From Perfectionist to Powerhouse: Michele Romanow’s Blueprint for Entrepreneurial Success

I think there's a lot of truth to successful people do what unsuccessful people were not willing to do. You had to launch quicker and what you were going to do is you were going to sacrifice some perfection for speed and in the startup world that was always a trade-off that you should be making because if you're not moving that fast your competitors were moving that fast and they're capturing market share away from you. And even in small business it's better to launch something that might not be perfect, see if people like it and if they like it, perfect it. Become an entrepreneur is to just be an entrepreneur. Like there is no amount of school and studying that teaches you how to be a founder. You just have to do it and learn very very quickly.

Oh, it's wonderful to be here.

You know, I think I had a really wonderful childhood. I had two parents that loved me a ton. And I was one of four kids. I was the oldest. And I think there were a couple of very key things that they did for me. I think they let my learning expand at my speed. And so they were constantly pushing me to do new things and better things. I remember in grade six it was like, 'Okay, and now we read The Economist.' And I was like, 'No kid reads The Economist.' And I was, 'No, no, you should read it and you can highlight the things you don't understand and we'll talk about them at dinner.' We played a lot of what we called parlor games where we'd ask everyone one question at dinner and then you had to answer it and it could be as fun as what would your secret superpower be or if you were in charge of fixing Canada what are the three things you'd do tomorrow. And I think that really spurred a lot of really intelligent thinking and curiosity from a very young age. And then you know, my dad grew up in a two-bedroom farmhouse without a bathroom in northern Saskatchewan. My mom was a Slovak immigrant, came to Canada when she was 13 years old. And I think at the end of the day, my parents were just really hardworking people. I was born in Calgary, spent six years of my childhood in Regina and I just grew up with a lot of people who were really down to earth and worked really hard. I think when you're around people that are farmers all the time, everyone understands, if you don't wake up every single morning at 6 a.m., you lose the animals or you lose the crops. And I think that gave me a lot of perspective on how to do things. And I get asked today sometimes, 'You're so down to earth.' And I'm like, 'I don't think I ever left Earth.' Right? I think in my life, I always think of, there could be two different turns and my whole life could have unfolded so differently. And I think it's the perspective of who you grew up around and appreciating that.

Yeah, I think that one specifically is like get messy, figure it out yourself, be scrappy. There was this huge, I think my dad had three girls and then a boy and so he kind of treated me as the firstborn daughter as kind of the firstborn son. I grew up in an environment where I got to do everything. I mean, we changed the tires. I know how to change tires on a car. I know how to fill up tire pressure. I knew how to check the oil. It was never a question of, oh, these are things that boys did and these are things that girls did. And I think that gave me a lot of confidence in my ability to learn things. Confidence to get my hands dirty in doing things. And that has served me so well in my career. I mean, I think that most people who haven't been CEOs don't understand that CEO stands for chief everything officer. At the end of the day, it all rolls up to you, especially if you're a small business owner. And I have had to do things that are remarkably unglamorous throughout my whole career beyond even when I had a public profile. Right before we had Groupon visiting our offices, this was going to be an epic deal if we could sell our tech company at 28 years old to a large publicly traded American tech giant at the time. And I remember our toilets were clogged. And I was like, 'Okay, well, I have to solve this because we can't have our buyers show up and have them not be able to go to the washroom when it's 11:00 at night.' And so, there I was figuring out how to get these toilets to work again. And I think there's a lot of truth to successful people do what unsuccessful people were not willing to do. And just that ability to be hands-on, be willing to be scrappy, get your hands dirty has been so important. I think one of the other things my dad taught me was this idea that you should always question and not really believe in stupid rules. And I mean, you have to do this within reason, obviously, or else you're going to have a much different problem on your hands. But I remember my dad was lucky enough to go into air cadets as a kid. And so he was a pilot and we would go on airplanes. I remember my first airplane. I was in grade two. And then, when the plane is going down, they always say, 'Okay, put your tray table off.' And my dad would always do work on the plane. And so he had all these papers out and was marking things up. And then the flight attendant walked in like, 'Oh, you have to put your tray table up.' And every time he would put his tray table up and then she'd walk away and he'd put his tray table back down and keep working. And I was like, 'Dad, you can't do that.' And he would just look at me and say, 'You know, Michelle, I'm a pilot. If this plane goes down, this tray table is not going to make a shred of difference. And you don't have to believe in stupid rules.' And obviously he was not going to get into a fight with the airline over this if they asked again and again. But there was this constant push to be like, why is this a rule? Is this a real rule? Should this be re-examined? And that I think is one of the mindsets that allows you to reexamine an entire industry.

Yeah. So let's start with how I got to this perfection point. I think it's a little bit more of a female trait. I think I was able to do really well in school and I had a huge desire. Like I remember coming home from grade seven and I was like I want to write the best book report not in the class this year. I want to write the best book report that this teacher has ever seen in her career. Like what possessed me to think about that? I don't know. I think at that point some of this is just genetic, right? My parents were amazing and they pushed me and they had very high standards, but I had an enormous amount of drive as a kid and I had an enormous amount of drive to be very good at things. And I played piano and I did all sorts of extracurricular activities and so that really fostered things. And then I remember moving schools in grade seven and I had gone, this is a really important dynamic that I don't think people pay enough attention to with kids. So when I had left my old school I was one of three friends and I was the dumbest friend. One of the girls was Asian played piano. She had started five years earlier than I did. She was amazing. She became a doctor. My other friend could read a book with 500 pages, I mean we're in like grade five or something and she would just crush this whole book and I just knew that of the three of them I was the dumbest friend and so your whole world order is three people and so you're at the bottom of that stack. And I remember moving schools and I moved to this Calgary school and I was so conscientious of how I was going to do, what my grades were going to be. And then I remember getting my first report card and my teacher comes up and she goes you have the highest average in the whole class and I was like that's impossible I'm not that smart because I'm the dumbest in three friends. And it was a huge turning point for me because I realized if I worked hard I could be really good at something. And I think then school unfortunately fosters and rewards perfectionism, right? It's literally a system where 100 is better than 90 is better than 80%. And so obviously was rewarded through the whole educational system with scholarships and all sorts of things for getting very high marks. I think the perfection system works well in some careers and it certainly works well in things like research where most of our big scientific discoveries were a result of a lot of trial and error. And so, how did I go from being kind of a perfectionist student into learning that that wasn't the way? I think it was some of my startup education. It was realizing that you had to launch quicker. And what you were going to do is you were going to sacrifice some perfection for speed. And in the startup world, that was always a trade-off that you should be making because if you're not moving that fast, your competitor is moving that fast and they're capturing market share away from you. And even in small business, it's better to launch something that might not be perfect, see if people like it, and if they like it, perfect it versus taking all this time to make things perfect. And so I talk a lot about how I had to unlearn my habit of perfection. How I had to be okay with, if I was going to be a CEO and pick up my phone 30 minutes later and have 25 messages of people that needed me uniquely to respond that there was going to be typos and it was going to be quick decisions and some of this idea that you should be making reversible decisions very fast and irreversible decisions very slow.

And that became the 70% factor. And I talk to a lot of other founders about how they figured this out and their journey. And because most people don't know unless you've been a founder how much failure there is before you get to success. Like it's just an enormous amount of it. It's 80% of the time you're failing.

Yeah, that's about right. And when you fundraise that's about the right number is you have to prepare yourself for an actual 99 nos. Most people are not prepared for that. And these are very sophisticated nos from very smart people. And so just being able to endure that, being able to take some of that advice, being able to pivot and grow your business, it's just a lot.

Yeah, for sure. I couldn't agree more. There's a deadline. I mean, journalists know this, too, right? It's got to go out and there's that same pressure in the social media calendar day. It's just got to go out. And so, I think that that also just forces you, timelines force you to be better. One of my favorite lines is work expands or contracts given the amount of time you have for it.

I mean, try four things this week. Literally just try four things. You're like, I have a product I want to try. I have a pricing strategy I want to try and I need to fire a person. Those are probably the biggest ones to do. Every single one of us has a person on our team that's dragging everyone down. And it's not the right fit and it's really scary and we always drag our feet for too long. There is always a new product that you can try or you can ask your customers if they want to try. And pricing is a remarkable lever in most businesses and most people are really scared to change something and everyone's going to complain but if they don't stop buying that means they're okay with it. So that would be what I would challenge you to do. I would also just challenge you. I think this is constantly a thing for me. I was actually showing you my handwriting. I constantly force myself to sit down with just a pen and a piece of paper and I'm like, if I only do three things today, what are the three things that matter? Just what are the three things that matter? And that is remarkable in terms of, we do a lot of things that are like getting back to people and little tasks. There's really three things that probably move the needle on your business. And if you focus on doing those, it's going to have way more leverage than all of your little tasks.

Well, because we get distracted with so many things, right? Our phones are work devices, but they're giant distraction devices. There's just so much that happens. There are just a couple things and a couple people that will change the lever. You make one great hire that might change the course of your entire business. You close one big partnership that might change the course of your entire big business. You secure one big client, like following up on the things that matter and not focusing on what doesn't matter. And here's the remarkable thing. If you just start your day with doing the three hardest things, the rest just the momentum just takes over. And so I love the strategy on a post-it. We're just doing one thing. And again, you should have these strong beliefs that are loosely held. So, here's your posted strategies today, but I can still be challenged if that's not working. I'm happy to change it again. But I do have conviction that we are trying this today because if you have a bunch of weak conviction points, you'll actually never figure out what works anyways.

I didn't know that. But yes, I love lists. I love structure. I can visually remember what I wrote on lists. And reorganizing notes somehow, especially on to-do list. Like I end the day, I have a piece of paper on what I need to do the next day. Like that is how you get things done. You do not get things done or at least I cannot get things done by just randomly sitting in my computer. I mean I have 140 tabs open right now. Like if I just go into that mess of every project I have been thinking about it's not going to end well for me.

Of course.

Yeah. So, I studied engineering because my parents told me I could study anything as long as it was engineering. Quickly figured out I was going to be much better at building businesses versus bridges. I was an environmentalist and really thought why don't you take a simple business like coffee and see if you can make it zero waste and took two years and opened the tea room on the Queen's campus which was a little coffee shop where everything was zero waste and it's still around and run by students today which I think is such a cool story nearly 17 years later. So that was my first business, that was my first time hiring people. That was my first time managing people and you learn a lot and even some of the challenges I had at Clearco, I could relate back to some of the challenges I had at the T-room in the early days. So, the best way to become an entrepreneur is to just be an entrepreneur. Like there is no amount of school and studying that teaches you how to be a founder. You just have to do it and you learn very very quickly.