Olivers—Founder & CEO, David Wolfe


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Every episode we talk to founders and leaders at some of the most exciting DTC brands in the world. We discuss their vision, how they launched, and how they are growing their brand.

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In this episode, we talk with David Wolfe, CEO and Founder of Olivers, a men’s activewear brand inspired by the farm-to-table movement.

Inspiration can come from anywhere. CEO and Founder, David Wolfe, says he was inspired by the burgeoning farm-to-table movement. That’s what led him to launch Olivers.

Consumers were becoming more interested in what they consumed — they wanted to know origin stories for their products, and there was a big emphasis on quality.

The entire visual identity, from clothing colours to website, was rooted in the farm-to-table movement.

They launched with one product on Kickstarter. All of their focus and effort went into that one item, and fortunately the campaign took off.

There’s so many steps to creating a prototype, and then making it at scale. For help David leaned on friends and family for support and help.

One thing David recommends: Get one thing right. Don’t focus on a collection. Focus on getting one product right, and then move on to a second.

If you go to their site, you’ll see a “House Rules” section. There’s one in particular that keep David healthy and sane: “Direction > Speed.” In other words, Focus on where you’re going, and not on how fast you get there.

Learn more about Olivers at oliversapparel.com

Thanks for listening!


Tell us a little bit about Oliver’s.

David: Yeah. Oliver’s is a high quality direct-to-consumer men’s active athletic wear brand, just over five years old, focused on really making fantastic men’s active and athletic wear.

So, five years ago when you started, what was happening in fashion and apparel that made you think that the world needed and was ready for Oliver’s.

David: When the business launched, we thought it was an interesting time. There was kind of this burgeoning movement. You know, really largely what I was kind of influenced by was what was going on in the farm-to-table movement in food. And that was just generally growing interest in all sorts of consumers about the products they were consuming and kind of the origin stories of those products. And maybe even more further to that, an overall interest in the quality of products.

So, there was this kind of burgeoning movement and this farm-to-table movement that we were paying close attention to. And really, it was applying those tenets and principles to men’s active athletic wear, which was a space that was kind of largely dominated by bigger brands focused on either low cost products or marketing messaging that was catered to either women or younger men ultimately. So, we thought there was this gap in the market for high quality men’s active athletic wear and catered to know a little bit more of an adult audience.

What were some of the key tenets and traits of the farm-to-table movement that you brought over and implemented in your active wear brand?

David: I would say the quality of materials for one, the origin story of where those materials were coming from too. You know, I think that focus on, call it craft over speed; those were three things which all kind of ran counter to what was kind of the standard operating procedure of the athletic apparel brands up to that point.

How did that influence your visual identity? Because there’s a consistency in the look and feel of your designs.

David: I think there is a certain color palette that we’re attracted to that I think has its roots and maybe a more adult grown up look (one). Two, that’s very kind of uniquely different than what the standard operating procedure of an athletic apparel brand is, which you tend to get a lot of black, white and gray. And we have this kind of affinity for colors and washed out neutrals. The color palette was, in our opinion, was a unique opportunity for us to do some that was different in the space.

And then I think we have other design details that maybe harken more to like a craftsman focused brand than it does to your traditional athletic apparel brand. So, no big logos, a focus not so much on speed and low cost, but on quality and craftsmanship.

So, it seems like that farm-to-table movement really infiltrated every area of the brand, not just the approach to making clothing, but the styles and colors and even visual elements like the website, logo and advertising.

David: Yeah, absolutely.

From the moment that you realized that there was a need, that there was a gap, what steps did you take to make sure this thing would actually launch?

David: So, we launched on KickStarter. And those days, it was rather — it weren’t a lot of guys doing that in the apparel space, but the platform did offer us an opportunity to test this concept, so to speak. And we had this brand vision and were able to kind of distill it down into a single product.

So, really, it gave us the opportunity to test a larger concept with one product and really tell the story around that product in a meticulous way. So, we put it in the story, in the video and focused a lot on the product and making samples and kind of getting it right and launched on KickStarter. And fortunately, the campaign took off. So, that was the springboard for really running this test and getting some good feedback and kind of going from there.

So, one product, one story; get it launched. What skills that you have to acquire? What did you have to learn to get this brand launched?

David: So, there’s certainly a lot of things. First time founder with this business. So, without clothing experience. So, you can imagine there are a lot of hurdles and kind of a lot of learnings along the way via mistakes and a lot of learnings from bringing in people who had certain domain expertise that I didn’t have and really leaning heavily on all sorts of people along the way.

Who were some of those people that you surrounded yourself with that you leaned on for support?

David: All sorts of people. You know, I would say friends and family. I happen to come from kind of an entrepreneurial family. My dad is an entrepreneur and a lot of friends and family; just people that I grew up with were entrepreneurs. I was able to lean on a lot of them.

And then in the industry itself, there is so many facets that go into making product and then selling it. So, really was just a lot of everything from favors, from all sorts of friends and family members to bringing in people in all sorts of facets in the industry that have a certain domain areas of expertise. So, a lot of components going on.

You know, I think luckily for us, we started and really for our first year, year and a half, only had a single product. So, that made what was still a very daunting kind of challenge, maybe a little less daunting. We weren’t trying to develop an entire fashion line. We were really focused on this one product. So, that at least help minimize kind of some of the complexities of making products, which is still even with a single product is complex. But minimize some of those complexities maybe.

What was the most daunting task or skill you had to learn in order to get this into the market?

David: I think figuring out how to actually make the product. I know it sounds really overly generic and I don’t know if that’s a great answer to a skill. But to actually produce a product in a large quantity, figuring that out was the most difficult kind of challenging thing and luckily was able to lean on a lot of people.

There is so many steps that go into finding all the different fabrics and components, making a prototype and then producing it at scale. So, just making product. I never had any experience making physical product. There’s a lot that goes into that.

When did you get a sense that what you had dreamt of and set out to do was turning into reality? When did you realize that Oliver’s was a thing?

David: We were fortunate in that this KickStarter campaign really took off in a way that we never could have expected. So, that was a really fun, kind of wild 30-day ride. Spent all this time prepping for that and then launched and we were lucky to have this great initial feedback. So, it’s like it was almost overwhelming, the feedback. It was almost like, Gos, we were in over our heads.”

There are some points along the lines of that first 30 days that was like, God, I wish it didn’t take off quite this much because now what am I signed up for? How do I get to deliver all this product to all these people?”

But the KickStarter campaign, I think was, you know, we were lucky and had this unique launch event that was a big tidal wave that we got to ride and I had that kind of got to have that initial ride that gave us some validation.

If you were to launch another brand and you could learn from the Oliver’s experience, what are some things that you can’t get wrong?

David: You know, I go back to us launching around a single product and I think you need to kind of have validation for a single product before you start making the next product, so to speak.

So, it’s kind of like get one thing right. You know, I think from a product side, you got to get one thing right. I wouldn’t focus on making a collection to launch. I’d focus on getting one product right and telling a story and getting that product right. You got to get the first product right before you move on to number two. And I think that analogy can apply to a lot of things. So, get one product right.

And then I think you’ve got to have the marketing and sales component. You’ve got to have a strategy for distribution. Online offers a really unique opportunity; like kind of a low cost way for people that put up a website. But as you’ve seen, that alone isn’t a reason for being — You’ve got to have a compelling kind of distribution plan figured out: Who’s your customer? How are you going to get the product to them from marketing and sales perspective? And I think a lot of people don’t know how to do that.

You know, you can have a great product, but if you don’t know how to get it to the customer or who the customer is, it doesn’t matter. And there’s also some not great products that the businesses are able to be around for a while because they’re great at marketing and sales.

Anyway, so I think get one thing right from a product side and can’t underestimate the importance of marketing and sales.

What were some of the marketing channels that you were depending on in the early days?

David: Yeah. So, we were launched at a unique time that KickStarter was just starting to take off, but it wasn’t kind of saturated in the apparel side. So, we launched with KickStarter and that was a really unique channel and that got us this initial customer base.

From there, we figured out — we actually, for the first couple of years, we’re doing almost everything organic. And once we’ve built up kind of an initial customer base, we started to expand a ton of the online channels: the paid social channels and then all the organic online channels that you’d expect. Spent a lot of time focused on PR, growing email.

I think that was all able to work because we had the initial kind of marketing and brand story that caught on. We were able to kind of leverage that initial customer base and that initial story which people found compelling to spread and all the other online channels.

How do you see that changing over time?

David: So, I think you’re seeing a lot of direct-to-consumer brands looking for other channels, and we’re certainly thinking about those. I think we really enjoy having that relationship directly with the customer.

When I think about Oliver’s, five or ten years down the line, I do picture us having our own retail stores. We’ve tested a number of different pop ups, some managed by us, some managed by other groups. But we’ve tested that concept; kind of having the in-person experience. And given that our roots are direct-to-consumer, I think that allows us to go direct-to-consumer in the physical world. So, certainly, I’d like the opportunity of doing retail.

Wholesale, we’ll see. You know, we’ve tested it in kind of small increments so far, but I think five or 10 years down the line, I think it’s certainly not unrealistic to expect we’d have a couple of key wholesale partners as a channel for distribution.

But yeah, I think ultimately, when you think down the line, all the online channels that I think you guys are well aware of, but figuring out how to get product to people in a real-world environment, such that they can try it on and become familiar with the fabrics and the products in person will be a key opportunity for growth for us.

How are you balancing growth? And what I mean by that is acquisition and sales. How are you balancing that with brand building and awareness? Is there retention there for you?

David: Yeah, absolutely. And I think all of the advertising we do is we think of it kind of brand first as well; brand and product first. And this, we might touch on a little bit later.

But we’re a friends and family-funded business, haven’t taken on any venture capital. And so, I think that’s important, as we think through all these decisions, because we only do things from a marketing and advertising perspective; that makes sense. And it makes sense from a bottom line perspective and also makes sense for the business; bottom line and also from a brand and marketing perspective, just generally speaking.

So, that discipline kind of ensures that we’re only doing things that our customers are responding to. We’re not kind of spraying and pray; we’re testing things in really small increments and when they work, we’re scaling them up.

We’re not run like a tech company; we’re run like a real business, so to speak. That focus and that discipline, I think, manifests itself in good decisions, from a marketing and branding perspective. It forces us to make good decisions.

Is that part of the reason why you went with the KickStarter to begin?

David: Yeah, that was part of the reason for sure. Also, didn’t have experience raising capital. And I think looking back on it, actually spent some time in the early days trying to raise capital; never had success for, I think, a number of reasons. You know, I think for whatever reason, I wasn’t good at fundraising or the story wasn’t compelling enough or whatever the reasons may be.

But in hindsight, I think it’s worked out to create a healthier business, at least for us. You know, everyone’s got certain initiatives and certain things. You know, not what’s right for us is right for everyone, but not having fundraising success forced us to kind of run this like a real business. And I think there were some tough early days, but it’s helped make the business, I think, stronger, having made it through, so to speak.

Do you think that perspective on fund raising is going to change at all as you grow?

David: Yeah. I don’t know. It’s certainly possible. I mean, I realize there’s some things for which capital is required, and that’s just the nature of reality and growing a business. But we do run the business and the brand; view it through a really long term lens. You know, we’re not trying to grow by any means necessary and we’re not on the fundraising kind of cycle, so to speak. So, we very much view the business through a long term lens, and that certainly shapes a lot of our decisions, both on the capital side and on the day to day business side.

David, what did the team look like when you started? Who did you bring on? Who did you need to get this thing launched?

David: You know, we didn’t raise any capital to start. So, I kind of put in some savings and really brought on a bunch of contract workers in all sorts of kind of aspects of the industry and relied on favors from friends and family members. So, it’s kind of patched things together, so to speak, very much like, you know, had to be very scrappy.

But required a lot of people on the product side to help out. You know, brought in someone to help set up manufacturing, brought in someone to help source. You know, there’s a lot of different vendors kind of along the supply chain and making the product.

So, had to work with a pattern maker to make an initial pattern and had to make samples from that. Had to figure out sourcing. And these are all kind of like different aspects of making a product that we had to bring in different people for. So, pattern makers, sample maker, someone to help with sourcing, someone to help set up production.

And then on the marketing side; graphic and web people to help not only build the KickStarter page, but build the site. And then marketing helped. You know, I had some marketing background myself, but marketing help; from copy and figuring out advertising initially as well.

At what point did you think it was a good time to launch your second product?

David: It took us about a year, year and a half before we did that. You know, we were very deliberate in trying to figure out what that second product was going to be.

I don’t know if there’s any specific moment in time that was like, “Now, it’s time to launch it.” But you certainly want to get kind of some of the fundamentals, some of that kind of baseline operating things hashed out of the business. So, I wanted to kind of finish production and get production really dialed in on the first product, re-launch kind of an updated version of the site, just to kind of get a little bit of a baseline in place in terms of us operating the business. So, it was about a year, year and a half.

How hard do you think it is for a bigger brand with more resources and money to come in and do what you’re doing?

David: I think it’s pretty hard. You know, the barrier to entry of just putting up a site and launching isn’t that high, especially nowadays; that’s been lowered a lot.

But building a brand, I think, is something that it’s hard to accelerate the process of building a good brand and a loyal customer following and making good product.

But really the first two in particular, like building of the brand, building kind of a loyal customer following, you know, money maybe can help with that, but those things, I think, are a factor of time, more so than they are of money.

So, anything about the great brands? I think probably all of the brands you think about as fantastic brands, in terms of like iconic brands, probably none of them have launched in the last five years and probably none of them are, at least when I think of like the great iconic brands, none of them are venture backed businesses that poured a bunch of money into the top of funnel right away.

I think a lot of what goes into making a great brand is just the nature of surviving, making good product for a long period of time and building a certain amount of customer loyalty, which a bunch of money in the top of funnel can’t really solve for.

Brand building and customer loyalty then; more a factor of time than money. I like that.

When it comes to brand building, there is one thing that stood out to me on your site and that’s the house rules. I’ll list a couple.

  • Health is a craft; you have to hone it.
  • If you ignore history, it’ll ignore you.
  • There’s no such thing as a natural born pilot.
  • If you don’t believe one man can change the world, then you, my son are not he. And
  • My personal favorite direction greater than speed.

Why are those important?

David: I think it helps create an atmosphere and a feeling around the brand. And it speaks to the audience in a way that, I think, is unique compared, you know, going back to who we are, where we’re positioning ourselves in the marketplace, the customer we’re speaking to. I think this is an opportunity to do that in a fun, playful way.

And it’s our way with what’s currently our site and we have some maybe long term aspirations of doing things offline, but to make it feel like it’s a club. And not an exclusive club, but a club that has a certain vision and mission such that, there’s a certain amount of people that we’re for, but we’re not for everyone. And that’s intentional.

And I think this is kind of a fun, playful way to almost describe our values and our place in the market. And I think it’s probably a pretty clear distinction between that, you know, our house rules and say if some of the big brands that are our competitors, our space; if they were to come up with house rules, they’d probably sound quite a bit different than this. And that’s intentional. And it’s our opportunity to do that in the playful way.

You also have something on the site called The Playbook. Tell me a little about why you built it and about the content and themes you’re writing about.

David: Yeah. So, The Playbook is our journal, our blog. And it’s actually something that we’ve, in the past year, we’ve re-launched with new content and a new format; we’re really excited about that. Brought in someone who is focused on overseeing all the content around that and the kind of vision of that.

You know, I think another really fun opportunity for us to, I guess, add value and explain the kinds of stories and tips that we think our customer would find relevant.

I think we’re very intentional now and the kind of new format of this is to provide value for our customer. And we’re very intentional like this was going to be a marketing channel that wasn’t going to be focused on driving sales, it was going to be focused on having interesting facts and anecdotes and stories that our customer would find valuable.

And meaningful and the kind of things that they could kind of bite off and it wouldn’t be a huge, long, overwhelming story to read, but they could look at it in a couple of minutes and really take away something or maybe a couple things of value and be entertained. And it wouldn’t be part of the site where we were selling them products. We were just providing value, so to speak.

What’s one of the hardest business decisions you’ve had to make at Oliver’s?

David: Well, couple of things. One, we had, as a lot of businesses do, we had some legal challenges early in the founding of the business that provided some challenges and had to make some tough decisions there, decided to move the business in its early stages from San Francisco to L.A., which is a big kind of undertaking.

Yeah, legal is never fun. And I can imagine moving in office is not easy.

David: Yeah. No, for sure. It was a big undertaking. You know, we’ve had to move manufacturing a few different times and every time, the outcome’s been better than what we had before. But doing that, that’s always been a big challenge. So, those are three things that come to mind.

How do you prevent yourself from burning out and make sure that you’re well enough to lead the company through the long haul?

David: We’re lucky in that it’s a business that I’m the customer for. So, that makes it really fun. And it’s something where I was able to kind of impart a lot of my personal values into the business. And I was fortunate and it just happened to be a segment in the market where I was able to build something that I was really the customer for, then that really mattered kind of uniquely to me.

The other thing is you talked about the House Rules; direction over speed. And that’s something that we benefit from; we’re not in a rush to get anywhere. We’re trying to make really good product and be around for the long haul. So, I don’t feel like we’re running to get anywhere, so to speak, if that makes sense.

And because of that, I don’t feel overly stressed at this point. We’re lucky we’ve made it out kind of the early stages, from being an infant to being able to crawl, and now a lot of what we’re doing on a daily basis is making the product better, making everything better and with a long term focus.

So, I would say just by virtue of having a really long term focus for the business, we’re not constantly exhausted because we’re not sprinting to get anywhere, so to speak.

What other direct-to-consumer brand do you look to for guidance and inspiration?

David: I mean, Rapha was kind of in the first wave of that and they were a high-end cycling brand. I’ve always admired what they’ve done. They have retail stores now. But they were kind of a first wave of direct-to-consumer businesses.

I’ve always liked what Buck Mason does. They’re another brand base down here in Los Angeles, focused on similar demo than we are; Men’s, but kind of daily essential type pieces.

Harry’s is a shaving brand. I’ve always thought they’ve done a really good job as a direct-to-consumer brand. Those are three that stand out.

And who would you like to hear from here on the show? What brand or founder?

David: I think Rapha, that first brand that I mentioned; the cycling brand. Simon is the founder; London based brand. They’ve been around a little bit longer.

Like I said, they’re kind of the first wave direct-to-consumer brand. They’ve been around probably 15 years or so now. And he’s someone who I’ve followed a little bit, but that’s a guy I’d love to hear in the interview.

That’s great. We’ll try to get him on the show. And when we do, we’ll let you know.

David: Yeah.

Roger: David, thanks for taking the time to talk to us today.

David: Yeah, it was a lot of fun. Thanks, Roger. Appreciate it.

If you haven’t already, please visit oliversapparel.com to see what people are calling the most comfortable pants they’ve ever owned. Again, that’s oliversapparel.com.

Thank you for joining us. Thank you for listening. This is the DTC Growth Show by #paid.