About this episode

Creative geniuses are wired differently than the rest of us. Though many of the guests on the show readily do so, most creatives don’t even see themselves as entrepreneurs. This can cause a crisis in identity. I want to bring authenticity and transparency to the entrepreneurial journey so you have a complete picture of how nonlinear it truly is. That is why I brought Jeff Rogers on to tell his startup story.

Jeff Rogers is the founder of Howdy Jeff, a creative agency that focuses on typographical illustrations. He demonstrates how incredibly diverse entrepreneurship really is. Tune in to hear how he journeyed from playing drums in Texas honky-tonks to creating some of the most remarkable typographical illustrations for global brands.

In this episode, you'll hear:

  • How his dad’s entrepreneurial journey and work ethic shaped Jeff’s future.
  • When he started to realize he didn’t want to be in the music industry forever.
  • How he got into the graphic design scene.
  • The value of humility and being teachable.
  • What his brand is known for.
  • The challenges he’s encountered in working for himself.
  • The importance of pushing ourselves to be the best we can be as entrepreneurs.
  • The first steps Jeff would take if he was starting now.
  • How Jeff has wrestled with the notion of being an entrepreneur and a creative.

Resources from this episode

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The Startup Story Inner Circle: https://www.thestartupstory.co/vip

Jeff’s website: https://howdyjeff.com/
Jeff on LinkedIn: https://www.linkedin.com/in/frogers/

The Startup Story on LinkedIn: https://www.linkedin.com/company/thestartupstory
The Startup Story is now on YouTube: https://www.youtube.com/jamesmckinney
The Startup Story on Instagram: https://www.instagram.com/thestartupstory

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EPISODE CREDITS

If you like this podcast and are thinking of creating your own, consider talking to my producer, Danny Ozment.

He helps thought leaders, influencers, executives, HR professionals, recruiters, lawyers, realtors, bloggers, and authors create, launch, and produce podcasts that grow their business and impact the world.

Contact him today at https://emeraldcitypro.com/startupstory

Episode transcript

The Startup Story - Jeff Rogers

Jeff Rogers: Hi, this is Jeff Rogers. I'm the founder of Howdy Jeff, and this is MY startup story.

Every wildfire began with a spark. Every superhero has an origin story. And every single startup has a moment that they point to as their beginning. And every founder has a purpose that drove them in the midst of all obstacles. THAT is The Startup Story.

[00:27]
James McKinney: Welcome to another episode of The Startup Story. If you're new to The Startup Story podcast there is a way you can advertise your business for absolutely free. Yes, you can advertise your brand, URL, or any simple call to action for completely free. All you have to do is leave a five star rating and a written review in Apple Podcast and if you do that I will read your review in an upcoming episode for my entire audience to hear. So make sure to plug your brand, URL, or social media account in that review. These episodes live on forever and so will your ad. Again, I'm giving you a free advertisement for just writing a review on Apple Podcast as a way of saying thank you for taking the time to write a review.

With that in mind, thank you to Rule who gave The Startup Story a five star rating and wrote, "I was searching for information on someone and found that they had an interview on this podcast. I was so delighted with the interview. The length is perfect for a morning walk or commute. The length also enables a better and deeper conversation. I was so engaged that I subscribed and found the next episode equally fascinating. This is now my new go to podcast for inspiration, motivation, and education." Well, thank you Rule for the great review. I truly do appreciate it. And again, a reminder for everyone, if you want to give your brand, URL, or social media account in the written review that is just some additional visibility you will get when I read your review in the podcast episode. These mini ads live on for years to come, so if you want a chance to highlight your business, startup, URL, social media account, whatever the case may be, then just visit Apple Podcast today and leave your written review. All right. Now let's jump into this week's episode.

Our guest this week is Jeff Rogers, founder of Howdy Jeff, a creative agency that focuses on typographical illustrations. I'm just going to put it out there right now, his work is incredible so make sure to visit howdyjeff.com once you're done listening to this episode. This episode marks the 91st episode of The Startup Story and just my second interview with a purely creative entrepreneur. In fact, the last interview I had with a creative or artisan was episode eight when I interviewed Brandon Monk Munoz of Monkwood Studios. His woodworking is inspiring. Now, I tee all that up because I believe those who are wired with creative genius are just wired differently than most of us, and for that reason I find that most creatives truly do not see themselves as entrepreneurs. We actually talk about that crisis in identity within this episode. Entrepreneurship is so incredibly diverse and The Startup Story wants to tell all of those stories, or as many as possible.

I want to bring authenticity and transparency to the entrepreneur journey so that you would have a complete picture of how nonlinear this journey truly is. I want to share stories that will resonate with you regardless of the industry our founder operates in. That is why we've extended our story telling to video with a new initiative titled The Startup Story Presents. Thanks to my partnership with the Think Branded Media Team, we will be releasing featurettes on select episodes via Entrepreneur.com so you can see a different layer to my guest's startup story. We will also be including a video on the episode page where we create these featurettes. In fact, Jeff's episode today right now is one of those episodes. You can see his featurette at thestartupstory.co/thedesigner. I know you're going to love this episode and all the value that Jeff Rogers is going to bring to us as we explore how he journeyed from playing drums in Texas honky-tonks to some of the most remarkable typographical illustrations for global brands. But just like every story we need to start at the very beginning.

[04:06]
Jeff Rogers: My dad was an entrepreneur. He wasn't at first. He was a very gifted artist, but he was raised super conservative. His parents were just ultra conservative and never really supported him to be an artist. So I learned how to draw from him, but he went to school for business and then he got into real estate and he hated it. So he tried to figure out something else to do which was run a bakery.

[04:35]
James McKinney: Okay. All right.

[04:37]
Jeff Rogers: And so he knew, not that he's super passionate about baking but that it was something that he felt like he knew someone, a good friend who owned a bakery, and he said, "Hey, can you teach me how to do this? I need to do something." He's like, "It'll be great, yeah." So he trained under him for a few months in 1988 and opened his own bakery, and owned it for 26 years.

[05:00]
James McKinney: Wow.

[05:01]
Jeff Rogers: And made a great living, gave us a great life. That has always been part of my story, seeing how he was successful and he worked his ass off. He got up at 4 am every morning and he did that for us, and he did it. At one point, he opened a second bakery and it was just an abysmal failure. They had to file for bankruptcy but eventually he was able to sell the bakery and kind of do something else after his elbows couldn't take it anymore.

[05:30]
James McKinney: Yeah, I bet. Now so when you think of your childhood, how old were you when he started the bakery? Do you look at dad the baker? Do you look at him as the real estate guy, the artist? What do you view your childhood years, what was he doing?

[05:42]
Jeff Rogers: I was about nine years old when he opened the bakery and made that transition, and I saw how difficult it was.

[05:50]
James McKinney: Why did he make that transition?

[05:52]
Jeff Rogers: He wanted to be in control of his life.

[05:56]
James McKinney: Do you remember a conversation? And I keep poking at that because in all of our stories, I mean to be honest I can't think of my almost 100 interviews, I can't think of a single one that came out the gate, "I'm building my own empire." There's always some shift that takes place in our story. Being that I also believe that was modeled for you I want to keep peeling this. What caused the shift for him?

[06:26]
Jeff Rogers: I think it was just frustration from having a couple of just bad bosses. I don't think he ever felt like he could grow or really make an impact in the business that he was in working for people who didn't care about him, and so he was fed up.

[06:49]
James McKinney: And how old were you when this shift took place?

[06:50]
Jeff Rogers: About eight or nine.

[06:52]
James McKinney: Eight or nine, okay. So relatively young, probably oblivious to some of the challenges that were taking place.

[06:56]
Jeff Rogers: Totally oblivious. We were having the best time.

[06:58]
James McKinney: Exactly. Like my dad brings home sweet treats.

[07:00]
Jeff Rogers: We're good, we're good.

[07:02]
James McKinney: So as we continue on in your story though, we're coming into high school and high school, especially the end of high school, that's the end of a natural chapter for us. What did you think you wanted to do?

[07:15]
Jeff Rogers: I didn't want to run a bakery, because me and my brothers worked at the bakery a lot and that was also very helpful to see him first hand, what he was doing every day. A lot of people don't even know what their dads do. I knew exactly what my dad did.

[07:31]
James McKinney: And you got to see how hard that business is.

[07:32]
Jeff Rogers: Yeah.

[07:34]
James McKinney: So that's awesome.

[07:35]
Jeff Rogers: And we had, on Christmas Day or whatever or Christmas Eve day we'd show up at 5 a.m. looking all tired and he's like, "Hey, stop looking tired, it's time to work. Don't look tired. I've been here for four hours already." We're like, "Okay, okay." He's just like, "Do your work."

[07:56]
James McKinney: I love it, I love it.

[07:57]
Jeff Rogers: It's awesome.

[07:58]
James McKinney: That is awesome. That's a work ethic you don't see a lot these days and you don't see parents pressing that hard these days.

[08:02]
Jeff Rogers: Yeah, yeah.

[08:03]
James McKinney: That's a whole other podcast. I could talk about that to the enth degree.

[08:05]
Jeff Rogers: Oh totally.

[08:07]
James McKinney: So again, you saw the work ethic. You worked in the bakery. Coming to the end of high school you realized you didn't want to be a baker. What did you think you wanted to be?

[08:15]
Jeff Rogers: I always knew I wanted to do a job that was fulfilling. I think in articulating it or saying it like that now, when I was in high school it was I don't want to sit at a desk and I want to do something that's fun for my job. I want to do something that makes me happy.

[08:34]
James McKinney: But you say fun though. What was… fun for a high schooler is so different than fun for maybe you and I now. So when you think of a job out of high school, because we all thought of something, what was that thing?

[08:49]
Jeff Rogers: Specifically in high school I wanted to be a musician. I had always been interested in art and I knew I was always going to do that. But when I got really deep into music and I happened to have a couple of incredible teachers going into college, I was going to be a music major and I was going to be a musician, because that's what was super fulfilling and fun. That shifted obviously, but in high school that's where my head was at.

[09:18]
James McKinney: And so as you're wanting to pursue that as you're entering into college, what did your dad say about that? Because his story is actually a story of having a passion for something, not pursuing it, and then coming back to something he did enjoy with some challenges of course. But so where was he at with you wanting to do that?

[09:40]
Jeff Rogers: His response to his parents not… and they were great and everything, but they didn't really support him. His response to that was he was going to just support me and my brothers no matter what we wanted to do.

[09:51]
James McKinney: That's awesome.

[09:52]
Jeff Rogers: As long as we worked hard, and he wasn't going to let us just try a bunch of stuff and quit. But if we were really into it, he was like go for it, do it. I was like, "I want to be a musician." He was just like, "Great, do it. Where are you going to go to school? Let's go." I was like, "I want to go to UNT. It's the best music school." He's like, "Great."

[10:11]
James McKinney: So you go to college, you go to University of North Texas, a good music program there. While you're there, obviously heavy music courses. Are you still thinking through your four years, did it take you four years to graduate, how long was yours?

[10:24]
Jeff Rogers: Five.

[10:25]
James McKinney: Five years, so through your five year journey did you end your college thinking I'm still going to be a musician?

[10:32]
Jeff Rogers: No.

[10:33]
James McKinney: So what happened in the four years you started realizing that wasn't the story to play out?

[10:37]
Jeff Rogers: Well it was pretty quick when I realized that my whole big dream of in music at that point was to be, I was a drummer, wanted to be in the drum line at UNT, and I made the drum line my freshman year and I did it. I was like, "Whelp, I did the thing I wanted to do." There's really literally nowhere else to go unless… so I started playing more drum set. But then I really looking at it, to make a living I'm going to have to be a band director or I can be a session musician or a touring musician. I'm like shoot, I'm going to have to rely on this passion to make money and I'm going to have to do a lot of stuff that I don't really want to do in music.

I figured out with music I want to always just do exactly what I want to do with music, and play in the bands that I want to play in, and maybe that's not the… so I switched back to art as a career path or whatever. I was like I'll always want to play music and I always have. That's a huge part of my story is what music taught me about graphic design and art making, but yeah had that shift. I changed my major a few times. It was like communication arts, and then 2D studio, I'll be a painter. Then nope, I would be poor. I can paint, all that's learned in college, let's learn something I don't know how to do. So I'll learn the computer, and then that's when it shifted to graphic design. That's when I discovered what that was I think my junior year or something.

[12:08]
James McKinney: So if you were to think back to your college years, again I'm all about these decision points in life. There's just so many of them, and some are natural decision points. End of high school, end of college, marriage, kids, there's natural decision points but there's some that are subtle. But again end of college being an organic one, what did you want to do with that degree coming out of college? What would the 23 year old Jeff say what you're going to do with this degree?

[12:38]
Jeff Rogers: When I graduated from college, I kind of had just started learning about graphic design. I had a graphic design degree but I'd only spent less than two years digging into it, so I was still very green. My thought was I'll find a job at a really awesome design agency and just keep getting better, and I'll like rule the world. But what actually happened was I just went on tour with a band for a year after I graduated with my graphic design degree.

[13:10]
James McKinney: That's awesome.

[13:12]
Jeff Rogers: And I'm really glad I did that. It was a crazy… it was a wild year.

[13:17]
James McKinney: So let's put some time stamps on things. So what year is this right now? What year are you on tour?

[13:20]
Jeff Rogers: That was 2001.

[13:22]
James McKinney: 2001 you're on tour, and let's not also overinflate or understate how significant it was. How big was this tour? A year on tour, across the US?

[13:32]
Jeff Rogers: It was Texas. It was weird because I didn't really like the music. It was a Texas country band and a lot of people, if you're a fan of country music or Texas country, his name is Aaron Watson. He's pretty huge now. Not so much when I was in the band but he is a business man and he's going to make it. I was like he's going to be huge one day. And that was I lived in Dallas with my roommate who played bass in the band, somebody I'd played music with for years decided to go, and I said, "I'll only do it if Dylan comes too," because we were like not into the music. So we'd go to these honky-tonks and stuff, just like standing in the corner, just observing like, "These people are so crazy." But it was mainly-

[14:18]
James McKinney: it's like playing at the zoo every time, like look at these species in here.

[14:21]
Jeff Rogers: It's literally. One time there was an entire family down in Bryan, Texas there was a whole family with mullets. The kids, the mom, the dad, everybody had the exact mullet haircut.

[14:32]
James McKinney: That's awesome. It's almost like the People of Walmart Instagram.

[14:36]
Jeff Rogers: Oh man. But it was wild. A couple places with chicken wire across the front of the stage and that kind of thing. We would be in Dallas for Monday, Tuesday. Then we'd drive, we were based out of Abilene, Texas so the rest of the band was there so we'd drive to Abilene, and then do like a four day tour playing in Amarillo and come back down, or going down to Houston, or going to Louisiana or something. Each week was like a little mini tour so we did that for like a year. So we were never gone for months at a time because we rode around in a Ford Excursion. He's got like three buses now, so thanks a lot.

[15:14]
James McKinney: Drastically different, right?

[15:15]
Jeff Rogers: Yeah.

[15:16]
James McKinney: Drastically different. So at the end of that though, for the musicians that are listening or those that had musician dreams before their current business, that sounds like a dream come true.

[15:28]
Jeff Rogers: Yeah.

[15:29]
James McKinney: That sounds like you got paid to do what you wanted to do. Now granted, you had shifted and you were a designer, but did it that come to an end because the tour came to an end, because you were done, time to go do something different? Why did you stop doing that and then what was your first design gig? Because now you're a year, not only are you only two years' experience in graphic design you had a one year break, so how did you get back into the scene?

[15:54]
Jeff Rogers: So I was kind of getting tired of eating Wendy's dollar menu. I made a living but it was not much. And at that point in Aaron's career where we were a solid band, and he positioned himself to open for these huge acts for like hardly any money so we played in front of these huge audiences and the exposure was crazy, but no hotel. We were schlepping it.

[16:22]
James McKinney: When you say huge audiences and big names, who were you opening for?

[16:27]
Jeff Rogers: We opened for people like Pat Green, Joe Nicholls, Cooder Graw, Houston Rodeo in front of 5,000 people.

[16:33]
James McKinney: So very, very niche audience though. I don't know any of those names as I'm sure-

[16:37]
Jeff Rogers: I wouldn't have either.

[16:38]
James McKinney: Yeah, okay.

[16:40]
Jeff Rogers: But Texas people like they definitely do.

[16:42]
James McKinney: Yeah, they knew. Okay.

[16:43]
Jeff Rogers: So it was big audiences and that eventually did it for him. As an entrepreneur himself, he's got a pretty amazing story. But I wanted to marry my girlfriend. I was like I've got to make some money eventually so let's stop this and try to go use my degree and get my first design job. Which ended up being at SBC which is now AT&T. My now father-in-law's cousin ran a certain department within the company called the proposal center. I got a job making covers for proposals that, and I was there for three and a half years. I would literally design a cover, print it out, and put it in the plastic sleeve of a three-ring binder, and that was my job.

[17:35]
James McKinney: Okay. I just want to pause on that for a moment because as I think of big corporations, it blows my mind away all the roles that are created within that.

[17:50]
Jeff Rogers: I know.

[17:51]
James McKinney: I mean now looking back you're probably thinking to yourself that was not even necessary.

[17:54]
Jeff Rogers: Like what, I know. Didn't need it. Was not necessary.

[17:57]
James McKinney: Of course, digital proposal, forget the technology side of it, just the head count side of it, it's like that is the role, wow.

[18:06]
Jeff Rogers: It was weird. I learned a lot of valuable things there but I also when I was in the band I was taking every opportunity to make merch, do all the t-shirts and do whatever I could design wise to keep practicing. Not that I always felt like I was practicing, just because I wanted to. I was like oo, let's make t-shirts to do the merch. I was still doing design.

[18:30]
James McKinney: Was there any part of you that was just disappointed with that SBC/AT&T job coming off of the creative year that you had of playing in a band, being on tour, creating merch and obviously I'm assuming the designs were creative in nature, and really what you wanted to now doing proposal covers. Was there a level of disappointment that you had to wrestle with at all?

[18:51]
Jeff Rogers: No, I was super pumped.

[18:53]
James McKinney: Really? Why?

[18:54]
Jeff Rogers: I was so excited because it was my first real job doing graphic design. Then that's all that I cared about at that point. I was like I have this job, I'm getting paid a lot of money and I can get better and I can improve, and I'm here.

[19:10]
James McKinney: That's awesome.

[19:11]
Jeff Rogers: And then eventually they were like, "We need some more people to do this." I'm like, "Okay," and so I hired like three of my friends so we were just hanging out, making this very low stress job, but I got pretty frustrated pretty quick because I didn't have a mentor. I was quickly promoted to the head of that department which was like 12 designers all across the country who were all like in the forties, and now I'm this kid who's their boss and they were all disgruntled, and it ended up being kind of weird.

[19:41]
James McKinney: Let's talk about that being frustrating. Why were you frustrated, because you didn't have a mentor?

[19:45]
Jeff Rogers: Yeah. I felt like my work was not improving. I felt like I was really, really stuck, like I wasn't able to do anything. And at that point I had this idea that I needed a good job to be a good designer, which I know now is not true at all. So I got into this like death spiral of if I can't find a good job I'll never be a good designer, but who is going to hire me if I can't become better? If I can't get better, then I'm not going to get a good job, how do I get out of this thing? That was like a year and a half, and I was just totally not motivated anymore. I just felt tired, didn't care about anything just because it was so exhausting mentally to be frustrated at work and not knowing how to change anything.

Oh, and the other misconception I had was if I go and show my work to somebody it's got to be good. It's got to be really good before I can show it to somebody, but that's not good and I know it's not good, I don't know how to make it better. So I eventually was like screw it, I have to talk to people about my work and ask them how to make it better. So I just started like the people around Dallas who I thought were the best creative directors, the best agencies, I started calling people, "Can I come show you my work so you can tell me why it sucks?"

[21:07]
James McKinney: I love it, oh I love that though.

[21:08]
Jeff Rogers: And it felt horrible. It felt like I was totally exposing myself. It was uncomfortable.

[21:14]
James McKinney: Well I mean that is a very humbling and vulnerable position to be in.

[21:17]
Jeff Rogers: Very.

[21:18]
James McKinney: But I will say I commend that you had the foresight and willingness to do it, because while I think the idea that you had to work with a better firm to become a better designer or something to that effect, while I don't necessarily agree with that, the fact that you saw the need that there has to be something that continues to grow you as a designer to be better, I love that.

[21:41]
Jeff Rogers: Yeah, yeah.

[21:42]
James McKinney: Absolutely love it.

[21:43]
Jeff Rogers: After I started talking to people, there's some smart people out there and almost every single person that I contact said, "Yeah, come on in. happy to check it out." And what I found was most of the people were like, "This is good. You could work on this and maybe change this, but it's cool." And I'm like, "I don't know." I was just desperate. I was desperate to get better and so even though it was really uncomfortable, what I learned from that was at the end of a meeting I'd be like, "Is there anyone that you know that might be a good person to talk to?" They're like," Oh Bob at what's-his- name or whatever at this agency would be great." And I'm like, "Oh, great." And then I'd email that person and say, "Hey Jeremy over here said that you'd be a good person to talk to." Like, "Oh, I haven't talked to that guy…"

And then it was like this connection and I was like is this what networking is? This is networking! So advice I give to younger designers all the time is like don't call people looking for a job. Call people because you want to get better and you want their advice, because that will ultimately show them… but you have to be honest with yourself too about that and not be manipulative or something. You have to first want to improve and take criticism and work with the criticism, then keep in touch with people because then they will see that you're serious and you have enthusiasm, and you can work with criticism. I always say like can I work on this and who you and see what you think? They're like, "Yeah, yeah, yeah."

[23:24]
James McKinney: See, this is what I love. So again for those listening, I hope you are seeing the value in just this key takeaway. If there's anything you got out of Jeff's story, this takeaway could carry you for so long. Just the idea, and this is where people get hung up right. We have this idea that we have to be the experts at what we're doing, therefore that means that we can't ask for insight and guidance for others. One, absolutely false, completely bogus.

[23:49]
Jeff Rogers: Totally false.

[23:50]
James McKinney: it is a limiting belief. It really boxes you in and look at from that decision point you had where you met with other designers just to get input, how many no's did you get as you reached out to people?

[24:04]
Jeff Rogers: None.

[24:05]
James McKinney: Good.

[24:06]
Jeff Rogers: None. I would get silence or yes.

[24:09]
James McKinney: Yeah, and silence I mean you know, look-

[24:11]
Jeff Rogers: It's like you're busy. People are busy.

[24:13]
James McKinney: Exactly. Silence is completely different than a flat out no.

[24:15]
Jeff Rogers: Yeah.

[24:16]
James McKinney: Right. But you had a ton of yeses. I inherently believe, now granted there's a bunch of tools out there, let's just be very clear about that, but I inherently believe people want to help and if you come to me or you go to anyone with sincerity asking for guidance, help, direction, whatever, I don't have a statistic for it but I have to believe eight out of ten times, it's going to be a yes. What you also did that I love, that I hope everyone picked up on, was that secondary referral, that connection. And again, what year was all this taking place in?

[24:48]
Jeff Rogers: This was probably 2004-ish, 2005.

[24:53]
James McKinney: 2004 right so LinkedIn wasn't around yet. 2004 again yes, I love that you discovered networking. I love every bit of it. But it's like all those things people have forgotten because of the ease and simplicity of LinkedIn. It's like, "Hey can you make an introduction?" And you do a connection request and it stops there. It's like that's not a relationship, that's just a connection online. So I love all those things.

And again as an entrepreneur all of this stuff is applicable too because if you're a fitness owner and you were going through COVID, there are fitness owners that have succeeded massively in this season of life, and if you're struggling, if you were to reach out to them I can assure you they're going to want to help. I've had people reach out to me just for guidance, whether it be podcast related or startup related or investment capital related. I will, and maybe four weeks before we get a call but I'm going to try and fit as many as possible. People want to help inherently. At the same time I have to ask, if people reach out to you are you willing to help?

[25:55]
Jeff Rogers: Absolutely.

[25:56]
James McKinney: That's the thing, it continues to go.

[25:58]
Jeff Rogers: Yeah. I feel like it's my duty.

[26:00]
James McKinney: Yes!

[26:01]
Jeff Rogers: I mean for the people that helped me and how huge it was for me, just the conversations, anytime anyone emails me, wants to talk, I every time will talk to them. I'll sit there and write an email back. What's frustrating is 80% of the time no response back, nothing. But that is like every time that happens I've put people on the spot before like, "Hey also, somebody takes some time to help you, say thank you."

[26:29]
James McKinney: Yes.

[26:30]
Jeff Rogers: You know? That's going to help. They're like, "Oh, oh, I got busy." I'm like, "I guarantee you I'm busier than you. I'm much busier than you."

[26:38]
James McKinney: And I think that ties back to the sincerity. If all you're looking to do is to consumer someone's time to get input, just don't be a tool. Just don't even do it. But if you truly value the person's insight and advice they're going to give you, then show that value after the fact through gratitude. So you meet all these people, you make these great connections. I assume you start, and I'm going to say the word encourage but not the way the world thinks of it as like oh, such kind words, but literally courage being placed inside of you. You started increasing in your own personal belief at how good a designer you were. So as that belief started to increase, when did we get to you doing your own thing?

[27:16]
Jeff Rogers: Right. Well in meeting some of those people, there are little sound bites that I still have carried me to this point. There's an art director, Paul Jerty, and he took the time to talk to me and I was doing my big complaining thing about, "How do I get a good job if I don't have work?" And he just looked at me, he's like, "Just do the work that you want to do, and eventually somebody will pay you to do it." I just thought that was ridiculous. I was like you clearly don't know my plight, you don't understand, you're already successful and everything.

But it wasn't until later and I was just absorbing everything that I could, just trying to figure out… I was fully motivated to like move. That phrase really clicked when I understood what he meant was you've got to do the work that you want to do, which for me it meant oh I have time at night, I have time on the weekends. Yes, you're going to have to make a living, you're going to have to have a job, but you are in control of all that other time and you have all the control in the world as far as how you want to use that time, what projects you want to do, what you want to try and get out there, and how you do it. It was like this a-ha, like I don't need a good job to get better. I fully can own that myself, that's my job.

[28:38]
James McKinney: That's incredible. That's so powerful as well. It's funny, the moment you said that, one when you mentioned the quote I didn't go there at all with it. I was like oh, I'm curious how this is going to unpack itself.

[28:52]
Jeff Rogers: Yeah, because it sounded crazy.

[28:54]
James McKinney: but then as you start talking about those extra hours, I immediately went back to this was probably 2005, I was an employee. I was an accounting manager of all things. I had a team of accounting assistants and there was one employee who was spectacular at just data entry. She was so incredible at it, so fast at it, so quiet, so diligent. But she was an amazing artist. I remember asking the question, "Why don't you try and do this fulltime, try to sell your stuff?" She's like for her, then it won't be fun. Like I come here to do braindead stuff so that I can do creative stuff later.

[29:31]
Jeff Rogers: And that's what music was for me, that's exactly the thing… that's what music was. I'll do music on my own when it's the most fun. Because if it's a job, it won't be fun.

[29:40]
James McKinney: I love it. So you start honing your craft in the afterhours if you will?

[29:44]
Jeff Rogers: Yep, yep, and just asking everyone. My wife, I got married and my wife's an actor so if she was doing a show, I'd be like, "You need a theater poster? You need a poster for the show? I'll do it."

[29:54]
James McKinney: That's awesome.

[29:55]
Jeff Rogers: "You don't have to use it, but I get to do whatever I want, no revisions." You know, but I'll do it for free. So I started doing that, playing with a lot of bands still, doing a little records and live recordings. I'd make CD packaging for all that stuff and just I was really having fun doing that. And as my stuff was getting better I was still getting out there and talking to people. And then my wife, who has a similar story as me as an artist, we were at dinner and she just like, we were just talking about we want to do something with our lives. We have to do something crazy. And so she slammed her hands down, she's like, "Let's move to New York."

[30:33]
James McKinney: Whoa.

[30:34]
Jeff Rogers: I was like, okay. And she had tears in her eyes, she was like intense like, "We have to do it!" I was like, "Let's do it! Next year, let's move to New York. Let's save up," so it was like two years. And during that time I got better and better jobs. The next job I got was a web design studio which I learned that I don't want to make websites. Left there and then got a job at a cool little boutique studio. I could talk for hours about each one of these little steps, about quitting my first job and how you know-

[31:09]
James McKinney: How liberating it was?

[31:10]
Jeff Rogers: Yeah, and how scary but then it's like oh it's fine.

[31:12]
James McKinney: But all those little steps though, and again for the sake of time we won't go through every little step but looking back though before we jump into your venture, do you see each of those as an actual step up and forward? How do you view those seasons of life leading you to where you are today?

[31:33]
Jeff Rogers: They were definitely if you're thinking about staircase, there's just steps up for sure. I was walking on the ground at AT&T, and then once I started moving I was taking little steps up. Each person I talked to, every time I spent on something and did another project, sometimes what I was working on sucked and didn't work but I learned something. Then I really got to where I loved learning and being in a position where I was the dumbest person in the room basically, because then I knew I could learn the most and I put the uncomfortable part of that aside knowing that the payoff would be huge.

[32:15]
James McKinney: That's awesome.

[32:16]
Jeff Rogers: Like I can do some discomfort. So that's why moving to New York was like yes, that's terrifying, let's do it. When we moved to New York we drove up in our car, just full of all our stuff and got this teeny, tiny little 300 square ft. apartment.

[32:33]
James McKinney: New York living.

[32:34]
Jeff Rogers: Yeah dude. And we were so excited. It was like the thing that you asked about SBC like were you kind of bummed, and I was like no, no, it was great. Looking back it was like ugh, it was awful. But at the time you're like this is awesome. We don't have a job. Let's do it.

[32:51]
James McKinney: I love it.

[32:52]
Jeff Rogers: So I don't even have an iPhone at this point so I was like trying to-

[32:55]
James McKinney: What year was this?

[32:56]
Jeff Rogers: This was 2008.

[32:58]
James McKinney: Okay, no iPhone yet.

[32:59]
Jeff Rogers: Yeah, so I was like trying to figure out the subway and… but I just went for it. Just like I had practiced doing here, I went and … Oh, the other cool thing that I didn't say was as we were about to move to New York all these connections that I had made around town I got two job offers right before we moved from incredible agencies, because they needed someone. I was around, they knew me, I had a face. I always tell people if you have a face people will be more likely to want to-

[33:28]
James McKinney: 100%.

[33:29]
Jeff Rogers: Yeah. Go talk to people, meet with people in person.

[33:34]
James McKinney: And you've already proven yourself as teachable, that's the thing. Again, we could spend a whole podcast on just the value of humility, being teachable, networking. It's so powerful and I think people, they have shelved the value of what that brings.

[33:53]
Jeff Rogers: Yeah, because now it's all about I have to put myself out there as the expert, as the best version of myself but you're right, you lose so many opportunities to become better at what you do when you're like I'm the best, I'm the best, I'm the best. It's sad.

[34:09]
James McKinney: It is. It really is. It's a one dimensional life.

[34:14]
Jeff Rogers: Like you don't have to always be the best.

[34:15]
James McKinney: 100% there's so much to be learned from other people, it's unbelievable.

[34:20]
Jeff Rogers: it's incredible.

[34:22]
James McKinney: So SpotCo, so you end up at SpotCo. What was that learning there for you?

[34:25]
Jeff Rogers: Oh my gosh. That's really the point where things took off like crazy because I got to, and again I showed up about six weeks after we moved and I was like I was going to Comedy Central and I was going to New York Times, and I was like meeting all these people. People were like I think Comedy Central is like, "You should come work here," and I'm like, "Uh, what?" So like I met at SpotCo, this was all within a couple weeks, this woman Gail Anderson who is it's like if you're a designer you know who that is. She's one of the top people in our field. I met with her. At that point, didn't know who she was. I would have been like very, very nervous if I had known but I was like… Turns out they, and I had a bunch of theater posters in my portfolio and the agency worked on Broadway theater advertising, for Broadway Theater basically making theater posters. And somebody had just put in their notice the week before and she was like, she looked at it, she's like, "Great, great. Can you start Monday?"

[35:27]
James McKinney: That's awesome.

[35:28]
Jeff Rogers: I almost like fell out of my chair. So I started and I felt like the dumbest person ever. The other designers there were incredible and I'm like I cannot… I'm going to get fired. I don't know what I'm doing.

[35:44]
James McKinney: Can you give, just for those listening, can you give a frame of reference of what you saw in those designers based on your skillset at the time?

[35:54]
Jeff Rogers: I perceived it, and talking to them later they didn't think I was bad or anything. I just perceived their work as being very refined and just all their ideas, they could just spit out 1,000 ideas and they were great, and then Gail she's a fricking genius. I mean she's a brilliant artist and designer. Working with her that first year, I'd be trying to work on something, some brochure or something. She'd come over, she'd like sneak up behind you and look at your screen, like, "What are you working on?" Like, "Uh! I didn't see you." She's like, "What are you doing? Why are you doing that?" I'm like, "I'm just trying to figure it out." She's like, "Move over." So she'd like just sit down and in a matter of seconds move this, move that, do this and it was beautiful.

Getting to watch her do that, technically do it, and then to talk about… and she's a teacher so that's her heart. Now she runs the design program at the School of Visual Arts in New York. When we got into her teacher mode, she's like, "See this kind of type has this kind of weight, so you want to pair that with this because you get this emotional response," blah, blah, blah.

[37:06]
James McKinney: That's awesome.

[37:08]
Jeff Rogers: So it's just like I'm learning like every day, and also feeling like super nervous every day.

[37:14]
James McKinney: But the amount of growth that took place-

[37:17]
Jeff Rogers: Oh, huge. That first year I was so uncomfortable. I was just like highly anxious but really trying hard, and then it took about a year where I was comfortable, Gail trusted me. We started doing side projects together designing books and all kinds of crazy stuff. I had that, even though the job was really amazing and fulfilling, as a designer it's kind of a dream job, I still would go home and work on stuff that I wanted to work on because I was in that habit. It would have been weird at that point to not.

[37:47]
James McKinney: Early on your side gig, if you will, was to improve your own skillset. That's why you created these theater posters when you were in Texas and now you're in New York and you have some side gigs working with Gail on some book things. What was the reason for the side gig at that point? Was it still just to improve and learn? Was there some monetization opportunities in that? What was the reason for it?

[38:08]
Jeff Rogers: It was fun. It was super-duper fun. I'm the kind of person, I'll get just obsessed with something. The deeper you dig into like a subject or a hobby or something, you know it's like you get real deep you just think about it all the time and that was the way that it was, and I was learning so much at work finally that I wanted to take what I was learning and try stuff with it and experiment where I couldn't do that, like I had a very specific job there. I was an art director so I was designing posters, coming up with the concepts, and hiring illustrators and going on photo shoots and all this stuff. But as I was learning stuff at work, I wanted to come home and be experimental with it and try stuff and tinker with it in my own workshop, you know, in the privacy of my own where nobody could see me fail or critique me.

[38:58]
James McKinney: So if you have this dream job, you're doing things that you absolutely love in the evening hours, why change it all up and start something new?

[39:07]
Jeff Rogers: It was a similar reason as my dad wanted to run his own life and be his own boss, but it was also the more I was doing that… and at the time, social media was kind of it was Flickr. I don't know if anyone remembers Flickr but I was putting stuff out.

[39:26]
James McKinney: It was like, well actually no-

[39:27]
Jeff Rogers: Photos.

[39:39]
James McKinney: Photos, right, that's what it was, okay yeah.

[39:31]
Jeff Rogers: But I was putting stuff out there and so there was all these design blogs, and so things would get picked up and go viral or whatever on a small scale. People started to know who I was from my own work, and then I started getting calls from Nike and New York Times, and actual clients paying actual money for me to do assignments just like I was working on with Gail. So I had already practiced and had some cool opportunities to do some high profile stuff with her, so I knew how to do it. I was also working with illustrators every day so I knew what a bad illustrator was to work with, what a good illustrator was to work with and I knew that if I got hired by someone to do a job, I'm going to do it really well. I'm going to go above and beyond every time and try to get them to call me back, you know? That's my goal. Please the client, make sure that they're super-duper happy, but also get some good work out there and try to get them to call me back.

So I was learning all that stuff at my job, but then started getting some real work on the side from that and sharing work before Instagram and before all this stuff. When I officially jumped ship, SpotCo had kind of shifted. Gail had actually left, a couple of the other designers had left. The department sort of merged in this weird way and I knew how to do that job really well, and I was kind of left to run a couple of the accounts, and I was bored. I mean I could have stayed there for 10 years but I knew I was in this habit of I need to get back into a place where I'm uncomfortable, where is this going. I don't know if I want to do this for the rest of my life. I've got to get back to a place where I'm uncomfortable. And I know that I could probably do it because I'm already getting this work, and then my wife got this incredible gig on Broadway making like gobs of money so I was like okay. So that was helpful.

[41:36]
James McKinney: Yes it is.

[41:37]
Jeff Rogers: So that was a helpful kick.

[41:39]
James McKinney: There might be some listeners thinking well of course that's going to be helpful if you have someone else, but that's part of the entrepreneurial journey.

[41:43]
Jeff Rogers: Until the show closed, yeah.

[41:45]
James McKinney: Part of the entrepreneurial journey is that if you're married, this isn't your own journey. It's a team effort.

[41:50]
Jeff Rogers: Team effort, yes.

[41:51]
James McKinney: That's part of it yeah.

[41:53]
Jeff Rogers: But the funny thing with that is in that decision, I'm really glad that happened and I'm glad I decided to leave. I ended up sticking around for about six extra weeks just to wrap up everything and make sure everything was tied up because I didn't want to be that jerk who's like, "Good luck," you know? I felt like I owed them a lot and so about a week before I was supposed to leave, that show that my wife was making all that money closed, so we were both basically unemployed.

[42:21]
James McKinney: Like unexpectedly?

[42:22]
Jeff Rogers: Unexpectedly. I mean that happens all the time.

[42:24]
James McKinney: Oh, okay.

[42:25]
Jeff Rogers: Where a show will just, like we can't do it.

[42:27]
James McKinney: If it wasn't doing well though?

[42:28]
Jeff Rogers: Right yeah, wasn't doing well.

[42:29]
James McKinney: A successful show doesn't just close.

[42:31]
Jeff Rogers: No, no, no. But sometimes really successful great shows close for whatever reason too early. They'll be around for three months and then… it's just a weird, weird world and a very small, niche world.

[42:44]
James McKinney: Yeah. So you're on your own.

[42:45]
Jeff Rogers: So we're both out of a job.

[42:46]
James McKinney: Now it got real.

[42:48]
Jeff Rogers: It got real but then I remember, I very distinctly remember the first day that I was on my own and it was just me. I got up in the morning, made some coffee, sat down, and I was like I have all day to work on what I want to work on. This is awesome. I had never had that before and it was like whoa. I hadn't even thought about it. Like I can sit here all day and do what I was doing exhausted at night, and I just, man I got a lot of work done. And then jobs started coming in.

[43:30]
James McKinney: How were you, let's talk about the early days, right? First off, that day one you just described, is that day one of your current venture or is that a different-

[43:37]
Jeff Rogers: Yeah.

[43:38]
James McKinney: Okay, so let's unpack your company. What exactly is your brand known for?

[43:43]
Jeff Rogers: The way that I would have described it is I opened the doors to my design studio, my one man design studio basically, but I was calling it a design studio where I was going to keep doing all the work that I was doing on the side. Basically which at that point was typographic illustration. And the types of clients that were calling me to do work were people like New York Times didn't a few Op Ed illustrations, publishers doing book covers, magazine a lot of editorial illustration and magazine covers. And then advertising agencies, things like we're doing this Diet Coke campaign and we want you to do the artwork, and we want to do these different phrases in this artful way.

So they'd hire me to create that art and they'd do all the writing and everything. This agency called because they wanted to, McDonald's was their big client. So DDB in Chicago and they had an idea to have an artist paint a mural in a commercial for this new product. So I went to Food LA and was in a McDonald's commercial at one point, which when they called me, and I was used to advertising agencies calling me to do stuff, "Oh, some lettering and typography for this new product." I'm like, "Great, great, great." And I think at that point I was doing a little bit of freelancing at Nickelodeon. I was in there doing key art for some of their broadcast, I was just floating around doing a bunch of stuff. But that McDonald's thing it wasn't until like the third meeting that I realized that they wanted me to be actually in the commercial. That was a wild experience.

[45:27]
James McKinney: Had you done murals up to that point?

[45:29]
Jeff Rogers: I had done a few big things for the Ace Hotel in New York. That was the first large scale thing that I had done, and again I was like at that point if somebody wanted me to do something that seemed cool but I didn't really know how to do it, I would just be like cool, let's do it, and just try to be confident and figure it out. Because figuring it out and that, it was part of the design process and where am I going to paint this giant 10 foot by 12 foot canvas? I don't have any room. So figuring that out, where am I going to go.

[46:02]
James McKinney: That's awesome.

[46:03]
Jeff Rogers: And I still was putting everything out there online, and doing time lapse videos and stuff of some of the bigger work. I hadn't done that that much, but there was a lot out there, and I did a new website and everything. So people I think were finding me. My brand if you recall, it was just me. I always just used my name. I was hired for really I call it typographic illustration. I mean it's like, that's kind of like the bread and butter.

[46:35]
James McKinney: So if I go to your clients and I say, "What's Jeff known for? What would you say is unique about Jeff?" What would that be?

[46:45]
Jeff Rogers: I would hope that they would say great typography. I would hope that they would say that. Which is funny because in Dallas when I was walking around and talking to everybody, the one thing that everybody consistently said was, "You've got to work on your typography skills." So I did.

[47:00]
James McKinney: That's awesome.

[47:02]
Jeff Rogers: So that's like what I do now, which is funny.

[47:04]
James McKinney: Was that key to one of your learnings under Gail?

[47:07]
Jeff Rogers: Yes. She was like the typography queen of the design industry. If I hadn't worked for her, I'd probably still be struggling with it maybe, or my work definitely wouldn't be what I am doing now. Working with her was absolutely essential. It was like finding a good mentor, which I think she was the one and only real mentor that I ever had, was key. If I didn't work with her, I don't know what I would be doing right now.

[47:35]
James McKinney: That's awesome. What has been some of the challenges in working for yourself? Because one of the things we haven't talked about is it seems as though customer acquisition just kind of happened for you. It's just you put work out online and clients are coming to you. Well, that's kind of a dream scenario for a lot of people. But what have been some of the challenges you've had as you've built your own brand?

[48:02]
Jeff Rogers: Yeah, it's kind of a unique situation where like I mentioned I really haven't ever done any specific marketing. All I've ever done is try to put work out there where people can find it, which is not as easy now as it was. One challenge is always trying to be proactive about the projects that I'm doing. Now I have two kids, things really changed when they came along. We were still in New York and we moved back to Texas after our second was born, about a year after our second was born just because it was too hard. It's way too hard. And everybody with kids had left and we didn't have any friends, and nobody cared that I was even in New York anymore. I was still getting hired and I would mention like, "I'm down the street if you want to meet in person." They're like, "Oh, you're in New York?" I'm like why am I suffering here, you know?

So one of the keys to my business is doing personal projects, and doing I think a lot of people are using the word passion projects which is what I had been doing at just those experimental projects that I would put out there and then get work from those. Now I have so much out there that people just want me to keep doing what I've already put out there, and that's not sustainable. So I have to keep doing experimental personal projects and getting them out there in order to move forward, because if not things are just going to fizzle out and die at least in my mind, but it's very, very hard to get the time to do it or the energy to do it now.

Fortunately I have a lot of work and it's great. Like I love all the projects mostly that I get to do, but I'm not doing anything new. I'm just kind of doing the same types of things over and over, and I feel like I'm almost stuck again now and I need something. I've actually considered maybe going and working somewhere for a little bit, just to how do I switch this up again. So I've been really trying to force myself to spend 20 minutes, 30 minutes in my work day thinking about something, an idea that I'm curious about. Right now it's just I need to paint. I need to paint more. That's very specific for me what I'm doing right now, but it's so hard. It's so hard for me to justify the time, even though I know that if I don't do that, that I won't grow and I'm in control of the types of projects I'm getting, and I can keep recycling and keep doing the same projects over and over.

[50:47]
James McKinney: One of the things that you stated a few times and I'm seeing this theme in your life and your journey is just that continual growth, pushing yourself. You always frame it in the realm of creativity, but do you think that truth should apply to all entrepreneurs, to constantly be pushing yourself to grow in whatever area you are in?

[51:12]
Jeff Rogers: Yeah. I don't see how someone could want to be an entrepreneur if they're not just psyched about what they're doing, and why wouldn't you want to be the best at that thing? I know that the more I learn, the farther I can see. I know that I can keep getting better until I die, you know?

[51:34]
James McKinney: Yeah, yeah.

[51:35]
Jeff Rogers: I want to keep making work and I want to keep growing and doing new things, and interacting with people and trying to make an impact in a lot of different ways. If you're not going to try to be the best version of whatever your business, why would you even want to do it? Go work for somebody.

[51:52]
James McKinney: You're preaching to the choir, I love that. I absolutely love it. I'm glad those are the words out of your mouth and I hope for all those listening you caught that. But I want to ask this question because for veterans in any industry, there's always kind of a time and place question to be answered or spoken about, and it would be crazy to not ask it. For those that are also in the creative space, you came on the scene digitally, online if you will, in a time when all the creative sources were new. Being the first on any platform is always going to help with being discovered. If you're the first on Tik Tok, you're making a mint right now because of your fan base. You talked about Flickr. I assume when Instagram came online you were probably one of the earlier Instagram users.

So if you were to start your brand today, how would you do it? And this is really a question for those in my audience who are in the creative space trying to figure things out. But at the same time, if you're listening and you're not in the creative space, the same stretching thought process can be applied to anything because time continues on, technology continues on but there are principles that still ring true, and if you don't believe me go back and listen to my episode with Ben Chestnut, founder of Mailchimp, when he spoke to some of the link efforts he used for SEO because they still apply. It's crazy. I want to ask that specific question for you. If you were to start today, how would you do it?

[53:30]
Jeff Rogers: I think I would kind of start the way that I started before, with like a desire to make great work. That's what I love to do.

[53:40]
James McKinney: But how would you get discovered? It's so-

[53:42]
Jeff Rogers: Yeah, I know. I don't know. I didn't know what I was doing back then. All I cared about was just pumping out the work and I wanted to share it, because I had gotten into a habit of talking to those people and sharing my work, and I knew there was a value of getting work out in front of people and getting some feedback on it. So Flickr was a place where people could comment and you could kind of gauge whether a lot of people liked it or if they didn't. That was kind of a good way for me to bounce ideas around off of people, and that was the motivation for me was are people engaging with this, are they not.

It wasn't about followers or likes or anything at that point, which is why now as a common probably frustration for a lot of people in my position was dang it, I should have done more back then because I don't have the giant social media following that a lot of my friends do who when all that was happening they were like, "Oh, here's an opportunity." I was more focused on, I'm not a… I would not consider myself a good business person so like if I was to start right now I would just want to make great work first because that's my job, and just try to keep connected with people. I think connection and community is super key, especially coming from New York.

That's been a very important scaling back. Like in New York everybody wants to take over the world, and I certainly did but it's tiring. And so coming back to Texas I was like I just want to be a Dallas guy. I want to have a community of people and clients who I know and we are friends, and my income is coming from a community and a close-knit… that's what I want. I'm not really overly concerned about being rich. I'm not going to ever be rich. I just want to keep making the best I can and have a really solid community of people who trust me. Trust me to do the work that I want to do, and so that I can really push the limits of what my capabilities are. That's kind of where I'm at right now is that scaling back of I don't care about… it's nice to get those giant advertising projects and we're doing this great project right now for Patagonia that is super-duper fun. I'm getting to collaborate with a really good friend an amazing illustrator on it, and we're getting paid really well.

[56:05]
James McKinney: That's awesome.

[56:06]
Jeff Rogers: So it's like when all those things can happen it's great, but I'd rather work on great fun projects than a boring project and make a lot of money. I'm going to have to do that a lot and I'm glad when I get to make money but it's a bummer when the work sucks, you know, and when it's just like I'm trudging through it just for the paycheck.

[56:27]
James McKinney: No, I get it. You know I want to ask this question and it's really kind of an identity question but I've had numerous conversations with creatives. I've had numerous conversations with creators that create apparel for let's say to sell on Etsy. They're really designers but they don't call themselves fashion designers. There's a persona they think that comes with that title.

[56:49]
Jeff Rogers: Yeah, I get that.

[56:50]
James McKinney: Do you wrestle with any notion that you're an entrepreneur or a creative, or do you separate the two because a lot of people do. I mean do you wrestle with that at all?

[57:00]
Jeff Rogers: It can be confusing to me what I am because it's actually kind of hard for me to call myself an entrepreneur even though I am. I don't know why. I think I'm really hard on myself. Like I just said I'm not a good business person, however I run a successful business since 2011, which I have to like have those two little voices you know?

[57:23]
James McKinney: I think a lot of people, especially on the creative side, when you're a creative I've met numerous creatives that I'm using air quotes, freelancers, but they've been doing it for 15 years and it's like you're an entrepreneur. You've built a business and a brand. Is there a retail store? No. is there an ecommerce store? No, but you're an entrepreneur. And I find the challenge to really be concentrated in the creative space, to identify as an entrepreneur. That's why I was trying to find out, being that you were raised by an entrepreneur who had a brick and mortar bakery, do you have a person of what an entrepreneur is and do you wrestle with whether or not you consider yourself one?

[58:07]
Jeff Rogers: Right, right. Yeah because I don't have a product. I guess I kind of do but my clients are other creatives usually. But that's shifting a little bit where I'm trying to get more work where I'm working with businesses and business owners, and that is a step in a good direction for me right now in my career, because that means that I can help the business grow and improve with design, and I've gotten better at being able to walk people who don't know about creative process or whatever walk them through a process of doing that.

Where working with an agency or art director, they know. We all know what we're doing. We don't have to explain. I can send these rough sketches over and they're like, "Hm, how about this one?" And I'll be like, "Uh, why does it look such like a cartoon?" It's like it's a sketch. Where you can't just send a business owner a sketch of an idea because they're going to think that's what you want to do. So things like that, I don't know, that's a weird question. I've never really thought about it because I know what I do is very specific, and my clients aren't like the masses of people wanting to buy a product or something. I have very specific client base that I want to work with.

[59:28]
James McKinney: I think part of why it's probably challenging to answer is because there's this narrative of what entrepreneurship is and the reality is if you're taking risk to build something with the chance of failure, there's a transaction taking place, you're an entrepreneur. I mean again that's a really rough definition, but the truth remains the same. I believe someone can have a side gig and be an entrepreneur. I think the narrative that's out there of what entrepreneurship is has done more damage than good. I think it has not created these aspirational goals for people because there are people, I call them the wantrepreneurs, the ones that have a 9 to 5 and a book full of dreams and ideas, but some level of fear and reluctance to move forward on it because there's something out there that says if you're not all in on it you're not an entrepreneur. It's like that's not true at all. That person can very much be an entrepreneur for certain pockets of the day because that's what their lifestyle affords and they're trying to do it incrementally.

[60:36]
Jeff Rogers: That's true. When you put it like that, that's more helpful. I have these expectations, even in my own field, where oh I should be hiring designers and I should be growing this business, and I should be making tons of money. If I'm an entrepreneur, I should be like a gazillionaire if I was really successful or something. I don't want to run a big or manage a bunch of people, it's not what I want to do. I want to make stuff and I'm good at it.

[61:05]
James McKinney: and you've been doing it, that's the thing. Again, there's this false persona of what entrepreneur is and there's so much diversity in entrepreneurship which is why I love The Startup Story.

[61:16]
Jeff Rogers: It's awesome.

[61:18]
James McKinney: We get to explore that. And unfortunately our time is coming to an end so I want to make sure I honor my audience's time with asking the same questions that I ask every founder. And that one being about gratitude. We've talked a little bit about the people I suspect you're grateful for, but when you look back across your entire life's journey who are the people that you look to with such immense gratitude for their contribution to where you are today? And the reason I ask that question is that I believe if we forget those people, if we forget their contribution, we think we did this on our own and ultimately that isolates us, and that will always lead to failure. So who do you look back to with such immense gratitude for their contribution to where you're at?

[61:57]
Jeff Rogers: Oh man, that's a good question. I actually think about these people a lot because it's like that pay it forward thing. It's like I can be more generous when I think about my gratitude. Definitely my parents, my wife, my career. So grateful I got the opportunity to work with Gail Anderson and those people in Dallas that took the time to talk to me. People like Paul Jerty and Tod Hart and Rob Wilson are people that spent some time talking to me. And I know now from that if I spend five minutes saying something to somebody, it could mean nothing but they might remember it for their whole life and it could really help them, even just that little word or something. That's definitely I remember little soundbites from people that help me almost every day. All those people that took five minutes to help me.

[62:48]
James McKinney: I love it. And for our final question, we've been talking at a very high level about your personal journey to Howdy Jeff, where we are today. People have had a chance to kind of listen in at a kind of 30,000 foot view of what that story looks like. But I want to bring it down to the one. I want to bring I call it a mentor minute where this is you sitting with one of my listeners. Whether it be the frustrated entrepreneur who has been doing this for 10 years, lack of traction, constantly having cash flow issues, maybe COVID completely jacked their business up and they don't know if they can make it out of 2020. But either way they're frustrated, they're discouraged. They might just want to call it quits. Or maybe it is that wantrepreneur that we talked about who has some narrative as to why they can't just go all in on something and move forward on it because they have a false idea of what entrepreneurship is. Whoever it is, whatever person you want to speak to, if you were having coffee with them right now what would you say to that one person?

[63:45]
Jeff Rogers: I think if you're in the creative field, specifically a designer creative, photographer, something like that I hate that the idea this phrase that's floating around idea that's like live your dream, yay. Because I see that, I know you see that all over the place and think I can't live my dream. I've got kids, I've got this, I've got to work, I've got to live my life, it's not that easy. Apparently, it's easy for everyone else because that's what I'm seeing, and I see that all the time and it frustrates me because it's not easy.

It's actually extremely difficult and I wish people would stop posting that stuff. Because it gives me and I'm sure it gives you a false sense of expectation that you have to be successful and taking a picture of yourself in a flowery meadow and like life is hunky dory and awesome. But it's not going to be. I've had a lot of struggles and hard times, but getting to work on things that I want to work on, getting to run a business the way that I want to, even when it's hard and maybe doesn't work all the time just getting that opportunity is worth it at least for me, because I own it. And if I can take ownership of my life and my work, it's worth the struggle.

[65:08]
James McKinney: Once you've had a few moments to process all the value that Jeff Rogers brought us in this week's episode, please hit me up on LinkedIn, Facebook or Instagram and share with me your thoughts on this episode. And lastly if you've been around The Startup Story for any length of time then you know how much emphasis I put on the idea that entrepreneurs support other entrepreneurs. One of the most common challenges for all small businesses is gaining awareness, and with that in mind there are two key ways you can show up to support Jeff Rogers.

First connect with him on LinkedIn, and we'll have a link in our show notes for easy access. But the other way is to connect with him on all the social channels by following FRogers, it's actually I know it sounds weird and unique but it's actually the last letter of his first name - F, Jeff - and then his last name Rogers, R-O-G-E-R-S. So FRogers, got to love creatives. Remember entrepreneurs support other entrepreneurs so let's show up for Jeff Rogers in a very big way and as a thank you for all the value he delivered today. And now for my personal ask.

The Startup Story community has been so incredible about sharing our podcast with others, but we have more stories to tell and more people to reach. We too are a startup and word of mouth is everything, so please follow us on Facebook and Instagram @TheStartupStory or on Twitter @StartupStory_. If you're on LinkedIn, please search for The Startup Story and follow our company page. LinkedIn is a really powerful way to raise awareness of the show. But the most impactful way you can help us grow our audience is to leave a review on Apple Podcast. Or if you listen to the show via Spotify, then please simply share the podcast directly from your Spotify app or wherever you listen to the show.

These simple actions can make a huge impact in getting these amazing founder stories out to the masses. And please make sure to tag or mention The Startup Story when you do share so that we can connect with you and say thank you directly. I'm so incredibly appreciative of the fact that you listen to the show each and every week, and I look forward to sharing these amazing stories with you every Tuesday with hopes of encouraging and inspiring you to start your story.

If you like this podcast and are thinking of creating your own, consider talking to my producer Danny Ozment. He helps thought leaders, influencers, executives, and authors create, launch, and produce podcasts that grow their business and make a real impact in this world. You can contact him today at emeraldcitypro.com/startupstory.

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September 22 2020
Jeff Rogers, founder of Howdy Jeff

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