Alanna Harvey

Since its inception in 2016, Alanna and her team have grown the Flipd community from 0 to over a million users, in more than 100 countries. Alanna is infinitely focused on improving the happiness and well-being of the next generation through thoughtfully designed technology.

About Flipd: Flipd is a Digital Wellness Company that uses behavioural economics to engineer well-being and nudge people to be present, focused and happy. Flipd has been featured by Tech Crunch, the New York Times, the Wall Street Journal, the Washington Post, WIRED, and over 200 other publications worldwide.



Alanna Harvey talks about her unexpected, up-and-down journey of entrepreneurship and what it has taught her about resilience. She also shares what it is like to run a company with her life partner and what it means to be truly there for someone.


I should start off by saying thank you for agreeing to do this. One of the things that I think I loved was when I heard about your story and the inspiration for your startup. I think it's so powerful what you're doing.

We first came up with the idea it was because Cristian [her co-founder and boyfriend] had noticed the behavior shift so dramatically in his younger brother. Cristian and I have been together for much longer than this company so I'd seen him grow up as well, his little brother.

It was really surprising for me at the time. Back when I was 13, things were a lot less serious for a 13-year old. To watch how social media and technology was shaping his life it was a bit scary.

I remember where I was, how old I was, when Facebook became important in everybody's lives. I remember that feeling when people were starting to talk about social media. It was very weird. Taking selfies and hoping people will like your pictures and bringing digital cameras to parties because you had to document your life. Now it’s become so normal in our lives.

I can only imagine, the younger and younger that this experience is happening to kids. It's 12 year olds, 10 year olds, and younger, that are just depending on their social media presence as a way that gives them validation and meaning. It's not the way that it should be.


Yeah. When you were sharing about that, oh man, I feel like I resonate on that on several levels. I was just even thinking about my own childhood and you mention about the social pressure. I was pretty awkward as a kid, and dealing with bullying and body image.

I can't imagine how much the pressure is now, seeing things see things like Kim Kardashian and Cardi B like it's such a normal thing.

I think it's very detrimental for young people because you care too much. For me and my friends, we’re older and nobody really cares. It's not that important in all of our lives, you know? Is there something that we could be doing to get young people to see that it's not so important?

But there are some people from different life stories and backgrounds who put a lot of pressure on social media and attach social media in their lives in pretty harmful ways. People of all ages are doing it. So I think when technology or social media has become a negative aspect in your life, like any relationship, you should learn how to let it go. I think that a perspective many people really struggle with.


I remember when I was teaching in private schools, it was so different. Now many schools have a policy on banning cell phones. They won't even allow them in the classroom because students can't even control themselves. That wasn't an issue before when I was teaching.

To be really honest, looking at a lot of the younger generations, social media is just part of our lives now. It's like the way I remembered the day that I discovered email. It's like, "Oh, I guess this is going to be part of the fabric of society, whether we like it or not."

Yeah. I agree with that, and in many ways I often think: what does this all mean? Because I am in no way against the use of technology, or the use of social media. I think that there are many ways that it can be used very positively.

To me it’s about identifying when it's become a problem in your life. It’s about awareness. When it's taking up too much of your time, when you're placing too much meaning on it over other things that are healthy and good for you, that's where a line should be drawn.

In the business world, I think there has been a complete lack of etiquette around use of email and Slack where it's like you have to respond at all hours of the day. People can interrupt you in the evenings and on the weekends, and take your mind completely somewhere else when you were intending on relaxing or spending time with your family. I think that's a huge problem that technology poses that will be an interesting problem to solve over the next few years.


So here's a curiosity I have. I know a lot about the origin story for the company and I love that whole piece, I'm so curious to know more about personal story as well. Like how'd you get into this world? What inspires you?

Well I definitely did not grow up thinking I wanted to be an entrepreneur, but there were signs of it throughout my childhood and into my teen years that I was bound to start something. When I was in school, I had more of a creative side — like when I was in high school, I ran a fashion show that was actually kind of a big deal. We manufactured this rotating thing that the models would stand on at the end of the runway. That was in my final year of high school and everyone thought I was going to become a designer or something. But as it turns out, I went to Ryerson for business.

I initially applied to be a journalist at a few different schools but I didn’t get into the programs I wanted to get into, but I did get into Ryerson for business school and I just really wanted to come to Toronto. That's what I wanted, so I came. I turned out to really enjoy business and specifically, my marketing and communications degree. I really enjoyed that program and the whole time, I was always very curious about user research and understanding why people do things. How can we influence people to make decisions? That was a budding desire when I was in school.

Then I graduated, I was offered a couple of different jobs. I lived in downtown Toronto since I moved from Ottawa, and so I just kept serving. I was serving in a restaurant, I really loved the freedom and flexibility. I was saving a ton of money, I was making a lot of money. I liked having my own hours.

So there's the taste of being an entrepreneur and doing my own thing — having a different lifestyle than my friends because they were all going out and getting normal 9-5 jobs and thought I was crazy. But I had different goals and I was already going in a different way.

At the same time Cristian had been starting another company while I was in school. I think he wound it down maybe a year after I graduated, came up with the idea for Flipd, and we both started working on it together. Then we got into an incubator and I quit everything else that I was working on and we were like, "All right, let's do this."


I love how there’s a theme of freedom, even back then.

Yeah, my personal growth over the last 10 years is a lot different than some people. I moved to Toronto when I was 18, moved out of my parent's house and came here, and never went back home. I had saved a bunch of money from when I was working in high school. I started working when I was 14 because my family wouldn't just hand me an allowance. It was like, "Go get the money that you want to spend." I started working when I was 14 years old; I had a part-time job.

So I guess having the freedom and independence to do what I want to do has been a pretty common theme throughout my whole life. Go out, figure it out yourself, and earn it.


It always amazes me the kinds of stories that the people have or the kinds of things that people have survived through. And yet still have managed an entire company at the same time.

Yeah. It must be an important trait to have as an entrepreneur. But it's one that no one likes to talk about because people want to always seem like everything's going great.

You don't have to always be like, “Everything is awesome, everything is great.” Sometimes we can be, "Maybe I'm not having the best week but I'm also doing the best that I can." Giving yourself the permission to accept that nothing will always be perfect, but you're doing the best that you can.


Wow, that sounds like quite a journey. You're obviously now in the tech industry and a founder, so what's been the most surprising part about your journey?

Most surprising: my own resilience. I have endured some experiences that not a lot of people who aren't entrepreneurs have experienced. I've operated on no income, making people unable to understand how it's possible that I have an apartment in Toronto that I'm paying for myself.

For example, when we first started Flipd, we had an MVP [Minimum Viable Product] and got into an incubator in Mexico that was affiliated with the university network. That whole experience was really interesting because it not only were we trying to start up, we were also trying to live in a new country for the first time. I feel like that was sort of what kicked in my grittiness as an entrepreneur. Realizing like, "Oh wow, I can actually deal with some crap." We didn't have hot water for a week, we were in sketchy vehicles to get around.

Then we lived in Ottawa for some time after that, also trying to get the technology off the ground. It was like running on fumes, but we also found ways to be content with what we had. We couldn't afford a gym membership so we were working out a school playground. That was fun. I did that for an entire summer because why not? We would run laps around the field and then do pull-ups and stuff on the monkey bars. There would be kids playing at the park.

When we finally decided, "Okay, we have to move back to Toronto, we have to grow our team, we have to get our own office." These were all things that we just decided one day. So we got in a car and we went. At the time we didn't have investors yet or office space or a place to live, but we found all of that within about three months of getting to Toronto.

That would be what has surprised me the most. My own grit. It's been amazing how much I think my personality has evolved in such a short amount of time.


The other thing, and I ask this because I'm so curious, you and Cristian have been on this journey together. Both as romantic partners, but also as business partners. And I wanted to ask, what that's been like for you?

I ask this because I remember when I was building companies the last 14 years, I always had my baby brother. It was really interesting because I started having conversations with people in tech, a lot of people said, "Oh, I don't have a spouse or I don't have a sibling who's also a founder." I'm just so curious to ask about that, because it sounds like you've had this journey, but also this incredible partnership.

For Cristian and I, it's completely made us stronger as a couple. You can ask any of our friends or family members, it's true. It's not a front. We're not having issues at home. Like the business, we do a really good job complementing each other in different skill sets.

We also have a unique experience that most founders don’t have, which is that we have a stoplight. We know when we have to step back, turn off, and chill, because otherwise that would damage our relationship if we just were working to the bone. We have to have date nights, we have to have our weekends, we have to go exercise, and we have to have dinner together and not constantly be talking or thinking about work.

What that allows for is that we have really great balance between our work life and our home life. I hope that we start to see more of a celebration of couples that work together.

One example, Michelle [Romanow] and Andrew [D'Souza of Clearbanc], TechCrunch wrote about them, their recent raise, and the reporter included a little negative blurb. Something along the lines of, “they're a couple which is typically frowned upon but it seems to be going well.” Why is there such silly stigma?

Those two are the most impressive people I've ever seen independently and they've co-founded a company together too. Who cares that they’re a couple?

I'm looking forward to the next decade of entrepreneurs that start to recognize that it could be empowering to be in a relationship and trying to start something together if you are good together.

I think I owe much of my resilience to Cristian because he himself is the most resilient person I know. His life story is completely different than mine. He's an immigrant from Colombia who was living in the U.S. for 10 years and then came to Canada and became a citizen here. He’s got the most grit of anyone I know — when he has a goal he finds a way to achieve it. He ran an Ironman last year for the first time and then ran it an hour faster this year. An hour faster! As his co-founder and partner he inspires me every day.


I so love that we're on this topic because when I was an educator, I went into private schools because I wanted to study legacy families. I taught Canada’s billionaire families because I wanted to understand the entrepreneurial mindset. When we talk about a “legacy” family, it means when a family is passing down a business across generations.

Many of the families I worked with, they groomed their children. When their children married somebody, their spouses became part of the business. I saw that and I'm like okay, my brother and I can build a successful business when we work together as a unit. When we're working together not just in business, but supporting each other emotionally.

Yeah, that's so important to me, supporting each other emotionally. Leading by example. That's why I don't want to burn out because I don't want my team to burn out. If I can go home at 6 PM, so can they. I don't want people feeling like they always have to be working and they don't have lives outside of work.

I want to celebrate their lives outside of work and the hobbies that they have, the things that make them amazing people. I've always been a work to live, not live to work.

We as human beings should find a lot more meaning outside of work, not just in our work. There are a lot more ways that we can find meaning in life. I know a lot of tech founders would disagree with that, but it's really important to have at least a bit of that mentality, so that you're not doing things like burning people out unintentionally.


This whole thing with mental health and how prevalent the issues have become speaks to something much, much deeper. When all we do is work, it overtakes the conversations we have with each other too. I really feel it affects our ability to see and hear people for who they are as individuals, not just as workers. What do you think?

Yeah. When I walk up to someone I haven't seen in a while, and the first thing they ask me is, "How's your raise going?" All I can think is: “Are you serious?”

I've really started to make sure that I'm asking, "How are you?" And emphasizing, "How are you doing?" No, I don't want to hear about your company. Tell me how are you doing.

I actually had a conversation with a founder and he did not look well. I was asking him, "How are you?" And he starts talking about the company, I was like, "No, no, no. Are you okay?" And started saying the shit that's not going well in his personal life. I was like: “I wonder how many people have asked you that today in your office or your co-founder. Does your co-founder know what you're going through?” I didn't. I didn't go deeper. We were at a networking event.

Yeah, these transactional conversations. I'm not sure what someone else gets out of asking me how my raise is going. Do you have nothing else to ask me about my life? So I'd love to see more of that honesty, openness, and care for other human beings in this space.


Yes, that's my hope as well.

I think it will be. Especially with the people that you have sharing these stories and making sure that it's people who have some sort of influence on others. I think that's what will make this conversation more powerful.


Well, thank you for being part of this movement. Grateful for you!

You’re welcome.

Cherry Rose Tanwave1