Building Trust and Embracing Change with Jordan Boesch - Mark MacLeod

May 9, 2024 - Marina

Building Trust and Embracing Change with Jordan Boesch

Take a look at the transcript from my conversation with Jordan Boesch on The Startup CEO Show, who has scaled 7shifts from a nascent startup to a powerhouse with over 400 employees.

Jordan Boesch is the dynamic co-founder and CEO of 7shifts, a comprehensive HR and team management platform tailored for the hospitality industry.

Uncover Insights from This Episode

Mark MacLeod:
In this episode, I sit down with Jordan Boesch, co-founder and CEO of 7shifts.

Over the past ten years, from Saskatoon, a town of 300,000 people, Jordan has quietly built his company to over 400 people and he has no signs of slowing down.

In this episode, we talk about the journey from developer to CEO, the benefits of being a big fish in a small pond, the importance of gratitude, leaving space to make big decisions, and many more topics. I hope you enjoy this episode.

Jordan, it’s a true pleasure to be with you here today. Welcome to the Startup CEO Show.

Jordan Boesch:
Thanks for having me, Mark.

Mark MacLeod:
Yeah, we had a couple of minutes to chat before. I hadn’t seen your face in some time and yeah, this is really great.

As I mentioned kind of when we were chatting before, Startup CEO Show is all about kind of real talk for CEOs, the CEO role is the toughest role out there. It’s the only role with no kind of gradual path to get there, right?

Like I was a CFO for a long time, but there was a path to get there. There was like a body of knowledge I studied and then I had gradual roles leading up to it. You just started a company, this is your second one. I know you had one before, but now you are CEO.

And so, the place where I’d love to start… First of all, I’d love it if you told listeners what 7shifts is for those who don’t know.

But my first question really is like developer to CEO, you’ve clearly made this transition. How did you go about making it? What were those first steps like? How did you figure it out? Anything you care to share on that?

Jordan Boesch:
Yeah, of course. So first of all, for folks that don’t know 7shifts, so we’re an all-in-one HR team management platform for the hospitality industry, restaurants specifically. So everything from the moment someone’s hired in a restaurant, trained, scheduled, paid and then effectively retained, that’s what we cover and that’s how we define our world, which is more the employee journey.

In terms of that transition of developer to CEO and what I do now, I don’t know that it was really a smooth transition.

I love coding. There’s no two ways about it. I love building things. And I think that that showed in the early days when I was doing a lot of the design, development, server stuff, marketing, everything as one does in the early days. But there is just kind of this high that I personally get from shipping things and getting things out into the world.

And there’s no amount of money you could pay me that replaces the feeling that you get when someone uses your product and really loves it, gives you feedback, compliments, and how it’s saving them tons of time.

I was sort of addicted to this feeling of people giving positive or negative feedback around the product because I would just so badly want to make it better and fix it.

The journey to kind of get to where I was, it was a lot of doing the coding, and I almost break it up to three different phases. Maybe there was like the, in the code, there was like the in the business, and then there’s like, the on the business, just what comes to mind right away. But the development I kept doing until we were probably 20 people or something. And then your focus sort of shifts to the next most important thing that you need to solve for the business.

So I think I had enough engineering power, we had enough power on the team that they could kind of like, for the most part, build really great products and ship things. And then I would transition to marketing for a little bit, and then I would transition to other functions that needed some support.

But I would say largely my head and my value to the company has been mostly product. And so I tend to even still over-index on spending time there.

But I think from doing all these functions, you sort of learned, I always say you learn enough to be dangerous. You’re not the best head of marketing, you’re not the best head of product, you’re not the best engineer, but you know enough to identify who the best could be.

And then it was at that point where, because you can kind of smell bullshit from someone that’s not really great. But if someone is really great, they really start to like, you can see because you can understand the language as opposed to the challenge that non-technical founders have with hiring a technical person, it’s very challenging.

And so I felt grateful in that I knew enough to be dangerous, but I wasn’t the best at that thing. And so it was a series of iterations of getting those people on board and really just kind of growing from there and then understanding… I think the other part is understanding when people are feeling stretched.

You have that VP or you have that director, and your company doubles in size. And what are those early indicators of someone being stretched and having a hard time getting to that next level?

Because those are those moments that you want to get in front as much as you can. And I think being able to see and spot those signs, they don’t really change as you grow the business, they’re the similar signs. So I think that is a lot of like, rinse and repeat of that type of process, and here we are a much bigger company, but with a lot of smart people around the table that I have the good fortune of working with every day.

Mark MacLeod:
Amazing. I love that. Are you allowed to contribute code anymore or are you banned and you don’t know the login?

Jordan Boesch:
Actually, funny story, I wrote a comment on GitHub being like, hey, did we use this library? Blah, blah. Like, it should have been this. And it was a total joke. Like, I was referencing an old legacy library that we should be using this.

One of the developers I found out later was like, hey, is Jordan serious? And all the devs were like, what’s going on? And then it got up to our head of engineering and he goes, Jordan, I just want you to know that people are so confused by that comment… You and I think it’s funny, but it was super confusing to them. By the way, your GitHub access is turned off effective immediately. And I was like…

Mark MacLeod:
(laughs) That’s awesome.

Jordan Boesch:
I sort of said like, that’s fair, that’s fair, I get it. But when I told the devs that it was just a joke, they thought it was funny. But because I’d never interacted with them on that level, and I’m coming in for the first time saying something, everyone’s like, is he serious? Anyway, so that’s when I got my access revoked, it was from me, just like trolling the devs on a code review.

Mark MacLeod:
Is humor a part of your culture? Like, would people even know to just expect you to be humorous in a situation?

Jordan Boesch:
Yeah, look, I would say prior to the pandemic, yes, but I would say because half the company is remote, it’s really hard to spend time with people or bump into people in the hallways. And you kind of have that small chitchat. And in those micro interactions, you’re building trust and they’re getting to see you and you’re getting to be more human.

But when I just Slack someone saying like, “Hey, I have some questions, can we hop on a huddle?” it’s like, “Oh my god, what does he want to talk about?” And you get in the huddle and it’s like, nothing crazy. I would say that prior to the pandemic, very much so. And then I would say post-pandemic, it’s been challenging for me and I think others, just given the nature of the work, and I think a lot of people miss those in-person interactions and trust-building.

Mark MacLeod:
Yeah, I think. Yeah, for sure. A lot of my CEOs really wish everyone was back under one roof or other roofs if they’re too big to be under one roof. But, yeah, everyone thinks that nothing beats the in-person interaction.

Jordan Boesch:
The office doesn’t necessarily need to be the place where work happens. It’s more about what is that kind of rendezvous point, that jumping-off point where people can come together, whether it’s an event, whether it’s for team-building, and then either do it there at the office or go somewhere else.

But I think that that’s where we think is the real potential is around those moments of not seeing the offices like you need to work here, but look, if you have a team event later on that night and a bunch of people are in the same city, yeah, it makes sense to go to the office and work together for the day and then after you go to that event. But I think we all value the flexibility and understanding how to strike that balance is really important, I think, for the future of work.

Mark MacLeod:
Do you exercise that flexibility yourself?

Jordan Boesch:
Yeah, I do.

Mark MacLeod:
Good.

Jordan Boesch:
Look, in Saskatoon, which is where I’m based, everything is 15… Like at most is a 15-minute drive from the office, and I live a 20-minute walk from work. And some days I’ll stay at home, some days I’ll come to the office. It doesn’t make a huge difference. But some days, I would say most days, I do like to just spend time in the office because it just gives me a different place to work. But again, it doesn’t need to be for work. That’s just how I use it.

Mark MacLeod:
That’s great. That makes sense because I see many, a lot of employees love the flexibility, but then the CEO is kind of in the office, and so there’s just a disconnect in behavior, right? So good to see that there’s consistency.

Jordan Boesch:
I think talking to other companies, too, there’s a lot of challenges around hiring junior folks that are starting remotely and having a harder time kind of ramping and getting good senior mentorship.

I know of a bunch of companies that just stopped hiring junior folks because it’s too challenging, because, A, not everyone’s good at working remote, and I think that’s just, like, a good thing to call out, and B, some companies don’t want to take that risk on whether or not that person will be good, and then C, it’s compounded with, like, that person is completely new to this field, and they’re going to need good mentorship, good leadership along that journey to get them to pass their probation.

And so it’s really doing them a disservice if you’re not able to provide that because they don’t want to fail, right? But you also need to give them support so they don’t. And understandably so that people are concerned about how that works in a remote environment because it is more challenging. It’s not saying it’s not possible, it’s just more challenging.

Mark MacLeod:
No, I totally agree with that. And when Covid happened, I was still running my investment bank, SurePath, and we went remote. And I noticed a real difference by, let’s call it age and life circumstances. I was the oldest guy. I went remote. I had a beautiful home. I had like a dedicated home office. I was fully set up.

One of my analysts, he’s using his kitchen table, sharing it with his roommate, who’s an analyst for CIBC. And they’re both there pounding, trying to figure out how to be on conference calls at the same time. It was just hard to be remote if you didn’t have a great home-office setup. And then of course, it just also requires a decent amount of self-discipline. And if I completely generalize, that’s something that comes with age. So I think it’s harder, going back to your point about junior folks. They may not have the right home set up and they may not have the right maturity level yet. And that sort of just is what it is.

Jordan Boesch:
Totally. Not for everyone.

Mark MacLeod:
When you were talking about your path from the developer to CEO, you touched on a really important subject, which I think every management team struggles with and every CEO struggles with, which is signs that the leaders who were once great are no longer great and are not keeping up with growth.

These weren’t the exact words you used, but you talked about the signs. I would love it if you could decode if you have, I guess, a shareable formula, like how have you figured that out for your company?

Jordan Boesch:
I think it compounds in ways that… It depends on some roles that are very quota-driven roles. It’s like targets are being missed and those are sort of like outcomes or, sorry, those are the outputs of some of the behaviors that you can maybe look for, but I would say stress is kind of a good early indicator too, where folks are stressed about hitting the big numbers, or…

Mark MacLeod:
Do you actively ask people about stress levels?

Jordan Boesch:
I don’t, but I think it’s a good question to be asking people, I think, even just how they’re feeling right with the upcoming year and what’s exciting for them and what’s terrifying for them. And I think me sharing openly as well, I think that might be a good trust-building thing. So thank you for the idea, Mark.

Mark MacLeod:
You’re welcome.

Jordan Boesch:
Yeah, I would say it manifests its way in some emotions. And I would also say some of the biggest challenges is when folks aren’t hiring people better than them, right?

I think that it’s a very big difference in terms of folks being able to say like I’m bringing this person on and that person doing like a 10x or not 10x, but massively stepping up and accelerating that function, maybe that department and making that leader look really good.

I think a lot of leaders that feel stretched and maybe are hitting a bit of a ceiling start to almost spend more time too deep in their teams of micromanaging the lack of great people that are kind of pushing their whole team forward.

And so in their mind they’re like, well, I’m so busy, I’m so busy I’m always working. But you’re working on kind of pulling up maybe people that aren’t performing to the level you need them to perform and you’re just constantly picking them up. And you don’t want to be in a state where you’re constantly picking people up.

You want to be in a state where these people are being proactive and they’re over-exceeding and they’re delivering against what you hire them for so that you can look good. Ultimately it’s a reflection on you leader, on how your team is performing and how well you managed and hired up on that team.

But yeah, I do think those are some really key signs that at least I typically look for is kind of like the stress, the kind of deep worry, but then also how they’re setting their teams up and do they know what to do next? Are they thinking about the next six months, twelve months, and what do they think is going to come around the corner?

And I think there is a level of attempted predictability that people go through in their head of what should I need? What do I need? All I ask is I think that you do the exercise. It doesn’t have to be perfect. It’s not like you’re not going to hit ten out of ten, but do the work.

And the more times you’re right, the more trust you build and you accumulate much like founders, right? The more decisions you make that are the right decisions, the more trust you get at the board level and the more freedom and flexibility you’re going to get. I think ultimately we’re just trying to build trust through a great track record, and how you do that is important.

Mark MacLeod:
Sounds like Toby’s concept of the trust battery. Are you familiar with that?

Jordan Boesch:
Yeah, yeah. When they come in, they’ve got kind of half the amount of battery and spends time with them, kind of divulging the information of that function and kind of getting their arms around it as quick as possible and then letting them kind of flourish. I’m a big believer in that.

That’s kind of how I like to manage, is when a new executive comes in, like, look, I have a lot of context, and I’m not saying the decisions that I made are right, but if at least you can come in knowing what I know as fast as possible and married with the skill sets that you are going to bring in, then I have infinitely more trust that you are going to run quicker than otherwise.

You shouldn’t have to learn the same things that I already know. It’s not going to be a great use of anyone’s time.

Mark MacLeod:
Yeah. The key word for me is leverage. Anyone you’ve recently hired. I know you brought on Paul Marshall, who’s a friend recently. Anytime you bring in a direct report like that, it should be leverage. It should move the leadership team, should move you to another level. Yes, you have to invest. You have to onboard Paul. You invest in that relationship, and that theoretically slows you down. But it is an investment, right? It’s going to actually pay in terms of leverage and momentum and speed.

And the same is true all the way down. So that’s the big thing I look for. And you talked about those leaders being busy and being like, look how busy I am. I actually find that part of that busy-ness is to avoid facing the truth, which is that I’m failing to keep up.

And so I’m keeping busy in this comfort, this stuff that is at the wrong altitude, but it’s comfortable. So I’m just going to stay there versus going out of my comfort zone. Those are the signs that I look for.

Jordan Boesch:
Yeah, very, very true.

Mark MacLeod:
On this stress thing, back to more free ideas. I know some leadership teams that when they meet for their weekly meeting, they just go around the table and be like, I’m three out of five on stress. I’m like, I’m a five out of five. Each person, just like, even before anything else, we just do a temperature check on where they’re at.

And so now we know if Joe blows a five out of five, and he said so at the beginning of the meeting, and then he’s getting hot and bothered in the meeting, we know why, you know, we have a bit more compassion for him.

Jordan Boesch:
That’s very true. And, uh, yeah, I may steal that idea as well, yeah. Is there any other questions that they ask or is that kind of the primary one to gauge?

Mark MacLeod:
That was it, that was it. Just a check-in. You know, “where are you at today?”

Jordan Boesch:
I see.

Mark MacLeod:
That’s it.

Jordan Boesch:
I actually know that other teams do that, but not my first team. So I think that that’s a super interesting call.

Mark MacLeod:
Yeah, cool. You know, you talked about some of the changes that Covid brought on, notably now half of your company is remote. The restaurant industry wasn’t a great place to be during COVID I wonder if you could just tell us about that and how you came out the other end.

Jordan Boesch:
Yeah. Covid was a horrible time for the restaurant industry. Restaurants closed in droves. Medi didn’t recover from this kind of blow. And I just saw a ton of resilience, though, at the same time, and as horrible as it was, it did something positive for the industry and it allowed a lot of folks to pivot pretty quickly because the restaurant industry has always had a hard time adopting and adapting to new technology. And I’m not convinced it’s because they thought it didn’t exist, I just don’t think they put the energy into understanding it because it was always like a cost.

And when you’re operating in a landscape with such low margins, everything that costs money, you’re kind of just turned off to. And many large brands and CFOs of these brands and VPs of operations, they get it because they work in a spreadsheet all day and they’re just kind of like crunching numbers. But that is not what the average independent is doing.

But I do think that we saw a bit of a shift as folks adopted more delivery services like Doordash, or SkipTheDishes, or Uber Eats, or any of those delivery services, those folks had a hate it like 3x their business overnight. It was just, they were having a great time. But we did see more folks that were willing to explore what’s out there. What else am I missing that can integrate with this tool that I just bought or that can save me more time and money that’s going to help with my bottom line.

And I was really energized and optimistic that this is going to change the industry for the good. And yeah, people that were kind of riding the red and the black, yeah, they went out of business, but some of them shouldn’t have been in business because they just failed to adapt. And I think that the next wave of operators coming in are just so much more tech-savvy, and they’re kind of leading with, like, what does my stack look like? How do I optimize this?

And it’s a pretty refreshing feeling. But, yeah, it sucked. They all got punched and kicked a lot during COVID, and in terms of how we navigated, we lost about six months of revenue. It put us back about six months, but then after that, we had to furlough a quarter of our staff at the time, which was 40 people, and yeah, it sucked.

But then after that six-month mark, we got to bring people back. We brought, like, 90% of those folks back. We didn’t raise prices, obviously. I think that’d just be a very slimy thing to do during a time… If the restaurant industry is going down, we’re going down. I don’t know, but we believed in restaurants long-term, so long as people are going to be social and need to eat, then we believe in restaurants.

Mark MacLeod:
That’s not changing.

Jordan Boesch:
I don’t think you’re going to change, like, millions of years of evolution and be social in a year. And so I think we just did right by our customers, we offered them discounts, we gave them the task management product that allowed them to do sanitary checklists and all these things that would help them operate more effectively.

We saw an uptick in messaging where people were sending out forms, government forms that employees could get some reimbursements for their wages, and we saw a lot of good behavior. And the app used for that primarily.

But all these considered, it made me so grateful more than anything to have the team that I had around me that were so resilient and were sort of like, I could just see they were just, like, rolling up their sleeves, like, virtually. They were just like, what do we need to do? We got this.

And everyone banding together, even, like, the leadership team all the way down were sort of like, we got this. Even though this crazy turmoil was happening around us, I never felt that way within my team. We were having board calls every week, just constant checking in on how the business is doing. But not once did I feel like there was, like, doom and gloom. I felt, like, so fortunate just to have the people around me.

Mark MacLeod:
Oh, that’s amazing. You brought up such a powerful word, gratitude. I’ve dealt with founder CEOs for 24 years now, and if I stereotype, often they have such a clear vision of the future that is so far away that they’re not actually really happy or grateful today because they’re just so dissatisfied at the gap between here and the vision.

Jordan Boesch:
Are you in my head right now? You were totally in my head.

Mark MacLeod:
My thesis is like, well, gratitude is deeply powerful, and every day there’s something to be grateful for, even if it’s on the hardest days. It’s like, well, I made it through today, tomorrow is going to be better.

Just wondering, how does gratitude live for you? And is it a thing? Is that a muscle you need to develop? And then also just the power of praise, right? Especially from a CEO. And do you take time to acknowledge the good things that you see along the way? Or are you just kind of so hard-focused on the vision that, again, is still so far away?

Jordan Boesch:
Mark, I’m bad at both of those things, to be honest. And starting with gratitude, it is a feeling of sort of you’re kind of just chasing this invisible unicorn into a rainbow that you can see, but you’re always chasing it.

I’m guilty of not stopping to smell the flowers and just being like, wow, this is a nice flower. I’ve been told that before, and it’s so true, and it’s something that I do need to personally work at and get better at. And even with the praise side of things, it’s like I don’t give as much praise as I should, and a big part of this, I think, has to do with, like, that just doesn’t motivate me.

The mistake is that that doesn’t motivate others. And it is a mistake because I’m sort of like, maybe you could almost bring it back to even the five love languages, right? In terms of how people feel that they’re being appreciated.

Is it gifts? Is it words of affirmation? And I think me spending more time doing that, it’s so easy to do and can mean a lot for someone. But admittedly, I haven’t been good at it for many years because of, again, because that’s not how I get motivated. When someone says, like, good job, Jordan, it doesn’t register. It’s just floats away. And so now you can maybe make an argument that I should learn to internalize that and maybe there is something there instead of me kind of focusing on the next thing that we need to do and feeling like there’s, like, kind of a never-ending list.

Mark MacLeod:
Yeah. I mean, to me, you’re ten years in. You have 400 employees. You talked about losing six months of revenue during COVID having to get rid of a quarter of your staff by my very quick back-of-the-napkin math, you’ve more than doubled in that short time. And so I think there’s a lot to be grateful for.

This is actually a business that you could theoretically run in perpetuity. I think it’d be mathematically impossible for you to run out of addressable market, and so you could keep doing this for a very long time, in which case, I would say gratitude, and just acknowledging where I’m at might, in fact, fuel me to keep going in perpetuity.

Jordan Boesch:
Yeah.

Mark MacLeod:
Versus it just at a certain point, that slog and the destination is always like, there’s always a desert to cross. At a certain point, you’re just like, oh, man, I’m just done with sand. I’m over. It’s over, right? On a beach and be in real sand.

Jordan Boesch:
I’m done pounding sand. 🙂

Mark MacLeod:
Yeah.Then a buyer just happens to show up at that moment of weakness, and you’re like, screw it. I’ll take it. It happens.

Number one reason, as a guy who sold a lot of businesses, number one reason why founders choose to sell, there’s different than when you have no choice but to sell, is because they’re burnt out and they can’t actually sort of separate themselves from the business. Theoretically, it’s an asset. I could just replace myself, and it’s now a thing that goes on and lives without me. But very often, they’re just like, I’m done. Let’s just find a home.

And so I actually think that gratitude is a powerful antidote to not burning out. You can’t be grateful and unhappy at the same time. This is not about brainwashing. It’s just acknowledging. It’s reframing. There’s always something to be grateful for.

Jordan Boesch:
Should I cancel my appointment with my counselor tomorrow? Because this is good stuff.

Mark MacLeod:
(laughs)

Jordan Boesch:
It’s all great, free advice.

Mark MacLeod:
You have a couch behind you, if you want to lie on a couch we could just keep this going.

Jordan Boesch:
I’ve got a drum set in the corner. That’s, like, my way to kind of just reset and recharge is through music. And so, really, I came here last night, actually, at, like, 07:00 PM And just kind of wailed away on the drums. Anyway, sidebar, but…

Mark MacLeod:
Fun fact – In high school I was a drummer in a rock band. This was blissfully before social media because I had long, permed hair and I had lumber jackets where I would cut off the sleeves so you could see how big my arms were, and they weren’t big, and I had, like, leather studded wristbands. Anyway, it was a shit show. It was so bad. But anyway, we’re both…

Jordan Boesch:
Let’s dig up some of those pictures. Yeah. And Mark’s going to put them on the screen right now for everyone to see.

Mark MacLeod:
(laughs) No.

Jordan Boesch:
All right, there we go. He’s going to edit them on the screen. Perfect.

Mark MacLeod:
No, he’s not.

Jordan Boesch:
Yeah, but, yeah. No, I think that’s very true. I think I’ve definitely experienced moments of exhaustion and burnout. It’s an interesting thing where I’ve even had investors say, just go take a vacation. And I still am struggling with the best way to kind of get through those moments, because the best feeling is, like, overcoming them, right? And going away to a destination. They’re still on your mind unless you become really good at shutting them off.

But for me, it’s that blessing of the curse of, like, it lives there until I deal with it, and then it’s only when I deal with it that I don’t feel the burnout feelings anymore. And I sort of almost relate it to at times when you’re just sometimes worried that you have anxiety around having a confrontation with someone or the obstacle is normally the way. Whatever’s standing in front of you is what you have to do. You have to tackle it head-on.

And you’re not going to get through life if you’re not having confrontation and where it needs to happen in a healthy way to try and get to the root of things if you’re bottling everything up. I’ve been always a believer of just taking things head on, and that’s been my way of coping with a lot of weight of things, is just deal with it, get through it, plan what you need to do. And that period after that thing is dealt with is actually, like, way more liberating, and I’m not in a tropical destination, but my mind is in such a better place.

Mark MacLeod:
Yeah, listen, I see both sides of it. I agree with what you said. The obstacle is the way. I feel like that should be a book title, maybe it is already.

Jordan Boesch:
It is, actually.

Mark MacLeod:
That certainly sounds stoic and I can clearly picture, okay, I get through that obstacle, and then now I take the break. Now I can fully relax. But what you described, that notion of, it’s just churning in my mind. I can’t relax until I deal with it. It’s just illustrating not being present. There’s always going to be an obstacle. And then I would argue by taking time to kind of charge/refresh regularly, when you tackle the obstacle, you’re going to be far better able to do it. I always talk about CEOs of venture-backed startups are like professional athletes.

You have the same expectations on your shoulders, right? You’ve raised a meaningful amount of capital. There are return expectations attached to that capital. And you look at pro athletes, what do they do more than anything else? They rest, they come in, they crush it. They rest, they come back, crush it. You know what I mean? Now, slightly different thing. It’s not a physical thing, but you’re a mental athlete. And so it’s the same thing, especially for a CEO.

If you actually look back, there’s probably a small number of really big moments or really big decisions that move the needle. The more clarity and crispness that you have in your mind at those moments, the better those decisions are going to be, the easier they are to make. And so it’s not to sit around and get massages every day and work 4 hours a day. But I think most CEOs over-index on grinding and under-index on kind of investing in themselves and recognizing that they are mental athletes.

Jordan Boesch:
I agree. I think my ability to tap into the mental, present in the moment and being able to almost compartmentalize things in a way so that you can kind of be present is so hard. So hard. And yeah, I’ve definitely struggled with that. Personally, I think now having two kids, a three-year-old and a five-year-old, it’s even more important now than it ever was.

Because you get home, you want to play with your kids, you don’t want to think about the three fires that you need to put out at work, even though, and there’s nothing you can do in that moment either. You can’t do anything there anyway.

So you’re right. I would love to figure out how to develop that muscle a little bit better. And part of it to me, that I’ve actually learned about myself over the years is because there’s a problem, I like to go solve it. Actually, sitting with that problem for multiple days is an interesting challenge for me. I’ve done it a few times now, and it’s been so helpful because the way I would have tackled that, if I would have reacted too quickly, would have caused so many other ripple effects within the business.

And I’ve been there, I’ve done that, and it’s not great. And I’m like, if I’d have taken a couple of days to just really think about what is the best course, I would have done that totally differently. So the downside is, okay, I’m living with that feeling, and I don’t like that feeling.

That’s why I always want to do it. But it’s like being comfortable with that feeling and getting that comfort was like a really big thing for me that once I did it a few times, I started to be, oh, like, I can perhaps teach myself how to do this and be better for it so early days, but I’m finding there’s a bit of that that’s happening now.

Mark MacLeod:
So many of us operate with brute force. We’re just going to clear that inbox, we’re going to respond to every Slack message, everything that comes in, we’re just going to pound it. But then, first of all, our brains aren’t designed to work that way. And second, we’re only actually using our rational brain.

The thing that happens when you sit with these problems for, especially overnight, is you give space for your intuitive brain to go to work. And that’s why when we go on a hike or we’re in the shower, we have these “a-ha” moments because we’ve actually given that space. And our intuitive brain is so much more powerful than our rational brain. Our intuitive brain just knows. And so when the solution comes, it’s obvious. It is actually super helpful to create that space. But you’re absolutely right, it’s uncomfortable.

And we have trained ourselves… I’m speaking about society at large now—to have instant kind of hits, instant dopamine response. I’m guilty of it myself. Like, I’m writing an article and just like, oh, let me go check the price of Shopify’s stock, or let me see who’s, like, I interrupt myself and this is a guy who’s got a daily yoga and meditation practice, and I still do it. So we actually have to create good mental habits.

And so it’s super hard. Meditation is a thing, even if it’s five minutes a day. You don’t have to go into a cave for like a day at a time or something. Just the five minutes just trains your brain to know what it’s like to sit in space. Obviously, we all. Well, I work at home now. I found if I would finish my work day and bring my phone with me, I’d just keep checking it. And so now I just leave it here in my office.

Unless there’s an emergency, it’s off. You know what I mean? When I’m off, and I’ve certainly found that there are very few things that are so urgent. Like if a CEO’s got an issue, they’re going to text me, I’ll hear the ding. All my devices will ding. I don’t need to go and proactively check and see if there’s an issue.

So I’ve learned through creating that space that, oh, it’s actually, the world doesn’t fall apart, so it’s just little things that I’ve done. But the big thing that I think comes from that space that you’ve created, where you sit on problems, is tapping into all of your capability, not just that rational, short-term processing power, if that makes sense.

Jordan Boesch:
Totally.

Mark MacLeod:
You’ve kind of very quietly gone about building a 400-person company. You’re in Saskatoon, which I’ve never had the pleasure of going to. And you talked about these three phases, you were in the product, in the business, on the business. Any other keys to your success? How have you gone about, how have you done this?

Jordan Boesch:
I think if I were to boil it down, really, I have a passion for the space. I have a passion for solving customer pain points. I care deeply, and I always wanted to build something in a place where people didn’t think you could build something. And there’s a bit of prairie pride in building here that I have, because there’s advantages, there’s inherent advantages around the community aspect. This is a city of 300,000 people. There’s great… Yeah. And there’s, like, people know us at the university and the engineering programs, and there’s good, great talent that we could have access to coming out of there.

I think also when we raise money or when we do something, it’s a big deal in the community, and people take note. And I think that we’ve chosen to almost be like a big fish in a small pond. And I think with that comes some interesting opportunities. And I fundamentally believe in giving people opportunities.

And I think that there’s a lot of folks here. There are a lot of folks here that work really hard, but they’ve just never done that thing before. And I think that there’s something admirable about this prairie grit that you see where it’s like, everyone’s parents were like, farmers, and you just got in there and you got shit done, right. And I think that I just love that about the people here.

And I think that we’re just trying to use that to our advantage. It’s like, okay, well, you’ve never done that thing before, but you’re working insanely hard, and you put in the time and the energy to do it, and let’s build that together. Let’s learn. Like you’re going to learn. You’re going to grow faster than you’ve ever grown in any other career you probably could have taken on. And also, let’s build that community in the process. So let’s bring people here, let’s fly them out, which we’re going to get back to doing more of this upcoming year.

We used to fly out speakers from Shopify or SkipTheDishes. And it was really great because I love when an ecosystem thrives and can continue to learn. And similarly, in some aspects, we have a hub in Saskatoon, we have a hub in Toronto. And I think there’s an opportunity to continue to win by solving customer pain points, hiring great people, and kind of making it a place where they want to work and do some of their best work.

And so that’s, I would say, I don’t know if it’s a good or bad thing that we’re low profile in the prairies, but I do tend to think that the good is that is all those reasons I mentioned, the bad is that man flying out of Saskatoon sucks getting anywhere. It just sucks.

Mark MacLeod:
(laughs) There’s no direct…

Jordan Boesch:
I mean, Toronto is normally where we do our board meetings. We do all our… A lot of events and leadership planning because it’s a direct flight for a lot of the folks that are leaders in the U.S. But yeah, we think there’s tremendous potential to build here.

Mark MacLeod:
Hearing your answer there made me actually think about Shopify in the early days. You know, Shopify is dispersed now, but for years they actually viewed being in Ottawa as a strength because they quickly became the tech employer of record, right? If you were a computer science grad, you just wanted to work at Shopify.

Eventually, they were forced to expand. A, just through a sheer availability of talent. But the weak link was actually on the leaders, right? The bin there, done it. Got the T-shirt. People who truly understood scale just lived elsewhere. And that’s why they had kind of Craig and know they built around different folks.

You’re describing a similar journey, but I definitely see the benefits of being a big fish in a small pond, that’s for sure.

I want to switch gears as we kind of get into the tail end and talk about… I want to selfishly bring up Danny Meyer as a guy who’s been in the service business for a long time, I read his book “Setting the Table” many, many years ago and have tried to model… I didn’t run a restaurant, but how I delivered service around that.

And it struck me there was a very values-driven approach and very high standards. I’m just wondering, has there been any impact in your company from dealing with his company? Has that values or service orientation rubbed off or what drew you to him? Anything you care to share on that experience?

Jordan Boesch:
Getting investment from Danny Meyer for our Series B was… the highlight for me was being able to work with him on what we’re building. And I think that I personally value a lot of his thinking around teams, and around culture, and the importance of your front line. And I think that he is not above anyone in the way that he comes across. And I just admire that style of leadership. And I think that a lot of folks can learn a lot from his humility and how he approaches it.

And also just some of his sayings as like a former software developer, when he talks about what culture is—culture is the sum of all the behaviors you celebrate minus the ones you tolerate. I was like, that is so good and it’s so true, all those behaviors that you champion, but you’re going to tolerate some slippage.

But the outcome of that slippage is your culture. And I think that resonated with me a lot. I also love his analogy of the salt shaker, like putting the salt shaker back in the middle of the table when folks are not demonstrating the right behaviors they talked about in restaurants, when the servers come in, the busters come in to clear the table and wipe it down. And, well, you need to put the salt shaker back in the middle of the table because it got pushed everywhere.

And his management philosophy is very much, if you do notice a behavior that is not aligned with our values, put the salt shaker back in the middle of the table. And that really resonates with me as it relates to our radical candor value of care personally challenge directly. And that to me is really the salt shaker analogy. And so those are some of the big things that I really took away that I talk about very frequently in the company. And I think they’re really critical.

Mark MacLeod:
Love it. That’s powerful stuff. I talk about values a lot with my CEOs. I think for most companies, values are not fully lived. If we were in offices, they’d be hollow sayings on posters that are not really lived. I actually think they’re so important that any disagreement, any lack of alignment can be traced back to an unarticulated or unlived value. So that’s just how I see them.

Jordan Boesch:
Yeah, I think everyone should… What’s interesting is when the culture is strong and people are displaying the values on a regular basis, it’s like palpable. You feel it. And when someone gets thrown in the mix that isn’t a values fit, that is not aligned, they just get repelled by the company. I’ve seen it happen, and it’s like oil and water. It’s crazy. And so I think to Danny’s point, when you allow a lot of the things, if you tolerate too much, the water becomes gray and murky. And then no one really can call each other out on not displaying the values because you let too many behaviors ride.

And now no one knows what to do. And so adhering to those on a regular basis, celebrating them like we call them out an all hands, because people are submitting them in real-time. They’re always submitting stories. We believe the best way to reinforce our values is me curating, going and reading all these core value stories that people submit every month to a public Slack channel, grab the ones that are like the best demonstration of that value, and then read them and celebrate that person at all hands, and read that story and tell people why.

Because you can get different interpretations of that value. And we try to make them behavior-based so it’s more clear. Like, we avoid words like respect. It’s not a bad thing to respect people, but what does respect mean? What are you trying to get at? Well, I want people to respect when I’m talking to me, it’s like, okay, so you care that they’re a good listener? Okay.

And then for us, we would say, well, the value is being a great listener. And so we’re trying to dissect those large, ambiguous terms that big corporations use down to something that is actually the behavior. And then defining that behavior and then telling stories about that behavior and reinforcing it has been helpful.

Mark MacLeod:
There’s so much more that I could ask, but we’re running out of time and you have a company to run. Maybe, final question, advice to your younger self. You’re ten years in, you kind of figured this out as you went. If you were going back in time with all of the capability that you have today, but it was ten years ago, what advice would you give yourself to operate differently?

Jordan Boesch:
I would say trust your gut more. I think that my gut has been pretty right over a lot of things. And sometimes I doubt it because I want to sit on more data, get more stuff. There are time and places for that. But I think that generally, I think trusting my gut more. I think also just not being afraid to make changes and stand behind them and be clear and communicate the why and then repeat it ten times.

Mark MacLeod:
As you grow, right? The repeat is so key as you grow.

Jordan Boesch:
Yes. And again, I think people appreciate more direction than ambiguity, and direction without explanation or transparency, is not going to be well-received. But if you are really transparent and you’re articulating as to why, people still might disagree, but they at least feel like they have the full context.

Mark MacLeod:
Awesome. Jordan, thank you so much for making the time. It’s a pleasure, and I’m so thrilled that the company is doing so well. I meant what I said. You could run this thing forever, and I kind of hope that you do. Thank you so much.

Jordan Boesch:
Thanks, Mark!

Mark MacLeod:
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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