The Unofficial Shopify Podcast: Entrepreneur Tales

How Chubbies Built a Menswear Movement

Episode Summary

w/ Preston Rutherford, Chubbies Shorts

Episode Notes

"We were the luckiest people in the world to be able to do this stuff."

Full Video Interview on YouTube: https://youtu.be/fEUf9MTXk4c

This week, I'm joined by Preston Rutherford, co-founder of the Chubbies Shorts empire that's been redefining men's fashion with a splash of retro and an avalanche of fun since 2011. Preston, a Stanford grad with a knack for spotting gaps in the fashion world, shares how a simple idea of retro shorts spiraled into a nationwide trend.

Preston walks us through the early days of selling shorts right out of a backpack, the evolution of Chubbies' identity, and the power of community in brand building. But it's not all smooth sailing. Preston gets real about the challenges of seasonality in fashion, the pitfalls of over-reliance on direct response marketing, and the emotional rollercoaster of building and selling a brand.

So, slip into your favorite shorts, whether it’s the weekend or not, and let's get down to business with Preston Rutherford’s insights. Don’t forget to subscribe for more stories like this.

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Episode Transcription

Heads up friends, the unofficial Shopify podcast is made by indie entrepreneurs for indie entrepreneurs and may contain material not suitable for all audiences, like swearing or economics.

Listener discretion is advised. (upbeat music) Today on the unofficial Shopify podcast, I am thrilled to be able to interview the co-founder of a brand that was one of my darlings.

One of those online stores, you should have a few, that there's like a portfolio of brands that you love because they inspire you, they excite you, they energize you.

And for a while, and if you listened to the show years ago, you know those chubby shorts.

Man, I love chubby shorts.

I was resistant to even wearing shorts and chubbies got me wearing not just shorts, but short shorts, just the wildest stuff.

And then they started buying the shirts.

And I don't know, the brand is so fun.

It is so fun.

And I love the tone and the vibe and there's like a retro undertone to it that I just greatly enjoyed.

And so I'm thrilled today to be joined by Preston Rutherford.

But this, before I forget, this is the unofficial Shopify podcast and I'm your host Kurt Elster. - Check nasty. - Preston, welcome.

I'm thrilled to have you here. - Yeah, Kurt, thank you.

I'm honored to be here.

I think it should be a bunch of fun, big fan.

And thank you so much for the kind words.

Really appreciate it.

And thank you for being a customer, most importantly. - I did, I was not gifted anything.

I paid for all of it.

I had several pairs of shorts, the shirts.

To this day, the item that I still love that has held up just phenomenally.

So these fleece crewnecks that are like the most outrageous colors you could come up with. - Yeah, oh, that's awesome that you have those.

Those are awesome.

But yeah, that's sort of like a deep cut.

So I'm impressed.

You not only have done the sort of like first purchase drivers, but you've gone deep on the customer journey.

So thank you. - Yeah, somehow I ended up in your ideal customer profile and now we're here.

So how long ago was that?

When did you co-found Chubbies? - Late 2011 and let's say officially launched early 2012.

So it's been a really long time.

Yeah. - What does that first implementation of it look like?

Was it different than today?

Or like you just said, we should sell short shorts to men and then bam money? - Maybe some version of that, but to your point on implementation and was there sort of a big pivot?

No, I mean, to your point, it was just like, the state of men's fashion was in disarray in our opinion.

And not that we were fashion experts or anything, but just as consumers, we just sort of thought there's a product we would love and we couldn't find it.

And we loved to your point, the retro vibe and the look of the photos that we had of our dads on spring break or whatever they were doing with their proper length men's shorts looking awesome.

The big sideburns, the mustaches, whatever it was.

And so it just felt like there was something there that needed to be brought back, that needed to be brought to the world and was totally missing.

So that initial thinking and approach continues to this day, although today it's a little bit broader, but yeah, it was so funny.

Now to your point about sort of like waking up one morning and being sort of like in a bed of dollar bills.

No, it was more the idea that, we started really, really small, made the product for ourselves, made the product for five of our friends, made product for 10 friends.

So it was very, very small, very incremental, started with in-person selling before we even went on to Shopify.

So yeah, it took a while and we were still working our day jobs for quite some time, a long time actually.

So yeah, but the core of it to your original point was always there. - This started as you're seeking out this retro look and then today it's a nationwide brand, it's in retail stores.

I swear I've seen Chubbies retail stores like actual Chubbies branded stores. - Yep. - Is that the case? - Yes to all, yes. - Amazing.

How many retail locations are you in? - That's a great question.

I actually don't know the latest number, but we went through a journey just on the retail stores front, just trying to be helpful to the listeners of just trying to test 'cause it's one of those things that can be kind of scary, especially when you don't really have experience or the let's call it folks who have done physical stores before.

So we started really, really small, super flexible leases paid up to be able to have that flexibility, kept the build-outs extremely inexpensive and learned a ton.

And obviously COVID was very tough on stores.

So there was a process of having to close them, fortunately, but today I think in general, the approach and the process is much more find the best locations we can, do an actual legitimate build-out.

And I think doing those things, like reaping the benefits, but yeah, I mean, I think broadly to your point, it is sort of like a fully omni-channel strategy.

And as you build that brand, you are able to, let's call it more successfully penetrate all of those channels, but yes, Shopify, retail, stores, Amazon.

So across the board, yeah. - I really, I missed the most important thing here, the name, where did the name Chubbies come from?

I think mostly the podcast externally facing answer is that it's sort of like completely irreverent, excuse me, and ridiculous.

So the idea is like, why would you, as a professional human businessman, who's an adult name a company Chubbies?

And so first of all, that's ridiculous because fundamentally the premise of our business was to just try to be the opposite of the serious, no fun, exclusive status quo in men's fashion.

So it was just one of the most impactful ways to bring fun, levity, and just not taking ourselves too seriously to the world.

And it's a great manifestation of that, at least in our opinion.

And to be totally candid for multiple times throughout the business, at least I can't speak for my other co-founders or people in the business, but I wondered, was this a dumb decision to name our business this?

Have we limited our potential upside?

And so it's one of those things where it's kind of like pros and cons for sure.

And I think ultimately I look back and yeah, I mean, it allowed us to get that initial spark, that initial differentiation that stood out, that allowed us to get that initial foothold that even gave us the opportunity to grow beyond that.

But the other things that we kind of talk about, one is just the general idea that it came prebuilt with an elastic waistband.

So that if you eat a big meal, feel a little chubby or aren't able to get to the gym for a while, the shorts will stay with you.

And so even as you get a little chubby, it doesn't matter, right?

And again, that was really consistent with our vibe in getting started.

Like one of our, let's call it enemies from a brand perspective was the 2011 manifestation of Abercrombie & Fitch where you had to have a six pack in order to be a part of the club.

You had to look a certain way.

And if you were a normal person, you didn't feel invited to the party.

You didn't feel included.

And our whole thought was that's ridiculous.

Let's just sort of like be who we are.

And if you have the six pack, amazing.

If you don't, who cares?

It doesn't mean you can't have fun and can't be a part of celebrating the freedom of the weekend and all the sort of like awesome experiences that the weekend provides, which is what we built our brand around.

So yeah, I mean, it's kind of all of those themes.

And I won't say it, but I will say that others have said that it is also sort of like a term for a human body part. - I'm not familiar. - That in and of, yeah, me neither.

I have no idea what they're talking about, but they have said it.

So I just thought, you know, for the listeners, I would pass it along. - Yeah, just watch out in case someone tries to convince you of this dirty lie.

So you mentioned that the brand name being like unexpected, a little potentially outrageous, helps get some early buzz.

What else helped you create buzz around the brand?

What strategy did you use to get that initial traction? - I mean, it's sort of like one of those funny, kind of like trite terms, but like local grassroots marketing was sort of like the initial initial meaning.

No, we had four founders.

So a big part of the story, the vibe, the identity of the brand is this idea of community.

And I think we'll talk about that, but just like having fun with the people you love, creating memories in person with the people you love, celebrating the weekend.

So that's exactly what we did, but that's, and that's exactly who we were and who we are.

So it was the four founders and our friends, let's call it 10 other friends, or some derivation of that number, just doing the normal things that we would do on the weekend, living in San Francisco, being 25 years old, you know?

So going to brunch, going to throw Frisbee at the park, just doing all of these basic things that you do when you're recently out of college and ideas that we were wearing the product.

And at that time, and still to this day, yes, we have sort of like the more muted colors, but you couple a short that is, let's call it four or five inches shorter than everything else that's out there with neon pink, green, and orange.

And you have something that stands out that is immediately noticeable, that is something to talk about and to look at.

So people would come up to us.

Yeah, yeah, exactly.

Yeah, people would come up to us and they'd ask us and they'd either say they hate it or they like it.

But some people, the majority of people would say, "Where do you get those?

I want those."

And we had them in our backpacks.

And I feel so old saying this 'cause it was pre Venmo, Square Cash, whatever, whatever, but the Square card reader had just come out.

So we could actually take credit card transactions on our phone, pull out a pair of shorts from our backpack, hand it over, and we were in business.

So that was one of the first pieces. - Hey, where did you get those shorts?

A man in San Francisco sold them to me out of his backpack. - Yes, yes, exactly, exactly.

Effectively, yeah, door-to-door sales of men's tiny shorts is how we got started. - Yeah, when you phrase it like that, it's a pretty wild story.

So how, I mean, 12 years have passed since then.

How has the Chubby's identity and messaging evolved with growth? - Great question.

So the way I think about it is two parts, right?

There's the core and then there's sort of like what surrounds the core.

The core doesn't change, the surroundings evolve.

And so the core is and has always been the idea of the weekend being the thing around which we orient and what that represents being the story.

And then being able to talk clearly around what it doesn't represent as a way to sort of like solidify and codify what it is.

But, okay, so what does it mean?

I mean, it's the weekend.

So then what does the weekend stand for in our lives?

It stands for freedom, it stands for fun, it stands for the opposite of the work week where you are not in control of your time, where you are reporting to someone else, where you are acting like a quote unquote professional, where you have to, where you're sort of like subverting your true self in a lot of ways.

It is the opposite of that.

It is freedom, it is where you are in control of your time.

It is where you are having fun with the people you love.

So that was the whole idea that we wanted to capture because we graduated college in 2008, global financial crisis, stress.

I mean, it was just hard to find a job.

Unemployment was, it wasn't depression levels, of course, but it was pretty material, especially for folks coming right out of school.

And just like incorrect assumptions that, well, shoot, I went to Stanford, I should be able to at least get a job.

I couldn't, I couldn't even get a job.

I had to beg a friend who I lived with in college to have me come on as a, starting as an unpaid intern, to just sort of like have something to do during the day.

So it was very stressful.

It was very much like, oh, who am I?

What is my role in this world?

Am I capable?

Am I enough?

I should be doing all of these great grand things that I see other people either have done that are older than me, et cetera, et cetera.

So very much, we were a response and a reaction and a release from this stress and tension and mental weight that was on a lot of us in that sort of like age band around that time.

Then to the second part of the question, like how has it evolved?

I mean, I think in a lot of ways, I can only speak for myself, the other three founders, and then the whole team are amazing, way smarter, way better at any of this than I am, exceptional people who took the brand to a place that I could have never have imagined.

But just to kind of speak for myself, there's no way I could have marketed or create a brand that wasn't just basically for me.

There are some people out there who can just be like, oh, I'm gonna just figure out how to create a brand for customer that is not me, but they're able to do it.

I can do it.

So basically the evolution of the brand, the messaging of the brand, the positioning, et cetera, et cetera, not changing the core, but again, the surroundings, the takeaway is it just sort of like evolved with the stuff that we cared about, that we thought was funny, that was our life.

So we started the business.

It was much more, you think about the photos we were taking, the content we were putting out, it was very much being a single guy and figuring out life and doing the things that you generally do as a single guy.

Let's call it fast forward a decade and it's much more families.

It's family trips.

It's doing things and dressing, matching with your family, with your kid, teaching them how to do stuff, like hanging out in the backyard, but it's still, the core hasn't changed.

It's just an evolution.

And I think our customer base, there's this idea of a group that grew up with us, but then because the core didn't change, you were still getting sort of like new people who were maybe younger than us still coming into the brand because of ideally the fact that everything that we were doing was aspirational from whatever perspective that we tried to make it sort of like authentically aspirational because it always came back to the core.

This idea of freedom and authentic confidence and fun and being welcoming and not taking yourself too seriously, all of these things are aspirational.

You're 12 years old, 55 years old and everywhere in between, right?

And so I think that's why, that's how it evolved, but I think that's how it still worked and I think continues to work. - Today's episode is sponsored in part by IntelliGems, the game-changing A/B testing tool for Shopify merchants aiming for peak profitability.

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There is a sense of community and being on the receiving end of the marketing and an ideal customer.

I always had the sense that there was a community aspect to Chubby's marketing and branding.

I assume you think that's the case, but what were the marketing tactics that let you connect with your audience that cultivated a community? - I mean, it started, that's how it started.

That's how we viewed everything that we did.

So what do I mean by that?

As I mentioned before, it started, you know, we were just making product for our friends.

Like the four founders, we are best friends.

We, I think, have such an amazing relationship.

Not that everything was sunshine and rainbows forever, but the level of love and respect that we have for them, for each other, is, I mean, such a gift, such a blessing, but it just emanates from there.

And then you've got sort of like your core group of friends around that community, right?

Authentic friendships, relationships, and everything that that means.

So what do I mean by that?

So in my opinion, like brand building, community building, right, is just authentic relationship building, right?

It's all of the basics of why you have a best friend and the components of that relationship and how it builds over time, how it's all about built trust, showing up, being consistent, giving more than receiving, all of these very basic, obvious things, but those served as the foundation.

And then as we grew, as we were no longer, as people were buying from us that we had never directly met friends of friends, friends of friends, whatever it might be, the premise of what we were trying to do never changed.

And the way I like to talk about it is that, and again, this might seem kind of trite, but then when you actually think about how it manifests in tactics, which is your question, it's different.

So rather than being a company or a corporate entity, selling goods and services to faceless customers, we always viewed ourselves as a group of friends, making the coolest thing we possibly could for our friends.

And that whole idea, how does that manifest?

So that manifests in actually treating people like your friends, caring about them, trying to make them feel like they're heroes.

I mean, I think one of the big things that we did, call it the Chubster Nation, but this was our community of folks who would send in user generated content.

But UGC is just such like a weird term.

It was just the same way that you send a photo to your buddies on your friend's text thread.

And how we framed a lot of what we did is just how much fun we all had on our friend text threads or email threads, where we would just go back and forth, ribbon on each other, sending funny content, et cetera, et cetera.

That drove everything else.

And it manifested, I think, in content that we all could resonate with, that we all enjoyed.

And then when that stuff would start coming in, in the same way that we would respond to our buddies with authentic responses, whether it be sarcastic or let's just call it more admirational or whatever it might be, we did the same thing to our friends of friends of friends.

And then we just had a bigger platform where it was on Facebook at the time, like pre Instagram.

And then it was on Instagram, where you could then make them feel like superheroes when you post a picture of them and you write this cool, funny, made up backstory about the story behind the photo.

And then they share it with their friends and they feel awesome.

And we feel awesome being able to help them feel awesome.

It's just this really cool thing.

But I guess the non-obvious part of it from a tactics perspective is it might be perceived as a massive over-investment of time, money, resources, people on this sort of thing.

Like a founder, myself or Tom or Mason or some of our other just amazing people, Phil, blah, blah, blah.

So many people would spend a lot of time writing this caption.

Whereas you'd be like, that doesn't make sense.

Why are you investing so heavily in something like this?

But it's because we viewed this community building as this feeling that you get being a part of this community that is then immediately associated with this purchase of a product, right?

That is way more expensive than a random pair of shorts you can get at Walmart or whatever.

But the feeling that you get when you throw these things on, when you buy from us, when you receive that awesome blue box that we used to send with every order, that feeling that you get by being a part of this friend group was special.

So that's why we decided to over-invest and have founders and our best talent doing these little micro things that could seem way too insignificant and don't scale.

But I think like in the story of Airbnb, or Y Combinator generally, do things that don't scale.

We didn't only do that at the beginning, we did that forever.

And the results, the outsized, I think, results from the salience and strength and resilience of being a part, being a Chubbies purchaser, a Chubbies customer.

And it's kind of like how you wave to other people if you have a Jeep sort of thing.

Like there's that community where you're just like, why am I waving at this person that has the same brand of car that I have?

Like, it just makes no sense, but you're a part of something.

And it's crazy, but it feels awesome.

And so we do it as humans, 'cause it's sort of like a fundamental need.

And so the people and brands who have tapped into that, I think, benefit greatly, but it takes a lot of time.

It takes like seemingly crazy overinvestments in weird areas.

So yeah, I mean, those are some of the thoughts on it.

Tactics, you know, I talked about writing crazy stories about people who had sent in photos and posting them from our account.

So I mean, that's one really kind of small thing, but just the general idea of what are all of the tactics and strategies that we can employ that are around this idea of making our customers feel like the hero?

The total hero. - I love this approach.

I think it gets harder as the brands scale.

It has to. - Maybe. - I think a lot of people maybe start with these things that don't scale, but then the brand scales and they stop doing them.

So, but in your case, this is so core to the brand's essence.

How do you maintain those activities, that brand essence as it scales?

Or was it just because you saw the importance it was baked in and you're like, that's just, that's the SOP, that's what we keep doing. - The latter, yes.

And it was a realization of what our core competencies truly were and are.

There are some things that just won't determine the success or failure of what we're doing.

You know, nailing pick, pack, and ship on the fulfillment side, essential, important, but not core competency.

So you invest there, don't necessarily over-invest.

You try to pay as little as possible.

You want it to be the smallest portion of your, not smallest portion of your P&L, but you want to drive it to be as low as possible and still get that customer expectation.

But with this small set of things that we truly viewed as our differentiators, as the reason why we go from what could be viewed as a complete commodity, something you'd pay ordinarily like four bucks for on Amazon, like a tiny pair of shorts, like where you start having the rational thought, why am I paying this much for this little fabric, right?

Which is questions we sometimes drive compared to other shorts.

These are half the length of my normal shorts, so why wouldn't I pay half as much, right?

Yeah, you know. - I don't sell them by inseam length. (laughing) - I mean, yes, of course, I agree, but we do get these questions, or did.

But yeah, so I think that just the general idea was, what are your core competencies?

If you do these things well, what will provide the, what will maximize the opportunity of massive growth, whatever it might be, the success we want?

So that was the key.

And that's why we're such proponents of brand and brand content, of having as much of that happening in-house as possible, controversial maybe, and not that we never used external resources at all, but trying to have a, because our whole thesis is that shots on goal or velocity of content with an objective feedback loop is the only way to actually kind of like create a brand that can scale.

Yes, of course you can do like the Dollar Shave Club-esque, amazing single video that just dominates.

That's very much a binary outcome from a probability weighted success bet perspective, which just kind of felt like that's not a risk we can take.

We didn't raise that much money.

We raised very little money.

And so we just didn't have, we couldn't make that math work out.

So that's kind of how we approach things. - If you, I've heard about a lot of success here, a lot of wins.

I know it's a successful brand.

Give me an L, like where have you made a big oops, a significant misstep? - You know, shorts business, super seasonal.

Seasonality is very difficult on your P&L, on your cash position.

You gotta be making your biggest investments when you have the least amount of cash, which is crazy, right?

'Cause you got a fun spring and summer when you're kind of crapping the bed in fall/winter.

And it's stressful.

It's stressful.

It's hard.

The more like every fall and winter, your morale just sort of like plummets 'cause you just, your numbers are down.

You're like, what am I doing?

So that's the background context.

So we're like, we gotta beat seasonality.

So the way we did it, this early approach that, it's just so funny.

We made wool shorts, dry clean only.

We didn't tell our customers that they were dry clean only.

So luckily we made a small run, but pictures that we got back of them shrinking to be the size that might fit a two-year-old was just hilarious.

But it was just sort of like, early mistakes that you made, you're just like, what in the world?

And I think the care label said dry clean only, but who reads the care label if someone's not like hitting you over the head, telling you, because none of our other products were dry clean only.

So I think that was one of the funny, more funny mistakes, losses, et cetera.

I think the biggest L in my world, which was just sort of like, marketing, advertising, content, growing the brand was for a long time, we got into this world of over-reliance on sort of like hyper-measurable bottom funnel, direct response, demand harvesting, because we were super data-driven, gotta be data-driven, gotta be objective.

That's the only way to make sure you're not wasting money.

So I think we almost optimized ourself out of business.

You know, I mean, and speaking, and maybe sort of like going full circle on the name Chubbies, and at least my questioning about whether that was a dumb name, we had trouble raising additional equity.

So we raised a little bit of venture capital, raised a little bit from friends and family, but because we got to a place where we weren't at least on a percentage basis, growing as fast, we couldn't raise additional venture capital.

So then we couldn't keep funding, you know, the Facebook machine, now the Meta machine.

And we didn't really have our P&L house in order.

And you know, we were just losing money.

And the business wasn't architected around things like contribution, around things like driving the organic side of the business.

It was very much just let's tweak all the knobs.

So I think that was a big L that we learned a lot about, and that I try to talk a lot about in my writings on LinkedIn, because I know a lot of people are in it, or they haven't yet felt the pain that we felt, but they're maybe starting to feel inklings of it, where, you know, you just feel like the resilience of your business is kind of like at risk, or ad deliverability stops for a day or a week or whatever, maybe because you didn't pay your bill on time, or the card got declined, and your business just like completely plummets without this daily sort of like, whatever, your ASC campaign or whatever running.

So that was a big L, but we, over a course of many years, evolved it into, I think, what then became our biggest W, which was just figuring out how to do effective brand building, you know, brand building in a way where it's tangibly connecting to financial results, manifesting in increases in revenue coming from own organic traffic sources, you know, and the retail side, like faster sell through at all red price, you know, all those sorts of things that represent more profitable, resilient growth.

So I like to tell that story because it's sort of like the biggest L turning into the biggest W. - Hey, Shopify sellers, listen up.

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Eventually, in 10 years of success, Chubbies gets acquired.

Tell me about that. - One of those just, you know, failed, let's say multiple times trying to get to some sort of transaction in years before.

Of course, it's maybe easy to talk about from this perspective after having done it.

So whatever, take it as a grain of salt.

But my biggest lessons from the experience are I kind of treated it as that was the goal.

And I ended up having a lot of burnout, unhappiness, tension, stress in life because of that rather than just sort of like enjoying the work.

Doing something I thought was super meaningful with the people I loved and working my butt off doing it, that's what I later learned.

That is the win.

That is, 'cause I was lost, you know?

I was lost after the acquisition sort of thing.

No longer in the business.

What do I have?

What am I doing?

Kind of depressed even.

So it's like one of those things where it's just like it seems so amazing on the surface.

And don't get me wrong, amazing, so blessed.

But there's something to be said about just the reality that it is truly about the journey.

And I don't wanna sound like, I don't know, like a Tony Robbins-y or like a quote you find on whatever, inspirationalquotes.com or whatever.

But I don't know, just having lived it, it's like true.

So to the extent it's helpful to put that out there, that's great.

But the experience, which was the specific question you asked, I mean, was amazing.

I mean, we, like a whirlwind and, you know, just kind of felt like everything fell into place.

Like super grateful because as you know, with a startup, you're not really paying yourself much.

You know, you're not really paying yourself at all.

I mean, when we started Chubbies, I had my own bedroom in a place where five or six other guys lived.

But to save money, I moved out of my bedroom and into my friend's bedroom.

We lived right down the hall and I didn't even have a bed.

I slept on a bean bag.

So it was just like this existence of crazy cost consciousness, et cetera, et cetera, which is fun.

You know, you just kind of look back on it.

You're like, that was amazing.

That was so cool.

But it was a crazy ride, right?

I mean, you go from thinking the value of your equity is like worth something, and then something changes that you completely don't control just like the acquisition environment, comps.

And you're like, well, okay, yesterday, my equity was worth X.

Now it's worth one fourth of X.

Nothing changed.

Nothing in my business changed, but I have now become materially less on paper wealthy or whatever that, you know, whatever it might be.

It's just one of those crazy journeys where it's just sort of like-- - Does that mess with your self image? - Completely.

I mean, for me, it did.

I can't speak for anyone else, but, and I'm somewhat embarrassed to say that, but yes, absolutely.

Because, I mean, you've got your friends, they're going out and doing all these other things, especially if they're like in finance or, you know, whatever, cash heavy comp situation.

And we're just like, well, I think, you know, we're doing it for the equity, we're doing it for the longterm.

We're also doing it just 'cause we love doing it.

And I, you know, kind of feel, maybe I made a mistake.

Maybe I'm not good enough.

Maybe I don't, I don't know. - That's a posture syndrome. - What if this doesn't turn out?

Yeah, it's crazy, totally.

So, yes, it was difficult for me.

And, you know, I wish-- - I don't think your story is unusual.

I don't.

I've talked to other people that are like in just leading these incredible companies and doing these incredible things and incredible opportunities.

And turns out all of us will compare ourselves to the highlight reel of, you know, our peers.

And then go, oh, maybe I'm not good enough.

Maybe I don't know what I'm doing.

I think we all have those moments.

So, you know, I'm sure it's refreshing for someone to hear that they're not alone in this. - Hopefully, that's a crazy journey. - The other thing is we're coming to the end of our time together that I really, I want to touch on is there's another company that was born out of chubbies and it's Loop Returns.

Loop Returns sponsored our podcast for a year.

Thank you.

How did that happen?

How did you spin a SaaS app out of a short store? - Who knows?

Who knows?

I mean, totally crazy.

It is as a result of no, nothing that I did.

But the general idea is that, I mean, I'm being somewhat facetious there.

General idea is that we had, if anyone was operating a brand, let's call it 14, 15, 16, returns and exchanges sucked.

So painful, so inefficient, not just for the company, most importantly for the customer.

But for the company, tons of CX tickets, unnecessary back and forth, manual like return label, PDF creation, attachment to email, like all of this crazy stuff.

And then on the P&L for the company, so many returns could have been exchanges.

So, and again, it all goes back to the customer experience being suboptimal, where they're trying to accomplish a goal that they're unable to accomplish.

And they're waiting way too long.

So we just thought, we had a habit, we're just a bunch of nerds at Chubbies and we like technology, we like building software to solve problems, I don't know, just seems cool.

And so we had a habit of doing that.

This was just one of the things that we built that happened to be touching on a nerve that other people were feeling, touching a need that other people were feeling.

And a lot of the tools we built internally, software built internally was like internal facing or less obviously differentiated as an individual product.

But this just happened to be like a standalone thing that was meeting a need.

And so we originally built it just as an internal tool to serve our customers.

And other brands came to us and said, hey, we have the same problem, can we use, where'd you get that?

And it was like, oh, we made it.

So it was very much of like an organic, not thought out sort of situation, but we were dead scared about getting distracted.

We're like, we gotta focus everything on men's tiny shorts.

We don't wanna do what X brand did that tried this and it didn't go well.

So what we ended up doing was just spinning up a new entity, putting a team in place and letting them take that business to the amazing heights that is at today.

So all of the credit to the team over there for how they did that.

It's just so cool.

Very fortunate to have been some very tiny small part of getting the thing sort of like created.

It's amazing. - Okay, we're nearing the end here.

I wanna do lightning round.

You gotta cap every answer at 30 seconds.

We're doing five questions.

What's your day to day like?

What do you do? - I write on LinkedIn and I'm kidding.

Well, no, I'm not kidding. - No, you're prolific on LinkedIn. - I do spend some time writing on LinkedIn.

I try to make it a daily habit.

I don't sleep a lot.

So I get up really early and I write for the kids.

And then sort of like the normal work day, building a new sort of like really, really early stage, actually SaaS business.

And so I can't really talk about it 'cause it doesn't really exist. - You're in stealth mode? - Early, early, whatever.

Yeah, people say stealth.

I don't know.

It's just early and it's not worth talking about, but that's sort of like taking up 150% of my time and it's super fun.

And I'm working with one of my Chubby's co-founders.

It's just a joy.

And I feel like I'm back in it again.

Feel that meaning, that focus, that singular focus.

And it's a joy.

Oh, sorry, 30 seconds, my bad. - All right, what's the single biggest misconception about building a successful e-com brand? - My take is that you have to address a large TAM.

I think that's baloney.

Make your TAM as small as possible so that you can get that initial foothold. - And actually, what advice would you give new brands navigating the e-com landscape but that I think you just answered it? - Well, maybe let me go to number two.

I think number two would be, don't rely on bottom funnel direct response as your main source of customer acquisition.

Imagine a world where Facebook didn't exist.

Imagine a world where you have $0.

What then do you do?

How then do you get reach?

How then do you change people's minds on a broad scale?

If I were to do Chubby's again, that's how I would do it. - For apparel brands specifically, how do you see e-com evolving? - I don't know if I do.

I could be missing something super obvious, but one of the things that I've learned is that nothing changes.

You're just selling stuff to people. - You, when you started Instagram, like you were there at the beginning.

Today, I think social media is much harder.

How has social media evolved? - It has become something that, I think in the way that every platform evolves, you can sort of like lose sight of the main purpose of it and the reason that it exists.

So again, I kind of feel like a crotchety old man just being like, nothing changes, go back to your basics.

But I guess that's sort of my idea is just sort of like ignore the noise, just like customer obsessed, like what works?

Why do you exist and just do your thing? - I like that advice.

My final question is gonna ask what's next for you, but we know it currently a secret.

Instead, where can we go to learn more about you? - Yeah, look me up on LinkedIn, Preston Rutherford.

There's a little shorts emoji in between the first and last name.

And maybe we'll link to that. - I caught that, I enjoy that. - Yeah, yeah, yeah.

So hopefully that helps it stand out a little bit.

But yeah, LinkedIn is where I'm just sort of like lurking all the time.

Like a weirdo. - I will include LinkedIn, your LinkedIn link in the show notes.

Tap or swipe up on the short.

Preston Rutherford, thank you so much.

This really, for me, a dream come true as a Chubbies fanboy. - Dude, Kurt, thank you.

This was fun, I really appreciate it.

And appreciate your support, man.

I mean, this was awesome to be able to chat with you.

And then yeah, it's been a joy to be a part of such an experience.

And again, I don't know if I made this point clear, but all of the credit to my other co-founders and the team.

I mean, I'm just yapping on here about podcasty stuff, but they're the ones who truly made it all happen.

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