Unfiltered: #ChooseToChallenge with Alison Taylor

All right. Hello and welcome to Unfiltered Choose to Challenge. This is a Cloudflare TV session and I'm so honored and privileged to have our guest today, Allie Taylor. Allie, it is so nice to meet you. We just chatted yesterday. Allie is the co -founder and co-CEO of Jane App and we'll talk a little bit about Jane Software Incorporated and what it does and the amazing story she's had on bringing it to life. So Allie, welcome to the show. Thank you for having me. So nice to be here. Yes. So I think we were just trading resumes and looking back at what our degrees were in and mine was in molecular biology and I wound up the head of engineering of a cloud for Internet structure and you have a BA in English with a minor in psychology and so I thought let's see if we can tell the story from there. How does one start with that kind of liberal arts education and become a tech CEO? How did your journey go and wind up here? Does anyone ever know what they want to be when they grow up? I always think it's a strange question. I certainly didn't. No and you ask your kids and you ask in grade nine, let's choose your course selection because what do you want to be when you grow up and everyone knows like five careers and no one is going to say I want to be a tech CEO except for my kids although my youngest son says he wants to be my assistant. He's going to bring me coffee and he's going to step in when I'm sick. He's like I'll just fill in for you when you're sick and bring you coffee. I'm like that sounds pretty good actually. That's what my youngest son wants to be. How did it start? My parents are both physios and so originally I thought I was going to be a physiotherapist and so I went to school thinking I was going to do my kin degree and then go into physio and then I had teachers just telling me in my English classes that my English, my writing was so amazing. Have you ever had someone tell you you're really good at something and then it sort of changes your life because some external person said you're really good at this and so I ended up like not really loving the kin courses and then I ended up finishing a degree in English and same with psychology. It was super interesting and so I ended up minoring in psychology sort of by accident. Then I thought I was going to be an English teacher for grade 12 because I love teenagers. I thought grade 12 you can have real conversations with people and then as I was going to school full-time I was also managing my parents clinic and so at the time I worked full-time. I went to school full-time and I really love clinics. I've grown up in clinics and I love the whole atmosphere of a clinic and then I was always just looking to kind of help and solve problems and there's two physios there that went on mat leave and wanted to come back and work in a different style and I was like why don't and my midwives who had birthed my babies were looking for space and I was just like why don't I just open a practice and I think there's some naivete of youth that allowed me to think that this would just not be a big deal and I just started asking like the bank for money and I made a business plan and I opened a practice and a lot of my career and I think everyone's careers probably is just trying like just saying yes to things like why don't we just try it and just taking the next step and so from their canopy I opened a multidisciplinary health care clinic which was super fascinating. It was a real education because I had to learn about all the different disciplines that I didn't know about so I would enter I put ads out saying I'm looking for therapists to come join this practice and I would interview them and I would interview them more than they would you know I would say to them like well what makes your discipline so special and why did you choose to be an osteo or a naturopath or a massage therapist instead of the many different disciplines that you could have been because I really do believe that a practitioner would be a successful practitioner no matter what discipline that they chose. It's like there's so much about the person who's a good caregiver which we were talking about earlier with med school the type of person that becomes a practitioner and so from there I was opening this practice and then I was looking for online booking and electronic charting. Before we go to the online booking. I have like a small story for you. Yeah exactly but let's just pause. So you wanted to be a teacher and you grew up around physiotherapists and one day you sort of had this epiphany like actually I want to start my own business. I want to be a small business owner and I want to I want to like put up hang up shang and shingle and see if I can get people to join me and you know take out a loan and start paying them and start seeing patients. Is it honestly Ali? Is that the process? It does sound strange because like we were talking yesterday about the idea of an entrepreneur and I don't I don't I didn't adopt the title of entrepreneur very easily. Why not? I really thought that the um an entrepreneur in my mind the ones that I knew of in my like surrounding circle were the type of people that were their whole they didn't care what the idea was like they were like I just want to find an idea and make a billion dollars and was the whole like central purpose of being an entrepreneur and so they would find their idea and then they would mortgage their house three times. They would like have you know just there isn't really a solid concept of how this was going to work but they would be all in and they would for me it felt like putting your family on a boat and sailing into the ocean with no land in sight and no compass really. That's not what canopy was for you and so that's why you didn't feel like that met the risk wasn't there to be part of entrepreneurship in your mind? In retrospect the risk was higher than I knew but I think there's something to be said for not really understanding what you're getting yourself into and I have I think the blessing of confidence that maybe isn't really backed up by a lot of facts at the time. I had a really simple business plan. I'd run clinics. I knew I could run a clinic so there was like a there was a subject matter expertise in that that I was very comfortable taking that leap because I knew everything about how to run a practice. I'd been doing it for I'd been a receptionist. I'd been managing clinics. I'd been working with therapists. It was there was nothing about this world I didn't know. Was there any job? I remember reading an article about James Cameron once you know the movie director said he could do any job on the set. Do you feel like you could do any job? Like you knew exactly how each one of those roles should be should be performed? I probably like I couldn't actually be a therapist because I haven't had right for that although people James could probably be an actor but still I feel like that's actually kind of a hard statement to make when you're part of like even now with Jane like I couldn't code. I did do one. I did one commit and it had a typo in it and I broke Jane and they had to fix it so that was like my one and only. They like you're in you're in great company. There's a long line of great leaders who commit so but but I think the the key term here is the subject matter expertise like it was something you knew very well and that you know I would I would I would argue with anyone who who claimed you weren't an entrepreneur that to me is the very definition of entrepreneurship what you did when you started Canopy but I think you were about to tell us about how all of a sudden an information technology problem showed up as well as you were as we were dealing with something as simple sounding as booking. So what what was the what was the problem and how did that turn into Jane? Yeah it was a dual problem so it was booking and electronic charting so I knew I had eight treatment rooms. My business plan depended on all eight treatment rooms being income generating space and I couldn't have paper charts because paper charts would take up an entire room so that was my I had an issue and then I opened the clinic in 2011. Yes 2011. I have to think back to like who I was pregnant with at 2011. That's your timeline? It's interesting for me. Yes that's 2011. I think I told you that I was like cleaning floors nine months pregnant for the opening of the practice because you know when you're starting a new business you don't have a lot of extra funds. Absolutely. So you are doing everything yourself including cleaning. I was cleaning the office. I filled that role and so I needed electronic charting and I needed online booking and at the time I used to say that like I was looking around for online booking solutions and it would load and I would be sitting there waiting thinking that the page was only partially loaded because the designs were so horrific. Like they just were not attractive. They weren't welcoming and I'd spend a lot of money on the actual physical space. I'd spend a lot of time you know creating a brand and creating and I think my my website and my online booking I was thinking about it like my online waiting room like this is where patients who are looking for for care it's their first experience with the clinic and so I knew I needed a front door. It's the online front door. It's the online waiting room and if people are looking for care they're going to keep looking if they can't actually book an appointment. So online booking to me was like it was just vitally important and same with electronic charting and so I was looking and complaining and at the time my co-founder and co-CEO Trevor he was he had a marketing agency that was working on my website and my design of my brand and so he said well why don't we just build we'll build it for you as part of your website and the magic words that start all great ventures. Why don't we just build it ourselves? Why don't we just do it? No problem and so this was like I became this accidental entrepreneur in this story as a second at the first time I guess it was more intentional. I'm going to go out and start this business but the second time we were just building some a tool for my own practice and then we built that. It everyone charted on it. Everyone booked on it. It worked great. I think I have I pulled up some old emails from the time of me being like you know the body chart is this is being a bit weird and then they would fix it for me. It was only a couple of things that needed fixing and it just ran on a mac mini in my practice attached to my website. I was just a very like it just was it was great and it worked for all our different practitioners. So it had to be flexible. It has to be customizable right from the get-go because I had so many different disciplines. So yeah I always say solving your own problem like there's no better business idea because what happens is every other people have the same problem. Everyone yeah there's almost certainly nothing unique about like if you have the problem there's a very good chance other people do too and that of course is the key insight that allows a business to scale. So there must have been so the same in the same way that there was an instinct in you to you know what I'm going to start my own practice and Canopy was born. There must have been a moment where you said to yourself the tool is actually a more interesting thing to put my time in than Canopy and so let's build something horizontal. Let's build something that will scale to different applications. We've got the kernel of a flexible system here. What was that transition like and when did you realize that actually this is what I want to do? Yeah it was a real it was being pulled. It's always being pulled so for the year and a half because the online booking was visible people were asking me what are you using and Trevor's company's name was at the bottom because they'd built our website and so they were asking him as well. So we were both getting messages from people and we're like well you know it's just a thing. It's just my thing and then we suddenly thought you know okay people want this and it's it exists. Why don't we partner together and build it out and then make it something that we can and I wish I could show you the original business plan. We both intended to work on our existing businesses. We had I think maybe 12 staff over like a five-year plan and it was just going to be a cash cow that we did as a side hustle and we just it wouldn't need any work like it wouldn't need any people because it would just be so easy because I'd used it for a year and a half with very little like maintenance needs or anything. Yeah and so we just thought it would just be this little thing that just ran on the side that that is not that is not what happened and it wasn't it wasn't the plan. It wasn't what ended up happening for sure. So tell us what did happen actually and tell two parts of it. So part of it here is you know you're a co -founder and co-CEO and so there's and you said yourself you're not an engineer or a technical person by background so your co -founder here was a critical part and one of the questions you often hear when people have an idea is they'll say well I'm I'm a good technical head but I don't have a head for business or I'm a I've got a great idea for a business that I think I could really have a lot of fun selling but I need someone technical to partner like what is it that makes a good co-founder relationship? How did you how did you two find each other? How does how do you split up the duties especially since it is a co -CEO relationship? Yeah it's worked out I mean co-CEOing has worked out super well for us and we both we're both kind of perfectionists in our own way and and deeply competitive so we have to have equal equality in our relationship or it would break down so we know that which means that we ask for two seats to things like in the first few years we were just we must have been so annoying to people like if they invited us to something we'd be like well we both have to come because we're both CEOs and they'd be like only one person can come and we're like well we can't come then because we're both the CEO so that's changed a little bit now as we've grown I've become I've been doing more of the public stuff and he's more on the technical team but we always we split it up where I did customer and he did product well he did the engineering part we're learning now and we together kind of did product and business and so that was just it was kind of a nice division of duties and we both can speak into the other person's like side of the business but yeah you would just like say well capitulate like this is your you have more authority in this area and I have more authority in this area and if we disagreed we actually usually delayed making the decision until we would agree so we had I think mutual respect is very important in co-founding relationships and then I always say that every business is going to look completely different based on the founders so it doesn't really matter what your founder's strengths are that will shape the way your business grows if we had a sales founder Jane would look very different than it looks today but we don't we have like a cut we have our customer and we are we are a customer product driven business and so now our now the tricky part is trying to bring in those other areas of expertise at the same level and I was talking to someone else recently and they said anyone you bring into your c -suite needs to be a delayed co-founder so what that means is they have to be the level that you would go and start a new business and you would say I want you on my founding team and if you can't say that they shouldn't be part of your c-suite and I thought that was super fascinating actually as I'm thinking about you know how we scale these different parts of our business as we get bigger. Yeah I clapped for a phrase I think it came from a someone who blogged about it once is an expression give away your legos and the idea is that as you scale as you grow these things that you've held very close and that you've controlled all the details about you now have to completely trust to give to somebody else and it's it's not you know sometimes people think oh we get to scale and I'll hang on to the good parts the fun parts and you know we'll have someone else deal but that's actually the opposite of how healthy scale looks like it's giving away the stuff you really love and that you're really good at and that's why I think it's so important to find people who you would have been co -founders with I think that's a great metric. Yeah and also recognizing that it's okay if your company looks different than other companies that are successful. So I always say like there's a path up the mountain you're trying to get to the top of the mountain that's your goal there's like a thousand ways to get there there's a thousand and some are shorter and some are longer and some are more difficult and some are easier but no matter what your path up the mountain it's going to look different than other companies because you have different people like and you have a different even every company is so different like just culture wise and you know ethics and what kind of decisions are you willing to make and what kind of decisions are you yeah and then this is like the opportunity distraction we were talking about too leading a company is just constantly deciding is this an opportunity or a distraction in front of me and so that's the that's the fork in the road like which path are you going to take up this mountain is this an opportunity or distraction and then choosing your I use mountain analogies all the time I do I feel like I feel like it's a perfect model you know if you if you had if you if you put a video camera on someone when they're hiking they they they look they don't look like they're having a lot of fun but once they you know once they reach the next next milestone whatever it is it feels so rewarding. Let's talk a little bit about what what was hard and what was easy and in Jane and you know which which problems were harder than you thought they would be and which ones came easier more naturally than you thought they would be as as as your team you know was scaling the mountain of building Jane. Yeah yeah I think I was talking to another founder recently as well and he said something that I quite liked he said revenue is just the result of making the right decisions and so I think revenue has been easier than we were expecting because it wasn't of all the things to be I know that's a pretty good one Allie you know the money just keeps coming in I we show up to work and and people keep paying us sounds great that's terrible should we edit that out you can't even we're live okay well I just think that it it was easier than I also thought to get like people and like allies in the tech community like Vancouver is a super super generous and welcoming that's where we are we're in Vancouver Canada and actually that extends beyond that every the the tech community is incredibly generous with its knowledge with its expertise like with its time about it yeah there I have never been it's it's incredible the amount of people who've done it before who are willing to talk to you and share their experience and their knowledge and their and their contacts so that was definitely unexpected I had never experienced that before the small business community is a little bit more scarcity and there's a lot of competition between kind of therapy so localized kind of interesting you're saying in the contrasting the small business community versus the tech community yeah yeah that felt very yeah I was very surprised by the differences in running a small business to a growth company we originally built Jane as a small business and so it wasn't until kind of a year or two in that we entered the tech world yeah and we learned you know even stuff like the government supports in Canada for a tech company is amazing like I can't believe the funding that's available for tech companies and I know everyone's always trying to fight for better funding and I'm right there with them I'm like we're building we're creating jobs we're building industry but as a small business I didn't have any support like that from the government so I'm always so grateful for it because I just think it's incredible yeah I think I think part of what it might be is that um in many ways the problems that big tech is trying certainly I feel it's a Cloudflare you're trying to do things that no one's ever done before so the very least you could do is share notes with your with your with the other companies they're also trying to do something that's never been done before I love it I love the tech community so much it's wonderful the amount of collaboration that happens and yeah it's just is really friendly I know that surprised me for sure I want to emphasize also that um you know I think uh as someone who had a startup myself for a few years um you know there's no I don't believe that there's such a thing as an accidental success like I mean I think it's the combination of all that hard all those that subject middle those years of subject matter expertise uh the attention to detail that you were talking about you know worrying about what the front door looks like that laser focus on customers and their success and then leveraging the tech community to be sort of foster an environment of constant learning like I would argue that that's the actual that's why you're why why your revenue is coming uh and not like it's a lot of hard work and a lot of passion and uh and that's that's really what's behind it we don't know what we don't know because neither of us have ever worked for a company other than Jane and so often we have like I have a new VP of customer support and who's just taking on my baby like my just my you're giving away that Lego set right yeah I'm doing it I'm I'm doing it it's harder but I'm doing it and um he I don't like I don't realize that it's not normal for the CEO to fight for more resources for customer support I'm like you need more people you need to hire more people right now and then we're going to figure it out in the model because the phone wait times are too long like and he's used to being the one coming to the CEO and being like can we like we need to be better resourced and so I I think it's true like you like I said every company is is different we don't recognize how we're different than other companies because this is you know the one reason we do things like this it's so much fun to talk and share notes one thing uh when we were when we were chatting yesterday uh you said that I really loved was your approach to when is it learning when is it a mistake and when is it learning and when is it a problem uh can you talk a little bit about about your I thought you had a lot of a fantastic framework for how all learning implies a you know necessarily means something didn't go the way you thought it would so now we're going to you're going to take advantage of what you now know I do think that's weird that people call it a mistake the first time I don't under I don't really think it is a mistake the first time it definitely is a learning the first time something doesn't go well and the way that we we mitigate for that and that we take very calculated risks so we make small bets yeah like I'm not the entrepreneur that like triple mortgages my house so we make a small bet and then we see if it works or not and if it doesn't work you know then that's a learning but also in people's behavior in a new role or like if someone makes a mistake a mistake what typically would it be a mistake like they put out bad code or whatever it is or they sent an email at least double sent a saved reply email like would be a great mistake okay so we you know we have I don't want anyone to feel like we're robots over here we care about you so if we're sending a templated email twice to the same person that's a mistake but that is fine one time we're just like oh this is why we don't do this this is how you make sure you fix it this is how you can check on previous conversations and then if they do it again now it's a mistake because now you should know better and then if you do it again that's a problem so that's when we get to the point where like this isn't working out so you I guess people call it sort of a three strike rule but it doesn't seem like that when you think about it in that way it also I like your framing way better learning it's a mistake it's a problem and then you know and we probably go to four or five we all go to end there's no way I know n plus one yeah exactly but I but I think what I really like about it is it also emphasizes that all learning requires mistakes like you can't but like you that is the necessary step on the way to figuring out what works and what doesn't is giving yourself permission to be a place where you can explore try things you can move fast and you you know when you do all those things you won't get it right all the time and that's is the grace it gives me as a leader too like you know I can be like oh that didn't work like I made a like that wasn't the right call and if I if we're okay with that across the company then everyone is going to be okay with that and we talk about that a lot as we bring in we bring up our leaders from internally very intentionally we do we can to try and bring up people from within instead of hiring from outside because it's it's just it's just a decision we made like we want to do it and so we're quite we're quite open about the fact that these people me included are doing a job for the very first time I think I said every day I wake up to a new company that I've never run before like we hired bigger than you've ever been before yeah yeah we hired eight people we had we had you know like it's new today it's a whole new thing I've never done this before and our leaders are the same and so we kind of say like if they're making mistakes you need to everyone needs to help everyone it doesn't matter what position they are in the company you need to help everyone be best the best they can be at their job and then when you become a leader one day everyone will have the same grace for you when you make a mistake or when something doesn't go quickly and so it's kind of about trying to explain to the whole company like we're all humans we're all humans so just put yourself in that role and same with our customers everybody's just a human so can we operate that way because it would be a lot nicer if we all did yeah just empathy first one thing I wanted to touch on in the last few five minutes we have here is startups are notoriously hard and being a founder being a CEO is even harder and so I wanted to ask you like how do you find that balance you alluded to that you have children one of them wants to be wants to grow up to be your exact admin and and and substitute when you're not around but like how do you how do you manage that you know that's a tricky problem of you have got a growing family and a growing business and and and how did you approach the challenges in there I did want to say that since working from home my youngest son does bring me coffees so he's already I taught him how to make espresso actually the first time he tried to do it he peeled the nespresso pod and poured the grinds in thinking that there you go first time that's that's a learning right okay he has not done it since so I think he's well on his way to being a great employee he poured the grounds into the water container at the back thinking that this is how you make coffee it makes sense anyway totally but yeah I think I read an article recently that talked about the role of the ideal mother and the ideal worker and it was so it really hit me because they're they're ideologically opposed because both require something different as your main focus like and that's just the culture we live in the culture we live in says the ideal mother is 100 focused on her family and children and the ideal worker is 100 focused on their job as their primary responsibility and when I realized that those two things couldn't coexist at the same time I just decided I didn't care anymore I was like I'm just let's we can't play by these rules like there's no winning game and I like to win and there's no winning that game and so I just try to think of my family as a unit and my work life and my life as a unit that's very separate from the world in which I live as much as I can and and recognize that you know I'm just going to do what works until it doesn't work anymore and it changes your family changes every day same as your business like my kids are 13 11 and 9 and what they need now is very different than what they needed when they're little it's going to be very different from what they need next year and so you just kind of adjust everything as you go and then when stuff starts to crack you just make decisions to change that so I'm fortunate as our company scales I have more flexibility in my role when I was little like when the company was little I would go back to work after bedtime the kids would go to bed and I would work sending support emails till 4 in the morning and I would say well there's no one else to do it like if I'm not doing this no one else is doing it and so that was my life at the beginning and I was cleaning the bathroom when I was pregnant because that's what was needed at the time and my son came and sat in a bouncy chair with me you know when he was born and I got to hang out with him at work but he would come to work and the midwives patients would practice on him so you just you make adjustments so that you can you know deal with whatever's happening in your life at the time and like I think I'm very fortunate obviously because as a as an entrepreneur you get to make your own schedule so yeah and but I think I just wanted to say how unbelievably impressive and amazing that your story is Ali honestly like all of this is just exactly the kind of inspiring story that I think I think people watching really really want to hear it because it's even the way you're describing it like staying you know taking care of a family and then you know sending emails until until the small hours of the morning I know that you were you're doing that not out of a sense of duty but out of a sense of love and passion for the business and from wanting to serve your for your customers and that's I think the most important ingredient for for you know for a leader and for business and it all ties together this has been so so much fun talking to you I can't believe how fast we are in our our last minute and I just want to thank you so much for joining us on Cloudflare TV today and we're talking and big congrats on all the success I'm very happy to have met you and I'm really really looking forward to seeing all the great stuff that will come out of your out of Jane in the future and and look forward to again soon thanks Allie super fun thank you this year I choose to challenge the biases often associated with gaps in employment history for lack of certain formal qualifications when hiring more women in tech amplifying the voices of women and non-binary people around me reminding myself and encouraging my peers to examine our own implicit bias and doing my best to model the culture of empathy that I want to live and work in I choose to challenge by not accepting the status quo speaking up for myself and for those that cannot speak for themselves I will support other women and lift other women up applaud a woman acknowledge her presence listen to her consider her ideas as she grows if she is progressing faster do not question it a man only gains respect when he excels not speculations I choose to challenge by not accepting anything but equal pay and equal treatment in the workforce