#CollisionConf 2019: A new era of entrepreneurship

Sam. Okay.

I was backstage, I actually did update my LinkedIn profile to include annoying in the skills and experience. I think actually that's of worth something. Now I want to thank the Prime Minister of Canada. That was an incredibly inspired set of remarks and this government has shown true leadership on the Innovation file. We're very thankful for that. So the next two speakers we have have each built something remarkable from the ground. The first is the co founder of one of the leading cybersecurity companies in the world. And the second is taking the world by storm with her creative voice in music. We're going to ask these trailblazing Canadians to come out here on stage to share their success stories and provide some guidance and inspiration to those of us in the room that are looking to do the very same. Please welcome in conversation with Lindsay Turrentine of cnet, the co founder of Cloudflare, Michelle Zatlin, and singer songwriter Jesse Reyes.

Hi. That is a hard act to follow, but you are going to be so glad that you're here for this conversation. I am really excited to talk to two creators. I think in this economy, everybody is a creator, everybody is creative. You have to be. And we have two women here who have created very different, but both really amazing things. And I wanted to ask you both, you're both Canadian. Jesse, you're Canadian and Colombian. You've both done a lot of work in this country, but also outside of this country. So you've taken your powers with you. How is that experience of working abroad, exporting yourself, being in import, something that you sing about a little bit? Jesse, how has that affected the work that you do?

I think that coming from Toronto, particularly, because I feel like the city is very well known for its multiculturalism, it gives you an edge when you walk outside and you're working with people in different countries, but you've already experienced that in your own country, that it just gives you a different perspective, you know, a different perspective from your own. And then that just enables more creativity because now you're wearing other people's shoes.

And now you can take your message to so many different people and know that it will resonate with them too. They understand it. Michelle, how about you?

You know, I, Malcolm Gladwell has this really great research that shows that some of the best entrepreneurs are the ones who are outsiders who faced adversity early on. And I grew up in Saskatchewan, which I live in San Francisco now. Yes, exactly. The wheat fields of Saskatchewan go. And what I tell people from when I'm in the United States and I tell people I grew up in Canada and they say, where from? I say, Saskatchewan. They're like, that's so cool. And when I tell people in Toronto or Montreal or Vancouver from Saskatchewan, they make a funny joke and they make fun of me. And so I think there's something to Malcolm's research of where you just look at his research and it basically says if you're an outsider, if you're left handed, you face adversity, you actually build up the resilience to keep going and they make better. A lot of those people go on to do really great things in their life. And so for me, growing up in Saskatchewan and then now living in the United States and building this global company, I think that there's this greater diversity to keep going. And so I encourage all of you who, if you've faced hard times or are facing hard times, like, keep going because if you're onto something, it'll make you stronger and better long term.

One of the things that we were talking about backstage, I'm also from a, from a small rural place. Sometimes it's surprising when you put your name in the bucket and your name actually gets pulled, you get picked. And I think that changes your perspective on things a little bit. Especially if you're not from LA and you're in the music industry, you're not from Silicon Valley, you're succeeding there.

Well, I have a funny story to tell you. I couldn't agree more. So I was living in Toronto for six years. I went to McGill, I lived in Toronto, was working, and I really wanted to go to business school. And I was applying to all these business schools in Canada and I was at a cocktail party and literally talking to kind of a stranger. And they said, and I said, I'm applying to business school. And they're like, oh, where are you applying? And I named the schools, like Rotman and Schulich and all the Canadian schools. And he looked me in the eye and he said, why aren't you applying to Harvard? And I kind of thought, well, it's really competitive. There's like 0% chance I'm going to get in. And he looked at me in the eye and he said, if you don't put your name in the hat, it'll never get pulled. And because of that one conversation from someone I really did not know, I actually ended up applying. And I got in and I just remember showing up there being like, I can't believe I did this. And again, the idea is that if you don't put your name in the hat, you'll never get pulled. There's no way someone's going to come knocking on your door. And I guess there's two sides of that story. So if there's something you really want to do, try. And on the other flip side, if you're talking to somebody and they say they really want to do something, be the person who says, you should try and do it. Put your name in that hat, because it can really make that huge difference.

What you said. I totally like the. The whole idea of failing faster is something that's really helped me in auditions and when I was making songs and handing out mixtapes to everybody, because the people that say no is just. It's fine. It's just a step closer to the person that's going to say yes or a step, like, closer to the person that's actually going to support you. You just need to try and fail faster.

I love that message. And I've done some reading about some of the pushing that you started. Busking.

Yeah.

Right.

Yeah.

And so what. What were some of the things you did early in your career to keep pushing? Were you handing out CDs?

Everything. I used to, like, record myself. I used to make these awful songs. And back when you could burn CDs, I would burn my own CDs, and I would put my name Jesse Reyes, and I would put my number, and I'd bless the cd and I'd have them in my purse and like, just doing out of the ordinary things. Like, there was this club called Government in Toronto, and I know all the partiers up here are like, oh, yeah, okay. So at this club called Government, like, years ago, I just turned 19, and I always walked around with them on me. Because I just learned from early on from coming from an immigrant family. Like, you make opportunities. So I would walk around with them all the time. And my friends said that they were going to a rave there, and I didn't want to go because I was like, I should go to the studio. But they're like, come. And I was like, I'll make it an opportunity. I'll just bring my mixtapes. And I walked into the first room, snuck on stage, where the DJ was like, made my way over and tried to give my cd, and that was one DJ down. And there was four different rooms. And I went to the next room and Calvin Harris was playing there.

Wow.

And I. This is years ago. This is over, like, six, seven years ago. And I asked my friends to hold my purse and I grabbed one cd and I Went through the crowd and I waited till security looked the other way. And I just jumped on stage and I waved my CD in his face, thinking it was a good idea to do that in the middle of a DJ set, which is not a good idea. But he laughed and then shook his head and took my cd. Security saw me, I ran off stage and I jumped into the crowd and my friends are in the back like, fuck. Yeah, celebrating. And then my first number one, my first number one as a songwriter, because that's how I got started in LA was as a songwriter. My first number one was a Calvin Harris and Dua Lipa.

Amazing. Awesome.

Amazing. And now you have Eva Colombia. Hell, yeah, baby.

And now you have 14 million Spotify followers.

Crazy.

That's crazy. It's amazing. So as you're going through this journey and you're pushing and you're pushing and you are an entrepreneur in your own way, what do you think that. What do you think the challenges are that are universal? Michelle, let's start with you. That everybody is going to have when they're trying something new.

Yeah. So I think I meet a lot of entrepreneurs. Best part of my job are the people I get to work with. Second best part of my job are the customers we work with. But the third part of my job are all the great entrepreneurs I get to meet. And there's so many around the world. And I think that there's something. If you're starting a company or thinking about starting a company, there's. There's one thing that I would start with is, am I solving a really meaningful problem that you really care about? And I think that that's like, where you have to start. You have to solve something meaningful and ask yourself, well, why hasn't it been solved before? So you got to start there. And the second thing is once you feel like, okay, yes, this is a meaningful problem, I really care about it, I'm passionate about it, and these are all the reasons why it's not being solved today or why I can do it better. Then you ask yourself, can you assemble the team to make it happen? Because it doesn't matter how good your idea is, it's going to require assembling a team to make it come to fruition. And if you can start with those two things, then the funding will come and the media attention will come and all these other things will come, but you have to start with those two. And so I think those are really universal of what's the meaningful problem? Why isn't it being solved today? If there are already five companies solving it, you have to ask yourself, well, why not just go work for one of them? What's going to make me different? And then you have to ask yourself, how am I going to get people to come along with me? Which really takes a lot of hustle and vision and treating people well.

So it's really about understanding people. And, Jesse, you must think about the same thing. You're writing lyrics that you need to appeal to a lot of people. How do you reach that? How do you reach them?

For me, personally speaking creatively, I think a lot of it has to do with authenticity and truth. And I think that probably relates to what you said. When you find something that you're legitimately passionate about and you can't really fake the funk. And I feel like more and more, if somebody is. Somebody's getting well acquainted with your product or with your music, people are going to start to just understand and feel when things are authentic and feel when things are synthetic. So I feel like it's important to just come from a place of truth. So that way, whatever you're doing is done with complete conviction and nobody can tell you different.

Yep. When I took the job that I'm in, somebody told me that half of my job was now communication. I'm a journalist, so that's kind of obvious. But as a manager, half of the job is telling people what they need to do in a way that they appreciate and buy into. And that's what you're doing for an audience. That's what you're doing is you're hiring. Also, that's what you're doing when you're hiring a team. You were talking a little bit backstage about how important it is to have that team for a creative person. Can you tell us a little bit more about how that's come together for you?

Yeah. I feel like an important part of success is not just, like, focusing on what your strengths are, but also realizing what your weaknesses are. And you said it. When you're building a team, you can't. It's a really basic thing, but I see adults doing it all the time when you're just not checking your ego. But the second you check your ego and you're like, no, I need this because I'm not good at that. And I need this because I'm not good at that. Someone's better at creators or someone's better at business, or someone's better at getting funding, things like that and assembling the team that way, as opposed to just thinking that you're capable of doing it or that just. Just respecting that. And also, I think there's a lot to be said. And again, talking to my perspective, speaking from my perspective as a creative, I think there's a lot to be said for finding people that aren't necessarily like, you're not. You're not going to start with a pro. You're not going to. You're not. Your team's not going to be assembled of pros if you're starting from the bottom. And what I think is important to look for is for people that believe in what you're doing, just, just how you said it, but legitimately believe in not having the focus on, like, education or anything like that. Because someone could have said that to me. And I never graduated college because I wanted to focus on music. And that's what I did. I spent 10 years, nine years, eight years focusing on music and developing my skills outside of school. But if someone was looking at me from the outside and saying, oh, you know what? She could have gone to school for music, she wasn't serious. That's not true. I was just taking the other route. But I'm passionate as hell, you know?

Absolutely. So it's about inspiring that team. Is there anything else that you think that this crowd, a lot of whom are thinking about their own ideas or thinking about getting started with something that is probably very scary, so scary to try something new. What's the wisdom that you would want them to take away with you?

I think there's still a lot I'm learning. So anything I share is obviously from, like, little things that I've learned. But I still feel like there's a lot I'm learning as I go. But if anything, I hope you can take that. Like, I'm learning as I go. I've. I've. I've learned a long time ago and, like, excuse my language, but to be frank, not to give a fuck about what other people think if I'm failing, because at least I'm actually trying. You just need to try. You just need to fail faster and grow thick skin, because not everyone's going to be cheering for you all the time. But as long as you have your back and you're like, no, I got this, I got this, I got this. You got it?

Yeah, absolutely.

It was about five years ago, I was sitting at a tech conference like this in Europe and I remember Ev Williams was. Evan Williams, the founder of Twitter, was on stage and he said, said something to the effect of the following of everyone's just making it up as they go. And then someone else had once told me it was actually George Lee, who used to run tech banking for Goldman Sachs. He made this comment, you know, if you think about it, he ran technology banking for Goldman Sachs. He's met every best founder, like every tech founder there's ever been. He has met this person many times. And he said something to me once of the best founders are the ones who have really high rate of learning. And so you put those things together and that's like something I wish I had known when I was starting of. It doesn't matter if you don't know everything on day one, everyone's just making it up. And really, your best asset is how fast you can learn. And so if you're going to work at a company that you're like, I really want to go work there, but I don't know anything about that role. Just start reading about it and asking questions and surrounding yourself with really smart people. All of a sudden, six months down the road, you're like, wow, I know a lot more than when I started. And then if you're an entrepreneur, you're like, I have no earthly idea how to hire a CFO or a CTO or VP of engineering. And, oh, by, by the way, I really need one of those to get my tech company off the ground. Just start asking people and really quickly. You have five conversations. You're like, actually, now I start to see some common themes. And so I think it's this high rate of learning and everyone's just making it up. No one knows all the answers. And you can go really, really far away if you solve a meaningful problem and assemble a good team.

So you've solved meaningful problems with your company. Cloudflare, you're valued at over a billion dollars. Now.

What.

What was a moment when you were. You felt like, I mean, go way back. You felt like you were making it up as you went along and discovered something you hadn't thought of yet.

Oh, it happens all the time and it still happens. Today we have a thousand people that work at Cloudflare, and I feel like I'm still learning. Just like Jesse, where it's. There's things where we, you know, you. You have a point of view, but you get new information. You're like, actually this big aha moment. And I think early on, when I remember we were starting, there was three. Three of us that started the company. We quickly grew to six people. And, you know, you had these AHAs maybe 10 times a day. And it might be like a positive aha. Like a high followed by three lows, and then maybe another high followed by. It was this huge emotional rollercoaster really, really early on where you're high and low many times a day. But what happens is, as you scale and you get. You kind of start to generate revenue, and you start to maybe get to that $10 million recurring revenue, and then you have $100 million in recurring revenue, and then you get to a billion dollars in recurring revenue. You know, like Shopify. The highs and lows are still there, but they're much more spread out. And that's your job as, like, a founder to build a company. It's like you want to find an idea, and then once you have the idea, you have to generally eventually generate revenue. That's the whole purpose. You know, that. That. That's an important part of running a business. And. And these aha moments just become more far apart, but they still happen. And I think that.

That.

I think being open and flexible is what makes companies. You can really build an iconic company if you do that.

Jesse, do those aha moments happen for you while you're performing? Are you ever on a stage and in the back of your mind, you're like, I just found something.

Yeah, totally. And they happen by accident, but it's awesome when they do. Like, for example, once I was on stage and the mic stopped working during a song, and I, like, the worst thing you can do is just stop. You can't. You just have to keep going, figure it out. So the mic stopped, and I was like, well. And I just pointed the mic that way, like, as if it was on and it wasn't. And everybody went off, and I was like, this is great. All right. Nobody knows so little things like that. But you just got to move, right? Because people could have not started singing, and then I would have just had to think of something else. But I feel like fear is the thing that you gotta eradicate. Because had I been scared to point the mic out and fearful that people wouldn't support it, then I'd have just spent another 10 seconds looking awkward on stage, not knowing what to do. But I feel like fear's just. Fear's your killer. You just gotta kill fear, and then you're good.

That's such a great lesson that sometimes that moment of what could be panic is also an inspiration to solve something creatively. And then you take that with you. And you probably do that at shows now regularly. You point the mic out.

Yeah.

And then it becomes part of the culture. Now it's a part of the show now it's a part of it. And it was something that had to go wrong. And that's. That's the other thing I feel. And it's such a cliche thing to say to, like, stay positive, but it really helps. It really helps. Like any. Any obstacle, any obstacle that comes in front, just take a second and train your brain into always observing that as a challenge as opposed to something negative. Always observe it as an opportunity to grow, which is such a cliche thing to say. Like, as I say. But it's true. It really works. It really, really works because you'll just be so accustomed to it that that fear will literally die and you'll just look at everything like an opportunity.

I think they call that the growth mindset.

The growth mindset.

I think that's what it calls.

I think.

There you go. There we go.

You're in the growth mindset. Well, and I think that this just reinforces the knowledge that everybody has deep down that limitations force creativity, that without limitations, and we all have them. And you've dealt with all kinds of limitations. And anybody getting started has dealt with a lot of financial limitations. And sometimes that lack of money can also be scary. Michelle, tell us how those limitations helped you make some good choices when you were getting started.

Yeah, so we raised money. Our first time we raised some money was in 2009. And I can tell you in 2009 was not a good time to fundraise. It was right after financial crisis, and it was a very different time than angel investing didn't exist, seed investing didn't exist. So we did a series A eventually from a venture capitalist. It was the only tech investment. Benrock, which was a firm down in Silicon Valley, did the entire year. So this month.