Michelle Zatlyn wants you to check your assumptions & never let a crisis go to waste

Welcome to Canada's podcast. So, Michelle, great to see you. Second time I've seen you this week. I saw you at Collision as well, but that, that's fine. But for everyone, you know, so listen to Canada Podcast. Why don't you tell us a little bit about yourself and, you know, your entrepreneurial journey from like Saskatchewan to McGill to, to Harvard, the president of Cloudflare and the Silicon Valley thing. Give everyone kind of a quick 2 or 3 minute this is Michelle kind of thing.

Okay, happy to do that and thanks so much for having me and I hope next time it's twice in person, Philip, because zoom is wonderful, but there's no people in person and I do miss that. So hopefully we can do that next time I'm in Toronto. Thanks so much for having me and it has been a very positive journey. I grew up in Saskatchewan and very proud prairie girl. And then I went to school at McGill and love that and found myself working in Toronto for many years and have many friends and met my now husband there and ended up going to Harvard Business School. And the way that that all happened is I went to undergraduate to study science thinking I wanted to be a doctor. I really loved medicine and science and I ended up falling in love with technology. And there's a lot of twists and turns on how that happened and I'll save that for another day, but I think that that story of I thought I wanted to be a doctor, but then I fell in love with technology, or maybe I thought I was going to be an accountant and I fell in love with technology, something that resonates with a lot of people. So I wanted to bring that up for your listeners because I that I just kind of happened to fall in love with technology. I had met, I started to work at a technology startup in Toronto way back when, and that's when it kind of opened my eyes to what was possible with the team. And so I was working in technology, I loved it. And I just realized that I had a science background, I had a technical background, and I missed some of the business foundations. And I really realized that I liked working in business and growing teams, but I felt like I lacked some of the toolkit. And so that's why I went back to do my mba. And I think anytime in life when I try and sign up to do something, I try and do it the best I can. And so I ended up applying to a lot of great schools, both Canadian and the U.S. and I ended up getting accepted to Harvard Business School. And that's what took Me to my journey first journey down to the US As I moved to Boston to go to pursue my MBA at Harvard. And that was just an amazing eye opening experience. I had at this point lived my whole career up in Canada and I loved it. Just arriving on the campus of Harvard and just being on a global stage. It's a very international school, a very diverse group of students with many different backgrounds. It opened my eyes on what was possible. And then, long story short, while I was at hbs, I was very curious. I wanted to learn, I was taking it all in. A classmate and I were on a school trip to Silicon Valley and I signed up through the trip just to learn more about Silicon Valley. I'd read about it, listened to it on podcasts like yours, and I wanted to go see it in real life. Life, like go see it in person. And there was a professor led trip to the Valley. This was back in January of 2009 and the world was not a very good place back in 2000, January 2009, it had been post the financial crisis. It was gloomy everywhere.

It was pretty tough, I remember.

Yeah, it was tough. And, and so I, we kind of showed up for this week long program in the Valley and we're meeting early stage entrepreneurs, late stage entrepreneurs, we're meeting venture capitalists. And again, as somebody who started my story in Saskatchewan, just meeting these people in real life that I'd read about, I remember like Jim Breyer and Mark Pincus and Zynga was the hot company at the time. And just meeting them and getting, being in the same room, I thought, oh my goodness. And it was on that trip that it almost demystified what being an entrepreneur was for me. And there was some early stage entrepreneurs that we went to here, listen to their ideas, and I kind of walked out of that room saying, oh my God, it was a light bulb went out. I was like, if these people can start companies, so could I. And that was a really empowering moment for me. And I happened to say that to a classmate on my trip and in what was probably the best answer ever, his name was Matthew Prince. Matthew said, of course you could, Michelle. And we literally started to brainstorm an idea in the hallway. We knew each other from school and that idea turned into a school project, that school project turned into what is now Cloudflare. And I don't know, I guess the, the moral of the story is being curious, being open to opportunities and there's so many interesting people in the world and, and hard problems that need to be solved. And I feel really lucky that I've met a great business partner in Matthew Prince to, to help solve our problem. And now today I've taken that idea to a company that's public with a lot of customers and a lot of employees around the world.

Yeah, I mean, you know, for those that don't know, I mean, Cloudflare, you, you, you know, you, you're being very, very polite about it. But you know, I think the last time I looked at that, a mid 40 billion market cap. So you, you've. You, you guys have done pretty well in the, the 11 years you've been running it. But you know, in, in that sort of 11 years, you know, building. Building something. You know, what's been the most exciting thing for you about being an entrepreneur versus, you know, see seeing others around you, you know, in the Valley, whatever the. That are, you know, senior executives that aren't in, that aren't a founder that aren't. That didn't create nothing. There's anything wrong with that. We got to have people all around us, you know, but for you, what, what's the most exciting thing about. You found about that entrepreneurial journey?

Basically, you know, so it's interesting. The most exciting thing is a little bit of a. I don't think you need to be a founder to have. It is. It feels really good to be on a team when you're working on a common goal and delivering on it and doing things. Turns out doing things that you're really proud of is incredibly empowering. And in many ways that's kind of what entrepreneurship is. You have an idea and you have to go assemble resources that aren't really in your control to build some things. You're builders and you're building something and hopefully you're building something of value because if you do, then it just kind of becomes a flywheel that builds on top of each other and you get to meet incredible people along the way. You get to help solve customers problems. And I just, there's. There's something very empowering about that. And I just think that's why I love technology is it's. You actually don't need a very big team to, to, to get that rush of I'm going to build something, ship something, and then see the value it creates. And I think that that is very humbling and energizing and inspiring. And so that's what I love about entrepreneurship. And what I would say is just to kind of punch up what you're saying is I actually don't think you have to start the company to be part of that. Of course, I happen to be the founder and that's amazing. But the best part of my job, hands down, are the people I get to work with. And then the second best part of my job are our customers. I love that too. But just very passionate, smart people who do a lot of different things, who choose to spend their time helping us make the Internet f safer, more reliable together is really fun. It's kind of like being on a professional sports team where there's lots of different positions and, and practicing and working together and then going to win the championship. I, there's a lot of that in the workforce, in a, in the work setting for me. And I think building companies, being part of a growth company, you really see the impact of your contributions. And I just think that's a huge feedback loop that's really empowering for a lot of people, including me. And so I think, I love that the best about entrepreneurship and I happen to have been also the found. But actually you can get a lot of that going to any growth company without having to be the founder. And so I think it's, that's the best part in my, in my point of view.

So you spent 11 years building this, you know, and it's, it hasn't all been smooth, I'm sure. What's the greatest challenge you faced in, you know, in, in those 11 years? I mean, it's always interesting for people to understand, but not just faced it that you've overcome and is there something that we can learn from that?

Basically, definitely. You know, I'm here smiling, all excited and on the balance, it's been incredible and I'm incredibly lucky. But it's certainly not always easy. And there are many times if we had met on maybe a few hours earlier, a few hours later, that maybe I'd be like, oh, it's been a tough, tough hour, tough day. And I think that, I think that there's more people willing to talk about that today, which is good. I just think that's really helpful because if you are starting a company or you're joining an early stage company, what I would say is the roller coaster. There's a huge roller coaster. There are many highs and lows and they're very close together. And that doesn't just last for a month. It's kind of like the first two to five years of the company's history as a roller coaster. And I just remember back, I think back to the early days of Cloudflare is, you know, you're right. We graduated from Harvard Business School. We packed our things in a U Haul. Matthew Prince and his mother drove the U Haul from Boston to California. I happened to fly and to drive my car from Vancouver down here. So anyhow. And we show up, and I look around at my other friends who I'd met at business school who now were getting signing bonuses to go work at companies, they were getting a good salary. We kind of show up in a city where we didn't really know anybody with an idea. We weren't taking a salary. We really did not have a lot of money in the bank. We just finished business school. It was hard. And so you're kind of looking around being like, is this the right thing to do? And I think early on, it's not that you wake up with someone saying, yeah, this is the right thing you should be doing. You gotta find the conviction from within. And that's hard to find that conviction from within. Actually, I think a lot of people choose not to do things because they can't do that. And so you're like, am I crazy? Or is there something here? And you go from one hour of like, oh, my God, this is going to be a huge company, we've got it, to oh, my goodness, am I crazy? Am I just delusional? And you go back and forth, highs and lows, very quickly like that. And to put it a couple years later, again, it doesn't start for one quarter. It's many, many, many years. You go from a team where you're trying to get people to come join you, and they do, and they're doing great work, and then they leave because of. Maybe they're moving back somewhere else or they decide to do something else. And. And then you have to. So you're like, oh, my God, you're leaving. That's too bad. To then having to get on the phone to convince someone else to join. I mean, five minutes apart. And it's these highs and lows that are very close together that I think is difficult part of entrepreneurship and being part of a growth company. And I think that's both for the founder, but any person working at that company. Because companies are groups of people working towards a common goal. And often a company with less than 500 people, you really know the others. And you're part of this. You're in it together, you're building. And so it's not just the founder. It's like even working there, you're like, oh, my God, my friend is leaving. Do they know something I don't. Or, oh, we lost this customer, or we won this customer. So it's both good and bad, very close together. And I think managing that roller coaster is an art and a science. And I saw someone say it was actually Fred Wilson originally, who kind of from Union Square Ventures, a really successful venture fund out of New York City. He blogs every day. He's kind of one of these famous people in technology who I used to read every day. And then years later, he ended up becoming an investor. So now I know him, which is kind of like this thing where you do something long enough, you end up knowing people. And I remember he used to blog about these emergency drills really close together, the highs and lows. And that your job as a leader at these growth companies, either as a founder or a VP or a C level executive who comes in, is to spread them out, because really great companies don't have those highs and lows so close together. And that was, and I think that that was a good mental model for me early on. I remember reading that when I was like 50 people and I was like, oh, my God, yes, we are the, the highs and lows 10 times a day. And really this idea of you got to spread it out and we still have great highs at Cloudflare. We win a big deal. We, you know, we, we, we, we, we ship some big products. That feels awesome. And sure, there's things that go bad too, but they're much more spread out now, so they're easier to manage. And so I think that's probably the best articulation that I can. That's kind of what's been hard. And they're for sure hard. We're a huge success story. As you said, we. On the positive, everyone sees Cloudflare as a huge success story. And even in the success stories, there's a lot of hardships and challenges you have to overcome, but with the right people, the right attitude, you can definitely do it.

So, you know, mentorship is so important. You've talked a little bit about it. What's the best piece of advice you've received that you keep on using? You know, you get advice and it's good at the time, but you. Then it disappears. But occasionally you have a mentor that drops something on you and you keep going back to it and using it time and time again. Anything like that on your front?

I do, I kind of three, and they're a little bit related, so I'll go through them quickly. The first is because from when I was a product manager toshiba Check your assumptions. It's actually people make really bad decisions if they use the wrong assumptions. You have to check, check, check all your assumptions. And I just. Whether we were 10 people or today we're 1800 people around the world. Check your assumptions. That piece of advice is so helpful. And if you understand the assumptions inputs, you can make better decisions and output. And so that's one. The second one is never let a crisis go to waste. And this is very helpful. Back to the highs and lows of building a business.

That's a very good one. I like that one. Yeah, for sure.

Because you think everything is going wrong and. Oh. And actually that becomes a huge lever to help change something in an organization or to say, oh my God, we're doing this wrong. We got to change it. And so I think that we've learned over the years not to let a crisis go to waste. So you build a product that no one uses. Oh my goodness. Use that to then go build the next great product or you lose a big customer. That does not feel good. That feels a huge gut in the punch. But okay, well, let's use why they left as a reason to fix it in the organization. And it turns out how. Don't hide from those. Be honest about it and don't let a crisis go to waste. It actually can help be the change agent you need as a leader with an organization to set the company on a better path. And I think that that is a very important lesson I've learned that I learned from, you know, a mentor and something that I still find myself today. And I know that's successful when people on our team say, Michelle, I remember once you told me never to let a crisis go to waste. And so I'm using that here. And you're right, it works really well. And it's, you know, it's. It's just a very.

I think that that's a really good one.

People can use that, I think in many, in many of their careers. Okay.

Just two or three what I call rapid fire questions. It's kind of fun questions really. Are you a morning or a night person?

A morning.

You know, 85 of the entrepreneurs I interview are morning people.

Interesting.

It's kind of interesting. What book are you currently reading? Or would you say you gotta read?

You know, I'm currently reading Humor. Seriously. It's about how I having a sense of humor in business. Actually an asset, not a liability. It's really great. I love it. A few years ago, I had a realization a, I wanted to Be more funny. I took things really seriously. I was very busy building and I was like, I need to enjoy this a bit more. And I think laughing more. Having a sense of humor has something that's made my work life better. And this book basically gives me the research saying it's an asset to have a sense of humor and to have levity at work, not a liability. And they. A lot of research that shows kind of in our 20s, the amount we laugh goes way down because people think that they shouldn't be doing that in the workplace. And actually there's a lot of places where it's well placed and becomes an asset. So it's a great book. Humor, seriously.

I shall read that. That's. That sounds really good. If you had to pick one word to describe Michelle, what would it be? And why?

Glue. I don't know. You probably never heard that. I, you know, I sometimes I think, you know, I'm not a deep expert in any one thing, but we almost always perform better when I'm there. So I don't know how else to describe it, but just glue help gluing things together. I. My. In high school, I was on the basketball.

That's. That's a first. That's a. That's a really good one. What's keeping you up at night?

What's keeping it. Well, Covid, I guess, is keeping me up at night and just missing friends and family and. And. And obviously we're. We're lucky. We're very healthy. But I do miss seeing people back to where we started our conversation. I hope I get to see you in person.

I know you. Cloudflare just opened in Toronto and you can't even be here. It's. It's kind of a great chance. But speaking of that, what's your. What's your most favorite place in the world?

Was Kazoo, Saskatchewan. So it's Prince Albert National Park. I spent many of my summers there. And I. I think also part of it is May, April, thinking about summer coming. And I just have very fond memories as a Canadian spending at the lake. And I went to Waskaz. Husband grew up in Oakville, and so Muskoka would be his answer. So we spent a lot of time reminiscing about our lake summers up at. So I would say Waskasu.

Michelle, it's been absolutely delightful to have you. To have you on. You know, I'm sure that there's some great things that people kind of listening to. How can people get a hold of you if they have a question because it happens on the, on. You know, we have a lot of fellow entrepreneurs that listen and hear something and want to kind of get, get an opinion on it, basically.

That's great. Well, I love that you're doing this. I think it's wonderful. If I can be helpful, you can find me on LinkedIn under Michelle Zatlin. I have a profile and. Or you can also find me on Twitter at Zatlin, if that's the right avenue. Or you can email me. I'm michelleclavfler.com and so the more specific, the reason why you're reaching out, the easier it is for me to reply. But I really try to be helpful to other entrepreneurs because so many people have been helpful to me. Or if you're looking to work at Cloudflare, if we can find a way to partner or be helpful to you, I try to be very responsive. So I think those are three different ways that you can get in touch with me.

Michelle, thanks once again. Been very, very interesting session.

Okay, thanks so much for having me.