e38 Matheus Riolfi

38: Matheus Riolfi raised $30 million in VC funding. How did he find his first customers?

Matheus Riolfi is the CEO & Cofounder of Tint, an embedded insurance platform that raised $30 million in venture capital investment from Y Combinator and others. They’ve worked with clients like Uship, Deel, and Outdoorsy.

First Customers podcast episode 38 with Matheus Riolfi

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Show Transcript

Paris Vega (00:00.97)
Welcome to the first customers podcast. I’m Paris Vega, your host. Today we are here with Matthias Rialfi from Tint. He’s the CEO and co-founder. Tint is an embedded insurance platform. They’ve raised 30 million in venture capital investment from Y Combinator and others. They work with clients like Uship, Deal and Outdoorsy. Matthias, welcome to the show.

Matheus Riolfi (00:27.429)
Hi, Paris. Thank you very much. It was great to be here.

Paris Vega (00:33.43)
All right, let’s get right into it. How’d you get your very first customers?

Matheus Riolfi (00:39.233)
Well, we’re a Tint, so we started Tint about five years ago and we got our first customers. I think it was a lot based on our network. So Tint is a network, I can describe the company later, but we’re basically on the B2B space. So for us, I think it was important to have people who knew us and then could not only have a conversation, but trust us enough when there was nothing there, it was only an idea that we would be able to deliver results.

to them. So we really lean deeply into our network and people that we work with us, former colleagues, investors who we knew to get our first customer and I can talk more about it as well.

Paris Vega (01:22.41)
Yeah. All right. So when you say you used your network, what did that look like? Were you using certain platforms to reach out to people in your network? Did you do specific things to build your network in the first place? Go into detail there.

Matheus Riolfi (01:37.745)
Yeah, so we, I mean, I graduated from business school and at the time I was running one of my startups and I realized that startup didn’t work and I realized that I’m missing a few things and one of them was a professional network in the United States. I was born and raised in Brazil. So I came here, I didn’t know anyone and I had to build all this from scratch. So after my previous startup, I joined this company called Turo.

which was a time was a small series A startup out of San Francisco. And I stayed with the company for about four years, which I thought it was enough time to kind of know a lot of people that worked with me and other folks in the Bay Area. So that’s kind of was my main strategy was to join other company, build my network. And then by the time we started Tint, I had a Rolodex on LinkedIn, I would say from other names of people.

to message and get feedback on our idea, and eventually led to some of the customer conversations as well.

Paris Vega (02:42.67)
So you came to San Francisco knowing, hey, I need to build my network. What gave you that kind of context for, or that overall strategy? Was that something you were taught in younger years or what gave you that initial kind of goal and mission to build out that network?

Matheus Riolfi (03:01.109)
I believe it was the experience of trying to build a company, a startup in the US, in the Silicon Valley, without a network. So it’s very hard to convince your first customers in the B2B space where there is a bigger purchase, there’s a lot of trust involved, and it’s harder to raise money, it’s harder to convince people to take a bet on you when you have nothing but an idea, without knowing people, right? And I think as an immigrant,

back home in Brazil, but I didn’t have it here. So that’s why I tried to do that, go straight to jumping to my startup after business school. But then I learned the hard way that I needed a bit more if I wanted to be successful.

Paris Vega (03:49.026)
Talk a little bit about what you did with that first experience and what that maybe painful process was like when you were just trying to get out there and do your very first startup. What’d that look like?

Matheus Riolfi (04:02.513)
Yeah, the first startup was in the travel space. So we’re trying to streamline the process of group travel. So give groups of friends and families traveling together better access to pricing for flights and hotels. That was the general idea. So it was a B2C, we were selling to consumers. I think getting customers at the time was not as hard because as a B2C business, you can put an advertising.

on Google, you can put a website and you have more organic traffic. So we were trying, and at that time, the main issue for us is getting partners to give us better rates, raising money from investors without knowing anybody here. So then I think I learned the lesson that I really needed to have a solid foundation, know a group of core people before we wanted to start my next venture. And then…

When I was at like fast forward to 10th, when we were starting the business, I had spent four years at Turo. So I had known work with a lot of people. We have like not only kind of building professional but doing personal relationships as well. So my the CEO of the company was our first investor check. He knew us. He kind of trust us and thought that we would be good founders of startups. So it was a very different conversation.

than the one I had when I tried to do that with like knowing anybody.

Paris Vega (05:34.306)
Right. And you went to Harvard, right? Okay. See, and I think you said you got an MBA there. Okay. And so were you trying to build your first startup before graduating from Harvard or is that after, cause you’d think that would give you some credibility and you know, would get, getting attention from people because that’s a, that’s a big brand and a university one.

Matheus Riolfi (05:37.897)

Matheus Riolfi (05:42.938)

Matheus Riolfi (05:51.251)

Matheus Riolfi (06:00.057)
Yeah, no, it does. It definitely opens doors. So I worked while I was at business school and I worked like a few months after a graduation as well. And I think it does open doors, but you know, you can use to like, you don’t have the full kind of trust and relationship, right? So sure, like granted, like we could have gotten the first meeting and that the idea was already enough to.

captivate people’s attention from investors, from customers. So there was definitely some other kind of business issues that were beyond just network. But I can say that like it was a lot harder going to this first conversations when you don’t have like a connectivity with the person. Well, after the way, like after working for four years in the Silicon Valley and building those relationships, those flow a lot more naturally, because now as a founder, your first customers is taking a huge bet.

on you, right? Especially in B2B, like what we do, like we were powering a critical part of our customer problem. Like if things failed, our customer product will fail. So getting somebody to actually make this better than you, I think required them to kind of know you before. And knowing that you worked on that specific problem before, then you know what you’re talking about. And I think there was no…

It is still very hard as you know, by doing this podcast, it’s always hard to get your first customer, but I would say it was significantly easier after we had that kind of trust networking place.

Paris Vega (07:35.71)
And you said it was about four years of working in the tech industry. Okay. And that was enough time to build up your network. So what did you do, uh, on the job while you were actively trying to build a network? Was it just literally doing your job, going about, you know, just doing your tasks or did you do things to intentionally build your network?

Matheus Riolfi (07:40.339)
I spent four years in Turo, that’s right.

Matheus Riolfi (07:59.989)
Both. I was definitely in a leadership position with the company. So by the nature of it, I was heading up international expansion. So I was running everything outside the United States. And I spent time in Canada, then in London. But I was always kind of like, you know, really in sync with everything that’s happening in the company and actually my day to day job, meeting like external partners, meeting the core team inside the company. So I think that is that is important.

have a job and have in a place that gives you visibility. But I was also actively looking for it. So I took the time to talk with a few investors as I was exploring ideas and now signaling to them that eventually I would like to start my own company and that’s why I’m here. So like you start building that relationship as well. So I did both internal effort, but also the external.

Paris Vega (08:56.75)
All right, and so when it came time to start Tint, the current company, talk us through that very early stage of what you did to get your first customers.

Matheus Riolfi (09:01.802)

Matheus Riolfi (09:10.705)
Yeah, I think what we do, we help tech platforms create their own embedded insurance products that protect their end users from the risks they are inherent to the car business. So for example, we work with YouShip. You can ship anything to their website, like a car, couch, whatever you want. All right, so you see the experience and at some point you’re offered to buy shipping protection because something can go wrong in the process.

Paris Vega (09:30.646)
just shipped a car through U-Ship recently.

Matheus Riolfi (09:40.301)
And then we help those tech platforms address those intrinsic risks so that now you can have a better experience as a customer. Right. And for U-Ship, they have happier customers, they can monetize this as well. So like, that’s how we’re done. And this is an idea that came while we were working at Turo. So at Turo, both Michael, founder and I indirectly or indirectly work on the insurance products that the company offer.

So we realized there was a great opportunity for tech platforms to embed insurance into their products, but we also saw how hard it was to do all of this without the proper help, the software, the service, the know-how required. And that’s why it was an inspiration to start Tint. So when we started to approach our first customers or trying to interview who could be our first customers, we were very targeted. We were working on something.

we built for Turo in a way, and now going to other people we knew in our network, in other companies, including Turo, saying, hey, what if we do this for you? Like what are your pain points? So we started really a discovery process, tried to understand, like we knew the direction, but we try to understand exactly who would do it. So our first step was LinkedIn, everybody that it was in the transportation space, which was where we initially started, that could use our product, and having…

as many phone calls as in coffee chats as we could to start seeing who would be interested in being our first customer.

Paris Vega (11:15.682)
So you said you started reaching out through LinkedIn.

Matheus Riolfi (11:18.573)
Yes, LinkedIn has always been my go-to platform. If I don’t have the person email directly, but I’d say for a lot of folks as they move jobs, it’s kind of hard to keep track of their professional email. So I use LinkedIn a lot.

Paris Vega (11:31.33)
Right, that makes sense. So when you reach out on LinkedIn, is it just using the direct messaging featured or do you do posts and content to try and pull, you know, attract leads? Talk a little bit more about that.

Matheus Riolfi (11:48.209)
Yeah, the time direct messaging, because again, we had an idea high level of what we wanna build, but then it’s like having a lot of one-on-one conversations to try to like unlock what are the pinpoints on that space. So we knew we’re going in embedded insurance space, we knew we were focusing on tech platforms, in our case, in the transportation space. So we kind of narrowed the search down to those folks, but if you’re going with an open mind and like asking more questions about…

their problems more than pitching a solution at the time. So it was all this kind of one-to-one relationships. And then eventually that evolved to even like to a proposal. Okay, I heard you, this is roughly what you’re trying to solve. We can build that for you. Let’s do a pilot or let’s get started. And then bring to get it to the first sales. And after the first sale, then we start like to like broadcasting a more standard message. Because at the time we know, we knew what we were selling.

But there was not until after we had, say, the first two to three customers up and running.

Paris Vega (12:52.706)
So when you were reaching out to the very first few, it sounds like you were doing or offering kind of a custom of more of a custom service. And so you were kind of scoping out a project and then building a solution that solved their problems. And then we’re able to scale that to serve lots of people’s problems. Can you talk a little bit more about that messaging for the first few customers? Like what did that?

uh first dm look like

Matheus Riolfi (13:24.197)
Yeah, so I do think that for the first customers, especially in the B2B space, you’re going to require some level of services and customization. And again, insurance is inherently a professional service. So we are using technology to completely reinvent insurance, but there’s always a service component involved to it. So in our case, again, we knew the direction, but within the direction, we will just…

listen to what are the pinpoints, what are the main things that they are trying to figure it out and try to collect enough like one or two or three cases like use cases they are similar, then we can start building for one of them because one of the key challenges of startups early days is that if you customize too much and you lean too heavily on services, then you never build a product and then eventually you are a service company which again…

Nothing wrong with that, but that’s a very different path than building a venture-backed startup, which was our case. We’re building a venture-backed startup. So you have to balance this kind of early customizations, which is always required. We’re trying to find commonalities in building a product and a technology to address those commonalities.

Paris Vega (14:22.231)

Paris Vega (14:26.855)
Yeah, it’s harder.


Paris Vega (14:42.638)
How many clients did you build custom solutions for at first before you were able to find those common patterns?

Matheus Riolfi (14:52.357)
I think our case was 10 or so. Yeah, and I think again, they’re all using the core technology, but they all had like different flavors and spins to it. I think it took us a good, like, and again, something about our business which can be different. We are on the kind of high ARR, like you know, six digit ARR model. So we’re selling more, almost like kind of, I wouldn’t say enterprise, but for larger.

Paris Vega (14:55.959)

Paris Vega (15:00.756)

Matheus Riolfi (15:22.325)
checks for larger customers. So that also impacts the kind of how you think about it. If you are in a business that like sells for $20 a month or something like that, then obviously you have to early on like get to some customizations because you will need hundreds of thousands if not millions of customers. Like in our case, I think our business can be very successful with a hundred customers that work well or 200. We’re definitely not going for the…

Paris Vega (15:34.774)

Matheus Riolfi (15:51.71)
thousands of hundreds of thousands of customers.

Paris Vega (15:53.634)
Right. Now that’s a very interesting point. Yeah, because the bigger ticket item that you sell or your plans are, that gives you a lot more room for the customizations and to, uh, deal with whatever issues the client may have, because yeah, you’ve got the revenue coming in to justify it. You don’t have to worry about scaling that quantity of customers early on. That’s interesting.

Matheus Riolfi (16:19.857)
Yeah, and I think that’s definitely one of the, and as founders, that’s kind of like, I don’t know, we started about like first B2C, see if it’s B2B versus B2B, the size of the ticket, like all those things are gonna influence how, and how we’re gonna do your first sales approach, right? Like in our case, our first contract with our customer was already tens of thousands of dollars, even when we had almost no product.

So that’s why in my case, I was emphasizing the network, the previous trust, like you need some, in order for somebody to kind of like sign that kind of checks and put their reputation on the line for you, they need to have a strong level of confidence that you can actually deliver, right? In our case, luckily we had that. We had our first customer was a former colleague that worked with us at Toro that had moved to a different employer.

And he had worked with us. He brought us in. We run a pilot. We could demonstrate the results on the pilot for the time the pilot was going. So it was a big risk for him, but it was much more digestible than if he had just met us two months before, and he would have to do the same.

Paris Vega (17:38.754)
So you raised 30 million in venture capital from Y Combinator and a few other investors. And that’s kind of like another type of customer in a way. You’re selling the investors, convincing them, pitching them. Tell us a little bit about that story.

Matheus Riolfi (17:57.905)
Yeah, so our ring, it’s similar in a sense, right? Like fundraising is sales. You’re selling a portion of the company to investors and they need to see the ROI. They need to see the same way that the first customer, the first customer, we need to be convinced that there’ll be an ROI, that you’re gonna create value that is higher than how much they’re gonna pay you. I think it’s the same with investors. They need to ultimately,

they need to be convinced that by putting a dollar in your company, it’s gonna grow, right? They’re gonna get more money out of it. So my approach was again, very similar, right? So as I mentioned, our first check, so our first customer as investor was my former boss, the CEO of Turo. So he knew us, he knew us, me and my co-founder, we both worked at Turo. He tried to convince me for a…

all of like five, 10 minutes to stay when I told him that we were leaving, but he knew me, he knew what I wanna do, and he was very supportive, and he was our first check. And then from there, he introduced us to our first institutional check, this investor called Web Investment Network, or WIN. So again, that was the beginning, and we raised our first $500,000 or so.

Paris Vega (19:11.854)

Matheus Riolfi (19:22.805)
through this process plus a few other members in that network. And that was our first step. So again, I think it would be hard to have the same process if I didn’t have that network and if I didn’t know those people beforehand or if I hadn’t actively built that by staying four years kind of working in a startup before doing the lip.

Paris Vega (19:47.57)
Right. So that relationship with the CEO became critical, it sounds like, in the starting of Tent, since he trusted you and you’d built enough, I guess, good enough reputation working there obviously to where he would trusted you with that first check and then introducing you to his own network. I mean, that shows a high level of trust.

Matheus Riolfi (20:08.601)
Yes, and he’s still a mentor. Now we keep in touch even now five years plus after I left. He’s still a friend, a mentor, and provide a lot of feedback to our company. So again, the network gives you more than the money or access, right? It gives you content. It gives you different kind of people to bounce ideas from. And I think that was…

really the beauty of the Silicon Valley, right? And in this model, this very strong ecosystem where former founders, investors, operators can all come together in large numbers and that kind of magic happens. I think with remote, this is changing a bit, but 10 years ago when I arrived in Silicon Valley, that was still the case, right?

Paris Vega (21:03.441)

Okay, this is good stuff. Um, what would you say would be advice for somebody starting a new company today, given the current environment we’re in the business world, we got AI coming up, shaking things up, um, you know, a lot more remote work. Um, let’s say somebody’s just starting out there wanting to get their business off the ground or they got an idea, they’re just getting started. What’s your advice to them when it comes to getting those first customers?

Matheus Riolfi (21:35.025)
Yeah, so again, not coincidentally, I would say lean into your network. Like try to figure out who are the people who know you that can be your investors, can be your mentors, and can be your first customer. Like again, as we discussed, depending on if it’s B2B, B2C, or the size of the check or the ER for, or average contract value for your company. But like, you know, try to take advantage

of that network. Like people say that even in the Silicon Valley, a lot of the first checks come from family and friends, right? And the reason is exactly that. Those are folks who know you, who trust you, because in the early days, as I mentioned, both from investors, the sale to investors and the sale to your first customer, it’s a bet on you. That’s really nothing in the early days. So that’s why it’s very important to…

And some people may have some apprehension doing this because they’re like, I’m not sure if the idea is gonna work and what if I fail, I don’t wanna let my family down, my friends down. But no, the reality is that can anybody that is involved in this venture game or in this startup game know that that’s a possibility and that’s okay, right? Like as long as you work hard and you’re learning and people will understand even if things don’t work.

Paris Vega (22:43.893)

Paris Vega (23:01.87)
Do you have any books that you recommend entrepreneurs to read?

Matheus Riolfi (23:07.994)
I do. So latency, zero to one from Peter Thiel, I think is one that I believe for kind of this very early moment of the first customer, it’s important. The other one that I like, it’s about challenger sales, which is a little bit more towards like later stage sales, but I do believe that one way you can add value, even in the early days, is like having a strong

viewpoint, the domain expertise on something and sell that as your first step into convincing customers to pay you, even if it is on consulting or something that can get you at the door and get started.

Paris Vega (23:52.303)
So with Tint, are you guys kind of leveled off? Do you have all the customers you need right now? Are you still growing and trying to scale up farther? Where’s the life cycle of Tint right now?

Matheus Riolfi (24:05.917)
Yeah, we’re definitely still growing. We are early stages to series A company. So there’s a long journey ahead of us before we are mature or we are stable. So it’s still in the fast growth, fast pace phase of the start of the company. But you know, the series A is the phase you transition from, like you talk about zero to one, we are now on the one to 10 journey, right? Like, so we’re closer to.

Paris Vega (24:13.887)

Paris Vega (24:32.701)
Okay. Gotcha. Okay.

Matheus Riolfi (24:34.097)
and then you get to 10 to 100, which is the kind of scaling phase. We are right in the transition between the two and it’s been super exciting. We’re about 50 people now. So we grew very quickly. We were four, like two and a half years ago or two years ago. So like it’s definitely been an interesting journey for us.

Paris Vega (24:43.959)

Paris Vega (24:55.136)
So as you’re going through this scaling phase, and you said early on you were focused on software platforms and the transportation industry, what’s your ideal customer profile now, your ideal target customer?

Matheus Riolfi (25:08.817)
It’s a true tech platform, but now we are mostly vertical agnostic. So we have customers in over 10 different verticals from transportation. We started like outdoors, your rider shares of companies on the kind of transportation sharing like to row or in the early days, but right now we have customers like you ship in shipping or deal, which is an HR platform. We have guests in vacation rentals. We have constant in the crypto world. So like we.

We’re now building a horizontal platform. So we were platform agnostic. And the best for us is like mid market. So series B, C, D. So a company that has already rich product market fit, has a certain scale, but it’s not too large yet. So we operate better in that space.

Paris Vega (26:01.406)
Okay. So it’s more about a certain company size and life cycle is the target at this point. Okay. All right. Well, this has been really interesting, man. I appreciate you making time for us today. Why don’t we close out by you giving kind of a pitch or just explaining the value of your service to that ideal target customer profile. If a thousand of those ideal customers are listening.

Matheus Riolfi (26:06.929)
That’s right. That’s right.

Paris Vega (26:28.042)
What would you tell them? Why should they sign up for tent?

Matheus Riolfi (26:32.553)
So the main value prop is that every platform has intrinsic risks, right? So again, if you’re shipping things, the things will break, right? Like, is it statistically speaking it’s gonna happen. So normally customers have this apprehension when they’re thinking about using a service and by launching embedded protection products, the company can turn that fear into value. So by say, providing a shipping protection that helps

the customer if anything breaks and they can increase the conversion of the car business. So their normal product becomes more attractive and they can also monetize that. So in case of Viewship, I don’t know if you noticed, but they sell the protection for an extra fee. So that can even become important profit center to the company. So what we’re seeing with our customers is a no brainer decision because you convert better your car business and you make more money. So those are the two main.

arguments and we make it everything so easy for them to implement and take care of the end-to-end experience that comes with very little lift on their side.

Paris Vega (27:41.196)
Awesome. Okay, so if you’re a tech platform out there looking for another way to make a little extra money and offer insurance to your customers, you can reach out to Mateus and he can get you set up. It’s a really cool, really cool business model.

I was trying to think if any of the things I’m involved with could use it, but I don’t know if we’d be considered a mid-market tech platform. We’re not that big yet, so we got a little ways to grow.

Matheus Riolfi (28:07.889)
Yeah, we’re happy to talk with any founders. And even if it’s not a good fit for whatever reason, like we always help founders, we send them the right way. Like as you can imagine, I’m very excited about talking to founders and any new ideas that are happening out there.

Paris Vega (28:17.737)

Paris Vega (28:26.542)
Cool. Well, thanks for sharing your insights with us today, Mateus. And everybody listening, reach out to Mateus. Reach out to you on LinkedIn or go to your website.

Matheus Riolfi (28:37.085)
That’s, yeah, that’ll be the easiest place. That’s right.

Paris Vega (28:41.458)
All right, we’ll see everybody next episode later.

Matheus Riolfi (28:45.257)
Thank you very much, bye.


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