Jesse Joeckel of Whalebone Creative
How the builder of one of the coolest brands defines success and happiness.
"FEARLESS CREATIVE LEADERSHIP" PODCAST - TRANSCRIPT
Episode 165: Jesse Joeckel
Hi. I’m Charles Day. I work with creative and innovative companies. I coach and advise their leaders to help them maximize their impact and grow their business. To help them succeed where leadership lives - at the intersection of strategy and humanity.
These next few months are going to be chaotic. Industries are being reformed, culture is being redefined. New rules are being written and rewritten. It’s happening already. Decisions are being made today, about how to compete for talent and relevance in this new world. So, how should leaders lead as we meet a world of new possibilities and expectations?
This week’s guest is Jesse Joeckel, the founder, owner and designer at Whalebone Creative. Based in Montauk, New York, Whalebone describes itself as a lifestyle brand that’s built around art, design, and surf culture. They sell super soft t-shirts, hoodies, hats and more, and they’ve been doing so since 2010. And they have become the definition of a very, very cool brand.
Over the eleven years since he started Whalebone, Jesse has never strayed far from his definition of success.
“I guess the number one thing is just not taking yourself or life too seriously. We're not here for a long time, let's enjoy ourselves. I think that translates through the brand, I would hope. From my perspective that's what I hope it's putting out. Yeah, we're just trying to have fun while we're here.”
Over the last few months, many, many people - maybe most people - have spent time thinking about what they want from life.
Based on the number of people who are leaving their jobs during what has come to be known as the ‘Great Resignation’, the answer is ‘not this.’ Indeed, in some industries, a third of the people resigning have no clear idea about what they will do next or where.
By the millions, people are challenging their own definitions of success. And even more fundamentally, their definitions of what it means to be happy.
If you’re a regular listener to this podcast, you’ll know that most of my guests are people who are responsible for leading teams of anywhere from dozen to hundreds to thousands to ten of thousands of people. Those leadership positions come with expectations. They also reflect the ambitions and dreams of the people that occupy them.
Once you get on to that ride, it’s very hard to get off. Until a pandemic comes along and teaches us that nothing is certain or permanent or predictable.
If you compressed the life of the earth into a 24 hour period, the entire history of anything that’s even remotely resembling human beings would last 84 seconds. Or less time that you’ve been listening to me today. If you measured the existence of homo sapiens, on the same basis, our entire 200,000 year history would last less than 4 seconds.
There is no measurement small enough to identify the length of our individual existences. Or the lifespan of any business. Or the lasting impact on human history of anything that any of us do.
200,000 years from now we will not even be dust in the wind.
How do you define happiness? And how can you bring happiness to others? That strikes me as a pretty good measurement of leadership.
Here’s Jesse Joeckel.
Charles: (03:22)
Jesse, welcome to Fearless. Thanks so much for coming on the show.
Jesse Joeckel: (03:24)
All right. Happy to be here.
Charles: (03:27)
Tell me, did creativity play a big role in your childhood?
Jesse Joeckel: (03:31)
Yes it did. For sure. My mom is really creative as far as… she's very artistic. Never pursued it herself, as in a career path. But, I mean, as long as I can remember I always had a notebook, a pencil, pen, crayons, whatever. At a desk, a creative zone, always in front of me. Yeah.
Charles: (04:02)
What were you drawing?
Jesse Joeckel: (04:03)
I don't know. Probably typical kids stuff. Like cars, houses, that kind of thing. She would sit with me a lot of the time and just do her own thing. I was always like, look at what I'm doing and look at what she's doing. I'm like, all right, so this is going to push me to hopefully be that one day. Yeah.
Charles: (04:28)
So she was a real inspiration.
Jesse Joeckel: (04:30)
She was for sure. This question just sparks it for me because I never really think of it like that. But yeah definitely, she probably... I don't know, maybe she saw something in me. Not that I was a great artist from a young age or now, but she definitely pushed me more so than I think my brother. Yeah.
Charles: (04:59)
Did creativity play a role academically?
Jesse Joeckel: (05:02)
I'm an awful, awful student. I've always been hands-on. I could never… sitting, science class, math class, I'm terrible with numbers, and I just could never keep my focus. But through grade school and high school I definitely excelled at anything that was more creative. Then I actually, I don't know how this worked out, but through high school I was so bad at math that once I passed a certain level, I don't know, maybe I broke the mold in this sense. But they would let me take advanced art classes or photography classes, which I was really into. I was able to get my credits enough to graduate high school to further my education. But I don't know, that's a whole ‘nother ball game. But yeah, it's tough for kids who are not... I just don't have it and it's not like I'm not an intelligent person. I'm just not wired that way whatsoever. I'm still not.
Charles: (06:17)
Yeah. I'm the same way. I think the education system does a pretty terrible job of allowing people like you and I to actually get an education that matters.
Jesse Joeckel: (06:24)
If you think about it it's like, if you're well off, which I was never well off, you're just... I'm in public school my whole life. You have to mold yourself to their curriculum. Obviously I'm better off than some people who have absolutely nothing. What if that kid is super creative but is awful at math. He'll never get out of high school, but he could be one of the best whatever. He could be a web designer, graphic designer, a painter or whatever. What if he is like… but just never has that opportunity because he is held back and shut down so early in life? Yeah. I always think about that.
Charles: (07:13)
Where do you think you got the confidence to chart your own course? To recognize, the education system isn't working for me and I'm going to just do it my own way.
Jesse Joeckel: (07:19)
I think it was my only... it was either that or nothing. Honestly, I remember one of my math teachers who was particularly not very kind to me and just thought I was slacking off. She always said that I had surf brain because she thought I was some surf beach bum, stoner or whatever, which, I mean, I was definitely a beach bum, I loved surfing. But more I was a competitive surfer. It wasn't like I'm like, "I'm going to sit at the beach and whatever." But I was like, that's so unfair for this older woman to be putting me down because I'm not passing these quizzes or tests or something. I'm like, yeah, I'm not out to lunch thinking about something else. I just, it's not working for me. Then, but, put me in some art class and give me an assignment to try and create something I would probably be average or above average or whatever, and feel great about it, and be not put down about it. People are promoting your creativity instead of shutting you down. Yeah.
Charles: (08:27)
So you're always pushing against the establishment.
Jesse Joeckel: (08:29)
Yes. Not aggressively, but I'm definitely... I would say I'm pretty anti-establishment. I don't think there's a cookie cutter answer for everyone to live their life. How could you say, of the billions of people on this planet, that everyone should follow a certain path? What's right, what's wrong? It may not be what's right and what's wrong for you, for anyone. Yeah.
Charles: (08:58)
What was your transition into the working world?
Jesse Joeckel: (09:04)
I come from... my brother would be third generation commercial fisherman. My grandfather, who was another huge creative influence in my life, he lived off the land. He was a fisherman, he hunted. My father was a commercial fishermen from a very young age. He set the forefront for a lot of commercial fishing practices. My stepdad is also, still is to this day, a commercial fisherman. He long lines for tuna and swordfish and he's still out 10, 12 day trips and he's 66, something like that, walking at a right angle. His back is so beat up and his hips from being on the boat so long. But yeah, and now my brother's a commercial fisherman.
So maybe I could take a shot at doing something creative and not working on a fishing boat for the rest of my life. It was always an option for me, but I was like, let me take a swing at this first and see where it takes me. Yeah, just, I mean, I started as just freelancing after I got a graphic design degree. Just was freelancing and just got the opportunity to try and make my own path and start my own brand, which I did and still doing it to this day. Yeah.
Charles: (10:38)
What was it like being a graphic designer in a family of fishermen?
Jesse Joeckel: (10:42)
My family is super easygoing. I don't think, I don't know. My brother always used to make fun of me, whatever, jokingly but like, "Oh yeah, go paint some pictures," kind of thing. I'm like, "Good one." But no, we have a good relationship. It was good. My mom always pushed me. My dad always pushed me. I'd always get my tuition check and stuff. I always open it and he'd always have a little handwritten note in there. It was cool to see he was... yeah.
Charles: (11:25)
What kind of things did he write?
Jesse Joeckel: (11:26)
"You make me proud.” Every time. Yeah. I did my best to make him proud, hopefully I'm still making him proud. But yeah, it was... yeah, I just, I think I would say that most people would be like, "Yeah, that's great that you chose something different." Yeah, happy I did.
Charles: (11:49)
How did the business come about from a graphic design focus?
Jesse Joeckel: (11:54)
I was freelancing and I was getting a lot of requests for doing graphics for t-shirts and things of that nature for surf shops and some surf brands and I loved it. I was like, oh, this is great. It's right up my alley mixing what my number one thing to do, which is surfing, and then number two thing, which is trying to be creative in design. It was good but I wasn't getting paid anything. I was like, "This is fun and all, but I'm…" I was young so I'm like, all right, I'm putting X amount of hours into say these 10, 12 designs for these people. They're paying me nothing, and then they're going around and selling a couple of thousand of these t-shirts at X amount of money. I'm like, "Man, they're getting this for nothing and selling it for something."
I was like, "What's to say that I can't just do this on my own." Why don't I start a brand? Because what I'm designing for them is just what I would design for myself. A lot of times there was no direction. They were like, "Oh, I like your style. Make us 10 t-shirt designs." Okay, great. I'm like, all right, what if I just made 10 t-shirt designs for myself and had a brand name and sold it under this brand name? I was like, oh, this is great that they were successful off what I was doing, but why can't I be successful instead of making $20, $30 at design, whatever it was.
Yeah. I actually got lucky. This really cool space came available in Montauk, where the brand is based out of, where I grew up. This was long before the popularity of Montauk, which it is now, which is night and day. I found this little shack attached to this old fish market and it's on the water. I could throw a stone out of my back window into the bay. I got this space and I was originally, I'm like, I'm going to start a… I wouldn't say agency because I was by myself, but a creative space where people could come, local businesses could come. I would design for them, whether it be just a logo, or rebrand their menu at their restaurant, whatever it was. That was my idea. I was like, on the side I'm going to make all these t-shirts, and hats, and sweatshirts, and stuff like that, and I'm going to sell it in there.
Literally one week in, people are just buying all these shirts and hats, selling out immediately. I was like, "All right." I go, "You're telling me I don't have to work for anybody else, and I could just work for myself and design and create and put out this product and make a living off of that?" I was like, "I'm in, this is great." That was 2010. This is my 12th season, 12th summer season.
Charles: (15:21)
How did you figure out how to make t-shirt, hats? What was the process by which you learned the manufacturing process?
Jesse Joeckel: (15:27)
Well, I bought a screen press.
Charles: (15:32)
Had you ever used one before?
Jesse Joeckel: (15:33)
Never used one. As many things that I've done through college and even in high school and all that, I just never... it was never something that I was able to learn. But, I mean, YouTube is a pretty good educational tool if you don't know. If you want to rebuild an engine or you want to learn how to screen print, you could learn it through YouTube University, so that's what I did. I just watched some movies and obviously terrible stuff at first, but I know, I feel like people gave me a couple of chances to get it dialed in and that's what I did. For better or worse, I'm still printing a good amount in there. I have the press in the space. You walk in, retail everywhere, and then this four-color press and a dryer in the back corner there.
Yeah, I'm still doing it, still learning. It's not the easiest thing to do. But yeah, I started with nothing. I had like five grand saved up from giving surf lessons in the summer. That was it. That's what I started this brand with. Yeah, I had to keep a low overhead. I couldn't outsource anything. I couldn't find a factory and this and that, so I just inched my way through it year by year until where I am now. But yeah, it was not an easy... a lot of learning along the way, for sure.
Charles: (17:16)
Where did you get the raw materials from. Where did you get the t-shirts and the hats from?
Jesse Joeckel: (17:20)
There's tons of companies that sell blanks. I just, over the years, you find something that's better than the last. Softer. I'm definitely a creature of comfort when it comes to what I can put on my body. Like a 100% cotton Hanes thick shirt, that's just not the vibe that we're going for as a beach, outdoor lifestyle, athletic kind of brand. Yeah, you just weed out the stuff that I didn't like and came to stuff that I did like. Now we're making our own blanks, cut and sew, in a factory in Portugal, everything from scratch, which is nice. It took a long time to get there, but I guess that's the process, the creative process. Yeah.
Charles: (18:25)
When you first got going, were you conscious that you were trying to build a brand? Were you conscious that you wanted to create something that was three-dimensional from that standpoint?
Jesse Joeckel: (18:33)
Not at all. Never. It didn't really hit me until it started becoming popular, until I was walking around town or even out of town. I started seeing people in an airport wearing Whalebone in a different country. You're like, "Whoa! This is bigger than I thought." But no, I never... I think that's maybe a reason why I'm where I'm at now or the brand is where it's at. Because I never set out and be like, "I'm going to make this brand. This is how it's going to be." It just has happened so organically. It was never forced. It was never the be all end all. I think that is a huge reason why it's where it's at now. But yeah, no, I just was, "Hey, I could do this and I could live in this town that I want to live. I could surf, I could be at the beach with my friends." That kind of thing, when I'm young, 25, 26. That was my goal. My goal was to make enough money to survive the winter and have some startup capital each year. Because Montauk is a very seasonal town. You couldn't go through the winter and burn through all your money and then have nothing to start back up for the next season. Yeah, I just had small goals and happiness being a huge goal early on and just being able to live my life and not join… a lot of my friends straight off to New York City after college. I'm like, I just don't want to do that. I still don't want to do that. Not that there's anything wrong with that. It's just not me. I like being close to the beach, outdoors. Yeah, that was my goal. But goals change, two kids, wife later, definitely different goals now. But starting off, no, it was never like, "I'm starting this brand. It has to work and it's going to work this way.” Not at all.
Charles: (20:46)
It seems to me you've always had a very clear sense of how you wanted the business to show up, how you wanted the product to show up, and therefore I think as a consequence how you wanted the brand to show up. Is that true?
Jesse Joeckel: (20:55)
Yeah, I would agree with that for sure. Absolutely. Yeah. I don't know how much this has to do with it, but being from a very small town, you always… for me and my mindset is you always want to do things right. Even if whatever, regardless of the brand, growing up in a small town you always want to present yourself in the way that you want to be seen. That definitely transferred into the brand like, hey, this is how I want this brand to be seen. I don't want to be using, okay, you have great graphics and people love it, but your product's crap. That's not how you want to be seen. Just stuff like that. That's just probably my own personality, but yeah, that's definitely... with starting up that was...
Charles: (21:47)
What do you think is it about Whalebone that's made it so successful?
Jesse Joeckel: (21:53)
We have this little tagline that we use within our team, we say, "We're delightfully disoriented." We don't take ourselves too serious and where I think... obviously there's times where you need to be serious and put your head down and meet deadlines and all that. But for the most part we're very laid back, which is also, you don't want to be too laid back because then some people slack off. But just having a nice work environment, allowing people the freedom to, yeah, you don't have to be here 9 to 5 every day. It's just, I feel like that opens up the creativity to people and just doing fun things. All our issues are pretty out there, fun. We do a lot of fun topics for our issues, team field trips and all that. Keep it interesting and not so locked down and mundane.
But yeah. I guess the number one thing is just not taking yourself or life too seriously. We're not here for a long time, let's enjoy ourselves. I think that translates through the brand, I would hope. From my perspective that's what I hope it's putting out. Yeah, we're just trying to have fun while we're here.
Charles: (23:22)
There's a lot of trust involved in the way that you've built the business. You've always been really clear about the things that you love to do and the things that you would prefer other people to do because they're more expert in it and it's also not stuff that you're thrilled by. Has that level of trust always been natural to you? Have you always found it easy to lean into other people like that?
Jesse Joeckel: (23:41)
Maybe not. It might be a little learned. But it is tough at first to give up any sort of control in any aspect of the business.
I feel like I'm a really good judge of character, and I feel like I could read people really well. If I'm getting a bad vibe off of someone that works for me, maybe they aren't cut out for it. But yeah, if I'm bringing someone on I feel like before we even get to know each other really well, I'm pretty, I could read someone's energy pretty well, and if they're going to be good for what we're doing. Of course, hopefully they don't take themselves too seriously.
Charles: (24:31)
There's a really seasonal, cyclical aspect to your business, isn't there? From a creative standpoint, since you're the person who's always generating the ideas and the expression of the brand, does that make it easier for you or harder? Do you find that you are ramping up at certain points to get back into that mode, or is it always part of your day-to-day experience?
Jesse Joeckel: (24:50)
No, you're 100% right. I don't think naturally it is this way, but I've trained myself to be very seasonably creative. As some animals hibernate, my winter, I buckle down and I have hundreds of designs just all either sketched out or... I work in Illustrator. Just open documents and open documents and open documents in Illustrator of just ideas and stuff. I appreciate the fact that it is so seasonal. I mean, now not so much as it was, I have to be more on these days. But it is, winter time... fall, the busy-ness of our town and our retail shop and our sales, everything starts to slow down come end of September, October, into November. Pretty good chunk of time there where it's not as busy and I get to take a deep breath.
Fortunately living in New York, the waves are really good at that time of year so it's a really good time for me to clear my head. Then we go into holiday and we're pretty busy again through holidays, as far as online sales and promotions and stuff like that. Then after holiday, I get to just really hibernate with my family, my girls, and just… it's 20 degrees out in Montauk in December, January, and February. So I'm ramping up for summer season those three months, and then hopefully by spring we start receiving our product for the spring/summer busy season. But, people aren't meant to be on all the time. When we were roaming around, you weren't eating all the time.
Your body was trained to fast and relax and whatever at certain times. You're not up in the winter running around. People are less mobile. I think now, this day and age, =you're expected to be on every single day of the year. You can't show up to the office and be like, "Oh, I'm not really having a good day. I'm just going to chill." That's unacceptable. Whereas I'm like, what if you're just not having a good day? You can't force creativity. Say you work for a creative agency. It could be weeks where you're like, "I'm just not feeling motivated or I'm not creative." I could never do that, and that's why I could never... if something were to happen and this weren’t have work out how it's working out, yeah, maybe I'd jump on the fishing boat and do some creative work on the side.
I'm just not that. I have a creative eye. I could tell you, "Oh yeah, that looks good. That doesn't look good." But if I were to be sit down in a 9 to 5 and be like, "You have to create this this week and you have to create this this week," and have deadlines all the time, I just don't function that way. I can't force myself to be creative. I think this seasonality, it lets me slowly build up into my creativity, and then I start seeing a deadline a couple of weeks ahead, a month ahead, whatever. I will gradually get there, but yeah, I can't be forced. Which is, I don't know if that's common or not, but that's how I function.
Charles: (28:46)
What's your definition of happiness?
Jesse Joeckel: (28:49)
My definition of happiness is just having my family healthy, living in my small coastal town, showing up to work, turning the key, walking into a place that I call my own. I'm still in the same building, the same little fish market ice house that I was in since day one. That puts a smile on my face every time I go to work. Just, being able to make my own hours and not having people tell me what I need to do for my brand. It's my decision at the end of the day. Yeah, just providing for my girls, my wife, my two daughters. Yeah. It's happiness, being able to leave my house and walk down to the beach and catch a couple waves, let my wife catch a couple waves, take turns with the kids on the beach. That's happiness to me. Yeah.
I mean, it has nothing to do with money. Money doesn't hurt and having a brand that people like and support is great, but yeah, just being able to live a simple life. Yeah, I don't think we need to be going to the moon upwards and upwards and upwards. I'm happy where we're at, that's my happiness. I don't need bigger and more stores and this and that. I'm pretty content. I'm pretty easy to please. Yeah, if my girls are happy, I'm happy.
Charles: (30:46)
Do you have any regrets?
Jesse Joeckel: (30:47)
No. What's to regret? There's no point in looking back on anything. You got to live in the moment here, which I try and do every day. I've not been given anything but I have opportunities. Who would have expected Montauk to blow up in popularity as it has? We're in a small, empty coastal town that was busy for two months out of the year and now it's hundreds of thousands of people visiting every summer. If a handful of them walk into my store and make a couple of purchases, that's food on my plate. It may not be much but it's all we need and that's good enough for me.
Charles: (31:40)
How do you lead?
Jesse Joeckel: (31:43)
I want people to want to show up to work. I want people to want to, like I said, walk in and be like, "Oh, I'm happy to be here." Not dreading work. I want people to walk into my store and whether they buy something or not, walk away like, "Oh, that was really interesting. That's not your typical retail store. That guy was in there hand-printing t-shirts and putting them out on the shelves and we just bought one. It was still hot off the press." I want people to have an experience when they come into my store. I want people to... Montauk is a unique place. I want people to be like, "Oh, I got a very Montauk vibe off of this brand." That kind of thing. People are like, "Oh, what kind of brand is it?" I'm like, "It's many things to many people." There's no defined answer.
But if someone walks out of my store with a smile on their face and happy that they bought something, or happy that my retail employees were so nice to them and so helpful, and had a good experience, that's great. I had a funny talk with my wife's grandfather next door a minute ago. He brought me over just to show me a pair of shoes he bought, because he had such a great experience in the store, and the woman was so helpful. He's like, now he has his favorite piece of footwear. The whole time I'm over there I'm like, I hope one person a day walks out of my store, or seeing my brand, or picking up Whalebone Magazine, walks away and tells someone about it. To me that is success. I was impressed how into it he was and I'm like, if anybody feels that way about Whalebone as a brand we've succeeded.
Charles: (33:40)
And last question. What are you afraid of?
Jesse Joeckel: (33:44)
I don't know. Anything to prevent my picture of happiness, or my picture of success. I mean, nothing's going to last forever. I'm really enjoying this ride, if you will. Yeah, anything that takes that away. But obviously, if anything happens in life, you pick yourself up and move forward. But I'm really enjoying this, the trajectory we're on and just being able to provide for my family and hopefully put my girls through school one day. They seem to be very smart, so it's probably… hopefully they get some scholarships because it's not going to be cheap. Yeah, I mean, if you fail you fail, but I never want to look back and say I didn't try. I definitely give it my all every day, y’know pretty laid back. I like to take a couple days here and there, but no, I just... I don't know, just ride it out.
Charles: (34:58)
I want to thank you for joining me. I think that your definition of happiness is, in a world that is so complicated these days, I find it not just refreshing, but actually inspiring. I think it just takes so much of the noise away that fills people's lives up in some cases unnecessarily. I wish you nothing but success going forward.
Jesse Joeckel: (35:17)
Appreciate it. Thanks for having me.
Charles: (35:19)
My pleasure.
Jesse Joeckel: (35:19)
All right.
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