TBJA 330 5 Ways To Maximize Your Entrepreneurial Time, Damon Brown

Damon Brown: "Cuddlr allows you to connect with people around you for hugs. You pull out your smartphone. You see who is in the vicinity, who is up for a hug and you connect with other people for that. Strictly platonic. We actually launched it; myself and my two co-founders, we launched it in September of 2014. Within a week we had 100,000 users and we were the number one app on the Apple App Store.
"
Phoebe : “Wow!
"
Damon Brown: "It was a wild ride. Yeah, I could probably talk about that for a long time. Especially if you talk to other co-founders, you could talk about your creation forever. We did that for almost a year. We bootstrapped the whole thing. No outside investment. It was crazy. Then we got acquired [?] around the 11-month point. That was a beautiful experience. Very intense.
"
Phoebe : "Oh my gosh! All right. You come from a background of entrepreneur and journalists. Tell me, where did the idea come from? How did this even come about?
"
Damon Brown: "Sure. To take a step back, I actually got involved with entrepreneurship when I was living up in Silicon Valley and I was covering Silicon Valley things, like the new iPhone launch and all those things for the New York Post and for Playboy and other publications. I came up with an app idea that allowed you to capture other people's quotes, which is a very journalist type of thing to do.
"
Phoebe : "Sure.
"
Damon Brown: "With that idea, I started this app called So Quotable, soQuo for short. In the process of doing that app, things got a little complicated. Some of the support that I thought I was going to have, I didn't have. I ended up doing it all on my own, even though I had no intention of doing that. That finally came out. When that came out, it was successful enough to get the attention of two other people who came up with the idea for Cuddlr. We ended up connecting. By the end of the summer, we had the app out and it flew like hotcakes. It was crazy. Yeah.
"
Phoebe : “Wow! what a ride. How fun was that? It's a really cool idea. I'm curious about the demographic. What age bracket does it mainly attract?
"
Damon Brown: "We were totally up and down. Yeah. I'm really into stats. I've written several books and a lot of them are about intimacy and technology, as you mentioned. This is my research deal. This is how I've made a living for a long time. I was all about the statistics and figuring out who was actually using our app. We had it broken down into countries, where I think New Zealand was a major country for us because we were an international app. It was United States, Canada, New Zealand. It might have been parts of Germany and another area that were very popular. As far as the demographics, they were really all over the place. They really change based on the areas.
"
"For instance, in San Francisco, which tends to have a slightly younger population, or Miami, then it would skew younger. If you're in New York and have a slightly older population, at least for all the boroughs, then it would skew higher. It really changed based on the demographics of the actual area. It was a fascinating thing to do.
"
Phoebe : "I've got one last question about this and it has to do more with the legality of it because I've always wondered when you have these apps that connect people. What is the back story on that? From a journalist standpoint and a legal standpoint, when you're bringing people together, is there anything required? Are there any legalities with that? Talk to us about that.
"
Damon Brown: "Totally. That was legitimate. Again, with the background being journalism, I was like, "Okay, can we do this? Is this going to be okay?" We put in a ton of safeguards in the actual technology. With my co-founder who was working on the programming, that was something that I was very specific about. I was like, "If we're going to go forward, we'd have these safeguards." Any information on the people that you're connecting with is saved within the app but not actually on the phone. As soon as you stop using the app, then that information is gone. Things like that are for a safety measurement standpoint. We have had a ton of check marks with that.

"As the app came out, I had a close eye on things to make sure that everybody was safe with the experience. Again, being a Silicon Valley reporter, I saw some of the crazy stuff that happened when people were reckless with that type of thing. Unfortunately, there could be a mentality of just getting the thing out and the technology will solve things. (“We'll just get it out and we'll work on it later.”) With Cuddlr, I made sure that we had an opposite experience, where we really wanted to develop a culture around the app and then release the app. The app could have been ready a little bit earlier that summer, but we didn't release it yet because I wanted to make sure the culture was straight. We're very fortunate. It was a good experience.”

Phoebe : "Absolutely. Smart move. I think here we say it all the time, to "think like a journalist." We're in journalism community. As you listen to this, it shows that it pays off because journalists just think about certain things like that, that often don't come into play or somehow get overlooked when startups are racing to the finish line. Good for you to consider all those aspects. Usually that comes from a background in covering all different kinds of stories, from tech to murder stories to things like that, that give you this exposure and this wide background of experience in these areas to know, ‘Hey, we've really got to make sure that we've got that checklist and we're checking it off.’"
"
Damon Brown: "Definitely. We end up getting very proud that we got the cover of The Wall Street Journal a couple months after we launched and also got The New York Times, too. For me the nightmare scenario would have been those things happening for the wrong reasons. That's the only reason why I bring it up, where it's like I don't want us to be the cover story for an app that went wrong. We did everything that we could to make sure that our users were safe. I think by the time we wrapped up, we had about 250,000 users. Somewhere around there. Everybody was okay. Knock on wood. It ended up being a really good experience I think for the users and also obviously for us, too.”

Phoebe : "Well, Brand Journalism community, we have jumped right into this. I just knew that would be top of mind. I wanted to address it because Cuddlr, it just makes you go, ‘What? What is this?’ What we're talking about on this episode, though, is 5 ways to maximize your entrepreneurial time. As you can imagine, Damon has a lot of things going on, a lot of things that he's juggling. He's going to be able to unpack that for us. Real quickly though, I don't want to miss your icebreaker. You've lived in 20 locations in 6 different states. Was that for your reporting career? Give us a little insight.”

Damon Brown: "No, actually. That was just part of my life because, very briefly, my mom had remarried. Then my father had actually gotten different jobs across the country. I'm originally from South Jersey, Atlantic City. Then we lived in a few different places in South Jersey by Philadelphia. Then briefly in Ohio and then I had my teenage years in Michigan. I got my degree from Oakland University in Detroit in journalism and then I moved to Chicago to get my master's in magazine publishing from Northwestern. I moved down to New Orleans to write a book and I actually left with Hurricane Katrina. Then that moved me to California to be closer to my now wife. We've lived up and down the California coast because of our various career pursuits and finally settled down in Southern California.

"It's been a wonderful experience. I take pleasure in that and I'm happy about that because I think that's informed my thinking. When we did create something, when I became an entrepreneur with So Quotable and then later, Cuddlr, when I talk to different people as a journalist or as an author, when I connect with different entrepreneurs and try to give them guidance and advice, there's different perspectives that I try to respect. Because of all the different cultures I've been exposed to and all the changes that I've been through as far as being a young adult, I think that's helped me with that, but particularly. being a journalist.

"One of my favorite mentors said that, "Anything that happens to you in your life as a writer is just grist for the mill." That gives you so many different perspectives. When someone says they lived in New Orleans, I'm like, ‘Oh, I lived in New Orleans’. We can talk about that. That might actually be a connection point to a source or a connection point to a potential user for the app or what have you. It just makes you a lot more well-rounded and I'm really thankful for that.”

Phoebe : "Well you are just bringing so much valuable information. I'd like you to weigh in on this "think like a journalist" quote. It goes like this: ‘You shouldn't focus on why you can't do something, which is what most people do. You should focus on why perhaps you can and be one of the exceptions.’ That's Steve Case, who is the co-founder of AOL.”

Damon Brown: "Sure. Nice. Yeah, I absolutely love that quote. One of the things I talk about in the Bite-Sized Entrepreneur book series is you focusing on your core. Figuring out why you want to do something. Of course that's connected to passion, but people often focus on their skill set. They say, ‘Well I can't do that.’ For me with some of the work that I've done, I didn't have that in my skill set. I had never been a founder before. I programmed when I was younger but I hadn't programmed at all when I was an adult. I learned how to do that. Particularly in the Internet age, those skills are so easy to come by. It's just a matter of having the discipline to do that. The bigger issue that we have is figuring out what our ‘why’ is. What's our purpose?

"If we figure out our purpose, then I think we can do anything. We can just learn that particular skill set. If we worry about the skill set, I feel like that's a waste of time. I think that what makes you an exception is focusing on what you actually care about and then building your skill set based on that.”

Phoebe : "So well-said, Damon. Let's go a little bit back in time. You've shared a lot of your backstory already, but take us back a little bit more. Maybe even why you became a journalist. What made you passionate about that? Then, if there is yet another highlight that you'd like to share, feel free to share that. We know that you've hit top ranks in the Apple Store with your app, Cuddlr and been on the cover of Wall Street Journal and The New York Times. So much good stuff. If there's one that I missed, share it with us now.”

Damon Brown: "Sure. For me I was pretty much born to write. My mom and my dad said that I was born with a joystick in one hand and a typewriter in the other. I'm actually very much dating myself, too. ”
“"
Phoebe : "I'm right there with you.”
"
Damon Brown: "Okay. Right. I've always been a storyteller and I've always been fascinated by technology. It wasn't until well after undergrad, where technology started to become a regular part of storytelling and vice versa. Until then, I was an outlier who really cared about software and programming and technology and also cared about the written word. And I read tons of books and was on the journalism staff of multiple newspapers and magazines. It wasn't until I started my freelance career around 2000, where things had really started to come together. That ended up being a huge advantage because now if you want to be a journalist, people say start a blog or start a podcast or start writing online. To do that, you need to understand technology. I'm really glad at this point that I was born at that time, because that gave me a huge advantage to get started for taking my freelance career seriously.

"Probably my proudest moment was again, when I was working on So Quotable. I had some colleagues who were going to help out as far as with the technology, essentially do the programming for me. At that period of time, I got involved with the TED Conference. I connected with them. They had just started a book line and I ended up doing a book with them called Our Virtual Shadow: Why We're Obsessed with Documenting Our Lives Online. Again, the connection between intimacy and technology. I did the book with them based on some of the research I did with So Quotable. I mentioned the app in there several times. The book came out. Now I'm on the hook where the app absolutely has to come out. At that period of time, I had just gotten married, found out that my kid was going to be on the way shortly after that. We were just rolling. The folks that were going to help me out bailed.

"Fast forward 9 months later, of course, and I'm a stay-at-home dad. My wife is about go back to work. I told this huge audience of TED readers from the conference, which I still immensely adored, that this app was going to come out. What happened was I started waking up at 3:15 in the morning. There's a huge story behind that that I've written about. I talk about this story in the Bite-Sized Entrepreneur, where I started getting up at 3:15 in the morning and my son would wake up every morning at 6:00. That would give me 3 hours to program, to do the media for it, to do whatever I had to do to make sure that came out. Now I went through that for about 3 months and learned how to program it, the whole thing. As soon as the app was almost done, I was 95 percent done, TED called. They said they wanted me to speak. They had no idea where the app was and all that stuff.
"
"I end up speaking at the second stage of TED up in Vancouver about some of those things that I had learned. I'm so proud of that moment. Number one, because I was able to be there for my son during the day. Hence me working from 3:15 to 6:15 or so in the morning for those 5 days a week. I was able to be totally present for my son and be a good father, but also that I didn't quit. It would have been really easy to quit. Everyone, I think, would have understood, particularly, I think, fellow parents. They would have got it. I didn't. Thank God I didn't because TED ended up calling and they wanted me to talk. Me going up there not having launched my app would have been a travesty and really sad. That's probably my proudest moment. Yeah.”

Phoebe : “Wow! What a great story and what stamina! That is tough. It reminds me of my anchoring days, getting up that early in the morning to do The Morning Show. That's tough when you're doing that and then you've got to be a parent all day. Well we've heard a struggle already, but I'm wondering, is there another story that you want to tell? A moment in time when it didn't work, when you really had to dig deep, find correction is direction.”

Damon Brown: "Yes. There’re several. Just pick one, I guess. I had actually self-published a book called Damon Brown's Simple Guide to the iPad. I had launched it right when the iPad came out. Wrote it within a week, self-published it onto Kindle. It went to number one and ended up being a bestseller. Super proud moment. Excellent stuff. This was back in 2010. It was probably the first time I even dabbled in any type of entrepreneurial activity. Shortly after that, I wanted to do another book of a similar vein. I won't even mention the name of the book. I was like, ‘You know what? I did it once. I'm going to do it again.’ This time I didn't have an impromptu team. This time I didn't talk to other people about it. This time I didn't spend much time on strategy. I launched it and I think maybe one copy sold. It dropped like a rock. It was a moment of extreme humility, which I'm starting to get used to but it's part of the cycle.”

Phoebe : "It comes with it. Yes.”

Damon Brown: "Oh my gosh! it comes with it. Even looking back now, I'm like, ‘Oh, what was I thinking?’ It's a good 6 years now and I still wince when I talk about it. It was this moment where with the Bite-Sized Entrepreneur and I have a new followup called the Productive Bite-Sized Entrepreneur, which focuses on productivity, and I'll share some of those tips in a minute, but with those two books, those are self-published. I have a gang-load of support with me. It's strategized, it's organized and it's doing well, both of the books. All that is learned from that 6 -years -ago experience of falling on my face. I thought I unlocked the mystery. I was like, ‘Oh, yeah. I can rock this. Let me self-publish another thing.’ Obviously I didn't know what I was doing.”

Phoebe : "What's interesting, though, is that you published the first one and you couldn't have possibly known all the details of that, but that's the one that did really well and it's the second time around that it didn't work out so well. What was the difference then? I get that you say you didn't spend as much time on strategy, but are there any other specifics? Why did that first one do so well?”

Damon Brown: “Well, one of the reasons why it went so well is because of the timing of it, because of the iPad launch. It was the most popular new device probably within 5 years. Talking on the success part, that was a big part of it. As far as why the first one succeeded and the second one failed, one simple reason. In the first one I assumed I didn't know everything. I checked everything. I made sure my stuff was tight. Then, with the second one, I assumed I knew everything. I was like, ‘Well I can do this.’ I didn't check to make sure there weren't any competing books as much. I didn't make sure that every detail was good. I think I did a good job but, compared to the job I usually do, it wasn't as good. There were so many factors. They all led from me thinking I knew all I needed to know. Here it is 6 years later. I just self-published my 4th book and I'm still learning. Having that reflective mentality was a big part of it.”

Phoebe : "Oh, absolutely. Just give us an idea, what was the topic of the 2nd book?”

Damon Brown: "It was actually on social media.”

Phoebe : "Okay. I'm a journalist. I'm going to dig a little. All right.”

Damon Brown: "I'm still scarred from it.”

Phoebe : "Yeah, I hear you. Only because we've got to watch the clock, I'm going to let you off the hook. We're going to move on. Let's talk about the top tips, 5 ways to maximize your entrepreneurial time. Take it away, Damon. Give us a look.”

Damon Brown: "Let's do it. Yeah. Number 1, the biggest thing, which is the theme of the Productive Bite-Sized Entrepreneur, is that productivity is a cycle, not a sprint. Do not expect to be productive every single day. That's setting yourself up for disappointment and perhaps even failure. I call it expecting to be an A student. You expect to get an A every time. You're not. There’re going to be certain days where your brain is going to need to rest. I talk about the cycle that I go through that has made me the most productive. I talk about that in the book series, but it was a 3 -part cycle that works really well for me. If we want to dive deeper into that, we can, but I talk about that in the book. It's worked really well for me as far as with all the productivity I've had.
"
"Number 1, productivity is a cycle, not a sprint. Number 2, and I already touched on this one: worry less about the skills and develop your core intention. I'm much more productive today because I don't worry about getting the right skill set. I worry about what my intention is. I have the book series. I have an audio book that's connected to the book series. I just launched a class on teachable.com that talks about the Bite-Sized Entrepreneur and creating a community. Me doing an audio book, that's my first audio book. Me doing an online class, I've done that in the past but I've never done one with teachable.com. Those things are learnable. You can learn those things. My main intention, though, that's something I need to know. That's something I need to always have in mind. That enables me to do different types of projects.
"
"Number 2, worrying less about skills and developing your core intention. Number 3, measure your focus rather than the time spent. I talk about this in one of the book chapters, where we have the Malcolm Gladwell idea of spending 10,000 hours doing something. That's a waste of time if you're not paying attention. For my personal example of learning programming and development and design to get my app out there for So Quotable, learning that within 3 to 4 minutes while taking care of my son, that doesn't mean that I'm extraordinary. That just means that I was intensely focused. Something that would normally take 10,000 hours only took me maybe 1,000. Anyone is capable of that as long as you know what your focus is. I think focus needs to be a priority rather than how many X amount of hours that you spend every day on something.

"Number 4, the more you develop a voice, the less you have to worry about your competition. I've been a freelancer for almost 20 years now and I've written several books. Some of them have to do with topics other people have covered. If someone else wrote those books, if someone else pitched those articles that I pitched, they would be completely different because of the 6 states and 20 places that I've lived in, because of my experience as a father, because of my life and my voice. Those things are so unique. The big advice I would give is for people to develop that voice. It doesn't have to be writers, per se, but your voice as an entrepreneur. With So Quotable and with Cuddlr, people look at that and they see a pattern with me as an entrepreneur, even though I just started 5 years ago. There's a certain pattern, a certain voice that you start to develop after you begin to trust and stop worrying about what other people are doing. That number 4 is develop your voice and worry less about the competition.

"Number 5 is probably the most crucial one and something that I still work on, it’s leave breathing room in your schedule no matter what. I call them blank days. Now, being a father, it's like you can't have a blank day.”

Phoebe : “Sure."
"
Damon Brown: "It's whatever. For some people who have looser schedules, they can do that. It might not be a day. It might be an hour or 2 hours. It's amazing. When you give space in your schedule, serendipitously, all these things will start to happen. An example I always give, which I always think about too in my personal stuff, is that if you have clients that you don't like and they're just paying the bills but they're barely doing that, and you don't give space for clients to come in who you really like, you're going to be stuck with the same clients because you're not giving room for these new better clients to come in. If you have the perfect client coming to your door but you're spending 80 hours a week on the clients that you hate, you're not going to have space for that.

"I think that's symbolic of so many other things in our life. That's one of the reasons why I am able to be productive right now because I try to give room for those things to come in. Cuddlr was something, a concept that came from someone else and they connected with me after the success with So Quotable. They knew that I researched technology and intimacy and I knew media well. We clicked right in. If I didn't give space in my schedule for that, then that successful journey wouldn't have happened. Those are my big 5. Yeah.”

Phoebe : “Wow! I've got to tell you, this episode really ... I hope Brand Journalism community, you go back and you listen to it again because sometimes things just don't sink in in the right way. A lot of great tips here. If you just listen to how he's lived his life, how Damon has created these things, become an entrepreneur, how he continues to think like a journalist and bring that to the entrepreneurial space, that's what's creating his success. Really, really valuable information. Now of course it is time to think like a journalist. This should be easy for you, Damon. You've been hired to help an ailing company. It's about to financially collapse. Its reputation is shot. You've got a month, a $1,000 budget, a smartphone and a laptop. How do you begin to turn this company around?”

Damon Brown: "All right. I'm going to come up with the hashtag #worstcompanyever or something to that effect. Then I'm going to put it into the hands of the public. It's like, ‘You guys are going to come up with our ad campaign.’ I might come up with an ad campaign that looks awful. Just the picture that I push onto Twitter and throughout this social media, whatever was popular at this time. I say, ‘You guys run with it.’ There's going to be memes. There's going to be social discussion. Most importantly, there will be talk about the brand. As we bring them into the car crash of our brand and we allow them to be part of it, they can also be part of that redemption when we come back later and have them help us become a better brand.”

Phoebe : "Man oh man! Love it! I've got to say I've done well over 300 episodes and I don't think anyone has ever quite come up with that. At least not that hashtag. Kudos to you. Good strategy. What is one piece of technology--video, multimedia equipment or an app that you just can't live without?”

Damon Brown: "Index cards, actually, believe it or not. I know you're asking about apps and technology. Through all the technology I love, it's index cards. I did a talk about it. I've written about it several times. I love index cards. They're nonjudgmental. You can carry them around. You can write things down wherever you are. You can bring them into the shower if you want, as long as they don't get wet. You can put little pieces of genius on there. There are great ideas that I've had ... At least I had great ideas, in my opinion, that I've had where I put them on an index card and I found them years later. I end up running with them. Some of them have become book ideas. Yeah, seriously. Some of them end up becoming app ideas that I'll probably end up doing in the future. I love the portability of it. Even as an app developer, that's something an app can't do for me. I love the old -school technology there.”

Phoebe : "Yeah. Right. Eventually. Maybe a good 10 years out, there will be floating index cards around us. How about a book, a documentary, blog, podcast or internet channel you'd like to recommend?”

Damon Brown: "Oh, I have a ton. I listen to a lot of podcasts, including yours. As far as books, my favorite is ‘The War of Art’ by Steven Pressfield. It's my go-to. What I love about the book is that it's a slim volume. It's probably 150 pages. I read it constantly. He's basically saying, ‘Your ability to create in this world ... Number 1, you already have a talent you need. The biggest problem is that you're not confident enough. You're allowing this thing called resistance to stop you from creating.’ All of that goes back to fear. The fear of not being good enough, the fear of being criticized, the fear of no one listening to you when you speak. It really talks about you getting over that fear. Every time I'm stuck, I go to that book.”

Phoebe : "So good. Expert predictions. The year is 2025. I'm curious, from your vantage point, both as a journalist and in the tech space as well as an entrepreneur, what do we have to look out for to be the best in our business and what will the world be shaped like by then? The merging of these 2 things in particular: journalism and business.”

Damon Brown: "Totally. I think that the platform is going to matter less and less. One personal example is that when I do a speaking engagement or when I'm a podcast, if you want to get meta about it, then it's shared on Twitter, on Facebook, on LinkedIn, on Instagram, which I'm getting a lot more into now, and other platforms. For someone like myself and for other people who have been journalists for a couple decades or longer, we have to realize that saying that our work is in The New York Times is going to matter a lot less. I would argue that it matters a lot less now. It'll be more about, again, your core. What are you saying? At a certain point, people aren't going to care whether it's read in The New York Times or read on Buzzfeed or read in a Snapchat story or what have you. No one is going to care. What they're going to care is the potency and the strength of the information and the authenticity of whatever you're trying to say.

"We need to focus on having an authentic voice, saying things that no one else can , saying them in a way that no one else will say, and then worry less about what platform they're going to be on because I see a future where platforms aren't going to matter as much. It's going to be more about our voice. We're at a particular period of time where, for many years, people have been saying that content isn't going to matter as much because people aren't reading as much and they're watching more and blah, blah, blah. I think it's actually the reverse, where the power of your content is going to have to be much higher because the platform is not going to hold you up anymore. The fact that I write regularly for Playboy isn't going to matter anymore. It's going to matter about what I'm actually saying.
"
"For the generation of my sons and other folks, it's going to be a world where they're just going to be focused on the authenticity and the information. That's it. I think as other journalists we have to focus on that versus trying to one -up each other as far as the platforms themselves.”

Phoebe : "Absolutely. That's a message directly to the brands, as well. Businesses need to understand that what they're turning out needs to make an impact and a difference. The same vein for them. Right?”

Damon Brown: "Oh, 100 percent. Even more so for them. Yes.”

Phoebe: “Excellent stuff, Damon. I loved everything that you’ve shared. Always great to talk to a fellow journalist, fellow entrepreneur. Thank you so much for all the valuable information that you’ve shared on The Brand Journalism Advantage Podcast.

Damon Brown: “Hey, thank you, Phoebe. Thanks for having me.”