🫵 🧠 💰 Matheus Riolfi is co-founder & CEO at Tint.AI, Harvard Business School MBA graduate, former Turo employee, Angel investor, Y Combinator alumni and self-proclaimed Embeddable Insurance Nerd
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Entrepreneurship, risk-taking, and self-discovery. (4:33)
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Embedded insurance for tech platforms. (9:09)
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Insurance industry and its transformation. (14:06)
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Entrepreneurship, immigration, and startup success. (19:44)
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Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 0:01
sweat equity podcasts and streaming show the number one business comedy podcasts in the world. A little bit of a different intro. Sorry, we didn't get one last week. I've been messing up our scheduling. But we will make it up to you by always providing value but we'll make it up looking into some fun stuff in the future. So we'll make this intro very quick. This episode is sponsored by zap yet the first search optimized AI content writer. I've been using it. I don't like any of the other AI writers. They're not simple enough. It's a little bit too confusing. You sign up for the trial. You get boned on the subscription. And you go I'm going to learn that I'm going to learn that it's up yet. Very easy. My dad could use it. That's how easy Zolciak it's hooking up SEO. I've been cranking out blog posts for clients with it and if you go to zip yahoo.com zupyak.com promo code sweat as a key sweat as in traded defensive in Montes sweat. You get the hookup holler hear me? That's Zippy Zippy yak.com, promo code sweat. And this podcast was recorded a little bit ago and just couldn't get my shit together to get it up. It was an interesting conversation with my old pal that worked at turbo TS Mateus should probably look that up. My old pal, Matias wrote real fleet. It's a tough one. But we talked about scaling up being married. And not making it work yet, but having someone that believes in you as a partner. Very cool. Very interesting, dude. So let's get this party started. I can't yell because I'm on the road in the hotel. So I'm gonna go ah, the tidy tears is
Matheus Riolfi, Co-founder & CEO at Tint 2:17
my tears potatoes. Yes. Okay.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 2:21
It wouldn't be in sweat equity podcast, if I didn't mess up something I'm supposed to read.
Matheus Riolfi, Co-founder & CEO at Tint 2:27
Has Z right? How are you?
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 2:30
I'm good. We just we get right into it. We're doing a little differently because of scheduling snafu on my part. So it's just you and I, my, my partner, I got to stop saying part of my business partner, my co host, who's in the background, you can see him and I usually do together. I always like to ask everybody. Have you listened to the show before coming on?
Matheus Riolfi, Co-founder & CEO at Tint 2:58
honest answer no.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 3:03
Know, it's so funny to us that a lot of people we get your Booker's that are booking agents that, hey, this person wants to come on the show. Great. Let's do it. So that's fantastic.
Matheus Riolfi, Co-founder & CEO at Tint 3:19
No, but I think it should partly for the records. And just so you don't feel bad. I think it kind of makes sense in the sense that like, the audience of people who are listening to the show and getting benefit, depending on how the show is structure, and the people they are kind of feature. It's very different. For example, I love this podcast called own that knows about business owners. So the folks are in the show, definitely. Or maybe never heard about the show. But like it still doesn't mean that it's not interesting. It's just that the audience maybe, hey, we only
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 3:54
got like 430 episodes pretty hard to find. It's I know that was a really good PR spin. I like that. Yeah, no, I mean, we only asked because people that come on, they don't know what they're getting into a lot of the time. And we're not like, we're not hardcore asking questions, but we do make it awkward, very, very often like this. So we'd like to ask everybody that comes on the for the first time. This question which made juxtapose against us being usually in tank tops and kind of silly. What advice would you ask your 13 year old self?
Matheus Riolfi, Co-founder & CEO at Tint 4:41
So why did my advice what
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 4:42
advice would you give your 13 year old?
Matheus Riolfi, Co-founder & CEO at Tint 4:44
How would you get okay,
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 4:45
I'm a little punchy today.
Matheus Riolfi, Co-founder & CEO at Tint 4:46
So yeah, no worries. What advice I would give my 13 year old self is to have courage. Being not don't be afraid about failure about doing things about Learning about looking stupid sometimes, but that's when I was 13 I think was a lot more careful and worried about No, I play tennis and I'm not sure if I should sign up to for this competition because I'm you know, when I have this idea, but I'm not sure it's gonna work like, right now I think I'm a little more like, yeah, just do it because it may be a terrible idea may be a good idea and that's one way to find out
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 5:25
what so number 13 in Brazil?
Matheus Riolfi, Co-founder & CEO at Tint 5:28
In Brazil? Yes,
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 5:30
playing tennis and unsure what it's kind of the bucket that answer underneath kind of the majority answers or like get rid of the radio noise, whatever you're in to be into it. Where do you kind of in a path that led you down from? You know, I'm not sure what I'm doing to oh, this is what I excel at? Or was I know that's kind of a leading question, but where are you?
Matheus Riolfi, Co-founder & CEO at Tint 5:58
I think it wasn't a bad, I wasn't a bad. So by the age of 13, I had already started my first very small business with a friend selling calendars to the teachers in our school. So I always knew I wanted to be a founder, I would end up starting my own things. So that pieces I think it was pretty much in the right path. Maybe at the time I had some athletic expectations I mentioned 10 is like I wish I could play whenever they want to be a professional tennis player made that there couldn't have gotten the out of my my father Pat but like professionally speaking, is roughly the same. So yeah, don't think to me was a changing pad. What's more, like maybe I would have gotten faster in places faster just because I would have take taking risks faster, done more faster.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 6:46
Also, what kind of calendars are these these sexy like fireman calendars? What are we talking about here?
Matheus Riolfi, Co-founder & CEO at Tint 6:52
Now we're talking about very boring like Christmas or whatever. So these are the back back stories like my dad traveled to the US I was 10 years old. He brought him on to the HP Deskjet like ink printers, which at the time was very rare. And we may have what year are we talking? We're talking that was 1994
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 7:16
Okay, yeah, yeah, the home printer is very rare Yeah,
Matheus Riolfi, Co-founder & CEO at Tint 7:19
home printer and color. So that's the thing. So we my my buddy and I were nerds getting a computer at the time already. And we just created this like waste your do calendars, happy birthday cards, whatever. And we started to print any regular paper and sell in our school to our teachers. I didn't know if they bought it because they were they were like you know feeling sorry about us they will think they will break our hearts or whatever. But we've so quite a bit of money that and we spent our money like you know, buying magic cards, buying toys, buying video games or whatever things that 10 year olds do.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 7:57
So you feel entrepreneurial pretty much since the jump in a way yes. Now you Yeah, so I'm just imagining you going around you know trying to try to hawk these calendars to teachers and they felt bad for you more than anything. They probably had a calendar of some sort maybe a planner
Matheus Riolfi, Co-founder & CEO at Tint 8:22
well they did use the calendars they did like but so I think there were some customer value on that. But you're right like you never know and then that he was just out of like no PD of us or it was really because they were they were breeding their work color again in a time where those are not obvious and easy things to find. But But ya never know.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 8:46
You remember what kind of paper we talked nice paper we talked in printer paper. What are we doing
Matheus Riolfi, Co-founder & CEO at Tint 8:49
there paper like plain vanila normal printed paper that you fold the like fours and then you have like some like yeah, it was nothing you thought were semi glossy paper sometimes we use but they again nothing. They were not they probably did not look professional. As if you were to print in a print shop. That's for sure.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 9:10
What so you're talking to me from Vegas right now. Yes. And your plight brought you from? I'm gonna I'm gonna butcher the the small city or from to not de
Matheus Riolfi, Co-founder & CEO at Tint 9:24
That's right. It's a city 80 miles outside Sao Paulo.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 9:30
Is that how you say it then I butcher it?
Matheus Riolfi, Co-founder & CEO at Tint 9:32
Well, your butcher a little bit you would say Toba Tae.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 9:35
tapa Tae. Yes. Look, I can't read English. So you know, trying anything Portuguese is gonna be tough. And now you're currently living in Vegas, which is a 101 want to get your input on how much you love Vegas.
Matheus Riolfi, Co-founder & CEO at Tint 9:55
I love Vegas, but I would put one caveat. We live in Summerlin, which is really deep in the suburbs? Yep. And it is like, what, 50 miles away from this trip. So it is a very different Vegas from what most people experience.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 10:11
Yeah, it's like being in Henderson Right? Like it is further
Matheus Riolfi, Co-founder & CEO at Tint 10:15
than Henderson is further than this trip than Henderson. So he's like Henderson. But even more suburbia, I would say,
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 10:22
what brought you over over there? It seems. You know, if you're usually if you're international coming in, you're usually staying in Vegas Vegas. What What brought you to the outskirts of Vegas?
Matheus Riolfi, Co-founder & CEO at Tint 10:38
Well, because for us again, my the backstory is my wife is also a founder of a startup also remote. So we're both in the Bay Area, paying a lot of money for cost of living, very high taxes. Like all the things they're not so great about California, California is amazing in many ways, and I love the Bay Area's show. But it just didn't make sense for the time of our lives as a couple of founders with a daughter, we need more space, we need no better housing for cheap, or cheaper rather than Bay Area. And that's kind of what brought us to choose to Vegas, and then why Why'd the suburbs is because like, yeah, we want to like, you know, shoot a suburb lifestyle, but it's just wanting to be in a place with better weather and cheaper cost of living.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 11:26
Yeah, yeah, I totally, I was just in Lake Tahoe. And I get why a lot of people from the Bay Area have a place in Reno, for that reason as well, you know, think of Reno as what you're just talking about, like the Vegas strip. And there's a part of Reno that's very fancy on the lake. And a lot of people choose to live there for the tax purposes. Look, I'll recruit you to Florida, if you want Florida's got Tampa has never been hit by Hurricane we need all the good people. We need more. We need better imports into this state over here.
Matheus Riolfi, Co-founder & CEO at Tint 12:01
Yeah, I love Florida. So I'll be easily convinced my wife a little bit harder. But I think one day you never know.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 12:10
Well, tell tell me about tent AI.
Matheus Riolfi, Co-founder & CEO at Tint 12:13
And so we we help tech platforms create their embedded protection products. So think about when you go to Airbnb, even if you don't think about as an user, you're purchasing insurance. So if you stay in a place and the place burns, you, you're covered. So many companies right now. So I b&b Uber, Apple Tesla designed to offer insurance products to their users, because it's a much better experience for the consumers. And they can now have a better business and make more money. And we power it all. So we help those companies structure and offer their own kind of protection or insurance products. And we provide all the technology, all the services, and all that kind of capital required. So we're really an end to end solution for those brands that are looking to offer insurance.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 13:09
You're filling unnecessary need in this kind of new bullet uninsured peer to peer kind of transactions. Is that fair to say?
Matheus Riolfi, Co-founder & CEO at Tint 13:19
Yes, this is one of our use cases, but it gets really everywhere. So if you think about we work with a company called you ship, when you can ship stuff from anywhere in the US to anything from anywhere in the US. And you can ship your car from Tampa to San Francisco. And we work with them to provide shipping protection. So if your car gets damaged, in transit, there's insurance this protection product will pay. So we're seeing shipping, there's a crypto so like it's really what we're seeing is there's this wave called embedded insurance. That really, if you think about 10 years, customers should buy most of the insurance products, if not all from the brands they love the products they love, not from the insurance companies directly. I think that's really what's what's going on here.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 14:06
I didn't know that. I didn't know that was the status quo. I didn't know that. Well
Matheus Riolfi, Co-founder & CEO at Tint 14:11
tell me the last time you bought insurance and then tell me how much you like your, your insurer of your car, for example.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 14:18
Well, I was I was on a mom son lunch date earlier today not bragging but I was she was like, Who do you have on the show? And I was giving her kind of, you know, the info I've got on Yeah, I gotta move insurance. This is gonna be a tough one because insurance. Like I hear a couple of words that I just kind of, I try not to zone out. I try to really focus
Matheus Riolfi, Co-founder & CEO at Tint 14:40
more but you know, that's the point. You're not alone. Everybody like so there's no point of insurance companies try to get you to love their brands because frankly you don't care and you shouldn't care. But if thing goes wrong, you must be protected because if you're not, you may be like in financial Jeopardy and like you know, while you're kind of Earning earnings and savings may be completely wiped out. So that's why insurance is so important. And capitalism doesn't work without it. But your point from a customer perspective, as much as it can disappear from your face and still give you the protection. That's what we were powering. And that's the transformation that is happening in the industry.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 15:20
What made you get into this? I mean, it is you just found you found a need and kind of hid it. Maybe it's not your passion, but maybe, maybe making this neat. And as this necessary need kind of fruitful for the end user maybe is what your What's your why, I guess I should ask.
Matheus Riolfi, Co-founder & CEO at Tint 15:38
My wife like, you know, if you work with it, again, it's very important, as I mentioned, like no people can have their financial lives completely ruined if something happened, and they don't have protection. But how I got into this is like, I was one of the early employees of Turo, the peer to peer car sharing conference. So lets you rent other people's cars. So as you can imagine, insurance is a big, the biggest is a top of mine, if you're renting out your Porsche or two is changing, you want to make sure that that's where well covered. And the person driving the Porsche needs to make sure that he or she is covered as well. Because if they get into an accident, they are off know hundreds of 1000s of dollars of damage, or if the car gets stolen or whatever. So that's what was on my background before teams. And that was when we kind of really stumble upon the problem. I never thought about the problem my life before. And she would join this company and spend 80% of my time doing it. And surprise me enough. Like, I found it very fun. And my co founder and I because insurance, as boring as it is, and like behind the scenes, there's a lot of like, it's a data problem. And it's very, like you're trying to predict the future. You're trying to figure out how much people were gonna get enacted in the future. So you price How much did you pay today? It can get very intellectually stimulating, I'd say. And again, as I mentioned, ultimately, it's a good product product for consumers, that if we can make them purchase it without having to think as much make it easier for them. We're making their lives better. And I think that gets me super excited as a founder.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 17:20
Yeah, it look, there's, there's a lot of entities, a lot of startups or you might be a disrupter in this kind of game, that it might not be sexy on the output. But that's where a lot of the opportunity lies when it's the unsexy things like this.
Matheus Riolfi, Co-founder & CEO at Tint 17:38
Yeah, and I would argue is the same for pretty much every business like do you think that Uber if arguably went to the taxi business, like, that's not a sexy business like Flexport, doing shipping of containers around the world now very sexy either. And they are to a point they're creating the industries or recreating in a way that becomes sexy and exciting. But he always started with a very kind of big, non sexy industry
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 18:05
while I was early money on Turo as a traveling comic, because, again, I think Uber was kind of sexy in the sense that I think the ones that really reach a lot of people are like, on a personal level is like, Why does this have to be this way? Like rental cars, still is really terrible kind of industry. It's like, why is there a line every time I go to get a rental car still like you, you should know exactly what's there. And then every time you go get a rental car, it's like, oh, we over booked it. And it's like, you haven't figured this thing out yet? Yeah, yeah, really haven't figured this out. And what 50 years of renting cars like they haven't caught up to everything, which is insane. Turo has its own, you know, sometimes issues I suppose I've heard horror stories, but I'd still rather go with that. Same with Uber. I was fine with Uber. When cities were trying to close it down across the country, when they first really expanded. It's like, Well, do you want to go in an unsafe car? Oh, you mean? Do I want to go in the taxi with knife cuts in the Plexiglas as a as a barrier between me and the driver? And no, yeah. Yeah, I think I'll take my ride with the person that has the incentive to drive safely. Right. Yeah. And knows where they're going. Now. Now it's swung a little bit to the other way where? I don't know the last time we've been in an Uber where they follow the the GPS, as they're supposed to do it. But they always mess it up. I'm like, how do you mess this up? How are you distracted? This is your only job anyway. What? So coming to America, you didn't have a lot of connections to get things going. Tell. Tell me about that plate.
Matheus Riolfi, Co-founder & CEO at Tint 19:52
Yeah, I definitely didn't. I came here I didn't know. I mean, honestly, I didn't know many people. But I went to business school. So that was almost like that was one of the reasons why I wanted
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 20:04
all business school. I believe it was not really heard of. Which Yeah,
Matheus Riolfi, Co-founder & CEO at Tint 20:08
it's a small one. The Harvard Business School. Oh,
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 20:11
yeah. Okay. Yeah. And
Matheus Riolfi, Co-founder & CEO at Tint 20:15
then I had Jokes apart like he's definitely like I, I kind of met a lot of people there. And then that was kind of one how I created my early connections. But even that wasn't enough. So I then joined Turo, right after business school and spent four years at Turo. That's where I think I met a lot of my more like professional tech base network. So for example, through a CEO was my former boss under her dad, he was our first check, attend. So he tried to though retain me make sure I didn't leave for like 15 minutes or so. But then he's like, now I know you. I know you should go. And by the way, he helped me in the first check. So by the time I launched change, four years after joining Turo, I had a lot of connections in the valley and new folks that we could sell to that I could recruit. And that made all the difference. I always tell founders that, especially in the b2b world, where you're selling to companies, you probably need some connections. And if you don't have work for someone work for some company to build them, because it's very hard to be successful without that. What
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 21:30
I mean that, that sounds like the American story, we like we should, we should push out to everybody in other countries. Hey, don't worry, you work hard. You do what you're supposed to do, things will prosper. But that's not met without kind of any strife. Can you tell me about when you're trying to get this going? And, you know, it seems like there. What were the problems that you initially hit with with this? Because, well, it might be a great idea. And you might have some connections, you don't have all the big time connections, right? So it's like, how do you? I feel like I empathize. A lot of people out there. There's a lot of great ideas. Most lack of execution, it seems like you had execution. But how do you get to the right players? You need to? How did that? How did that kind of all align?
Matheus Riolfi, Co-founder & CEO at Tint 22:24
Well, I think there's probably many, many, like, it's a very complex answer, I would say, but I tried to think about maybe simplify a bit. I think the reality is that like, as any startup that there is a very high rate of failure. And I mean, the odds are against you, as a foreigner to cemeteries you are against us is a bit larger company now, but I Gates is the same. I think that like, as founders, the way I see is like, you should try to increase the throughput, increase your profitability, as a profitable, higher probability of success, with as many things as you can. And then if you means like, not having other people who know and trust you, it's a first step that lets you get in the path where you could succeed does not mean you're gonna succeed. Most people have people they know, they try and did not, it's not gonna work out. But if they don't have that, then is even harder. So that's what I'm trying to say. So. And I think, again, in our case, always, story is far from linear. There's a lot of ups and downs as any startup, we're far from being successful. So the jury is absolutely shoo out. But you're right, like at least the beginnings of the journey were a bit easier, because we kind of put the right elements in place.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 23:45
Yeah, was there we're keeping this short because I have to run to go do our next podcast episode. So we're wrapping this up in a second but I'm always curious about the the fetal position move where you're, you're in that mode, where you're like, Am I doing this right what I call the fetal position you get in the fetal position move where you're you're almost catatonic you're like did I do Am I really fucked up my new family that I have. I know your daughter's only three. So this may happen way before. But was Was there a fetal position scared, fearful moment you had with all of this and how'd you get out of it?
Matheus Riolfi, Co-founder & CEO at Tint 24:30
I think you're always scared like taking the leap is incredibly hard. And especially if you have a high opportunity costs, right. So if you're in a job, if you have access to jobs, they're very well paying. It's very hard to convince yourself that jumping to this no salary for a limited time, that it has a high probability of failing makes any sense. I think for me like again, it was I put myself in a position after and I'm after learned getting burned before in my career. I put myself in the right place after tomorrow where I was like financially stable. So I knew my family wouldn't be in jeopardy, even if I know, the things didn't work out. So I try to do risk as much as possible. And at the end of the day is like just taking the leap. Going back to your earlier question, what I would tell my 13 years old, it's exactly what I did is like, just do it the right time. There's no right way. It's very hard. odds are against you. But you know what worst case scenario is not going to work out, you go find a job. Probably you get a better job than you would otherwise because you learn a lot in the process. So that's how I rationalize this decision. But yeah, and then if that thinking works for
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 25:45
everyone, it sounds like you took a very pragmatic, not very pragmatic. Yeah. And you got to ride or die chick as your wife it sounds like so that's good, as we say, in the rap game, because I'm a huge rapper. I'm not. But I appreciate you coming on, man. We want to watch the story progress, and we'll have to get you back on later down the line because especially with my co hosts here to ping pong off of you. Appreciate you coming on partner.
Matheus Riolfi, Co-founder & CEO at Tint 26:14
Sounds good. Thank you very much for having me. Really appreciate it.
Law Smith, Fractional CMO, Stand Up Comedian, Sweat Equity Host, and President of Tocobaga Agency & Advisory 26:17
All right, get back to work. You
