696: Jamie Left a Nike Exec Job to Bootstrap A Drinkware Brand - Now It's On Track For Seven Figures

19 Aug 2026 · 1 h · 25 chapters

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In short

Jamie (Summit Outdoor) explains how he bootstrapped and scaled a premium outdoor drinkware brand after leaving a long corporate career, using product innovation, AOV/bundling, and ad/website optimization to reach a seven-figure run rate.

Guest backgrounds

Jamie is Summit Outdoor co-founder and former Nike executive (also mentions experience at Logitech). He and his wife Michelle started the brand; they live in Park City, Utah. He joined Founder Operators (D2C community focused on scaling with Facebook ads). No other guests are named in the transcript.

Key claims

Summit Outdoor’s drinkware is 90%+ of revenue (bags/headwear are smaller). The brand pivoted from bags to drinkware after 18 months and ~50 prototypes. Jamie went full-time “day one” and bootstrapped to keep control and avoid misaligned investors. Growth acceleration with Founder Operators came mainly from improving conversion rate and especially AOV via bundles, offers, and website/PDP storytelling; traffic increased but was not the primary lever.

Notable examples

leak-proof lid system innovation; Mason-jar-inspired shape; limited editions capped at 980 units; personalization using a second 3PL; CGI/CAD-based product visuals to show details (e.g., lid knurling); ad creative focused on aspirational “moments of pause” lifestyle rather than just sales.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Meeting Jamie and Summit Outdoor

1:51 to 2:39

Jamie's journey from Nike executive to co-founding Summit Outdoor.

“Jamie, thank you so much for joining me.”

The Inspiration Behind Summit Outdoor

2:40 to 3:24

Jamie shares the story that inspired him to create Summit Outdoor.

“Nick, myself, the founder team, it's been awesome.”

Bringing the Product to Life

3:25 to 4:52

Jamie discusses how he validated the market for his drinkware products.

“Yeah, we're about three years into the journey.”

The Launch Journey

4:53 to 7:00

Jamie narrates the challenges faced during Summit Outdoor's launch.

“I was really obsessed with that emotional space too.”

Bootstrapping vs Funding

7:01 to 9:12

Discussing the pros and cons of bootstrapping a business versus seeking investment.

“But what I liked about sort of the drinkware space was some of the things that were different about the category from what my experience was, which is it's super easy to ship, it's small, it's packable, it's storable.”

Lessons from Bootstrapping

9:13 to 14:02

Exploring the lessons learned from bootstrapping and the urgency it brings.

“And as much as, you know, I had some experience in the, in the space, I definitely was not an entrepreneur.”

The Case for Bootstrapping

14:02 to 15:10

Explore the advantages of bootstrapping a business for deeper understanding.

“conversation and, and certainly I've, I've seen, you know, people and friends that have, have gone down that path.”

Launching Drinkware: A Pivotal Shift

15:12 to 18:06

Learn about the launch of a new drinkware product and the challenges faced.

“You went through many different prototypes.”

Focus on Drinkware: The Main Hero Product

18:07 to 19:30

Understand the importance of focusing on a single product line for success.

“So now you still sell bags, you still sell headwear, but drinkware is your main hero, right?”

Innovating in the Drinkware Space

19:32 to 21:47

Discover key innovations in product design and consumer experience.

“So now doing it wrong, we started at 25.”
Show all 25 chapters

Going All-In: The Entrepreneurial Decision

21:48 to 24:42

Hear about the commitment and thought process behind going full-time in business.

“sort of sprinkling in some of the design ethos that we wanted to represent.”

Building a Sustainable Family Business

24:43 to 27:00

Learn how to create a profitable and sustainable family-run business.

“My wife and I, she has helped me a ton, but doesn't do this full time.”

The Rocking Chair Test for Decision Making

27:02 to 28:08

Discover a unique perspective on making life decisions based on long-term impact.

“I really respect the business that you are building and it's freedom first and it's passion.”

Core Values in Decision Making

28:08 to 29:26

Explore how personal core values influence business decisions.

“And I think it allows you to kind of make decisions that are really core to who you are, not necessarily the things that might be driving you in the moment.”

Business Growth Journey

30:05 to 33:48

Jamie shares his growth journey from skepticism to success.

“We only launched it four or five months ago, but you took a chance on us, right?”

Metrics and Consumer Experience

33:48 to 36:24

Discussing the importance of metrics and enhancing consumer experience.

“And what I would say underneath in terms of profitability, traction, you know, growth of sort of how I'm thinking about margin and sort of bottom line is as exciting, right?”

Advertising Strategy and Emotional Connection

36:24 to 38:45

How to create emotional connections through advertising for drinkware.

“It's not a super high AOB product per se.”

Investing in Brand Experience

38:45 to 42:00

The significance of brand experience and product presentation.

“But at the end of the day, really, like, how do we just convey our brand in a better way and share our story in a better way?”

Building a Brand Experience

42:00 to 44:43

Learn how to create a compelling brand experience that engages consumers.

“And he'd come from a brand that was a DTC success that was industrial design based.”

Driving AOV and Conversion

44:43 to 46:55

Discover strategies to increase average order value and conversion rates.

“And it's like, no, think about the true consumer experience that you're trying to deliver for somebody that you're inviting in and trying to build trust with.”

The Entrepreneurial Journey

46:55 to 49:04

Understand the non-linear nature of entrepreneurship and the importance of resilience.

“of one of the things that we layered in right at the beginning.”

Learning from Mistakes

49:04 to 52:49

Explore the significance of learning from setbacks and maintaining a growth perspective.

“it over two months, you can see the progress you've made.”

Success Metrics in Business

52:49 to 56:00

Examine the factors that contribute to startup success beyond just ideas.

“And it's, by the way, it's not for everyone.”

Lessons on Passion and Challenges

56:00 to 57:41

Discover the importance of passion and mindset in overcoming business challenges.

“And I know we're up like almost 50 % year to date, But our Q1 was definitely not as high a growth as since we've joined Founder.”

Reflecting on Support and Progress

57:41 to 59:08

Hear a discussion on the support received and the journey of growth in business.

“passion for what you're trying to solve and just reminding yourself that because it's super easy to get bogged down into the whatever it is.”
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Transcript

Automatic transcript. May contain errors.

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1:06Welcome to Little Empires, brought to you by the team at Founder. At Founder, our mission is to support the next generation of e-com founders. So while you may know us for interviewing some of the world's most successful entrepreneurs, this series is a little different. Little Empires shines a spotlight on the builders inside our own founder community, the entrepreneurs who are in the trenches, taking action, learning, and building their businesses in real time. These aren't overnight success stories. These are real journeys, real lessons, and real founders creating their own little empires one step at a time.

1:39This podcast is proudly produced by the founder team to give our students a platform to share their experiences, wins, challenges, and honest realities of building a business from the ground up. Now, let's dive into today's episode. Jamie, thank you so much for joining me. Really excited to speak with you today. So you are the co-founder of Summit Outdoor, incredible brand, and we met in March of this year. You are a member of Founder Operators, our new D2C community where we help brands scale, especially with Facebook ads. You've had tremendous growth since you joined us in the membership, and we've played a very, very small part.

2:25You've done an incredible job, but when you came to us, you had some challenges with ads, with growth, and I feel like we're only scratching the surface with what we can do, and it's pretty exciting. So first and foremost, welcome. It's been so inspiring to watch your growth from afar. Nick, myself, the founder team, it's been awesome. You're an amazing case study for what is possible, following our system, following our frameworks. But welcome to the show, man. Thank you so much. I was so excited to be here with you. And yeah, you're right. We've been in this for a little over three months, so it's an awesome time to catch up.

3:00Yeah, 100%. So how'd you start Summit Outdoor? You come from corporate America, successful Nike executive. You started this brand with your wife, Michelle. The water bottle space is near and dear to my heart. I built a successful D2C brand in that space, a little different. Your products are definitely much more durable than what I created and definitely a much more deeper sense of mission. So yeah, how did you start the brand? When did you start? Yeah, we're about three years into the journey. And as you mentioned, I guess I would say non-traditional path in that I'd spent over 20 years in kind of the more traditional corporate career space.

3:38And I am what you'd call probably a user entrepreneur. I focused on a problem because I had it personally. I actually hadn't experienced a moment where I had a failure of a product and it sort of lit the light bulb, if you will. We live in Park City, Utah. Our kind of lifestyle is built on the outdoors. I had had this nearly kind of perfect day. We was spending the day with my brother and sister-in-law and my wife. We had gone hiking. We had played some golf. For me, the quintessential reason why you live in Park City is kind of spending the days outdoors. And we were having a barbecue afterwards.

4:20And I was hosting and having a couple of buddies over and my brother and sister-in-law over. And I was bringing drinks out to the group. And I tripped and fell and literally sent drinks everywhere at everybody. And I was like, you know, this to me is like, there was two pieces of it that really sort of unlocked the summit journey. One was, okay, I, you know, I really wish that products were built with sort of a different concept of leak proof that kind of lived up to the lifestyle that we had. There was that sort of problem I wanted to solve, but it was also like, how do I capture the day that I just had?

4:57I was really obsessed with that emotional space too. How do we bring that sense of experience of life to people? And we love this idea. My wife and I love this idea of sort of these active outdoor days and these moments of pause, right? This, this yin and yang of that lifestyle of, you know, really celebrating sort of the ability to get outdoors and explore and be active, but also like just as important. And I think in kind of today's world, how do we help people find moments of pause, those moments to, you know, sit back in the chaos and really enjoy life and people around you in a different way and sort of drinkware just felt like it was kind of at the center of that.

5:39It just felt like a really good medium to kind of express both that innovation that we wanted to create, but also the emotional space, the kind of the brand space that we wanted to live in. And so, you know, we just happened to stumble upon the idea because I happened to trip and throw a few drinks at people and had an aha moment. Yeah, what a crazy story. So you started three years ago. So how'd you bring the product to life? How did you even know there was a market? Like talk me through that. Like how'd you validate this thing? I wish I could tell you like it was some extremely sophisticated business case study that I researched and studied deeply.

6:16I think I actually started down the path just through passion. I think there was a couple of things that were going in my favor. One is I came from the consumer product space. And so, you know, working at Nike, working at Logitech, you know, I had this familiarity with obsession with consumer obsession with kind of product design. And I had this, this nice world around me, you know, friends and experts that I could reach out to, to kind of get started, you know, the design process, finding a supply chain and manufacturing partners, thinking through the marketplace, I was coming at it from having spent some time there.

6:57So I knew, you know, the importance of the category with some of the traditional retailers in the US. And so, you know, outside of obviously spending some time looking at size of category market share stuff, a lot of it just came from from experience, you know, my, my background was in footwear and apparel and I knew that space really well. But what I liked about sort of the drinkware space was some of the things that were different about the category from what my experience was, which is it's super easy to ship, it's small, it's packable, it's storable. I love that it really is a non-gender category, right?

7:33Like you don't have size curves of men and women. So from an inventory perspective, I knew it was a little more efficient than some of the categories that I came from. Those were some of the things just going in, kind of knowing that there were some differences to the space that I'd played in in the past, but also being able to lean on and leverage some of the, you know, the background and experience that I had to get into the business. So you would have launched what, 2023? Yeah, middle of 2023. How did you launch? Did you launch with just one skew, one style? Talk me through that. Was the launch a bang?

8:11Every startup has a pivot story. This is effectively ours. We didn't start in drinkware. We actually started in bags, which was a category that I knew a little bit better. And I told you about the founding story. It took me a longer time to really figure out a category I didn't know. getting into industrial design, we probably spent the better part of 18 months and 50 prototypes getting to drinkware. So I actually used a lot of that passion and that insight of this idea that I had, but I actually launched with something that I could get to faster. And so we started with bags, knowing that drinkware was where we really had a really core insight, but I leveraged some of the thinking there to get into a similar concept for bags.

9:03They were also insulated, were complimentary to where I wanted to get to. And I would say, you know, like a lot of founders out there, you know, I was going from billion dollars to like blank sheet of paper. And as much as, you know, I had some experience in the, in the space, I definitely was not an entrepreneur. And, And the learning curve was almost truly vertical for me in a lot of ways, particularly around where Founder is helping me. And it was not like an immediate success. You know, there was weeks in the beginning. We did a launch party and stuff. We had a lot of great support locally.

9:41And I think that's a really important thing for any brand is just to kind of focus on that first concentric circle. You know, the people that know you and know why you're doing it. And, and so, you know, we, we did some things really early that I think helped start to build the brand, but from a commercial standpoint, it was slow, right? Like there was days where it was like, gosh, did we have an order today? I'd love to hear like, yeah, and tell me the flashbacks. Like, yeah, I mean, I, you know, I remember there was weeks, you know, in the first two or three months where we might have like an order or two in a week, right?

10:16Like where there was days where it was crickets to some degree, like everybody kind of knows that if you're going to get into the startup world, like you're going to run into challenges. Right. But for me, I think it was really like, wow, I was thinking I had all this knowledge that I was pouring into something new and on my behalf with my wife, but it really started to go or help me realize like, I have to learn a lot, right? like website setup, you know, what a consumer experience should be on a website. How do you drive traffic in a meaningful way with limited resources, right? Like you compare it to Nike and sort of how you think about what the position you're in running a business there versus like, okay, every dollar is coming out of my pocket.

11:02How do I resource this in a way that makes sense for the business, but I'm not just, you know, lighting cash on fire. And so, you know, you go into those, those moments and some of it, you got to just charge forward. And I'm, I'm actually glad I did. Cause we'd learned a lot from bags, even though we, we ended up pivoting to drinkware, which was always kind of the number one goal, but it made me realize I got to learn really quickly. It is very different, right? You, you know, as, as an executive at Nike, you're leading teams of teams. You have a good budget. You've got, you've got a decent amount of firepower behind you.

11:36And And I remember when we met, you're like, man, like I'm just a solo operator. Like I've got like one kind of contractor here. Like, yeah, it's just me. So it is very different. Yeah. And I, you know, I think that's for, for founders, there's all these like strategic decisions, right. And, and, and a lot of people probably don't even know if they're making them or not, but like one of those is do you fund it really well and the choices that go along with it, Or do you bootstrap it, keep it a lot tighter, keep it to some degree smaller, but have a lot more control? And, you know, it's a major choice.

12:15I think, you know, we've talked about this in the past. My background before Nike was actually in finance. And I had a reasonably strong point of view about kind of the early stages. I really wanted to feel the pain of putting my own capital in. But the benefit of that was, you know, the cap table is just my family. It's probably the most supportive, you know, group of investors you can possibly have. And, you know, from a strategy and control perspective, you know, for the longer term, it put us in a position to make long term decisions. We weren't trying to win tomorrow, we were trying to do the right thing to really build a sustainable, successful business for the long term.

13:01And when you have capital with different points of view, oftentimes that can lead to a different set of challenges, right? Where you're trying to make sure that everybody is aligned to the decisions you're making, that the growth decisions work for everybody. And the benefit or the luxury that I have is that largely the decisions are mine. And so I can make those kind of myself. Yeah. And, uh, I, I can really resonate with your journey from a funding standpoint. I, I've tend to have always built businesses bootstrapped and haven't seen that side of the table, venture, all of that good stuff, um, maybe one day.

13:41And so you kind of, it's, it's$0 marketing strategies. It's direct response, really knowing your numbers. It's, it's high margin, healthy business. It's being super strategic. It's scrappy, but I tell you what, it's the best way to run a business because it's real. I, you know, I agree with you. I, you know, there, obviously there's another side to this conversation and, and certainly I've, I've seen, you know, people and friends that have, have gone down that path. And I think there's some real pros to that as well. Um, but, but I, But I agree with you. I mean, I think, you know, the sense of urgency, the immediacy of really understanding your business, your numbers, the sense of urgency around the things that are going to impact the business tomorrow, all of those things, I think, just come with a different degree of urgency when it's coming out of your own pocket.

14:37And I'm a big fan of it just because I think you learn so fast with that as sort of the backdrop of a business. And even if you raise later, to some degree, bootstrapping first makes you an expert in your business, probably gets you on a little bit of a runway and probably helps a little bit with valuation. And so I think there's even some benefits, even if you're thinking about funding it and financing it in a more robust way. Yeah, I agree. So talk me through. So you launched three years ago. You went through many different prototypes. You launched with bags. When did you start to pivot to Drinkware?

15:23We launched Drinkware late in Q4 of 2023. I actually think we launched Black Friday, Cyber Monday week. I will say, you know, we're pretty premium brand. We've, we've focused on investing in innovation in the category. We were not the lowest price point by any stretch of the imagination, but yeah, we, we kind of, we, we launched Drinkware, you know, in this, this incredibly chaotic consumer moment, right? Obviously, consumers are thinking about the holidays. They're thinking about when there might be an opportunity on pricing. We didn't know what we didn't know, right? This was the first product.

16:07So we launched in, obviously, late November. And I remember we were actually, I was traveling with my family for the U.S. holiday of Thanksgiving. And I was sitting with my parents and my brother. And we were kind of just waiting to see if there was those Shopify pings. you know like is this gonna work or not and i remember like a dinner conversation on like what's the over under on day one and those are those memories like i you know as as small as they are they're the things that kind of fuel an entrepreneurial journey you know those small moments where you're sharing something with you know close friends or family and the sense of anticipation and like in a lot of ways for an entrepreneur this is more than a year, it was probably closer to two years of work, kind of showing up to the consumer or to the broader world.

17:00It's a big moment for you, you know, as much as it might have only been, I think we had like 25 sales the first day or something. You know, we're not talking about setting the world on fire, but you know, those are even though they're small commercially, they're huge moments from the emotional journey of being an entrepreneur and they're what fuel you. They're special and they kind of build some energy for you that kind of carry you through the tough moments. You know, it was definitely like different than the true launch of the brand because, you know, I think we did 20 or 25 units. We weren't even really advertising at that stage.

17:39A lot of it was word of mouth. A lot of it was preceding and just telling people the story and showing them prototypes and things like that. And we started advertising shortly thereafter, but not really knowing what we were doing and kind of learning as we went. But just from the reaction of that, we kind of knew that it was in a different place than some of the concept we had for bags and knew that we'd made the right decision in terms of where we'd put our energy and focus. Interesting. So now you still sell bags, you still sell headwear, but drinkware is your main hero, right? You would say that?

18:18I would. Yeah. I think, you know, drinkware is probably over 90 % of our business. Our, the bag concepts we had, I, I really love, I still love, but these are like, this is a perfect example of, of, you know, the choices you have to make as a startup. We, we likely won't do bags for a while just because of capital, right? Like when you buy inventory, when you invest in with, with drinkware, we, we have to invest in tooling, right? So it's, it's a truly industrial designed product. You know, there's, there's a lot of capital outlay to just get to a product on the website and doing that across multiple categories is wonderful if you have some scale, but when you only have a certain amount of cash and you're like thinking like, here's my next six months and I have just enough cash to kind of do the plan that I've laid out, you make really tough choices.

19:13And so instead of like iterating on bags and really improving what we wanted to execute, we made the decision to just really focus on, on drinkware. And, uh, that doesn't mean we won't get to other categories, adjacent categories for us in the future, but, but yeah, drinkware is, is 99 % of our focus. And look, that, that makes sense. Like you have like five different skew products in drinkware alone right these are awesome products right and i know you said they're they're somewhat premium but dude i was selling this product yeah this is my product i was selling the healthish water bottle for 30 us dollars with free shipping worldwide like it's it's it's crazy like like your product like i'll be honest your product is far superior to to this product like This product costs$2 US to produce.

20:07Oh my gosh. I love your margin. Yeah. So now doing it wrong, we started at 25. We did a test and we, we did 25 with the shipping threshold. And then we did 30 without a shipping threshold, just, just free shipping everywhere and free shipping converted way better. We were, we, we, we converted around four and a half to 5 % of people. We, yeah, we were, we're in the same boat. You know, we're still learning some of those things. I think our pricing, you know, we, we are, you know, around some of the major incumbents, you know, the recognized brands in the space, what we were, you know, and, and I'm, I'm very comfortable with that.

20:51My background is in more premium brands. I like playing the role of really being an innovator in a space versus like trying to just follow a trend. And that doesn't mean that there's not great business in those spots. It's just not my background and experience. We were really obsessed with like, hey, this is a really competitive category. Footwear and apparel are too, obviously, and our background was in those kind of spaces. We were like, we're really going to think about consumer experience, about intuitive design and places where we could carve out some IP, right? really have a technology advantage, create a moat that felt kind of novel and unique and different.

21:34And so, yeah, when we got to these, we were really thinking about that initial user experience and how do we, the baseline of our brand really starts with leak proof. And so we were thinking about lid systems and the frustration of lid systems and how they work and layering in or sort of sprinkling in some of the design ethos that we wanted to represent. You know, we are, we live in a mountain town. It's a resort town. It has this amazing heritage of like Western ranch lifestyle. Mining was the original reason why, you know, people came across the country and lived in places like Park City. And so like, you know, even the Mason jar kind of inspired shape came from this deeper kind of design story that we wanted to tell.

22:21But, you know, the lid system, you know, we, we added a lid to what would traditionally be what you buy in drinkware, but we wanted a solution that was super easy. You know, like we didn't want you to have to leave a lid on the table. And, you know, so we, we spent some time on that and really felt like it was important to have an innovation point of view entering the category. And so that's, you know, that's why it took us longer, right? Like we, we, we spent a lot of time in the gosh, there's prototypes in my office that are like, wow, remember when we were trying to do it that way? And it just didn't work the way we wanted it to.

22:58We wanted it to be hyper simple for the consumer, but still deliver value that we felt like was not quite there in the market today. I love the differentiation. I love the story. I love the meaning and the sense of purpose behind your brand and I think it's incredibly powerful and so one thing I'm one thing I'm curious around is like when when did you go full-time and and what range of revenue did you get to for you to go you know what I can go all in on this because you know when you joined us in March there was there was a little bit of apprehension around kind of you're just a solo operator it's just you and you have a contractor there's a little bit of nerves around kind of you know working with us joining found operators and the membership because all these different things.

23:46Um, but I'd love to hear, like, when did you go full-time? When did you go, you know what, now's the time. I went full-time day one. Uh, really? I was all in. And I think a lot of that speaks to kind of just my stage of life. You know, I'm, I'm obviously an older entrepreneur than, than a lot of great entrepreneurs. And I had had, you know, 20 plus, you know, 25 years and in kind of, you know, corporate roles and executive roles. And, you know, the opportunity cost for me was like, if I didn't do this, I would probably be, you know, looking for the next CEO job of a fairly large company. And so for me, it was like, A, I really want to do this all in, I want to do this right.

24:32I don't want to have any questions at the end that said, gosh, had you really focused on it, maybe it was an opportunity. So I went in all in from day one. We had the heart to heart as a family. My wife and I, she has helped me a ton, but doesn't do this full time. She actually works full time. And so to some degree, there was some balance to that that helped. But we said, hey, Right. Two to three years isn't going to put anyone on the streets. It's not jeopardizing the kids' education. Let's focus on it. Now, yes, I've been very strategic, maybe giving me too much credit. I've been very focused on making sure that we don't add a ton of expenses that cripple cashflow or don't put money directly into trying to grow the business.

25:20You know, since we started, though, we now have a small team. We have, you know, several folks working on the business, at least half time, like 50 % of their time. So they are contractors, but they're a part of the mission. You know, they feel the brand. But you know, we weren't getting office space. You know, we weren't we weren't investing in like luxury things. We were trying to put the money into the business. And from day one, I wanted to make sure that if I did, you know, have to shut it down or move on or whatever, that there was no like regrets that I, I didn't say to myself, gosh, well, you didn't really put in 120%.

25:55Right. And so, yeah, I, we made the decision kind of day one, it was full time. You know, there were some like jokes early on, like Jamie's retired. And I was like, guys, like, this does not feel like retirement. Like I'm probably working as hard or, or harder than I was, you know, when I was getting a salary, you know, I'm trying to do this because at the end of the day, what I did not want is a side hustle. I wanted a large sustainable business. And, and, you know, I ultimately built it in a way where I felt like a family business was a great win. Like I, no one needs to be on the cover of Forbes magazine, right?

26:31Like building a 10, 15, $20 million business is a really incredible thing. And I don't think people talk about that enough. It does not have to be a unicorn to be a really successful effort. If it happens to go that direction. Incredible. Great job. But I wanted to build it in a way that creating a family business was still a success, that it had the infrastructure that a smaller business could still be profitable and could still be rewarding to work on. I really respect the business that you are building and it's freedom first and it's passion. I believe life is too short to not do work you don't enjoy.

27:13I totally agree. I share this a lot as a way of thinking about, you know, big decisions in life. One of the most important ways that I've figured out how to make or think about sort of big pivots and big decisions is what I call the rocking chair test, right? And the ability to kind of fast forward to much later in life and kind of look backwards at what you're going to regret the most. What are the experiences you really want to have so that when you are 70 or 80 or whatever that time frame is that you can kind of look at it and say, these are the things that really enriched my life. These are the things that I really want to do experience and go through.

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27:52And I think it's a nice way of kind of separating yourself from a big decision and just be like, what's really important to me? You know, how am I going to look at this when the pressure's off and I'm evaluating my life from a vantage point of having fully lived it? And I think it allows you to kind of make decisions that are really core to who you are, not necessarily the things that might be driving you in the moment. You know, certain people are like, hey, I have to make money. I have to just drive my lifestyle forward right now. Or, hey, I've got, you know, a family situation and these things are driving me.

28:28But I think it allows you to kind of step back and say, gosh, what's really important to me and how do I pursue those as the most important priorities in my life? Yeah, that's an amazing way to look at it. And I couldn't agree more. I don't sit back and kind of look at these kinds of things, but subconsciously a lot, I'm kind of like, yeah, that's where I want to go. I want to live like that's how I've always kind of lived my life. But no, I really respect that. So Jamie, talk me through like when we met in March, you know, we just opened up founder operators. Where was the business at? You were running some ads.

29:02I never forget. I talked about this offline. There was a little bit of skepticism there around what we were building. And he described the coaching industry as somewhat of the panacea of entrepreneurship, but I'd never heard anyone describe it that way before. And Found Operators is a membership, but it's also a coaching program and it's a community. Real quick, before we jump in, I want to shout out one of our sponsors, Xero. I've used Xero from day one of Founder, 13 years now and it's still how we run the business today. It's cloud accounting software built for founders exactly like us and it automates all the admin that I used to do when I first started founder.

29:43Invoicing, chasing payments, expenses, all the accounting. It really helps me get paid faster and keep an eye on cash flow. So founder listeners get a crazy 95 % off for the first six months just sign up through our form at founder.com forward slash zero. Terms and conditions apply. Remember, when you support our sponsors, you are supporting the show. All right, now let's jump back in.

30:09You know, it's still early days. We only launched it four or five months ago, but you took a chance on us, right? Because we did a couple of calls. You're like, man, I'm not sure about this thing. And, you know, I'm only a solid operator, but where was the business at? Talk us through and what was going through your mind? Where were we at? You know, we had the one drink where Productive was 90 % of the business. We were not seven figures. We were probably doing somewhere in between 20 and 40K in revenue a month. I think we were pretty honest with ourselves in that we're making progress. I felt like there's a there there.

30:42I'd probably just gotten there. It'd been 18 months, almost two years. And it was like, gosh, I've just spent so much time not making the progress that I want to, but enough that it was like, I think I'd gotten over that mental hurdle of like the feedback we're getting on the product is really strong. And even though like I can't perfectly connect that with like commercial results yet, my intuition from kind of feeling that energy is positive enough that I'm committed to this. You know, I think I would attribute some of that, you know, it wasn't quicksand because we've doubled every year, But it wasn't like this meteoric rise either.

31:23And I think some of that was probably just hesitancy to invest in things and not knowing what to invest in and what's going to work and what's not and what's good money and what's bad money. And I think every entrepreneur goes through that every day. Unless you've started five businesses and you're heading into your sixth and it's a category you really know. I think for a lot of us, there is a lot of that uncertainty. And yeah, gosh, I feel bad about your honesty about some of my criticalness. Dude, I rated it. Can you be skeptical? There's a lot of stuff out there. There's a lot of people making a lot of big promises.

32:02And we weren't. But like, yeah. No, you weren't. But I do think like you do get into this like, hey, my email has been hijacked daily. I'm getting offers, you know, agencies are reaching out and pitching things and you start to see the themes like, oh, I guess the theme of this month is like this headline. And you can tell it's an agency trying to like bait you into like, oh, my gosh, I need them. And so like, you know, part of a small fraction of a founder's job is just like sifting through this noise and, you know, going through and deleting a lot of these things. And so, you know, you're naturally going to test a few things.

32:42And I think for the most part, I've tested things within the community that I have so that it's there's a referral, there's somebody who knows some of their work or whatever. And I think that's helpful. But yeah, I think when I talked to you, I was like, I really like the philosophy and the approach and the backgrounds of the team that you have, including yourself. But there's a bit of skepticism about outlaying cash for something that a couple of months down the road, I'm like, gosh, there's another quarter gone. And you've seen the results. Obviously, you guys have access to it. We've been very fortunate in terms of the combination of some of the work we've done in the past, kind of leading into these last three or four months, combined with the support and the coaching and just the interactions that I've had with the team at Founder in terms of those two things coming together, I think, in a really powerful way.

33:35And certainly we've, the last three months, we were on a run rate to do seven figures. Our growth has been really solid. But what I would say is like, you know, revenues is not the best metric for a business. And what I would say underneath in terms of profitability, traction, you know, growth of sort of how I'm thinking about margin and sort of bottom line is as exciting, right? that the work that we're focused on is really, you know, sort of the underpinnings of a very successful business as we continue to scale. And, you know, I think a lot of that has been some of the opportunities I've had to kind of connect with the team.

34:14And honestly, I would say I'm probably, I'm like one of the worst case studies in your group in a lot of ways, because I've been doing one or two things at a time. Like some of the cohort that I have is like, how are they doing that they're working on like 10 different things at once. And I feel like I'm probably still almost just scratching the surface just because like Nick was my coach. And it'd be like, dude, like, I'm not as smart as some of these people. Like I need two things and I'm going to get those done in two weeks. And then I'm going to go to the next two things. And that's been really successful for us just because the things that I worked on were definitely big priorities, things that I felt like And Nick felt like would really move the needle.

34:54And we did them right. You know, we did them the way that worked for our brand. And so we were not doing things scrappy. We were trying to do it right and once. And those things have definitely paid off. Yeah. So like, let's talk about that. So when you came to us, from memory, you had been burnt by an agency, I think, right? Everybody's got a couple of agencies that have not worked out for one reason or another. And honestly, like there are folks in founder that are, have moved the needle even farther in terms of like truly taking everything in house, mastering it all themselves. And I think I had this conversation with you and with Nick early.

35:32It was like, I totally appreciate that. And I think if I were 25 or 30, I, I would probably approach that too, but I'm also a dad of two and, you know, have other priorities. And, and so I want to be efficient, but in certain places for us, it may make sense to have an expert on the other end or fingers on keyboard for certain things, just so that we're moving at full speed. And those are the choices we made. But what I will say is like, we haven't done a whole lot with actual like creative for ads. So we still have like a whole chapter to go through. And we've made progress there just from the learnings I've heard from other people and applying things behind the scenes.

36:12But like where we really dug in was focusing on the right metrics, You know, drinkware is a unique space, right? It is not something you're going to replace every two months if you build it well, you know, for sure. It's not a super high AOB product per se. And so like really kind of zeroing in on CLV or customer lifetime value and our CAC and just obsessing that and kind of like almost teasing that equation apart and being like, what can I do on this side and what can I do on this side? And we actually focused on the numerator probably a little bit more than most people is like, how do we obsess AOV?

36:49And we really like dug into the website and kind of said, what is the consumer experience we're delivering? And how do we really connect people to the idea of like buying pairs or bundles or packs as a part of the buying experience? Like if I were buying drinkware pre-Summit, I would have been like, oh, I love this, but I might get one for my wife so that we have different colors and she knows which one's hers and which one's mine. We kind of really dove into that experience a little bit more. How do we think about repeat customer rate a little differently? We drive a portion of our business through a very kind of unique limited edition program.

37:27And so there's ways for consumers to almost like be able to collect or have a couple colors that are truly limited. We only make a 980 of our limited editions. And so we've really worked on sort of how brand consumer experience, the website play a role in thinking about that equation that we talked about really early on. And I think that was an unlock for us in some ways. And now we're pivoting and we're kind of focusing on the denominator and like obsessing and volume of creative for ads, type of creative that works for our brand. Like we want to present a really aspirational lifestyle a, you know, in a lot of ways, tapping into what I was talking about, where the founder story was, like, how do we share that emotional space of, you know, a lifestyle that we all aspire to and not, none of us are living it every day, but how can we help be the passport or the conduit to that lifestyle?

38:20And how does this product represent like a, almost like a feeling, right? And so like, we're working on advertising. It's probably different than a lot of folks. Like, Like, you know, it's not a lot of sales. It's not a lot of, you know, speeds and feeds. A lot of it is like, how do we convey this feeling, this emotion and get better at it? And so we're kind of, we're working on that side now a lot more in terms of improving, you know, the performance of ads. But at the end of the day, really, like, how do we just convey our brand in a better way and share our story in a better way? It sounds like, um, some of the stuff where Nick is massive on his AOV maximization bundling and offers.

39:01And that's, that's, that's where it's at. It is so incredibly important. And it's part of like, if I look at every single person that is crashing it in operators right now that have had incredible growth, it's offers, it's AOV maximization, it's conversion rate and then really juicing up that AOV, getting an offer going and then cranking the creative, the spend, even building the trust. You talk about the numbers, building the confidence in the numbers. For some people, they had actually the, all the makings there to scale. They just didn't have the confidence in the numbers. And it's just us looking over your shoulder, tapping you saying, yep, it's okay to scale.

39:43Yep. Increase the budget by 10%, jack it up by 20%, jack it up, check it up, check it up, and then just watching it hold. Or even maybe returns going down a little bit, but we don't care about returns. It's just about contribution profit. That's all that matters, which I know you respect, right? It is unlike, I think there is some benefit just purely to the confidence of talking to someone like yourself that's been in our shoes. You spent some time in a category that's very similar to mine. Nick has as well, right? Like, you know, he's an adjacency in the beverage space and is thinking about a lot of the same problems.

40:20And I think they're looking at the same numbers you already were, but they're being like, dude, no, like we're going. And I think that does, you know, there is, there is a benefit beyond just, you know, the, the content and, and how we're thinking about things that is different through founders, but, but even just having some of those experts in the room and being in your corner, it's worth calling out because it is meaningful. And so I, you know, I think that's been amazing. And then I think about like, I knew how to source product. Like I knew a lot of the stuff, but like sitting down with like an Owen and, and going to your website and, and even some of the stuff wasn't like, this is brand new.

40:58We'd have been thinking about stuff, but it was just the push. Like he was like, Jamie, for your brand, everything needs to be cinematic. Get to stunning imagery. Make sure the lifestyle, the experience of your brand is conveyed in the right way. I'll give you an example of somewhere we invested heavily, and this was also driven by somebody we brought in for our brand who's been amazing. We went to CGI, effectively CAD drawings of product. So digitally recreating our products so that we could get to super high fidelity of the details. Like we have like knurling on our lid, but it didn't show in photography, right?

41:38We weren't showing the level of detail of our products. And so both in terms of, of product photography, but also in terms of what recreating it in CAD allows you to do in terms of motion, right? Like showing the lid coming off. Your PDP is quite good, dude. I'm looking now. So, so you, you made some changes there. We, we made a bunch and I would say, you know, initial driver was Chatham runs, uh, is our, our brand lead. And he'd come from a brand that was a DTC success that was industrial design based. And he had some of these, these ideas. And I was like, that's like real honey, right? Like that's, that's an investment.

42:14He was like, trust me. And you know, the combination of him with some of my founder advisors, like Owen and Nick, they were like, absolutely. Right. Like, cause of, of how you want to build your brand. Like we, we want to create an experience and I'm not sure we were fully delivering that even though the product lived up to it, it didn't show up on the website. And it was so obvious and I, and I knew this, but, but, but those, you know, birds on my shoulder, those, those voices, you know, made me like face that like, Hey, this brand is not well-known nationally. Consumers are new coming onto your website.

42:54The experience you delivers is almost everything because they're just meeting you for the first time, right? And so how we show our product, what kind of video we use, how a page is laid out to truly showcase what an aspirational lifestyle through the lens of Summit can be, even how we convey storytelling messages, right? I told you almost everybody on our brand comes from this active space. Me from Nike, We have a team from Smith Optics and folks that have lived this athlete lifestyle. And we love that, right? That's a personal part of our background and our passion. And we believe like for consumers, it's a great lifestyle to be active and outdoors.

43:33But our unlock for Summit is we're not making this for you to run with it. We're making this so that when you ski, you've got an amazing coffee before or hot chocolate after or a cocktail after. And so our emotional space is really those moments of pause, right? We are all so busy and the world is stressful and we don't even need to get into that. I think everybody understands that. But this combination of active lifestyle and these moments of pause that the drinkware can bring you to, to us is the truth, is the answer for having an incredible life. And so how do we convey that on a website? How do we visualize that?

44:12How do we storytell that? And that's a lot of the challenge that we were pushed on over the last few months was like bring that to life in a way that people can resonate with and can feel for somebody who's taking a shot on your brand, who's seen you on Instagram or whatever, and it's coming for the first time you have to deliver that. And so I think we spent a lot of time there and that's really helped. And you see that in the numbers, but I think, you know, a lot of times people think like just offer, and then you're going to get numbers. And it's like, no, think about the true consumer experience that you're trying to deliver for somebody that you're inviting in and trying to build trust with.

44:52So it's all those things kind of working together, like incredible product, incredible website experience, or if you're in retail or omni-channel, an incredible retail experience, all leading to then some of the best practices of a PDP and a checkout experience and all that stuff. So from what I'm hearing, what was the big driver for you to effectively pretty much double, if not close to triple these past three, four months was a combination of things. But one of the levers, the two levers was increasing conversion rate and increasing AOV and traffic, but not as much. You haven't really started with traffic yet that much.

45:26Traffic has increased in the last three months as well. Some of that, you know, because another thing we worked on was like drinkware is also a very kind of launch driven, color driven category. And it's a great mechanism for storytelling, right? And so we have increased our ad budget and increased traffic. I would say it hasn't been as significant a focus for us in terms of like the one-to-one coaching and where we put the most energy and time, but it has happened. AOV was probably the biggest, like just unpacking how we could really drive AOV in a more meaningful way was probably the biggest.

46:08And it led to a lot of those, the things that we were talking about, right? Like the website experience that we delivered, but also like layering in, in that consumer journey, a better bundle experience, making it easier for consumers to be able to shop in that way. So the combination of delivering like better storytelling combined with like some of those, those paths were, were investments we made to make the experience more efficient and just better for the consumer, just trying to deliver a better website experience for the consumer. Yeah. I'm looking at your website now. I love the personalization element.

46:41You automate that from your 3PL? We actually have a second 3PL that does that. So we actually have two warehouses and we added the second warehouse specifically to add personalization. And that's a great example of one of the things that we layered in right at the beginning. So we'd already been working on that. I love that because from a consumer perspective, just layering deeper meaning into your product is powerful, right? It's genius. I wish we had it on that. Just simple monogramming or putting a name that's meaningful or being able to gift something more special is really powerful. And to our previous conversation, it is also an AOV builder.

47:23And we do the same thing. We have a program called Lab. We love working with other people outside the brand that have a creative point of view. And Lab is our mechanism for that. So it's a graphics program and we create art and we do that through the personalization 3PL. So it's built on demand, but bringing creative voices, cultural voices in and having like a month long program where a piece of art is available on our drinkware is just another way of like telling our story, sharing somebody else's story and bringing them into the brand in some way. but also just creating kind of unique one-off pieces that feel more special to the consumer.

48:06It's really clever. So I'm just going through the checkout process now and we've added, you know, we've added$15 for personalization. That's good margin, man. Right. And it's just a, it would be just a screen printer going through it. And then, you know, I'm$18 away from free shipping and then I've got the bundled tumblers and save. So then of course, you know, I want to buy one for my partner. And so yeah, I can see how it, um, yeah, it's really coming together. It's really, it's really awesome, man. You've done a great job here. Oh, well, thank you. It's definitely an unfinished product, but every day as an entrepreneur, you're just trying to put one foot in front of the other first and then take kind of one step forward.

48:43I think just almost unrelated, but something to share with people who are going through the journey and taking this step for themselves is like entrepreneurship is not linear. It does not feel like progress every day, right? you take two steps forward and you might take four steps back. What's important from a keep going perspective is what I've found is when you look at it in longer terms, like if you look at it over two months, you can see the progress you've made. Sometimes it's really hard to see in the moment or in the day. And so like, just pull up and like, know that you're, you are making progress.

49:18Cause there are days where it's like, wow, I went backwards today and I'm not even sure why, but you know, I'm going to unpack it. And 10 days from now, I know I will be farther than I am today, but tomorrow may not look great. And that's a little bit of the game is you have to have the grit and determination to just keep marching because it is not linear at all. Yeah, no, I agree. You're bringing me back to a conversation that I was having with one of my mentors. You know, we have multiple memberships at Founder, levels and all sorts of things, right? And for where you're at with your brand and uh one membership in particular we really went backwards these past three four months and and like i was telling my mentor and and he was telling me this story that like sometimes we just like really try and over optimize things in pursuit of growing it and sometimes you do not need to complicate it and i like complicated the absolute crap out of it like my head of product gave me this idea i'm like you know let's do this and layer these other things on from a strategic standpoint and then before we know it it's like oh my god we've changed so many things we've fully fucked this thing up it's not it's not it's like it's going backwards i'm like oh my god and now it's like getting it back and like we've lost three months of growth and it's just like oh now we just need to get it back and now it's taking three four months of like working it out and now it's getting back in line but like yeah it's and that was all in for pursuit And then I tell myself, well, what if I just didn't touch it and just let it grow organically nationally?

50:49Like I didn't have to try and, you know, increase growth by 25 % month on month by doing these other things. Like I just didn't have to do that. I could have just been patient and just left it alone. And so, yeah, it's funny how, you know, when things are going good, it's just like, well, it's only natural that I want to change it and try and increase this growth faster. And then sometimes you go backwards, right? It's only natural, right? Yeah. Well, and to some degree, it's like, how do you just continue to learn? Right? Like the growth mindset is all about learning. And it's okay to make a mistake.

51:26It's okay to pull the wrong lever. The problem is if you don't learn from it, right? Like you keep doing the same thing or keep pulling levers or not learning the lesson. And that's where you really get into trouble. And, you know, you know this, right? Like it is not perfection. It is gritty. You got to keep kind of pushing forward and yeah, make mistakes and that's okay. But learn from them and then, and then keep progressing because, you know, grit is, is by far the most important attribute in this space. And grit in some ways does not define perfection. It's just truly being able to grind through, learn from where you've, you've made the wrong pivots and continue to kind of move forward and make decisions from there.

52:10So I can't remember who said it, but somebody said your ability and your capacity to handle stress and pressure will be unfortunately one of the biggest determining factors of how successful you will be. I think that's true. I, cause honestly, most businesses do not fail because the idea was bad. You fail from lack of conviction. you fail from not understanding cashflow, which I think is the biggest failure point. And yeah, I mean, the ability to manage cortisol levels sadly is an incredible barometer of startup life. And it's, by the way, it's not for everyone. It's okay to not be an entrepreneur, right?

52:55Like, in fact, it's not what I would guide for the vast majority of people. but if you love kind of risk reward it can be a good fit for the right right personalities and i'm still trying to figure out if i'm the right personality for it it's gonna keep building man it's coming together it is we're we're making progress and and a lot of that thanks to you guys and and so i can't can't thank you enough it's it's it's been a fun you know three or four months you know and seeing the progress is fun and and like i i've gotten a few notes from you You're like, hey, dude, like your last month was really good.

53:30And I was like, dude, it's only like half of what I really want to do. And so, you know, there's always this balance, but I appreciate sort of the pat on the back every now and again. Oh, you're welcome, man. Well, yeah, look, dude, progress is happiness. It's been incredibly inspiring to watch your journey from afar since we've met in March. And I feel like we're only scratching the surface. we have our in-person event for our black friday planning boot camp all that good stuff unfortunately i can't make it because uh i'm getting married but we we do two to three events in person a year thank you but look man we're gonna help you just like absolutely crush last year's black friday if you are doing one i assume you are like most most brands yeah we will we we tend to lead with new product launches.

54:16So our probably top two things will be newness. We will have a sale going on, but it'll be a touch more tight than probably some most brands. But man, do we have ammunition for Q4? Like we have some really, really exciting stuff. We haven't had a new drinkware product in a long time. We do this Q4. So we'll have plenty to talk about and plenty to plan and prep for in LA in the coming weeks. So we're creating this like workbook that you guys will fill out. So by the end of it, you know, your offers, the timings, when to run ads, how to see all these guys. Like this is going to really pull out the blueprint for million dollar weeks.

54:57I was going to say, I'm already ahead of you. I've got the Q4 plan already started. Oh, how good. How good. How good. Yeah, yeah, yeah. So man, it's going to be epic. Like, yeah, we want all of our members to beat last year's Black Friday. and then we take all of those learnings as a group and then we come back again next year and like share them with the group it's going to be awesome and we just all want to keep beating yeah so like i don't know if i even told you this but we did a study from the first cohort because because we have read only access to you guys numbers and we can see how well everyone's doing and on average our members from the first cohort so there's about 30 of you guys on average revenue was increased by 23 % over that period.

55:37It was pretty cool. That period was from March to June. So it took December, January, Feb. So the Q4, there's a little bit of Q4 in that. So the growth would actually be probably understated as a comparison. And just to provide a kudos to you guys, I think we're somewhere in the 80 to 100 % growth range. I haven't looked at the quarter because I've been looking mostly at year to date. And I know we're up like almost 50 % year to date, But our Q1 was definitely not as high a growth as since we've joined Founder. So we're probably in that 70, 80, 90 % growth range for that time period. Yeah, no, man, it's been awesome to watch.

56:16So, dude, we have to work towards wrapping up. We could talk all day and talk about business and D2C and drinkware and this whole space. But I want to be mindful of your time. I want to be mindful of our listeners' time. We usually go for about an hour. So any final words of wisdom that you would like to share with our listeners, our community at large? I hit a few of the ones that I think, you know, the rock and chair test and making sure that it's something that you love and truly want to do. Because it is a massive commitment, you know, that grit is something you know and cortisol management, as we called it, I think.

56:55It's just something you have to know going into it. But I think maybe the only thing on top of that is like, just like a little bit of a mindset, which is truly the passion for it, like loving what you're trying to solve. You're kind of almost like a operator on behalf of consumers, right? Like you're truly trying to solve something for them, a problem. And so you're like consumer number one in a lot of ways, but really finding the joy in that, you know, like it is, it is really hard. I can't overstate how hard this has been. And I say that my 30s were spent running ultra marathons. I like hard stuff.

57:35This has been one of the bigger challenges of my life today. It's just extremely hard. But I think the reward of it is when you can find the joy in the problem you're solving and almost like the legacy that you're leaving, like bringing something to life in this world and sharing it with people, but really having that passion for what you're trying to solve and just reminding yourself that because it's super easy to get bogged down into the whatever it is. Yesterday, I spent a lot of time on accounts payable, and it's like, that is not what gets me up in the morning. And those are things that you have to do when you run a business.

58:10But if there's just a way for you to just have a almost like a daily reminder of like, how do I pull out for just five minutes and remember like what I'm solving and why I love that, you know, the joy of it comes to life in a much more meaningful way than if you get sucked into kind of the day to day, which is, you know, is a lot. And so, you know, if there's a perspective shift that I can offer to folks, it's find that way to channel that for yourself because it's easy to lose, particularly if you bootstrap it and you're playing the long game and you're not necessarily seeing the meteoric rise from day one.

58:46That to me has been really helpful in my journey, at least. Well, thank you for sharing, Jamie, and thank you for taking the time and congratulations on all of your success thus far. I look forward to continuing to watch your journey and support you every step of the way, even if it's behind the scenes where, yeah, we're, we're loving the progress you're making, man. And, uh, we've only, thank you for the kind words, but we've only played a very, very, very fractional part. Like you've done all the work. This is your brand. Like we've just kind of helped you very, very, very lightly from the sidelines, man.

59:20It's all you. So congratulations on all your success thus far. Let's, uh, make sure we just keep growing this thing. Yeah. Love it. Appreciate it. And thanks so much for the time. It was really fun to catch up and chat for a little bit. Hey, Founder Fam. Thank you so much for tuning in today. And if you enjoyed this episode, please take the time to leave us a review and let us know what you think. This podcast is 100 % free. We work so hard to go out and find the most successful entrepreneurs and founders in the world. Your feedback helps us grow, improve, and even bring on more incredible guests and insights.

59:54So if you have a second, please take a moment, leave us a review. It really makes a difference. Thanks again for listening and I'll catch you on the next show.

From the publisher

Jamie spent over 20 years in corporate America, including a stint as a Nike executive, before a barbecue accident changed everything. Hosting friends and family in Park City after a near-perfect day outdoors, he tripped and sent a tray of drinks flying over everyone. That clumsy moment sparked two ideas at once: a better, genuinely leak-proof product, and a brand built around the outdoor-lifestyle-and-moments-of-pause philosophy he and his wife Michelle wanted to live by. He funded SMMT Outdoor entirely himself, went all in from day one, and spent nearly two years and 50 prototypes getting the product right.

In this episode, Jamie is refreshingly honest about the unglamorous middle of the journey - the weeks with one or two orders, the pivot away from the category he launched in, the agency burns, and what it actually feels like to go from leading teams of teams at a billion-dollar company to being a solo operator with one contractor.

What you'll learn in this interview:

The barbecue accident that sparked the whole brand - and why Jamie built SMMT around an emotional "active days and moments of pause" philosophy, not just a product spec

Why he launched in bags first, then pivoted to drinkware after 18 months and 50 prototypes - and how that detour taught him the business he actually needed to learn

The reality of the early days: weeks with one or two orders, days of "crickets," and the humbling gap between corporate experience and blank-page entrepreneurship

Why he chose to bootstrap with only family capital - keeping the cap table simple, feeling the pain of his own money, and buying himself the freedom to make long-term decisions

The "rocking chair test" he uses for big life and business decisions - fast-forwarding to age 80 and asking what he'd regret not doing

Why he deliberately built for a sustainable family business rather than a unicorn - and his case for why a $10-20M brand is a huge win nobody talks about enough

The Thanksgiving dinner spent refreshing Shopify to see if the drinkware launch would work - and why 25 sales on day one felt enormous

The exact equation he obsessed over instead of chasing revenue: customer lifetime value over CAC - and why he attacked the numerator first through bundles, pairs, and a 980-unit limited edition program

How a $15 personalisation upsell, print-on-demand art drops, and a rethought checkout experience quietly built margin and average order value

The hard-won mindset lessons: entrepreneurship isn't linear, most businesses fail from lack of conviction or poor cashflow rather than bad ideas, and "cortisol management" is a real barometer of startup life

If you're a corporate operator wondering whether your experience actually translates to building something of your own - or you're bootstrapping slowly and quietly, doubling year over year without the meteoric rise - this episode is for you. Jamie's story is a grounded reminder that deep patience, obsessing the right numbers, and genuinely loving the problem you're solving matter far more than a fast start.

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