Relationship Building

Motivation, Mentorship, and Competition (Ep. 115)

The amazing D’Wayne Edwards joins Tim today to talk about education, motivation, and providing kids unique opportunities that engage them in learning. D’Wayne is the former lead designer at Nike, and has now founded the Pensole Academy in Portland for footwear design. In today’s episode, he shares his own story (2:30), talks about the how and why of starting Pensole (5:15), and introduces his new Sneakerhead of State footwear design competition (13:00). Full episode transcript below.


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Welcome to Art Ed Radio, the podcast for art teachers. This show is produced by The Art of Education, and I’m your host, Tim Bogatz. We talk all the time about how to engage our students, how to motivate our students, how to find new things that are going to interest them, and I think I’ve found a really nice option for doing just that and the person bringing it to you is D’Wayne Edwards.

Now, I was lucky enough to be introduced to D’Wayne who is the founder of the Pensole Academy Footwear Design School in Portland. He has a remarkable story from growing up in LA, all the way to being the top designer at Nike and for the Jordan Brand, and now starting his own school. I’ll let him tell you about his life, his career, and his school Pensole which is a unique place that is doing some incredible things, and one of those things is a new contest called Sneakerhead of State. It is a competition that has all kinds of options for designing sneakers, from footwear, to graphics, to color, to apparel, and if you’ve got kids that are into art and into sneakers, it will be exactly what they are looking for.

Like I said, D’Wayne can tell you about all of this better than I can, so give us just a second here. He’s on the line now, let me bring him on and we’ll talk about his school, his competition, motivation, mentorship, and all sorts of incredible things. Here’s D’Wayne. All right, and D’Wayne Edwards is joining me now. D’Wayne how are you today?

D’wayne: I’m doing great. How are you sir?

Tim: I am doing really well. I want to thank you for joining me. I’m really excited to talk to you today, and I guess probably a good way to get started is for you to just share your background for everybody who’s listening. So, can you tell me about your personal story I guess, where you come from, how you got started in design? Then, your career has been all over the place. So, if you can just tell us a little bit about that? I think listeners would love to hear it.

D’wayne: Yeah. Let me let try to sum up 30 years in a few seconds.

Tim: All right.

D’wayne: I’m originally from Inglewood, California and I grew up wanting to play professional basketball because that’s where the Lakers played when they first moved to California was Inglewood. So back then, they didn’t have the fancy practice facilities that they have now, so they actually practiced at my high school. So, every day I would see the Lakers come and practice, so that the idea of being a professional athlete was staring at me almost every day.

Unfortunately, I stopped growing at 6’1″. I was the shortest guy on my basketball team in high school. So, luckily I was able to draw, and so I just dove into drawing and I’ve wanted to be an artist. It wasn’t until after I graduated from high school, I found design. Before then, people only knew art and those who didn’t know what design was. This is in the late ’80s. So, I got my start as a professional footwear designer at the age of 19, shortly after I graduated from high school and worked my way up through LA Gear, designed product for a lot of NBA players back then. Left LA Gear, worked at a company called Skechers.

Skechers had the licensing rights to design footwear for a new streetwear brand called Karl Kani Cross Colours back in the early ’90s. Back then, I got a chance to work with Tupac Shakur, Notorious B.I.G., Dr. Dre, Snoop Dogg, Puffy, all before they were big mega stars. So, I was designing footwear for those guys in early ’90s, did that for about six years and then Nike came calling, asked me to move up to Oregon to design for Nike.

A year into my Nike job, the Jordan Brand asked me to join the Jordan Brand. So, I became the youngest design director in Nike’s history at 30 when I joined the Jordan brand in 2001. I was there for 10 years or almost 11 years and designed products for all the top Jordan athletes including Michael himself. During that time, Google happened and the idea of being a designer was a bit more common in the sense of kids would draw shoes and email them to me, and that led to me creating a design competition while I was in Jordan called Future Sole, and it was really just a way to discover new talent and giving these kids a roadmap of how to get into our industry. I did that for a few years, and I just loved the idea of developing people, and mentoring people, and guiding people.

So I decided to leave, completely left the industry, left the top spot and the whole industry to start my own school called Pensole. Pensole is here at downtown Portland, and we’re the only footwear design academy in the world that teaches you everything from sneakers to high heels, and we work with some of the top footwear companies throughout the industry. This year, actually just last week, we placed our 400th former student into a job in the last seven years.

Tim: Wow, that is really impressive. Yeah I love that, and I actually want to talk a little bit more about Pensole if you don’t mind. I mean, because it seems to me like that’s a big jump going from the premier spot in footwear design to just kind of leaving that behind and starting your own company. So, can you talk a little bit about the motivation for starting Pensole? Why do you want to start a footwear design school? Do you want to open up those opportunities? Is it about showing kids the road map like you mentioned, or what is the motivation then?

D’wayne: Yeah, you hit it right on the head man. When I was a kid, I wanted to be a footwear designer, and no one knew what that was. No one knew where actually go to school to do it. There were no schools that taught it, and I was blessed enough to still get into the industry at an early age and throughout that whole time, there were still no schools that taught it. as I mentioned before, Google happened and so kids were able to start sharing their work with people and sharing it with me, and I just felt like it was more rewarding for me to design … Look at, I guess designing lives instead of designing shoes.

Where I’ve designed shoes for almost every person I’ve ever wanted to design product for, and once I started working with kids and seeing that light bulb turn on, and for them to be able to have the same experiences I was able to have, that was just so much more rewarding to me. I just felt like that was my calling to do. That was what I was blessed to be able to have a long career to do, plus no one had done it before. I knew what the industry need, and so I just decided to take the leap of faith and go off and try to do this teaching thing that I never did before, especially since I actually never went to college for design either. So I’ve never went to college for design. I end up getting a design job, prior to the top spot in the whole industry.

Tim: Yeah.

D’wayne: I figured that was possible, so why not try this?

Tim: I like that. I’m impressed by the fact that you don’t have a ton of experience when it comes to the schooling and the teaching aspect, but you’ve put together something that’s really impressive. Pensole has classes. You have a Skills Academy, all kinds of really impressive opportunities available for kids. So can you describe, I guess some of the opportunities that you have for high school students and particularly kids who are sneakerheads, kids who are interested in footwear design? What do you offer them?

D’wayne: Well, what we offer our kids is a direct link to the company they wish to work for. So, we teach you the way you will work at a company. We don’t teach the theory of anything. Everything that we do is really learned by doing, hands on projects, actually, real time projects where some of our programs we partner the students directly with the company, and they work on a project that’s directly for that company that could actually even be sold at retail as well.

So, we give them the experience of what it’s like to work at a company without physically working at that company. The part that I didn’t mention is a big chunk of what I’m doing for Pensole is what I wish I would have been able to have done for myself, where being the youngest of six kids not able to actually afford to go to college, I didn’t want that to be a barrier for kids either. So, the majority of everything that we do is free for students. So, the companies pay for the student’s tuition and their housing, if they’re coming from other parts of the country, or at another parts of the world, but we’re really trying to create that roadmap. That roadmap that they can see like, “Hey, I have this artistic ability. Maybe I should redirect it in this sneaker thing that I love because I’m buying, and trading, and selling sneakers all day, maybe I can take my hand at designing them and creating them.”

So, we’re kind of giving those sneakerheads another option similar to when I was trying to play basketball, now I have another option. I didn’t make it to the NBA, but my shoes have made it to the NBA, and my shoes made it to Major League Baseball, and to every NFL field, in multiple Olympics. So, my sports dreams didn’t die because I couldn’t do it, it just manifested itself in a different way, and that’s what I want to help kids understand that there’s options to living your dream, it just may not reveal itself, it may take a little time.

Tim: There you go, there you go. Now, I do want to revisit, and I mean still talking about Pensole and everything that you do. Something that you mentioned back in the first question was the mentoring aspect. I know you have a lot of designers working in the industry, you said just 400th that you just placed, and a lot of them come back to mentor at Pensole and come back to help your current students. So, I guess the question I want to ask you is like, why is the mentoring aspect so important to you, and what do you think the benefits are like? How does it help the students that you work with?

D’wayne: I’m a product of mentorship, and without the mentorship and guidance that I received early on as a 19-year-old kid working at a big corporation, that’s intimidating. To have the owner of the company, actually Robert Greenberg, have him take me under his wing and once he set that example, then the other designers that I work with followed through with that as well. I’m a product of mentorship, so I understand the importance of it. When designing Pensole, that was the goal, was to be able to educate kids and get them to understand that someone gave you a chance, and someone gave you an opportunity, and it’s your kind of responsibility to also give that right back.

So, you’re absolutely right. All of our students come back, and mentor and develop kids because they sat in the same seats that these new kids are sitting in. It’s great for the new crop of kids to see them because they can relate directly to them by age, where I’m a bit older than them, but it’s a beautiful thing to see when you’re just now educating a kid and say two or three months later they’re coming back to talk about, “Hey, this is my first month on a job. This is what it’s like,” or someone is talking about their first year, or someone comes to talk about the 10th or 5th year.

So, having that valuable insights that you can’t really get from school, that part is the thing that helps you get a jumpstart on your professional career when you get an opportunity to get in because they’re giving you these little nuggets and gems that this insider information that helps you prepare for that interview, prepare that portfolio, prepare for that first day or first 90 days. So it’s invaluable, but it’s ingrained in what we do, everything that we do actually.

Tim: Yeah, that’s beautiful. I love that. Now, I know that you’re trying to open up a lot of these ideas to kids just all over the country. You have the Sneakerhead of State competition going on right now, which is a great name by the way. Can you tell us a little bit about the competition, the inspiration behind it, and the reason that you wanted to do it especially?

D’wayne: Yeah. One of the things we wanted to do too is make education more fun and make it appeal to these kids, make it speak to these kids in the language that they know. Sneakerhead of State is, it was a simple idea of, “Hey, I want to find the best sneaker designer in every state and then pair them together to find the best sneaker designer in the United States.” So, being able to in a similar athlete model where when you play ball, you’re like all city, and then you play with the all-state kids, and then you play with the whole country when you go to college.

Tim: Right.

D’wayne: So, it’s really getting these kids to see like, “If you think you’re good at the city level, well, let’s see how good you are in your own state. Then, let’s see how good you are with the whole nation.” It’s really kind of that simple premise of giving these kids another outlet and giving it to them in a really simple format where it’s all online. All you have to do is submit a sketch online. There’s no curriculum. It doesn’t have to go through the school process.

I hope the schools, the teachers actually shared with their students and maybe it becomes a curriculum project, but it’s really trying to reduce the barrier of entry for them to see that there is alternative career paths that they may not have never heard of, but it exists in their whole circumference of everyday life where these kids have sneakers. They go to the malls. They go to sneaker stores. They always talk about how it would be nice if it was in this color, it would be nice if it did this or did that. I mean, some of these kids are making four and $5,000 a month man, buying and selling sneakers.

Tim: Yeah. I think as teachers, we’re always looking to tap into that. Like you said, things that they’re already interested in, things that are part of their world. I think this contest does a lot of that, and on top of that as teachers, we can appreciate that. Like you said, the way you want to bring the joy to education, I always want to make it relevant to our kids and I think this contest does that. So, we’ll get it out to everybody but just all the details how people can enter all that kind of stuff, but for teachers who are interested, who are saying, “Hey, this sounds good. I want to check this out.” Can you give us a few more details?

You said it’s an easy contest. Can you talk about what it requires, and then I guess more importantly the incentives for the kids. What the possible awards are, and why kids should sign up, or why they should enter?

D’wayne: Yeah, definitely. So, the website,, really simple. What we’ve done is we created four different areas for kids to participate in. They can participate in one, two, three, or all four. One of them is footwear design and we give them outsole template to use, and they just draw the upper. Another is color design which is we give them a template they can download and just color it. The third one is apparel design. Again, you have a template for them to use, to create a new product on. Then, the fourth one is graphic design.

So, the reason why we’re doing these four different tracks is because we want to try to meet the kids where they are, depending on their interest. So, we have these four different tracks. These are four different career paths that only one of them, graphic design you can actually technically learn in college right now, and apparel. The footwear design and color design you can’t actually learn in college, its transferable skills. So, we’re trying to let them know like, “Hey, this is a real career opportunity.”

So, the way it works is we’re launching it now nationwide. We’re going to get in all the submissions. We’re going to select the best 12 kids. Three from each of the four tracks. We’ll fly them. I’m sorry, before we fly them to Portland, we’ll assign an online mentor to help them further develop their designs, and then we’ll fly them to Portland. They’ll spend one week with their mentors. We’ll develop physical samples of their product. They’ll get a chance to pitch their designs in front of design professionals, and the winning student in each of the four categories will receive a scholarship to attend our college program here in Portland, Oregon in partnership with Pacific Northwest College of Art.

So, we have a 12-week session that they would receive a scholarship too, and then if they choose to stay for the other two years, then we’ll also pay for that education as well. What we’re trying to do is create some incentives and opportunities for schools to participate where the school with the most submissions wins a cash prize. The school where the winning student actually attend, they win also a cash prize. I think the best part for me at least besides a free education part is that the winning designs will all be sold at retail on, but the kids will have a chance to be able to see their product being made and sold for everybody to purchase.

Tim: Yeah, that is just such an incredible opportunity, and hopefully we can get it out to as many people as possible because I think that’s just awesome for the kids. So D’Wayne, thank you so much for coming on, telling us about everything you have going on and kind of sharing this opportunity with everybody because I think teachers are going to respond well. I think they’re going to love it, and I think more importantly, kids are going to love it as well. So, thanks for your time. I appreciate it and I really enjoyed talking to you.

D’wayne: Yes, thank you very much, appreciate you as well. Have a great day.

Tim: That will do it for us. Now, we’re going to link to everything that D’Wayne talked about today including the Pensole Academy, and more importantly the Sneakerhead of State competition. So, make sure you catch those links and make sure you get that opportunity in front of your kids. Hey, as D’Wayne said, there are four different options available for that competition: apparel, color, graphic design, and footwear. If one of them is of interest to your kids or if all of them are of interest, I would definitely encourage you to get them involved with this contest. They are going to love it. It’s something really unique, and if your kids are into sneakers at all, this is a spectacular opportunity. So, go to to see all the details and get your kids registered, check out how to make the entries.

Also, as we’re talking about motivating our kids, finding things that are interesting for them, I want to tell you about one of the Art Ed PRO Learning Packs that I filmed a while back called Creative Ways to Motivate Reluctant Learners. It’s all about different ideas and different opportunities to engage our kids whether that be through concepts, or ideas, or materials, or just trying something new. I kind of bring that up because I feel like this contest is something that would fit in pretty well. It’s motivating, it applies to kids’ interests, and if you’re looking for more ideas like that, the learning package is worth checking out.

Since we’re talking about PRO, I just want to tell you about how many different teachers are getting PRO subscriptions paid for by their schools. I’ve heard from teachers whose admins are using PD money, some admins are actually buying subscriptions for all their teachers instead of textbooks. I mean honestly, do you want a class set of textbooks that we all know are not going to get used, or do you want something that is constantly changing, constantly improving, and continues to make teachers better?

There are videos, there are resources that are immediately applicable, and they show you how to improve your lessons, and give you ideas and guidance for new concepts and new ways of teaching. I don’t want this to turn into a rant, but think about like PRO is going to be so much more valuable than 30 print-making books that you and your kids do not care about at all. Districts all over the country are beginning to realize this thankfully, and hopefully yours can get on board as well, and they can check it out at the for schools.

Anyway, go talk to your admin about getting PRO, and then go to to get your kids registered for this awesome contest from D’Wayne and from Pensole. Use the competition as a supplemental assignment or a sketchbook assignment, or even something as an extra opportunity for the end of the year. For your advanced kids, it’s perfect for after they turn in their AP portfolios. No matter your situation, long story short, you have some kids who are going to be interested in this.

Make sure you also visit to see the show notes for this week, links for everything we talked about, and check out Pensole and the Sneakerhead of State competition. Like I said, we’re always looking for new things to motivate our kids, to engage our kids, and get them excited about what we’re doing, and bringing joy to learning like D’Wayne said and this is the perfect opportunity.

Art Ed Radio is produced by The Art of Education, with audio engineering from Michael Crocker. Now, you guys have been spoiled the last couple of weeks and I’ve been spoiled too to be able to talk to some pretty famous people. Claire Lieu last week, D’Wayne Edwards this week. Unfortunately, we’re going to be stuck with Abby Schukei next week. I think we’re going to have a pretty enjoyable conversation about how you can keep kids from trashing your art room. So, make sure you tune in next week and we’ll talk to you then. Thanks.


Magazine articles and podcasts are opinions of professional education contributors and do not necessarily represent the position of the Art of Education University (AOEU) or its academic offerings. Contributors use terms in the way they are most often talked about in the scope of their educational experiences.