How a major mistake almost cost Ryan Fyfe his company

How do you recover from a huge mistake that has the potential of sinking your company?

Ryan Fyfe is the Founder of Humanity, which is an easy-to-use online employee scheduling and workforce management software.

Ryan Fyfe was about to close a big funding round for Humanity when he discovered unethical practices that were going on that affected the company’s sales metrics.

Ryan Fyfe

Ryan Fyfe


Ryan Fyfe is the Founder of Humanity, which is an easy-to-use online employee scheduling and workforce management software.


Full Interview Transcript

Andrew: Hey there, freedom fighters. You know me, my name is Andrew Warner. I’m the founder of Mixergy where I interview entrepreneurs about how they built their businesses. Recently, I was in Santiago, Chile, where I flew to run a marathon, 26.2 miles. Ryan, a lot of people consider like three-mile runs a marathon. A marathon actually has to be 26.2 miles. So, I did it. And I also flew there to interview entrepreneurs.

And in between, you know, first day was interview, last day was run the marathon. In between, I thought, I’m just going to live in a new city for a week and work out of a new city and man, was I distracted? The internet wasn’t exactly doing what I wanted to do. And for some reason, I didn’t go to a Regus office, I wanted, I guess, to experience day-to-day life there. It didn’t do it. I got distracted by all the interesting sites, by all the interesting people, by the fact that I want to practice my Spanish. I got very little work done.

Joining me today, though, is an entrepreneur from Panama right now, where he started his company, and somehow he wasn’t distracted by all that or maybe he was we’ll find out. Whether he was or wasn’t, I know this for sure, that guy was able to get some serious work done. And the thing that he worked on, was the creation of Humanity. Joining me is the founder of Humanity. His name is Ryan Fyfe, I can’t stop. I love saying it that way, Ryan. The name of this company is Humanity.

I don’t know why, it’s a goofy approach. It’s like, I’m sure you’ve heard a million times. I still can’t get over. The name of the company is Humanity. He is the founder of Humanity. It is enterprise employee scheduling software. You know how you’ve got to schedule employees and in the past used to be this big piece of paper that was on a wall somewhere and people would have to go and write their names and fill in them. He said, “You know what, enough of that. I’m going to do this all in the cloud.”

And he did it and it did great. And then, I don’t know what happened. He left. He said, “That’s it.” And he moved on to create something called WorkChain. It’s real-time payroll using blockchain and cryptocurrency which Ryan, like a year ago, everybody would have been in love with you. Crypto, blockchain, the whole thing. And now, I wonder how people are treating you now that both of those blockchain, cryptocurrency, both of those terms are out of favor.

We’re going to find out about all that, thanks to two phenomenal sponsors. The first will do your email marketing so well, mm-hmm. It is the best of the best ActiveCampaign. And the second, if you want to hire developers and Ryan, you’re going to want to know about them. You got to know about Toptal. I’ll tell everybody about those later. Ryan, good to see you here.

Ryan: Thank you so much for having me on the show.

Andrew: Ryan, what’s your revenue at Humanity? I know you’re not there day-to-day, but when you left, let’s say, what was the revenue?

Ryan: Yeah, sure. What I can disclose publicly is that the company is over 10 million in revenue. It’s a profitable company today. Like you mentioned, I stepped down from the team about a year ago.

Andrew: Is it wrong to then look over your shoulder and say, “Oh, are living in the hostel?” I’m seeing bunk beds with no sheets and tell me?

Ryan: Yeah, yeah, sorry. I’m right now in the middle of moving. So I’m going to be moving back from Panama to Canada, and so my apartment is a complete mess. And this is my daughter’s room and it was sort of like the only place I could find that, it still looks somewhat presentable.

Andrew: Okay.

Ryan: Yeah. So, after 10 years in here in Panama, I’m going to be heading back to Canada for a while.

Andrew: Why?

Ryan: The biggest reason I stayed in Panama was for my daughter. I’ve got an eight-year-old, and she’s actually going to be heading up to North America as well, studying and so for me to be closer to her, it’s going to be Canada and the U.S. actually for the law.

Andrew: So you got to Panama, you had a child and you said, “I’m going to stay here and make sure that the child . . . my daughter gets the culture and education that she was born into.”

Ryan: Yeah. It’s pretty insane to think about because for, you know, the first few years of her life, I had half custody of her and so I was, you know, spending three-and-a-half days a week with her and it was literally at the same time when the company was, you know, growing very quickly in those early years. We made the decision to go ahead and, you know, do the traditional, like Delaware Silicon Valley company. And so I would get on a plane every Sunday night, I would show up in San Francisco, Monday through Wednesday, fly home overnight and then spend sort of that long weekend with my daughter just kind of complete insanity week after week.

Andrew: And you could totally be with her because I find the kids know when you’re not fully focused and the stress level when you got to pay attention to a kid and the voice in your head that says, “You need to finish this one project is insane.”

Ryan: Yeah. So I could and I don’t know if I just got incredibly blessed or if she knew like with the lucky baby that could focus or let me focus or whether she also knew that there was something different about the situation and I can just point to situations where I’m on like a make or break demo with who’s going to become our next biggest customer. I’m still like kind of, the one like, that they had the lead sales rep. And my daughter would sit in a play-crib for literally an hour next to me while I’m pitching the demo and not cry or say a word. Just look at me happily, like, I’ve never seen another kid do that. It’s just incredible, you know.

Andrew: That is shocking. Were you married to her mom? Is it too personal to ask you that?

Ryan: No, it’s not. I wasn’t. We were separated, so.

Andrew: Okay.

Ryan: It’s been a bumpy, but an interesting road. Luckily things have been getting a lot better as my daughter’s getting older. And so now we’re going to . . . Now, finally, when I’m no longer working in the U.S. Now I have the opportunity to get there. So it’s a little bit a lot backwards.

Andrew: What were you doing in Panama City?

Ryan: Yeah. So I first before starting ShiftPlanning, I was doing contract web developments and more kind of traditional SEO doing like made for AdSense websites. So I built a huge network of content websites and then putting up ad space on them. And so I was looking for a place . . . I was just out of high school, I was looking for a place that had, you know, low cost of living, good tax situation, the language I wanted to learn, beautiful girls that were down here. And so I traveled a lot to kind of figure out which countries in the world had all of those places. And Panama was really the only place that I found that sort of hit that sweet spot of, you know, a booming economy at the time. The first time I came here was 15 years ago. And to see the change in the countries here is kind of like seeing Dubai on a different scale, of course. But it’s just phenomenal how quickly this thing built up.

Andrew: You know, one of the nice things about traveling somewhere else is, you really are living the life that you want. You get to experience a new environment, you get to really feel every little thing. Like going out and getting coffee is a new experience. It feels alive to do it. But the other thing is, you got to be determined to get up and go. There are people in the U.S. when the economy is bad, who still don’t have the willingness to get up and go to a different city. You go to a whole other country, learn their culture, another language. I feel like that’s partially a sense of urgency and . . . A sense of, I don’t know, that you have to do something with your life. I wonder if that goes back to your childhood. I wonder if you can talk a little bit about the Teenage Ninja Turtles shirt that you had as a kid. I see the smile, you know what I’m talking about. What is that?

Ryan: I did. And I had the sweat pants and I think those were some kind of unique parts of our story because I grew up in Canada in northern Alberta, a very rich part of Canada, but we actually grew up not so wealthy in that area, both for different reasons of my family. We were kind of like, on the poor acreage, outside of like one of the richest communities in Alberta. And I think a lot of that really shaped who I was very early on.

You know, I was the youngest as well. And so I kind of always wanted to have a little bit more maybe than I would get for my age, or also just when I saw kids that were my age having and so it’s like, you know, if my brother got something, I wanted to have it. He’s two-and-a-half years older than I was. Our friends that, you know, their parents owned a video game store or something like that. They had all the latest games and we didn’t. So I think part of that sort of stuck with me a lot, or that absolutely impacted me.

And then, I think the other big thing like you mentioned around travel is, I think, yes, some people have a very strong sense of home and for me, I don’t really have that. And I think it comes from a few reasons. One of them is my family itself, is very, very separated where they live. And then we also moved a lot, you know, when we were growing up. So I was born in Ontario.

Andrew: Because?

Ryan: Mainly my dad’s job. Yeah. My dad was a professor at the University doing mechanical engineering. And so his job moved around a little bit.

Andrew: Because he did get different jobs as a professor at different universities?

Ryan: Well, this was actually what they were like, you know, still going through school. So he did his masters in Ontario. Then he did his postdoc in Belgium. So I spent the first few years of my life in Belgium. And then we had the opportunity to go on a sabbatical, which was an incredible experience when I was 12. I moved to New Zealand for a year. And so these types of things stuck with me. And then you mentioned you’re a runner, that’s fantastic. I was a competitive athlete all through kind of middle school and high school. So I got to compete with Canada. I got to go around to Europe and different places to run. And so all of that sort of gave me this nonstop travel bug where, yeah.

Andrew: What is the Teenage Mutant Ninja story?

Ryan: Oh, sorry, like the part with my brother, maybe that I mentioned or . . . ?

Andrew: With your clothes, yeah. I don’t want to tell your story. But there’s one that I’m kind of teeing up for you. And if it’s too confusing, I’ll just jump in and say it.

Ryan: Yeah. Maybe do jump in and say it because . . .

Andrew: Here’s what I heard about you. One day you showed up to school wearing Teenage Mutant Ninja Turtles sweats. What happened?

Ryan: They were from one of the other kids in my class or, you know, from my brother’s friends that were like having. And so we had a lot of, you know, second-hand clothes growing up, but I think that sort of became a part of our identity or maybe like I mentioned before, especially for my older brother. I was sort of old enough, I wasn’t older enough at the time where maybe the material things impacted me just yet. But I think there was sort of that loss of innocence or thinking through some of that stuff. And when I did get a little bit older than that’s what pushed me to work just I think incredibly hard because I wanted to have the things that my family couldn’t provide. And so, you know, my parents made me business cards when I was very young. I’ve worked in every, you know, different type of part-time job, you can imagine. And that’s actually where the idea for ShiftPlanning or Humanity came from.

Andrew: And before we get into that, I’m sorry to interrupt but the reason that the business cards were entering your life, the reason that this vision of entrepreneurship enter your life, seems to me, I guess it was your dad. He decided I’m not going to be in the university system anymore. I’m going to go and work for where? And then, he had this life-changing experience.

Ryan: Okay, Yep. Yep. So I got to see there’s sort of the I think the early age . . . I’ve thought a lot about this as well. These are fantastic and fun stuff to think about or reflect on. The other big thing that happened in my life is, that’s right. My dad after being a prof in the university system for about 10 years, he went and started a company with his brother, a technology company. And so I got to watch sort of the whole entrepreneurial journey, you know, happen through that and they exited that company in 2005. They sold it to Garmin, the big GPS company. So that was, you know, another sort of thing that happened of course, as I was growing up as well and I got to spend and see a lot of that.

Andrew: I hired a producer from a TV show to give me some coaching on interviews and when he looked at my transcript, he said, “Andrew, do not look for the Batman moment.” I go, “What the hell is that Batman moment?” He goes, “That’s where Batman’s parents die and as a result he . . . “Or was it whoever it is, who’s plays Batman, who is that? His alter ego?

Ryan: Bruce Wayne.

Andrew: Bruce Wayne, right? That’s where Bruce Wayne’s parents die. And then, as a result, he becomes Batman. You’d look for these one incidents, Andrew, that then change everything. I don’t want to do it with you, tell me if I am reading too much into it. But it feels to me like watching your dad go from a professor who was making not enough money for you to get your own clothes. You had to have to hand-me-downs, where I looked at my notes from our producer’s conversation with you, you felt excited walking in with the sweats and then when you found out it was a friends, it was a bit of a letdown.

So you go from that to suddenly a life-changing experience to your dad and you realize in your head, you know what this thing actually is available to me. This can change my life. I’m going to create big business cards with my mom and maybe play business today and someday have a business. Am I reading too much into it?

Ryan: I would say the, you know, idea of doing something on my own came from, well, before my dad’s actual startup, I think that would have helped sort of solidify or help me think about actually formalizing a startup versus doing something different. So it was definitely part of the same progression but the inner part of me and I can point back through things all through school, you know, why was I trying to graduate super young. I graduated . . .

Andrew: You would skip like, two years earlier or something?

Ryan: Yeah, I skipped two years, I graduated super young. I was working at, you know, sometimes I was closing down a kitchen until like 1:00 or 2:00 in the morning on nights when I’d have school the next day. Like, why was I doing all of these things even before my dad had that startup? And so I think . . . But you’re right. There was a couple of big key things that helped really make the company possible. One of them was absolutely watching my dad and that experience because it wasn’t just my dad, he started that company with my dad and my aunt and uncle. I worked there. I got to work there sometimes during the summer. And so I got a lot of experience through that for sure.

The other big thing that happened though is, I got connected with who is now, you know, a fantastic friend of mine and my business mentor. And it was a web project, like a web development project that I got into do. And as a part of that experience, he really took me under his wing, he brought me to all of his pitches, he helped me, you know, like, I’d have input on the business plan and all these types of things. And that was my kind of God like, a business degree essentially from him during that time. And then, he became one of our first board members in the early days of the forming of my own company. And so I think all of that helped groom me in a big way for this.

Andrew: So someone who goes out and creates quick websites to put AdSense on it, to make money from Google by SEO and Google, that’s someone who’s looking for fast money and is willing to just like create, let’s just say quickie sites, but not really good sites. What was your plan?

Ryan: Yeah, I agree. It was a lot of garbage content to be honest.

Andrew: I didn’t want to say it because I didn’t want to calm you off from the conversation.

Ryan: No, no. You can say for what it is. You know, made for AdSense and content stuff for SEO back in the day was a lot of that. But I think that the beauty of that is it taught me a lot about following, you know, Google and all this stuff, which became, you know, one of the primary reasons for Humanity to really accelerate in this early years. But what was the kind of moment that switched I think as search engine marketing was getting harder and harder, I had to, you know, teach myself more web development skills because you can’t manage five websites.

This was 15, 20 years ago. You can’t even manage that many blogs, there wasn’t a Blogger and all these services, right. And so I was building a program to run this network of over 500 content websites. And then, that business was doing incredibly well sort of around the time. Like when I was thinking about going down to Panama and things like that, but it also like as well, as it was doing, it also imploded pretty quickly overnight, as you know, Google’s algorithm changed pretty substantially and started to you know, really catch on to like, you know, all the types of, let’s call it gray hat stuff that was happening from that regard.

And so then I started thinking about what next to do. And I worked on a ton of projects that were all, you know, somewhat social media based, you know, this was sort of around the time when there was like, lots of different kind of niche social networks. And so I was playing around with ideas for you know, teenagers in Canada or people that really love to use that girl these types of things that would become sort of the next sexy, Hi5 or Myspace or whatever was big at the time, right?

But it was through watching. I think working with my business mentor a little bit thinking about how many eyeballs, the company I worked on with him is called Quantum Shift and it was a media platform for, you know, NGOs and bloggers and different things like that. And when I started, you know, we struck out with that business, unfortunately, just because, even if we were able to get the thing to, you know, 50,000, 100,000 monthly visits, it still just generates next to nothing in ad revenue.

And so that’s, I think was sort of like an eye-opener for me that, you know, maybe creating this next big like what I thought was going to be a next big sexy revenue generating thing, the revenue might not even be there. And then at about the same time, I started, you know, SaaS was very nascent, but I started thinking, oh, this is fantastic. There’s all these unsexy business problems that you got 100 customers and you’re all of a sudden making money and that for me sound . . . That was when the light bulb went off. I fell in love with SaaS and didn’t look back.

Andrew: What became Humanity? Was that your first SaaS project?

Ryan: It was. Yeah. It was founded as ShiftPlanning, And we rebranded about two-and-a-half years ago.

Andrew: I’m on the original version of ShiftPlanning it right now. It looks good. Essentially, it’s what it is right now, right?

Ryan: Yeah.

Andrew: The business didn’t . . . You knew from the beginning what it was going to be. It definitely is a better version of what it was but it’s still the same. There’s not an unrecognizable path from one to the other. Let me take a moment to talk about my first sponsor. And then, we’re going to jump right in and figure out how you knew even if this was necessary to create. My first sponsor is a company called ActiveCampaign. Ryan, do you know ActiveCampaign or am I about to introduce you to them?

Ryan: I don’t, you are.

Andrew: You do email marketing or you just like an SEO person usually?

Ryan: I don’t do as much email marketing, but I’ve used tools like Intercom and similar, so.

Andrew: Okay. Great. So I’ll open your eyes to this. So one of the things that you do right now at WorkChain is, you’ve got this product that allows people to get paid. I’m kind of tying in the ad to your story, allow people to get paid fast. The example that I saw on your website was, you going in clocking into work, and then showing your phone waiting, waiting, waiting. It didn’t happen like a second later, but I liked it. It didn’t happen a second later look more realistic. Less than a minute, within a few seconds later, you got paid and you showed us the transaction and all that happening.

Now, there are two groups of people who are interested in that. One is employers, they want to know, does this make sense or not? Another group of people who are employees, they want to know, do I want this? And if I do, how do I even get my boss to do this? Two different groups of people both watching that same video that I saw, but after that, they start to diverge. One of them might read a blog post, it says, “How do you tell your boss that you need to have this?” Does this make sense for you? How do you pay the bills when you get blockchained? Will my salary go up and down as Bitcoin prices go up and down? The other one has business- related questions, and they’re each reading different blog posts on the same website.

If you’re using ActiveCampaign and they sign up for your email newsletter, you can target them differently. So you don’t go into an employee and start saying, “You need to put this into your business. This has to go into your business right now.” And you alienate them. But instead, you recognize, “Hey, this is somebody who’s been looking at all my videos about how to tell your boss. This is somebody who’s been looking at all my blog posts about how to get paid this way.” We should be giving them some guides on how to talk to your boss about getting paid with cryptocurrency. How to integrate this in and how to get other employees excited about it.

Right. That’s the idea behind ActiveCampaign. Yes, people will join your email newsletter, your email marketing, just like every other software, but what they do is allow you to tag people based on what they’ve clicked on, what they told you about themselves, what they asked for and what they’ve done on your website. And of course, I call them an email marketing company, but they do way more than email. You want to do text messaging, yes. You want to do chatbot messaging, they do all that, so much more because what they’re about is smart, automated, intelligent marketing not necessarily just email.

All right, if you guys want to get started with it or, Ryan, if maybe on the airplane you say, “I don’t want to work anymore. I need a little bit of a break but I’m kind of curious intellectually.”

Here’s what you do, you go to When you go there, you’re going to see that they’ll let you try their software for free. Create a fake company, create a real company, experiment, see what you think about it and what you’re going find is, it’s way easier to do than you imagined. And if you decide to stick with them, the second month will be free. If you want help they give you two free one-on-one sessions with their people to make sure that it works. And if you’re already with a different email marketing company, if use my link they will migrate you for free. So here’s the link

All right, I’m grateful to them for sponsoring. I like that your company name is Humanity because unlike me, I always have to spell Mixergy because otherwise people type in mix energy and you don’t have to do that. Humanity, if you don’t know how to spell humanity, look it up. How did you know that this was a necessary product, that this was a problem worth solving?

Ryan: I think like I mentioned it comes back to sort of that side, I worked . . . I clean dishes, I washed cars, I worked in retail lots and kind of everything in between that, you know, fast food and, etc. And so I think it was that time that, you know, I felt the problems firsthand from an employee and especially as an athlete where, you know, I might have a track meet that comes up in a few weeks’ time, but I’ve already been scheduled. And it was literally the type of pain as an individual employee that you have to go in and I had to bike into work at that time. So I’m biking across town just to go into work to try to figure out you know, who can cover my shifts.

And, you know, some sometimes it gets so bad where you actually have to pay people to go through the list. Nobody wants to take it because it’s like Friday night, and maybe there’s a band in town or something like that so you end up paying people to cover your shifts or you end up taking two of their unattractive shifts in return like all of this type of stuff. And so I saw that firsthand, as an employee, you know, in contact with the manager.

And then I started thinking about how that experience can be translated to the web. And just how, you know, the traditionally schedule is a static artifact that sort of lives on the wall at the back of a business. How could that become collaborative? You know, what if business could know why availability changes in advance and not assume that for the entire school semester, for example, that it stays the same. What if I could book the time off that I need to in advance, and then the things sort of evolved from there?

But the initial spark definitely came from, you know, deeply understanding these businesses. And it was, again, this huge light bulb that went off the first time I started really thinking about kind of putting a business together about this, primarily just because it was like, I knew all of these different industries. And this is like a global problem like shift-based businesses is a huge part of the labor force. And I just couldn’t point to a single business that I’d worked at that used any sort of solution that was out there.

When I went online to you, know, see who’s in employee scheduling software, there was a few players, a couple of them were pretty big at the time. But I noticed two things, one is that they were kind of niche orientated, predominantly in food and beverage or in health care. And then the other thing that I noticed is that this was sort of I don’t, what it may be like, Web 1.0 or Web 2.0 or whatever. They sort of had these archaic products. There was nothing beautiful about them. There was nothing intuitive about them. Many of them didn’t have mobile apps yet. So there were still I felt like a huge gap in the marketplace in terms of even just like what the existing competitors were there and a wide-open marketplace with literally millions of small businesses and big businesses that could use this thing.

Andrew: And still you told our producer that first version was really crude. It was almost like a clone of Google Calendar and social site.

Ryan: That’s right. I think it was.

Andrew: What do you mean? So what could it do?

Ryan: It did very basic things especially at the beginning, and I think it absolutely was a clone. And I think a lot of the stuff that I did early on, I had no sense of kind of UI or UX design. So we would sort of go, you know, here’s a project management site that we liked and that became our design or Google Calendar was maybe a tool that people knew how to use.

Andrew: Was Basecamp an inspiration? It feels a little bit like there’s some in there.

Ryan: In the early website, no. But there’s another company called, is it? ActiveCollab, I believe, that was one of the ones that was actually from Serbia. And so Humanity has a Serbian office there. So my designer that I met had, you know, was always referencing to that one, so.

Andrew: Okay, so you’re just copying what they did? How long did it take you to build the first version?

Ryan: It took quite a while actually, because it was the first time building a pretty dynamic user app. And there was a lot of sort of nuances in it and none of the APIs that you have, you know, together now, you like quickly, send SMS and different things like that through Twilio. So I would say took four months to sort of build like the beta version of it and then another two to three months to get something ready that was, I would say like, commercially ready in terms of having the website the signup process and all the rest of that ready.

Andrew: Was this you creating it?

Ryan: It was. Yeah.

Andrew: Wow. And so that you had I kind of skipped over it but you had a site before that was kind of WordPress, kind of Myspace, kind of like or maybe like BuddyPress, where you allowed people to create their own social network/publishing site. It obviously didn’t go anywhere. It got crushed by Facebook and WordPress, etc. But it seems like that’s what helped you learn about software creation so that you could . . . you say, this is a long time for me six months doesn’t seem like that long to create a first version of the software.

Ryan: Yeah. So I did have a number of these different projects and even you know, client-base project sort of things. There was already a lot of open source stuff that you could use, but not nearly . . . it’s incredible what you can build now. I mean, you can do this in a fraction of that time today, just with all the services and open source stuff that’s available. But you’re right, I think, you know, the first version of ShiftPlanning, of that software would have been like a fourth of the code, from the social network site, and then building on top of these user profiles and surf it. It all evolves together for sure.

Andrew: Oh, that’s great. Okay, and then you went out to get customers and you got a grand total of zero?

Ryan: That’s right. Yeah. Went online, kind of blew the horn. And, you know, not a lot happened. I think it was sort of, again, the first time I was figuring out how to bring a SaaS business online. And so I did a number of things with them, that I did think ultimately set the company up for a fantastic success. So I started thinking outside of the box in terms of, you know, what are different ways we can get customers in and knowing that the product was a beta product, I decided to give it away for free.

Andrew: If I understand this right, at first you had a partner, and with a partner, what you were doing was, trying to get sales first. Who is this partner?

Ryan: Yeah. So he was initially going to be a co-founder, and so the kind of initial understanding that we had as he would take over all of the commercial sides of the business. And I thought that was great, you know, what I want to do is build product, I want to code, that was the part that I love to do. And so I was happy to let him take that over.

And what ended up happening is, I think, you know, for better or for worse, trying to sell SaaS offline, I think, never really scaled or worked. But this was, you know, 10 years ago, 11 years ago, trying to get companies to use a beta product of employee scheduling when most of them don’t have a computer in their office or different things like that, that are doing, you know, tablets, like point of sale based-tablets have all this stuff everywhere now. It’s like, why wouldn’t you have this but back then that wasn’t the case. And so we ended up going just looping in circles where every time you would go and meet a potential customer and he would come back with another list of, you know, 10 features that needed to be built, so that this one customer would try to use the product for free.

Andrew: Why do you think that would be? Why do you think that when he . . . because he would go into like the Olive Garden, he would go into places that had a lot of employees, a lot of time shifting problems, why do you think that instead of saying no, or yes, they would say, “How about if you had this feature? If you had that feature, it would be great”?

Ryan: I think it was too early. I think it was honestly too early in the market from most perspective, and it’s still like, it’s honestly ironic. Like, it’s 10 years later, we’ve built a great business around that’s solving this problem. Ten other people have built great businesses around solving this problem. It seems pretty obvious now that you should be doing this. It’s incredible, you know, the large enterprises or, you know, hospitals and things that we deal with every single day still that don’t really know the solutions exists. And so this was very much the case back then.

Thinking about it deeper in terms of like, maybe why would they come back with a, “No, we’re not ready.” Or maybe that is the answer where they’re kind of giving excuses because even when we could go back to them with the next set of things that they had asked for, they’d still weren’t ready yet. And so maybe that was whatever . . .

Andrew: Excuse. It felt right, but something felt wrong. And they didn’t know how to articulate that. “Look, we don’t have a way to implement this. It’s too intimidating.” That’s what it is.

Ryan: I think so. Yeah.

Andrew: And it’s amazing actually. Well, you tell me . . .

Ryan: The other thing that comes up and I think this is something I always say with, you know, doing, for example, like free trials and things like that, but you’re always trying to get to this like wow moment where an individual customer can see the value. And when you’re doing employee scheduling, it takes time to see the value in the process because you first have to implement the schedule you already have into the software, then you have to get all of your staff on-boarded. And it’s only when all of those pieces come together that for example, you see that two employees swap their shift or you know that on Friday night, everybody showed up on time because everybody was aware because they got their SMS reminder beforehand. These are all things that you have to actually, you know, do quite a bit before you start to feel that while the benefit of having invested in the tool.

Andrew: Right.

Ryan: And so I think we weren’t able at the time to demonstrate any of that benefit to them. And here we are asking them to change a key business process, and they’re all busy. You know, people that work in shift-based businesses, they work on the floor. So they’re extremely busy, they don’t really have the time to go sit down, you know, get off the floor, get out of the restaurant for a while to go ahead and set up their stuff. And that’s probably another big part of it. Just the friction was too big at that time.

Andrew: Ryan, as you were describing the problem. I wondered if you were and people in your shoes were experiencing the problem, but the person who would have to decide to implement new software wasn’t experiencing it. They weren’t writing back to the restaurant. They weren’t asking somebody to shift time with them. They weren’t then saying hey, “Can I pay you to take my shift so that I can go and I don’t know, do this other thing.” They didn’t experience it. So maybe if they didn’t experience the pain, they weren’t ready yet to buy the solution.

Ryan: Yup. I think that’s right, as well. And maybe if we had targeted back then, you know, thinking about this problem now, if we had targeted different types of businesses that might have worked, because if I think back to what, you know, some of the parallels were in our early customer profiles, they may be were, you know, owner-run businesses. So the owner directly ran the problem directly, you know, took on the credit card to solve the problem with which definitely helps, absolutely.

Andrew: So your partner, future co-founder, whatever the title was, just said, “You know what, this is not working for me.” He left, you said, “All right, I’m on my own now. I’m a marketer, I got to find a way to market my own thing.” And that’s when you said, “I’m going to take a radically different approach.” Which was?

Ryan: Yes. So the different approach was to basically rather than trying to do anything offline, do complete, like only online sales only. And I think the key thing that kind of helped us get some traction early on is I did a few things. One of them was offered away the product for free at the start. So that brought in, you know, early adopters, some of those customers and users are still with us 10 years later, which is really fantastic.

And then, the other thing I did is I focused really hard on, you know, the stuff that I’ve come from, which was internet marketing. And so we dominated the search engines, you know, for the first kind of three to five years of the business for every employee scheduling, workforce management, all of these related keywords. And these aren’t high volume terms. They’ve gotten bigger than they were 10 years ago, but it was to the point where you get this very high quality, relevant traffic and then I just focused on trying to build sort of a low touch marketing machine.

So very low touch sales, really focusing hard on the product and when you get that wheel moving, some pretty magical things happen because, you know, if you focus on your product and your customers, they give you fantastic reviews, word of mouth spreads, all of that type of stuff. All the types of things that are very slow to get moving early on were the things that we were invested in. And so I think that helped build a fantastic, you know, funnel for us very early on once that got moving.

And it was slow, like you mentioned. You know, for the first six months, there was no paying customers, because I was giving things away for free. But fast forward to sort of year two and year three of the business we were growing, you know, 100%, 200%, finally, 500% per year. And so things really, really got moving.

Andrew: I started looking at, like, I went to Google search results for and I limited it to your first year and then your second year, and what I noticed was the word bunch of review sites, some of which I think are out of business, others are like Inc. Magazine that would include you in a list. It feels like you guys were really good or you personally were really good at that. Am I right?

Ryan: Yeah. So again, I spent a lot of time on the review sites. And actually, if we talked about how review sites have changed the game now, it’s fundamentally changed where the review sites used to be a lot more about personal bloggers. And so I would go out, you know, build create a big list of everyone that was talking about anything to do with small business software, employee scheduling, all this stuff. And then, I would go pitch them to include me in their list. And so that worked very well.

I think that the way things are now though, while I was focusing on, you know, building organic rankings for our product, or like for our terms itself. Now, the way things have changed today is if you Google, for example, any category that we’re in, like employee scheduling software, six out of the top 10 spots, Google has reserved for the much larger review sites like Capterra, like Top Ten Reviews, like [GetUp 00:34:42]. And those are really big businesses. And so now, there’s a whole other game that gets played beneath the surface where you have to drive your customers to those sites to give you reviews, if you want to have a chance directly, you have to pay them money. It’s fundamentally changed since the early days of the company.

Andrew: Yeah. I don’t think people are talking enough about how that works. We all talk about is Yelp hiding reviews from people who pay for ads, from restaurants who pay for ads. Are they playing that kind of game? Nobody talks about what Capterra is up to. Nobody talks about any of these sites. I’ve interviewed some of the founders. It’s kind of interesting that what they try to do is be the neutral arbiter, but they get paid when you pick the right product. They get an affiliate commission.

Ryan: I know, to me, it’s something that like you mentioned, it should be talked about. And in some ways, I think there’s going to be an interesting scenario happening where I can understand why Google is sending their traffic to these sites. Try it, if you’re googling for a category term, not a branded term, then you’re out there to discover the best sites. And so they want something that’s engaging or gives people a good review of that or a good lay of the landscape.

But what’s interesting is, we know Google makes all of its money off ads. And so, if you know these companies are spending less time going back in and out of Google for these types of searches and going to these third parties. And if they’re not also clearly disclaiming whether you know how things are paid and not and, you know, I know firsthand that a lot of this, the way that this stuff is done is, you know, a little bit shady and definitely not fully disclosed. But I agree, it’s something that should get talked about more and it’s something we’re going to keep seeing a lot more of further sort of, well, like in everything we do, there’s an algorithm that kind of hides a lot of the stuff behind it, so.

Andrew: I’m surprised that Google hasn’t done to them what they did to Yelp, which is just copy the business and take it over and replace them in the search results. Maybe it’s too small for them to focus on.

Ryan: Might be too small. Yeah.

Andrew: So, back then you were going after sites like, I see it, I don’t know if you recognize . . . You do? You recognize them?

Ryan: Not that one specifically, but there was like, eBiz Online or there’s like all these types of things that you had, like you mentioned, most of them are not either around or . . .

Andrew: They put a lot of effort into their site, and then you can see where they just stopped, like this one specific case. The last featured product was internet fax, some product called Faxage. So this is the way that you were working. Suddenly you went from no traction, no results to, I think it was like the first month you got five users for free. And then, some of them turned into . . . here we go, traction was slow, five trial customers in the first month, 10 in the second month. It kept on growing though, because of your internet marketing experience. Organic search was doing well, product search was doing well. And then, second year, things picked up and I want to know why things picked up.

But first I’ll talk about my second sponsor, and then we’ll jump right into it. Well, I kind of wish my second sponsor was HostGator, so that I can ask you what websites to create today in the world as it is. Oh, you’re smiling. Would you have some suggestions for websites to create today? Should we just shift it from Toptal to HostGator? You do? What would you create today? Let’s riff on that for a bit, actually. Well, you know what, we’ll save it for later in the interview if we have time. In fact, I’ll just stick with Toptal since teed them up already.

Here’s what Toptal is, it’s a service where you can hire developers. If you or anyone else is looking for a developer, the way to work is you go to the URL I’m about to give you, you hit a button, you schedule a call. I asked Hiten Shah, I said to Hiten, “You’ve got one of the best networks out there in the startup world.” He’s a huge advisor for many people. He’s friends with everyone in San Francisco as far as I could tell. I go, “Dude, why are you going to Toptal instead of just tapping your network to hire a developer?” And he said, “It’s the matcher.” I said, “What do you mean the matcher?”

He was like, “As soon as you get on a call with them the matcher will help you understand what you really need, shape that job description and then help you find the right person within their network who will fit that job description.” So Hiten Shah, who’s founded multiple companies here and advised many companies here uses them. So many other people I’ve interviewed use them. Ryan should be using them. You if you’re listening to me, you’ve got to check them out.

When you go to, what you’re going to get is that same big button that Hiten Shah pressed but you’re going to get a big advantage that he didn’t get, which is 80 hours of Toptal developer credit when you pay for your first 80 hours, in addition to a no-risk trial period. That’s,

What did you do after that the first set of techniques worked for you? What was the next big thing that helped you grow?

Ryan: I would say it was just continuing to do more of the same honestly. There wasn’t like a real . . . We started doing, you know, some different types of online ads and stuff like that. But the majority of our growth still came through organic. I think we really benefited from the trends that were happening in the marketplace, you know, just every single year in the last 10 years, there’s just more and more online businesses or businesses or that recognize that, you know, every part of their business or life is going to become SaaS. Or the old vendors that they used to work with, didn’t offer the solutions or the problems that they were looking for. And so I think that was one of the nice big things that this business benefited from right on from the beginning.

Andrew: One of the things that you did was you had inbound interest. People would come to your site, they’d see what it was about, they would ask for a demo, or they would kind of sign up for something. And then, who was it that would call them up? What was your sales process when they did that?

Ryan: Okay. Yeah. There’s a number of different iterations. This was sort of a part of the business that unlike, let’s call it the online marketing side, which sort of stayed the same. And we just kept kind of doubling down on what was working. The sales stuff was honestly kind of one of the wildest rides to my life because I’d always built a business and I never enjoyed. I love talking to customers. I love getting their feedback. I loved onboarding. But I loved the customer success element, you know, helping make them successful, fine-tuning the business and the product to something that, you know, made them stay with us longer, etc.

What I didn’t enjoy was sales. And so, from the very beginning, you know, I never wanted to sell or spend time talking to customers that we’re in early stage prospecting. And so the whole funnel was designed around really nurturing what is now a very standard client success model. So, you know, throughout the 30-day trial, we would do things like, free accounts, you know, data entry, so we would load in their first schedule for them. So they didn’t have to do that we would enter in you know, the details for their staff profile. We would give them training until they were fully up and running on the system. And so that was something that worked again, incredibly well. I think it paired with kind of more of our like product education strategy on the marketing sides.

And then, somewhere along the way, we decided that we needed to do even better than that, or, you know, where we could try to start selling into cold leads and sort of the whole company for a number of years really changed what we really spun around in circles. Doing everything from, you know, rather than having one client success rep. That would, you know, nurture a bucket of customers and do the best that they could. They sort of managed it like an order book. Things got very intense for a while where we had a team of, you know, 10 SDRs that were like immediately trying to call every single lead, the lead only within minutes of the lead call coming in. So there’s all these types of iterations . . .

Andrew: Did that work for you? I know it works for some companies.

Ryan: Yes and no. Yes and no. I think there’s just so many better ways now to like with lead scoring and different things like, that you can figure out and you can be a lot more efficient without having, you know, 30% dialing for dollars team, you know, manually nurturing leads. I think that type of stuff works maybe when you don’t have as good of a product or maybe your customers aren’t as ready to, you know, self-discover and onboard or at an earlier stage in their buying cycle.

Andrew: And so now, how does it work?

Ryan: It’s very, very much like the original model. The few things that have changed, really, the only thing that’s changed is they’ve just segmented and you know, getting a lot smarter about lead scoring, and a lot smarter about segmenting leads. Predominantly, as the business over the past couple of years, especially under the new CEO is really focused on moving a lot more up into the enterprise. And so, naturally, these enterprise sales cycles are highly variable, but generally, you know, let’s say six to nine months long, at least. And a lot of them start with, you know, maybe a three to six month pilot before they get to their full potential after the first year, for example. And so that’s a completely different process than, you know, a small business with 50 employees that we know will close every 35 days, kind of like a turnkey businesses.

Andrew: And even with these enterprise sales, it’s someone coming in and trying out the software?

Ryan: It’s still predominantly was up until about a year-and-a half ago. And then, the other big thing that they’ve made is a shift really around focusing on enterprise-level integrations. And so that’s now where there’s a very different deal cycle, you know, oftentimes with a partner like Workday, for example. And so that’s where, you know, now we’re starting to do trade shows, again, you know, again, things that we would have never done five or 10 years ago, just because it’s hard to go to a trade show and sign up small businesses.

Andrew: Workday is like HR. I’m on the site right now. They do HR, financing, planning. It’s the stuff that the E-level, C-level, E-staff uses, right? The executives. And so they recommend you and they help implement it because of your partnership with them? Is that how it works?

Ryan: Yeah, that’s right. So we’ve got a few partnerships like this. And so this is sort of an evolution of the business. I think, like you mentioned right now, the business looks a lot the way it does today, actually, as it did, you know, maybe eight years ago. And they’re really taking things back in many ways to our roots where the goal is to be the dominant solution for employee scheduling, and recognizing that the game and the landscape is different you start talking about workforce management.

And so that was something that I was very passionate about continuing to build out the product speed and do all these other things in workforce management. Depending on where you are in customer size, customers view tools differently already using tools differently. And just the needs are very different. You know, trying to do HR at a restaurant of 30 people is completely different than doing HR, of course, with an enterprise with 10,000, 15,000, 30,000 people.

And so, for a small business, you can be their HR, their time and attendance tool when you’re down there. But at when you start moving up in the markets, they’ve already implemented a tool like Workday. And so the customers that sort of adopting us. They don’t use us for any of those things. So just like HR and time and attendance is hard for businesses. Employee scheduling is a very hard problem as well. And so what we found is that, those customers that are using these enterprise, SaaS tools haven’t solved that part of the stack yet. And so it becomes a very different problem in where we’re, you know, reading an employee data. We’re no longer the system of record, for example, for employee data. We read that in, we schedule people, we shift our time clock back so that it becomes a different type of . . .

Andrew: Okay, but it seems like a better customer because there are so many more people that you’re serving and the dollar amounts go up higher. But before I go into a key issue in this transition, I’ve got to ask you, as I looked over earlier versions of your site and looked at like Google screenshots, and so on, I saw at the bottom of your site, a link to screen sharing app called Why do these guys need that? I have some theories on why that was on your homepage? But I’d like to hear from you.

Ryan: Sure. Yeah, yeah. So one of the things that was unique, I think, about our company, or at least my investors have told me that was unique. I could build product very quickly. And so we built all of our own internal tools from the get-go. I built my own help desk, our own recurring billing software, you know, all those types of stuff in our own internal stack. And one of the tools that we use actually, for our help desk team was a screen grabbing software so they could quickly take screen grabs of whatever, you know, customer they were looking at.

Behind the scenes would upload it to, you know, an FTP server at the time eventually to Amazon and then it would, in your clipboard automatically give you a link back. And so it just became this incredibly effective way to communicate over chat, because you could immediately take, you know, small screen grabs of what you were doing. And so that was a tool that we put out for free just as sort of a, you know, way to bring back end links and stuff like that.

Andrew: You made it for your team to have and you said, “You know what, let’s just put it up on the site because other people could use it, too.”

Ryan: That’s right.

Andrew: Yeah. You know, I do notice that there are some teams that are really good at that, like Zapier, if you ever send them a tech support question and they have a solution, they will not just do a screen grab. They’ll even do a GIF to show you how to click on what you do. And that type of thing is really helpful. It’s kind of interesting that this was also posted on Lifehacker back in 2010.

And here’s how much life has changed since 2010. I’ve scrolled to the bottom to see where they got this. They got it from Download Squad, and underneath that is a video of some dude, show me how to roll a joint. And I’ve had that up on my screen the whole time waiting to ask you this question. It’s literally Lifehacker teaching you how to roll a joint.

Ryan: There you go.

Andrew: So the transition from one type of sales process to another, involved you bringing in VP of sales. You’ve said publicly, I think or at least you said it to our producer, this was a wrong decision. Why? What happened?

Ryan: Yeah. So, you know, there’s a number of wrong hires that I made, and the number of kind of different tests that we tried. And I think generally, my nature is to always, you know, move very fast, to test things very small, and always kind of be able to come back for them without having too much, you know, collateral damage, especially on the people part.

Unfortunately, with what happens a couple of times in the sales team was just the culture went wrong. And it changed the dynamic of the company where we changed from a company that was you know, all about supporting customers to all about, you know, sales commissions and just trying to kind of make the month end. And so that changes all sorts of stuff that you don’t really see it first.

And so, for example, you asked, you know, does the month where 10 SDRs, did that help? Yeah. We doubled the size of the team on . . . you know, obviously, our sales cap is exponentially higher than it used to be. And so we did have a great couple of months there. But the reality was, it looked great at first, but when you dug under the hood, we were selling all sorts of deals that were just not healthy, customers that are not ready, that were oversold on the solution. And so the type of turmoil that that creates in your funnel after they’ve become a paying customer, then it falls on the client success team, the support team.

And so yeah, I think some of the stuff that happened, unfortunately, you know, from what I’ve heard sales always has a lot of shenanigans in it. And I’ve definitely been privy to enough of it. But I’m talking about the type of stuff where, you know, a sales rep is about maybe a few deals away from making month end. And so his girlfriend’s in there entering in their credit card, like signing up the deals and just all sorts of stuff. Or we had things like incorrect attribution where you know, you’d have a warm inbound lead that would then get associated as an outbound lead, because we also tried doing pure outbound calling for a while.

And so that was again very messy. And so, unfortunately, when I found out some of that stuff, I had to let a number of people go. There’s a lot of things I run ethical and so I . . . very extreme time, I was about to close a big funding round at the time with a tier one kind of San Francisco or Silicon Valley-based VC. Just as I’m finding out that, you know, all of our sales metrics, and a lot of this stuff’s been fabricated for a while. So I put, I took a bit of a reset then and we sort of went back to some of these models that I knew worked.

Andrew: Did you blame yourself? Did you I’m looking for some vulnerability in you because it seems so far like it just super strong and everything. But I know that some of these decisions scarred you.

Ryan: Yeah. They absolutely did. I think there was a couple of key things that happened in the company that did scar me. And I think that’s part of the reason why I’m no longer with the company today, to be honest, it’s hard. I’ve been reading about this recently, this idea of like the imposter syndrome. For me, I kind of felt like that for a while, like, what am I doing here? I couldn’t find a way to sort of get back from some of these mistakes that had either manifested in the company indirectly or directly but as CEO, you definitely take all of the front for that.

Andrew: Well, you know what, instead of talking about how you got past it, let’s go a little bit deeper into this. You also hired the wrong COO. You obviously have fixed this like issue because the person who’s now running the company, as far as I could tell Chris Amani, he eventually became the COO of the business. And he grew into that role after taking on other roles in the business. But you did have a bad hire at COO and that’s one that scarred you. What happened there?

Ryan: Yeah. So I’ll share what I’m comfortable talking with. I’m thinking about, you know, midway into the, say, my tenure there. I was there like eight years after like four or five years. We recognize that for the company. I think to get to the next level, it was going to be necessary to bring in either a COO or a CEO. I was always very supportive of that, and I think, you know, looking back now maybe I wish that we’ve looked a little bit harder for a CEO right out of the get-go. I think it would have . . . Well, I’ll get to that in a second.

But so, we did. We searched for, wow, about a year and a half, I think, you know, our recruiters called it one of the longest executive searches that they’ve ever done. We tried a trial with someone actually on contract that didn’t work out, great guy. And then, another situation happened. And again, sort of just the culture of the company changed during that time. And I lost, I would say, in many ways faith in myself. I started second-guessing myself for just about everything that I kind of did as a person and I just . . . it became really hard to operate in any way after that.

And so I think with Chris, Chris has a very different profile. He’s one of the fastest learners, smartest people I’ve ever met. And so, you know, I hired him for a finance role and kind of every time there was an opportunity for something or he could help me with anything and I think that’s a great advice to anyone that wants to move up. You know, if you see your manager, your boss looking for help, or you think you can pitch in and do something, take on more responsibility to do it. It’s a surefire way to a promotion.

And so but Chris is also a very different profile. You know, Chris brings a ton of broad experience, but primarily like an operational metrics, finance type of stuff. And so I think we see each other eye-to-eye in terms of like the cultural aspects of running a business and there’s just kind of like a very low key, you know, down to earth presence that maybe it’s hard for me to explain, but that was sort of always the culture that I liked. I didn’t like you know, flashy people in suits. I didn’t like people that were, you know, trying to play politics. Politics is one of like, my least favorite things in companies and actually the reason why I went out on my own in the first place.

Andrew: And so how did you get past the imposter syndrome to accept this part of yourself and recover by bringing somebody in who isn’t just good at their COO role but became a CEO too and allowed you to take some space. How did you get that comfort with yourself again?

Ryan: You know what, to be honest, I don’t think I’m fully over that or even the transition. This is something I’ve started reading books about this actually to try to self-help my [health 00:55:15]. Like there’s this huge loss of identity when you spend 10 years of your life, literally around the clock building something. And then, for me now the transition was pretty fast out of the company, which was great.

Andrew: Were you pushed out?

Ryan: No, no, no, absolutely not.

Andrew: Okay. It was you just deciding it’s time for me to go. And you’re still working on yourself because it scarred you to that degree. Do you have a lot of friends outside of work, or is it all been you working in isolation?

Ryan: It was a lot of working in isolation.

Andrew: It seems like.

Ryan: And so I got a lot of great friends through work, but like you mentioned, not a lot outside of that. That said, that’s one of the big reasons I’m looking actually very much forward to getting back to Canada. You know, I got a free trip with all of my friends that speak the first native language.

Andrew: I bet.

Ryan: And so, yeah. There’s a lot of parallels. But yet and I think the there’s a transition that I’m still going through. I’m still trying to figure out a number of these things, so.

Andrew: Any good book on that, that’s helped you?

Ryan: Nothing that I can point to that’s been too game changing. I did one that I liked was, “Finish Big.” That one really talks about, you know, how you set the company up for the next growth and that the entrepreneurial journey doesn’t really exit until you fully landed, and you have a new identity in something else. And so that was interesting. But, you know, you asked the question, and, and I’m working on a different project now. And it’s challenging, it’s challenging, so it’s not the same. And so I’m still you know, kind of refining and discovering my identity working on this new project. It’s fun.

Andrew: I’m kind of surprised that you would go into . . . You know before we get to the new one. Let’s close it out with the branding for Humanity. I love the name, Humanity.

Ryan: Thank you.

Andrew: And it feels so . . . I don’t know, the last, I like a lot, the previous company name. For some reason I can’t think of it. I keep having to go back to my notes to look it up whenever I want to go back and do some research on it. It was more concrete. This is more expansive. Why did you do it and talk about the challenges involved in the name because it wasn’t as easy as it seems?

Ryan: That’s right, it wasn’t as easy. And I think that’s because a lot of people have, you know, fairly powerful connections with the word already. A lot of people say, “Oh, it’s for a charity.” We had people writing in like, it’s a shame that you should use this for a business when it could be used for fundraising or something like that. And so, yeah, for me, I think I always chose . . . I always approached business, or a website, for example, from literally search engine optimization, like how could you get as many keywords into the name as possible. It’s going to rank as high. And that was really it.

And then I think, you know, about five years ago, I did this exercise and we were talking about sort of what the vision for the company looked like. And, you know, if you think about SaaS companies it is pretty still . . . it’s like it’s hilarious, like there’s Zendesk, Freshdesk, like you can pivot around sort of between every SaaS business by changing either their route or the tail of the word. And in our space, it was no different. There was literally The ShiftPlanning went to work when I work, when to manage. So there was just nobody standing out that we felt from either a product or a brand perspective. And we thought that this was one way that we could do that.

Andrew: Okay. And then, the difficulty was?

Ryan: The difficulties are, the difficulty in the brand itself, I think, was just really the idea of like, the already existing ideas of what the name means to people and from that perspective. And so I think it was kind of polarizing at first. I think once we did it, everyone sort of understood and that was a good part. The challenge is that the branding actually internally wasn’t really just about the brand. It was really about kind of a new product and platform that we were working on at the time. And that was a big challenge.

So we have really been working hard on moving, you know, much further beyond employee scheduling. And that’s why again, we wanted this brand that spoke not directly about the schedule, and that really just spoke strongly about people because we wanted to have a product that would be with an employee throughout their entire life cycle. And that, you know, kind of, the pitch of the time was hire to retire, so.

Andrew: I like by the way that as we’re talking, it’s getting darker and darker. Thanks for spending this time with me. I can see it’s evening where you are.

Ryan: Let me turn on the light.

Andrew: Oh, cool.

Ryan: I’m sorry about that.

Andrew: Let’s talk then, real quick with WorkChain. I get the idea. I’m wondering, where did you see a problem that you’re looking to solve. Was there a problem when people want to get paid faster and companies wanted to pay their employees faster?

Ryan: There is, there’s a few things that the idea for the product, by the way came from my time at Humanity working with, you know, the time and attendance space in particular, you start noticing these patterns where you’ve got all the data when people are, you know, mentally going to work that you know, immediately when they’re going to go to work. And then also, after a pay cycle happens, what they’re actually getting paid for that. And so, the idea sort of being, you know, can we offer this as the service. We’ve got all the data with high certainty that we could go ahead and even advance employees money before their employers actually paid them knowing that they’re going to get paid out or we could even pull those funds back from the company.

So this was a problem that we explored actually working on as Humanity was decided, you know, didn’t align well with the focus on enterprise scheduling. And so that was the reason why I was able to go out and do this on its own. The other big trend, which I’m sure you’re familiar with is really how quickly things are becoming, how fast things are moving to like these temp-based work, the gig and on-demand economy. These are big, big shifts in the labor market. And so now you have these scenarios where you’ve got individual contractors showing up, for example, for work, and they’re incurring their own expenses to go ahead and cover for that shift, but maybe not getting paid until some time afterwards.

So those were the kind of like the big trends. And then you know, I can go into some detail one thing, you know, stats about people who are working, or living paycheck to paycheck. And a lot of people unfortunately, have to go to very expensive and what I call predatory types of loans, oftentimes just because they need to make a medical expense or other things. And so we view this as a way to kind of fill that gap or you’re not, we don’t view it as actually lending any money to an individual, you’re giving them the value that’s already theirs and then recouping it later, just because you can do that now with the [inaudible 01:02:07].

Andrew: That’s the way it works? You’re taking the money out of your account and giving it to them and then the employee-employer gives it to you later?

Ryan: We haven’t launched a part of the product yet but that is something that we will do. Part of the broader vision is actually to enable that is like a peer-to-peer fashion. So you can do . . .

Andrew: So anyone could be a lender?

Ryan: Anyone can be a lender on the platform.

Andrew: Got it? Yeah, I see that you guys have a great animation. Is this a GIF? I don’t know what it is, but it’s really well done in the middle of the, website or

Ryan: Thank you. Very, very talented designer.

Andrew: You guys do a really good job of explaining this. I find a lot of times with crypto and Bitcoin and all that stuff. The explanations make it more complicated than it seemed when people went in looking for the explanation. So now that things are changing for cryptocurrency, for blockchain, how’s it affecting you guys?

Ryan: Things have affected us a lot. We got kind of stuck in a hard spot because, you know, everyone . . . My connection got a little bit bad. Just let me know if you can still hear me.

Andrew: Yeah.

Ryan: So things changed a lot. Like you mentioned, things used to be very technical. They used to be sort of all about protocols and all this stuff that honestly, when you dug into them, most of them technically didn’t even make a lot of sense. And so what we really tried to do from the get-go was make something that was approachable. We wanted to build a real product that people could use. And that would add, that would sort of like democratize crypto or make it a little bit easier to get around with.
And so, like one of the misconceptions, for example, is around getting paid in crypto, like are you actually going to get paid than in Bitcoin, which is incredibly volatile? And when you go down to the shop, you know, the $100 you earned is going to be worth $80 or maybe $200. So what we’re using are like I would say it’s more of like blockchain technology than then anything else from that perspective.

And so that enables us to, you know, do things like not have to go to the bank, you know, cut out the bank. We can do settlements for, you know, pennies or even micros of a penny and at any time. So we call this money streaming where you can literally while a shift’s happening, you just have this steady stream of value that’s been transferred from one individual to another. And so these are the types of things that are not possible. Using a traditional fiat system, it would just be inherently inexpensive, for example, or inefficient . . .

Andrew: Because every time you transfer even a penny, there’s a minimum cost that goes into the transaction.

Ryan: That’s right.

Andrew: And with crypto, you don’t have that. And that’s what you’re trying to do. And are people less interested in this now because of what’s happening to the value of cryptocurrencies.

Ryan: They are. So there’s sort of like for us, we’re really working hard to I would say pivot and make this more mainstream where the conversation becomes more about like less about cryptocurrency first, that’s sort of like an added benefit of what we can add. So that’s a bit of a transition for us.

Andrew: So where before it was cryptocurrency and blockchain emphasized in the website. Now, it’s more about pay your people faster or get paid faster. And if you look under the hood, we’re not hiding the fact that it’s cryptocurrency. It’s just not something we’re going to put first out there.

Ryan: That’s right. I think if you think back through the main hype, everyone, I think thought very quickly that, you know, cryptocurrency and blockchain was going to take over the world and democratize everything. And there was going to be no banks and all this type of stuff and people were buying into, you know, that hype of the protocols and all this stuff taking over. And now it’s like, “Okay, show me there’s a real business.” The people that are investing in this space are not investing, you know, predominantly in tokens anymore. They’re going after equity, and they want to see all the same type of stuff, you know, as a traditional SaaS business, for example, would.

Andrew: What do you feel like you’ve jumped too soon into this? I know we’re at the end of the interview, but I’ve got to ask you, you’re a guy who just had spent so many years of your life working hard. Do you feel like maybe you should have taken a year off six months sabbatical like your dad did before getting into another company?

Ryan: Yeah, I do. I do. I absolutely do. And, you know, to be honest, it wasn’t my first dream to get back into running a company right away after just stepping down. And so I think that’s again, kind of part of the process I’m going through now. So I do. Yep, I would, I would have preferred to have taken more time off, done some of the stuff that I didn’t do and, yep.

Andrew: But this felt like an urgent thing because it no one had done it. And this space was moving so fast.

Ryan: That’s right, yeah, there was a huge element with the space of it. And then this was a product where . . . it was a very different type of scenario, like this wasn’t, you know, a lone soldier effort. I had the opportunity to work with a few of my, you know, very close friends that are very technically bright on this and so it was a great opportunity to work with them directly as well.

Andrew: Your co-founder is still working in his company too. Ivan is the creator of WorkPlus, Am I right?

Ryan: WorkPuls.

Andrew: Yep. WorkPuls, excuse me. Yeah, That’s tracks way people are doing on their computers when they’re working for you so you get a sense of how productive they are. He’s still there too?

Ryan: He is, yeah.

Andrew: Well, when do you go back to Canada?

Ryan: I have like a week of just continuing to sell stuff and then I’m back in, you know, two weeks max. I’ve never done this before. I’ve always moved and then sort of like set up and bought stuff. This is my first time selling stuff, so I’m trying to like balance, still having a place to sleep before giving up my place and whatnot. It’s fun.

Andrew: You know, there’s nothing more liberating I find in just selling stuff and moving on, even getting rid of it. It feels so good.

Ryan: Yeah. The blessing . . . so I’m in a shipping city with the big with the canal here of course, and it’s been I’ve called at least 10 companies and no one will ship even just a few boxes for us. I’m literally, you know, after 10 years, my wife and I are just going on with a couple suitcases, everything is gone. It is liberating. I’m going through all these stuff and literally half of it, I haven’t looked at or used.

Andrew: I’m kind of glad for you that they won’t even though they’re shippers everywhere, I’m kind of glad for you that they’re not taking this stuff. There are few things you might want to keep as mementos of your experience there but the rest start fresh, let it go.

Ryan: Even a lot of that stuff, I’ve just been taking pictures of it now and everything is going to start started fresh, so, yeah.

Andrew: Oh, really? Like what’s a tough thing for you to get rid of now, but you know, it’s going to feel better later to not have it?

Ryan: Honestly, the things that are the hardest stuff or the stuff that my daughter’s given me. It’s like, you know, a cup that she gave me for Father’s Day or a painting that she made and it’s things that you know, I would I would keep around my house of course, if I had a place but if I’m going to be traveling around Canada this summer, that’s stuff that I’m not going to look at and she’ll forgive me. So I got pictures of a lot of stuff and a few things will come.

Andrew: I’m staying in the same place and I still feel that I want to just take pictures of this stuff they give me and I find that the photos are more accessible and they feel less weighty. There’s less of delicacy being delicate around it around the house, worrying that it’s not in the right place, you know? Photo, we all have it, you share it, you talk about it. Hey, wait a minute, I get the photo. Just yell at Siri, Siri will bring it up. Wow, you know what? I could see your whole energy change, Ryan, as we’re even talking about you moving back to Canada and you getting to travel more. It feels good.

Ryan: I think so. Yeah.

Andrew: I appreciate you doing this interview with me before you travel.

Ryan: Thank you. It was a lot of fun.

Andrew: For letting me interrupt you like a million times. Sorry, I don’t know what, I think it’s a little bit of a lag. And then it causes me to step all over you.

Ryan: If I can ask you a question, what the story with the beads on your mic?

Andrew: I find that it helps me focus a lot. One of the things that I discovered was that my mind will wander to things that I don’t want it to because someone will say something and I get it stuck in my head or I’ll worry about something and I’ll just keep it on loop. And the stuff that I want, I don’t focus on enough. And so, as I traveled around the world, I noticed a lot of cultures had different beads like this one supposed to be more of a Hawaiian bead. And when my sister got married in Hawaii, she got the Hawaiian beads. They’ve got that. When you go to Arab countries, they’ve got the prayer beads, Catholic countries have it, but also South America, people have it.

And I said, “You know, what if I just take one of these things and help me focus.” So every time I would stay focused on what I want and what’s true, I would move a bead and then focus on what’s true and move a beat and so on. And it helped me. It helped me a lot. And so I still do it. Like even before running this last marathon, the doctor told me, “Look, there’s a good chance your shin’s going to crack here.” But it’s also good chance it won’t, just pay attention to it. So all I kept thinking was, shins is going to crack, what if I don’t finish it? And I said, “Screw that.” Finish . . .

All I want is to finish healthy. And I’m fine ducking out if the last marathon wasn’t going to work out. I’ll find a way to repeat it. So I just move the bead and said, “Finish healthy. Finish healthy. Finish healthy.” I finished great, finished great.

Ryan: That’s great.

Andrew: And you know what, and it’s possible that I would have broken my shin. But I don’t want to have the thought about it the whole time and God knows thinking about it the whole time leading up to the marathon would have led to a worse experience even on marathon day. So that’s what it’s about.

Ryan: That’s great.

Andrew: Cool. Thanks for asking. If anyone wants to go see Ryan, don’t leave him alone for a little bit. Give him some space. I feel he needs it. But you do have a personal site. I don’t have it here in the zillion tabs that I have up on my screen, don’t you? It seems like

Ryan: Yeah, I do. It’s a little outdated. But

Andrew: Yeah, I thought so, I appreciate you doing this interview and I appreciate the two sponsors who made and oh and Fyfe I should say is, F-Y-F-E. And I want to thank the two sponsors made this interview happen. The first will do your email marketing right and I hate that I just say email because they do so much more than that, but it’s smart marketing automation. Go check them out at The second will help you hire right, it’s called Toptal. Check them out at

And let me know what you think about this interview being edited. Our usual editor is out on maternity leave. Dan is doing this. Dan Gargone, I’m really interested to hear if the audio is coming across to you guys well. So let us all know contact at, tell my whole team. Ryan, thanks so much.

Ryan: Thanks, Andrew.

Andrew: Goodnight. Bye.

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