Legends of Tech: Episode #22

And we're live. Good morning, good afternoon and good evening, everyone. Welcome to episode 22 of Legends of Tech.

Today, I'm super excited to have this legendary tech superstar herself.

She studied at Harvard. She's been in the world's top 50 women in tech.

She's the co -founder and CEO of Cloudflare. Please welcome Michelle.

Thank you so much, Chris. Thanks, everyone, for tuning in and really excited to be here.

Thanks for joining. Look, I've been really pumped up for this episode.

So I thank you for joining and appreciate you taking a bit of time out of your hectic calendar to join Cloudflare TV.

So how are you anyway? How's everything going in your world?

Things are good. I'm in beautiful San Francisco, as you can see by my backdrop, although it's not quite looking like that today.

It's winter is around the corner, so it's raining, starting to rain, which is good.

We need the rain. It's been really hard fire season. So that's that's the good side.

That side is it's raining and some of the COVID cases are going up. So things are kind of starting to lock back down a little bit.

So I feel like some tough times are ahead, a bit ominous, but generally good.

That's good to hear. So I guess the thing that always fascinates me about this conversation is how did you actually get into the tech sector?

Oh, how do I get into tech sector? I, in some way, I kind of fell into it and then ended up falling in love with it, I guess, is the is the way to think about it.

I I got my way to the tech sector started from some nonprofit work that I was doing.

I used to be really involved in some charity work community, give it give back work when I lived in Toronto and was on a committee with an entrepreneur and ended up going to work at his company.

And that's where I really got the first taste of technology.

And it was thrilling. I love that smart people were working on hard problems.

I love that there was always some sort of reason or solution when it came to tech.

I love that you could really ship a product that impacted a lot of people or delivered a lot of value to a lot of people globally.

Like it was such something where you you could you felt so much accountability over what you were doing and it had such impact globally.

And so I end up that's how I ended up falling in love with technology. It was like, wow, smart people working on hard problems and being able to impact people around the world.

This this seems pretty great. And then you layer on top of an industry that was growing and seemed becoming more important, not less important.

That's how I ended up pursuing my career here. Yeah, right. That's amazing.

So growing up, there was no you had no desire to to jump into the technology into technology.

I mean, I grew up in a small town in the middle of prairie land in Canada.

Like my, you know, farmers and farmland and, you know, had a great childhood.

But just people in my province, Saskatchewan, really stayed there like leaving was just atypical.

There was certainly not a lot of technology like in my school programming or like I didn't see it on my data like this.

One of the career counselor talks to you. What do you want to do with your career?

I didn't even realize that was a choice. So it took me a long time to realize that was a choice and like a long time.

And so, you know, I just didn't even know what that really meant.

On the flip side, like I love science. I love, you know, I knew computer programming.

I like I knew those things. I didn't really understand what what a career in technology was.

And and maybe that was says more about me than others.

But anyhow, I think that was so. No, it wasn't something that I was really young.

But as I started to go to Toronto, I went to McGill and you started to kind of be exposed to more career types where it's not just about being a doctor or dentist or a lawyer, that there are other career paths that you kind of start to expand.

And being like, what is this and becoming really fascinated by it and then figuring out, oh, wow, I didn't even know this existed.

Is this for me or not? And so I think it was something that really more emerged when I was in my 20s after after university or college, depending which part of the world you're in.

Yeah, no, that's fair. I just love our industry because we've got a non-traditional way of coming into into where we are.

I guess we're probably one of the youngest industries in the world.

And everyone that you talk to, there's no you know, I woke up when I was a little kid thinking I'm going to become, you know, work in Silicon Valley or work for an IT company.

Everyone sort of come in from a very random or very different way.

Well, like you said, it's kind of emerging.

Right. It's a fairly new I mean, the Internet only was invented 30 years ago.

And so, you know, took time. And now it's so it's obviously pervasive in all of our lives and it's changed how we connect and communicate and do business.

And it just feels like there's so many more things left to be developed and invented.

So it is it is new. And I mean, 30 years young, I guess, is a good way to think about it.

Yeah, absolutely. That's that's fascinating. So tell me a little bit about your career path up until the point, you know, you met, I guess, your other co-founders.

I guess, you know, which other companies did you work for? And I guess, how did you how did you get into these companies throughout your career?

Sure, of course. So when I graduated from university college, I was a scientist.

I had a science degree and I really wanted to try something other than I thought I wanted to be a doctor.

So I really want to try something else. So I've worked at financial services, like a research and consulting firm, small financial services, boutique firm, a consulting firm.

I've worked at large companies like Toshiba and Google as product managers or running different parts of the P&L.

I worked at other startups like this one that I told you about that I kind of discovered tech called I Love Rewards.

So I've worked at both really big companies, Google, Toshiba, established companies like Toshiba was along for a long time, global, you know, Japanese, large conglomerate.

I've worked at startups and then I've worked at kind of more, I would say, profitable partnerships where it was this financial firm.

So I've tried lots of, I've seen lots of different things.

And what was interesting is I had done a lot of growth roles.

I had worked at some companies where things were growing and it turns out growing is really fun.

Growth is fun because when there's growth, it means there's opportunities.

There's always more things to do than people to do it. And then I went to be a product manager at Toshiba in the consumer electronic business and they had done a really good job.

And it was during the period of time where it was like the HD, DVD, Blu-ray, Blu-ray wars, and this huge migration of flat, flat, flat screen TV.

So there was big shakeup in the industry. But what happened where I was working at Toshiba Canada is that the industry wasn't growing, they were shrinking.

And that's where I really got an up close personal view of, wow, I had a much better appreciation why growing was fun because that was a job where things were not growing.

And so it was all about cutting costs and finding synergies to take costs out of the business.

And I mean, that's, it was a really great lesson.

I learned a ton, you know, having to work in that environment, you learn a ton.

But when I went to business school, I was like, I'm not going to another company that's flat or declining because it's not as fun.

It's way more fun to grow and be inventing new things and pursuing new opportunities versus I got to cut my, I got to find costs out of the business.

So it was, it was one of those places where the cost, where our growth was something that I really discovered I liked and looked for that post MBA.

It's fantastic. Yeah, it's, yeah, there's nothing worse than being part of a company that's shrinking and they're cutting costs everywhere.

I think this is the first company that I've worked at probably, probably the last six years of working companies that were in a decline that was trying to grow.

So, but you know, the more you cut, how are you going to grow?

So it's good to be part of a place where it's, we're in a growth mode.

Therefore it's, we can't find enough people to do the jobs that you were saying before.

It is. And so when people ask me, Hey, what should I do with my career? One of the things I'd say is, you know, think about is the company growing or not?

Because if it is, there's just more opportunities to go around for the people that are doing a really good job there.

Yeah, absolutely. No, you're spot on in that one.

So, so you went from Toshiba, then you worked at Google. So what was, was it Google?

Was that the next, was that the next job? Sorry. I, I, I worked at Toshiba.

I went to do my MBA and then during my summer internship, I worked at Google.

So, so yes, but I also went to school during the same time. What was it like going from a company like Toshiba then to a company like Google?

What was the, it was my summer internship as my MBA program.

So I knew it was a summer and it was just, it was, I mean, it was the summer of 08.

It was 2008, the summer. I mean, you know, it's 12 years ago now.

And I mean, Google was a big deal. It was kind of the company, one of the companies.

And so I was, it was awesome being there. I was in the New York office, in the meatpacking district.

And it was just kind of like what you envision.

I like the first day and there were scooters around the office to take, to go zooming up and down.

I remember my parents came to visit and like, I picked them up at the elevator on a scooter and they were like, where am I?

You brought, you know, you brought your parents to tour the office because it was so cool.

I can tell you, I never brought my parents to any other office except for Cloudflare's because obviously I'm very proud of that.

The people, I just, everyone was so smart, passionate.

So it was a really, it was kind of what I expected.

And even better, like it was such a great experience. On the flip side and everything they shipped touched millions of people around the world.

And so that was such a great summer internship.

On the flip side, it was a big company.

So it was, you know, as an intern, you're kind of trying to navigate something in a couple months, which is hard, right?

You're like, where am I? So who you work for matters a lot, which is actually the second advice I give people when they're trying to figure out what to do with their career.

I'm like, who are you going to go work for?

And how long has that person been at the company? Because I think in a big company like Google, someone who's been there for a long time that can navigate and help you navigate goes a long way.

And so that was really interesting.

Yeah. So it was, it was, it was a great summer internship. I learned a ton.

They had a great MBA class. And we do that now at Klaffler where we have a group of, you know, students who, interns who come together and you make it, you get to know others.

And those people that were in that MBA class from across the country, you know, I keep in touch with some of them and they've all gone on to do such amazing things.

So that's been really fun. The somewhat sad thing, but although probably a silver lining, and I'll just share the story because, you know, I worked at Google for the summer.

Obviously you do a summer internship hoping you're going to get like a full-time offer.

That's kind of part of the deal. And Google gives your full-time offers in October.

And I don't know if anyone remembers what happened in October of 2008, but there was a huge financial crisis.

And it was, it was not, it was, I mean, kind of like what's going on in the world now, but in a different sense of the world, different, more financial sense of the world.

And there's just this huge collapse. And so my, my manager called and said, I have bad news.

We're not giving anybody an intern, like anyone, a full -time offer from the intern class, including you.

We're not giving anybody. And I was crushed.

I honestly thought, oh my God, my career is done. So that was what I thought was going to happen.

And sometimes I think back and you never know, this is one of those things where I didn't, don't have sliding doors, you know, that movie where you can see what would happen in parallel.

But, you know, a couple of months later, I was on a trip in the Silicon Valley and that's where Matthew and I started to work on Cloudflare.

That's where the spark for Cloudflare came from.

And we ended up doing it as a school project. And we ended up entering the business plan competition in my second semester.

We ended up winning it.

And the next thing I knew, I was moving, packing myself into U-Haul and come flying out to California to start Cloudflare.

And sometimes I wonder if I had had a full-time offer to go join Google, whether I would have done it.

Because to walk away from something like that, I don't know.

Like, I'm not sure. I would like to say that I would have, but I don't know.

And so maybe it was a blessing in disguise in the end.

So turning, I guess, lemons into lemonade, I'm not sure. That is such an intersection.

Who knows what could have happened from that point? And I remember me at that time, I was in a technical role before I moved into sales.

So I transitioned right during the GFC into sales.

Worst time ever to do that. But it was a hard part.

But yeah, I can just imagine if you had taken the Google role, who knows where things would be right now.

So tell me, I'm really fascinated about the fact, I mean, how did Cloudflare come about?

How did the three of you get together and go, you know what, this is what we're going to do?

I always find the inception of an idea and then the creation actually taking it out there, I think that's amazing.

How did that all come about? Yeah, it's a cool story. I don't know how repeatable it is, but it is a neat story.

So I was a student at Harvard Business School, and they do these professor-led trips.

And every time a student group wants to come visit Cloudflare, I'm always like, yes, we should have them.

Because just being a student is such a luxury. And we were on a trip to the Silicon Valley for a week in January.

And January 2009 was even worse than October 2008, because it was kind of a few months after the financial crisis.

It was not a good time.

It was pretty drab. And so there was this professor-led trip to Silicon Valley.

And usually they did these professor-led trips to China and India.

And you go to learn about commerce in these other parts of the world, Israel. And it was the first time they were going to Silicon Valley.

And how I recall it, it was such a magical trip for me, because I had grown up in Canada.

I was down in – and I had visited San Francisco and the Valley before, but I hadn't really spent a lot of time here.

And I was in the U.S. going to school at HBS. And so I was like, oh, my God, of course I want to come to the Valley for a week with a professor.

I can't wait.

And it was – what ended up being so special about that trip is it was about 40 or 50 students from, you know, first and second year doing their MBAs.

But everybody was so entrepreneurial.

Because kind of to self-select into that trip, you kind of had to be entrepreneurial.

There were builders. And so a third of the group wanted to start their own companies, and they came with their business ideas.

And they were working on their business ideas on that trip.

That's why they were there. They were founders trying to push their idea forward.

A third of people on that trip were people who really wanted to become investors.

They really wanted to become venture capitalists. So they were there to learn about how to become a VC.

And a third of us wanted to go find the next Google before it was Google to work at it.

And that was me. I was in that third group.

I wanted to go find the next big idea that I'd be proud to be part of and join the team and help be part of the team that made it happen.

But everybody had that entrepreneurial spark, and they wanted to see fine growth, and it was awesome.

So it was like this amazing week. We met with all these venture capitalists and entrepreneurs.

And Mark Pincus was one of the entrepreneurs we met because he was a big deal back then.

I mean, he still is. But Zingo was just growing like firewood. So we went to see him.

I was like, this is amazing. We got Time 101 and Jim Breyer. We met all these people throughout the week.

So anyway, Wednesday. So by Wednesday, I was a little bit tired because we'd been out all day.

You're learning.

You're out every night. Wednesday afternoon, we're down at an accelerator called Plug and Play.

And it's an accelerator for early stage companies. So this was, we'd done big companies, successful companies, but this was kind of like the very early pitches.

And I just sat through three early stage pitches. And I literally walked out of the room, and I was kind of tired.

And I looked to somebody on the trip because there was, you know, there was 40 of us.

So my friend on the trip and I said, oh, my God, if that guy can start a company, so could I.

Like, I literally said that.

And that person happened to be Matthew Prince, and Matthew Prince said, of course you could.

And I guess when I tell that story, because it was almost like when I realized what being a founder was, it demystified it to me a little bit, demystified it.

When I was in the Valley, I realized, I mean, there was a lot of smart people who were passionate about something trying to build things.

But I was like, that's how I would describe myself, too. And it wasn't like they were something that I wasn't.

And so it just really demystified what it was.

And so I just was like, wow, I could do this if I had the right idea kind of realization.

And then long story short, Matthew and I, he had done something before business school called Project Honeypot.

He was so proud of it. He always spoke about it.

And then basically I was like, Matthew, you always talk about Project Honeypot.

What is it? And we kind of went through an exchange back and forth in that hallway.

And long story short, that exchange led to we should create a service that helps make the Internet fast for everybody, helps protect any size website, whether you are a developer or a small business, a nonprofit, a large organization, a Fortune 1000 from online cyber attacks.

And we should help make the Internet more reliable.

And that's what turned into Cloudflare. I mean, I'm skipping a bunch of steps, but that's what happened.

And that's 10 years later or 11 years later.

We moved out here that summer of 2009. We kind of got tried to get the band together to get our idea going.

And we launched the service a year later, September of 2010.

We launched Cloudflare to the world. And 10 years later, we took it public.

Yeah, that's fascinating. That is amazing. What a story. Because you're so right.

It's that whole demystify. Yeah, we need to demystify something like that. People don't think how is that possible?

Like, you think, how do you become a CEO? Like, if you're sort of working in the trenches, you're like, how does it get there?

And the fact that you saw that and put those two things together, I think that's quite amazing how that's happened.

I guess, you know, with that type of mindset, I guess, what's your advice to people that have an idea or want to do something like that?

You know, do you have any, I guess, you know, a lot of things is people think about it to the point where they actually want to do something.

What's your advice to people like that?

I mean, I was never one. There are some people who, whose only choice is to be a founder.

Like they, that's all they'll accept. And they're like, I'm going to do anything I can to be a founder.

I was never that person.

So I don't really have good advice for those people because I like I don't, I don't, I can't like brainstorming ideas over and over and over until I get my idea.

I would rather go be part of something that's making an impact. And then, and then when I have my stroke, then go do it.

So I don't have good advice for that people.

But I do think I have maybe a good point of view for folks who, who, who may be like, I do think opportunities present themselves all the time for people.

And that it's so easy to find all the reasons not to do something like it is just so easy to convince yourself not to.

And it's especially easier, especially if you have family that tells you that's crazy or you have family obligations, or, or you have friends who say that'll never work like it's, it is really easy to talk yourself out of something.

And so I think sometimes if an opportunity presents yourself.

Sometimes you just got to go for it, not always but sometimes you should so I guess that's point one.

Point two is for people who really want to start something like I, I don't think all opportunities are created equally, I think some are better than others.

And that doesn't mean like a lot of elbow grease can't take something that's kind of a bad opportunity to make it a better opportunity.

But man, it's a lot of elbow grease and even good opportunities are a lot of hard work and a long time and again it's it's, you know, Cloudflare is a 10 year old overnight success story but it took us 10 years.

A lot, a lot of, a lot of hard work I mean again everyone, everything is hard work but man, anyway, it was tough so I do think that you want to try and find an opportunity that's stacked in your favor so where there's tailwinds to a trend or good business or a big business, I think they can look different ways, but I like I do think that opportunities present themselves anytime all the time.

Sometimes you got to go for it and try and pick one that's good, because it's, there are different varying degrees of quality opportunities and I think that that is probably the best.

I know it's a little bit like North Star but you know I that that's what I needed to hear and you know I think back to when I wanted when I wanted to start Cloudflare.

You know I was dating a guy, and it required me moving to San Francisco and he would live in Vancouver, Canada, and how many people would have said no no no no if you don't come move here I'm going to break up with you and I mean, to this person's credit, who's now my husband he was just like you should totally go for this like I was lucky, and you look at Malcolm Gladwell has a book called like the outsiders and he basically if you a lot of people say oh wow.

A lot of the great companies are founded by immigrants, and you know I don't know why, but one of the theories is because when you're an immigrant you're used to being an outsider and you're not used to you're used to having to work extra hard and to get accepted and you're not it's not the social proof you don't have the social networks of people around you saying don't do this or don't do that like it's a little bit and I think there's something to that you can kind of act a little different you can go down to right when everyone else is going left, and you don't have to have the peer pressure of, wait, why are you going left when everyone else is going right and explaining it versus okay like you're kind of creating this new path and so I do think there's something about like, it's, it's really easy to not convince yourself out of things and we're sometimes you should just say yes and go for it.

So, do you feel that it was a gut instinct for you when you made that decision.

No, like well that's the thing it wasn't like I woke up one morning me like no like I fell more and more in love with the idea and Cloudflare, as we went and I was lucky I was at, I was at school was a school project like it was I had, I had like what what one of my professors used to call like cover.

So I think that's why things like Y Combinator, and some of these programs are so powerful because you can go into the YC program for an idea.

And even if your idea doesn't work out you can say well as part of the YC batch, like it becomes like there becomes like a story involved versus I started something I didn't work for three months and now I have nothing like it's a little sounds better to say as part of YC versus the second version.

And so I think that as a student like I fell more and more in love with the idea as every, every month passed so I was super lucky in that case and then when we decided to do it I mean I, I mean, I had no idea I was supposed to actually had a job offer to go work at LinkedIn, and they were really early definitely fit my description of go be part of a company before it was LinkedIn, that was it.

And I went to talk to my boss in the cafeteria at LinkedIn and I sat down I said, Dan, like thank you so much for this offer.

But like, I started something in parallel. I got to see where it goes and he looked me straight in the eye and he said Michelle you were making the biggest mistake of your life.

And, you know, for 99.99% of people he was right, you know, I was being the biggest like LinkedIn ended up going to be huge went public like I would have my crew would have done just fine if I had done that, and, and this ended up being a great path to and so no I was not sure and I remember being like oh my god, but, you know, I just, I had to see where it went like I really did I just was like, I will never I have to see where this goes, even if it goes nowhere and so I'm glad I did so Matthew story, my business partner and I think we story that our third founder had a much more switch approach they're like what I'm in.

I think I fell more in love with the idea and I just tell that story because I think some people think that, like, if you have any apprehension, like apprehension apprehension and then you shouldn't do it I'm like what or or you just got to warm up to it I kind of, I think it's a personality thing.

Absolutely.

That's great. Now we actually have a. We've got a weekly, you know, some committed listeners and viewers to our show.

We've got a question if Jason from San Francisco so you can play the question.

Sure. Great. Hey, this is Jason calling from San Francisco.

Great show as always Chris. Michelle, my question for you is, was there a moment where the idea of Cloudflare that this business you're building went from something that might work to feeling like something like, wow, this could really be something big where it became really tangible.

All right, thanks a lot.

Bye. Thanks Jason. Yeah, thanks so much for the question, and there were and you know what there are many times where that's happened, like I've kind of read felt like we've been reaffirmed many times with the holy smokes or something big here.

I think I'll give you two examples early on different stages so very early on kind of after I walked in that hallway at plug and play and we started to work on the idea.

I, we had to say like was there a problem here and so we did a survey to a bunch of small website owners that were part of productivity pod and we said hey how big, how much do you care about web security like how much you care about web spammers.

And I remember the survey results like it's it's kind of forever imprinted on my brain where the results came back and there is, you know, you had to pick strongly agree kind of agree but then there was free form boxes, and the free form boxes were like gold, it was like catnip it was amazing.

This is the first aha. The example that the sentiment that came through from the survey was web spammers are criminals they're the scourge of the Internet.

Wow, okay. Web spammers make me believe in the death penalty, and it was just like very strong visceral disdain for the problem, and you're like wow and then the second part of the survey was like what do you do to solve this problem and there was no good solution.

And so I like that was an aha where I'm like wow there's a real problem here.

The question was could we come up with an interesting technical solution that would solve it and so the next aha was when we did that.

So that was like really early but then earlier again you got a 10 years you got to find more ahas along the way because there's sometimes you're like what am I doing but anyhow, I remember, you know, we're getting our first customers like a year later and we're running a private beta and no one knows us and we have Cloudflare we're trying to get people to sign up for Cloudflare and it was hard.

And you know for every 10 people we asked like two people did it, and whatnot you know like it was that just the nature of getting going.

And I remember getting emails from these early customers, where someone wrote saying, Oh my god thank you thank you for the first time in four years I slept through the night because my pager didn't go off and the pager didn't go off is because the cron job that was offline we were helping clean up some of the bot traffic.

So we made this freed up the server to available to run actually legitimate resources.

So they weren't page, and I didn't see the person was almost like they were crying through the email they were so like joyous I remember another one so I'm ready being like this is the best thing since sliced bread like I forward that one to my parents, and so I think that there were all halls along the way that gave us conviction I remember like five years and I was sitting budget planning budget planning right now with Chris Merritt who's currently our president of field operations and I remember looking up and be like, there's a good business here.

And so we I kind of like I think these halls along the way or a good sign.

That's fantastic. Thanks Jason, and good to see you watching again right thank you very much.

That's fascinating Michelle.

What keeps you motivated to do what you do. I mean I have two answers that I think the first is that we help build a better Internet and I think that we really do that so that's that feels great and important and the other curve I like to give people is like work on something that you're proud of, because there's a lot of jobs in the world you're probably highly employable so being part of one where you feel like you're doing something that's a creative it feels good and so I think that that's that's part of it but the second one is probably the even bigger one the North Star one is, you know, I met so I know so many entrepreneurs at this point, and, and have a lot of friends who started companies at the same time as us and everyone has different paths right we've been super successful very lucky.

And you realize well like what really keeps me going as well we're on something big this is a big opportunity and I feel a huge immense responsibility to make sure that it that it reaches its full opportunity full potential as an opportunity.

I think kind of back to not all opportunities are as good as others, like I think that this one is a has a large potential and I feel I am motivated by making sure that we reach its full potential I would feel unsatisfied.

If we got to 50% of its full potential like I think we should aim.

We should aim to fulfill its full potential and so I have the same I like to say so maybe a good place to say here is we're just getting started because that's how I feel I feel like we've done a good job but there's so many things left to do and it's kind of back to this this week, this is what keeps me motivated.

Michelle. Thank you so much.

We're nearly at time, there's so much more want to cover off so we're going to have to have another segment at some point probably when things quite a bit for us.

Just wanted to give you a really big thanks for for being on the segment today.

Your story is really fascinating I've learned so much about you today as well, and really appreciate your time, have yourself a good evening.

And thank you so much.

Thanks so much, Chris and thanks so much for having me on and this is really fun and I'd love to do it again or anytime.

Thank you. All right. See everyone.

See you next week.