The Emotional Rollercoaster of Startup Leadership and Balance with Robbie Bent - Mark MacLeod

June 5, 2024 - Marina

The Emotional Rollercoaster of Startup Leadership and Balance with Robbie Bent

Don’t miss out on my conversation with Robbie Bent, the visionary co-founder and CEO of Othership, a transformative space that combines sauna, ice baths, breathwork, sound, and community to redefine wellness in urban settings.

Robbie Bent’s story is not your average entrepreneurial tale. With a background marked by personal challenges, Bent’s mission with Othership is deeply personal.


Delve Into the Transcripts for Crucial Insights from this Episode

Mark MacLeod:
In this episode, I have the great pleasure of speaking with Robbie Bent, co-founder and CEO of Othership. This is not your typical startup story—Robbie and his co-founders are growing a physical experience business using many startup tactics, and they are on a serious growth trajectory. Othership is a space for transformation, a unique combination of sauna, ice baths, breath work, sound and community.

Robbie’s dream is to solve loneliness by giving people in major cities a healthy place to meet and to heal. This is a deeply personal journey for him.

He has many hard-earned lessons to share with us. I hope you enjoy our discussion.

Robbie, it’s a true pleasure to have you on The Startup CEO Show. Thank you for joining me.

Robbie Bent:
Thanks, Mark. I’m excited.

Mark MacLeod:
Othership is not technically the standard plain vanilla startup and that’s actually really why I wanted to have you on the show, because I think you have unique lessons to share with everyone and I always find the origin story of a company to be fascinating but I think that’s particularly true in your case because it’s really a personal journey and mission. So I’d love to start there and love for you to just tell folks about this journey you went on and how you arrived at Othership.

Robbie Bent:
Yeah, absolutely. I mean, I think it’s really hard to build something in a short period of time when it starts as a business that has to be successful. And so I’ve always found that playing at passions and curiosities and side projects is like the best way to get started.

Real things generally happen through tinkering… Good ideas when they’re obvious, there’s a lot of competition and somebody is going to do it better than you. And magic really happens from tinkering when a non-obvious idea comes.

So we were just starting out with an ice bath in a backyard on a residential street in Toronto, and that ice bath was free. And so if you knew you would open the gate, come in, and there was an ice bath and a fire every night. And my friends and I did this because we were looking for something healthy to do in the evenings.

I personally struggled with substance abuse throughout my twenties, and so I wanted to be away from environments where there were bars and alcohol, restaurants, stuff like that. And so every time I would go to a new city, I would go to a bathhouse. I started getting obsessed with hot and cold as a way to socialize. And most of these places would know Russian on the outskirts of town. A little bit dingy, but awesome and like amazing experiences.

And so when I moved back to Toronto, four of my best friends, one being my wife, we just made this ice bath with an idea of, could we create a community of healthy people in Toronto with something to do at night in the summer that wasn’t alcohol-related. And so it just started like that. It was a WhatsApp group. You could drop in and every night we’d go out and invite restaurant owners down the street, gym owners, just friends, and would just do this ice bath. And it was free of charge. It was just something fun.

As the winter came along, obviously it was a bit cold outside to just do an ice bath. It was literally a block of ice. So we looked at my garage and I had this standalone three-car garage and it wasn’t being used for anything. It was like a woodworking shop. And it’s like, I wonder if we can do something with this. So we built a non-permitted sauna and an ice bath and made a little tea room. And we spent about 80 grand on it and did it ourselves, just again to be like a community space. And in that space, things really started to go crazy. So within a couple of months, we had a thousand customers.

At first it was free, then it became donation, then we started charging. And we really learned a secret in that space (which) was that, yeah, people are coming for the health benefits, which you hear about on Andrew Huberman and Joe Rogan and Tim Ferriss, and you see people doing ice baths on Instagram.

But we found there was something deeper. There was actually an ability to connect to a meditative state and process emotions. And so we started designing classes. And they were just for fun at first. So it’d be Valentine’s Day and we’d have three couples and we’d say, oh, let’s do a couple’s ice bath where there’s an eye gaze and a hug after.

And let’s all go in the sauna and share our first date story. Everyone’s crying. By the end, it was like, wow, this is actually a really unique environment to run therapy-like classes, because nobody’s on their phone. There’s a state shift happening that reduces the inner voice, the ego, and makes you more likely to connect with your emotions, and it creates an incredible social experience with a captive audience.

So we sort of saw just through testing that I think this is an interesting format for a new style of group therapy, for lack of a better term, kind of a group therapy mixed with performance. So it’s fun, it’s inspiring. And so we started practicing all kinds of different modalities, instruments, breath work, meditation techniques, movement. And we were about midway through COVID, and people kept messaging me.

They started coming on their own as their only place where there would be an app. It was self-serve. And people were messaging me, hey, this changed my life. I met my romantic partner, or I stopped drinking, or this was the only social experience in the city. Just these crazy experiences. So it was New Year’s, and I think I got 15 messages of like, hey, you had a real big impact on me this year. And I’d been working in tech for 15 years, and I don’t think I’d ever got a message that anyone cared about what I was doing, ever.

So, okay, this is fucking cool. There’s enough evidence here that I think that people want emotional classes in the mainstream at a large scale. And I think we think that there could be a new way to socialize. And so we signed a lease, which is fucking intense.

Mark MacLeod:
Scary! (laughs)

Robbie Bent:
…During COVID we self-funded the first one. It was $2 million billed. And we’re like, we think people are going to come, but are they?

Mark MacLeod:
Are you, like, mortgaging yourself? What’s the reality?

Robbie Bent:
Yeah, so we had five partners. We signed… You’re able to get a small business loan, so we personally guaranteed the loan, and then we self-funded a couple of hundred thousand dollars each. And so, yeah, it was meaningful amount of money. But also, we’re like, this is a space we would use, that we would love, and we think it’s going to work. And so we took a huge leap.

And I remember the first piece of PR out was a blog to your article. And in the comments, some woman just said before opening, who are these bozos? 40 people in a group sauna. Disgusting. Will never happen. I remember seeing that and being like, oh, my gosh, have we committed? It’s a ten-year lease. There’s a lot of money on the line. It was very nerve-wracking, especially because there was no, when we launched, and still to this day, there is no sauna and ice bath class in the world. It was just a crazy idea.

And so we opened just as the COVID restrictions came off and it was just very clear that people wanted a space to process emotions that wasn’t therapy, where you didn’t have to say, like, I’m depressed, I’m struggling. It was kind of an inspiring space. They wanted a space to do that in community, and they wanted a space to hang out and socialize at night that wasn’t alcohol-driven.

Mark MacLeod:
That’s amazing. Wow. There’s so much to discuss there, and there would be many episodes. But first of all, I can say, as a former VC, just your insight about kind of non-obvious opportunities, I guess why they call it venture. My observation, looking back, is the biggest opportunities were based on an insight that was obvious, but only after the fact, like Uber.

It is obvious now, with the benefit of hindsight, to know that it’s better to just press an app and have a car show up. And for the driver, we can set aside whether they make a fair living, the politics, but just as an experience to know exactly where your next fair is and not fumble for change and know that it’s like a human with a rating and all that stuff.

But if someone had come into my office when I was a VC, I’m like, hey, I want to disrupt the taxi market, I’m like, dude, that’s a solved problem. Taxi medallions, unions, like, forget it, right? And so it’s tough. I genuinely think that’s why they call it venture.

I hadn’t, and I will say on the experience itself. So I’ve had a couple of exposures. One, you invited me down to the flagship place on Adelaide, and that building has a lot of positive vibes for me because it was one of my last deals I worked on as a banker was the sale of TWG to Deloitte, and they were a pretty big tenant in that building. But it’s such a beautiful experience. The leaseholds are crazy and everything’s thought out.

I’m in the final stages of completing my 300-hour yoga teacher training right now, and if I wanted to start a yoga studio, I know what it is, I’ll put my own touch on it. But if I want to hire a yoga teacher, they know what they’re coming for. But you’ve designed this actually completely bespoke, multimodal experience, and so I think it’s really special.

And then that Leela journey event that I came to, which I actually think was my first exposure, I didn’t feel like an outsider because it was a welcoming environment, but it was so clear that there was a tight community. You could just see it. And even just the way you describedit, you weren’t even trying to build a business per se at the beginning, but you were building community from day one, which is such a vital asset. So, yeah, kudos. It’s really special.

I wasn’t planning to go here, but so many people in general, and certainly so many hard-charging founders, struggle with substance abuse. And I wonder if you’d be willing to talk about what life is like on the other side.

Robbie Bent:
Yes, I have ADHD, and so I love stimulation. I can work really hard. I can watch 10 hours of TV. I can read an entire book in one go. But I love extreme sports, I love coffee, I smoked cigarettes for a long time, and so stimulation for me, like, I just love partying and being around people, and I didn’t really have… You know, at university I just kind of wanted to be rich, and I didn’t care how.

And that was what was important to me (which) is a bit insecure, to be honest, but it’s okay. I’m going to do whatever I can to make a lot of money. And I was in some tech businesses that failed, totally hit rock bottom. And every night I’d go out for a glass of wine, I’d have four, and then I’d start taking cocaine and disappear for two days.

And basically two days out of every week were shot. And it was definitely… To be a performer in that state is impossible. And that’s how I would deal with stress. And as my business failed, it was running for four years, and I knew for the last two years it was going to fail. And I just was so afraid of that feeling. Like, we’d raised $20 million, I had 100 employees at one point, and it just wasn’t working. And I was like, what’s going to happen? This is my life savings. It’s my salary.

What are my skills? And to deal with that, I would just obliterate myself on the weekends. And I ended up getting into meditation. Ten-day Vipassana retreats, psychedelic medicines…

Mark MacLeod:
By the way, again, an extreme example, like, ten days is a big deal, right?

Robbie Bent:
Exactly.

Mark MacLeod:
Seven days. And midway through, they’re like, I am going insane.

Robbie Bent:
Yeah. With my therapist, they’re like, hey, for you, it’s not like go and live in a cave for seven days in darkness or do a ten-day meditation retreat. It’s like, can you just enjoy going for a walk outside and be here with the ‘normal’? But those things did help me realize like, hey, I shouldn’t ever drink again.

I met a partner who was as committed to health as I was, and my wife now, and co-founder and mother of my son, and so she was a big support. But having something to do to deal with those needs for stimulation was, like, crucial. And having something to do that was social, where I could be around other people and still have fun in a specific environment was key.

And so for me, that was the bathhouse. That’s what we’re doing at Othership. So if I’m going to go out, I’m going to Othership. And so I solved my own need for socialization with something healthy and the ice bath doing something similar in the brain. It’s tripling dopamine, norepinephrine. The same thing happens when you’re using coffee or cocaine or cigarettes.

And so it’s a way for me to get that stimulation, but it also does something unique where it’s boosting your baseline levels of dopamine. So it’s not like these other substances where you’re getting these quick hits and then depleting.

So there’s quite a big correlation between founders, ADHD, drug use as well as stimulants, coffee, and so ice baths for that demographic, I’ve seen work extremely successfully. So on the other side, since I stopped using substances, I joined the Ethereum Foundation. Was quite successful there almost by chance.

You know, I moved out to San Francisco because I followed smart people instead of following money. Did well, but was just lucky. And then started this as a side project in a completely different way. Instead of targeting money, it was, oh, this is just something I enjoy and it’s an MVP and it’s for fun.

And we’ll keep adding to it and adding to it and adding to it, and the idea evolves to what it is now, but that’s only possible in the last four years. I’ve taken maybe two vacations, I work on the weekends, I work almost every day, and I can do that because I wake up sober and fresh and I feel good. The other thing, huge difference of being on the other side of that as an entrepreneur is even now, some days are just terrible. There’s a Mark Andreessen quote, it’s like a startup is terror or euphoria.

Mark MacLeod:
Yeah, that’s right.

Robbie Bent:
And let’s say it’s 80% euphoria, 20% terror, if you’re drinking, it’s going to be 70% terror, 30% euphoria. You just can’t handle the stress when your state isn’t optimal. So I think the biggest difference for me is just one integrity. Like when I was drinking and using cocaine, it would lead to all kinds of bad behavior. And now I’m actually somebody that I feel like I’m a good dad. I’m an amazing husband. I treat my relationship as my most important thing in the world. And it’s just like a night and day difference in my life.

Mark MacLeod:
Amazing. Thank you for sharing that. This brings up boundaries for me , which is a thing I wanted to ask you about. You work during the day. Your business prime time is actually in the evening. It’s also the weekends. You’re very often there. You do have a wife, you do have a son.

As you and I have talked about in the past, it would be tragically ironic to be killing yourself in the process of trying to make everyone else healthy, so boundaries are important. How do you actually navigate all of that? Okay, now, are there rigid separations? Are you able to create different contexts and switch off, or is everything just sort of blended?

Robbie Bent:
It’s really hard. And so I think I’ve gotten better, but I’m still struggling. And, like, earlier this year, I’d been going for three years straight. I was running finance, construction operations, marketing as a single person.

And so since then, we hired as a CEO. Can you hire, firstly, to take things off your plate? And so we hired (the) former director of construction from SoulCycle. We’ve hired a professional COO, we’ve hired a controller, so my bandwidth has increased… If you’re just stuck in the details all day, you can never get anywhere and you’re just doing the same thing over and over.

So that was a major, we should have hired even sooner, probably. So that was a major change. But there were points, you know, in March where, okay, we’re struggling with Yorkville, which is our second space to launch. New York is a complete disaster. We’re going to lose these leases. Oh, my god. We’ve signed a lease and we don’t even think we can build what we need. From a code perspective, I might have just committed like a million-dollar security deposit and lost it.

And I’m kind of crying each day and I’m getting complaints about the experience and kind of just so… I was also just drinking coffee in the morning and then not eating until 05:00 PM. And I’m so upset that I’m just like, honestly, fuck the customers, fuck this, even though I love it so much. And so what I would do then is go to just one is if you’re in that state, it’s just not… You can’t be like a real human being.

And so I’d come home from work and I work from home, but I would be just thinking, my wife’s like, where are you? And I’m not even there. So hiring really helped some other things that… But also, look, when you’re starting, you might not even have the money to do that. So it’s just kind of hard.

Mark MacLeod:
You probably don’t have the money for…

Robbie Bent:
So I look at it as like, what am I willing to sacrifice for how long? And it’s worth it to me, to be honest. If I look back on it, yeah, absolutely. Okay, that’s what it’s going to take to build something great, and create something in Canada, and go to the US. That is what it takes. You have to have fanaticism about every little detail, and you just have to care at that level. So it was worth it.

Now the role has shifted from like, okay, I’m not an individual contributor anymore, and it’s actually detrimental to the company for me to do that. And so now my role is mostly emotional. So it’s like raising money, vision, ensuring all the employees are the right people, and it doesn’t take, like, I’m losing my temper on calls with people and they’re afraid of me, which, candidly, yeah, I’m just trying to be as transparent as possible, so people know. But, yeah, I would lose my temper and people are like, whoa, this guy’s fucking intense. And I would like, yeah, sometimes then regret it after.

So the boundaries I have now, though, I take one week per year, which I’d always done. It’s not enough, but it’s a good starting point to have my phone off. And so whether that is a vipassana retreat or just in nature or a psychedelic medicine retreat, whatever it is, it’s one week with no phone.

I’m trying to do little bite-size things twice a year where it’s like a weekend, again with no phone, healthy eating… Now it stopped because we just opened the new space, but I was taking one morning a week to do a massage at Myodetox and that’ll float, and to just start my day, again, no phone, no caffeine to kind of layer in.

And then I’ve started doing, for the past year, therapy bi-weekly, a two-hour session of IFS parts work, which is just like, feeling emotions in the body and kind of talking through the way we are, like, “hey, there’s a competitor launching in New York, I’m afraid”. What does that feel like? Not like, just try to ignore it and be pissed, but like, okay, I’m angry. Why am I angry? Because I’m afraid they might do it better than us.

Okay, what is that? You know, okay, let’s feel that feeling. It’s okay to be afraid. And so before, I used to just try to, the hard feelings, like, push them away. And so what I’ve learned this year is to just feel them deeply, and they usually subside a bit. And so that therapy I’ve been doing has been extremely helpful. And then on the dad’s side, I was also feeling guilty of, like, I’m not really helping. I’m tired in the morning. I don’t want to get up early.

And there was a discussion with my therapist that recommended to just have a discussion with my wife, and was like, hey, what do you need for support? And she’s like, I need you to get up four mornings a week. And I was like, okay, well, I don’t want to. And so I ended up hiring a nanny, a morning nanny.

At first, we were like, oh, we want to spend more time with our son. But it turned out to be more worthwhile to have someone come 06:00 AM To 09:00 AM four days a week so we could sleep.

Mark MacLeod:
Yeah, especially because you’re kind of long in the evenings, right?

Robbie Bent:
Exactly. So getting sleep was super important, and so something I thought before was just to be resourced. So I have two equity advisors for business advice. I have my therapist. I have a health coach. So another thing, like, I wasn’t eating in the morning, so I did all my blood work with this health coach, and now it’s mandatory that I have a shake, even if I’m all riled up, ready to go with banana, avocado, protein powder, a bunch of stuff. So at least I’m getting my nutrients first thing.

And I thought, like, oh, I’m intermittent fasting. Like, who cares? I won’t eat all day. Like, there’s no nutrients there, and you don’t have the energy. And then I would be way too stimulated. So morning shake, nanny for support therapy time off intermittently. We’re going to take our first vacation in a couple of years in Costa Rica in February, and I just feel like now being present and emotionally aware is sort of what the CEO role is.

And so I’ve been more aggressive about not being, as in the day-to-day for specific roles.

Mark MacLeod:
I am so glad you said that. I feel like I’m on a crusade with my CEOs, because especially in the tech world, right, there’s just this default expectation that it’s just back to back to back meeting, meeting, meeting. I’ll pound emails at night, I’ll do Slack whenever. But if you actually think about if you’re at the right altitude, if you’re working on the business versus in the business, it’s actually a small number of big decisions that move the needle, but right, higher, like, to your point of really articulating vision, especially as the team grows, communicating that over and over and over again, and you actually want the freshest, crispest mind to make those decisions.

And of course, our brains are just not even designed. You talk about dopamine, we’re addicted to dopamine in the wrong way. I’m a guy who has a deep practice, and I still find myself in the middle of writing something. I’m like, oh, let me go see who’s liked my LinkedIn post.

It’s like the worst. And this is me with some level of awareness. So I really love that you said that and the importance of presence. And I also think that what Othership does is actually really, well, important for society at large, but certainly important for people who are interested in performance.

After I came to the flagship location, because I live in the middle of nowhere, I put a sauna, a hot tub, and a cold plunge in and would hit it regularly and noticed that… First of all, I do CrossFit. The first rule of CrossFit is to talk about CrossFit. It’s like the opposite of Fight Club. So I’ve done that. Check the box. So it really helped me with inflammation. But I think more fundamentally, I sleep better on the nights where I do it. Like just more deep sleep, instantly asleep. I don’t know, just lots of benefits.

You’ve just cited a bunch of ways in which you are investing in yourself. And I often say that CEOs are like professional athletes, right? You have the same kind of expectations on your shoulders, right? Like, LeBron James has a team around him to make him peak LeBron. He’s got, obviously, a physiotherapist. He’s probably got sports psychology, coaches, you name it. Whatever the peak nutrition, whatever he needs, he’s got it. And then he’s also deeply investing in sleep. I remember hearing about how much sleep he was trying to get during the playoffs, and so I feel like you’ve got kind of a similar level of awareness going on here, which is great.

Robbie Bent:
I think anyone can over a two-year period grind it out, 100%. But we’re building this. This wasn’t really a profit endeavor to begin with. Now it is. Obviously, we want to make money, but I would never franchise this. I want to build it out personally in over ten years. I want to build 100 locations and I want each one to feel like a five-star restaurant or like a four-season where it’s that amazing. And to have that motivation.

I was reading something like within five years, 90% of CEOs will consider quitting. And around the four to five year period, it’s like, I hate this, I hate the customers, I hate my team, I hate everything about it. And so it’s just if you want to do the thing for one, if you’re not doing it for ten years, it’s hard to get advantage because advantage comes from scale over time.

And so yeah, this is my life calling. I’m going to do it. But if you want to do something for more than two years, you’ll just break. And I’m pretty hardcore and always have been. And I’m almost broken like four times even with some of the practices.

Mark MacLeod:
My yoga teacher, Kia Miller, her husband is a guy named Tommy Rosen and he’s written this book called Recovery 2.0 and he’s very public about pretty serious substance addiction. And he’s decades away from that. And he’s devoted his life to helping others with that. And yet he even talks about how every day is a struggle. Do you find the same?

Robbie Bent:
No, because I’ve replaced… Again, I guess addiction comes in varying degrees. And I’ve just replaced unhealthy addictions with healthier addictions. And so work and coffee have taken the place of cocaine. And it’s also like just ruining my life. And so there’s never a desire of like, “oh, it’s 08:00 PM, I should go out and disappear for two days”. And so now I have guardrails.

I have like a wife. I used to also do that to chase girls and to try to meet people. And now I have a wife that I care about more than anything. And so a lot of the desires around why I was doing that have shifted, but the behaviors are there. I just know how to deal with my addictions. And so now it might be a fantasy novel. If I’m really cranking, I’ll read like Dune or some kind of Sci-Fi and just read that for 6 hours as my rush.

Mark MacLeod:
(laughs) It’s a pretty big book.

Robbie Bent:
Yeah. So it’s finding out what works for you because I also believe you have to have fun. And so for me, I can have fun with psychedelic medicines, and they’re not as risky. I can have fun with cold plunges and bathhouses. I don’t feel like it’s a struggle like it was, for sure.

Mark MacLeod:
Right. That’s amazing.

You know, you’ve referenced your wife before, and I want to go there, right. Most businesses fail. Certainly, most businesses that try to go rapidly, most co-founder relationships fail. There’s someone typically the CEO has—I’m totally stereotyping here—but the CEO has more context, more motivation, often more ownership.

It has access to more experts, especially those that have raised venture capital, because meet this CEO, you’re absorbing more than, say, a co-founder in a different role. And so very often, co-founders don’t go all the way. And now there are marriages within the… First of all, there’s a number of co-founders. Like, there’s like six of you, and there are marriages within this group. So how do you navigate all of that? What were the kind of discussions up front? Did you go into it with an awareness of the risks? I’d love to learn more about that.

Robbie Bent:
Yeah. So my partner had been in restaurant groups and had had trouble his entire career with co-founder dynamics. I’ve been in five companies now as a co-founder, early stage person. And so a lot of awareness of the importance of coaching and the importance of this upfront.

And so right from the beginning, I was the CEO, and there’s no check on my decision. So if I say it’s New York, it’s New York, if I say it’s Miami, if I say we’re going this size, there’s one person with authority, and I don’t think you can build something where there’s co-authority. So the first thing with a co-founder decision is one person is the CEO.

And that’s very clear right from the beginning. Second, we had coaching right from the beginning. And so especially starting when you don’t need it, it’s more important because you need to build trust with your coach and every person on the team has to have that trust.

So when conflict arises, which of course it does, because the co-founder who manages finance for a single store is not going to be the CFO. The co-founder who manages construction for the first two is not going to be the person who leads to 100. And so almost every single role will be replaced except the CEO because the job changes. And so we had that discussion up front.

It was very clear, and people were okay with that. And we started coaching early, so from inception, everyone met with the same coach. We’d meet with her weekly, and when friction comes up, she would facilitate arguments, moderate them like you’d have an arbitrator. And so we’ve had discussions around equity fairness over time. We’ve had to reshuffle splits, which I think also was really good in that we were friends.

And so there’s been resentment at times when one person is pulling more weight than another, when some people do try to do jobs where they didn’t have the experience for. So all of that stuff we’ve had to go through, and we’re in a really good place now, but it was coaching, willingness to shift equity, clear line of decision making. And it sounds complicated, but the good thing about it is, if you can manage the dynamics, it’s actually a superpower, because you have five co-founder energy, and that energy is like, if any one of us is in the space and there’s something amiss, boom, immediately escalated. Like, we need to fix this.

Every employee that deals with the co-founder sees that level of passion. So you have five times the passion. So we’re actually able to build a community that we want, especially for a brick-and-mortar product. So we can just move five times faster. You know, in these four years, not only do we have multiple spaces and are expanding to the US, we have an app as well. So, some of the co-founders work just on the app and launched it.

So overall, I think if you can make it work, and if you can make it work with friends, there’s, like, no better journey of meaning to have with a… There’s nothing like in a friendship (where) you can often avoid conflict. In a business, you can’t. And there’s nothing like growing with people around shared meaning. So to me, it’s just the most wonderful gift. And I think, honestly, every day, thank god that I’m not alone.

Mark MacLeod:
Yeah, I think it’s really hard to do it alone, that’s for sure. My wife and I started this year is a marriage meeting. So every Sunday we meet, kind of make a ritual out of it, and the same agenda every week. What are we grateful for? What are the things that we noticed in each other in the past week? What chores? Divide and conquer, what needs to be done? Are there any issues? If so, let’s surface them. And then plans for good times. Let’s not just let life happen, but let’s actually plan.

The thing I love about it is, well, I feel like you said you got the coach before you needed it. We have this mechanic for investing in our relationship before. Small issues left unaddressed are like cancer cells.

They just metastasize. They get bigger, and small things become big things. So it gives me a lot of confidence in the relationship because I know we have this forum, and then often if one of us is upset, well, we know we’re going to meet that Sunday. And often by the time Sunday comes around, it’s not that big a deal. And if it is, we bring it up. And so I love that you guys have built-in, I guess, like a similar kind of set of practices. It’s a machine. You’ve got to keep it oiled and finely tuned.

There’s lots of moving parts. It’s like a high-performance sports car, right? You’ve got to maintain it.

Back to kind of putting on my VC hat. I look back in year 24 in the startup world, and when I look back, the single biggest factor was timing. You get everything else right. Rockstar team, amazing product, but if you don’t get the timing right, it’s really not going to work.

It seems to me from the outside looking in that you’ve kind of nailed timing. What are your thoughts on that?

Robbie Bent:
Yeah, I don’t think we could be any more lucky. And so there was a whole bunch of things, like I had mentioned, like this wasn’t a business we were doing hot and cold, not because of the health benefits, but because of the community feeling and because we wanted a space to socialize.

And so at the same (time), bathhouses have existed in every single culture except North America. So there’s a market that should have this because it’s everywhere else since the beginning of human evolution, basically, and there’s none. Then you top one, you know, there’s a huge movement to sober living, which I’ve seen and lived, so people looking for healthier experiences, then there’s health benefits, which every day there’s a new report. We don’t even market any of the health stuff because it’s just happening for us.

Then there’s a problem with loneliness in urban areas, which isn’t quite well known yet, but it’s like the surgeon general’s number one thing is more dangerous than 15 cigarettes a day is loneliness. And that’s due to increased use of cell phones, isolation from using things like Uber/Uber Eats. Everything is instant, and as a result, there’s less human connection.

Now even more people meet online than all other forms combined. So there’s this whole thing around loneliness and people wanting to connect. Then there’s like, health and longevity that’s exploding. And then finally there’s people that are looking for more meaning. So spirituality, yoga, meditation, stuff like that, psychedelic medicines.

So I think we’re really hitting a place where life is default, unhealthy. And if you live in a city, you’re default, unwell. You’re at a desk, you’re not outside enough, you’re probably not eating properly, you’re on your phone all day. And so I think all these trends are kind of colliding into something perfect for us in a market where there is no competition yet.

So timing is excellent and we’re the first mover. Now, brick-and-mortar is challenging with like a VC hat on because you hit product market fit, there’s no real, like, the barriers of entry are, hey, it’s expensive to build, it requires, it’s quite complicated, takes time. And then to scale many, it takes like an enormous amount of capital.

And operationally it’s extremely difficult because you’re relying, it takes me 50 to 100 people to run one of these spaces. So, it’s quite hard to scale. So it does take time. And then you have to sign the lease, you have to guarantee the debt. So it’s not like everyone can just pop these up, but it will take us ten years to build these in every city. And so of course there’s going to be competitors. There already are. And so you see the idea and you can copy it.

And if you’re in a different neighborhood that’s closer to where someone lives, it’s out there. Whereas if you build Shopify or Facebook, these have network effects that prevent competition and that just doesn’t really exist here. So in one way, I think the timing is perfect, in another, I think we really have to think about how fast do we go while also maintaining a five-star customer experience.

Mark MacLeod:
As you’re planning kind of locations, facilities, are you planning around people returning to work, like moving into offices, or are you planning around residential kind of high-density areas?

Robbie Bent:
Mostly high-density areas. And so when we look, the good thing is now is these just don’t exist. And so as long as you’re in a high density neighborhood, you’ll probably be the only one. And even like in New York, we’ll get the numbers, we’ll look at where the best Equinox is, where the best Soho house is, where the best Barry’s is, and kind of look at the numbers of high-end consumer fitness brands.

But we would not go into an area for a discount. That was a tier-two building. I think one of the only ways to stay ahead with these types of businesses is to be the premier brand, and brand is everything. So every email, every piece of language, how the front desk greets you at the front, how clean it is, how often the maintenance is done, how differentiated can you be? The minute you go into a tier-two building, even a tier-two neighborhood, it really impacts the brand.

And so, generally, with these things, even though there’s a lot of competition, there’s only one SoulCycle, there’s only one Barry’s, there’s only one Equinox. And it’s the brands that focused, maintained their brand promise. So that’s kind of how I think about it, is like density plus neighborhood brand.

Mark MacLeod:
Yeah. It’s not a coincidence that those are your neighbors in Yorkville, though.

Robbie Bent:
Yeah, exactly.

Mark MacLeod:
Equinox is a block away. Barry’s is, like, literally around the corner. I used to go get shakes there all the time. Yeah, you’re in the right place. The three keys of retail, right? Location, location, location.

All right, you might cringe at this question. What tales, good or otherwise, do you draw from WeWork?

Robbie Bent:
So the first one is, look, if you sign one bad lease for your first one, you’re bankrupt. If you sign one bad lease in your first five, you’re extremely impacted. If you sign multiple bad leases in your first ten, you’re bankrupt. And at the end of the day, it’s a unit economics business. These aren’t software businesses. They have specific margins that require specific throughput. And so if you expand to leases that are not profitable, you will not be profitable.

And so it was an extremely unique situation where someone was able to raise a ton of money selling a vision of a tech company that wasn’t with, you know, fast forward today, and you have a whole bunch of… I’m talking, like, I’m worried about one lease underperforming in my first ten, and they’re like, 75% of their leases are underperforming. So in bankruptcy, actually, WeWork would probably be a fantastic takeover. You could get rid of the bad leases, and the brand is probably still intact.

But I think the biggest tale there is just be extreme. Like, there’s this thing Jeff Bezos says is “Go fast when the decisions are reversible”. And the only decision in brick-and-mortar that is not reversible is your leases. And so you have a lot of companies, you have a grocery store where there’s a retail division, and they get paid on how many leases they sign. For us, I will walk every single space. I will go in the neighborhood. I will live there for a week. I will talk to all the tenants. I will ensure that ends with me only signing the leases.

And again, if you have to do for us to be really successful, 20/30, there’s no better use of time than ensuring those are the right spaces.

Mark MacLeod:
So you mentioned you came from the tech world. You just talked about lessons from Jeff Bezos. To what extent are you infusing this company with kind of startup practices, startup ethos, even though it’s actually a brick-and-mortar business?

Robbie Bent:
As much as possible. I mean, startups generally are interesting because they’re trying to make the most work with less, and they also have access to the newest tools. So our entire culture is async. We’re using Loom for stand-up meetings and for reporting. We’re using Typeform and VideoAsk for our interviews. We use a whole bunch of integrations with Mariana tech. We’re quite good with paid ads and customer demographic sourcing.

We do a Lean customer interview method from Lean Startup to talk to customers. We use the very disappointed survey from Superhuman. So we’ve taken everything from creating amazing customers, from automating our processes that I used. Even our chat is in Discord because it’s a company chat, but a community chat as well, which is like super random.

So a lot of time I’ve spent working remote in tech. So we have a lot of remote best practices, and then infusing that with like, okay, well, how do we also have ten-star hospitality? So one really interesting exercise we like to do is the Brian Chesky, what is the ten-star experience where you write down over 3 hours, what would this look like if you had no budget or constraints? And we sort of use that to help design our processes.

So a lot comes mostly not really on the product side, but more on the marketing and communication side from the tech world, because, you know, an e-commerce, Silicon Valley style companies that are doing consumer, they’re just way ahead. However, it is a hospitality experience at the end of the day.

And so we’ve actually driven more from Danny Meyer. We’ve created ten magic moments, and so we want you to have these ten moments every time you step into the studio. And that’s sort of proprietary to us. The IP of like, what are the ten moments that if these happen, you will guarantee to come back? And that is more from the hospitality world.

So I think there’s a lot of opportunity when you’re going into. There hasn’t been as much innovation as brick-and-mortar. So when you’re going into a new space and trying to take some of these management philosophies there’s a lot of opportunity and there’s honestly less competition.

Mark MacLeod:
Danny’s book, “Setting the Table”, is one I read many, many years ago, and found it to be pretty inspiring.

As we start to wind down, Robbie, just maybe two final questions for you. One, I want to go back to community. You weren’t building a business then, but you’ve built a really valuable asset. And I think lots of companies realize today, well, I can’t rely on social. The algorithm changes, I’m renting audience. I want to build my own audience. A lot of people are thinking about community. Can you reverse engineer? I know this is a specific use case. It’s a physical product, but how do you think, if you were advising a CEO and building a community, what would you tell them?

Robbie Bent:
That’s a tough one. It just really is business-dependent, but it can be done. So firstly, I would say, hey, what I always like to do is look at parallels in other industries and see what you can take. And so our business specifically is a mix of group therapy, retreats, bathhouse culture, and fitness. And I went to probably 70 bathhouses and also have done hundreds of immersive experiences and retreats to try to pull out what is unique.

And so I would do the same if I wanted to build a community and look like who has the best in my space? And like, Notion is an amazing example where they enable people to create templates and become Notion coaches. And these people are so obsessed with the product, they love to share, how to get better, how to get more productive.

So it’s, what about your product? Do people want to share? So for Othership specifically, it’s the classes, right? It’s the piece of, like, wow, I did that lovingkindness class or that warrior class, and it was pitch black, and we all screamed and we felt bonded. And so it’s finding the piece of the product that is the most captivating, most magical, most passionate, most heat around, or the problem.

So I’d look at it in two ways, as, like, in Notion, okay, people really want to be organized. They’re like, obsessed. People are obsessed with productivity. So can you create a blog around productivity hacks, or can you buy a property like that that has a community around it? And so I would look at your business like, who are the top 10% of customers that are most engaged? What is the problem they’re solving? And can I create a form for them to solve it together and meet? Whether it’s in Discord or a blog or something.

So I don’t think it has to be too crazy. I think it’s just who are my most passionate customers that want to share what they’re using this for and want to talk about the problem and then connecting them. And that would probably work for any business.

Mark MacLeod:
Final question. You talk about you want to be at 100 cities, (that is) your vision. Do you have a broader vision around the impact you want to have on people, on society? A good friend, Cameron, who runs Retreat Guru. It’s a place where you can go and find, initially, wellness retreats, and now there’s a lot of ayahuasca retreats as their number one category. But their stated mission, first of all, is to help retreat owners run and grow businesses. But it’s actually to elevate human consciousness. That’s the thing they’re trying to achieve. I’m wondering, do you have a similar high aspiration for your impact?

Robbie Bent:
We do. So, we have one that’s sort of unattainable, but it’s the vision to solve loneliness. And then one sort of underneath which we’re actually striving for, is to make emotional regulation a practice that everyone does weekly. And so that idea is that you’re coming into a space and you’re practicing loving and kindness, or you’re practicing feeling despair, or you’re practicing feeling confidence.

It’s this idea that feeling into your emotions can be done the same way you go to a gym. And a goal would be that 300 million people in the US had tried this and understand that regulating your emotions weekly can be a practice. And I think that is one closer step to solving loneliness.

So, you know, the studios are just a function to help bring this to the masses. This idea that we can process our own emotions together in a collective.

Mark MacLeod:
Yeah, I love that. That’s amazing. And such a growing problem.

Robbie, thank you so much. I really appreciate you taking the time to sit with us today.

Robbie Bent:
Amazing. It was super fun. I liked the questions. It’s always nice to be transparent. Hopefully, being a CEO is just hard and it’s shitty. And I feel all the time like I’m always the negative one. I got to argue with the vendors, I got to argue with the investors, I got to argue with the employees, I got to argue with the customers. It just is like a really hard role that is not natural where you have to be the bad guy a lot.

And for people listening, like, yeah, I’m doing well, but it’s a struggle. I think sharing with somebody is like, the number one thing is getting support. So I really appreciate what you do for CEOs. They’re super lucky to have you.

Mark MacLeod:
Awesome. Thank you, Robbie!

Hey, thanks for listening to the Startup CEO Show. If you’d like to connect with me, be sure to visit my website at markmacLeod.me, or follow me on LinkedIn at The Mark MacLeod, or X account @markmacleod_, and if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We’ll see you next time.

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