What I Know Now is an interview series in conversation with entrepreneurs about the failures and successes of their careers.
Michele Romanow seems to have it all. At only 33-years-old she’s already founded five companies, of which her current company Clearbanc is worth $70M, and she’s the youngest entrepreneur to ever star on Dragons' Den.
It’s no surprise that when you set aside Romanow’s achievements, she’s like any other entrepreneur: her success hasn’t come easy. She’s failed. She’s had dark days. She’s had to get up every day and put one foot in front of the other and try again.
Her success is grounded on something much deeper than a smiling face: resilience—she’s true to herself, and in doing so, she goes against the grain of what many people believe are successful traits of an entrepreneur. For example, she’s not a morning person and her yardstick for success has nothing to do with making more money or building more companies. Her measurement comes down to whether she’s growing as a person.
She commends the community of people she grew up with in Regina, Saskatchewan, the “salt-of-the-earth kind” as she tells YouInc, for building her work ethic. In this first interview of our new series she said, “people can’t run into their first obstacle and say, ‘well, I can’t do it.’ You have to remember that every story was pretty much a disaster the whole way until it got to the end.” We discuss why she’s so honest about the hardships of entrepreneurship, how she learned the importance of sleep, and how she measures success:
YouInc: You grew up in Regina, a small rural place that many Canadians probably haven’t visited. What was it like growing up there?
Michele Romanow: It was such a rich, warm, and small town childhood. I lived two blocks away from my school. I got to go to all the dance and piano classes, because everything was a 10-minute drive.
There’s something about folks from the farm, because Regina and all of Saskatchewan is basically a farming community. So, even if you live in the city, you're still connected. They're salt-of-the-earth, hardworking people. The reality of owning a farm is that every day you have to get up at 6 a.m. to feed your animals; if you’re sick, if you’re not sick, if it’s raining, if the sun is out...I think there was this really down-to-earth hard work that was instilled in me from that upbringing.
YI: What has helped you get where you are today?
MR: I think it's a couple things. The first is that I was willing to get scrappy. I believe that CEO stands for Chief Everything Officer, and successful people do what unsuccessful people weren't willing to do.
All the planning in the world wouldn't make me successful and wouldn't prevent me from failure.
The first business I started was a caviar fishery. We were literally catching these fish, processing these fish, and calling these restaurants saying, "We have this product that hasn’t been available for years.” And people were excited about it. The supply chain part was not glamorous—you have to do whatever it takes to lift the business off the ground, which is an enormous amount of energy.
The second thing that made me successful is that I needed to stop planning and get going—all the planning in the world wouldn't make me successful and wouldn't prevent me from failure. I had been a good student in school. One of the problems is our academic system; it’s really hard to teach entrepreneurship, because it teaches excellence, right? One hundred per cent is better than 90 per cent, is better than 80 per cent. The reality of being an entrepreneur is you need to be executing three times faster than any of your peers, but at like 65 to 75 per cent. I came from a place where you're constantly planning; I had to learn that this is a game of 95 per cent execution and five per cent planning.
Then probably the last thing is that all of those iterations and experiments and massive failures will end up leading to a big innovation. I think innovation is a lot of iteration. Most people don't realize this, right? Most people think innovation is dreaming up a big idea and going for it and suddenly you build Uber and it's worth $70B. It never happens like that. Even the first version of that app was incredibly simple and matched you with a black car service. It had a little bit of location, but it was very rudimentary.
I focused on being willing to do whatever it takes, and focusing myself and my team on the execution of running the service. We were learning everything that was working, drawing off of that and settling down a bit.
YI: It seems like we’re trying to be too perfect all the time. What's our problem with iterating?
MR: Perfect is the enemy of good. As a startup, your most important advantage you have is speed. The reality is that every big company can do whatever you're doing better, with more resources and with more capital. But, they actually can't do those fast, because they have a world of internal politics to deal with. So, speed becomes incredibly important, but being fast means you can’t be perfect. There are a lot of great tech entrepreneurs that say, "If you've launched and you're not embarrassed about your first product, you haven't launched fast enough." The reality is, when you have a great product, people don't think about silly mistakes. They're like, "This is so cool, I'm gonna buy it anyway."
To be an entrepreneur you have to be kind of delusional, kind of in love with your idea. You also need to know when it's not working.
TappLock was one of my deals from Dragons' Den, and they put a fingerprint sensor on a conventional combination padlock. Despite the challenges they’ve had growing, it was a better product. People were like, "Okay, this is fantastic." It means first that you have to be fast.
The second thing is that you have to throw away a lot of ideas that aren’t working. When we started SnapSaves, we started different iterations on how to build a company that digitized consumer-packaged goods coupons. We had a print-at-home website. We had a subscription box company. We had all sorts of things, until we got to the app that we did. We would try something to see if it worked. We would test it with $10,000 and three months of work—if it didn’t work, we didn't have an ego about saying, "This isn't working. We need to try the next thing." It's one of the big problems: to be an entrepreneur you have to be kind of delusional, kind of in love with your idea. You also need to know when it's not working, how to listen to the market, and how to keep iterating.
YI: There are so many pressures placed on entrepreneurs: be a morning person, operate on little to no sleep, start a side hustle. How do these pressures make you feel?
MR: One of my most memorable life experiences is when I dated two different doctors, totally unrelated at different periods in my life. Both of them had gone to med school for almost nine years and had access to all sorts of drugs in the hospital that the general population wouldn't get access to. When they felt like they were getting sick, they would put blackout blinds in their room and they’d sleep for 12 to 14 hours. It was one of the most memorable, personal moments in my life. I'm like, "Okay, you go to med school for 9 years and when you think you're getting sick, the only thing you do is sleep." [laughs] That's an extraordinary insight.
One of the things I try to do when I feel like I'm getting sick is get a giant amount of sleep; it works most of the time. Let's be honest, if you're an entrepreneur there are periods in the year, where you’ll have to sprint; if you’re closing a massive transaction, if you’re launching a brand new product, those will be the sprint periods. You won’t have time to have dinner with your friends, and go to birthday parties, and do social things, and enjoy warm weather. You will have to focus entirely on executing that part of your business.
I read a lot of stories of other entrepreneurs, because they constantly remind me that everything I'm doing, even today, is normal.
Unfortunately, you don't always know the times that you will need to sprint. I think it's really important that you communicate with your team. When you need to sprint, your team needs to sprint. But then there are other times during the year that you don't need to sprint; it’s like tiring yourself out for no reason. And so you need to use those other periods to let you and your employees do all the things that maintain your life. I certainly learned to sleep. I could definitely function if I needed to, on a little sleep, but for a small stint.
I'm not a morning person. I have tried every technique to make myself a morning person, because there’s an extraordinary bias in this world that morning people are more effective and more productive than night people. I think this is one of the most basic genetic instincts that people are born with.
For me, I'm as alive as I can be at 11 o'clock. I’m ready to do work. My brain is firing on all cylinders. In the morning, if I have to do a breakfast meeting, I'm not in great shape. So you have be okay listening to your own body. Productivity is about doing work when your brain is working, when you're ready to do that work. This constant need to force people into one or the other is unhelpful.
Getting good work done is having uninterrupted periods where you can think and create, and you can synthesize your own ideas. And so, if you do that at 6 a.m. all the power to you, if you do that at 1 a.m., all the power to you. You have to find that time, because without that, you tend to focus on shallow things, and quick turn tasks, which is not how you get something big done.
YI: You're honest and open about the difficulties of being an entrepreneur. Why have you chosen to talk about the hardships?
MR: It does you no benefit [not to]. I believe in radical candor. It’s a part of my company culture, too. I'll give you an example. You hire someone, everyone's like "you're doing a great job, you're doing a great job." Then one day, that person is not doing a good job, and no one's telling them the truth. So, someone walks into the office and says, "We gotta fire you because of this, because of this, because of this." That person looks at you, and says "I never knew." There’s so much unproductivity from every angle of that.
It’s so much harder to tell the truth. Everyone can pretend something's okay, everyone can ignore something and focus on something else. It's actually a lot of work to figure out the words to use, the framing to use, and be honest with somebody. I believe anyone can be an entrepreneur. It’s not one of those professions that you need to have a certain academic background or a certain skill set. You need to care about challenging the status quo, and you need to love building.
Being an entrepreneur means constantly being in the business of making low-probability events become high-probability events.
Telling people that it's so easy, and that they can do it, too, is a total misnomer. It's a total lie. This is going to be hard, but hard things are worth doing. Because entrepreneurs have the most amount of power, and the most amount of impact in this world. Look at the billions, if not trillions of dollars that the world government has spent on climate change and environmental initiatives. Everything meaningful we will do in terms of electric cars will have come from one entrepreneur: Elon Musk.
That to me should be extraordinary. You can actually do that as an entrepreneur. That's a bigger impact than I think most world governments have had trying to tackle the same initiative. So, there's a big prize, if you get it right as an entrepreneur.
That doesn't mean it's easy; you're fighting the stream on absolutely everything. You have to go from zero to one, which means you literally have to build something. Being an entrepreneur means constantly being in the business of making low-probability events become high-probability events. I think it does a disservice to not talk about trouble.
Buytopia was self-funded, and we were in an ultra competitive space. I remember thinking, "there’s no way I can replace myself. I can't leave this company, because this is everything I've worked for." Then I got sick that year with whooping cough. It was the dark period. It's okay, because it reminds people that humans are extraordinarily tough. We don't talk enough about how tough we are. We sometimes need to be reminded that we have all of that within us.
So then I think, what are the techniques for actually reminding you? It’s finding people that are willing to share their true, unvarnished story about how hard it is. I read a lot of stories of other entrepreneurs, because they constantly remind me that everything I'm doing, even today, is normal. Then I think you figure out how to surround yourself with other entrepreneurs you know and trust.
I'm careful who I share my early ideas with. I share them, for the most part, with other entrepreneurs; only with people that have constantly been making low probability, high probability events. Because what you need to hear is not all the ways that this can go wrong: you need to remember what are the levers that you can use to make this low-probability event become a high-probability event. The only people that know how to do that are entrepreneurs who have consistently found that throughout their career.
I was literally at that point, where I was like, "just going to live another day. We're going to do one more day of this."
YI: How did you get out of that dark period of your life?
MR: Surrounding myself with a circle of entrepreneurs. My business partner Anatoliy was the most important; we looked at each other and we were like, "We can do it. We can live another day." Then there was a period where I needed to do one day at a time. I'm gonna show up today, and I'm going to do whatever I can to make this a better business for tomorrow. I was literally at that point, where I was like, "just going to live another day. We're going to do one more day of this."
Then you try enough things, and you catch a break. You're so grateful for whatever shifted in the market, or your business, or your people, or all the things. It was remembering that I wasn't alone, and that other entrepreneurs were going through the same thing. It was having great business partners, and it was also reading the stories.
YI: How do you measure success?
MR: If I was to think of a motto for me, it's “never be comfortable.” As soon as you're comfortable, you stop growing. As soon as you push yourself out of your comfort zone, it's scary for a second, it's terrifying for another second, and then you're trying to make it, and then it's absolutely exhilarating and thrilling—you've grown a new skill set, a new set of ideas, and a new thing that you feel confident in doing. I find that process really rewarding, because it starts off as fear, and then gets into something real.
So, I don't think I have a single yardstick for success; it's a combination of, "is what I'm doing having the impact I want it to have? Are we making a difference in the lives of my team, and the customers?" It's more about am I constantly growing as a person? Which is a better way to think of all that.