How did you end up even becoming part of the insurance industry?
SPEAKER_01I happened to be a really avid drone pilot. And so when I talked to the other drone pilots and they said, damn it, like I got this great job at you know from Fox or from Sony Pictures, but I can't get it because I don't have the insurance. I knew that there was an opportunity, and so that was some a problem that we could solve, and it was one that I knew something about.
SPEAKER_02You talked about building the team. What were some of the things that you did when you were doing that?
SPEAKER_01The first thing is we were very disciplined and specific in how we built the business.
SPEAKER_00What would be the number one piece of advice for the entrepreneur, insurance agent?
SPEAKER_01In an industry like this, the first movers actually wind up doing a lot better than people that say, okay, things are going great, and let's just wait a couple years to see how that kind of pans out. Being an entrepreneur, I mean, it's about endurance, right? Like things never go right. Never, ever, ever go right. I guess the difference between the past and today is I recognize that. I accept it. And so basically what happens about the price.
SPEAKER_02I don't know if you've listened to the show before, but everybody gets to run. Oh, okay. Well then you've you may have prepped a little bit. You may have a under pass, pass. All right. So time on the clock. Let's go. Jay, have you ever had a mullet? No. First crush. Mom ever caught you doing? She's too dirty for this show. Yes, perfect. The fastest speed ever driven. Uh 120. Nice. That's that's respectable. Favorite cereal. Uh so Bob's red mill muesleigh. Ooh. How many kids? Nice. Have you made a cry? Love it. You did wait for the count chocula or count Dracula? Count Dracula. And the fastest smile. That was my Dracula impression.
SPEAKER_01Oh, yes, yeah.
SPEAKER_02Fastest mile.
SPEAKER_01Oh, my fastest mile. Yeah, you're saying let's say um eight minutes.
SPEAKER_02Okay. Favorite flavor? Nice. Butter pecan? Dogs or cats. Dogs. That's correct. Tacos or burritos? Burritos. Favorite video game. Command and conquer. And it still always comes up, Trump or Biden. You don't have to answer it. Pass, correct? Awesome. And I'll toss it over to Jason and then we'll dive in.
SPEAKER_00Yes, Jay. What was the first concert you ever went to? All the way back to Barney.
SPEAKER_01Grateful Dead, Madison Square Garden, 1992. Oh, well, that's very interesting. Nice. That is very interesting. What year? What is it?
SPEAKER_021992. 92. Fat Jerry.
SPEAKER_01It was the full band. It was uh, you know, the full experience. Uh, I was still in high school, but uh it was yeah, it was a great first concert. Who um who was on keyboard?
SPEAKER_02Don't remember. Remember? No. I think it was Hornsby. It might have been Hornsby. Does anybody know the keyboardist? Is that well, there's with the dead, there's a whole thing about the keyboardists. It's like that that means you're on deck to die if you're one of the keyboardists for the dead. So very storied uh thing about that. So why don't you take us back? Uh you're you got a great story going all the way back, but how did you end up even becoming part of the insurance industry? Let's dive in there.
SPEAKER_01So, my last business, uh, so I've started a couple of businesses in my career. I've been a career entrepreneur. Um, and so my last business was a ride-sharing company in London uh called Halo, uh, and that was eventually sold to Daimler. Uh, and so one of the things that I noticed while we were building that company was just how differently small businesses were being created uh through the use of technology, predominantly mobile technology. Uh, it wasn't just this idea that you were, you know, you got to get a Main Street shop and a couple of employees and an annual insurance policy, and you're kind of good to go. You were dipping in and out of basically uh, you know, creating something, a lot of times just doing business on your phone. So I thought, well, look, what is going to be the blocker for this future to come true? And one of the things I kept coming into when I talked to people was insurance. Uh, you know, and so insurance wasn't changing with the times for this new breed of SMD and this new future of work to actually get realized. And so I teamed up with a friend to figure out how to solve that problem. Awesome. So take us.
SPEAKER_02What problems were you running?
SPEAKER_00Yeah, there you go. Yeah. Well, what what was the what were some of the problems you were running into uh with insurance specifically?
SPEAKER_01Yeah, so so some of the issues are, you know, the purchase process. You know, an SMB, it can it can be just a single person, uh, you know, now they're basically consumers, they're not used to the way in which uh small business insurance is presented traditionally, which is oh, here's something that's designed for people who have between five and 50 employees, and it's got 45 questions, and it takes you an hour for the broker to walk you through and complete. And then, oh, if you want any changes to it, you got to call up the broker, they'll call up the uh you know the service center of the insurance company, uh, and and you'll go through that entire chain to get uh you know to get an answer back. I mean, it doesn't work for the consumer, but it also doesn't work for the broker because they're gonna do a ton of work to arrange and bind a pretty small policy, you know, three, four hundred bucks. And then after they do that, then they've got the customer ringing them every week with a new client, adding an additional insured, and all of these things that they should be able to do themselves, but previously to Thimble, they couldn't.
SPEAKER_00Crazy. That is a huge problem. I've I've actually ran into that uh a few of my friends starting small businesses, and our agency doesn't really specialize in that. So we we pass them off to somebody else that does it. And yes, it is time consuming. And anytime that there's changes, that agent is uh bogged down. So interesting. So yeah, talk about so you have a buddy, it was he an insurance agent?
SPEAKER_01He was not, he was far from an insurance agent. Uh, you Eugene uh was somebody I met 10 years ago at Halo. He was a technical consultant, he's brilliant. Um, but he's he was he had been an entrepreneur too. He had co-founded a business called diapers.com uh that became hugely successful and was sold to Amazon in 2011. He was the chief technology officer. Uh so uh at the time that I got him, he was retired, but potentially interested in doing uh other things. And we got together talking about this as a really hard problem, both a tech problem and a product problem and a people problem. Uh and so we we got together and started to build a team um a couple of years ago.
SPEAKER_02I I think it's so interesting to dive into the the whole notion and idea of that entrepreneurial part of being an agent and having to come in and actually build the business. A lot of times agents will come in and then want to be the one-man band, and then it's not scalable, right? They they run into a a lot of there's the learning curve of trying to learn everything. And then also they just you you can't you can't grow if if if you're doing everything. So I think it would be relevant to talk about the building, like you know, from the beginning, how did how did you put it together? What how did you identify? You talked about building the team. What were some of the things that you did when you were doing that? And then take us all the way up to funding because I think that's a real interesting piece of it too.
SPEAKER_01Well, look, so I mean, the first thing is we were very disciplined and specific in how we built the business. So we we first started out with a very with one single uh type of profession, uh, which happened to be uh commercial drone pilots. Because at the time there were all these drone pilots that were just starting to build their business, uh, but they didn't want to buy annual policies, they wanted to buy perfect policies, and that wasn't available on the market. Drone insurance was a really new thing anyway. Uh so we built the perfect system and app for commercial drone pilots. We did it on an admitted basis, it's approved in all 50 states. Uh, and so when we learned how to do that, we learned everything about how to create an admitted insurance product in America, all the people we needed, all the products we needed, all the discipline we needed on the tech side. Um and so that was sort of the the kind of you know, the the precursor to uh Thimble, which was okay, now let's expand this out to 500 different types of business, um, and then let's do a thousand, and then let's do more and more and more, uh, and let's build something that um you know that can really uh scale horizontally and vertically.
SPEAKER_02So love it. Love it. And you went out, did how did you select which which specific uh different business businesses to target? You said five.
SPEAKER_01That was more of a kind of um, it was uh you know, uh not as scientific. I happened to be a really avid drone pilot. And so when I talked to the other drone pilots and they said, damn it, I'm like I got this great job at you know from Fox or from you know uh at Sony Pictures, but I can't get it because I don't have the insurance. Uh I knew that there was an opportunity, and so that was some a problem that we could solve, and it was one that I knew something about. Um, and it was so new that people wanted that that kind of problem to be solved. Um, they didn't think it was solved already.
SPEAKER_02So you basically you you've sort of created like an invent an event insurance policy, but for the drone pilot.
SPEAKER_01Yeah, you could say that. And actually, it's funny that you do say that because one of the new thimble products that's not out yet but is coming out is actual event insurance you can buy from your phone. Um, with just like a couple of questions, super easy, super easy to modify, super easy to email the COI to you know the venue. And this is something that's not just built for direct to consumer, it's actually built with agents in mind too. Uh so you know, agents can buy these policies from our platform for the consumer and they can access all the self-service, uh, or they can even just send a link to the customer and get full commission when the customer signs up. So we've kind of built this with the agent in mind.
SPEAKER_02Which is awesome because a lot of these policies, especially for captive carriers, that you go through a secondary platform and it it's it's pretty, you can get down the rabbit hole trying to put everything together. And a lot of times, like what Jason said, it's like, ah, I just send it over to somebody else, right? Because it's just it's it's way too much work to make 30 bucks, right? It just doesn't make sense. So to have that in your back pocket, I think is huge. And it's an it's a it's like the gateway drug, right? You can you can offer this to get folks in the door and then talk to them about their home and their auto and all of the other things that we talk about.
SPEAKER_01Absolutely right. I mean, the the the we we have 7,000 plus agents that are using this system and and you know they're doing it because of the the speed and flexibility, uh, you know, and control that they're getting from it. Uh and they like to sign up the customers because then they have the customers on their books and basically they can prospect them in the future to their liking, but they haven't done a lot of work to be able to do it, not at the expense of other things in their business. We we know that uh, you know, everything always comes at the expense of something else.
SPEAKER_00Let's just say my agency, if my agency signed up with Thimble, um, I'd be able to send out it's almost like an affiliate link, right? Where it's like they sign up directly with the company and I would see a portion of the commission.
SPEAKER_01Yeah, absolutely. And they would see the commission. They could either download the app uh and do it, and we can track it right through the app store, or they can do it uh on on the web. Um and and then you'll get notified as soon as they actually sign up, you'll get an email that says this customer signed up, uh, here's all the details, etc. So it it's it's really pretty seamless. Um and by the way, the the customers love it because from the customer's perspective, it's still so much easier. And a lot of the customers they love systems where they don't have to talk to as many people as uh you know uh as they might have to traditional.
SPEAKER_02Especially for these smaller transactional things, right?
SPEAKER_00Exactly.
SPEAKER_01Right, yes.
SPEAKER_00Can you webhook data into Thimble?
SPEAKER_01Yeah, we can. So we are we are partnered with Angie's List, um, a company called Peerspace, uh, which is a big in the event space, uh, and about a dozen others. And we actually have a full API that allows them to uh to offer insurance to their pros. Uh we also have, by the way, we have a widget for uh brokers uh that is actually um uh on a significant number of websites where basically the agent can just take our um uh kind of code once they sign up, paste it into their website, and then there's a little booking platform that gets embedded where the customer can just sign up right on their website and it looks exactly like part of their website. And as you said before, get a percentage of the commission uh that flows through that.
SPEAKER_02And then you could webhook some of that info over to your CRM and then create automation.
SPEAKER_01Yeah, uh as you like.
SPEAKER_00Love it. Uh that reminds me of the David Carrers conversation where he had the uh he had an event insurance and he used that as the front end of his of his sales funnel, in which he would pretty much break even on the front end, uh run pay paid ads to it, break even on the front end, and then be able to cross-sell on the back end. So awesome. That is, I love it. I love it. Huge opportunity, I think, for insurance agents to jump on and be able to um use it as a as a huge tool and time saver of something that's not the best use of our time, especially when you're switching over those uh event insurance is nuts, man. Like it's so little. And some people are you know, at SWAT meets once a week or the four events a week, and they're constantly changing all that stuff. It's crazy. And it is a huge pain point for the for the person too. I know one one of my buddies was doing that. He was doing um uh farmers markets and stuff, and he kept having to get this, get get the insurance and changing the info and and the the time. It it wasn't even so much as the pain with the agent. Um, so I send it to my agent buddy. Uh it wasn't even so much the I mean, there was a pain between the agent and him, like time-wise, but the real pain point was was the time that like if he could just fulfill it in a uh on an app or something, he would do it. Like it would eliminate the need to even talk to the to the other dude. So that would have been huge. Absolutely. We'll get him on it.
SPEAKER_02Yeah. Well, you know, like agents, agents kind of back to what I was saying before, they they think that they that it serves themselves by helping as many people as possible with as many things as possible, and it just really bogs everybody down. And and if you're looking at at something that, you know, a couple hundred dollar policy, you're making 20 bucks, and and and now there's these multiple additional insured changes and printing out certificates. I mean, the cost of of trying to manage something like that is is incredible versus what you're bringing in. And just to be efficient, this is a really, really interesting tool that I think uh folks should be looking at. So, how would somebody go about finding the app, uh going to the website, learning more? What are all the details?
SPEAKER_01If you go to thimble.com or thimble.com forward slash broker, uh, that has uh all the information. You can also, if you want to play around with the app, which a lot of agents do, uh you just search for thimble on the app store. Uh, we're actually the only app that allows you to buy and manage business insurance. Um yeah, believe it or not. Cool.
SPEAKER_02You can bind it right there on the uh app?
SPEAKER_01Yeah, about 30% of our customers actually bind it directly on the app.
SPEAKER_00Wow. Super cool. Do you have to be an agent to get the affiliate?
SPEAKER_01Good question. So so actually, no. Uh so we have two levels. We have a kind of a referral program where basically you get all of the benefits, including commission, uh, but you don't have to be appointed. And then we have uh an appointed program, which we've just started right now, uh, which is basically allows you uh some additional functionality features and commission rates that aren't available uh on the the uh regular system. But uh we can do both, is the bottom line.
SPEAKER_02And there so that and then you guys are the underwriter or who who do you who writes the yeah?
SPEAKER_01So so we uh so uh we are an MGA, we use uh State National uh paper, which is part of Markel Group. Uh and Markel is uh our reinsurer. So Markel Group is is uh Marcell Ree is 100% reinsuring uh all of our work. So it's it's really good paper um with a really solid partner.
SPEAKER_00Nice, super cool. Jay, I want to dive uh a little bit backwards and a little bit deeper on. So you you've been a part of a few different startups that have been um very successful. What have you learned throughout the years that have that has been able to expedite uh I would say thimble more so than some of your earlier ventures?
SPEAKER_01Yeah, well, look, so uh, you know, I think it's more of understanding that uh these things take a long time to build right. Right. Like you really want to build things. In the beginning, I think I was more uh, you know, more thinking about how do we build to be able to sell the business or how do we be able to build, you know, build it really quickly for a reason to be able to somehow flip it. Um and now I you know I think about building for the long term and building value and infrastructure and everything for the long term. But you know, look, being an entrepreneur, I mean, it's it's about endurance, right? Like things never go right, never, ever, ever go right. Uh it is it is an amount of time that that they go right. Uh the rest of the time, uh, you know, they go wrong in in spectacular ways. Um but uh uh but but I I guess the difference between the past and today is I recognize that, I accept it. And so basically when it happens, I'm not surprised.
SPEAKER_02I think that is very, very wise right there, because it is sorry to cut you off, Jason. But I mean it is it is a hundred percent true, right? There's always something that goes wrong, and then it's like, okay, it's this today, and you just have to go with it.
SPEAKER_01Yeah, and I look, I I empathize with with all of the agents out there who are entrepreneurs, you know, with their own businesses, because I mean, anything can happen. Staff can leave, you know, uh markets can change. You know, it's just there's any number of things that can happen that are totally out of your control. Um, but you gotta ride through uh and and uh you know get to the other side.
SPEAKER_00What have what has been some of those things that uh has given you endurance, especially with all the, I mean, I'm sure you've had your back against the wall many times throughout your your time.
SPEAKER_01Well, look, uh so you know, I I think there is the the belief that is kind of now ingrained in me that things will get better. They might not necessarily get better tomorrow, but if you keep having the best team, if you keep having the best product, uh, you know, if you keep having the best partners, um that over time, you know, things will go your way. Uh and I think that that's really all you can hope for. Um, everything else is just noise.
SPEAKER_00Love it. Love it. Um, so this is the big final question. Um, everything that you've learned with throughout your entrepreneurial journey, and then everything that you've seen with insurance agents since you've uh been on your journey with Thimble, what would be the number one piece of advice for the entrepreneur, insurance agent that's either been in the industry for a while or somebody that's coming into it and really wants to grow their business?
SPEAKER_01So, you know, I I guess from what I can see, uh, you know, insurance is a very complex uh kind of sclerotic uh you know industry. Uh so uh, you know, you you really gotta go and roll with the uh the punches, but also you've gotta, when new technologies or systems arise uh and you know come about, you you can't be afraid to be the first or among the first to seize on them. So I think basically in a in an industry like this, the the first movers actually wind up doing a lot better than the people that say, okay, things are going great, and let's just wait a couple of years to see how that kind of pans out. Um because the market, the the insurance might might not be changing that quickly, but the underlying customer um dynamics in a lot of cases, how people buy insurance is changing pretty radically. And so I think as an agent, you have to figure out how you're gonna be ahead of that curve. And I think you're in a great position. You know, all this insure tech can be your friend, can be enabling you uh to do better than you have ever done before. I mean, have us work for you. We have tons of product managers and engineers that are working to make life easier for for you. Uh so just embrace that.
SPEAKER_00Love it. It's like it's like Batman's utility belt. Build it. Get a bigger belt.
SPEAKER_02Awesome, man. Jay Bregman, thank you so much uh for jumping on. And one more time, uh, it's Thimble at available at the App Store and the website uh for the listeners.
SPEAKER_01So thimble.com and thimble.com forward slash broker.
SPEAKER_02Okay, and then your cell phone in case anybody has any tech issues.
SPEAKER_01You can email me anytime at Jay at thimble.com.
SPEAKER_02Awesome. Well, thank you so much. Uh, it's been awesome to have you on, and we look forward to checking in down the road. I love that. Thank you very much. Okay, see ya. Well, thank you, Jay.