Navigating Freelance, Tech, and Fatherhood with Damon Brown

Explore the world of freelancing, technology, and fatherhood with Damon Brown in the latest episode of The Talk Freelance To Me Podcast. A champion for side hustlers, solopreneurs, and non-traditional creatives, Damon has a knack for helping creative minds flourish.

As an influential voice in the entrepreneurial space, Damon regularly shares his wisdom through his Inc.com column, public speaking engagements, including platforms like TED, and his consulting services. He's also the author of several books, with his latest being The Complete #BringYourWorth Collection that’s coming October 20th! This full volume includes the original Bite-Sized Entrepreneur series, the critically-acclaimed Bring Your Worth book, and the groundbreaking Build From Now book.

You don’t want to miss this episode!

About Our Guest
Damon Brown (damonbrown.net) helps side hustlers, solopreneurs, and other non-traditional creatives bloom. A best-selling author, 4-time TED Speaker, and a long-time freelance writer for Playboy, New York Post, and others, Damon co-founded the popular platonic connection app Cuddlr and led it to acquisition within a year, all while being the primary caretaker of his infant first son.

He now guides others through his private consulting/coaching business, free weekly newsletter at www.JoinDamon.me and popular #BringYourWorth show every Wednesday and Sunday at:  BringYourWorth.tv

His new book, The Complete Bring Your Worth Collection, will be available on October 20th. Take his free creative resource quiz at: www.buildfromnowquiz.com

Noteworthy Quote from this Episode
“You have to define what your metrics of success are. If I used somebody else's metrics or the metrics of my old life, then I wouldn't have made it this far. I would have gotten frustrated. Ambitious people with kids have to stretch their timelines.”

Connect with Damon
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Transcript

Unknown: 0:00

All right.

Ashley Mejia: 0:08

Welcome everyone to another episode of the talk freelance me podcast. I'm your host, Ashley Cisneros. mahiya and I am so excited everyone. Today we have our first ever man on the podcast. And it's the wonderful I can't wait for you guys to me. And this is Damon Brown, everyone. Welcome, Damon, thank you so much for being here.

Damon Brown: 0:31

I'm glad to break new ground. I didn't No.

Ashley Mejia: 0:35

Big deal. There's a lot of we love our Mama's and our sisters. And we've got you know, lots of girls on this show. So this is very, very special to have you here, freelance fan, just to let you know, I recently had the opportunity to attend the ASj virtual conference. It's the American Society of journalists and authors, great organization. And Damon actually served on the leadership board for years and years. I want to say right, amen.

Damon Brown: 1:00

Yeah, for about an hour was about six years, something like that.

Ashley Mejia: 1:03

That's fantastic. I'm new to the group, but I had the honor of hearing your keynote presentation. And it was so amazing. And so I just I asked if you could be on the show. And so thank you so much for carving out some time from your very busy schedule to be here with us today.

Damon Brown: 1:20

Absolutely. Thanks for having me. Ashley. I'm happy to support as we talked about off camera like I liked the work that you're doing and you know and the conversation that you're trying to start Yeah,

Ashley Mejia: 1:29

thank you so much and so freelance fam and I'm gonna read you a little bit from Damien's bio, he's done a lot. So this is a brief summary so you can kind of get acquainted with his experience. Former as Jay board member Damon brown helps side hustlers, solopreneurs and other non traditional creatives bloom, a best selling author for time TED speaker, and a longtime freelance writer for Playboy, New York Post and others. Daymond also co founded the popular platonic connection app Kudler, and let it to acquisition within one year, all while being the primary caretaker of his infant first son. He now guides others through his private consulting and coaching business has free weekly e newsletters at join damon.me and a very popular hashtag bring your worth show every Wednesday and sunday@youtube.com. Forward slash brown Damon, he has a new book coming out called the complete bring your worth collection, it's going to be available October 20. And you can take his free creative resource quiz at building from now quiz.com. Damon, thank you, thank you, thank you for being here. This bio is like hashtag goals like the kids say so.

Damon Brown: 2:49

Like the young insane, like the eigenes, as we can say now,

Ashley Mejia: 2:52

right? You've done so amazing, like these things are so diverse from the app and getting it acquired your Silicon Valley time, your time as a journalist like, can you just tell us some more about your journey going from a journalist to this serial entrepreneur that you are now?

Damon Brown: 3:09

Right, thank you. Thank you, Ashley, I appreciate the very flattering bio. So my main thing when I was much, much younger, younger than my wife, and I's youngest son, I have a almost 10 year old and a recent seven year old, both boys. And so when I was younger, then my wife and I's youngest son, then I was really into telling stories. And I was really into technology. And my mom says I was really into both when I was around three. So this is very much an innate, this was what I was drawn to. I was born in the 70s. And so I was lucky enough to be born at a time when technology was blooming. Instead of birth VCRs came out on its right if you think about the 70s was kind of the enemy of time with the technologies and the foundation is stuff that we do today. And so there was always a conflict. As I went through school I did find in school, and I've gone to grad school and other things like academically I did fine. But there was always this conflict between me hanging out with the people who are quoting Shakespeare, and me hanging out with the folks who are trying to reprogram the microwave. Like there was always this conflict between the bookworms and the nerds, you know, which identify with both the terms that we've abrade embraced over the years. And it wasn't until probably late College, where suddenly we realize that communication was going to be impacted by technology. And then all of a sudden, the stuff that I've been studying started to make sense. And so that made it a lot easier for me to take a leadership role with ASj to kind of see where things were going ahead of time. Just because I've been studying those things as far as technology communication, merging the whole time. My main thing as my career has progressed so we can get deeper into this however you like it seeing how intimacy and connecting with each other is impacted and actually can be driven by technology. And so with a second app that I founded, called Kudler, it was myself and two other co founders. The main thing was to connect people for hugs. And at that period of time, it was 2014. And my wife and I's first son was about to turn one. And at that period of time, the big concern was, Facebook was the biggest company on the planet. So go back about 10 years ago, before they turned Mehta, and all these other things were happening in people. It was just this discussion, I was just starting about how technology might not be connecting us the way that it should. And there's a level of superficiality with that, even with the so called hookup apps like Grindr, and Tinder. And some of you single folks might know what I'm talking about. Aaron, right. That was the vibe. And my co founders, and I realized that there was a gap, there were people who wanted to have that human connection, but didn't necessarily have access to it. And we ended up having we launched it bootstrapped it, which meant we funded ourselves, we had a quarter million users at our peak. And then we have getting acquired shortly after our son's second birthday. So it was about how they end up, we end up selling about 11 months after we started. And what we realized was that, and the hypothesis, particularly from my end was that technology can actually be used to connect with people. And there's one message in particular, because I was a CEO, essentially. So I was handling the day to day, while one of my colleagues was actually the CEO, and the face of the company. And so I handled all the email, you got a quarter million users, you get a lot of email, every single DMS message, you name it, it was it was crazy. And I remember one message being from sound like an older gentleman, I want to say he was in his 80s. And his wife passed away a number of years before. And since then he hadn't had any physical connection, and our fax and our app allowed him to connect with someone else. And I was like, okay, that's why we're doing this. That's what got me up in the morning. And so, again, using that technology, to actually connect people, rather than to separate people. And I think that ties into our work as communicators, where we can use, I've talked about this during the keynote, we can use AI to outsource our work, for lack of a better term, and lean on that a lot more. And that might get us some quick money, but it's not going to have the thumbprint, the patina, the energy, the soul, of what we have as creators, just like if we were to use a chat bot a few years ago, or just lean on automated social media 10 years ago, or just start doing blogs without just because we want to get a book deal 20 years ago, like I've been in the game long enough, and perhaps you have to where you started to see these cycles. Today, a lot of these cycles are based on technology. And my work as a business coach, as a keynote, the different things that I do, even if it's doing another startup, the intention is to say, technology is a tool. And if you feel like you have to give up your soul, or that you're going to be out of a job, because of this technology that you might be using the technology wrong. Maybe there's another way we can use this technology to connect people, maybe we use this technology to communicate more, maybe we use this technology to pour more humanity into the world. And as we talked about offline, like with the pandemic, and we're going into the fourth year of this, a lot of the work that I do, and other people do, and including some my mentors who I adore, that's starting to come into the spotlight because people are realizing that technology without humanity, that doesn't mean anything. And things can change that quick. And suddenly all the technology in the world isn't going to help you. What's going to help is a connection to other people. So that's my very long way of saying that's my that's my intention. And for me, it's not me doing a whole bunch of things. It's just that one core idea. And then that message, or that creating happening across different mediums. That's where we look at the career. I love it.

Ashley Mejia: 9:15

I think that idea of connection, because that's what we do. That's what stories do. Right? They help us connect to idea to lessons to morals, to other people give us information. And with color, you know, you're really helping people connect in a physical way. I think that's beautiful. And that's that's part of who we are as humans. That's what separates us from the robots is that we're social creatures. We can't live by ourselves like you know, all the scientists have showed that that babies have to be cuddled have to be touched that sense.

Damon Brown: 9:49

Oh, the baby studies break my heart. Yeah, it's

Ashley Mejia: 9:51

so interesting. Even you know, we talked off camera about our kids and you know, having children and I remember even you know when I was pregnant for the first time learning about you know, the skin to skin contact when you first have a baby. And you know, I didn't know any of these things, I'm learning it new. And even just talking to like my grandmother, like her experience, having a baby was way different for a variety of reasons. But one of those things that skin to skin contact, that wasn't a thing when she was giving birth in the 60s, you know, and for me, it was like you have your baby, and then you immediately it's for bonding. And so I think you tapping into the ability to connect people, both with your storytelling, your ability to connect people with color, you definitely like people might see your career and just be like, Wow, there it is so diverse. And it is, but there is that through line that you can see that connection that using technology as a way to connect. I love it you

Damon Brown: 10:47

for those of you who are trying to figure it out. That took me a long time to see that through line. And as people much wiser than myself, like I'm thinking of like Jonathan fields, and I'm thinking of Jenny Blake and Dorie Clark, a lot of fellow coaches who have been in the game longer than me who I who I have a lot of respect for. All of them say that she should be driven by curiosity. You know, we also understand that from the journalists standpoint, right? It's like, all the stories going to be on the cover of The New Yorker, whatever. It's like, no, that's not actually how you find that stories. What you do is you get curious and ask certain questions. Even if he was asking yourself questions about the subject. And you're like, there might be something deeper here. Let me pull on that thread. And then we start to pull on that thread and suddenly start to see things coming together. For three best selling books. Out of the 26 that I've done, the three that became bestsellers, I didn't know they're gonna be bestsellers before I wrote them. You know what I mean, with doing toddler and before that I did a app called so called audible, which capture people's quotes. So quotable did okay. And I learned a lot. The second one blew up, and we're on the cover of The Wall Street Journal. But I because I did the first one on my own. I was curious about the first one. And then when I joined my partners, I was curious about the second one was the same process, I have books that have sold literally a dozen copies, I got some stinkers. And then I have other ones that have sold 1000s. Same process. And so that's what I would encourage, if you're particularly if you're a freelancer, we're curious about so many different things, and a lot of us are what they call multi high finance, are interested in, right, we're interested in one thing, and then we're just sending this other thing and this other thing, and when people ask us at a cocktail party, what we do, then we get confused, that was made for us, right? That was me for several years, if not decades, I've written about this in the bytes as an entrepreneur, where I wasn't really sure. And then suddenly, the three lines started to come through. And that's why I can be so concise about it now, but a little bit into my career. So now I see it. But as Steve Jobs says, your job is to follow the dots. And then you won't be able to connect them until after you've done some of the work. And suddenly you start to see the connection. So I would encourage people, if you are trying to figure out multiple things, don't try to box yourself in quite yet. Because there's gonna be a natural pattern that's going to start to show up. That's so good.

Ashley Mejia: 13:11

That's so good. Because a lot of times I think, you know, entrepreneurs, storytellers, all of us, whenever we're creating something out of nothing, something that doesn't exist yet. A lot of times, I think that we can get a little paralyzed in the thinking part, and we put off the doing, but what I'm hearing from you is by you doing over and over 26 books, I mean, you have this, you have the recipe you've done. And then afterward, you see, wow, that was a best seller. But that process, you don't get that clarity until the end, you don't get that clarity until you start. And I think that's true with anything with a business with serving customers. I mean, you've got to, you've got to put one foot, you got to put something out there in order to get to figure it out.

Damon Brown: 13:55

There's a wonderful quote from Chase Jarvis, he's the founder of Creative Live. And I think he sold the company has moved on, because his book called Creative calling that talks about that. And my favorite quote from the book, as he says, You can't steer a parked car. So in other words, if you want to refine what you're doing, get your stuff together. I've done 300 Plus episodes of the bring your worst show. And I'm just now getting to the point where, like, my visuals are starting to look right. And I'm like, Okay, now I know what I'm doing wrong. Now, this is how I can improve them. And I look at my first batch of episodes, I start cringing, but that's the way it's supposed to be. Yes. Because I could be sitting here, you know, you could see my office. I could be sitting here in this little office planning everything for the past two, two and a half years because it started two years ago. I could see here for two and a half years trying to plan the perfect episode, and then record it so wouldn't have learned unless I did the 300 that's the process and not being afraid to move and not being afraid to have something fall apart a little bit and then learn from it fallen apart. And that's been priceless for me personally. Yeah. So good.

Ashley Mejia: 15:05

Thank you so much, Damon. So you've done like we've said so much. And you've also this whole time that you've been creating and innovating and doing these businesses, these apps. You've also been writing the whole time. You've been a longtime freelance writer for a big publications, well known household name publications like Playboy and the New York Post and your column in Ink Magazine, which, as a business journalist, I love that. I'm like fangirling over about ink. Oh,

Damon Brown: 15:36

thank you. Yeah. So

Ashley Mejia: 15:37

can you give us there's a lot of writers who listen to this a lot of freelance writers. is there advice? Is there secrets that you can share for people who want to pitch to these high profile publications?

Damon Brown: 15:48

I'd say the first step is to make sure that your network is good. I started writing for Playboy and I talked about this in one of my keynotes if you go to bring your worth that TV, I talked about this in one of the keynotes where Anna connecting with Playboy, because I was at a alumni meeting for Northwestern. That's where I got my masters. And it was someone in the buffet line. I swear, there's so one in the buffet line. Everybody had their tags, and attack said that they were editor with Playboy. And so I talked to them, you know, while they're passing the carrot. I remember like yesterday, actually, I don't brush it off, actually blushing at this. I'm like the audacity.

Unknown: 16:33

But that was the moment that was the moment it was your opportunity. Yeah,

Damon Brown: 16:36

otherwise, I might not be talking to you right now, like so. That was many years ago. And so that was opportunity with that with Ink Magazine, it was actually through ASEA. And it was ASEA colleague, who was doing stuff with NK. And they found out that I just sold my company. And they're like, Hey, we're actually looking for columnists, you might have interesting POV since she just soldiered startup. So then the two kind of pieces with that is number one, having your network, right. It could be your alumni network, it could be organization like SGA, I regularly go to the TED conference. So it could be something like that we actually pay to be in this environment. And so when you're working through that, you naturally get opportunities with people see the work that you're doing, going to be like, oh, yeah, Ashley is doing some amazing stuff over there with their podcast, maybe we could have her do this column, you know, that kind of thing. I think the second part of that dynamic is actually always be creating something. And so if you're already are doing a podcast, then you're more likely to get the attention of these organizations. The best dynamics I've found, is that when people or organizations see you doing the work that you claim that you want to do, and they're like, Okay, you're representing what you're doing. A friend of mine, Nilufer merchant, she has a book called The Power of meanness. And she has one of my favorite terms, it's called signaling. So for instance, the way that I'm dressed right here, I'm signaling a certain thing so that people identify with that, with me having a nice blazer and one of my homemade T shirts, you know, it's available from David brown.net, that represents something where it's like, I'm wearing the gear that I made myself, but also have a nice suit up, you know, blazer on top of it. And it's like, that signals a certain thing to the community or certain people that that I connect with, if you're giving up those particular signals, then that means that tribe or that group that wants to rock with you will recognize you, and be part of that wave for that cultural change that you're trying to make. You might use different language than I would I'm really big on cultural change, but but whatever impact you're trying to make, if you're not signaling the right thing, like if I was wearing like a rock t shirt, and it had a couple of holes in it, which I love rock and roll, I got musicians right behind me on my wall. But that wouldn't be the signal of the people that I'm trying to connect with, nor the people I'm trying to lead. So this represents me. And the bigger idea, if you're able to create articles, podcasts, and our case of journalists, any type of medium that represents the direction you want to go in, then you'll be able to get the attention and discussion of the different people and organizations that you want to work with.

Ashley Mejia: 19:31

That makes so much sense. I love it. I think that there's a quote that talks about, you know, dress for the job that you want, not the job that you have. And that makes so much sense. I appreciate that. And so in addition to all this journalism work, you've also written 26 books did you say

Damon Brown: 19:46

yeah, that's 27th is coming out in October. Yeah. I love books. Amazing.

Ashley Mejia: 19:51

I've left that. So what's your secret? There's so many people who say I have a book in me I want to write one and they can't. They're having trouble with the first one and you You've done this 27 times. So do you have any secrets to sticking to this process, completing the manuscript and actually publishing these books, and how you've been able to be so consistent with it time after time,

Damon Brown: 20:13

thank you for the compliments. It's not as smooth as it looks. So let's put that out there. I think there's a few different secrets. The first one is to start writing your book before you actually do the book. And so my first major met bestseller was the by says entrepreneur. And that was, shortly after I sold the startup. And it's available in the compilation coming out to complete bring your worth collection, it was 21 chapters, about a third of those chapters were based or modified on my ink column that I've been doing. So if you kind of want to work backwards, which I believe it was Tom Peters, Stephen Covey, Stephen Covey, talks about begin with the end in mind. And so if you work backwards, from there, I got an opportunity while I sold my startup that got me on the radar of colleagues who are working with Ink Magazine, they said, you want to do a column, I said, Sure, I did about a column or two a week, for about a year. And then all of a sudden, those columns start to form into a bigger narrative. And that bigger narrative became the basis entrepreneur. And there was quite a process to get that published, it's actually published under my own imprint, because the publishers in New York didn't see the vision of what I was trying to do. So then then, and I'm starting me self publishing. And then I became a best seller. And then because I was self publishing, that I have the opportunity to publish as much as I want to. So there are all these little curiosities will come that always sort of curiosities that led up to that. So it wasn't a matter of me say, Hey, I'm going to publish a book, it was a matter of me saying, I just sold my startup, something that took up a lot of my time is now gone. And I want to do more freelancing. And I also want to share some of the insights of God, because I don't know, I didn't know anyone else who sold their startup, actually, maybe to other people. So it's like, who I know really well, or I could talk to him about it. Other than that, it was me. And being a 30, something black male, who's taking the lead at home, you know, raised and then became two kids. Shortly after that wildlife had a traditional job. It was like, there was no blueprint for me. So I'm like, Well, how can I? There's stories I have to tell, how am I gonna tell people these stories are this opportunity with Ink Magazine? Oh, okay. Well, maybe now I can tell other people's stories, but I can help unpack all this intensity, because from beginning of the second startup to selling it was less than a year. So is this work? Yeah, it was a whirlwind. Yeah, we started right before around the time of our son's first birthday. I'm sorry, we started at two months after my son's first birthday. And we sold it right after his second birthday. So it was about a 10 month period. That was it. Wow, that's fast. Yeah, whirlwind. So then I'm actually unpacking some of it for myself. And the book gave me an opportunity to do that. So I think the first thing is to figure out what you're actually curious about, start building to that now, not to wait and say, oh, I want to have a book. Do I want to have agents like No, start writing that now. Because my first major best seller was based on columns that I wrote Frank magazine, well, before I was thinking about writing another book. And so I'd say number one, start start writing towards that particular process. And I'd say number two, which ties into number one, already start serving the people that you want that book later to be for. And so that my idea of the natural entrepreneur that started in 2016, with the baicells, entrepreneur, and so through my column went and joined Daymond got me to the show at bring your worth that TV, I've been just serving the same community. If you're plugged into that particular community back to Nilufer, merchants idea of signaling, if you're plugged into the community that you want to serve, and you're signaling to them, Hey, I'm here to serve you. Not only do you have a built in audience for whatever you create, which financially and otherwise is fantastic, which has allowed me to literally function and have the career that I have. But then the second part of that is that your audience, if you're plugged into them will actually tell you what they want next. And so after the bytes, such an hour turn to a series. And then I am doing a left field book called Bring your work, which is really that me working as a coach and helping out creators, freelancers, entrepreneurs, I realized that a lot of challenges they had as far as how much they charged for their work, how much they were able to make an impact on the world. There was a root issue with them not feeling like their voice mattered. And it's about 2018 2019. So that's become a big part of this session now, which makes my heart feel big. Four or five years ago, we weren't really discussing. We're discussing how much we got paid as creators. But as a coach, I realized there was a deeper problem, a root problem, where it's like, how you gonna get $3 a word from the Smithsonian, when you don't really think your words are worth 30 cents? How are we going to navigate that gap. And then being connected with our community, I realized, bring your worth was the next book that we needed to have. And the book came out and it bombed. But then three, four years later, suddenly, it's picking up steam. And it's become one of my better books. And obviously, it's the name of my imprint now and the TV show. And I have people contacting me now saying, I found this old book that you had from 2019. And I just grabbed it. And this is what I need to hear right now. And it made me emotional, because I'm all like, yeah, like, I put my foot as we say, in my culture, I put my foot in that book, like I really put my energy into that book. But it wasn't the time

Unknown: 25:52

for it. They weren't ready yet. Yeah, but

Damon Brown: 25:55

because I was connected to the community, I had a feeling that's what they would need next. So I think that would be the second part is staying connected to those communities that you want to serve. And then being about two or three steps ahead in the journey. And if you're two or three steps ahead of maturity, they can help them get to where you are. And you can create content or media, whatever you're doing, you can create stuff that's going to serve them the following month, the following year. That's, I think, at least in my experience, that's how you build something. Because then you're like, you're a few steps ahead. I have a feeling this is what you're going to need in 2024. Let me go on and build that. And having the patience, the perseverance, even finding the resources sometimes to build on that level, will allow you to have a longer career, because then you'll be ahead of the game. And then people will be like, yeah, Ashley is exactly. She has his voice where she already knows where I'm going. Right. You know, I mean,

Ashley Mejia: 26:56

that's so good. So you shared so many gems within that. But thank you so much. When you mentioned that it was about 10 months from when you started Cutler to when it was acquired.

Damon Brown: 27:08

Yeah. September to July? I think so. Yeah. Whatever that is.

Ashley Mejia: 27:12

That's amazing. What are the biggest maybe the top two key lessons that you got from that experience from selling your app that you just started? That's amazing.

Damon Brown: 27:23

Wow, I said the number one thing is that you're not going to be for everyone. My mother always talks about this, I think about my mom right now. And so when we launched Cutler. Within a week, it became the number one app in several countries. So America, Canada, Germany, for some reason, Australia, I still remembers these countries. They need hugs. They need hugs. Exactly. Right. And I think we had 100,000 downloads and 10,000 completed hugs, which is like our metric within the first week. At the exact same time. I'm given this context for a reason. It's not a humble brag. I've given this for a reason. The exact same week, we were roasted on the late night talk shows and the morning shows, and by my former freelance contributor contribution publication, the New York Post, so we were getting roasted.

Unknown: 28:17

That's how you know you made it right. If you're on

Damon Brown: 28:21

if you're on page six, whatever the equivalent is now. Exactly. Now, it was like the Kelly Ripa and Michael Strahan at the time show, you know, the morning show, and they're ripping into color. Go on YouTube do a Google search for CUDD. LR they were ripping us a new one, as they used to say. And what we realized was the one all press is good press. In that case, it actually after people are like, why are people talking about this app all of a sudden, so then Pete more people download it, of course. But then I also showed that there was a specific audience, Seth Godin calls it the minimal viable audience. So the people that really get the stuff that you're doing, you hone in on them. We could have been like, Oh, this is embarrassing. They're making fun of us. Let's pull the plug. But we didn't, because we were serving the audience that we intended. A lot of people that I coach and even myself, sometimes we get we get lost in that. Because we're like, oh, okay, well, this book only sold 100 copies, so I must not be doing it. This is a fantastic quote and I'm going to mess it up. So forgive me for all you all you Hardcore History buffs. But I believe it was the Sex Pistols Nevermind the books, which they're a punk band very late 60s, early 70s. Sid Vicious and other folks were in there as well as Yeah, anyway, big detour there. Their album didn't do very well at all. It bombed. But the saying is that every person who bought a copy of their album started in a punk band. And so perhaps the Ramones much later it'd be Green Day, you know, which is more in my generation and 90s they got a copy of that Sex Pistols album and They did something with it. That's as I was talking about with my book, bring your worth. The sales were rough. I just had a best seller. And I'm like, Oh, wow, okay, maybe this is a rat. But the people that got the book, got the book. And then now they're doing cool stuff. Because they let me know, they're like, hey, this inspired me to do this set in the third. And so to not mistake, the numbers and the quantity for you not hitting the people that you want to hit. So that's like the biggest lesson number one from us working with coddler, especially after the acquisition. It's like, of course, but while we're going through it, it was not quite as clear. So the second thing is knowing when to stop. And it was shortly after Valentine's Day, where I ended up, I would have morning meetings with my other co founder, because the third co founder was more in the background. We'd have morning meetings. And I remember getting up super early in the morning, because that's when I would work with them. And we got on our zoom call, or whatever the equivalent was. And I was like, I think I think this is it. And he was like, Yeah, this is it. Because we knew that we accomplished whatever we were going to accomplish. And for me, it was showing that technology can be used to connect people rather than separate people. We got a quarter million users like, okay, so then when we have that conversation, that's when the call started to come in as far as potential acquisition. But we knew that that wave had crested, we did the very best that we could, again, we're on the cover of The Wall Street Journal, like, we already created this economy using their terms, the cuddle economy. And so there are professional cuddlers people who you get paid to give hugs. They were apps, like clones was an amazing period of time. But we have a number one app in the world twice until August 14 2015. And so it's like, okay, at a certain point, you have to know that there's another row for you and beyond. And and that's when the acquisition happened. But if we kept doing it for like, another 10 years, will we just be writing it out? Will we just want to with the fame that was connected to Cutler, will we be afraid to quit and be like, let's move on to the next thing. And I think if you're going to make an impact, you're going to have that bravery to say, Okay, that's enough. Again, with the bytes, this entrepreneur had a certain tone, and it became a best seller. And I also knew that the people I was serving need to have a different conversation. And so even though they weren't comfortable with a left turn, I'm like, but I have to make the left turn, and that hurts. But in the long run, it's like, oh, no, but that was exactly what they needed. I just might have been a little bit early with it. But again, my argument is that you're supposed to be a little bit early. Otherwise, why are we the experts? How are we serving our community, if we're just sitting with them, we ought to be a little bit in the future.

Ashley Mejia: 32:50

I love that. I love that. That's really, really good. And I think it ties into something that I was reading, where you talk about the concept of serving this audience needs before even others recognize the value. And it sounds like that's a superpower that you have in being able to kind of anticipate a what's coming a what the audience would need, but also be there first in the market before would be competitors see the opportunity? Like it sounds like you're kinda

Damon Brown: 33:20

Well, the only pushback I would give would be, I think as as cultural tastemakers as media people. I think it's superpower that all of us can develop. Like, I don't think I'm unique in that. If I was unique in that, I wouldn't be a business coach. Because then I'd be like, No, there's something I understand. No one else could ever say. I'm not gonna go to anybody else. This is like no, I believe this is, as journalists as creators. I think we have that instinct developed. I think the challenge is that we don't always trust that instinct. So when my first major book, I want to say I got 42 rejections, there was a lot. Wow, there was a lot. And the book came out, and it made an impact. But the publishers I was speaking to, it wasn't even New York, it was like New York, LA San Francisco, I was talking to all the publishers, but they didn't see the vision. But I did, because I'm part of that culture. So that's, that's what I mean by trusting it. Not trusting as far as not hearing it, but not trusting as far as not going with it. Like, if someone wanted to do a book on how to work remotely, and they get the book and they were pitching the book in 2018. Then I've been working remotely for a while because I have some international clients. I would buy the book. If I was the publisher and be like, Yes, I publish that book. But a lot of people wouldn't. And then six months later, everyone's remote.

Ashley Mejia: 34:44

Everybody needs that book.

Damon Brown: 34:47

Everybody needs three copies, not to mention virtual schooling, and some great people in ASj, who have specialized in homeschooling for years, and suddenly their books are on the bestseller list. As a lot of us because Know Your kids are similar age to mine. So it's like I was a virtual schooling, a lot of us are still virtual schooling, the whole thing. But if you don't listen to that instinct and go with it, then that's a lost cause. And the worst feeling in the world is interacting with a creative who have that insight. But because other people didn't cosign that idea, they didn't go with it, and then ends up being a large organization, another creator, or even in the case of the pandemic, and circumstances change. And that brilliant idea is still on the shelf, and it's too late. That hurts. That's why I'm really into the side hustle. That's why I'm really into trying to find ways to get your idea off the ground without using all your resources. Because if you're able to do that, again, that's why I have 26 books, like they're just, they started little sparks. And I keep feeding the flame and keep feeding the flame, whether it's through the ink column, or ideas that I get, as I'm doing that bring your show, or even ideas for my coaching clients, I'm talking with them, they're dealing with particular struggle, and I'm like, you know, that would actually make a really good episode. And in that episode becomes career remix my book from a couple years ago, like, all those different pieces, they're all there. And our job is to, with the resources that we have is to move them around and start to piece that together. So it can serve other people. And if we come from that angle, then it's actually not that difficult. And then that requires, like we talked about earlier, to go deep, and be embedded into this community that you want to serve. I don't serve people in the C suites. So I've had some coaching clients in the C suites. Nothing wrong with that. But that's not my primary audience. I don't serve people that are trying to get to next level in their traditional corporate job, a couple people I've coached I've been in that area, not so much. My thing is not traditional entrepreneurs. So Minimal Viable audience. So because it's so narrow, I'm not writing for anybody else, that allows me to be a lot more productive. And so the more you focus on, again, the people you want to serve, and don't be afraid to say no to the things that don't fit the people that you're trying to serve, then the more I think, outputs not the right word. But the more in tune, you can be as far as creating and serving the audience that you really want to want to care about. I think we get into trouble when we start to dilute the different things just because we feel like that's what Playboy magazine wants. That's what I write for AARP. So that's what AARP wants. That's what this book publisher wants. So I better change my message for that. I think there's ways typically with all the technology, we have to build that Minimal Viable audience, and to be embedded, like a war reporter, to be embedded in the front lines, and help them get to the next level. But you absolutely have to make a choice. And some folks don't want to do that. And that's okay. For me, though, that's been the secret to me being as productive and hopefully impacting folks as much as as I felt like I have.

Ashley Mejia: 38:07

I think so I think that's the key, right? Because even from just the consumers perspective, or the you know, in your case, these the solo entrepreneurs, the Freelancers, it is such a special world, it's different from corporate, it's different from having, you know, a small business and having like, a staff of 15 people, this flavor of entrepreneurship is so specific. And when you were talking about just that ability to serve, and just knowing what they need that comes across, because everything that you're putting out is focused on them. And so when they see it, it's so refreshing, they feel like I'm home, you know, I've found somebody who gets me, I found somebody who understands my specific piece of this entrepreneurship pie. And I think it's just a match made. And you know, just beautiful things can come from that because you're in tune. They're in tuned, and you can go forth together and just this a synergistic way. It's, it's really cool to see.

Damon Brown: 39:06

Yeah, thank you. And I agree with you, there's going after the depth instead of the bread. And if you're going to be in the game, with ups and downs of freelancing, independence, bootstrapping your companies and ever got VC or venture capitalists, funding for either one of my startups, if you're going to be in the wild, wild west, let's put it like that. Then you need to make sure that your horse is strapped on you, I mean, need to make sure that you you have a compass instead of a map because you need to go near where the understanding where the geography is changing, as opposed to the way it was. Whatever analogies you want to use, you need to go for depth. Now if you end up having something where it's more structure, then maybe you don't need to do the depth as much. But if you're going to be in this for the long haul, eventually you're gonna have to work on a deck but we'll get to

Ashley Mejia: 39:56

that's beautiful in your ASj talk you We're sharing a lot about AI. And I know in there your coaching work, you're really focused on helping creative people develop ways to establish their passive income. And this is such a, I feel like a topic everybody's curious about they want to know. And you've been able to really leverage AI. No, you were using mid journey. And you've been able to really, really make something of it and use it for products to create books. how can listeners use AI to work smarter and maybe create some digital products the way that you have?

Damon Brown: 40:32

That's a really good question. I think the first step is to take the technology out of it, which might sound contradictory, in fact, it is. But to figure out again, who do you want to serve. And so in my case, I have my in the same book, The by Selectric north from 2016. And I use mid journey, which is a tool where you can write in that particular picture description, and then it'll design the picture for you. It's very magical, it's very strange. I've been using it for almost a year now. And like a lot of AI guides, it feels like there's some elves in the box, they're very Keebler. So I use that, to do a semi animated slash illustrated version of my audio book for the bytes is entrepreneur. And then there's 21 chapters, like I mentioned. And so for 21 weeks, every Monday, I was premiering a new chapter. And with my larger audience now, on the bring your show, I realized a lot of them didn't know, the vices entrepreneur, says my show premiered in 2020. The book came out in 2016. So it's almost like a different phase of my career. And so I'm like, How can I package this in a way where I can serve the people that watch, bring your worth that TV, and also repurpose can't think of a more clinical term, but, or less clinical term, but repurpose the content that I've already created. And because I self published it, I owned the intellectual property. So I don't have to call an agent and have to get permission from a publisher. I was just like, Yeah, I'm gonna do this, I just kind of ran with it. And so in this case, it was a way to serve the natural entrepreneurs, who were getting to me through the channel, and or didn't know me back when book came out almost 10 years ago. So I think number one, it starts with thinking about who you want to serve. I think a second part is seeing how technology can be a partner or an ally. That doesn't mean you you plug a bunch of stuff, or write a bunch of stuff into the hottest AI platform, and then it spits out an article for you. And then you go and try to publish the article, it doesn't mean that what it means is, let's say if you want to improve an article that you've written, that means maybe using that AI tool and say, Hey, can you give me some insight as far as how I can make this article stronger? Or even taking a step back? Smithsonian, as I mentioned a couple of times, that was my dream publication when I first started freelancing. And so if that existed back then because well before AI took off. But if that existed back, then I could do the query that I spent two days writing, no exaggeration, of course, Smithsonian, that's what the mail through the mail system. Right? Cool. Right? And do the safety that self addressed, stamped envelope, I'm gonna tell you how old I am, right, but putting it in there. And I, you know, printed off on my dot matrix printer. If I the equivalent of some AI platforms, I can go in and put in the query and say, hey, where does the grammar not quite match? Or how can I make this more persuasive. And then, maybe all these years later, maybe I would have been a regular regular writer for the Smithsonian, instead of getting rejections from them. Those are ways that we can partner with technology. I am not an artist, as I mentioned, our NAS J. Kino. And so my journey in this case was able to animate, make these beautiful illustrations that I couldn't do if I had a gun to my head. So it's doing the things that I literally cannot do at this period of time in my career. And so for me, that's a smart way for creators use AI, not to look at it as a replacement for our job, not to look at it as a hack. So we know, we can work a lot less more about what are those things that AI is really good at, there's a wonderful term that I or quote that I say probably about once a year, or think about once a year. And that is, if you have a hammer, then every problem is a nail. So in other words, if you're saying, or I'm just going to depend on this one platform, and doesn't have to be AI, I'm just gonna depend on Facebook to build up my community. I'm just gonna depend on LinkedIn for this. I'm gonna depend on chat GPT for this kind of mid journey for this, and that ends up being all where you put all your eggs into all your resources. Eventually that technology is going to get old and or it will pivot and or your community is going to want something more from you. And what you want to be is to be ahead of the curve and say, I'm partnering with mid journey right now, but Next year, maybe my show will be on the vision Pro headset that Apple just announced earlier this year. That'd be cool. I'm not going to pretend that I'm not looking into it, right. But that's partnering with technology, because I can't make anything 3d, but Apple can. And so that's what I mean by still serving that same audience still creating, personally, my work hasn't changed. Even with new technology, I'm sure your work isn't going to change. What happens is that it gets augmented, as you partner with technology, but you're still serving the same audience. In so many cases, were given the same message. It's just a different medium. And that's my one soapbox, as I've talked to you, fellow creators, and particularly fellow journalists over the years, is that we keep falling into the trap that when a new technology comes in, suddenly we're gonna get wiped out, or we need to put all our eggs into that basket. But then we don't realize that the following year is gonna be another technology. If you and I were having this podcast a year ago, we will be talking about how you can get into the metaverse, right? Yeah. Yep. Facebook, as of this recording, a year ago, Facebook didn't even change their name yet. That's how quickly it moves. And being a tech guy, I'm all like, oh, no, no, no, no, no, we're not going to. Yes, I'm partnering with me journey right now. Just like I partnered with, I had a bootcamp on teachable that was three, four or five years ago, teachable is going through a lot of stuff right now. So my bootcamp isn't available on there. Like it was by partner with that technology to coach people, that technology is going a different direction. A year ago, I had something on decentraland, which is still available on decentraland. If you want to look it up, decentraland has gone down. So now there's other ways to get the message out. But it's still the same message. And as creatives, we need to think about that where we don't want to be wedded to a certain technology, particularly nowadays, technology moves way too fast for us to say, we're going to make an impact on the world based on this one particular technology. That's not the way that we want to approach this. But we want to approach this to say, Who do I want to serve? How can I partner with technology to serve them better? And how can I create in a way that's agile enough? And evergreen enough? That's where I'm looking for evergreen enough so that that message will ring true no matter what technology? People get it on?

Ashley Mejia: 47:26

So good. So good. Thank you so much. So you've done, we've been here talking a while, and you've done a lot. And so I don't want to I want to make sure I respect your time. I could talk to you all day. So please, yeah, this is great. I love this. I love this. So you've been accomplishing all of this. And also being a partner, to your wife and a dad to your two boys. And so many people that I speak to that are in this talk freelance to me audience a lot our women a lot our caregivers, both, maybe they have kids, or maybe they take care of their nephews or nieces or have aging parents aging aunts and uncles. And so that ability that flexibility and freedom that our nature, our freelance or independent work offers is really important. How have you been able to balance your responsibilities as a parent? And then all of these entrepreneurial pursuits, you've been so successful at them? How? How can we learn from you in that that regard?

Damon Brown: 48:24

Thank you, I'm gonna take that last piece and run with it. You have to define what your metrics of success are. And so my wife said, I worked from home about two, three years ago. She's a pediatrician, and the amount of stuff that was happening, you can imagine, she was like, I need to shift things. So she's working from home. Now, before that period of time, she had a traditional job as a pediatrician, and it would just be like me and the boys hanging out. My metrics had to change, as I talked about with, and I talked about this in the bytes of entrepreneur, again, that's part of the compilation that's coming out in October. If I was looking for what I did with my first startup, so quotable, it took me five months to do that. If it was with someone who knew technology a little bit better, and or didn't have kids, because my son was born a few months before I started so quotable. And so if it was someone who didn't have kids, or wasn't married, or had this kind of open schedule, that we all had a one month period of time in our lives, then I could have done so quotable in five weeks, my friends in Silicon Valley, and we had just moved to San Diego. So my friends in Silicon Valley where we had just laughed, they couldn't get in five days. And I was aware of that. And it's really hard when you know something's taking you what is that? 200 days 150 days is that you 150 days and you know that your colleagues in SF in San Francisco could die in five photo either remind myself though is that I wasn't gonna drop the bought with Alec, our first son, I need to take care of myself. And I'm a new dad. So I don't know what the hell's going on. And I'm still trying to bring in income, right, because I'm still freelancing. So I'll start writing for Playboy and others, some still freelancing, try to get this app off the ground, and then take the leave with our son during the day. So I had to give myself grace. And the best way I found, when you got little, little tiny human beings at home, it's actually give yourself time. So if you actually stretch the time, then that comparison game gets a little bit easier. And I gave myself that time, and that cut out the door, and it did what it was supposed to do. And if I didn't do that, then there'll be no Kudler. Right, there was no cut, right? There's no color, then there will be no business coaching, no, Ted Talks, none of that, like, Oh, that would be gone, I'd be on a different path, I'm sure I'd love the path I will be on. But that was like the seeds of that. And if I allowed myself to get frustrated, because I was using somebody else's metrics, or the metrics of my old life, then I wouldn't have made that I would get too frustrated. So that's like the number one tip I can give for people who are ambitious, like me, you got to stretch the timeline, you have to, I mean, to stretch the timeline now, you know, and our kids are like seven and about to turn 10. They're at camp right now, you know, with the summer camp and all that, which is great to have that break. But my wife and I are still on in the morning, getting them out the door. And then camp isn't necessarily all day. So then I was calculating it. And I'm like, I still have like 30 hour work week, while the kids are right. You know, I mean, where it's like I can just focus put on, I have a speaker behind me put on my favorite jazz or hip hop or whatever, and zone out and focus on the show focus on my coach clients. That's it. So I still even have the time for a full time job. And they're seven and almost 10. So again, we're kind of in that zone, where if we have a young family, we're going to have to stretch a timeline. The second tip I would give, and I talk about this kind of a theme in my books, is that if you run away to the circus, you are eventually gonna have to come back home. And what I mean by that is, if you say I'm just gonna focus on my career stuff, yeah, the kids will be there, they're getting on my last nerve, you and I can both relate to that.

Unknown: 52:18

100%. Yes,

Damon Brown: 52:21

let's keep it honest. Now, what my kids are just getting on my nerves yesterday, like, so they get on my nerves, their two boys. So they're fighting over stuff, because they're close in age or whatever, whatever the dynamic is, or they won't sleep at night, because you're breastfeeding, whatever dynamic is, that's gonna go away, hopefully, for good reasons. And they get older, they mature, they hit puberty, whatever happens. And then you still think that your role is there, I'm just going to put this to the side. And let me focus on this. Let me focus on this new shiny object. And as many parents have said, way wiser than me, the days go by slow, but the years go by fast. So you go into your grind. Again, we both relate to it to your grind. And it's so easy to get frustrated in that moment. And that's what I'm so thankful for. With, particularly the journey with cuddler, and the TV, and the newspaper features and all that stuff and acquisition, and all the pomp and circumstance. When we sold the company, then all the spotlight went off, right? Because we sold the company, it's like we're not founders anymore, right? And then it was just me, and our two year old, and our kid who was about to come later on beginning of the following year, we just found out we were pregnant shortly after. And that was it. That was my entire world. Imagine what would have happened. If I did the proverbial running away to the circus, and soaked up all this stuff with the ego and oh, I'm the stuff now. And oh, yeah, I have a number one app in the world. Oh, I did it again. Oh, I got it twice it we got a quarter million users. We sold the app. And then what's where's my identity? I think there's a parallel here to to the other extreme, which my wife and I talk about, because we both deal with that. But a lot of people that I coach who have little kids, particularly who are women deal with this, as far as going in the opposite direction, where their identity is, I am mom. That's it. And with me take the lead on a lot of the stay at home parenting in the beginning of getting that I could have fell into that where it's like, I'm dad, but they don't need that, like they did 10 years ago. You're in a few years, even last year, I can see they're starting to get their distance, which is cool. That's their process. My wife's going through the same thing. It's like, it's like no, we don't need you quite as much. And so particularly, I found this for women, that can be a dangerous area to where you know, putting your career on hold and saying I'll do that. Look later, when they're grown, but they're going to be grown. And then you're going to be 20 years down line. Like, we do the math like, they're in college, it's been 18 years. Yes. And so I'm trying to help all of us find that balance between the two, not running away to the circus and saying, I'm gonna work on my book and forget these kids. But then not going to another camp either, where it's like, no, these kids are my life, I will do anything for them, and I'm not going to progress at all. And then you know, 1015 20 years pass your careers at the same place. And hopefully, you still have some type of career. Hopefully, you can still resonate with audiences that you left behind 1020 years ago. And I think about how, if I waited until our kids were at the point they're at now where they're a lot more independent, that like so quotable Kudler, about his things, try to do that. Now. There's a pandemic, like, there will be brettler. Like all that stuff wouldn't exist, unless that balance was held. And so that's a biggest recommendation I can give is try to find some type of small way to make progress as far as impact on people you want to serve, even in the smallest way. A newsletter that comes out once a quarter fine. Do that, a YouTube show that you are able to get off the ground, you do an episode once a month, and it looks like crap. Again, you can look at my earlier episodes, they look awful, but I have so much pride in them because I started. Exactly. That's it.

Ashley Mejia: 56:34

So good day, man. I know the audience is just going to be so inspired by this conversation. I know you've got the book coming out October 20. And people are gonna want to follow up with you and follow your journey. Where can people find you online if they want to learn more about your show about the Bring Your worth show, and all the things you have coming up.

Damon Brown: 56:55

Thank you for having me, Ashley. So the complete bring your worth collection is available for preorder. They'll be out October 20. You get it on Amazon or any other major bookstores, the Kindle versions preorder and the paperback preorder should be up by the time you guys listen to this. You'll also get signed copies from me at David brown.net as well as the different merch that has such as supreme your worth while again, other things that's all plays part of passive income. So I'm trying to walk the walk as far as the stuff that I'm talking about as a coach, if you want to coach with me, you can also learn more about that David Brown that net and if you want to watch the bring your work show it's at bring your worth that TV. So finally changed the the websites, I'm excited about the new URL to come over and visit me there the subscribe for free as part of the YouTube system at the moment. And I just hit about 300 or so episodes, you know, so if you're new to the show, have fun. And it's talking about a lot of stuff that Ashley and I talked about today. And yeah, thanks for having me. I'm geeked out to this conversation and the questions that you've asked and the feedback that you've given has inspired me to so thank you, Ashley, keep doing what you're doing.

Ashley Mejia: 58:00

I appreciate it so much, Damon, thank you for being on the top freelance TV show. Absolutely. Thank you. And with that, we've come to the end of another episode. Please make sure you hit subscribe if you haven't already done so. And give me a five star review on Apple. This will help out a lot and getting the word out about this brand new podcast. I invite you to check out the show notes and also grab my free niches get riches, freelance writing worksheet to brainstorm the best niches for your writing business. If you're not a writer, you can still use it to get business ideas. And until next time, this is Ashley a talk freelance to me. Don't forget, we all get this one precious life. Don't constrain yourself to a box that you were never meant to fit in. It is your right to profit from your own creative gifts. This podcast was created by Ashley Cisneros. mahiya our music was composed by Don Rafael of world instrumentals talk freelance to me is a product of Phoenix creative studio