ECOMsquare Overshare Podcast

The Founder's Mentality

In this episode of The ECOMsquare Overshare, two ecommerce founders talk about the unique pressures that come with starting a business, and how the dark times they've faced have shaped their business mentality.

Podcast Guests:
Haruki Nakagawa - ECOMsquare Community Member
Nicole Murphy - Co-Founder and CEO of Tall Size
Rob Fraser - Founder and CEO of Outway

Introducing Today's Guests

Haruki: Welcome to another episode of The ECOMsquare Overshare. Today we're talking about the founder's journey and especially how to deal when that journey gets hard. Joining me today, we have two eCommerce founders. First, Nicole Murphy, the founder and CEO of Tall Size, a tall women's clothing store. Hello, Nicole, how are you?

Nicole: Good. How are you?

Haruki: I'm great. So, to fill the readers in a little bit, you're the one that actually provided the impetus for this episode to happen. You shouted out into the void of social media to find something that you could not find. So, why don't you help set us up a little bit. What were you looking for? What caused you to reach out?

Nicole: So, we're about a year in to our business and it's tough; it's a grind early days. I'm always listening the podcasts of other founder stories, but one thing I was craving is - it was always success stories. It was always a quick little tidbit about, yeah, it was hard in the beginning, but now we're the massive company and everything's great and whatever, right?

There's a lot of success stories, but I think because of where we are at in our business, I was just craving some...some dark stories, you know? So I didn't feel so alone in the grind that is starting a new e-commerce company, especially in today's day and age.That's where it came from.

Haruki: Totally. So, I saw that post on LinkedIn that you put out there, and as part of the team at eCommerce square I saw your call for help, I thought, "Let's try to find some community for her!" So, we went into the ECOMsquare Rolodex, and came up with someone who I think is perfectly suited to the conversation. He is our other guest today - Rob Fraser, the founder and CEO of Outway socks, coming up on your six year anniversary as a company pretty soon here. Congratulations and welcome, Rob! Thank you for joining us, how are you?
Discover modern coworking for ecommerce brands in Vancouver at ECOMsquare. 1758 West 8th Avenue.
Rob: Yeah, I'm doing well. Thanks having me excited to chat today, and I agree. These are stories that need to be told and it'd be fun to share.

Haruki: Right, it's such a thing with social media, everyone's talked about it a million times - you only see the sanitized, the best version of everybody and everything - so when you're going out there trying to find some help, especially, it can be really demoralizing.

So, I want to start with Nicole. You reached out. You wanted these conversations about darker times, how do you deal with that kind of thing, etc. What was going on that made you seek that out? Can you talk about what was happening?

Nicole: Yeah, I think in the stage of our business right now, we know we're onto something. We're getting all the feedback, all the signs, all the data telling us that...and I think that the dark moment, I guess if you will, is I was just thinking to myself,

"How the hell do people build their businesses in the early days, with no money?"

We are completely bootstrapped. We've invested some of our own personal life savings, but there's not a huge influx of capital that we can use to tap into. And so I think when you see a lot of these success stories of all these companies, raising all this funding and doing all these amazing things. That's cool because you have the funding or you wanted the funding and whatever you went for that, but what are some more like practical ways?

What was it actually like in the early days? Were people dumping their whole life savings into it? And what did that feel like? Because, how scary is that, right?

I think those are some feelings that come up as founders that, um, you feel really alone, because it's scary to do things like that. And so I think just, I was craving conversation from others who are in it, or who actually spend time reflecting on what that really was before they had their big unlock, whether it's funding or whatever it ends up being. But, that's really kind of the head space I was in. I thought, "God, there's so much I want to do, but was getting really frustrated on the funding situation.

Haruki: Rob, if you could think back to early days, about Outway (at that time Endur) and if that came up for you and how you dealt with it?

Rob: Yeah. So we were bootstrapped as well, for five years. We raised money in the fall of last year, but bootstrapped to, you know, multi eight figures in sales before raising money. So had to kind of go through the same dark times of, you know, how do we fund this thing? And where's the money going to come from?

When I started the business I was in school and in student debt, money. So to initially fund it, I put in a thousand dollars from school loans, which basically meant that I wouldn't be able to eat as much that week, or you know, go out on the weekend or whatever. As I needed more money for living, because of course you're not paying yourself, I basically tried to start selling things I owned. I've talked about it before, but before starting a business I was a competitive elite cyclist, so I had a bunch of bikes that I really loved to ride. I sold them all.

I sold them all to basically live. That's maybe one of the dark sides is that basically for almost three or four years until I could afford to buy bikes again - luckily the business did well and I could buy bikes again - basically couldn't even do what I loved to do. I couldn't go ride my bike anymore. People would always ask me, "Do you still ride bikes?" Like, no, I sold them.

I sold three or four at that time, but they were expensive bikes. That's how I could basically fund myself and basically live while I'm putting everything I have into the business. And I was also working on top of going to school and starting the business. I was working a few different jobs, like part-time stuff just to generate more income; I live in Victoria, BC, and it's not cheap to live here. My student loans just covered the actual school tuition, it didn't cover living expenses. I didn't have the qualifications, I guess, to get more than that.

Luckily though, early on, we kind of stumbled into a way to use our business model to actually generate additional income by creating white label products for other brands. For example, we sell socks and then one of my old sponsors from cycling said, "Oh, I see you're making socks now, could you make them for our brand?" And it was kind of a light bulb moment of, "I guess I could." The benefit of that model was it was cash front and then we'd produce and ship. So it generated a lot of free cash flow and there wasn't an inventory risk. So that's really how we funded the company in the early days.

So what I say to founders earlier in their journey looking to generate funding is:
Is there other ways you can use the business you've created and then generate additional income streams? If there's ways of doing different iterations of that business model, in a way that doesn't devalue the core brand, which is obviously super important.
For us, we became experts at making a product and other people needed the product. That was how we generated cash flow in the early days, with a kind of white-label product. Otherwise there was no way we would've been able to bootstrap to the 10 million mark. Just the inventory demands and marketing demands to front-load the growth are just way too high.

Nicole: How long did you go?
How long did you go before you started actually paying yourself?
Because I think that's the other struggle too, especially for my story anyways, is I come from the tech space where I was making really good money. So I made that jump, right? And doing consulting to pay my bills and not have to dip into my savings quite as much. But, the other big question mark to me is how long do people actually go before they start paying themselves? At what point did you make that decision that you wanted to not siphon all the money back into the business, but start being able to pay yourself as a founder?

Rob: Yeah. That's something that's going to vary based on each person. In our first year we ended up doing $350,000 in sales, so it started to do pretty well and we kept the operations super lean and we were quite profitable. So in my case, I was able to pay myself $36,000 that year. It's three grand a month, basically. So really not a lot, you know, after taxes come off. So that was basically just to stay alive.

I think the push and pull here though is a lot of founders think that they need to put every dollar into the business, but your sanity and quality of living - not saying be extravagant - but you are the product as well.
You're the most important thing in the business as a founder in the early days.
And if you're not optimized, if you're going to bed hungry, or if you're really stressed and, and, and not functioning at a decent level, then I would kind of question whether or not you're making the investment in yourself as well. You are a part of the business, so I don't think people need to look at paying themselves as an extravagant. Thirty-six grand is not a lot of money, but it put food on the table and you need to eat.

My other way of looking at this is entrepreneurship is like a sport and you have to treat yourself like an athlete.

Part of that is you need to be able to give yourself time to exercise. You need to give yourself time to rest. You need to be eating quality food, because these things are all important, and business is so difficult that if you're not doing these things, the path to burnout is much shorter than if you were to be taking care of yourself.

I would just say if there is a point where you're making some money, you want to be taking a little bit out, because you have to recognize that an investment in yourself is the founder is equally as important as an investment into marketing channels or more product development, because you are literally basically doing everything. If you're not functioning at the highest level, then I would always kind of push back on a founder ask: is your business really going to make it? For a lot of startups and founders and businesses in the first few years, the success is just on the grit and is the founder willing and able to keep going and roll with the punches? It's not generally their genius, or the product, or anything like that in the early days. It's really can you stay alive long enough to make sense what you're doing? Once you do, then you can actually start to grow.

Haruki: You touched on self-care there a little bit, which I would like to talk about. You talked about the basics of eating, sleeping and hopefully, Nicole, you're getting that done! Moving on to your mental state, Rob, do you remember,
What was really important to get in the right mindset, and stay in the right mindset?
Rob: Yeah, I wasn't probably the best at it, honestly. I came from the professional athlete world, so pretty hard charging and didn't take a lot of downtime. I'd say the thing that actually caused me the most stress was I had a co-founder that just wasn't the right fit for me. When we started the business, I started with a friend in college and we didn't really expect it to work. I knew I was going to go and try my best, but I had never started a business before, and it was really just something to do while in school to keep myself busy, because I wasn't satisfied with normal life after being an athlete for so long. School's boring. I want to try something really big, and I thought it would be more fun with a story's not as important as kind of the message, which is:
In those early days surround yourself with people that you can really get into the trenches with.
Luckily at that time I had my girlfriend, now wife, and so she was super helpful, just to chat through things or whatever, because, you know, what Nicole mentioned early on here is that it's a very lonely journey as a founder. There's other people building businesses, but in the early days in your business, you're trying to create something new that hasn't previously existed, and so your problems - although there's some similar things and probably what I'm talking about right now, Nicole's had the same feelings - the buck stops with you and you have to ultimately figure out all these different things that are quite unique to your business, and that are really unique problems to you. So you can get lonely.

So I'd say I didn't have the right co-founder and partner in the business. That caused a lot of trouble. I just felt overworked And there was just a lot of tension. Like I mentioned, I had to sell everything to stay alive and could only take so much money out of the business while I had a co-founder that was living at home and didn't have any expenses making the same amount of money, and then also wasn't doing the work.

That caused a lot of resentment on my part, because I'm already doing everything and I could make double the money, because I have someone else who's not struggling as hard as I am. You know, he was five years younger than me and I wasn't from Victoria. So I was paying rent and groceries. In that same period where I'm literally in debt, he bought a truck. I thought, "This sucks. This really sucks."

I was though, "What's the point?" And that ultimately ended up in me deciding I'm walking away or buying my co-founder out. This is not an uncommon thing in business.
People start businesses and a lot of people ask themselves, "what happens if it goes wrong," and they optimize for that by minimizing risk, but don't ask themselves, "what happens if this goes right?" and making sure to optimize for that is even more important.
That's really important because that's almost the worse situation to be in, where something's working and you didn't think through how to capitalize on it. Unfortunately, I didn't really ask myself thoroughly or think through what happens if this works, even though I truly thought it could.

So, yeah, that [co-founder issue] was probably what caused a lot of issues. The actual work itself and the struggle and stuff...I came from a 10 year background of dealing with a lot of adversity. Professional sports is not easy, and there's a lot of ups and downs. And so I built a lot of mental strength in that area. But, what was new for me was dealing with a partner that wasn't pulling their weight and all of that set of things.

So, the long-winded answer there is making sure you have the right people in your corner with the same values and motivations.
It's truly like a marriage for co-founder relationships. And if you have the wrong dynamic's one of the key reasons startups fail.
Nicole: Mm-hmm, I've also noticed myself, just forming relationships with other, in my case particularly female founders, who are at a similar stage as me has also helped this whole not feeling so alone thing? Like, what is this journey? It's wild. So that's actually been really helpful for me: expanding that network of people who are on the ground, figuring out this stuff as much as I am. There's obviously the support component of that, but also just learning from each other, right? They might make a mistake that could save me that mistake just by being surrounded by people like that. So I like that you said that, because that's a recent realization for me, I would say in the last month or two, how incredibly important that is.

Before that, a lot of my friends and even my family, they don't get it. They don't get why. They're like, "Why are you doing this? You had a great job, just keep working the job." And so I found that also quite isolating. It's been good. Just finding people who are kind of down there with you.

Haruki: Totally. And that community is out there.

Nicole: I just wanted to ask Rob a question: you talked about balance, and as founders, you're one of the most important assets to the business, invest in self-care and all that kind of stuff. I would say, generally speaking as a human, I get my eight hours of sleep, I eat well, I exercise, but I do find myself, thinking about my business. All. The. Time. To the point where I'm thinking I need some more hobbies or something; I need something to get my mind off of it a little bit.

I'm so passionate about what we're building, that I'm thinking about it every waking hour of the day. I almost wish that I had a bit of an outlet, or something. Kind of just to distract my mind. And I don't know if Rob, you went through that or if you have any learnings on your side of how do you think about things other than building your business to get some mental rest and some better balance on that front.

Rob: Yeah, I don't know, I think that's kind of the curse of entrepreneurship. There's not much of a way to get out of that.

"I don't believe in balance for entrepreneurs as much as I believe in finding synergies."

So, finding things that allow you to still work on your business, but maybe it's context shifting, is good. I'll go for a run or a bike ride, and I will, my mind will drift. I'll still think about the business, but it's a little more the creative side of it, the things that give me energy.

It's just a question of asking yourself, "What parts of thinking about the business give you energy and what parts take away energy?" Then, optimizing for the downtime, at least only focusing on the things that fill your cup and give you energy.

Just turn off the negative thoughts. If you love what you're doing, there's probably zero downside to thinking about it. Then, just in the times where you're not working, or at the desk, or plugged in, if you see your mind drifting to the things that are anxiety inducing or whatever it is, be like, "Well, this is not the time." I just try to bucket it and actually think of putting it in a little bucket and this is going to the back of the head till we go to work tomorrow.

Because this is not an issue I need to deal with right now, and I literally can't deal with it right now. It's kind of that concept of worrying about things in the future that haven't happened yet. What's the point? You're suffering in advance for no real reason.

So, I'm not perfect at it. I'm always thinking about it too.

I'd say maybe the only thing in the last six years that has ever turned it off is I had a son, and sometimes I'll be watching him play and that's all I'm actually thinking about. That's the only thing though. And even then sometimes I'm not fully present, which I don't like, but that's probably the only thing, maybe because that's the only thing, one of the few other things, that I love more than the business. Other than that, as entrepreneurs, I think that's kind of the curse. There's no getting away from it.

I would say try to avoid the negative side of it though. If you don't have to/can't deal with something in that moment, then just be like, "This is not important to think about right now."

Nicole: Got it. Okay. Go have a kid. Noted.

Rob: Haha yeah. That brings its own challenges. It's like startup number two. They're absolutely crazy. It's been nuts, but it's fun at the same.

Haruki: And that's obviously something that founders more than most people are going to experience (difficulty separating work life from home life). Like Rob said, you are the business. And for you Rob, you're not compartmentalizing. That's not your approach, to find techniques completely shut the business off. That's not something you do.

Rob: I don't know. It's not my personality. I've always identified with what I'm doing. When I was an athlete, I was an athlete. Now I'm an entrepreneur and I'm an entrepreneur. I'm not saying that's everyone's strategy. I would say though,
If someone's getting into business and wants balance, I would say, don't get into business. Don't be an entrepreneur.
You wouldn't become a professional athlete saying when I get home from practice that day, I don't want to worry about stretching and doing the ice bath and doing the massage. All the things that suck. They suck. But you have to be doing it 24-7, because there's no alternative and it's the same in entrepreneurship. If you actually want your business to make it and be the top 1% of the 1%, you're an Olympian.

Do you think Olympians like Michael Phelps...he didn't miss a workout for 10 years, right? Like 10 years.

And so if people want to get into entrepreneurship and have balance, power to you, just don't expect that you're going to build the business that breaks through. You can build a nice lifestyle business that way, and I'm all for people that want to do that, but they have to be real with themselves. You can't have your cake and eat it too.

The number one thing entrepreneurs need to do is live in reality.

The reality is this is hard and it takes all your time and there is the dark periods and we can talk about them and have strategies to mitigate them and not burn out, because there's definitely time and place for that.

However, it's not balance.

it's just strategies, you know, just like athletes need to recover. Recovery's part of sport and they're doing it very thoughtfully. It's not just sitting and eating a bag of chips on the couch, or whatever. It's actually still work, but it's rejuvenative, you know what I'm saying? That that's how I look at it. That's why I say synergy over balance. If you're going to be in this game and you're going to be in entrepreneurship, it just bleeds into your whole life.

You just make it a part of who you are and you build strategies and you find time to be present with your partner, with your child, or whatever, but it's never off. It's going to be there, especially in the early stages, until you've got a team large enough where you can fully delegate things out and maybe step back a little. That's usually five to 10 years out from when you start.

Haruki: And that reality is so important for people to hear and I think understand the sacrifice that is going to be involved. When I was in university, I lived with an Ironman athlete, and I'd been an athlete in high school and obviously you know it takes hard work. But living with someone who's at that top level and seeing the level of sacrifice that goes into maintaining your spot's just more than you could imagine.

Rob: I think it's delusional. You have to be a bit delusional. And people will never know, people will never understand unless they've done it. And that's the thing: people want to be pro athletes, they want to be entrepreneurs, but they don't want to get up do the work, a lot of them don't.

The beautiful thing about these things is they're permission-less and you have the ability and the opportunity to go and do these things. It just is so hard. It's just incredibly hard, and a lot of people aren't willing to go through the suck for so many years, and the other dark side of it is the majority of the time it doesn't work out. It's the combination of extremely hard work and uncertainty can just be a dark place. But when it does work, it's great.

Haruki: So how do you find the limit of your hard work as a founder? Because I could imagine thinking to myself, you know, I'm doing enough, and I don't think that's healthy for the business, or I could also imagine thinking I always need to be doing more, and maybe that's not healthy either.
Is there a way you know you're in that sweet-spot of working hard, but not on a one-way path to burning out?
Rob: Yeah, that's a tough question. I think if you're a high performer, the default setting is that you're never doing enough. Ever. I've actually thought about this a lot.

I think as a founder or an entrepreneur, the expectation is that you're doing well from everyone else around you, except in your mind doing well means just meh, because you always want more from yourself. And then the reality is, things are almost never going as well as you want. So you're actually kind of in a low. So you're toggling between low and meh, never actually good, even though the exterior perception is that you're doing well.

And you can't really talk about it because, especially if you have be a modest level of success, everyone's like, "Oh, woe is me, poor entrepreneur that owns their own business and makes money," Whatever. But they don't get it. It's also really hard. And that's the benefit, Nicole, back to your point of having a network of other people going through it, because you can actually talk a little bit more and have a bit of empathy where you don't generally get it. Same thing as if you heard a pro athlete complaining, you might think, "Oh, poor you, you've got all these fans and this great life," or you hear about a celebrity that has mental health problems. People think, "Oh, why would you have mental problems?"

You have no idea the pressure they have. The average person gets nervous talking in front of a small group of people. Imagine you have to do that every day, all the time. These people are human.

Nicole: What you just said there lands, because the whole thing around as a founder, you're always feeling, "Man, we could be doing better," I found that challenging because, I just almost feel confused sometimes because it's, yes, we have accomplished a lot. I'm super proud of everything that we've accomplished, but it's so funny because I just see all the things that we have yet to accomplish or the things that I can't wait until we do.

Whereas sometimes when you're talking to people and they give you feedback, they feel like you've already made it and it's like, "No man, we're just getting started." So I've actually found that, in conversation anyways, to be kind of difficult, because you're right - you're not going to go there. You're not going to just start saying all of the woes and the things that you want to achieve, because it just makes you feel ungrateful, or makes you look ungrateful, or whatever. So, thank you for saying that.

Rob: Well, the problem - you can probably tell I've thought about this a lot - the other problem with entrepreneurship is that you're constantly living in the future. You have to be planning 3, 6, 9, 12 months out, maybe sometimes longer. For example, a few weeks ago we had our Black Friday meeting. So we're in November, in my mind, full on in November, December. And that's pretty much the shortest timeline I'm thinking right now. The problem with that is you're never enjoying the moment. Also, when you live in the future, it results in a high level of anxiety. If you live in the past, it's depression and if you live in the future it's anxiety, and the real goal to live in the present, but that's not a reality for entrepreneurs.

You're pretty much always living in the past, or the future. You're analyzing historicals and maybe depressing yourself a little bit, and then you're living in the future with what could be done and what you want to do.
So that's the other curse of entrepreneurship: it's hard to actually enjoy the moment, because how often can you actually really slow down and smell the roses? Not a lot.
I try to just have a kind of trigger to remind myself just recognize the wins when they come. Even if they're small wins, I think entrepreneurs and founders don't give themselves enough credit. It's always on the next thing. We made our first million bucks. Cool. What does 5 million look like? What's 10 million look like? What's 25 million look like? That guy over there is doing a billion, let's go for that. There's just never enough and you're on this hedonic treadmill. I'm just never happy, but life's pretty good at the same time.

You might as well just smile and be happy, but it's hard to remember to do that.

Haruki: So for both of you, do you find that your anxieties and negative emotions are coming from realities, or perceptions? Is it, you know, oh, this number is not good, and that makes me anxious? Or is it more the intangible things, the projecting and the future, how people are viewing your project, etc. What do you find?

Nicole: For me, it's both, if I'm being honest, it's both. In the moment I find that I want to be achieving more than we are in this given moment. I'm also a big vision type person. So I have no problem visualizing where we're going to be in 10 years from now. No problem. I could draw it out. I could spell it out for you. Where I struggle is working backwards from that and making sure we're making all the right moves now to get there. That's very anxiety inducing for me. It's so clear where I want to get, but I struggle in terms of how do we actually go and get there?

I think that's another reason why I wanted to have this conversation: is it the same thing for a lot of these hugely successful companies? You don't see the grind, you don't see the journey. A lot of the time people aren't documenting that quite as much as the success stories. And so the whole comparison trap of thinking, "This person's so big. I just heard about them a year ago." But if you actually dig, they've been doing this for 10 years or seven years or whatever it is. I get sucked into that a lot and need to remind myself to either go and do research and actually truly see where that person started out or where that business started out, or just trust the process. It's hard, I have to trust the process that we'll get there. But to summarize, I think both are kind of triggering for me.

Rob: To riff on Nicole's point, I'm almost in my sixth year and I didn't really start posting on LinkedIn or Twitter or doing podcasts till last year. So, almost five years in. And I try to be very clear that everything I'm saying now is because I've lived the experience for five years and I've applied a lot of hindsight and done a lot of thinking on it. And it may sound like I know what I'm doing, but I can tell you in the years of building the business, I had no idea what I was doing. No idea. So unqualified. Just figuring it as I go. I don't love, "fake it till you make it," but, I love the idea of just being relentless, having willingness to figure it out and be confident that you can figure it out. That would probably be a better saying.

So if people listen to any of my recent podcasts or this and think, "this guy knows what he's doing." Trust me, I did not know what I was doing. And I don't necessarily know what I'm doing moving forward from here.
I just know exactly how to contextualize and explain the past and build some processes to help me in the future.

"That's why I think the number one indicator of success in businesses is staying in the game"

Just understanding what happened and then applying that moving forward. Hindsight's beautiful. You can't change anything you did in the past. So you're better off just executing quickly and learning from it. At no point on the way to an 8-figure company did I feel like I knew what I was doing.

Actually, the more freeing thing I've come to know over the last year or so as I've met a lot of really successful people - as I got more vocal about my path, that kind of opened things up and I've met people that are billionaires and all different phases - and the one they can tell you that's true among them all is they're also just figuring it.

I loved that, because it was just freeing. They don't feel like they've made it? Who do I think I am? Who am I to think I've made it? I haven't made it, I have so far to go. I might as well just enjoy the ride.
The thing about entrepreneurship that's so difficult is every time you level up, you're a beginner again. You have to get comfortable feeling like you don't know what you're doing.
Imagine you're on a staircase. The staircase, like business, is infinite, there's never a top. You've never made it. And there's always someone ahead of you. There's always going to be someone working harder than you or doing something differently, at least in your head. I'm five years up the staircase, six years up the staircase, so I can talk about all those steps I've taken and sound like I knew what I was doing, but at the time, every step, I didn't know what I was doing.

And now that's why moving forward, I don't know exactly what I'm doing to take those next steps, but I'll figure it out. Cause I'll just keep walking. That's the important thing to realize. It's freeing. Once you realize that these people you look up to in business are human, they're just as flawed as I am. They're still figuring it out. They don't have super powers and they also feel insecure and anxiety and all these things. We're all in this together. We can figure it out.

"Another important habit for entrepreneurship is to practice thinking bigger"

One thing I've realized successful founders and entrepreneurs have in common is they just think a lot bigger than most people, and even bigger than I was thinking at the time. I remember sitting down with one person that I met, a good friend now, but when I met him for the first time I told him (I was all excited) I was like, "Oh, our business did $5 million."
Right away he asks, "Why not 20?" Immediate response, not a lot of emotion in the face, just an automatic response.
And I couldn't answer the question. I'm generally pretty off the cuff. I could talk and I can communicate well and I've thought things through, but that stumped me, and I reflected on it.

The only answer I could come up that was satisfying to me was that I just wasn't thinking big enough. There was actually no reason, no limiting factor. I just thought we did $2.5M the year before. Doubling seems reasonable. We've kind of doubled every year before that, but that was just a self limiting idea. What does 20 might look like?
So, that day I redid the budget and we ended up doing a million more than we forecasted, just because we pushed the limits a bit more.
I think it's really important for people to hear that. No one knows what they're doing. We're all figuring it out. There's always levels to this game. You might as well enjoy the ride.

Nicole: I've learned that this past year - I actually hired a mindset coach - and it's so interesting: she kind of takes a very similar approach. She was like, "Okay, think big. Let's draft it out. What do you want from your business and in your personal life? What is it?"

And I thought I was thinking the biggest I had in my life and she said, "Okay, times that by 10."

It was just so interesting how uncomfortable it felt to even go and think that way.
Ever since that lesson, it's kind of like a muscle that I'm learning to flex more.
Rob: Cool. Yeah, the other way you could ask that question is, "How do I accomplish my 10 year goal in six months?" You generally can't, but it'll force you to do it a year or two, instead of 10 years. Yeah. There's always ways to do these things much quicker and bigger, but yeah, it's been a learning thing for me too.

I think the exciting thing is that you can do it. You can think that big, it's permission-less.

Haruki: You talked about going up that staircase. And every time you get to a new step, you're always back to a beginner again.

"What is the process for finding your feet when you reach a new level as a business founder?"

Rob: Well, first we have the benefit of the experience from the steps before. It's also back to Nicole's point of building a network of people that are either the same size business as you, or a similar time in the journey, but also people that are a bit further up or further down the staircase as well.

You can lean on them for questions like, "When you were at this part of your career, how did you deal with these issues?" You can really start to crowdsource the solutions to a lot of your problems. You can read books about it too.
The best books to read for these sorts of things are biographies, because you can learn through their experiences.

Rob's Top Recommended Biographies for Entrepreneurs to Learn From

Steve Jobs by Walter Isaacson
The Story of Lululemon by founder Chip Wilson
That's an imperfect answer, but I'd say that's the only way to help front-load the learning curve, or soften the learning curve.

"Build a network of people that can help you, and have maybe been there before."

Recently, we did our financing round, and the main motivation for me was to bring in partners that had a lot more experience than I did. It was an investment in the business, but also me wanting to make an investment in me learning as an entrepreneur and surrounding myself with really smart people.

At that point, I had a lot of opportunity to attract, basically heroes of mine, to invest in the company. Now I get to ask them questions and it feels insane. The benefit of that is they're able to frame a lot of the things. If I'm having a big issue to me, they're like, this is just par from the course, this is fine.

For example, the rebrand (we got notice that we're getting a big legal thing). It's nothing I dealt with before. When I told a couple of our biggest investors, I was expecting them to act like the house is on fire. But no. They said, "Okay. No problem. We'll figure this out." It's like, what? You're not scared?? You've got millions of dollars at stake!
Then I guess I shouldn't be scared either. I'm getting paid to figure this out, and if you're not freaking out, I'm not freaking out.
So that's the real benefit of having people that are further up then you, because almost everything in business is not a death blow. There's some things that are, but most things are not. Your job's basically to recognize when they're not, don't overreact, because we're prone to overreacting and getting too anxious or stressed out or whatever, and try to figure it out.


"What is the darkest time, or the darkest memory you've had in business?"

If you think back, what did it feel like? And how'd you work through it?

Rob: It would honestly be most recently. The rebrand was probably the darkest time. The co-founder buyout was bad, but at the same time, it was really...if the business failed at that point, it was just me. It effected for the most part. I had one employee, and that would've sucked, but the stakes were much lower. During the rebrand [from Endur to Outway], we had a staff of 25 people. We had 11 investors with multimillions of dollars at stake.

The brand was doing really well, the business was doing really well, and in my mind this felt like a death blow.

Nicole: Sorry, was the rebrand because there was a legal issue or when you decided to rebrand, you were then faced with illegal issue with the new brand?

Rob: I can't talk too much about it, but yeah, basically the former. So there was an event and that's what led us on the decision to go through a rebranding process. And it was super scary.

But then the work over the next six months was just all consuming. So much legal. So many uphill battles I had to do. And it was basically six months. And the way I explain it now is: imagine doing everything physically possible to work on yourself. Mentally and physically. Eating well, and physically taking care of yourself with saunas and treatments...
I was doing all of those things, literally just to not fall apart. Not to feel good, just to not fall apart.
So it was just so incredibly...I was basically in fight or flight mode and it was...

Haruki: What was scary about it? What were you afraid of?

Rob: Here's the thing. Now that I'm talking about's hard to articulate because rationally, it was fine.

I had the support of the investors. We had a plan.It was just stressful. It was everything I had worked for. I was just, I was...I don't know. I felt such a fear of losing at all, even though that wasn't really a reality. We were going to figure it out. It was pretty apparent, very early on, that this wasn't a death blow, but I just wanted not only to get through it, but to continue to grow the business throughout it. I guess I just put way too much pressure on myself.

The thing is, I knew objectively, I knew everything was fine, but at the same time I was just incredibly stressed out. I just wanted it to go well, and then we launched the rebrand on May 1st. It was really well received. We had our best month of the year and we're continuing to grow.

But after that, basically from May until July - I'm only kind of out of it now - it was two months of the most severe burnout. Getting sick all the time. Very, very low lows. Not really knowing what's wrong. I hadn't felt like that ever. I don't think it was just from that six months. It was an accumulation of the 10 years of athletic career, plus the five years of the business, and this was just the monumental effort that was the last straw. It just took so much outta me and took a lot of the passion, excitement and just everything. It was probably more depressive than anything.

Even though everything objectively was great. The business was doing great. We accomplished this big thing. But I was flat-lined, really. I feel good now, but it took a long road to get back. I couldn't exercise as much anymore, even small efforts. I had to cut off caffeine. I had to make so many lifestyle changes just to not hit rock-bottom, basically. So, yeah, starting to get all that back, which is good, but that was really tough.
And that was a learning experience again. Back to the thing of how entrepreneurs are like athletes. We need to act like that and recognize that the majority of our year needs to be in a relatively base tempo.
If we're relating it to running or any kind of training, we need to stay in that kind of relatively easy zone for almost 98% of the time, because there's going to be some peak moments during the year, where you need to empty the tanks.

If you're going all-out like that for too long - I was there for six months straight - it leads to a huge decrease in performance. You're much better off thinking through your year and identifying where the peak moments for you are. For us, that's Black Friday and maybe to kick off the year there's a few other peak moments where it's all hands on deck and it's going to require a significant amount of mental effort.

I have a monthly lunch with a sport scientists and pick his brain about this stuff. How do athletes train? How do they cycle through these things? I just apply it to business and that's been the learning coming out of this burnout: I shouldn't have gone that deep into the trenches. It took way too long to recover it. It was damaging.

I need to do a lot of restorative exercise. I need to make sure I'm keeping up with my wellness routines. If something is stressful, is me dealing with this right now going to solve it? If not, I'm taking the day and I'm going to go exercise and change my state of mind and get out of it all. Just make sure I can alleviate these things.

But, that's the hard thing. You'd ask most people that are going through tough times mentally, and once they're out of it, objectively, it was okay, but you just can't get out of it.

Nicole: Yeah, I actually recently stumbled across the Midday Squares Podcast, and I actually love they're actually sharing stuff in real time, which I find really interesting. They talk about how messed up some things are, and they're just recounting it in real time. It's funny because I discovered that after posting on LinkedIn, so I feel like I've put something out into the universe and it's all coming back to me now.

Rob: Yeah, these things aren't uncommon. So, I think it's important to talk about them too. The same friend that was like "Why aren't you doing 20 million?" he says, I'm going to miss-quote him, I always miss-quote him, but he basically says that,
Entrepreneurs have an anxiety disorder that's harnessed for productivity.
So it's like, we're not alright, we're just using it to be really productive and functional. I think it's really hard to turn that off. And I think you meet more entrepreneurs, like Nicole, that we speak the same language. We could be fast friends and talk for hours, I'm sure, because we live in the same world and there's so few of us.

I talk to my partner, or my friends and they'll say, "Why aren't you more normal? Like, what's wrong?" I don't know, I'm just not, and I've had to reconcile that. That's just the case. I'm not going to be normal. I'm going to have a harder time enjoying some things than other people. I'm going to maybe be a little less happy in situations where I'm not achieving something, and that's just my chemistry. I'm working on it, but at the same time, I question whether if I got rid of those things, would I be where I am today? Probably not. So there's the sacrifice, right?

But, that's the benefit, again, of having the network of people that are weird and they are not okay or not normal. You get around them, and oh, we're normal in our own way. It's the same thing with athletes. Again, they're not normal either. It takes a pretty delusional mind to want to do what they do. It's's not easy.

Nicole: You guys are giving me a whole other level of respect for my co-founder. She's sitting next to me right now, so she can hear half of the conversation, but she is also an Olympian and a pro athlete, and building this business with me. So, wow. She's apparently quite delusional if she's doing all those things at once

Rob: Yeah. She's got a special love of pain.

Haruki: What about you, Nicole? Same question. What's been the lowest moment for you so far?

Nicole: Honestly, I don't think there's one single moment. I think for me, it's a blur of just trying to penetrate a very challenging space. Our company is Tall Size. We're very tall women. I'm six feet. My co-founder's six-four. We've struggled our whole lives trying to find clothing that just fits our bodies, just fits, let alone expressing ourselves through fashion and all of that. Hasn't never been an option for us, and there's a whole slew of other problems that tall women face.

The world that we're trying to enter, which is right now manifesting in the fashion space - we've got a much bigger vision for Tall Size, but for now it's the fashion world - and nothing is made for tall humans. So, when it comes to manufacturing and producing items and clothing, the costs are so much higher because they've got to develop new patterns. Nothing is just off the shelf.

It's also a niche market, so going out and finding these women and figuring out where they are...and then tall is one thing, but then you also have the whole slew of other different body types as well. So, it's just sometimes been demotivating or scary, because no one seems to have cracked this yet. No one seems to have figured this out. On good days, I think, "We're the ones to do it!" But, then on the bad days, it's like, "Is this figure-outable?" So, that is the challenging part right now.

And Rob, having the grit to just stay in it and know we'll figure it out. I would say that's the scariest, or the most challenging thing, in my head anyway.

Haruki: Is that the way forward Rob, or something else? In moments of doubt, just having pure grit, single mindedness, and just pushing through?

Rob: I love this quote by Henry Ford,
"Whether you think you can or think you can't, you're right."

"[Business and entrepreneurship] is all mindset, you might as well just keep going."

Who cares? You'll be much happier if you just try. It's super possible. Everyone I've met that's truly made it, or is making it, or whatever, is no smarter than anyone else out there.
They think a lot bigger and they don't give up, and they get smart because they acquire the wisdom and the experiences as they try. So they become smart.
I can tell you they didn't come out of an MBA for the most part, they generally probably did poorly in school, I know I did. I'd say you don't have the answers, you're a year in Nicole. That's the other good thing though, is you don't know what dark times are coming. A lot of people ask, "If you could go back, what would you change?"
I would say if I knew what I knew now back then, I probably wouldn't start.
Because it's just so hard and it's so scary, but at the same time, it's so rewarding. So there's a benefit of being kind of doe-eyed. It's exciting, and then you can take a unique approach to things. You can truly innovate. That's what the benefit of just starting and being a beginner and just figuring out as you go.
All the best businesses were built by people that were unsatisfied with the way things were done. So why would you over-dilute yourself with learning how things are done? Just go do it, just go figure it out.
Just use some of these strategies, these would be worthwhile conversations to listen to and learn how do I mitigate some of the downsides of burnout or how can community help me, or whatever. Those are all things that should be applied, but also just carve your own way and go for it.

Haruki: Great advice. And I a great place to end as we're coming up on time here. Another good way to seal something off is with a plug, so if you guys want to take a second, tell people where they can find you and what they might find there.

Nicole: You can find me on LinkedIn, I think is the best place if you want to follow my own personal journey, but if you are listening to this and you are tall or, you know tall women in your life, head over to

Rob: Same thing, I'm on active on LinkedIn and Twitter. Twitter is what I use the most and then distill that down on LinkedIn. Our business is at, and if anyone wants some awesome looking, very comfortable performance socks, we've got you covered.

This was super fun, really appreciate the conversation. It's probably worth a round 2 at some point, because we can probably talk for hours on it, but happy to continue to share as things evolve and thanks for having me on. Thanks for the invite. Super fun.

Haruki: Of course. It was great to have you both. I want to thank you both for taking the time and giving me a great conversation. It was good to have you, thank you.

Okay guys, have a good day. Talk to you soon.

Rob: Take care. Bye bye now.

Nicole: Bye!