Legends of Tech
A weekly podcast where Chris Georgellis, on the Customer Development Team, interviews people across the tech industry. From veterans, to hall of famers, day to day tech industry people as well up and comers. Get to know them as individuals, find out what drives them, how they got into tech, and what they see now.
This week's guest: Trey Guinn
Live, here we go. Welcome to episode 28 of Legends of Tech. Today, we've got a superstar legend himself.
He loves the great outdoors. He's worked for some awesome IT companies like KPMG and Cloudflare.
He's just recently finished quarantine in Singapore and he's located there right now.
Please welcome Trey to the show.
Thanks, man. Good morning from Singapore. How are you going? Pretty well, pretty well.
It's a pretty morning. And as you mentioned, I'm out of quarantine. I'm here with my wife and we're very excited to be able to leave the hotel room and be able to step outside.
So we're very excited. So tell me, what did you do for two weeks in quarantine?
Oh, man, I had these grand plans, but, you know, ended up doing a fair bit of work, tried to do some exercise, went a little crazy, got much better at ordering food in because the provided food is not very exciting.
Yeah, fair enough.
And were you like, you couldn't leave the hotel for two weeks? You cannot leave the room.
The key they give you is a one time use key. It opens the door one time.
And like you literally can't step into the corridor. There was actually a British guy in the last couple of weeks that was in quarantine and he was trying to visit, I guess, his girlfriend or his movie here for his girlfriend in Singapore.
And she checked into the same hotel and he like snuck out, you know, overnight and just went through the hotel to another room.
And they put him in prison for four weeks.
See, this is the thing in Singapore, they don't mess around.
If you step out of line, you'll get fined.
Lay down the law. Yeah, exactly. Yeah, it's just I had a story because like I think I don't know if it's still this still the case.
You can only have five people in your house.
Yeah, I think it's eight now. But yeah. Yeah. So this one family had six people.
And I think they're Swedish, like from Sweden or something.
They got deported back to Sweden straight away. The rules are the rules, you know, the rules.
Yeah. So have you have you spent time in Singapore before?
I've been here six or eight times with work, but it's normally always on these sort of like 72 hour trips, like QBR.
Tuesday, leave on Friday, and I'm blurry eyed and jet lagged and and I stay in a hotel, you know, that's across the street from the office.
And so I'm really excited to properly see to properly see the city for the first time.
Looks like we've got a special guest on our show, which is quite interesting.
I think I think he's connected to our conference by mistake.
All good. See, there's many surprises here on Legends of Tech trade, but we'll continue on.
So, like all things, I'm always fascinated about how how do people actually, you know, get into the tech sector.
So I'd love to hear your story and how you actually came into this beautiful industry that we're in.
Yeah. You know, it's funny.
I'm really it's just I think I always like to take things apart and generally ideally put them back together.
And when I was, I guess, maybe 10, 11 years old, my my dad bought the first computer in the house.
And by 12, I was disassembling it and putting it back together and then learning, learning the very first Windows and some DOS.
And I remember when it went from Windows 3.0 to 3.1 and you got a TCP, TCP stack.
And, you know, so the very beginning of the Internet at that age and was having just had a blast.
And so since then, it was like every job I tried to do was, hey, can I work with computers?
And so that's that's essentially how how I got into tech and sort of stayed here.
And it's a blast. And the funny thing is at Cloudflare is the first time I went into, you know, as a solution engineer in technical sales.
And I'd never been in sales before. And it always felt like it was like icky.
I was like, oh, I don't want to be in sales. You know, this, that and the other.
But it's a blast. It's just like, oh, I get to talk to people about technology all day long.
So it's a perfect job. That's fantastic. So tell me, so you love tinkering with computers and I guess that's how you started.
And you say every job that you went to, you gravitated to, you know, can I can I work on your stuff?
So I guess, you know, what was your where was your what was your first actual IT job?
Yeah, let's see. I actually have a nice little anti-pattern story about that.
But let's see. My first IT job was building computers in the mall.
And and it was not very exciting as a summer job. I think I was I would have been 16, 17 years old.
17, I think. And so I could work and make some money over the between, you know, over the summer between between the school year.
And I took the sort of building computers in the mall. After that, when I was in uni, I worked for the uni doing networking in the dorm rooms and this and the other.
After that, while I was still in uni, I got a different job for a company that built networks and managed them for customers around the city.
I was in San Antonio, Texas.
And then I moved to Austin and got a random job there and then moved to New Zealand and got a job in hosting and at a company that basically had its own data center, built web applications and help run the data center.
Then I moved to the Netherlands and got a job as an SRE at a host, like a managed services hosting company, and then went from there to an options trading house and help run their infrastructure for like that place.
And then went from there to KPMG.
That's KPMG in San Francisco and Cloudflare. But that's my 32nd resume. Wow.
So you worked in New Zealand as well? Yeah. Okay, cool. How did you end up in New Zealand?
Oh, man. I was 26, five years old, something like that. And I was like, I'm going to go.
I think. Oh, no. Back up. So when I moved to Austin, I got a job at a sort of IT services company that just worked on small business.
Like we were just like the guys that you'd call if you were a lawyer's office and say, come set up our computers and manage the network, et cetera.
And it's a tiny little company, like six, seven people.
And I worked there while I was in uni for about, I was actually worked there for four years or something like four or five years.
And while I was there, the owner of the company, like it wasn't anything special, but the owner of the company was like, okay, I'm kind of done with this business.
What I want to do is I want to basically give it to the employees.
Like, well, you guys can do like an employee buyout.
Just like pay me some profits over the next X number of years.
I'm going to go back to grad school. And then you'll just own the business.
And based on like how long you've been here, that'll be a percentage of the business that you own.
And because I've been there four or five years, I've been there the longest of everybody.
Because there's a lot of turnover in this little six person company.
And I was sitting here, I was like 25, 26 years old. And I was like, I could own a third of a company.
This is crazy. I mean, it was a third of, not much, but you know, it's still a third of a company.
And I had to ask myself, I was like, huh, I'm like, you know, I grew up in Texas.
I'm from Texas. And I was like, do I really want to live here long-term?
Like, because I could just, you know, go buy a, let's say like go buy a house, get married and die.
You know, and my whole life's done by the time I'm 28.
This is great. And I was like, that seems maybe a little rushed.
And I was like, do I really want to live in Austin?
Do I really want to live in Texas? Do I really want to live in the United States?
And so they basically like made this offer to me. And within four months, I was like, thank you, but I'm quitting and selling everything I own.
And I'm going to go travel around the world for a year.
That was like my grand idea. You know, put on a backpack and go traveling.
And I knew that I would have to do some work along the way.
And at the time, there were two countries in the world that would give Americans holiday working visas.
And it was Argentina and New Zealand. One, I don't speak any really very much Spanish at all.
Not nearly as much as I should. And New Zealand, I was like, oh, they speak English.
I think I know where it is. Applied for a visa and they just bought some plane tickets that ended up in New Zealand.
And then, of course, when I got to New Zealand, my thought was, oh, my whole life I've just done like literally tech jobs.
I'm going to go work in a ski field or be a bartender.
I'm going to do these things that everyone does that I just never did.
And then I went and applied for a couple of gigs. And I was like, oh, well, I can actually go snowboarding more if I go take a tech job because I can afford to snowboard.
If I do the bartending job, I can't do anything else.
So I was like, maybe I'll do a tech job again. And I sort of accidentally, I went to go get a tech job and I accidentally got a real job and stuck around there for three or four years.
So I had an absolute blast. That's awesome. Yeah.
And like New Zealand, did you end up, I mean, you said, I know we spoke earlier, you like the outdoors.
Did you get to go to Queenstown and go to snow and do the bungee jumping and all that sort of stuff as well?
Yeah. I mean, New Zealand's like a giant outdoor.
I mean, it's such a huge impact on my life, but it's such as just an outdoor adventure park and really got into mountaineering and a bunch of hiking and trekking or tramping in New Zealand.
But then also sort of technical mountaineering, so ice climbing and all that stuff.
So I went and joined the Alpine Society there and met.
And actually, it was the coolest thing, just the company I worked at was just the perfect time.
I was. I guess I'm like sort of like in my 20s and it was a tech company with 80, 100 people and literally some of my best friends of my entire life are still folks I've met when I started there.
And so there's just this crew and it was every weekend we're out doing another trek or climbing another mountain.
And I knew I had my life sorted because every weekend we're out doing fun stuff.
And I genuinely used to think we'd approach Sunday night and I'd be like, oh, man, I am so exhausted from these adventures this weekend.
I can't. I'm so happy it's Monday because I can rest over the week to get ready for the next weekend.
And I was like, OK, that's when, you know, life is right when you're when you're resting during the week for your for your weekend adventures.
Yeah, that's brilliant. So you like so you like a bit of the outdoors by the sounds of it.
So mountaineering, you know, we spoke earlier.
You're into cycling. Yeah. So tell me a little bit about your your mountaineering adventures.
I know, you know, New Zealand would be pretty awesome for that for that type of action.
But tell me how did you get into them? What what what draws you to that type of adventure?
Yeah, I don't know. I think I do like I just I like adventure.
Yeah. Just like sort of a big thing is accessing nature and.
But now pioneering, I say all the.
In California, but about it is this idea of just going for a hike and sort of connecting to nature and then.
And the thing about Al is nobody else there. So you're on top in the snow.
I'm seeing some view that no one else sees. You're not running into anybody else.
And it could be it's just it's really sort of stunningly beautiful and just sort of accessing that.
I find it sort of meditative and lovely. So that's that's where I got into it.
Fantastic. So, I mean, I guess, yeah, you're right.
It's one of those things. So how did you, you know, especially now and probably the last nine months or two a year, did you did you did you get to do a bit of that or was that missing as part of what I guess we're in?
Yeah, well, so I always sort of like do the sports that makes sense for the place you live, if that makes sense for the activities.
And so in New Zealand, it was a bunch of alpine climbing and stuff.
When I moved to the Netherlands, I got into cycling because the Dutch are amazing cyclists.
And, you know, you've got a lot of cycling in the Netherlands is awesome.
And then since I've been in California, I'll go do day hikes and stuff, but it's not like the intense mountaineering.
Also like to be able to go with my wife, which is helpful.
She's definitely not going to want to put on crampons, bring ice axe.
But and then I do a bunch of cycling. So over the last year with COVID in San Francisco, really lucky just to have a bike and to be able to go gravel bike riding or road bike riding and go out on these like sort of that's my new adventure.
Actually, I love gravel riding because you get on some dirt road in a national park and you're up in the redwood trees.
There's nobody around and you can go out for, you know, six, eight hour bike ride and just get totally knackered.
So when you come back, sleep well and feel like you've done something. That's fantastic.
That's great. So what made you go to the Netherlands? How'd you get, how'd you end up there?
Yeah, all these things sound like I had some great strategy in mind, but I didn't.
Basically, I was in New Zealand, had a great, you know, so I accidentally got a real job.
And while I was there, I was saying, you know, I started this trip to go around the world, you know, travel around the world for a year.
And about six months into it, I got to New Zealand, but I'd only been in sort of Southeast Asia, Australia, New Zealand, basically Asia pack.
And I like never got, I never went west.
So I was like, I gotta keep going west. And I had this idea that I was like, all right, I'm going to, I'm going to get a work visa in the UK.
So I thought that should be pretty straightforward. But then my, my plan was, I was like, I'll get planted in London and then maybe do a contract gig.
And then if I can get a real job, or if I can get a job or a visa on in continent of Europe, I'd love to just live in Europe.
Like that was, you know, I want to live in Europe. So I, being a very optimistic and ill -informed, I applied for my work visa, like a HSMP, the Highly Skilled Migrant Program in the UK.
Because hey, I work in tech.
This is one of the best things about tech is it's mobile. And I go get a, I like, I basically apply and then spend about six weeks traveling to get to London.
I went snowboarding in Japan for, for a few weeks. And then I was traveling in Europe and then get to London.
I was like, hey, you know, I'm going to apply for this visa.
And by the time I get there, it should be all sorted. But it turns out that when I applied, they basically changed some of the processing rules and it threw everything up into the air.
And instead of processing these visas, which had been taking two weeks, it took six months to get an answer.
And so I was like, oh, so here I am in London.
I have no answer on my visa. I don't have a visa.
I'm like sleeping on friends' couches, basically going broke and going, you know, I'm single.
But, you know, and I was just like, what do I do? What do I do? And, you know, this is still in the days when the tail end of when monster.com was still a thing.
And so some recruiter from Amsterdam said, hey, we've got this SRE job in this really cool company in Amsterdam.
What do you think? And I was like, oh, if it involves a paycheck.
And it ended up being an amazing company and I learned a huge amount.
But that's that's how I got to the Netherlands.
It wasn't like some clever strategy. Yeah. That's brilliant.
And where did you live in the Netherlands? I lived in Amsterdam. And, you know, obviously you ride a bike everywhere and the culture is amazing.
What I would say is that when I lived in New Zealand, I had this amazing access to nature.
But I really missed museums and ballet and the orchestra and like that sort of culture.
And then I moved to Amsterdam and had this incredible culture. And then I really missed nature.
I was just like, oh, man, I was like, how do you get to someplace that doesn't have paid bike paths?
And they're like, you get on a plane.
That's how you get to that. Exactly. Yeah. I found Amsterdam amazing. First time I went there, I remember getting off the train and just like sort of couldn't believe all the bicycles that you saw.
And then literally instead of a car park, it was a bicycle park and it was just filled with bicycles all the way through.
And then the funny thing was how it's the bikes that run the show there. So if you're a car, it's like here in Sydney in particular, it's the bikes.
You know, you guys are the bad guys.
But in Amsterdam, it was like you're driving a car.
Get off the road. It was quite amazing. But amazing spot. But, yeah, the culture, the history, I found amazing.
The Van Gogh Museum was pretty awesome there. The Heineken factory, you can't not stop by there.
But, yeah, it's a really cool place.
So how long did you stay in Amsterdam for? I was in Amsterdam for I think about five years.
And while I was there, well, about 18 months in, I thought, oh, I'll be here for 18 months, two years.
About 18 months in, I met my wife.
And so I stuck around to see where that was going to go. We ended up getting married.
And so that all worked out. But that's how I ended up in Amsterdam longer than I expected.
My wife's British. She was in the northwest of the U.K. And then the challenge was after, you know, a couple years in, all I was doing was complaining about the weather.
Because here I'm this Texas boy. I'm used to sunshine.
I'm like, man, it's just cold and rainy here. And my wife, who's from the northwest of England, she's like, this is what I grew up with.
I don't know what your problem is.
But she spent too much time around me. She's like, wait, you made me realize how rainy it is.
I'm now dissatisfied with this. So that's when we decided to make the move to California.
Perfect. So you did a bit of a, you went literally around the world.
So you went New Zealand, Netherlands, and then you came back around.
Yeah, I went west. All the way around the world. It just took me the better part of a decade.
I was going to say, that's a pretty cool way to do it. I mean, you've seen probably you've gone to the furthest part of the world, which we tend to think we're probably on the bottom end of the earth.
And then you've gone to a pretty cool place in the Netherlands.
So you end up back in California.
Yeah. Is that around the time you joined Cloudflare? Yeah, that's exactly.
So I should tell you about my little. But let's see.
I was at KPMG as an enterprise architect based in Amsterdam. And what was it?
We had a website. KPMG's website at the time was actually run on SharePoint, frighteningly.
And they had dual data centers, one in Europe, one in the US.
And the idea was it was like a DR. So in case something went wrong, they would do a DNS switch and route all their traffic over to the other website.
And then one day, the website gets knocked offline.
And there's just this huge load on the website.
Not that SharePoint at the time couldn't really handle much load. But they're like, oh, we're being DDoS.
We're being attacked. And I was like, I don't know this is a DDoS.
But let's figure out what's going on. And I was an architect that was helping with data centers.
And so that was in my purview. So I was trying to help with figuring out what were the solutions we had in place and what was going on.
And what it actually turned out to be was sort of early days AWS. This is 2012, I guess.
Early days of AWS. And there was a company that was going to collect translations, basically.
Because a lot of how translations work is less smart AI trying to figure out how to say something in French.
It's more like, can I find that string already translated?
And the KPMG website, and it's available in like 20 languages.
So someone's like, oh, cool, here's a whole bunch of text that's translated in like 20 different languages.
So they built a crawler and they put it in AWS and then they auto scaled it in AWS.
So it just crushed their website. And also especially you're hitting all these pages that are not in cache, et cetera.
So it was just like it was a very expensive crawl.
And so website knocks offline. They fail it over. It just knocks off the line, the DR site, because the problem didn't go away.
We just actually figured out who was doing it, you know, and said cease and desist.
And they stopped.
And they were apologetic, too, because I don't think the people really knew what they were doing.
And anyways, and that solved the problem. So it wasn't a DDoS.
But I was sitting here through this experience going, man, what we need in the world is like some kind of like rate limiter that would just exist in the cloud.
That we could like sit between two geographically distributed data centers. And I was like, is there like firewalls or rate limiters or something like that?
And I just started Googling and found Cloudflare.
And I think when I found Cloudflare at the time, it was probably like an eight-person company.
I think we had three data centers at the time or something like that.
It was this tiny little idea, really.
It's just like this idea in Matt and Michelle's head. But it was this major sort of like light bulb moment for me.
I was like, wait a second. You could have like a load balancer or a rate limiter or a firewall that just sort of like exists in the Internet.
Like that's a game changer. Because our whole life was just working on Internet -applicated delivery and all this stuff.
And I was just like, if you could like decentralize these functions, that's just unbelievably powerful.
So I ended up giving Cloudflare a call. And at the time, who did I talk to?
Because it's such a small company with Michelle. But I didn't spend like an hour on the phone with Michelle because she's like, well, we're not ready for KPMG.
But tell me what you guys would be interested in. And so we ended up chatting.
And then I was just, of course, super impressed because Michelle's brilliant and what have you.
And so here I'm like, I'm really impressed by the founders.
The tech just like really blew my mind. And I was like, you know what? So this is actually my plan.
I was like, hey, you know, Susie, my wife, like we're moving to California.
I want to go work at this company called Cloudflare. And anyway, so that was basically the idea.
I was like, and I'm American, so I can just go there.
I don't need a visa. This is a lot easier. And so I showed up at Cloudflare and basically like pitched a job.
I said, I could see that you guys are going from self-serve, you know, because at the time it was like a free pro.
And I think they'd launched business about the time I discovered them.
And I said, I can see that you're now going into enterprise.
But as you go up to enterprise, like these customers aren't just going to come, you know, a KPMG or a BP isn't going to come like swipe a credit card and trust a $20 billion brand to just some swipe of a credit card.
I said, you're going to need technical folks that can talk to the engineers and can also talk to the business folks.
And I said, I think I could do that.
And they're like, oh, that's called the solution engineer. I was like, really?
I had no idea what that is. And so whatever it is, I want to do it. And they were like, well, we're really, you know, it's an interesting idea, but we're not really sure you're the right guy.
And I said, how about I work? How about I like audition, work for free for a couple of weeks and we'll see if it works out.
And anyways, they let me do that, which was amazing. And then they let me stick around.
So that's how I started at Cloudflare. So you literally worked for free, told them this is what you need.
And eight years later, you're still here. Yeah.
Yeah. And then this solution engineer job that I sort of pitched is now like a global team of 100 people.
So were you the first solution engineer for Cloudflare?
Yeah. Yeah. I'm the first solution engineer. And I just sort of stuck around.
Yeah. I'm like a bad rash. You're like a bad rash. So let me ask you. So, like, I mean, obviously, you've gone, you had a thought and you went there.
Did you literally, like, go to 101 towns and knock on the door and say, I want a job?
Like, how did you?
Oh, yeah, yeah. So, well, it wasn't 101 towns at the time. So at first I was chasing them up before I moved to California.
And I just kept calling and asking for Michelle and saying, oh, I'd like to call you about a job.
And, you know, at this time, I think there was 20, 30 people at the company. And most people would, any random person at the time would have to answer the phone.
Because there's just phones out in these, like, groups of desks. You know, like, Nitin, who runs infrastructure, got stuck by the sales phone for a couple of years.
Always answering sales calls. But anyhow, I just kept calling. And most of the time they were like, yeah, we'll take a message.
We'll see what happens. And then eventually someone just, like, you know, put me on.
And they're like, oh, sure, I'll give you Michelle's email.
And she was kind enough to let me do, like, some Skype interviews.
And then what was the deal? I also interviewed at AWS at the same time.
And AWS flew me from Amsterdam to Seattle for an interview. And then I arranged it.
I asked them, I was like, well, can you take my flight back on this day?
I'm going to stay in Seattle for a certain amount of time. And I bought my own plane ticket from Seattle down to San Francisco and stayed in an Airbnb.
And basically, like, kept calling Michelle again and said, hey, I'm in town.
I'd really like to meet in person.
And then I was just persistent. So they would let me come into the office.
That's when they told me, like, well, we're not really sure you're the right person, et cetera.
And then luckily I was able to sort of do this pitch.
And it was actually a friend of mine's idea. I shouldn't take credit for it.
I'm normally not that brave. But a buddy of mine was like, hey, you're going to be in California.
You're going to be in San Francisco. You've got, you know, a couple months of savings.
You've got a couple months to look for a job. Like, why not just offer to work for free?
So I got to credit my buddy Thomas with this brilliant thing.
It was also incredibly uncomfortable. Like, the most uncomfortable thing.
But anyhow, yeah. What an amazing story. And look, I don't want to cut us off.
But look, we're almost out of time. And I think, mate, we're going to have to have a part two of this session at some point.
But, yeah, just really fascinating.
But I guess what it proves in, I guess, you know, in our industry, never give up.
And hopefully these little gems and ideas, people can take those on board.
But I find it quite fascinating how you literally said, I'm going to work for free.
You kept hassling him. And then you got a competitor to pay for your ticket pretty much to go and get a job.
Well, Trey, look, thank you so much for your time today. I hope you have a good stay in Singapore.
Obviously, I look forward to catching up with you in the near future.
We're going to have part two of this segment at some point as well.
And, mate, I've learned a lot about you today. So, once again, thank you so much.
And hopefully I'll see you soon. Yeah, thank you as well. I'm a talker.
So I appreciate it. Awesome, man. Take it easy. Thanks, Trey. See you. Cheers.