Jordan Boesch (00:00:00):
It was never about making money or like having, you know, stability in this way it was more I was fueled, and I continue to be fueled, by solving problems and people going, "Wow, this is really helping me thank you so much." I think, yeah, you can't be scared of fucking up. You know, we screwed up a bunch of stuff while we were building this, but we learned a lot. It wasn't the end of the world. 


Previous Guests (00:00:25):
That's product market fit. Product market fit. Product market fit. I called it the product market fit question. Product market fit. Product market fit. Product market fit. Product market fit. I mean, the name of the show is product market fit.

Pablo Srugo (00:00:34):
Think back to the last few months, the last few years as you've been running the startup. How many different founders have helped you out? The reality is founders help each other out, that's just who founders are. They pay it forward, so help a founder out. Take literally five seconds, take your phone out of your pocket and hit five stars. Jordan, welcome to the show, man. 

Jordan Boesch (00:00:53):
Thanks for having me. 

Pablo Srugo (00:00:54):
So, 7shifts, is now massive. I mean, it's used by like 50,000 restaurants. In fact, my brother-in-law is a recent immigrant here to Canada, and he got hired by a restaurant. And he started telling me how he uses this app called 7shifts. And I was like, oh, shit. I'm talking to the founder and CEO. And so, you've become like, big and just, like, prevalent, you know what I mean? You're used in so many places. But it started like, I mean, I guess like all things, it started small. And my understanding is like your dad was in that like restaurant world. And so, you kind of lived and breathed it before you ever started this company. Tell me a bit about kind of that story and how you kind of got into the space in the first place.


Jordan Boesch (00:01:32):
So my dad ran some quick service restaurants, Quiznos, and my grandparents also ran quick-service restaurants, Orange Julius. So I grew up working in them, enjoyed those milkshakes early on, even if they weren't the most healthy, made with that powder stuff. But anyway, we grew up working in them, myself and my siblings. And so, really started to notice, especially when working with my dad, some of the pain points that he encountered, when it came to running his first quick-service restaurant. And the scheduling, the communication, availability were just really prevalent challenges within what he was trying to do on a daily basis.

Pablo Srugo (00:02:19):
How young were you when you started noticing this?

Jordan Boesch (00:02:21):
I was just finishing high school, so 18, I guess. And I had always been a big gamer at the time, so I was addicted to video games. I was playing some games, building some new websites for my teams on these video games. It really taught me everything. How to build websites, and even if they were really crappy at the start, I was using Flash and anyway, Flash is not a thing anymore, but dating myself a little bit. But it really, it taught me those beginning fundamentals of how to build something. And so, without that small amount of learning that I'd done, I just thought, "OK, well, I can just help my dad build something like this, and it's really straightforward." So, that was version one of 7shifts was actually called Employee HQ. It was sort of a spinoff of the name. I think it was Basecamp at the time, had like BasecampHQ.com was the domain. I'm not sure if the 37 Signals guys still have that, but that was the first version, which is basically allowing folks to all log in with the same email and password and then download the Excel spreadsheet that my dad would upload through the app that I had built initially.

Pablo Srugo (00:03:35):
And what year was this?

Jordan Boesch (00:03:36):
God, this must have been probably 2006, 2007, maybe. So, really a long time ago.

Pablo Srugo (00:03:46):
And you're in college, university while you're doing this, or what's the kind of setup?

Jordan Boesch (00:03:51):
I was still living back home, this was right before I decided to go to college. I never had the marks for university. So, I never got into university, the ones that I applied to, I eventually got into. I started dating my now wife and co-founder. Andre, she's also from, we went to high school together. She got a scholarship to go east to the university of Ottawa, and I was like, well, I can go to. I'll try and get into a school there. So I got into Algonquin college, a multimedia program. Took a couple of years of that. The whole time that I was there, I was building websites for other companies, doing some consulting, trading projects with other classmates. You know, I didn't want to do like my audio projects. So they're like, "Okay, you do my web project,  I'll do your audio project."

Pablo Srugo (00:04:45):
Sweet.

Jordan Boesch (00:04:45):
Great deal. I was always programming, always tinkering with frameworks and new tools to try and, understand them. I'm still fascinated by programming languages and the ability to build something with code. I think it's just so magical. 

Pablo Srugo (00:05:02):
And so, when do you start like really getting pulled to what then became 7shifts? 

Jordan Boesch (00:05:07):
It was always just a side project I was doing and, my dad was the only one using it. Over the years I built some other apps.

Pablo Srugo (00:05:13):
And was he using it? Was he getting like real value or was he using it because you built it?

Jordan Boesch (00:05:18):
I mean, he kept using it while I was gone. So I would assume that it was valuable. So, I got some jobs in Ottawa working at some web design consultancy firms and, you know, learned new programming frameworks, rebuilt 7shifts, and like another framework. Again, for me, it was a passion project. It was just really fun. To learn something and put it online, and see people sign up. That was sort of a, it was very much bootstrapped. Like I would come home from my nine to five job and I would work, you know, six to one in the morning. Then I would get up and go to work and then do that again. On weekends I would be building. And so, 

Pablo Srugo (00:05:57):
Building seven ships specifically, or you're building many different things at that time.

Jordan Boesch (00:06:01):
Building 7shifts specifically because it started to get a little bit of traction. And I'm like, oh, my first customer outside of my dad was an A&W location in Vancouver, or sorry, it was in Richmond, BC. And I was like, this is so cool. I got to call this person and, I called them and built a bit of rapport with them. And, you know, it was just really exciting.

Pablo Srugo (00:06:18):
Did you close that customer without talking to them first? How did you get that second customer?

Jordan Boesch (00:06:22):
Correct. So it was a product-led motion in the early days and, it wasn't called product-led. They signed up and I called them. You know, they signed up, they used it, they paid, and then I called them. Learning and keeping close with those initial customers was really important. They all had my phone number. We chatted about a bunch of stuff, feature requests, support requests. Yeah, it was really cool. Just got to have this project where people were getting immense value. It was never about making money or having stability in this way. It was more that I was fueled. I continue to be fueled by solving problems and people going,  "Wow, this is really helping me. Thank you so much." That's really what energizes me.

Pablo Srugo (00:07:09):
You think that's important? I mean, these days, especially with startup culture being what it is, like romanticized, or whatever you want to call it. There is so much of this. I want to build a business. I started in 2013. I want to build a unicorn. Then you go out and try to do it. You hear your story. You hear how Toby started Shopify, how Zuckerberg started Facebook. It's a lot more haphazard. It's more like, Oh, just building stuff that was cool, and people started using it. And then obviously at some point you start, you know, really kind of pushing versus just like getting kind of some pull. But like, do you think that that is important? Do you think that something is like lost when you overly trying to create something big versus just building for the sake of building and kind of landing on a great problem solution set like you did?

Jordan Boesch (00:07:58):
It's hard for me to say. I think like everyone has sort of their own motivation of why they build something. And I'm not a hundred percent sure like that you can say just because you wanted to get into it for this reason, that it's a bad reason and it wouldn't work. Like I also, you know, there's also, there's stories like mine where people are very passionate at the beginning of what they do and they, they sort of channeled that passion to build something. Yeah. And then there's stories of folks where they were sort of like looking for problems and then they found a really big problem and then they were like building and then they got passionate over time. They weren't passionate that fueled the initial build. They were sort of like fueled by the problem and the problem space and the opportunity. I don't know if it, I guess I, I don't know if it's like a problem or just, um, you know, different types of approaches. And, um, yeah, I think that the, the, one of the big things that I learned as we were building 7shifts is I still remember I was actually talking to one of the founders of Skip The Dishes, Josh Samar, and I was asking his advice on what we should do for raising, like for raising money and, and doing these things and that everyone else was doing. And, um, He just said, let's take a step back. What type of company are you trying to build? And no one had ever asked me that before. And I thought it was a really important question. The one that I ask founders to this day, should I pursue this path? Should I pursue that? Like everyone sort of feels like I have to raise money to build a company. And that's not true. The difference between like, oh, I want to build a million dollar company or a $10 million company or a $100 million or a billion dollar company. Like those are different. Those are just different perspectives. mindsets and effort and all of these things. And I think that, yeah, I think that that's an important thing when people start thinking through what they want to build. Because you might think like, I want to build a massive company. To you, a massive company might be like a $10 million a year company. Well, for the investor that's writing you a check, They need you to be a $100 million company. And I think just getting those incentives aligned, even if you do pursue that road, is important. But I think also being true to yourself of what you think you want to do. What excites you? What actually gets you really, really jazzed? And for me, it was. Just be able to be everywhere. Like I wanted our products to be in the hands of every operator since the beginning. And I still have this kind of unwavering feeling for that. So it was, it was a reaffirming thought for me of what I wanted to do, but I thought it was a really good question.

Pablo Srugo (00:10:35):
How did you think about taking the leap from working and doing this kind of work at night and going all in on 7shifts? Where were you at that stage? Where was the company at? And how did you think that through?

Jordan Boesch (00:10:47):
This is always a fun side project for me. And I figured one day maybe they'll make enough money where I can do it full time. And it was, you know, excited. I was excited to at that opportunity. And I just remember going like when I was in Ottawa on the weekends, I would go door to door with it's funny. I didn't even have I didn't have a laptop at the time. So I printed off screenshots of 7shifts on paper. And I would go to door to door. I went to like Earl's and the keg and I was getting the I.T. guy and I was like, check this out. I like flip the page. I'd be like, check out this experience. Wouldn't this be great? And I'd like go to page three. And like I closed like zero deals. But, you know, I think that I always wanted, again, to just like have this used by everyone that was running a restaurant and an operation. Yeah. And so I think making the leap to sort of go full time and really go in it sort of happened pretty organically, which was, okay, 7shifts is now making $35,000 a year. Well, I could live off $35,000 a year. Like I can't anymore because I got a family and kids. But back then, you know, it was like, oh, totally doable. You know, I have a girlfriend at the time, like Dre and I were dating. She had a great career. Mine was like peanuts compared to her great career that was paying very well for where we were at. And I was like, well, I can go full time. So I went full time for about three months, rented an office with another buddy who was doing his kind of consulting stuff. And I was like, man, this is boring. I need to be working with a team. I need to - I love collaborating and solving problems and thinking through things. And so that's really when I was like, well, where do people build big companies? Oh, the Bay Area. Let's move to the Bay Area and let's see if we can get into a tech accelerator there. And so we applied to one. We did our interview with my co-founders, Dre and Johannes, who still work at the company.

Pablo Srugo (00:12:46):
So, that's when your girlfriend joined you as a co-founder, like during that time?

Jordan Boesch (00:12:49):
Yeah, yeah. We were like, okay, well, if the three of us, like, are we going to do this? And then they quit, we got in. So then I remember closing the laptop after the interview. Where they said, "You're in." And then we like closed, and then literally, they were both like, "Well, I guess I'll go resign tomorrow." They had to, and so we packed our bags and we moved to the Bay Area for a little bit.

Pablo Srugo (00:13:06):
Which accelerator did you get into?

Jordan Boesch (00:13:07):
It's called Boost. They were like a Bitcoin. They were just kind of coming off, of a few cohorts of like a Bitcoin accelerator program, and then they opened it up to any type. This was 2013.

Pablo Srugo (00:13:18):
Okay. And how long have you been running 7shifts as a standalone product?

Jordan Boesch (00:13:23):
It's hard to say when it happened because it was always just like, it was happening for years before that, where it was like a thing. But it was never really like when we registered it as like a corporation in 2013 because we had to. It was always just kind of like this thing that made some money for me.

Pablo Srugo (00:13:39):
You had what, like 10 or 20 customers sort of thing?

Jordan Boesch (00:13:41):
We're seeing at the time like we probably had, let's see, yeah, I would guess we had a couple of hundred, maybe a couple of thousand customers, nothing crazy. All organic.

Pablo Srugo (00:13:55):
I mean, it's not nothing. Product growth to 2,000 customers on the side is actually pretty impressive.

Jordan Boesch (00:14:01):
Yeah, maybe it was a couple hundred. It's hard to remember exactly, and our pricing was different, but yeah, it was great. And I think going through that accelerator taught us something, and I think it's really important for a bunch of co-founders is to feel a lot of friction between each other to get to the root of problems. We had some really good friction early on, and we talked it through, and it was like we were kind of stepping on each other's toes with certain work, and it's like, you're doing that well I want to be doing that and then you know you talk it through and then you're like okay move on but i think that taught us a lot about just being like very raw and candid with each other because we just wanted to get shit done and make it work. And it also prompted and brought in some good questions of like, what do we want to do when we grow up? Or what does it, we want this company to be when it grows up? Because we, we hadn't really defined it a whole lot. We sort of focused on every segment, like retail, healthcare, hospitality. We had all these segments and sort of said, well, let's just focus on hospitality. It's where we started. And I remember like, I think a lot of folks were like, well, why are you going to target a segment that can't afford to pay anything? Like margins are so slim, you know, their restaurants are super cheap. Like why would you target that segment? And I don't know, I sort of always felt like no one's targeting them because of all these reasons. What a great opportunity. So yeah, we, we, we decided to build for them. And I remember even when we were in San Mateo, um, living there, like we do door to door demos with people and like that's something I think is really cool about the Bay Area is, like, everyone seemed very open to, like, testing things in a way that I'd never seen before. Like, you'd walk into a restaurant, like, I'm building this app. I'm like, can I show it to you? And they'd be like, yeah, sure, let's check it out.

Pablo Srugo (00:15:41):
Very different than the Ottawa days.

Jordan Boesch (00:15:43):
Very different. Like, I think there was just more openness. You know, I think we got a few deals that way, but it was more so. It was more just like getting validation on some of the stuff that we were doing than anything. But door-to-door never really worked for us.

Pablo Srugo (00:15:58):
And what was like, you know, like that V1 or whatever of the product, it wasn't really V1, but that early version, 2013. Once you decide to go after hospitality, like what does the product do at that point?

Jordan Boesch (00:16:09):
Oh, you can just build a schedule with it. Employees can check the schedule in their app, post availability. Yeah. Maybe, we had a wall that you could like communicate on. It was just a global wall. There wasn't like messaging between people. It was the whole company saw everything when you were messaging.

Pablo Srugo (00:16:25):
And what was the competitive landscape at that point? Were there others, or it was really just like moving from like paper to this?

Jordan Boesch (00:16:30):
There's still 60% of people coming from paper and Excel still, but there was more. Yeah, it's like 80% of people were on paper and it was pretty crazy. It's like only the sophisticated restaurants had tooling, but all the folks that were the independents, which is like 70% of the market kind of felt like we're left out to dry. They didn't really have anything.

Pablo Srugo (00:16:51):
And so, you know, you mentioned, door-to-door didn't work. What was it that started working for you guys in those early days in terms of, like, distribution?

Jordan Boesch (00:17:01):
We focused a lot on SEO because I was doing marketing, sales, engineering server work and design work. We all sort of wore many hats. We saw an opportunity; there was no one talking about restaurant scheduling software. So, we just basically, one of those keywords. We built everything around restaurant scheduling software, and like everywhere. So, that drove a lot of early traffic for us, and then. 

Pablo Srugo (00:17:24):
Was it like a content play? Like you guys were blogging around this stuff, or was it just more like website optimization?

Jordan Boesch (00:17:30):
Both. We sorted it both. But obviously like didn't have all the tools we have today. Like it was a lot of grunt work. No chatGPT to help us on that. But we... Yeah, we... I remember Dre like cold called a customer and... They were on a competitor of ours and like, we moved them off that competitor on our system. And they were like a, like a 20 location juice chain in New York. They were moving all this stuff over to us. And, you know, they were sort of like, by the way, like you guys have time clocking. Right. And we're like, uh, yeah, totally. We like hung up and then we're like, we guys, we got to build time clocking like yesterday. And so Johannes and I, um, other co-founder, we just, uh, you know, we, we, we worked late, like building time clocking, time and attendance. And anyway, we built it in like record timing. And then, yeah, we were like, okay, we got this. And then we launched it to them. And the next, I think it was like the next, next day after we launched it, it was like, we got a, we got a bug to fix and we got fixed, fix that bug, relaunch it. And I'm like, You know, it was just this nonstop problem, series of problems with it. And like the next week, it's like, they're on Eastern time, we're on Pacific time. So the difference is three hours and they're waking up at their store. They're opening their store at 7 a.m. So they're calling us at 4 a.m. Pacific time with issues. And it's like, I would like, I remember like, picking up my phone at 4am, getting an earful of like swearing at me and just like getting beat down and then be like, okay, we'll get that fixed and like hang up and then go knock on Joey's door. Cause we were sort of in like this dorm setting and be like, Hey, we got to go fix this. And he's like, oh, okay. And so we fixed it. There's a bunch of that, but you know, time and attendance is used by like a large, a large bunch of customers today in 7shifts. And like, you know, we wouldn't have had it had we not built that. And I think like, yeah, you can't be scared of fucking up, you know, like we, we screwed up a bunch of stuff while we were building this, but we learned a lot. It wasn't the end of the world, but we. You know, we did lose them as a customer like a few years later to one of like the massive payroll companies that are like multi-billion dollar companies. And so I didn't feel too bad. I'm like, yeah, we can't compete at that scale. Again, it's more about the outcome of what we have today because of that work that we put in early on in those days.

Pablo Srugo (00:19:42):
Well, part of it is, you know, obviously getting yelled at by a customer is not good, but it's not that bad in the sense that at least it means you're important to them. What you really don't want in those early days is, unless customers just absolutely love your product and have no complaints, which is probably impossible. What you don't want is indifference. Somebody that's really pissed off means, at least you're solving a problem that they actually care about enough that the fact that it's not working is like preventing them from doing something, which, as a builder, is an opportunity. Because frankly, if you fix that problem, then you'll be able to provide that value. But if they are not calling you and they're not complaining, then they're probably not using the thing, not relying on it. You're like, at best, a nice to have.

Jordan Boesch (00:20:23):
Yeah, exactly.

Pablo Srugo (00:20:24):
And so how, like walk me through kind of the ramp. Was this like a slow burn, maybe even the fundraising history too, Was it a slow burn or was there like kind of insane growth? What did those early years look like?

Jordan Boesch (00:20:37):
Yeah, it was sort of slow burn initially. And I think when we got into the program, into Boost, that's where we started to see, really crazy numbers. We were like 4X'ing our revenue year over year, like we were growing quickly because we signed like some bigger, a few bigger locations.

Pablo Srugo (00:20:54):
But it's small, like you went from like $30 to like whatever, $120, $150K ARR, this sort of thing.

Jordan Boesch (00:21:00):
Exactly, I think, like, in doing pitches and pitching investors at demo day was really invigorating. I still, I still love doing that. I think it's a lot of fun and, talking about the vision and talking about what we've done and showing the traction that we've got. But that was, yeah, that's when we sort of raised our first little bit of angel money. We raised about $150K US, which was like, I don't know, $200K and some Canadian at the time. So it was like, great. So we moved back to Canada, kept building, managed to. 

Pablo Srugo (00:21:30):
Was that a small, I mean, even back then that, was still small. Today it's obviously a really small round because the median pre-seed is like a million, but things have changed. Back then, was that median, or was that small relative to whatever was happening in 2013?

Jordan Boesch (00:21:38):
I think it was like probably median, like- The $200K between the three of us, like, like we weren't paying ourselves really at that point. Like, yeah, like 35K, like, you know, they were like, my co-founders were like, yeah, I got like a couple months to all my savings that we'll like figure this out for. And if we can't, like, I'll go back to my job. So like getting $200K was like, holy, holy shit. We can pay ourselves $50K each and like have some stability for a year. And maybe we can even hire someone like another junior person. Yeah. And so that's what we did. We like went at it for, you know, a year or a few years. And before we, and because we focused on restaurants, we managed to attract and work with a bunch of, you know, restaurant partners, right? So Point of Sale was a big thing and Toast Point of Sale was just taking off. Touch Bistro was taking off, you know, Revel, all these other folks were like Cloud Point of Sale was starting to become a thing. And because we focused on restaurants and we had sort of these visions around integrating with point of sale, with the labor side, bringing in sales data so that we could forecast their sales more accurately and give folks this really holistic view on the scheduling page, that we actually built really great integrations with these folks early on. We were their first labor partner. And so we sort of wrote the playbook on doing these integrations. And then when these folks raised money and they grew, we were growing with them. And so integrations were a big part of how we grew as well. And they continue to be incredibly important to this day.

Pablo Srugo (00:23:16):
Were those part, like they were, would they push you and they'd get a cut or what was like the arrangement, especially in the early days with some of these like Toast or whoever else you were integrating with the OS side?

Jordan Boesch (00:23:26):
Yeah, we have revenue shares with a bunch of these companies, but I think in the early days it was more. Let's just integrate so we can add mutual value to these customers. We want, I mean, we're like 20% of a, you know, $80 a month product. Like nobody's getting rich here. Especially some of these larger payments players and point of sale players. But it was more about how can we really create compelling value? Products that are very valuable for these mutual customers such that they remain loyal customers long term and yeah that's kind of where.

Pablo Srugo (00:24:15):
Because, tell me a bit about, just think about partnership like partnerships. Are you now curious, to get go deeper on this because partnerships are very alluring, almost always like I hear about early stage founders working on partnerships, all the time. The upside is always similar, it's something around like distribution. Here's a partner that has a lot more distribution than me. If I get access to all their customers, imagine the opportunity. Great. The reality is most of these, like even if they get closed and signed, like they tend to fall flat. For one reason or another, usually the bigger partner just doesn't do nearly as much as the smaller partner. Things that they might have done for them because they got a million other things they could do. Like in your case, this partnership strategy, like you said, worked. I'm curious, what do you attribute that to? What went right? And maybe you have broader thoughts just on partnerships in general, whether it's structure or just something around them that makes them work versus not work. 

Jordan Boesch (00:24:59):
Well I think like being able to co-market and figure out what the go-to markets look like between the companies is an important aspect yes you're right like you need you need sort of support on the other end of the side too it's not just like integrated and they will come um yeah you need support on their end to co-market and um You know, have the reps talking about it. And how do you incentivize the reps to talk about it? What are you spiffing them? Are you spiffing them? Are you part of their marketplace where companies, their customers are sort of exploring and clicking on? And there's some exploratory stuff that happened there too. So yeah, I would say like building the right incentive structures, but also aligning the teams, like sharing a Slack channel. And I think that that's like a very underrated thing that folks should do in partnerships like just throw up a slack channel and like get the key people in there because like you want to solve things in real time and you want to like share things like wins in real time and you know give kudos and you sort of want to build some momentum around what's working and it sort of makes people feel good and it also like propels the partnership further so and we just invested a lot. Like we were very present at a lot of the partner events. So when they would do something with their sales reps, maybe we would sponsor it. Maybe we would go out and we would, we were just so active. Like if we look, if you look around at our competitors in the space, like they all were like, oh my god, 7shifts is everywhere with partners. Well, that was the strategy. That was part of it. being really close and lockstep with them. Like they were an extension of us and they were, we were extension of them. Like that's how we wanted partner. We, that's how we wanted partnerships to feel.

Pablo Srugo (00:26:45):
By the way, on another topic, I mean, you were in the Bay Area, you went through an accelerator, and then you came, you left, right? You came back to Canada. Why did you decide not to stay there and build there? Especially in those days, like these days, remote, blah, blah, blah. But that was less of a thing back then. I think the Bay had even more of a pull than it does, you know, even today. And today it has a lot. So how did you think through that?

Jordan Boesch (00:27:08):
I'm in Saskatchewan. We moved back to Saskatchewan, all of myself and my co-founders and home. This is where home is for us. Where our families are here, our friends are here. We had, we had the opportunity to stay there, but something about building something in a place where no one thought possible, where you could manage to attract some talent and hardworking individuals, that the only knock against them is that they haven't done it before and, be able to work with them on showing their Seeing them learn and be a part of something that could be really big and impactful was just like incredibly exciting to me and still is.

Pablo Srugo (00:27:46):
Like, what do you say? I mean, you know, just to play devil's advocate, what people would say is, especially back then, is like, listen, you want the best talent. If you want to be in every single restaurant in the world, you need the best talent. The best talent for the most part is in the Bay Area, certainly not in Saskatchewan. You know what I mean? What was your thinking or what is your answer to that? How do you think about that?


Jordan Boesch (00:28:06):
Yeah, I think like... Look, we still have folks that live in... Like executives that live in Atlanta or folks that live in Toronto. So look, I think there is great talent everywhere. I think that... what people underestimate is I think the, the grit that people have here in the prairies, like a bunch of folks here, like, you know, their parents, like, you know, maybe they grew up on a farm, maybe their parents grew up on a farm. Like, you know, they had to just like roll up their sleeves and get shit done. And I just, I think a large part of that mentality is like, there's not a whole lot of entitlement here. And I think that that's why a big part of me wanted to build a company here is like you had to earn your stars. Like you don't get things handed to you. You didn't grow up in, like, some, like, rich household where you went to some, like, prestigious school. You know, you sort of, like, just went to public school. We don't have private schools here in Saskatchewan. We still don't have private schools. So, like, there is this gritty, hardworking farm mentality, farmer mentality, I'll say that, that is, like, really... exciting and I think a lot of these folks can outwork so many people so like maybe on a relative like on a scale of like hey this person hasn't done it before it's like I would rather take the person that hasn't done it that's 10 times hungrier than the person that's done it maybe it's sort of like not as hungry. Like there, it depends on what stage you're looking for and what type of role for sure. But I think in the early stages you sort of want like, like missionaries that like just want to get it done and they'll do anything to get it done. And I think that's, those are the people that were people that worked out at 7shifts early days. They didn't care what their, their title was. They just wanted to get the job done.

Pablo Srugo (00:29:50):
How many people are you today?

Jordan Boesch (00:29:52):
About 250.

Pablo Srugo (00:29:53):
And fully remote or hybrid was the structure?

Jordan Boesch (00:29:56):
So we're currently mostly remote. I'm in the office right now. There are folks that come in. And in our hub here in Saskatoon. We have a hub in Toronto as well. We do Thursday lunches. So folks, you get like 40 people in each office come in. That's kind of how we have it set up right now, and there's folks all over, Canada that work with us as well on a remote basis.

Pablo Srugo (00:30:20):
And then back to the storyline. So you'd raised $200K. Where does that get you? Do you try and get to profitability, or are you just aiming for the next round? What's the setup?

Jordan Boesch (00:30:29):
Yeah, I think right now, we have a really great trajectory to, get to profitability in a like relatively short timeframe.


Pablo Srugo (00:30:38):
When you raised that $200,000 round, what's your goal with that? Are you trying to cross certain revenue milestone? Are you trying to get to profitability, or do you raise another round? What was kind of the setup back then?

Jordan Boesch (00:30:49):
Just grow as fast as we could and get as many operators on the platform as fast as possible, and seeing success. We raised our seed around with Relay Ventures who's based in Toronto. It's probably in 2016. We sort of joke, it was an intro from the folks at Touch Bistro, another restaurant point of sale company. I joke with our board member now that, the only way it feels like. The only reason he invested in us is like, yes, we had strong numbers and we continue to show strong numbers. But he just talks about how I would relentlessly fly to Toronto and keep them updated on our metrics. And I did. I flew to Toronto like all the time, and I'd be like, "Hey, here's how much we grew this year, or this month and this quarter."

Pablo Srugo (00:31:41):
How many times you do that?

Jordan Boesch (00:31:43):
I don't know. Like a lot throughout the year. And yeah, we joke that it's like. I invested in you out of just sheer exhaustion, Jordan, is like what I've heard.

Pablo Srugo (00:31:52):
You wore me out.

Jordan Boesch (00:31:54):
You wore me out, and the numbers were good, so we invested.

Pablo Srugo (00:31:57):
What were the numbers back then?

Jordan Boesch (00:31:58):
Man, I don't know. Maybe we were like half a million dollars in ARR or something. Maybe it was a couple $100K. I can't, I can't remember exactly, but.

Pablo Srugo (00:32:06):
And how much did you raise?

Jordan Boesch (00:32:07):
We'd raised a million dollars. Yeah, which was a big deal for us. Then we got to hire our first, we hired our first person that had a family. God, that was scary. It's like, oh, if it doesn't work, not only is he out of work, you know, now it's like his wife and kids. Anyway, that was a big moment for us where we got to hire our first family person. We had to grow up really fast. We had to build a real company and, show real value and just hunker down and do it.

Pablo Srugo (00:32:36):
And what was like, again, like as you keep as you go through, like walk me maybe to the zero to like five, zero to 10 million path. Was it kind of a doubling story? Because I mean, these days, what's the context? You know, these days you're hearing about these like zero to 100 million in like 12 months, zero to 100 million in nine months, like just insane stuff. I was trying to go faster and faster. A lot of the big successes, you know, I mean, some of them were like that, but many were not. I mean, even like Shopify, which is $100 billion company today, is mainly a doubling story. They just never stopped doubling for like a long, long time. So, here's what like your ramp looked like, you know, after that, like half a million. I mean, it doesn't matter too much to a million, but like when did you hit a million and what did things look like afterward?

Jordan Boesch (00:33:17):
Yeah. I think like trying to remember like what happened after we hit a million dollars ARR, we obviously, you know, we, we celebrated, actually, I remember us celebrating like 500 customers. Like we had like a cake, like ice cream cake that we had and had 500 on it. And I think we did the same thing with like a million dollars. Yeah. I think we, we just, we still hunkered down and like made the product better, hired, hired more people, um, probably switched. I think we switched offices to like a bigger space where we could continue to build, but yeah, like we were still focused on restaurants. So we were, we're still hunkering down there. Um, you know, we, we also like changed a bunch of like really complex, like some architecture stuff in the early days and, you know, to tell another, you know, screw up story here. Like we, we had to migrate like a structure and we wrote like a, this big script to do it. And we hit go on the script and we knew the script would like take an hour to run. And one of our engineers, early engineers accidentally hit the space bar, which stops the script. And it stopped at like midway through. And it was like, oh, my God, what does that mean? And it was like, oh, my God, we don't know where it ends. We just migrated like what half of our customer base. Like, how do we start for the we just like we were like, oh, my God. And so like the phone was ringing off the hook, like support was just swamped. Like we had like one support guy, like the rest of us were taking calls and we could. But I remember us like sleeping at the office. We had like Netflix on the TV. Like we were like taking turns, you know, like looking to see if the script was done and rewriting a bunch of stuff and cleaning up a bunch of things. And I remember getting driven home at like five in the morning. I like put my head down and then my phone would ring at six in the morning and I'd be like, I got to go back to work. And so I'd go back to the office and like, anyway, it was just like, There's, there's a few moments like that building seven chefs where it's just like, it was sleepless for like a period of time. And it was like having a kid.

Pablo Srugo (00:35:10):
And so now you're in like 50,000 restaurants revenue-wise, where you're like getting close to a hundred or like in that 50-ish range 

Jordan Boesch (00:35:18):
We're tens of millions in revenue. We're not, we're not at a hundred million, but we've got 50,000 customers on the platform. We're used by about 1 in 10 restaurant workers in the US right now. So, yeah, it's been a really crazy journey, fun ride. And yeah, still, still lots more to do.

Pablo Srugo (00:35:38):
Perfect. Well, listen, Jordan, we'll stop it there, but let me ask the last few questions we always end on. First one is like, and actually curious on this one for you, what did you feel? You had like true product market fit?

Jordan Boesch (00:35:49):
I never really felt that. I don't know. I just never really felt that.

Pablo Srugo (00:35:53):
You still don't?

Jordan Boesch (00:35:54):
It was so gradual. I do now, but like it was so gradual throughout so many years. So, you know, if I were to almost think back and where would I almost pinpoint that it would probably be like when we built a few restaurant specific features and had the restaurant point of sale integrations wired up. We were like communicating with the executives at some of these point of sale companies about the integration and how things are going. I started to feel okay, we found our footing in that this is the space we're going to go after and we've added value for these customers in a way that no one else has done today. So I would say that was that was a big moment for us.

Pablo Srugo (00:36:32):
Was there a moment in particular, where you thought that things wouldn't work out? When you actually thought you might fail?

Jordan Boesch (00:36:40):
Oh, yeah. Yeah. A few times. You know, you're like you're sort of burning cash, right? Early days, you've got to hired a bunch of people, it's probably in 2017/2018. Yeah. I remember having like anxiety and I was like, what is this feeling? I feel like emptiness and sadness. I'm like, Oh, that's like what people feel with like depression. Like I had never felt that before, but it was just a weird, darkness, I would say. It was cause we were you know, a small amount of runway left.

Pablo Srugo (00:37:13):
And I was just like, "What's the lowest that you had? You remember?"

Jordan Boesch (00:37:16):
I think at that time it was like, we had four months of runway left or something.

Pablo Srugo (00:37:20):
Oh God.

Jordan Boesch (00:37:20):
Yeah.

Pablo Srugo (00:37:21):
That's scary.

Jordan Boesch (00:37:22):
And I'm like, this is not fun.

Pablo Srugo (00:37:24):
How did you solve it? You just raised around or did you have to do like layoffs?

Jordan Boesch (00:37:28):
No, we raised money. We did it and I just hustled like crazy to do it. And, yeah. I guess that's what you do.

Pablo Srugo (00:37:37):
That's part of the start of life. Then the last question is, what's like, I mean, you speak, I'm sure a lot of founders, What's one piece of advice you find yourself giving out like most, you know, commonly?

Jordan Boesch (00:37:48):
I think that finding out what type of company people want to build is a really important one. I also think going through this exercise that we went through with core values and like we went through it a few times and reshaping it. The article is called like draw the owl. I think Jeff Lawson from Twilio CEO wrote this article on how they did their core values at Twilio and the exercise that they went through. I think that's really important, especially early on as you're trying to hire people because you don't want to like, let people go and just say like. Oh, like they sucked. Like you, you kind of know it and maybe other people know it too, but that's still not a great reason. And look, I've made those calls before and it's like, they weren't the wrong, they weren't the wrong reasons. But it could have been so much more clear if I could say like, these are our values. This person didn't align with these values and everyone could go, yeah, you're right. And then like, you know, move on. And no one's kind of like scared about their job, like they're next. So I think that establishing good behavioral based core values was a, was a really good turning point for us because it allowed everyone else to sort of, you know, almost like, see the value mismatch before we saw, like, or before I saw. And you sort of want that. You want a strong culture to either attract or repel. And to continue to attract, you have to have the people that are demonstrating the behaviors. And I love the quote by Danny Meyer, one of my personal idols, and he's an investor in 7shifts. He's the founder of Shake Shack and Union Square Hospitality Group. You know, culture is the sum of all the behaviors you celebrate minus the ones you tolerate. And as my engineer brain spins on that, I just find it makes so much sense. It just makes a lot of sense. It's like a calculation. Because you always tolerate some amount of behaviors that are shitty. No one's perfect. No manager is perfect. But it's like the output of the behaviors you champion minus the ones you tolerate is your culture. And so get the behaviors right and what you want to see out of people.

Pablo Srugo (00:39:57):
Well, Jordan, thanks so much for spending time and it's been great.

Jordan Boesch (00:40:00):
Thank you for having me.

Pablo Srugo (00:40:03):
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