Dennis Li With Reeske

Intro: [00:00:00] Welcome back to the Startup Showdown podcast, where we discuss pitching, funding and scaling startups. Join us as we interview winners, mentors and judges of the monthly $120,000 pitch competition powered by Panoramic Ventures. We also discuss the latest updates in software Web three, health care, tech, fintech and more. Now sit tight as we interview this week’s guest and their journey through entrepreneurship.

Lee Kantor: [00:00:39] Lee Kantor here another episode of Startup Showdown podcast, and this is going to be a good one. But before we get started, it’s important to recognize our sponsor Panoramic Ventures. Without them, we couldn’t be sharing these important stories. Today on startups, on startup shutdown, we have Dennis Li with Reeske. Welcome, Dennis.

Dennis Li: [00:00:59] Hey, thanks for having me. Glad to be here.

Lee Kantor: [00:01:01] Well, I’m excited to learn what you’re up to. Tell us about your startup.

Dennis Li: [00:01:06] Yeah. Yes. So we are in short tech companies and we redefine how millennials protect their money using embedded insurance with AI.

Lee Kantor: [00:01:17] So if they’re not using your service, what are they doing or are they doing anything?

Dennis Li: [00:01:22] Great question. So that’s a problem, right? When you look at the broader picture, millennials, personal finance today is very fragile for an average person. We estimated three quarters, 75% of their income is subject to unprotected risk like death, illness, disabilities, all these horrible stuff. You know, a small portion of people choose to buy it from a traditional broker and agent. But most people just involuntarily choose inaction just because there is no good digital solution to do it. And we’re here to bring insurance to everyone and make it accessible using data.

Lee Kantor: [00:02:00] Are you communicating with these millennials directly or do you use intermediaries?

Dennis Li: [00:02:06] Yeah, great question. So we actually access these millennials through fintech company. So our business model where B2C. So we empower B2C, fintech companies who offer income protection insurance. By that I mean life insurance, disability insurance and critical illness insurance and all that. You know, non-compulsory product, complicated product. We access customer through through these channels.

Lee Kantor: [00:02:34] So what was the genesis of the idea? How did you come up with this?

Dennis Li: [00:02:38] Yeah, so I didn’t really come up with it because before I started Risky actually live and breathing insurance for nine years I was an actuary, so we actually built products, insurance product from the ground up. But what I realize is, you know, product innovation is great, but when it comes to insurance, we’re not there yet, meaning that we struggle even as a big company to access customer economically just to be getting in front of them when it gets to digital channel, it’s a huge challenge. And the second thing is, you know, even if we get in front of them, how do we convey the value proposition now without like a broker, an agent to kind of walk them through? So it’s really these two barriers we need to get over first before we think about developing new product. And that’s really what risky set out to do to solve the distribution inefficiency problem and also the customer engagement problem using, you know, the newly available technology and the data.

Lee Kantor: [00:03:42] Now, I would imagine that this is an interesting time when it comes to insurance. There’s so much information and there’s so much availability for a person if they wanted it on one hand, right? It’s all there. Everything’s there. But then it’s just almost overwhelming. Or they’re thinking about things they don’t want to think about, so they just kind of either put it off or they ignore it.

Dennis Li: [00:04:05] Yeah. Spot on. That’s the problem we try to solve. You know, up until today, in the past five or six years, the way life and health insurance company tried to try to market digitally is mostly direct to consumer. But, you know, you just talk about the challenges, right? It’s very hard to use advertisement to get people to just all of a sudden think about insurance. You know, it’s very hard to convert people that way and it is also have anti selection. So most people end up buying life that will be poor risk. Right. So it just it’s just a really leaky funnel at many levels. And, you know, we’re trying to come in here and figure out where are the customer today. Right. They are looking for insurance. These are necessary evil. You know, insurance is always something that people have to think about. But where is a place that people already thinking about insurance? They already trust the customer. They already trust the brand. So being part of that, right, being part of that, to engage with customers and also provide a level of personalization to be more efficient in conveying value proposition is what we do and what we do very differently from other other companies.

Lee Kantor: [00:05:20] Now, let’s talk for a second about your journey. You mentioned being an actuary insurance, kind of seasoned insurance veteran. How did you kind of make the leap into a startup which, you know, the talk about risk, you know, that’s not for the faint of heart for somebody who’s so numbers oriented. How did you kind of wrap your head around the risk of kind of founding a startup and doing something like that? Because that seems it’s not for everybody.

Dennis Li: [00:05:55] Yeah, that’s always an interesting topic because I’m an entrepreneur. Coming from actuarial background is still rare and every time I meet one it was it just makes me smile. Right. And I think, you know, even since I was young, I always like to build stuff, you know, I always really creative, want to solve problems, you know, just throughout my, my, my, my journey, I’m always trying to find these opportunities. And when I get into college, I started to learn about insurance. So I didn’t really know anything about insurance before college. And that just really get fascinated about how much legacy Bowdoin has, how much you know, because it really touch upon multiple subject right is finance is you know, it touch upon behavioral psychology. So all these things really just get me fascinated. I started my career as an actuary. You know, I work in different functions finance, building, product, technology. So it just allow me to see where exactly the market gap is. And at some point, right. I understand that if I want to, you know, have a bigger impact, I it’s very challenged. I’m very challenged to do that in a big corporation. So just have to pull the plug at one point. And, you know, starting the beginning of last year, it was just the right time. It was just the right time. So I just did it.

Lee Kantor: [00:07:21] Can you I’m just trying to dig in here a little bit more in terms of for folks out there that may be in the back of their head, they’re like, you know what, I’m entrepreneurial. I’d like at some point to do this, but I’m in a pretty secure spot here. I feel pretty good. I’m kind of moving up the ladder. Yeah. Did you can you share a little bit about how you did the math of this, the trade offs back and forth on, you know, you had this itch you wanted to scratch, you saw this gap. And, you know, obviously you pulled the trigger and went for it. A lot of folks struggle with taking that leap. Can you share some of kind of the the the mental gymnastics you did to get to the to where you are today?

Dennis Li: [00:08:04] Yeah, for sure. You know, I think it’s all about individual’s priority, right? I think for me, just solving interesting problem. It’s on the top, right. And I’m also enjoy uncertainty. I think that’s one of the key elements. If you want to be successful in entrepreneurship or an entrepreneur journey is, you know, if you are if you thrive in uncertainty. Right. And this journey has been great so far. It’s very exciting, but definitely not every day. It’s good news. A lot of times there’s bad news and sometimes these good news and bad news will not one hour apart. So my point is, you know, I started to understand myself a lot more even before I started to started this journey. And I knew that I would I would enjoy it and it will give me a great opportunity to solve interesting problem, you know. And of course, there’s always opportunity cause. Right. And understanding that and make. Make a decision. I think there is no magic pill behind that. But just understanding what you prioritize, who you are, what you’re good at, and use all these data. So it’s still a data driven decision, but, you know, it’s also a a judgment element in it.

Lee Kantor: [00:09:23] Now, you mentioned that this is B to B to C, are you having a difficult time reaching the other B involved, the intermediary in order to explain the offering and the value proposition? Or did you start talking to those folks early and then get a hint that, hey, we’re going to be able to leverage this and this? This could work out?

Dennis Li: [00:09:47] Yeah, it happened a little bit. Both. So we definitely didn’t land it at this distribution channel right off the bat. Wish we did. But we actually went through a lot of iterations. You know, we we understand that to access customer, we have to go through an intermediary. That’s a fact, right? Because direct to consumer is just very challenging for the product we’re trying to distribute. But the next question is what intermediary makes sense, right? The unique challenge of B to B to C is that we have to provide value to both B and C to have a long term mutual success. There has to be alignment of interest. Timing has to be right. And also both parties have to be willing to move at the pace that that that makes sense to each party. So in the beginning it is challenging. But, you know, once we gaining more exposure in the space, once I understand the channel a little bit more after we landed at this fintech channel, just after having a lot more opportunity to have those direct conversations with the founders, the customer discovery session almost naturally organically turned into a sort of a sales process because I realize a problem is the one that we’re addressing so perfect, right? So that’s sort of how it unfolds right now. We are pretty small team. I’m leading the effort in growing the business. So yeah, looking forward to to to really expand our go to market team and get some sales superstar on board.

Lee Kantor: [00:11:20] Now how did you hear about start of shutdown in panoramic was that you know how did they get on your radar.

Dennis Li: [00:11:28] Yeah. So one of our mentors in the Atlanta area actually mentioned panoramic to us. So I check you guys out. I was pretty intrigued by the thesis and the mission to to help founders overlook founders, first time founders and for the showdown event. I always love these types of favors, so it’s pretty a no brainer for me to sign up. And after all, it’s a really well-organized event. So kudos to the.

Lee Kantor: [00:11:56] Team now having gone through what were some of the things that you got out of it? What were some some things that were most beneficial to you?

Dennis Li: [00:12:06] Yeah, I think the whole experience was quite fun. I enjoy meeting other founders, sharing our mission and bringing awareness to insurance innovation. Right, because it’s a it’s not a very fun topic for most people, but important topics. So, you know, often fell off people’s radar. So I like this all kind of opportunity. Also enjoyed the competition element of it. I think most founders like it in terms of, you know, learning other people’s business and sharing their mission.

Lee Kantor: [00:12:36] Now, you mentioned a mentor. Has there been a lot of mentors for you kind of guiding your path? Is there any startup founder that’s out there that you’re kind of looking up to, that you’re trying to emulate or, you know, whether you know them in person or you just heard about them? Is there someone you go to for advice and inspiration?

Dennis Li: [00:12:56] Yeah, we have a very strong supporting system behind Risky, so that’s something I’m really grateful of. They are, you know, insurance executives, business leaders, and there are some ex operators as well. I think, you know, there are a lot of names of people I look up to. But those are instrumental, right? Because as a first time founders, I don’t know what I don’t know. Right. And most of the time, I think when startup didn’t work out, it’s not necessarily because founders lack of any skills, but because of strategic planning, right? Things. They haven’t get to the point they need to get to before they run out of money. So just talking to people and having these experienced folks behind us, pulling us away is instrumental.

Lee Kantor: [00:13:44] Now, has there been maybe a mistake you made or some setback that you were able to get through that propelled you forward? Because you mentioned iterating the intermediaries a bit. Can you share a little bit about how. Because that’s always hard. You know, everybody it’s not a straight line. It’s ups and downs, but. Sometimes the downs really are a blessing in disguise that that helps catapult you to a new place because it opens your mind to a new opportunities.

Dennis Li: [00:14:14] Yes, I think there is a lot of there’s a lot of learnings throughout the journey. One thing that’s been particularly helpful is how do we do customer discovery? I think in the beginning it’s a common issue. I heard from founders just talk too much, right? We have our hypotheses. We try to sell before we learn. And I think being a good listener, like an active listener throughout the session, really gave us insight into what’s the real problem out there. I think in the insurance and fintech ecosystem, everyone hold a piece of the puzzle to solve this, to solve this, this problem we’re trying to solve. And our job is to put it together. And to do that, we have to be able to listen well and, you know, not letting our sort of bias or hypothesis like, you know, overshadow what’s the truth out there.

Lee Kantor: [00:15:13] I know it’s hard, though. That takes a lot of self-discipline because you’re so excited about your solution and you want everybody to know about it. But really, maybe the first step is just being a good, active listener. Hearing their challenges and their frustrations and then seeing if you can elegantly fit your solution in there is probably better. You’re better served if you can pull that off for sure.

Dennis Li: [00:15:37] Yep.

Lee Kantor: [00:15:37] So what’s next for you guys? How can we help?

Dennis Li: [00:15:42] Yeah. So right now, you know, we’re just moving forward full speed. We’ve grown the business in terms of partnership, building out the right team and of course, you know, get to work with investors who share the same mission really in democratizing insurance for everyone. So, you know, a full plate here. But yeah, we’d love to talk to any investor right now. We’re still trying to close a round of the seed round right now, so we’d love to get in touch with people who are interested in solving this problem and innovating insurance distribution.

Lee Kantor: [00:16:17] And if somebody wants to learn more, have a more substantive conversation with you or somebody on the team, what’s a website?

Dennis Li: [00:16:23] Yeah, so you can reach me very easy. Dennis Dublin is at Risky, Risky dotcom, so we’d love to hear from you and bounce ideas.

Lee Kantor: [00:16:35] Well, Dennis, thank you so much for sharing your story. You’re doing important work and we appreciate you.

Dennis Li: [00:16:39] Thank you for having me.

Lee Kantor: [00:16:41] All right. This is Lee Kantor. We’ll see you all next time on Startup Showdown.

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