that we pick up the slack and band together and help whatever issue needs to be helped. All right. those are my business pitfalls and mistakes to avoid i've made almost all of these mistakes in multiple businesses over the years i've made these mistakes in dear media i'm hoping that this will help you avoid them or if you are making them currently help correct them there are about a hundred other mistakes that i could go through there's so many things that happen in business it is the hardest sport in the world it is the highest stakes it is the most stress but it is also the

most rewarding. So anything that we can do to make it a little easier we're trying to do here. And I hope this episode was helpful. With that, see you next time. Be back for another great episode.