I am so excited to have you on the I Am Unbreakable podcast. Thanks so much for being here.
Yeah, it's good to be here.
Where were we this morning? How much fun was that?
We did breakfast television this morning. We talked about International Women's Day, all the mistakes that women make during pitches and, you know, then having Dragons come full circle.
I love that. And you had what, 2.5 hours of sleep in the last 3 days in a snowstorm. So, I mean, it was just going to happen that way, right?
Exactly. But you just came like home back to Toronto, I think just what, a couple of days ago from what was the weather like?
Barbados. Oh, it's beautiful there. It's like perfect 28 degrees every day. So, I get to escape in the winter.
Well, it's funny cuz I was watching one of your Instagram and I think you were thanking somebody on the island saying, 'Thank you so much for sharing a piece of your paradise with us.' And I'm looking going and we're here like digging ourselves out of the snowstorm. I'm like, 'Why does this not feel right?' Do you try to get away quite often?
So, I grew up in Regina, Saskatchewan. Like, I lived through the worst winters imaginable as a kid. Like, every Halloween costume I wanted to be a ballerina that had to fit over like a giant puffy jacket. I mean, the snow starts there in like usually the beginning of October and like sometimes it's there until like somewhere in April. So, I did a lot of cold winters. Now I try and do and it was actually COVID that changed it. I went to Barbados for a week and then I stayed for 9 months cuz the world was shut down and like and I want to live there.
Do you plan to maybe go there one day, semi-retire? I know you're never going to retire. You're going to be like me and work forever because that's our purpose. But do you find that you will go back and forth and stay there a little bit longer?
Yeah. But I'm always like back and forth and traveling, right? There's like I have a huge network in New York, a huge network in the valley. So, it's just if I get a little bit of time where I can work remotely. It's very nice to work in a warm climate.
Oh, absolutely. And I think that is so important because I love when people talk about burnout and trying to like life work balance. I'm like, as an entrepreneur, what is that? There is no work life balance.
There is none of that. Which is why it like works really well when your partner is also an entrepreneur because they like deeply get it, right? Nothing blew up this weekend. Okay, we have the weekend to go away. But in every other scenario, you just have to roll with the punches completely.
100%. And so going back to the fact of being an entrepreneur, the uncertainty. So when you were younger, how'd you deal with that? Cuz a lot of people, there's generations that cannot deal with uncertainty and you just know and you see people that pitch and they need that structure. And God bless like fine but as an entrepreneur the one thing that's certain or the only thing that's certain is uncertainty. What do you think of that?
So I think it's just being honest like I had to unlearn that. And the good part is I became an entrepreneur right out of school. So I was whatever 21 years old, 20, 21, something like that. And you have to unlearn this. The problem is that like school and university teaches excellence and excellence is like amazing for science, right? And I'm an engineer at my core. So again, 90% is better than 80 is better than 70 is better than 60. And so there is a really important place in this world for excellence and creating something that's perfect. And like I'm a huge fan of like the Jiro Dreams of Sushi and the like crying when you make the perfect egg. Like we've lost a lot of the quest for excellence. But the problem is being a founder is not about excellence. It's about speed and moving and those are tradeoffs. And so you are actively trading something perfect for something fast. And fast doesn't mean sloppy, but it means that you are like executing as fast as you possibly can to get to market to test because you're trading the value of consumer data and feedback for something that's perfect. And I always describe it like this, like your perfect product. Have you ever been on the internet and you just like want to buy something?
And you've typed in your credit card like three times and you like yell at your phone. You're like, 'Take my credit card already. Like I want that.' That's what you need your product to be, something that people are willing to type in their credit card three times for because every other time you would have just like went to another window, totally forgot about it, abandoned cart, doesn't matter. You're aiming for a product that people would type in their credit card three times and that product, if you believe it or not, it probably doesn't have perfect photography, it might have a typo in there but fundamentally it's something that provides so much value to something, they can't help but buy it.
And so that's really where this comes into and really where people get confused is that this is trading excellence for speed. And part of the speed equation is that your life is a little uncertain because the other thing as a founder is it like all rolls up to you.
Oh, it sure does. Like CEO is chief everything officer. Like I love that.
It doesn't matter. I remember the day before like Groupon came to our office. We're like about to sell our company. We have like a toilet that doesn't work. I was like I guess this is my job. Like we have a huge team at this point. No one's there to do it. I was like I can't have our buyer, potential buyer, come to a dirty bathroom. Like this is my job.
Yeah. And I think when you have that scrappy mindset, when you really fundamentally believe that there aren't tasks below you, you're a much more incredible person to work for. And that's ultimately why like founders become like so cool at the end of the day because you always have the world taking a little strip off you reminding you.
Yeah. It gives you you're not perfect. Right.
Well, yeah. And you talk a lot about grit and you talk a lot about perfection. And I find that a lot of founders really want to get to whatever their perfect looks like. And my thing is like take action. Like movement is movement. I don't care if you're, you know, working behind the scenes, launching before it's perfect, not having everything in place because I think your why is so much more important than the how. Again, I'm not saying fly by the seat of your pants, although a lot of entrepreneurs do it and very successfully. Yeah. But I think for me, it's just learning that it's movement over perfection. Would you say that to be true?
Yeah. So, I would say that like even beyond movement, it's like iteration gives you innovation. It's actually like trying a lot of things and getting a lot of market feedback is what allows you to come up with something that's like incredible because most people get this wrong. Most people think because when entrepreneurs tell their PR stories, they only have a couple minutes. So they're like, I have this incredible idea and then this became a billion dollar idea. They don't have time to be like, I actually tried 11 things that didn't work and then we got to this, you know, incredible idea. And this is like truly every story, right? Like the Uber story is not like they came up with ride sharing. Like it was like they created an auto dialer for a black car company at the beginning, right? It's very important to realize that like that failure is a byproduct of success. And it's actually more than failure. It's like little lessons that are showing you what's going to be a big innovation.
I love that. And it's the same with rejection. I can't remember her name is not coming to me now, but the girl from Bumble, I think. And Canva, she was rejected I think 102 times. And my thing is is like get the rejection because to me two is a lot. I don't either. I'm saying rejection is redirection. But you talk about feedback. To me that feedback is worth its weight in gold. Would it not be? Because it's not always about knowing what you need to do. It's also finding out what doesn't work. That to me is equally as valuable.
First of all, 102 people rejecting it is not a lot. I feel like it's like thousands of people that reject an idea to be why do founders get so caught up when it's like well 10 people. You know how many founders I've talked to that they've given up on their dreams because they've gotten 10 or 110 nos. They give up on their dreams and I'm like pivot like that. That would be like a boxer saying I'm walking out of the ring because like someone took a swing at black eye.
Do you understand? Like fundamentally you're fighting like the force of history. Like most things are done in this world because we historically did them. Like at almost no point are the way we built roads or trains or technology when we looked at the vastness of knowledge and then we were like choose the right solution. Like we live the way we do because of largely historical reasons. And that is the entire reason that a startup can innovate because they can look at a space and be like wait a second we have this technology here and this technology here and those were invented at different times and we should rebuild something else right? Like we are going to rebuild our entire world with AI right now like it is all going to change so rapidly and so scary. I mean, your ability to generate to say, 'Let's put this chair as a render in my home' has gone from like a terrible photo that was worse than you can make in Photoshop to 8 months later something that the most expensive design studio in the world would do for you.
Yeah. Like that is going to transform every part of like art and work today. A lot of people were afraid of AI. You know, anybody, myself included, is it going to take away from the creatives? And I think no. I sort of think that it will add to what they can already do but they have to learn it not be afraid of it right? And do you think that that is going to be not only like coming in leaps and bounds but that is our future so many people talk about you know if you're not on the AI train now you're going to be left behind I already see it and I hate to say it but I'm the same way I'm like what did I do prior to this and I just asked my husband that and he's you spent a hell of a lot of time writing and organizing and right or having the team do it and now it's just it's just the time. So anyways, what what's your take on that?
Yeah, I mean it feels like super scary to get on the train. Yeah, it always does. Like just close your eyes and like imagine being a newspaper person. The newspaper is a really good example because newspapers had deflected a lot of innovation in the media space, right? Everyone's like, 'Oh, radio going to take over newspapers.' Didn't happen. Billboards going to take over newspapers. Didn't happen. And then finally social media. In fact, I would even say the first version of blogs. They didn't really touch newspapers either. No, it was really social media that dramatically changed what a newspaper is able to do and capable of. And their reach today is very, very different. And their reach without social media is just a fraction of what it used to be. So, look, I think there'll always be a need for humans. Like I was reading this incredible stat of they've just started to like make nano slices of the human brain and like the incredible millions of synapses and even this like nano slice is crazy. Like the brain is incredible. Our ability to be creative is incredible. And I always look at technology as like we are largely reducing the tasks that we never wanted to do in the first place.
I have never met a founder that's like I want to be an entrepreneur so I can do my accounting. Like said nobody ever. Nobody's like I want to be on the 50 person email chain about coordination. I want to be writing you know another bio or another job description. Like the fact that we've gotten rid of those tasks means that it's going to be so much easier for you to focus on how to create incredible marketing and an incredible product. And it's also going to be very uncharted waters because there used to be a competitive advantage in building technology. You used to be able to I mean pets.com was a million-dollar domain. To set up a website was another million bucks. There was a lot of work to start to compete with that. Now, as soon as someone's made a perfect product, you can go and say, 'Call that. Let's build this for me.' And so that's dramatically going to shift a founder's, you know, execution, their product, their IP, into that realm. And so I think it's going to be interesting. Look, innovation is scary. Change is scary for people, but I also think fear kills 100% of people's dreams, right? So, I think what you said, just jump in, have fun with heartbroken by these like women that you were like, they gave up on their dream cuz two people said they didn't like it. Like, most people won't like what you're building and they won't get it. And you can't see the future until you've actually built it. Like, we had no idea at Snapsave that people would take a photo of their receipt. This was like 2012. No one was taking a photo of text. No. That's so common now. You scan documents, you can close a billion dollar transaction over DocuSign on your phone, take a photo of a contract like that just didn't exist. And so you have to imagine that world. You have to be called stupid and then everyone's like, 'Oh, that was so obvious.' Yes. They never give you credit at the end. So obvious was so obvious. It was just whatever.
I know. I know. And so now you're saying go with the innovation and be open to learning. Yeah. But what would you say was one thing that really shaped you when you were younger? I mean, for me, it was always the rejection, people not believing that you could do it. Oh, you're a woman. Oh, you know, I'm sure they look, oh, she's cute and whatever. And you know, Madonna had this great video where she's like, you can be pretty but not too pretty. You can be smart, but don't be smarter than the man in the room. And I was kind of like, and anyways, everything she said was true. Did you ever have that?
I want to like pick up on that. So there are women videos about that and all of that is true, right? There's moments where it's like pretty, not too pretty, smart, not too smart, but there's never the male version of that.
You know, be strong, but don't be too like don't be too masculine. You know what I mean? Be like sensitive, but don't be like weak. Like I actually think that all of this stuff is in the nuance. And every time I see a video of a woman saying like here is the double standard, I actually think of like the incredible double standards males are now up to as well because like be the protector but like don't be too aggressive. You know what I mean? There's like so many dichotomies that males are stuck into. And so I really with any of these things I'm like very focused when I like see something that's very frustrating I like step back and I'm like this is not just me. This is everyone.
Okay. That's a different perspective and that's a good perspective.
I think it's a good perspective because you know I complained a lot about no one taking me seriously cuz I was young. Well you know the number of people that are old that people are like oh they can't learn technology. Truth. You have to always look at the opposite to see if you have something to really complain about. Like people are so busy with work. They hate work. And the unemployed would love to have a job. You work. There are so many people that would love to be famous and all that famous people want is privacy. Yeah. Like there is so many of people who have straight hair want curly hair. And this isn't really about what you don't have. This is actually about that no matter what position you are in, if you look around truly at everyone else in a position, there's no one that's got it perfect. And so that helps shape like my own mental ability to complain to myself because we spend a lot of time truly like self-loathing and was that misogynistic and like why did that happen? And I always choose to use the framework. I mean, I literally just had something happen to him yesterday and my friend was like, 'Oh, I just think he's being such an a**hole to you.' And then I was like, 'You know what?' Or he's extremely stressed out and he's got a company in a shape that needs to be fixed and something that happened caused a lot of new headaches.
So, you kind of flipped the script on as opposed to complaining about it, you were going to see other people's perspective. And, you know, regardless, the benefit of the doubt.
Yeah. And I think just be a kind human. And my thing is regardless of gender. Like I try never to let gender play into anything I do personally or professionally. But you know your example exactly like I've walked into a boardroom with 19 white men that were like this and they're on their phone and it was like okay are we done yet? And I'm like well I'll just turn the PowerPoint off that you asked me to create. Let's have the conversation. And then it turned to like and I heard you talk about this jacket and I want you to kind of share that story in a minute too. And it was like, well, how will you afford it? And my answer was, I'll sell one of my LV purses. It'll be fine. And they just went, oh, cuz do people ever ask men how will you afford it? Or other I just think there's certain questions that are sort of offside. Let's I want to far off side but you listen to real locker room talk men are to other men like there is a culture of like constant digs between guys that most men never talk about how like difficult they are right so I'm always like hm am I being picked on or is this guy just like having the worst ever I really try and give people the benefit of the doubt by but also like empowering the people in the system that I like because I don't want to be a part of like, oh, okay, there's just 19 white males at this boardroom and they have no interest in what I'm going to say. Like, that doesn't make sense. Okay, story of the jacket.
Yeah. No, I loved that story. You have to share.
I think the jacket is so funny. So, I didn't know anything about leather jackets. There's a 1990s designer that's called Michael Hoben that's really famous that makes these jackets. And we were vintage shopping and I was like, 'Oh, I love that jacket.' Like the color, everything is fantastic. Um it's very the wings. Yeah, the wings, all of it. I have feather tattoos. So, yeah, as soon as I saw that, I'm like, yeah. Um anyway, so I was like, 'Hey, can I try on that jacket?' And the guy that owns the vintage store looks at me and he goes, 'Well, you can't afford this.' I'm like, 'Pretty sure you obviously has no idea who I am. I probably look like a bum out loud.' And I was like, 'How much is this jacket?' And he's like, 'Oh, it's like a Michael Hoben original. They're like $800.' And I was like, I think like why don't you just let me try it on?
You're like, yes, please. I just paid five grand for another one. I'm good.
So, he literally just he was like begrudgingly, let me put this jacket on. And then I just looked at him and I was like, I'll take it. And I just paid him in $100 bills.
Uh, that a girl. Come here. You got to give me five for that. Anyway, but you have to like again I think especially for women where it's so easy to like get your head in a negative mind frame. It's like shifting your perspective. Right.
Again, the other framing you can use for this is would you prefer to be overestimated or underestimated?
Oh, didn't we have this? We just played this and that on breakfast television. Was that one of the questions?
Yeah, I think so. We did just talk about this on breakfast television. Most women complain because they are underestimated.
So they're like, you know, people thought I was the secretary. People like didn't think that do anything.
Can I speak to your boss?
Can I speak to your boss? All of that. Uhhuh. But that puts you in such a position of power because people have already given you like their expectations of you are zero. So performing at a 10 is like insane. Performing at a hundred is like mammoth and performing at a thousand like people will never forget you for the rest of your life.
