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How to Design Brands Worth Keeping in a Discount Driven World

A Prepathon 2025 closing session on building brands that outlast discounts, using emotional and social benefits and “lateral thinking” to create moments of wonder customers remember.

🎙️ Speakers
Christian Helms — Founder & Creative Director, Helms Workshop
Host: Matt Zambrio — Director, Organizational Development, DigitalOcean

✨ Key Takeaways
✦ Discounts fade, so build lasting emotional and social connection, not just functional benefits, like Yeti or Patagonia.
✦ Aim to “defy the trash can,” create work people keep and remember, literally and in their minds.
✦ Lateral thinking, coined by Edward de Bono, breaks linear logic to spark surprise and delight, and it’s a learnable skill.
✦ Use techniques like concept extraction (Howler Brothers), focus on constraints (Everlywell), and “what if?” (Kerbey Lane).
✦ Neural biases keep us on autopilot, so derail the expected path and insert the unexpected.
✦ Brand stories must be true and tied to a bigger purpose, communicated in a visually and verbally distinctive way.
✦ Instill play in your work and talk to people like humans, not demographics.

Matt Zambrio: Hi everyone, and we have our last session coming up for the day with Christian Helms, Founder and Creative Director at Helms Workshop, where they’re blending design and strategy to craft memorable brand experiences. He’s going to be presenting on “Defy the Trash Can, how to design brands worth keeping.” Hi, Christian, welcome.

Christian Helms: Thanks for having me. Are you guys able to see my screen?

Matt Zambrio: Not yet, we see you, not your screen.

Christian Helms: All right, let’s try that again then. How about now?

Matt Zambrio: Ah, perfect, looking forward to it.

Christian Helms: All right, beautiful, let’s jump in. So we’re all working to build campaigns and content and assets to promote our clients’ brands, but in the sea of noise out there, how do we cut through the clutter and actually make a lasting impact? Everybody’s running discounts during Black Friday and Cyber Monday, but the real question is, will customers remember you and your brand when the sales end? And the key to that is to really move beyond transactions and create lasting emotional connections. Transactions are not bad, that’s the goal, but we can do more, we can impact people in a more meaningful way.

And to start, we’ve got to go beyond hyping up the functional benefits of the brand, the key is to tap into richer benefits, the emotional and social benefits of your brand or product. The emotional benefits, how it makes someone feel about themselves to be aligned with your brand, the social benefits, what it says about them to other people to be carrying that brand flag. A great example is Yeti, very few people are carrying their Yeti into the wilderness to take down an elk or land a seven-foot marlin, but people want to be associated with that aspirational, adventurous, outdoor lifestyle and the level of quality that Yeti represents. You don’t want to walk into the party with an Arctic cooler, you want to walk in with a Yeti because it says something about you.

So that’s one of the things brands really need to do to win, and the question is how do you do it? Professionally, as a brand builder, the way I see the core of my job is creating moments of wonder, moments of surprise, delight, curiosity that can really lead to falling in love with a brand, and when we’re doing our best work, that’s the feeling we create for someone, and I love it, it’s my favorite thing. I want to create work that brings a spark of wonder to you, your baby, your goat, and whatever this guy is. And it can be delivered via something big like an environment or something smaller, whether it’s an aluminum can, apparel, a pint glass in a restaurant, a ridiculous animated GIF, or the world’s first 99-pack of beer, yes, that was a real thing.

I’ll talk a little bit more about it, but the goal for all of this sort of work is to defy the trash can, and I mean that in both a literal and a metaphorical way. So I want to create packaging that doesn’t get thrown away but gets reused as a constant reminder of branding. The Austin Beerworks cans you see here are a great example, we’ve seen them reused for everything from pin holders on a desk to planters for succulents and more. And the 99-pack even more so, this thing was over seven feet tall, it was on CNN, the Today Show, Good Morning America, Comedy Central, all the late-night shows, it made international news, and people still display them in their homes and in bars and everywhere in between.

In a metaphorical sense, I want brands that stick with you long after the purchase and the user experience, I want to defy the trash can in our minds, essentially where we throw that slew of info garbage that we process every day. So I guess the question then is, how do we do it, how do we defy the trash can? And one of the key ways is a concept called lateral thinking, it was coined by Edward de Bono. Lateral thinking is a problem-solving method that uses indirect and creative approaches to move beyond traditional step-by-step logic to generate ideas and unique solutions. So it’s the opposite of linear thinking, linear thinking is A leads to B leads to C, with lateral thinking, A leads to baseball leads to cantaloupe, which I know sounds ridiculous.

But this sort of thinking puts you in a place where, instead of staring head-on at the problem, you shift and are able to look at it a new angle, and that’s where creative solutions get really interesting, it’s the foundation for unexpected solutions that bring wonder, surprise, and delight. A great example from early in my career, I was tapped to create a bunch of editorial illustrations for Men’s Health magazine, and my first assignment was to build editorial illustrations for an article on erectile dysfunction, and I’m like, what do we do with this? So you would expect an anatomical diagram, an infographic breaking down what it’s all about. With lateral thinking, you get this, so that ran in Men’s Health, and see if I can get you to smile or laugh or share it with a buddy, or even better, want to be a part of it, it’s starting to work, right?

We all have these things called neurological biases, we recognize patterns, we learn cause and effect, the stove is hot, don’t touch it, the pitcher winds up, throws the pitch, catcher catches it, the ump makes a call, rinse and repeat. We learn these patterns, and these biases allow us to go along with our days without having to look at every moment and analyze what we’re seeing, hearing, and feeling to make sense of it. It’s one of the reasons babies sleep all the time, they are processing everything in the moment and it’s all new. These biases are rooted in the brain’s automatic unconscious processes, the hardwired neural shortcuts that allow the brain to make rapid judgments and decisions based on past experiences, emotions, affiliations, you name it.

Neural biases are really good for keeping us safe and productive, but when it comes to branding and marketing, they are absolutely the enemy. What we want to do is derail that train of thought and insert the unexpected, not like a comedian or a magician, we want to take people down a path and then sidestep from that path to create that moment of surprise and delight. Some of the key aspects of lateral thinking are exploring alternative perspectives, deliberately shifting attention to less obvious elements of a problem, using provocations, seemingly impossible statements to stimulate new thought, and accepting that creativity is a learnable skill, not just a natural talent, that’s something Edward de Bono really preaches.

So with linear thinking, you get IBM, International Business Machines, sure it’s descriptive but it’s not exactly sexy. With lateral thinking, you get stuff like Liquid Death, murder your thirst, much more compelling, much more provocative, much more interesting. So that’s lateral thinking, but how do we do it, and remember, it’s not a natural talent, it’s a learnable skill, and there are a host of techniques to switch our brains into lateral mode. I’ve been doing them so long, it’s just kind of the way I think at this point, I don’t even really notice it.

Some real-world examples from our work. First, Howler Brothers. Before Howler, outdoor clothing pretty much all looked the same, earth-tone colors, muted tones, and a real focus on promoting functional benefits, our fabric keeps you drier, we have better UV protection, that sort of stuff. So when we built Howler, we used a technique called concept extraction, the idea is to take successful ideas from completely different domains or industries and extract the underlying principles for application to your problem. With Howler, one of the brands we looked at was Icon, Icon is this really cool company that takes vintage Broncos and retrofits them with new engines, new technology, power windows, and a level of performance just like a new car.

So how could a concept like Icon apply to outdoor apparel? Howler came out with a completely different approach to outdoor apparel, outdoor clothing with character and personality and even humor, essentially a retro feel with modern performance just like Icon. People want to express themselves and be seen, people who are into the outdoors, and Howler really gave people that opportunity, and it grew a lot like Yeti. Very few Howler heads are planning a surf trip to a remote part of Costa Rica, but both brands are aspirational, people want to align themselves with that adventurous, exciting lifestyle and they want others to see it, again, the emotional and social benefits of the brand.

Another brand that we tapped lateral thinking for is a brand called Everlywell, the home medical testing brand. Their goal is to empower people to take control of their health journey, but guess what, the first few years, Everlywell focused on the functional benefits of the brand, our tests are more affordable, they get to you faster, we produce more accurate results, and the brand was pretty clinical, sterile and antiseptic, no real personality. But if the goal is to empower people, then where are the people in that story? There were none, it was just a typical healthcare brand. So we took a lateral approach to redefining the brand using a concept called focus on constraints. So instead of directly solving the problem, this is a technique that focuses on the roadblocks and limitations to understand what’s constricting the current approach, and then in a brand jiu-jitsu move, use those to your advantage.

So with home testing, what are the constraints, the tests are functional, they’re not sexy, if a person is buying one, they have a health concern, using the test is probably not a fun experience. But what if it was? What if the packaging was hip and cool and not just informative? What if it was avant-garde? If Everlywell was a fashion brand, what would it look like, heck, what if Everlywell was a lifestyle brand? Asking those questions positioned us with a different point of view, it gave license to elevate and humanize the brand. So now it’s not just faster, it’s a premium-tier product, it’s not just about results, it’s about the joy of knowing you’re in control of your well-being. If you look at five different health tests out there, Everlywell is the one that really defies the trash can. Now the business has to live up to the brand, we can make these big aspirational promises, but if the company doesn’t deliver on that promise, it’s a broken brand, so there has to be a gut check there.

Another example of lateral thinking in our work is a brand called Kerbey Lane. Kerbey Lane is a chain of all-day diners that has a special place in Austin’s culture, Austin, Texas being where we’re based, it’s been around forever and it caters to some of the city’s more unique and unconventional folks historically. But as Kerbey Lane grew, customers dwindled to a handful of regulars, and even though they had all of this equity in helping to build Austin culture, no one really knew about it, their brand identity didn’t express any of that, they really didn’t have a brand identity and Kerbey Lane wanted one, and they wanted families and kids and big groups looking to have fun.

So with Kerbey Lane, we used probably the easiest lateral technique to dip your toe into, called “what if?” And you ask this long slew of questions, what would Kerbey Lane look like if it was a movie, what would Kerbey Lane be if it was a vehicle, how would Kerbey Lane sound if it’s a song, what would it look like if it was a cartoon, what would the Kerbey Lane cartoon look like, how would it talk? Like this, right, it’s fun, it’s happy, it’s joyful, it would reflect the joy and enthusiasm that birthed the brand 40 years ago. I mean, these guys sent queso and chips to the moon with NASA, you got to talk about that, you got to celebrate it, you got to weave it into your brand fabric. And that essentially became the new brand, it relaunched about a year and a half ago, and people absolutely noticed immediately, at this point sales have skyrocketed and they’re opening a ton of new locations, it’s a huge win for them, all because of lateral thinking.

Big Swig is a sparkling water brand that started years ago and has since sold, that took a real lateral approach to flavors. We had jalapeno pineapple, chili mango, we had pickle flavor, very different than what anybody else was doing at the time. And when it came time to write ads for the brand, I got lateral in thinking, and one of the questions I asked was, what would eight-year-old me do with this brand? Now, background, as a fifth grader I was desperate to have a pair of Air Jordans, I was a huge Jordan fan, you can see them behind me if you can see me in the presentation, particularly the UNC blue ones, I was obsessed with these, they were kind of the holy grail, I wanted them so bad but it did not happen, though I asked a lot.

So thinking like eight-year-old me, I saw an opportunity, technically I completely manufactured an opportunity, and I’ll show you what that is. Boom, both Air Jordans into the spot, and they just happen to be my size. But how often do you get to reach back through time and essentially high-five eight-year-old you, that’s the stuff, and lateral thinking can create those opportunities. We also put a pig in the ad because pigs are cool and I liked them when I was a kid and they apparently love sparkling water, ignore the peanut butter you see there.

So if you’re paying attention, there are brilliant examples of lateral thinking all around us in the world. This is the freight elevator in Chelsea Market in New York City, it is an eight-foot square steel box that just goes up and down all day, that’s all it does, and the same guy has run it for years. He’s a baseball fan, and at some point he decided, I’m not going to stare at metal panels all day, what if this place was a gallery, what if it was the Hall of Fame? And so he got to work and completely changed it and turned this freight elevator into art. I’m really lucky I got a glimpse of this, I wasn’t supposed to see it, I just happened to get in there and it’s awesome, it’s a living document of the stuff this guy loves, it’s like this organic installation that just keeps growing and it’s absolutely beautiful. Through time and dedication and really simple, consistent craft and a little bit of lateral thinking, he turned this drab, uninspiring environment into his own little bubble of wonder, which really blew me away, lateral thinking takes you from elevator to gallery.

There’s some cool examples in art right now too. There’s a guy named Shawn Huckins, I don’t know if you guys know Shawn Huckins, he is absolutely an Instagram follow for sure. He paints these perfect, exquisite recreations of historic portraits, a lot of which hang in the White House or have at some point, and he paints them as if they’ve been hit by the eraser tool in Photoshop. Man, this is a perfect sweet spot for me, this combination of amazing technical prowess and lateral thinking with a really sharp point of view, the commentary is so good. Lateral thinking says, I’m going to paint these portraits and then I’m going to screw them up to make a statement, and he absolutely nails it, they’re even more amazing in person.

So when he got started originally, he would do these paint chip pieces, they’re about four feet tall and they have these people who appear to be looking out in nature or the world, set against like a paint chip you would get at Home Depot to figure out the color of your living room. I emailed him just to tell him how much I love the work and we started talking, and eventually, long story short, he made one for me. It started out based on a story about my brother and I that we exchanged emailing back and forth, and all of a sudden Shawn ran with it and got really lateral and turned it into basically a story of us being visited by aliens. So it is literally a painting of my brother and I drinking beer on top of a trailer being attacked by a spaceship, it’s one of those things that hangs in the agency, I don’t know if anybody else loves it, but for me I just adore it, I stare at it constantly, lateral thinking.

Well, it hangs in my home, I really try to find it and curate it and surround myself with it whenever possible, I try to keep it front of mind. A good example, this is my living room when it wasn’t being bombarded by a crazed, filthy, adorable kid, but it’s also proof that my wife is very loving and very tolerant, because over the fireplace is a four-foot-tall maniacal squirrel brushing his teeth, look at that dude. So this is a Swiss advertising poster and ad for Binaca from the 1940s, I think it’s probably the coolest poster or ad ever designed, this is everything I need, look at it, it’s insane. You could never sell toothpaste like this now, this weirdly and this beautifully, no one in the marketing department is going to sign off on this, it’s not going to happen, but it’s amazing, I wish you guys could see it in person, you would never forget it, but lateral thinking takes you from toothpaste to squirrel, it’s remarkable, and that’s what we’re shooting for, something remarkable, that’s what you want.

Another example out in the world. You would think there are some areas where lateral thinking just doesn’t apply, cartography for example, maps are maps, they are what they are, you can’t get creative with a map. But you guys know for years Google has undertaken this massive mapping exercise with Google Maps, Google Earth, Street View, all that stuff. So they were having trouble getting people out to this remote and challenging spot called Faroe Island, and they couldn’t map it, but lateral thinking essentially saved the day, Google strapped cameras to sheep on the island, and in a short time they had mapped every inch of the place. I encourage you to look it up and check it out, you can watch Sheep View on Google, it’s fantastic, that is some lateral thinking right there, that just makes me giddy.

And I think probably the most obvious place that lateral thinking shows up is in play, kids are innately lateral thinkers. This is my son Hatley, and he’s the constant reminder of the power and wonder of lateral thinking for me. Watching the world through his eyes is amazing, you guys have kids, you know this, it’s a cliche because it’s universally true, as he learns and grows, I re-experience all of these different moments, but I get to learn them and view them through a completely different lens off to the side, for the first time with no preconceptions. What if, look at that, why, look what I did, it’s all hilarious and it’s lateral thinking and they just do it innately, and if we’re smart enough to listen and pay attention, they really have it figured out.

They can teach you everything about lateral thinking or just wild unfiltered creativity, whether it’s music or travel, photography or food, misdemeanor vandalism, it’s all there, they just innately have the wonder and freedom and simple appreciation for life, that headspace that we spend our time as adults trying to get back. So a few years back I wondered what would happen if I let Hatley art-direct his Mother’s Day card. So this is me at the Macintosh, him playing full-on hovering art director, I can’t make any decisions, he just tells me what to do, and when that happens, you get Hatley, you get Papa, you get Scatter, that’s a dog, it’s kind of a dog, it’s our kind of a dog, that’s ours, you get Chewbacca, now we’re cooking, that’s pretty unexpected, Scatter gets a lightsaber and then little brother becomes Baby Yoda and he nailed it, I guarantee no other mom got this card that year, I never could have come up with it, it’s brilliant and wild and 100% him.

So lateral thinking is everywhere if you’re tuned into it, and some of our most celebrated entrepreneurs utilize it, Steve Jobs, Jeff Bezos, the list goes on and on. Anthony Bourdain used it to change the way we think about food and travel, Anna Wintour changed fashion with lateral thinking, and if you’ve ever listened to Tyler, the Creator, you’ve heard lateral thinking in real time. And again, it’s a learnable skill, so I really encourage you guys as we’re creating all this content to try it out for yourselves, it’ll create content that amuses other people and it’ll amuse you while you’re doing it. I could talk forever about this, but I’m excited for some Q&A, so thank you all a bunch.

Matt Zambrio: So, Christian, that was fantastic, I really enjoyed that. Thank you for sharing what I consider to be some pretty personal moments with you and your family and connecting them to this concept, as somebody with a young kid myself, it really touched me a little bit, seeing them grow up and going through those experiences. So we do have a couple questions from the audience. First is, which brand stories survive the trash can test, what narrative makes a customer keep the package or follow the brand post-purchase?

Christian Helms: Yeah, absolutely. First, it’s got to be true, it can’t be fabricated, people see through that at this point, and it’s got to again hit those emotional and social benefits beyond just the functional benefits. So Apple is a great example, people will pay 2x for a phone because it’s an Apple phone, they’ll buy an Apple computer because it’s think different, it’s all of this amazing content that Wieden and Kennedy have made over the years to inspire you to align with that brand, I’m an Apple guy, I’m not an IBM guy, that’s not cool, but an Apple is cool. I think Patagonia is a great example as well, a brand that stands for something bigger and tells you not to buy their products, it’s brilliant, that’s about as lateral as you can get. And the list goes on and on, but if it’s true and it resonates to a bigger purpose or a bigger idea and is communicated in a way that’s visually and verbally compelling and unique, it can go a long way.

Matt Zambrio: No, I totally agree with you, and I’ll add to the list, I’m a big Allbirds fan, I think it started from that tech space, and however long later I’m still stuck six years continuing to buy them and just love the brand, so totally resonates with me. Next question, do you have a checklist or a model that you use for this?

Christian Helms: You know, I don’t anymore, but Edward de Bono actually wrote a book called The Thinking Course that runs you through everything I talked about and 30 more ways to do it, it’s great and it’s very readable. I recommend it to creatives all the time, because when you’re early in your career, it’s hard to get out of linear thinking, so you need to eventually find ways to trick your brain into being lateral. The more you do it, it’s just like exercising a muscle, it gets easier and easier, I don’t even really think about it now, the studio would get sick of me saying, make it weirder, and that’s exactly what I mean, it’s like, yeah, that’s a great solution, but how do we tweak it a little bit?

Early in my career I did a lot of music industry work and I worked with a band called Modest Mouse and spent a week living with Isaac, the lead singer, working on the packaging for an album. And he said his thing was always, I write a really beautiful song and then I try to find little ways to mess it up, and that can be a good thing, the little mistakes, the little quirks, the amp feedback in a White Stripes song at just the right time can make it even better, because it’s real and it’s human.

Matt Zambrio: Yeah, no, that’s great, going back to the childhood thing, my daughter watches one of these Ada scientists, I think they call it happy mistakes, these things that just work out and make it better for us, so it’s about appreciating these and acknowledging them for what they are and how these make great moments for us all.

Christian Helms: 100%.

Matt Zambrio: So we don’t have any other questions it looks like from the audience, but Christian, I do want to ask, any kind of final thoughts, and what’s your feedback from Prepathon for the audience?

Christian Helms: Yeah, I would say, just to reinforce what I was talking about, try to instill an element of play in your work, if you have fun doing the work, people feel that, people feel that energy transfer. And talk to people like they’re humans and not marketing sectors and demographics, talk to people like people talk, that can go a long way.

Matt Zambrio: No, I love that, fantastic, I really agree with you about that as well, I think it helps resonate with your audience also.

Christian Helms: Absolutely.

Matt Zambrio: No, Christian, thank you so much for your time today and thank you for the presentation and sharing your thoughts around this topic, I thought it was very insightful for myself as well, even though I’m not in the design space, but it’s something I think regardless you can apply to the work that we do every day.

Christian Helms: That’s great to hear, thank you, Matt, my pleasure.

Matt Zambrio: Have a great rest of your day, Christian.

Christian Helms: You too, bye y’all.

Matt Zambrio: All right, so I think that takes us through our last presentation for the day. I want to thank you all for joining day two of Prepathon, we had an amazing day full of great sessions, panel discussions, and even some tricky questions. As a reminder, don’t forget to submit the survival challenge. I also have a couple shoutouts from today’s presenters, James Kemp opened with an insightful panel discussion, Sonia shared powerful insights on AI and e-commerce, Paul delivered a strong, impactful presentation as always, and then Christian Helms, as we just saw, closed with that inspiring session on branding. Tomorrow we have one more day left at Prepathon that will be packed with expert insights just like today and yesterday, tomorrow’s sessions will include topics focused on personal branding and valuing older customers. Also, we’ll be announcing the winners of the Amazon gift card tomorrow, please continue to stay engaged to maximize your chances. Thank you again for being a part of Prepathon, and we hope you’ll join us tomorrow for the final day, until then, take care and goodbye.