Jeff Arnold - Founder at RIGHTSURE

Welcome to another Founder Wisdom Pod. We have Jeff Arnold with us today. He's the founder at Rideshare, is a 5-time bestselling author in the Tucson area, has a very intriguing background. So we're going to get right into it today. Jeff, welcome to the pod. Tell us a bit more about yourself and what you're up to.

Hey, thanks so much, Charles. Super happy to be here. Wow. What I'm up to. Let's start with that, because that is way more engaging than people hearing about me. Right. So Spending most of my time writing and speaking for leaders in a specific vertical and genre, and that is how to be thinking about deploying AI into your company. And why I spend so much time there, all of my time there, is as leaders and company founders, everyone is looking for an edge and everyone is wanting to adopt AI, infuse AI, or say with messaging that they have AI. And my caution, my counsel, my guidance to them is, yeah, absolutely lean into that and be tech forward. But there's a much more critical and disciplined way to think about leadership when you're deploying AI, right? For example, if two companies have the same tech stack and can deliver almost identical responses in time and product and pricing, The one with a better culture, the one with better leadership, is the one that's going to win. And so, uh, without going too deep into it, I help leaders, train leaders in several of my books to think systemically, critically, and with discipline about how you're going to deploy AI. Not just grab the first piece and add it to your tech stack or launch forward. How can it help your company move forward and meet your growth objectives.

And you've been in the insurance space for what, 30 years now? Your first company was Western Pacific Insurance Brokers. Tell me a bit more about your long career in insurance.

Absolutely. I want to be somewhat succinct. I don't want your listeners' eyes to glaze over, ears to close, because when they hear the word insurance, people just instantly disconnect. I understand that. So I would submit this to your listeners. Think in terms of legal contracts. The legal contract that you buy, you think is all the same and based upon price, but just like anything you buy, what you pay for you get, right? Or you get what you pay for. And so, uh, we've spent our career in RightSure, which is North America's most awarded insurance firm, explaining to our, you know, hundreds of thousands of customers, uh, the difference in legal contracts. And so we don't really fancy ourselves an insurance brokerage. We're famously friendly humans helping people buy the right contracts. But to deepen that, yeah, before RightSure, I've, I've bought and sold 40 different insurance brokerages. I've run an insurance company as a president, and I've run a managing general agency for Mexico and North America for just auto insurance. So been in this vertical, or this, uh, profession of legal contracts, for about 34 years.

And I mean, I don't, um, I find interest in insurance, like me personally as a good old capitalist, right? Um, I think most people don't, but to me I can see the, the money, and I consider insurance companies like almost banks in themselves, right? They calculate risk, they're masters at calculating risks. Um, what have you learned from your time in insurance and how Did you not get bored? What was the reason for you to stay that long in that industry and still?

Oh yeah, I think like any industry that anyone is passionate about, you'll find something to re-engage you, re-recruit you, make you return to your roots, kind of. I certainly have diverted. I've owned some semi-pro and had franchise in pro soccer teams, football, real football and soccer teams, and then been involved in some fintech. Startups. The reason I keep returning to insurance is, uh, kind of alluding to what you said, Charles. I think of it in terms of banking, right? In, in terms of risk transfer, you know, not just selling but also personally transferring risk to another party based upon a very small amount of money, which we call a premium. Now I understand consumers think those premiums are sometimes expensive, but I have a contrarian viewpoint on that too. And really briefly, if you think about the foundational promise or premise of the legal contract called insurance, most people want it for claims or to get their money back. But everyone, the entirety of humanity, forgets this: the very first thing that you get from insurance is a company that steps in and provides guarantee of something you can't pay cash for. What I mean by that is you want a fancy luxury car or a car that you can't pay cash for, insurance company just steps in with the contract for pennies on the dollar, a premium which some people think expensive, and say, yes, go buy this thing that you can't afford to pay cash for. Alternatively, additionally, the same goes for everyone's largest asset generally is their home. Right? You can't pay cash for a home. You want to buy a mansion. The legal contract of insurance, you know, the contracts that writesure sells, step in and make people whole with the bank for literally pennies on the dollar. And that's the number one benefit of insurance. But most people come to just accept that and look for it at the claims time. They forget that the first bite at the apple is always, yeah, they get something that they couldn't pay cash for. And they get to spread it out over the lifetime of the asset.

And definitely see the value of that. And I think insurance companies, you know, they're in the business of providing peace of mind as a service. Right. And just that in itself is a value because humans are stressful creatures, right? Like we always stress and have anxiety about pretty much everything and when a company can handle that part, it gives you more bandwidth, more energy, and that in itself is money, right? Like, you can invest that, that energy in other, uh, things and live a better life. And I think that's what— that's the main value, in my opinion, of, uh, insurance company, even if shit doesn't hit the fan, right? So I think it's a wonderful industry. I think it's, uh, it's great companies as well. Where do you see that shifting with, um, AI, uh, do you see insurance companies hyperscaling with AI? Just, uh, yeah, actuary— AI actuaries calculating the risk, um, and like knowing when the policy claim is right or not. Like, where do you see AI, uh, skyrocketing the insurance, uh, industry?

Well, firstly, I love this question, and I see it in a myriad of places. Um, and divisions and portions of all the companies throughout the entire industry. However, I do not believe it is the death of the insurance agency or the insurance person or the insurance agent. Um, just like any technology, like we started at the top of the conversation, you have to have a leadership component behind how you're going to deploy it, because these, um, policies, legal contracts, insurance are a promise to pay, right? We talked about you already got a first bite at the apple by you buy it without paying cash. The second part, it's a promise to pay. And in every person's mind is great suspicion, right? And you have to replace that suspicion with trust. Generally, that doesn't happen with AI, that happens with humans. And so the future of AI and insurance is doing the mundane, doing the repetitive, maybe tracking claims. But there will still be a very vital human component that has to enter in because at the end of the day, what we sell is trust and belief that it's going to be there. That being said, look, it's— the opportunity is very welcomed across this industry. We're losing about 400,000 seasoned executives and, um, experienced insurance veterans just over the next 2 years, right? 400,000. They're just— they're, they're past 60s and they're ready to retire. We don't have that backfield. AI will help, uh, supplant some of that, right? And some of the human capital can be replicated a little bit that way, but we're still always going to need people. Um, and although it can help in claims adjudication, it can help in pricing and actuarial models— I absolutely believe in that when someone has a question, they want to pivot from a chatbot or an AI bot to a human, uh, you need to be ready.

Oh, sorry, I was muted. With Reicher, you guys are insurance brokers, correct?

That's correct. We're in, uh, 42 states in North America.

Why not start your own insurance company instead of brokering?

I love that question because I've run an insurance company and I say no way. Well, just, uh, I'm gonna— without being disparaging to all the regulatory agencies, running an insurance company is regulatory lunacy, right? So it's one of the only industries— and I've been in, you know, several in professional sports and finance and credit and other ones, but It's one of the only industries where, uh, government agencies tell you what you can and can't charge. In a lot of places you have to get approved. Like, even if you're losing money, uh, you have to continue to lose money. And so it's, it's a capitalist tool, but it's sometimes suppressed by socialist thinking. And I never want to get into the place where I'm running an insurance company again, where, uh, A, I can't be all things to all people. What I mean by that is risk gets striated and multivariate among, amongst bands by, by gender, by location, by state, by weather patterns. And so you have to be able to bifurcate or be very strategic on what, what you want. When you're the insurance company, you can't what's called redline or discriminate. You kind of have to offer to all, which is fine, But then you need to be able to get rate, the right rate for the risk. It's very, very difficult. Uh, that's why, you know, the top 5 companies control almost 70-something percent of the business. Why I like the brokerage side is that, again, we, we're fortunate to be North America's most awarded insurance firm, and our famously friendly humans represent 145 different insurance companies. And so they leverage technology and AI to, to do the mundane and repetitive and shop for rates for consumers. And specifically, if I can dive a little deeper, uh, you know, the, the one great AI that really exhibited itself to the top of the list in the last 90 days for us— I'm speaking for rideshare— is this, uh, RateGuard technology that allows us, leveraging artificial intelligence, to go into consumers' policy data right? Look at the trends, how long they've been, just all kinds of other data points. And then search all 145 companies, see if there's something better, not just by premium, because consumers are driven by premium, but when you pay less, you're buying exclusions. But it compares exclusions, policy limitations, you know, generous language, and then sorts it by which is the best and then which is the lowest premium. And then we auto— automatically reach out to our thousands of customers or tens of thousands of customers every month that are renewing and let them know a better policy exists or better rate exists. And that's transformational. That's what consumers would love about AI. They might not want to turn over everything to it, but they love, covet, appreciate the fact that something is automatically watching to make sure that they're getting the best deal, or in the consumer's mind, not getting screwed over by the insurance company rate increases.

Yeah, it's a shame, uh, sometimes the overregulation of some, uh, industries. You've explored other industries like sports teams, right? I guess like the 9-figure, uh, fantasy, like once you make it in life, like, oh, I'm gonna buy a stake of that team. And sports teams are competitive, right? And it's entertaining to watch. It's, uh, Yeah, it's great. It's great for lifestyle. Is it a good investment though? Like, how's, uh, how's that been for you?

Yeah, so I've exited, uh, two of my sports holdings, and I hold a, a pro franchise that, uh, developing will to be determined on that. Getting the right venue and the right, um, tax incentives and, and plans will determine the location for that. But, uh, my experience now, and a much smaller scale than some of the, you know, NFL and MLS and, uh, NBA teams. But my experience is the, uh, only return in professional sports is an ROE, and that's return on ego. The ROI has only happened when you exit, right? And so it's tough to, tough to create a profitable entity year over year of this. Salaries keep going up exponentially, which is, which is fine, right? It's capitalism and free market. Expenses go up. Protection goes up, security goes up, cost to staff on game day goes up, and that's fine. It's just simple economics. But as everything goes up, ticket prices and TV and other revenues sometimes don't keep pace. And so it's a, it's a kind of a leveraged debt exercise for a lot of teams. Again, it's absolutely fine, but the real ROI, ROE, is return on ego. It's great to own it. And then there's an ROI when you go to sell. I will say this for any of your listeners listening. One of the truest, most accurate depictions of professional sports I have ever watched is on Netflix, and it's called Club de Cuervos. And it's about a Mexican soccer team, a professional team. It is, it's in Spanish. I watch it in subtitles for English because I'm a monolinguistic American. Sorry. But, but that Club de Cuervos on Netflix is quite literally not only an engaging series, but a quite literal peek into kind of professional sports at the pro and semi-pro levels. Just, just for your listeners' edification there.

Interesting. Yeah, definitely gonna watch it. It's interesting that you mentioned return on ego, right? It's first time I hear it. I'm gonna definitely steal that. So, but return on ego sometimes, like, I don't know, authority, right? So it can improve your close rate. So let's say you're you're talking for to finalize a big deal and you mentioned casually that you own a sports team and you give them tickets, it can help close the deal. So there's some kind of return on that. Um, yeah, what do you, do you think, um, it is still valuable to own a sports team? I guess it depends which, and each club needs to be analyzed diligently and see if it's a good opportunity or not. Um, what do you think of like virtual uh, virtual teams, right? Like, I'm more bullish on that. Like, for example, I've seen on, um, on YouTube, right, there's channels now that is like mimicking virtual UFC fighters. Like, um, I don't know, like a UFC champion, take, uh, Francis Ngannou vs, uh, Leonidas of the 300 and Spartans, right? And you have no cost to make them fight. Of course you need to buy their their likeliness and their copyrights, but I think there's like zero cost and it's highly entertaining and it's fully online. So I don't need to buy a fucking stadium, you know? So what do you think of the future of sports? Because I've talked to, I think it was a UFC guy on my podcast some years ago, and I was like, yeah, can you picture robots fighting? He was like, no. So I was like, maybe he hasn't thought of this. And second, like, what about like, I don't know, making a lineup of England vs. France, uh, right, right there, right now, without the stadium, without the physical presence. Do you feel that this could be a very interesting niche to invest in?

I, you know, I've never thought of it. You've presented me with something that has never entered, uh, entered by my mindset before. So it sounds absolutely interesting. My, the, the, the positive person in me leans into it. The, the negative guy on my other shoulder says, well, you have to compete with EA Games and all these others that do the real-time because a lot of people want to play. But, you know, I spend the majority of my time, and I don't watch a lot of TV, I spend more time on YouTube, right? Just watching stuff and learning. And I think there's an engagement factor there that, uh, that there's an idea there would probably worth fleshing out, right? Um, especially your YouTube channel is fantastic, right? All those speeches and the way it's curated and presented, it's very engaging. If you do it right, connect with the right audience, I think it's a great idea. I just haven't explored it yet. And then with respect to the question you asked before that, yeah, there is value in owning these teams, right? There's some soft assets, hard assets, but it does open a lot of doors. It does. At this point in my life, I'm not craving that as much, but it does lend itself a certain respect, right, or admiration. Um, it's again, it's not quite candidly something I'm chasing anymore. Once you reach a certain point, like just being altruistic and real with spiritually who I am, uh, we don't need other people's validation of me anymore, right? Right. The validation is what I see in the mirror or looking back at me. But it's certainly, without limiting what you said or degrading what you said, it certainly adds value for a lot of people and their entire identity is wrapped up in And nowadays, if you've made it now, uh, is it about writing books and sharing the, the knowledge?

Is that your main purpose?

It absolutely is. It's about transferring knowledge, um, or connecting with people. Not, not talking down to them, but, but just trying to speak like we're sitting across the table. I'll tell you one of the most profound lessons I've learned in writing 12 books is this. I got really fortunate in that my first one made it to number 1, and then my second one made it to number 1. And then my ego took over, and my third and fourth and fifth book I wrote, and they just, they did abysmal. And it took me a while to come to this realization that the first two, I was sharing knowledge like you just alluded to and trying to help people understand. It was about, you know, how I've bought all these agencies and how they could buy insurance firms. And then one on how to beat the insurance companies. You know, when you figure you're going to pay over half a million dollars over your lifetime to insurance companies, you start thinking about how to use that money differently. And those sold really well because I was reaching to the consumer, right? Satisfying a desire. Uh, the next 3 satiated my appetite or ego, like I was saying, I've grown away from. But the point of all of that is this: the last several books I've written, I sometimes re— I wrote Money Secrets 9 times. And it went from 300 pages to like 83. You can read it in 20 minutes. The value there is there's no ego. There's nothing about Jeff Arnold. There's nothing about look at me or anything I've done. It is literally like we're having a conversation sitting next to each other driving or at a cafe talking about these concepts. And so there's no alofeness about it or me trying to sound important. And that takes a lot because men, if we're honest with ourselves, uh, most of all we crave respect, right? And the reason we chase money and titles is because that gets us respect. But once you have that, and once you cannot make it about you and your ego or your, your, um, your titles or your accolades, and you have real intentional conversation people are more drawn to you, right? And so that's what I've learned in the middle section of my books that I wrote. It was more about, let me write about how impressive I am, or just try to sound impressive. When you kill that as your ego and you kill that, you— it does a lot. There's a saying that, uh, that I tell my children all the time: you'll make more friends in a month by becoming interested in other people than you will in your lifetime by trying to get people interested in you, right? So you have to, you have to be engaged and listen to what other people are talking about.

How do you use AI to write your books?

Oh, as prompts only. Um, I haven't fully surrendered to the AI. I, I am keenly aware that any person who uses AI can spot AI slop. Right, in the, in the pieces. Now, I certainly have used AI for prompts. I've fed all my books into large language models, and AI has told me that I have a certain cadence. And so I try to align with that cadence, and that's really helped me in my last 3 books, especially when I'm writing about AI, right? Like Aligned with Intelligence and AI Forward Leadership. It's really helped me. But, but I want to be clear, I have not abdicated or transferred my love of language and learning to AI telling me what to write. I'm still driving the, the train, moving the bus forward, but it is helping me when I get stuck in thoughts. And then lastly, um, I have found Claude to be very, very, uh, exceptional at when I upload a manuscript and I say If I've diverted the attention of the reader from something great to the attention of me and make it about Jeff Arnold, please let me know because it wasn't intentional. And that, that helps refine it a little bit more too.

Super interesting. I'm going to read some of your books, ranges from topics like leadership, clarity, insurance stuff. Of course, really want to keep touch with you, Jeff. Where can people find out more about you?

Appreciate that. The easiest place is jeffarnold.com. Just www.jeffarnold.com. I don't know if it'll be in your show notes, but it's pretty easy, easy to get in touch with.

There you go. So that's Jeff and Charles Cormier for another Founder Wisdom podcast.