Dave Conrey‘s path to becoming a full-time artist is not a simple one. Growing up, he wasn’t that passionate about art, but over time, and after a series of jobs and ventures, he has finally dedicated himself to the idea.

After going to school for art and graphic design, Dave had two separate stints as an art director, but was laid off both times. He also spent time as a author, podcaster, and creator of Fresh Rag, which helped artists sell their work.

After years of feeling unfulfilled, Dave finally decided to put everything else on hiatus to pursue his art full-time.

In this episode, Dave talks about the importance of connecting with others, some of his keys to building a creative business, and getting started.

Here are three things you can learn from Dave:

The Importance of Connecting with Others

One of the most important things we can do as artists and creatives is building a strong connection with other people. When Dave hosted the Fresh Rag show, people listened to it because his conversations felt deep and meaningful.

His conversations felt fresh and different because he didn’t try to force conversations with people just because they were famous. He just tried to build a report with his guests so they would have great conversations. “The most important factor for me is having a really good conversation, rather than just two people that might not know each other very well, talking about it, and the conversation is happening, but it’s kinda weird because there’s no real relationship built up. It’s just two people talking about it. And I want to have people that I know on so that we can have good conversations about it. And their experience level is less important to me than how charismatic they are in that conversation.”

The best way to build up to those great conversations is by building and fostering relationships with people. You are much more likely to have a great conversation with someone if there is a mutual trust and respect for each other. “It really comes down to having and building relationships with people over time. I mean, the people I’m going to have on the show are people that I’ve known, sometimes for a few months, and sometimes for years.”

The Keys to Building a Creative Business

Dave is a believer that there are a couple of keys to building your creative business. The first is building a brand that people love. The problem with branding is many creatives don’t know what their brand is. They believe good branding is just selling great products. But having a good product is not enough. “If you’re building up a brand that people love and adore, they follow you, not because of your product. I mean you make good products, that’s just important to make great products, but they’re not… on the edge of their seat waiting for your next Instagram post because your products are good. It’s because you are telling good stories and you… have good customer interaction and you have these relationships built.”

Another important factor for creative businesses is getting over your fears. Dave helped his audience get over their fears by having them participate in thirty day challenges. These challenges helped to change people’s mindsets from one of fear to one of action. “In my opinion, mindset is very important to how we do the things we do and so the idea was to create this thirty day challenge where you do a certain thing every day, or every single time you pick up a new challenge, whether it’s daily, weekly, or whatever. You pick up this challenge and do this thing, and it helps you kinda grow as an artist and grow as a maker. And whether its super actionable things you can do to… change your marketing program or it’s something you do in your head, getting outside of fear, the very first action is very fear based… fighting fear.”

The Perfect Moment Doesn’t Exist

One of the most easily overlooked, but incredibly important, aspects of creative work is just getting started. This may sound like an obvious suggestion, but often times we wait too long before taking action. We are so worried about failure that we instead of releasing something imperfect, we release nothing at all.

Dave believes we need to stop worrying so much and just get started. “Let’s say somebody wants to sell their photographic art prints… Figure out where you want to sell it and then just go put that stuff up there. Don’t worry about failing. Don’t worry about getting it wrong. Don’t worry about who’s going to see it because chances are nobody’s going to see it at first. Don’t worry about making sure you get your logo just so… don’t worry about any of that. Just get out there and post that thing up and then repeat the process, and then tweak as you go.”

Something that holds many creatives back, including myself, is the desire for perfection. But perfection is not only elusive, it’s impossible. You can’t wait for the stars to align because they never will. There is no better time than now. Remember, you can always start now and tweak later. “It’s less important for you to get it right and more important for you to get it out there and fix and tweak later because that makes all the difference. The ones that who take the action today, right now, are the ones who are going to win. The ones who are sitting back thinking ‘I don’t know. I’ll launch my show next month when I have everything just perfect,’ or ‘I’m going to buy that new microphone,’ or ‘I’m going to start my blog when I have enough money to get the really great theme that I need.’ Forget it man, just go.”

Shownotes

  • about Dave
    • worked as an Art Director at a magazine company and as marketing director at an art studio
    • had the choice of finding another job as art director or he could help creative entrepreneurs
  • creative background growing up
    • wasn’t passionate about it because it wasn’t fostered
    • he was encouraged and enjoyed doing it, but wasn’t passionate about it yet
    • in his 20’s he drifted towards art books/magazines
    • went back to school for art and graphic design
  • after school
    • got an internship at his professor’s studio
    • a lot of employers were impressed with his internship credentials
    • got job at boutique design studio for auto industry
      • worked his way up to art director
      • was laid off during the recession of early 2000’s
    • was in moment of transition, didn’t know if he would stay in graphic arts
      • didn’t have the tenacity to seek more work
      • worked his way through it through freelance and menial jobs
  • creating on his own
    • his site Fresh Rag already existed for a year
    • he enjoyed curating artists/designers but didn’t feel completely fulfilled
    • conversations about promotion/branding with co-worker convinced him to change direction
  • building his audience
    • interacted on Twitter
    • wrote his first book Selling Art Online
    • started his first podcast – biggest attractor of attention
      • many podcasts don’t have staying power
  • about his podcast
    • was attracted to the medium
    • has always been told he has a good voice and is a good conversationalist
    • enjoyed having conversations with people smarter than himself
      • digging deep on topics and having meaningful conversations
    • his conversation with Ashley Longshore
    • everyone doing interview podcasts
      • a lot of people went on the podcast circuit with the same set of people
    • changing what he did while still staying true to himself
      • the different stages of burnout
      • conversations got him thinking about the future
      • doing a different format or start something new?
    • re-listening to old episodes of your own show
    • learning from and fixing mistakes
    • Dave’s Maker’s Gonna Make Podcast
      • stories to help creative entrepreneurs
      • conversations about different topics with friends
    • expanding on newsletter topics instead of just links

28:37 “I always welcome conversation, or debate, or whatever. Lively debate is one of my favorite things… I try to put some sort of context into the world that we work and then hopefully start a conversation.”

  • creating conversations and connecting with people
    • tight group of people he wants to have conversations with
    • The Poster List – great at retail
    • Paige Poppe – hustler at a young age
    • connecting with people of all ages from all places
      • the context of the internet and building tribes
      • building a business through conversations and connections
    • Austin Kleon and scenius
    • getting the biggest names on your show
      • 9/10 times the conversations lacked
      • the relationship wasn’t there and it wasn’t comfortable
      • avoiding the mess and talking to people you like
      • entertaining first as a goal of podcasting
    • Aaron Draplin
    • proof of concept from his stories/voice and bringing in similar voices
      • creating moments for his community
      • helping someone with our conversation
      • serendipity
    • no one know what will and what won’t work, you can only find out through trying
    • being more prepared to make another shift
    • making shakeups (ex: The Tonight Show)
    • the evolution of comic book artists

29:33 “The most important factor for me is having a really good conversation, rather than just two people that might not know each other very well, talking about it, and the conversation is happening, but it’s kinda weird because there’s no real relationship built up. It’s just two people talking about it. And I want to have people that I know on so that we can have good conversations about it. And their experience level is less important to me than how charismatic they are in that conversation.”

30:34 “It really comes down to having and building relationships with people over time. I mean, the people I’m going to have on the show are people that I’ve known, sometimes for a few months, and sometimes for years.”

33:58 “Genius is something you posses and like a mindset or scope of your awareness, even if that means knowing who to reach out to for the right types of information… So using that concept and applying it to your scene, and that’s… our scenius. The people we hang out with in our scene.”

44:00 “I mean, that’s just the nature of the beast. We’re going to do things and we shouldn’t have to put these… ideas that we have to do something and it’s going to be that way, and it’s never going to change… ‘Because what happens if the fans don’t like it if I make this shift, that people don’t like it. What’s going to happen? People will hate me.’ That doesn’t work that way. People are just going to do something new if you quit or if you start something new, they’ll go over there or they won’t. But you’ll find new people. So, that’s the nature of the beast.”

44:51 “We’re creative people. I mean, name me one creative person that did the same thing forever, I mean the same exact thing forever, and if they did, they really weren’t that creative in my opinion.”

46:18 “Things are always going to change, even if it’s tiny little changes, there’s always going to be an evolution. Anybody who doesn’t change is just… not being very creative.”

47:51 “If you’re building up a brand that people love and adore, they follow you, not because of your product. I mean you make good products, that’s just important to make great products, but they’re not… on the edge of their seat waiting for your next Instagram post because your products are good. It’s because you are telling good stories and you… have good customer interaction and you have these relationships built.”

48:30 “In my opinion, mindset is very important to how we do the things we do and so the idea was to create this thirty day challenge where you do a certain thing every day, or every single time you pick up a new challenge, whether it’s daily, weekly, or whatever. You pick up this challenge and do this thing, and it helps you kinda grow as an artist and grow as a maker. And whether its super actionable things you can do to… change your marketing program or it’s something you do in your head, getting outside of fear, the very first action is very fear based… fighting fear.”

  • determining when to create his books
    • Selling Art Online started out as a week’s worth of list posts
      • series was so popular that he turned it into a book
    • Life After Christmas is least popular book
      • wasn’t chasing after something people were looking for
      • something people need don’t seek out
      • branding as a large topic to tackle
    • Creativity Badass Challenge started as newsletter challenge that became popular
    • Gold is in the List started by asking what his audience wanted to know about
      • people were asking about licensing and wholesale, but it wasn’t his specialty
    • books evolved because of their popularity, not because he was compelled to write them
  • designing his books
    • built and formatted his book but outsourced editing
    • sends to other people to read and get ideas
  • challenges people face
    • two mindsets – just in case and just in time learning
      • just in case – constantly consume
      • just in time – learn and do thing
      • few people fall into doer category
    • making sure people do something, not just listen to it
    • Gary Vaynerchuk
    • Michael Jordan quote on failure
      • MJ did not make his high school varsity team one year
      • Did it give him the drive to become better?
    • moments that shape people’s lives

55:10 “I would say the number one challenge anybody has, especially with any advice is that they don’t take action. There’s people that are advice addicts, right? Where they may read a book, and they like that book so much that then they read another book, then they read another book, and then maybe they take a course, then they go and buy somebody’s program, and then they buy another program. It’s just… they’re constantly building up all this information because it’s like ‘Oh, I’m getting so much better at all this learning, and all this stuff, yet they haven’t taken action on anything.”

56:42 “That’s the biggest thing, it’s just go learn something, even if it’s just reading a… chapter out of my book or a blog post that gives you very specific information about what to do, Go read that and apply it.”

58:23 “Nobody is undefeated… everybody gets beat at some point, and everybody’s going to lose at some point. You are going to lose at your business at some point. You are gonna fail. Your are gonna get beat up. You’re gonna get knocked out… The people that end up becoming champions are the ones that get back up and get back to it.”

  • advice for people starting their creative careers
    • starting is the best thing you can do
    • “Real artists ship.” – Steve Jobs
    • first step: just start
    • second step: start a newsletter list
    • social media as passive interactions
      • they aren’t really engaged
    • evolution of your work and what you’re working on
    • first gen iPhone
      • lack of functionality and being pushed by Android
    • do things now and fix them later

1:00:41 “Let’s say somebody wants to sell their photographic art prints… Figure out where you want to sell it and then just go put that stuff up there. Don’t worry about failing. Don’t worry about getting it wrong. Don’t worry about who’s going to see it because chances are nobody’s going to see it at first. Don’t worry about making sure you get your logo just so… don’t worry about any of that. Just get out there and post that thing up and then repeat the process, and then tweak as you go.”

1:01:33 “It’s less important for you to get it right and more important for you to get it out there and fix and tweak later because that makes all the difference. The ones that who take the action today, right now, are the ones who are going to win. The ones who are sitting back thinking ‘I don’t know. I’ll launch my show next month when I have everything just perfect,’ or ‘I’m going to buy that new microphone,’ or ‘I’m going to start my blog when I have enough money to get the really great theme that I need.’ Forget it man, just go.”

1:02:42 “If you start a newsletter and you get people on that newsletter and they’re interested in what it is you’re doing, if they’re signing up for your newsletter, then they’re at least saying to you ‘I’m interested to know what you’re about.’… They’re engaged in that and you have them. They’re captive. You have those people that you can reach out to anytime you want. They’ve given you their permission to say ‘Send me an email when you have something to say.’ So… start and start an email list.”

1:04:20 “Apple is like, they go and they launch before they’re really ready, I mean, before it’s perfect, they go and they launch because they want to find out. They want the data to find out ‘How are people interacting with this thing that we’re creating?’ rather than just saying ‘I’m going to try and make up the product, the best I possibly can for everybody,’ and then launch that ten years down the road. I’m going to launch the minimum viable product, see how people interact with it, and then adjust. Pivot. Pivot on that.”

  • plans for the future
    • focusing on what he’s doing now
    • working on his art
  • favorite quote
    • “A tiger doesn’t lose sleep over the opinion of sheep.” ― Shahir Zag
    • people telling him how to do his show

1:08:00 “A winner doesn’t care what everyone else is talking about. It’s still going to go out there and hunt.”

1:08:51 “If this is going to be mine, then it has to be 100% for me… Of course there is something to be said for taking in information that might be valuable… constructive criticism is good. But at the end of the day, very often I would tell people, ‘Hey do me a favor. Tell me what you think. I’m not necessarily going to listen to you, but tell me what you think.’ I tell them that all the time because it’s important to maintain who I am and I’m still going to push forward on what I believe is right, and you’re not going to get in my way.”

  • morning routine
    • five year old dictates his routine
    • sets aside time each morning for himself
    • 100 day challenge – sitting with notebook and sketching something
      • sketches first thing he thinks of
      • absorbing himself in something creative and meditative to set the day
    • putting your dreams onto paper
    • Dream:On app (no longer being worked on)
  • recommendations
    • PopFashion podcast
      • 2 women with great report and the inspiration for his show
      • lessons you can learn even if you aren’t into fashion
    • Ask GaryVee
      • lessons on business and an honest perspective
    • Start and Quitter by Jon Acuff
    • Big Magic by Elizabeth Gilbert
    • #AskGaryVee by Gary Vaynerchuk
    • Mind of a Chef , Chef’s Table,  Cooked
      • perspective of chefs and how they turn their work into art
      • creative world we don’t think of as creative
      • lessons you can take from cooking and apply to another industry
  • creative people
  • definition of creativity

1:22:53 “Creativity to define that is being open to exploring new ways of thinking about the things that you do. So whether that’s graphic arts, arts, crafts, web design, mechanical engineering, whatever… looking at things differently, and taking at that thing you look at, say you’re a cook or a chef, and you want to make a cheese sandwich. How can you deconstruct that or make it different, rather than just changing the cheese or putting a tomato in there, or whatever. What can you do that’s different? What can you do that’s out of the norm or completely radical? That might not make a cheese sandwich anymore, but your interpretation of that cheese sandwich. That’s the definition of creativity, to be willing and open to the possibility of a new way of thinking.”

  • how to be more creative
    • creativity is a muscle
    • you are going to suck when you first do something, you get better as you go
    • evolution of people’s drawings on Instagram
    • Maya Angelou quote on creativity

“To get more creative, you have to practice. You have to practice thinking outside that box. You have to practice thinking about things differently. You have to practice looking at things from the right instead of the left.”

  • challenge
    • if you’re thinking about doing something, stop thinking
    • take action today
    • buy that domain, research something on Youtube, etc.
    • the action you do today leads to further action
    • superstars are becoming less common because anyone can put out content
      • the amount of content will go wider
    • be a shining light to someone

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