RHS 093 - James Altucher on How Insurance Agents Skip the Line to Success

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Hello everyone and welcome back to the show. Today's guest, I couldn't be more excited to share with you.
Some of you may know his work. Some of you may listen to his podcast.
Millions of people do. But if you haven't, it's James Altucher.
James is a true Renaissance man. And what I mean by that is if you've ever listened to his show, he goes all different places.
He produces the James Altucher podcast. He's written 20 plus books, two of which are two of my favorite books in relation to life and business.
The first one back, and I want to say 2013, 2014, somewhere around there, 2012, was Choose Yourself. Absolute must purchase.
Go to Amazon right now. And his latest book, Skip the Line, and he's had a bunch in there.
The Power of No was another really good one that I read. But his most recent book, Skip the Line, is why we had him on to talk specifically about.
But you can't go wrong with any of his past written work. And then his podcast is just tremendous, the people that he's exposed me to.
When I first got into taking cold showers, it's because I heard Aubrey Marcus on James' show. He's had Steven Pressfield on.
I mean, it's outrageous, the people that he's had on his show. And what I always love about his style is that, one, he does a tremendous amount of research, which isn't necessarily my style, but I envy his curiosity and the way that he breaks down topics into, I don't want to say unemotional, because I'm sure there's always emotions involved in every decision and every thought process, but he tries to really break it down into how a concept impacts our lives in a practical sense outside of the tribalism and emotional bureaucracy that we deal with every single day.
I was excited when he said yes. I'm excited that he came on the show.
I thought we had a tremendous conversation, and I also am very proud of myself for not going completely fanboy because of how much respect I have. I mean, I've listened to James's podcast since his very first episode.
And I think he's at like episode 900 or something now, which is crazy. So you're going to love this.
We go all different places. And specifically, we dive into how insurance professionals can skip the line, can get ahead, can make that leap from where they are to someplace further in career development than would normally be expected.
And I think you're going to get a tremendous value out of that. Before we get there, I want to give a shout out to today's sponsor, and that is Agency VA.
I've talked about it multiple times. Agency VA is the horsepower behind my agency.
I have a tremendous tactical service VA and I now have an appointment center who's actually calling out to target markets, delivering our value proposition and trying to set up appointments for me and it's already starting to bear fruit. We're less than a month in and it's an incredible decision.
And these are just the first two VAs that I've brought on. And then they supplement the work that Sarah's doing and that I'm doing and we can continue to build our team out.
And if it wasn't for Wes and Ben and Lally and the entire team at Agency VA, everything, everyone that I've come in contact with there has been nothing but absolutely tremendous. and my agency wouldn't be where it is today without Agency VA.
Also, interestingly enough, I think their office or headquarters is right across the street from Podium, which is another tremendous technology that I've started to look into for some of my inbound stuff. So Podium is a new sponsor of the show as well.
They're not today's sponsor technically, but it's just interesting that Agency VA and Podium, they can see each other from their buildings and both are big time pieces of what Rogue will be. You'll hear more about Podium as I start to dig into how it impacts and helps my agency.
But go to agencyva.com. That's agencyva.com.
Go to agencyva.com today. If you need help, talk to Wes.
Talk to Ben. Talk to the team there.
Think about a virtual assistant. Not just any virtual assistant, but one who's the hiring process, the technology that they use, the tools that they've been trained on are targeted for the insurance industry.
You can't go wrong. All right, let's get on to what was easily one of my favorite conversations I've had in a very long time with one of my absolute favorite thought leaders in the entire world today, James Alster.
Hey, Ryan. How's it going? Hey, James.
How are you? Good, good. Good.
You daisy-chain in interviews today or what? No, no, just kind of hanging out. That's nice.
My book came out a couple of weeks ago, so maybe that day. I probably should have done more promoting the book, but I do so much each time.
And I just figured, you know what? Let's see if just word of mouth will do it. Yeah.
I don't think word of mouth does it. I mean, all my reviews are great and all the feedback is great.
But I have found that a lot of people don't even know I have a new book out. And so whatever.
It was an experiment and it is what it is. Yeah, I get that.
And it seems like that's, it seems like you've launched every book, at least the book since I've been in your ecosystem, which is seven or eight years has been different. Yeah, I always try different things.
And, but I got a little tired of marketing, because, you know, marketing, marketing is important and it's good. Like it would be great if, you know, let's just pick up a mythical thing.
Like if Kim Kardashian announced on her Instagram and Twitter that the only book she would ever recommend to anyone is Skip the Line by James Alvacher. That would clearly be a great thing.
But to get to that point would involve me saying, doing, and acting in certain ways that don't feel authentic to me. And that includes even asking people if I can go on their podcast.
You're supposed to just be not afraid to ask. And I'm not really afraid to ask, but I'm also not that comfortable with it.
I feel like the book did its best when people authentically said, hey, this is great. Can we talk more about it on my podcast? Or, hey, this is great.
I'd like to recommend this on my TV show or just the word spread on Twitter and stuff. And, you know, I don't like the idea of branding and marketing that much.
I also think that you have to be very careful with the favors that you pull. You work so hard to generate friendships and the social capital that comes with friendships.
And if you're constantly pulling that favor lever when you really need it, it's not there. Yeah, I agree.
And on the one hand,

you should be comfortable about asking people to help you. In fact, people often enjoy being asked to help, but you know,

I'm on the receiving end of a lot of that.

Like I do a podcast and every day I probably get about 30 requests. Hey,

can you put so-and-so who wrote a book called make your dreams happen?

And this person may always wanted to be a goat herder in Montana and he or she made her dreams happen. And all of these books are great and they work really hard at it.
And I admire anybody who writes a book, but I feel bad because I can't even literally respond to all the emails. And so then do they hate me afterwards? And not that I even care that much.
I don't know them. But I don't know.
It's just a weird thing where, I mean, you use the word ecosystem. That's part of the ecosystem of a podcast and of anybody who has a platform is, hey, can you read it? I have just like a whole thing of like free books that people send me unsolicited.
And I don't mind it. I read the books or at least look at them and if something is great I do ask them but I don't know you're right I don't like like for instance I'm friends with Tim Ferriss and uh and I would love to go on his podcast to talk about my book but I will not ask him to go on his podcast because you're right there is social capital that's spent and I don't really communicate it with him that much so if you communicate with him the only time only times when you need something I think that's poor form I'd rather just more be there and comment on like the way I communicate with him is if he writes something I like I write him and comment on it and we have a dialogue.
But I don't need to say, hey, can you please let me on your podcast? I have a new book out. You might not have read it.
You might not have heard about it. I don't know.
I'm proud of the book already because I just see from the reviews and from the emails I get that it's already helped a lot of people and that was my goal. And that's it.
I'm fine with where it is. So I know I'm rambling about marketing.
I will say one thing about branding. The other day I was in some kind of Q&A and someone said, I felt you really hurt your brand when you shut down your crypto.
I had a crypto newsletter for a while. So I recommended people buy crypto.
I recommended in 2013 on CNBC that people buy Bitcoin. And I recommended it again in the fall of 2017.
And I started a newsletter about it, but then I stopped it because everybody wanted to day trade these shit alt currencies. And I was just interested in recommending Bitcoin and maybe Ethereum, which proved to be correct.
I even said 95% of these alt currencies are going to go out of business and Bitcoin's going to survive. And I took a lot of heat.
People were laughing at me. People were insulting me, which is fine.
I just wanted to say, I always say the things that I think will help most people. And I always want to be authentic to myself in terms of shutting things down that I feel are no longer necessary,

even if it costs me money or whatever.

But I said to this person,

what does it mean to ruin your brand?

Like a brand, think about Coca-Cola.

A brand is basically the difference between reality and the lie.

So Coca-Cola, oh, if I drink Coca-Cola,

I'm going to be skateboarding in Santa Monica

with all my cool, beautiful friends

Thank you. and the lie.
So Coca-Cola, oh, if I drink Coca-Cola, I'm going to be skateboarding in Santa Monica with all my cool, beautiful friends, and Coke is just going to be spraying everywhere, like one giant Coke orgasm. But the reality is, as Steve Jobs once put it, Coke is just sugared water.
And so a brand is this thing with like beautiful people and this could be you and it's a lie. And then the authentic thing is more real.
And then I could, if I know what's authentic, I can choose. Yeah.
Do I want sugared water or not? There's nothing. If I'm willing to do that, then I'll do it.
And so in terms of the personal branding became this big thing over the past 10 years, like what's your personal brand? Well, I want that perception to be as close to reality as possible. And then if you succeed, you've succeeded because you're who you are and your authentic message helps the world and has a better chance of not only helping people but surviving, you know, for the long term.
And if it's just based on brand, brand is the difference between the perception and the reality is just all air. And so that air is a waste of air and I don't want to do that.
So I don't care about brand personal branding. I completely agree.
I just came on your show and I took over. I'm sorry about that.
No, it's fine. It's, it's no, it's good.
I, I, I wholly agree with you. So I, in the insurance space, I have one of the longest running podcasts.
And I have people who will, to a much smaller extent, I kind of understand exactly everything you just said, but take it to independent insurance agents in the United States. So take that ecosystem.
And I feel you. And people will say things like, oh, how do I become an insurance influencer like you? And I'll say to them, stop thinking about becoming an insurance influencer.
That's step number one. Just take that whole concept out and just be, if you're interested in a topic in our space, just talk about it.
But there's, but there's no gain. There's no, like, if I get on this podcast and I, you know, write for this insurance carrier and I make this many tweets that all of a sudden people are going to care.
Like you either have interesting things to say that help people or you don't. And I only started this podcast because I wanted free consulting.
I'm not, you know, I went to college to drink beer, chase women. And, and, and that was basically it.
I mean, that's, I played baseball too. A job at those things.
Cause that's important. Yeah.
So, so I'll tell you what didn't get me a job, my math degree that did not get me any money. So that's a hard degree to get though.
So you, so I'm impressed with that. Like I agree with you about college and, and I've written quite a lot about this.
Yeah. But like a math degree is a hard degree to get though.
So I'm impressed with that. Like I agree with you about college and I've written quite a lot about this.
But like a math degree is a hard degree and you learn how to think about certain situations very quickly. Like I think that improves your brain in a math degree.
That's a skill. So what was funny about that was – so I went to the University of Rochester and, if you were, when I would walk into one of my math classes, it was like, one of these things is not like the other, like, what is he doing here? Like they're all up on the chalkboard.
All my classmates are up on the chalkboard and they're a plus B equals seven. And let's prove this.
And they're using letters. And today I have no, I couldn't even recreate it today, but I'd be sitting in the back, like in the, in, in my, the rat in my brain

would be working as hard as he could to keep, just to keep up with these dudes. And they'd be like,

this is light work for them. You know what I mean? This is like their warmup equation.

That happens to me too. Cause I was majoring in computer science, but a lot of computer science

intersects a lot of theoretical computer science intersects with math. And, uh, uh, there would be

I think that's a good idea. too because i was majoring in computer science but a lot of computer science intersects a lot of theoretical computer science intersects with math yeah and uh uh there would be like some guys just like in the back of the class not paying attention and then they would get beyond an a plus like it was so easy for them yes like i was just struggling um but then but then there's good things about the struggle also because if you're interested in the topic you find yourself finding new ways to learn it's so hard for you.
Like the people who are easy don't necessarily learn about learning because it's so easy for them. Yeah.
So what it did, and this is the strange part, is it forced me into learning writing and talking better because I was so – I wanted to go to school to be a mechanical engineering. I hit thermodynamics and basically

had to make the decision, chase beer or drink beer, chase women, play baseball, or become a

mechanical engineer. I didn't become a mechanical engineer.
So I went to my guidance counselor and

I said, okay, it's second semester, sophomore year. I have like a one seven in engineering.

How the heck do I graduate? And she said, she said, math is the only thing that you can get.

Thank you. semester, sophomore year, I have like a one seven in engineering, how the heck do I graduate? And she said, she said, math is the only thing that you can get and get out of here in the normal amount of time.
So that's what turned me to math major. And that sucks so bad.
And I hated every second of it. That I had I started focusing on writing.
And that's when I got into writing and speaking and, you know, communication, not necessarily speaking, speaking, but communication. And obviously, that's today has become a big part of my life.
But it was just funny how in high school, it was science and math. And I find those things infinitely interesting.
But in school, they actually pushed me back into the liberal arts because I just was like, wow, this is really tough. And I don't really want to dedicate the brain cycles to this.
Yeah. Well, let me ask you a question.
In terms of becoming an insurance, let's just brainstorm for a second, even though I know you've thought about this for a million hours. In terms of being an insurance influencer, my gut would tell me that there's creative way, person individually has their own should have their own insurance profile so for instance for me i don't need insurance for basic medical but if i i don't have insurance at all actually in fact right now which i should get i'm 53 years old i should probably get it but like i should probably get catastrophic influence uh you know cat like just in case something catastrophic happens to me I should probably get it.
But like, I should probably get catastrophic influence, you know, cat, like just in case something catastrophic happens to me, I should probably get the catastrophic insurance. And, and then and then I should probably get like, I don't know,

liability insurance, stuff like that, just in case someone trips on my sidewalk or something.

And just like stuff like that. But each person is different.
I think being really honest about

even though, let's say I'm an insurance agent, even though my objective is to sell you as much insurance as possible, I should really kind of define my own methodology for figuring out what is your ideal insurance profile so you don't have to get everything because it's all one big. Insurance is basically another form of a casino and the odds are stacked against the regular person but you get insurance to have peace of mind which i get and uh and then there's probably other kinds of creative insurance that people don't even know about uh you know like if you're a dentist what's insurance that people don't pay for the retainers that you get i don't know there's probably weird or like war Buffett shows, uh, sells like nuclear attack insurance for super bowls.
So it's probably like creative insurance things also on business models around insurance. And so that's how I would approach being an insurance influencer off completely or no, no, you're not.
So, so the interesting thing about the, so every, you know, it's funny if you were to, if I were to look back at like 16 year old Ryan becoming an insurance agent and insurance and being in the insurance world, it not every little boy's dream, not even close. Like the, but it's a fun industry because it's all like statistics and odds.
It is a giant casino. It's like gambling.
It is. And it can range from everything from the, what I find interesting are, are the, the problems that you have to solve.
Not necessarily the insurance problems. Cause those are kind of like a little more straightforward.
I mean, there's some creative stuff that you have to do depending on how crazy the risk is. But what I find interesting is, is the business model challenges in so much as, okay, if you're going to sell auto insurance, right? Well, you have a very unique set of problems that you have to solve in order to put enough auto insurance into your business to actually make money.
Because now you're competing against Warren Buffett. You're competing against all these different forms.
The other side of the coin is you can go complete custom paper. You can have direct contracts with the Lloyds of London.
I know guys that have flown and gone onto the Lloyds floor and literally handwritten out, well, I mean, on a computer, but written out word for word, entire scripted

policies that serve flood insurance to mountainous regions in Northern California, right? Like,

that's how specific they get. So there's this wide range, and then you can choose your own path

inside of, you know, that range, you know, as commoditized as it gets to as unique as it gets and um and it it you know and then you have distribution model issues which is right that actually it's the district like that's another fascinating way to do it is to kind of so basically insurance again there's a there's another reason to get insurance, which is that there's peace of mind if something accidental happens, the one in a million chance you fall off the Eiffel Tower, you need catastrophic insurance or whatever. But there's a fascinating part of insurance where you could beat the odds.
So if you understand where the odds are being mispriced, which is very difficult because, I mean there are like PhDs all over the place, figuring out the odds on every tiny event in your life. But if for some reason you think you are not, um, you're, you're not accurately being represented by the odds, then you should buy insurance.
So for instance, let's say you don't take good care of yourself, but you're 30 years old and there's ways to analyze what your biological age is as opposed to your chronological age. And if your biological age is 50 instead of 30, which unfortunately for you, that's not very good, but you could basically buy insurance that's priced for 30 year olds, knowing that you have the biological makeup of a 50 year old and might need it more than the average person.
Now you've won the, you've won at the casino. And so, you know, being at least the people who get the money when you pass one hit the lottery there.
Yeah, exactly. So, so, uh, there's kind of interesting issues with insurance where like, it's like stocks, like, when are you, when are you a good thing for, uh, when, you bad for insurance companies to take a risk on? Cause you're defying the odds in one way or the other.
And knowing about that is interesting. But again, I don't know.
You'd have to figure, you have to convince people that this is an interesting thing. Like you're appreciative of this because of, of your math background, but people, most people don't even really understand what insurance actually is and how, and how.
No, you know that's a, and that's the, and obviously I didn't want to talk to you just about insurance, but it is interesting. Uh, it's about being an influencer too, in an authentic way, as opposed to saying like, what would happen to your family if you got hit by a car tomorrow morning, you never know.
And the reality is you do know the odds, but when they sell it and they're trying to be an influencer, like I can help you find an insurance broker. I can help you find the cheapest way to do this.
That's a little bit inauthentic to me.

Yeah. And it plays out in your numbers.
So you can sell on fear. So the number one way from a conversion and cost of acquisition standpoint of selling insurance is fear,

right? Hey, you're this many years old. You know, statistics tell me that a male this age, you know, with these defining characteristics dies this many years from now.
So buy your life insurance today or whatever, right? Or buy your car insurance. You know, you're in Florida.
Hey, three out of every 10 drivers in Florida has no insurance. So if they hit you with their car, they can't give you a dollar.
Right. So you need to have this.
Okay. So you can sell on fear.
The problem is the harder you sell on fear, statistically, the lower your retention rates are because the way in which you're driving them in actually trains your clients to live on fear. and they look for the next best or the next person who's selling harder or selling fear in a different way.
Right. Oh, that's such a good point that basically when you're inauthentic, the only asset you have going into this idea of how can I be an influencer is your ability to sell essentially your ability to bullshit.
And if someone can bullshit better than you, then you're like, oh, then the customer's like, oh, this is a better influencer than that guy, even though you might not be thinking the word influencer. But if you could say, listen, no bullshit, you really don't need, you know, you don't really need all insurance packages.
You don't even need basic, with your income and your health makeup, you don't even really need basic health insurance. But look, if you go to sleep at night worried, how am I going to take my family if suddenly I get cancer, then here's the type of insurance that might be interesting to you.
If your business sometimes doesn't make payroll, it's not insurance, but maybe this kind of, I'll be honest, it's sort of an insurance,

like getting kind of a credit line from a bank is a way of having insurance to meet your payroll,

just in case your customers are late on paying. And you could kind of put this,

what's the thing is, I'm not going to bullshit you. I'm going to make less money off of you

than all the other guys, but that's fine. At least you're going to get the right insurance

and we build a relationship. And I'm just being upfront and honest about what I'm doing.

So this is why I, I, I, your brain, when you were talking about brand before is the difference between what you say and, and, and who you are and everything in the middle is the bullshit. I act, you know, what I personally believe on the idea of brand and what I'm trying to do, cause I own an independent insurance agency, or I actually started at March 9th of last year.
So I'm like a year and two days in. I wish for many reasons, someone would have told me seven days after I hit the launch button, the zombie apocalypse was going to happen.
But you know, I'm sure everyone does. So just out of curiosity, and sorry to interrupt, did you get into kind of any COVID specific packages? No, I tried to not go out of business every day by just fighting and scratching because for the first two months, so I primarily focus on commercial insurance, property casualty.
So like professional liability, workers' compensation, general liability, those kinds of things, property. So, you know, if you run a contracting business or you're a manufacturer, or I have a lot of just having been in the marketing space for a while, I have a lot of people who run marketing agencies and stuff around the country that I do their insurance for.
But for the first three months, for two and a half months after I launched, I couldn't, no one would take a phone call. I mean, it's the middle of COVID.
Who wants to take a phone call from a startup insurance agency and talk about switching their insurance? Nobody. So it was like, it was interesting.
That was an interesting time. But what it forced me to do was really hammer in the idea that what I deliver has to be this far away from, and no one can see me.
So I, except for James, my phone gears are very close to each other. You know, it has to be, it has to be this close, from, and no one can see me, except for James.
My fingers are very close to each other. It has to be this close.
I actually have to deliver on what I'm saying I'm going to do. And that value proposition has to be substantially different because what everyone else was doing was price, price, price, price, price, fear, fear, fear, fear, fear.
And that's a low retention, high churn business that I have no desire to play. And it also isn't long-term profitable.
I'm taking notes. Yeah.
So it's, so that was a really interesting time. That was a really interesting time.
So how did you differentiate yourself? So I, I, first of all, my agency's name is not my last name, which is about 90% of insurance agencies in the country are like, would be Hanley Insurance Services. So my agency is called Rogue Risk.
So one single syllable alliteration, R is a power letter. I also just like the word rogue.
And I wanted to, I wanted to define myself immediately with the word rogue as something that was tangential to the concepts that you would think about with insurance, right? Like you think insurance, you don't immediately think rogue. So it does pop people's attention to go, there's something different about that.
And then I don't want to bore you with the details, but essentially most agents just come in two months before renewal and they say, Hey, let me quote your price. Hey, James, you got to have professional liability.
You're a podcaster. Let me quote your price.
Right. And you go, God, all right, whatever.
Sure. And maybe you change, maybe you don't.
It depends on how much they're saying being you and what, what, how I am trying to flip that is by saying, um, you know, I actually have a service plan and it sounds terrible. I'm not describing it the proper way.
Um, I think it doesn't matter, but you know, what I do is I walk you through a whole set of prop, uh, processes that actually lets you take control of your price. So it's not, it's not in your agent's best interest for your price to go down.
It's only in their best interest for your price to be at its lowest the moment you buy. And then they're actually incentivized through commissions for your price to steadily increase over time with them as the agent.
And what I'm trying to do, this is why growth is slower, but hopefully retention is higher, is what I'm trying to say to you is the highest I want your price to ever be is the day that I sell you. And then we're going to work to push it down over time.
And, you know, I'm working, you know, this is your 10,000 experiments thing, which I eventually want to talk about. But, you know, I've probably crosscut that in social and in video about a thousand times.
I have in less than a year, I've, I've created probably one of the more traffic YouTube channels for an insurance agent in the entire country. I have like 160 videos that I've done and, you know, inside a year.
So yeah, you've really, you've really kind of been doing a good job of kind of combining insurance, traditional insurance, broker thinking with, you know, sort of social media influence style marketing. I call it a human optimized agency, which is an awful term.
I got to figure out like a cooler word for it. But basically what I'm trying to do is take all the core values of a traditional agency,

caring, compassion, trustworthiness, which they do actually have like working with an independent agent. The vast majority of them are awesome.
They just have no ability to come to you in your space. You have to come to them.
So what I said was, I'm going to take this world and I'm going to then take the digital world. And I'm going to try to take the best pieces of both and mash them together because there's no soul here to the business you're just transaction 7587 right and over here you're james out to share but man we're going to make it as hard as possible for you to do business with us and i'm trying to mash those two things together in the middle and you know sometimes it works sometimes it works, sometimes it doesn't.
But let me ask you this, like, have you thought about going meta with this concept? So, and this is what I call, I call this in the, I think in the skip the line, I call this idea exponential. So there's like idea, I have a chapter about idea calculus, where I talk about idea sex, which I've mentioned in other books, but I talk about idea subtraction, idea division, idea multiplication, and idea exponential.
So an idea exponential is when you meta your idea. So this idea of taking an industry that is 99% filled with old school techniques for selling and going meta with a technique that's worked for you to then sell that meta service to other industries.
So for instance, go to personal injury lawyers. A lot of them, you know, chase ambulances.
That's the traditional model. But what if you say, listen, how about we hit a larger audience more authentically and,

and in a more kind of, um, uh, uh,

without you driving around all night chasing ambulances,

like you could kind of make money or get customers while you sleep sort of

thing.

I'm going to take what I did in the insurance business and help you do it for

your business so that you can use social media appropriately and quadruple your revenues. Like it seems like you could provide that service because you've done it so well for yourself.
What's up guys. Sorry to take you away from the episode, but as you know, we do not run ads on this show in an exchange for that.
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Peace. Let's get back to the episode.
So it's funny that you say, so one, that is in my game plan. Some of it is I have to hit escape velocity and revenue for this business before I start growing other people's businesses.
And that sounds like an excuse. No, no, no, that's very reasonable.
Yeah. But, um, but I have started to do this with, um, so one of the things that, and this feels more like a consulting conversation than a, than a podcast interview though, hopefully it's engaging for you.
Um, absolutely. One of the coverages that I believe very strongly in, um, is cyber insurance right now, the fastest growing risk that every human has, both families like me sitting in.
So I work out of this is my home office. My family has this risk and my business has this risk at the same exact time.
And it's cyber. It's cyber attacks, particularly the two big ones are ransomware attacks and social engineering.
So social engineering is you get an email from me that looks like me, you click on it. And now all of a sudden, you know, you're wire transferring to some account somewhere, you know, whatever.
And, uh, those are the, I know this exists for identity theft, but this doesn't exist in general. So, so cyber insurance does exist, but the, so identity theft is basically, um, a small amount of recouped coverage for, for, for personal issues, but it doesn't necessarily cover.
What if someone uses your home router to then steal and do wire transfer fraud to all your neighbors, right? What, what identity theft does is we're going to try to get you off the underground or underground, the dark web kind of things. Like if you're, if we find you there and we're going to monitor it, but what cyber insurance is going to do is it's going to help you recoup the loss when the social security number of your neighbor down the street is used to buy some house in some other state to take out a loan,

that's going to come back to you. And that's what cyber insurance for.
So individuals have this

risk. The larger risk is businesses.
So I just got a call from a guy because, again, because of

YouTube videos and stuff, I get a lot of random phone calls. And he said, I just had to shut my

business down. We had a $600,000 cyber loss, which was ransomware.
Basically they put malware on, shut his hard drive down and he had to pay 600 grand to get it. He'd pay 500 grand to get it back another hundred to get the hardware fixed.
But the bigger issue was, and he didn't have this on his policy was his two biggest clients because of the reputational risk of now having this issue. Um, his two biggest clients canceled because they're like, we can't, as a board, we can't put our businesses in jeopardy by working with someone who just had a major cyber attack.
So they canceled their contract with them. 90 employees unemployed that day.
Boom. That's horrible.
Like, why didn't he just use, you know, Dropbox or AWS to like, I, like if someone stole my hard drive from me, I could care less because I store everything in the cloud. Yes.
So he didn't do that. So this was the, this is the issue is there's two, there's two levels.
And this is kind of getting to, this was a very tangential way of saying, I'm working this, like, I'm going to do videos for thing. So I'm working with a couple of different cybersecurity firms and a couple attorneys that focus on cyber to help them put content together because cyber is a big part of it.
But I'm really like the last defense. What you need is the actual processes.
Technology is part of it, but it's more what you said, having a standard backups, having dual servers so that, that, that aren't connected. So anything that goes in one is just mapped or mirrored to another.
It could be a Dropbox file. You know, that's a very simple way to do it.
So that if someone throws a ransomware attack on one server, you're like, no problem. We're going to cut the hard line, right.
And just file this other one up. And here, no one knows the difference.
You can have this thing that's worthless. I'm never going to pay you.
And that can be jammed up forever because I have my full data backup over on this server. And off we go, you mirror that one.
And so, so these type of like procedures are how you defend 99% of these. And then the last layer of defense is if for some reason, one of these failstates doesn't work, then you have the cyber insurance to back you up.
Yeah. So that's a whole service, which is like, you know, ransomware proof your business.
Yes. And insurance is a component of that.
So I guess that could be almost like the next level of meta. And then the final level of meta or the next level of meta after that would be other industries.
Yep. Like, like personal injury lawyers or dentists or whatever.
Yeah. So it's interesting.
It's interesting stuff. Um, but let's, let's, uh, let's, I want to ask you some questions.
Um, and I didn't get a chance to do this cause we got right into the conversation, but, um, I just want to, uh, I want to do a super quick, super, super quick ego stroke for you. And cause I just have to say this.
Um, I have been following your podcast since the very first episode. I can't tell you where I found, I have absolutely no idea how I ran into your stuff, what you were doing.
Um, I used to, I used to read stock picker, although to be honest with you, I had freaking clue it was until i heard you talk about on the podcast years later but like um since day one the very personal branding yeah at least then right at least that at least back then but um uh very very first episode and i just think uh you are one of the best interviewers in the entire like in the in the world right world right now, that episode you did with Larry King. You know, it was funny.
As someone who listens to you and, and listen to Larry King. And what, what was your guest name? I'm sorry.
I just forget his name. Cal Fussman.
Who's awesome. Awesome.
Yeah. I said to myself, you know, you, you were putting Larry up in a pedestal and certainly the longevity of what he did.
I, he deserved all every bit of that, but I think, I think you are as good as, as he was with a difference with a slightly different style. And, um, it just, I just wanted to get that off my chest because I have been such a fan for so long, man.
I truly appreciate that because I really study interviewing like, and you look at the great interviewers out there, like Howard Stern, whether you like what he says or not, or you think he's too dirty or you think he's this or that. He is a great interviewer.
And he has recently a book came out. If I remember correctly, it's called Here He Comes Again.
And it's like the text transcripts of many of his interviews. And then you could really see what he's doing and how good he is.
Larry King, I didn't know what I thought about him because he had this style, which I didn't quite appreciate, which is not doing any research at all before doing the interviewing. But Cal explained to me why he did that.
And it gave me a new appreciation of Larry. I have to re-listen now to some of his interviews and see.
But there's many different styles and many different techniques. But one thing in common with a good interviewer has is relatability.
No one is going to give a shit about giving you good answers if they don't like you. And both Howard and Larry have that.
And I think the interviews I've done, particularly early on where I failed, was when the person I was interviewing didn't like me because I didn't spend the time establishing relatability and likability and so on. And it's a difficult thing to interview well.
I've been on a thousand, and I could see the difference between the good and the bad. Who would be an interview that you think you didn't do well? What would be an example of that? So this was early on, and there was a rapper, Biz Marquis, in the 80s.
He had a classic song called She's Just a Friend. And it's a famous song.
Like, if you were to hear it, you would would say, oh yeah, I like that song. If any of you are listening to this show and you haven't heard that song, there's something wrong with you.
We started off with Wu-Tang two days ago. So come on.
Yeah. And the good thing is also it's a really funny video.
Like Bismarck, he had a unique style, which is it was a little bit dissonant, his singing. But, you know, there wasn't really singing in rap then.
So he was kind of like, you know, he was playing with the form. And that's that's why, you know, rap is is an art form and not just, you know, obviously it's not a fad at this point.
But in the beginning, people thought it was. And so he's funny in it.
He sings like off key. But it's a good story.
It's a good concept. It's a relatable concept and it's a good beat.
And I asked him, how do you feel about the fact that most people know you from that one song? And he got very upset. He's like, I've done many other songs and I'm also so-and-so on this Nickelodeon show that a lot of kids watch that millions of kids watch and I'm like I know that but if I if I go to China right now and I hum she's just a friend all billion people in China will know what song I'm referring to and he's like no no man I've done like more than you know one song and I said I know that but when i even go to your website as

soon as i reload your website it starts playing that song like clearly you must think it's what

your most valuable thing in your repertoire of songs your oeuvre of work and i think the mistake

i made there because everything i was saying was valid and everything he was saying was valid

and the mistake i made was a kind of not bonding with him a little beforehand. Not, and again, you have to be authentic about it.
I really do admire the guy. Um, and, and B when he pushed back, there was no reason for me to argue with him.
Like I could, you know, like, so how the Howard Stern technique would be like, okay, yeah, I, you've done many great things, but then later on circle back a different way and it come at it from a different angle to get the same point across when you, when you reestablish the bonding and you've also given him status as a, as an artist, which is clearly what he was looking for. And, uh, but you know, another thing I learned from that one was rather than just air the, and I did air it.
I air the good and the bad and the ugly, but I meta aired it, meaning I was with kind of the sound guy and one of the producers of the show. And I would rewind back and forth the interview and analyze where I went wrong.
So the podcast became about how badly I interviewed him and how I could have done better. So I made good use of a bad interview.
But that was an example of a bad one. I have many bad ones.
I've done like 800 or 900 podcasts now. I have many, many bad ones, but hopefully more good than bad.
Yeah. Yeah.
Again, just haven't listened for as long as I have. It's been, um, it's been intriguing to me.
Um, it's been intriguing to me to watch you evolve or to hear you evolve, I guess. Uh, because, you know, at the beginning, obviously you were very raw, but, but the thing that has for me is, has pulled me all the way through.
And I was, what I was always intrigued by and has been aspirational for me. And I've done, I've been podcasting since 2011 and, and, and is Ben,'ve pulled your curiosity always that, that isn't, you've never lost that.
The, the curiosity, if I had to pin one thing when people say, Hey, why, why are you interested in Alistair? Sometimes he talks about fucking space and other times he's talking about crypto and he's interviewing some celebrity, you know, why, why, why do you get so into that show? And I was like, I, I, sometimes I can give two flying Fs what, what the guest does. I'm just not interested in the guest, but I am very interested in how after all these episodes, however many it is, you know, eight, 900, whatever, that you've been able, you've never lost that thread of curiosity for all these random, you know, seemingly random concepts and ideas and how you tie them together.
Do you think that's part of just your personality? That's who you are? Is it something you've had to work at? Like, are there days when you show up to punch into the podcast and you're just like, shit, I, man, I really don't want to ask any questions today or, you know, yeah. I mean, yeah.
So, so sorry to interrupt. No, no, you're fine.
But, but like, but yeah, I mean, there's a lot of times and, and, absolutely. Yeah.
I mean, yeah. So sorry to interrupt.
No, no, you're fine. But yeah, I mean, there's a lot of times, and this is the thing about, like I've interviewed in the past a lot of self-help people, and they have a lot of, like anybody, they have problems.
Everybody's got problems. No matter how much of an expert you are at anything, even keeping yourself motivated.
Let's say you're an expert on motivation. Sometimes you're just not motivated.
Sometimes you're burnt out. And life's a hard thing.
And part of the challenge of life is every day showing up. And even that's hard.
Some days you can't. But I always have a guest on that I personally need to know.
Like, let's say, you know, I have on a physicist. Well, like many people, I think it's an intriguing question.
How did the universe start? What happened before the Big Bang? You know, what's the benefit of asking these questions? Like, why should we care? Because we're never going to to know the answers and and but I'm curious since as a kid these things so that's why I might talk about a space person or let's say I have on someone like uh you know Sarah Blakely who started the company Spanx and you know it's a multi-billion dollar company now she's one of the richest women in the. And she was a door-to-door fax machine salesman who didn't know the first thing about clothing.
And then she creates one of the largest clothing lines in the world. How do you, I want to pivot my life sometimes.
I want to change careers sometimes and do something more exciting to me. How did you do it? And how did you face all the people who told you, because I was just guessing, how did you face all the people who told you, hey, Sarah, you can't do this.
You needed to go to school for it or blah, blah, blah. So I was curious.
Or let's say I'm starting doing stand-up comedy and I got heckled the night before. Let's just hypothetically say, like when I first started, I would have it on a comedian and I would say, well, what'd you do when you got heckled? Like, so I would be asking questions that would better my life.
But the reality is if something betters my life, then there's going to be answers there that better everyone's life. And I find a lot of people have on guests because they're famous or because it will drive traffic or whatever, but that's not a good long-term way to do a podcast.
You have to, it has to come from your deep personal curiosity and love for the topic and so on. Because then there's other people.
There's an audience for everything if you're authentic. If it's about rap, there's a huge audience for rap.
If it's about comedy, huge audience. Business, investing, leadership, congressmen, presidents, there's a huge audience no matter what.
But you have to know, the reason you know it is because you're interested. So like, for instance, we're doing a podcast right now and we're using Zoom.
And Zoom is great. There's 700 million users.
No one says Zoom shouldn't exist. But Zoom for podcasters is not ideal.
The video is a little bit low quality, so YouTube will not favor videos done in Zoom. The audio is low quality because it has that internet connection, Skype-y sort of feel to it.
But there's not really a good solution out there, to be honest. And I've researched this a lot.
So for the past almost year now,

I've been creating my own software that has all the qualities I want. And so you could say, well, how did I validate the idea? I didn't validate the idea.
I only know because I've done and been on thousands of podcasts. I only know what I would use.
So I'm creating the software I would use. That's good enough for me because I am authentically asking, who am I? What do I know about this? And what do I want? And why now is it important? And why is it the case that it hasn't been created before? How am I going to create this that is unique? And I could say, this is the reason why nobody else has done this.
And if I can answer those questions, I validated the idea. And I know other people will use it.
Because if I'm a good podcaster and having difficulties, then many of the 2 million other podcasters are having the same difficulties. So again, it all comes from my own personal needs and that's how you satisfy other people's needs.
I think you hit it right on the head with a general, like if you're, this comes back to everything we were saying at the beginning about brand and all these things. Like if you have someone on your show simply because you think it's gonna have traffic that you've just put yourself in a position to have a terrible episode.
I actually hit the jackpot with this the other day. I took a chance on Todd Stottlemyre, a former, um, Oh yeah.
I used to, uh, back in 2009, I'm talking this. So it's 12 years ago.
I did a couple of investors with him. He lives in, um, uh, I want to say Phoenix, Arizona.
Yes. So he came out with a book and, um, and, and he, his person reached out and said, Hey, hey I'd love to come on I knew him as a major league pitcher I watched him win the world series but who the heck knows right and I just said screw it ended up being freaking awesome we had one of the best conversations I've had I was like oh my gosh dude I was like this is now we tweet at each other every once in a while I was like this wonderful guy yeah he's oh super smart.
Oh, super smart. Yeah.
Oh, I loved his whole vibe. I was into everything he had to say.
It was awesome. That reminds me of like, I had Joe Moglian who was the CEO of Ameritrade and he created it into a multi-billion dollar bank.
Like he really was a phenomenal wall street CEO. And then he quit.
He hated being, I don't want to say he hated, he didn't want to be CEO of a bank anymore. And he became an assistant coach for the University of Nebraska football team.
And he totally changed his career to being like a football guy and a football coach. And then he became a successful coach for the South Carolina Panthers.
And now he's retired. But I wasn't interested in banking or a CEO term, and I'm not interested in football at all, but I was really interested in how he changed like that and what plaque he got.
I mean, he got divorced, he got a lot of, and he had to take two steps back to move one step forward. But stuff like that, you're right, you hit the jackpot sometimes sometimes and it's fun.
And other times like I had on Chelsea Handler because I thought it would be a lot of traffic. And man, not only was that the worst episode ever, but it didn't even get traffic.
Like if people could tell instantly this is not James style. Yeah, that was a tough one.
I could just tell that you were you were., you were, I, again, I feel weird. It feels weird.
Cause I listened to you so much. I could tell, but even in that episode, as a listener, I could tell you were work, you were working like it wasn't like, um, so, so, so Brian Keating, uh, I asked him after all the episode, you did like those four or five episodes of him right in a row.
And I reached out to him and I was like, dude, I run an insurance podcast, but this shit is so interesting. Is there any way that you'll come on? So he said, yeah.
So I have him, we're going to have a conversation in a couple of weeks. That's great.
But like that is like butter. I can, you can tell you fuss men, other people come on.
It's like, you know, it's like, we just got, uh, uh, you know, however many million people listen, just got stadium seats to the two of you having a cup of coffee. And it's and it's awesome.
Yeah, no, that's a good way to put it. Like, I really like I listened to, you know, another great interviewer, which it's almost surprising to call him an interviewer.
But another great interviewer is Joe Rogan, because every one of his guests feels like he's having like his best friend on and they're just having a conversation but ultimately you see he gets what he wants out of the conversation and some other things he didn't want which is always good too yeah he's a great interviewer he's one of the greats and you know i try to i don't want to say emulate him because there's a lot of that means something different like there's's a lot of Joe Rogan ripoffs in the podcast. But I love that concept of, hey, have someone on who is a friend or it feels like just a conversation of friends.
And then everyone feels like you said, they're just sitting around the coffee table listening on this conversation. Well, you don't have to be a gotcha questioner to get people to open up to you, which is my least favorite form of interviewing.
Yeah, is this like, I'm in this port. And so I'm also a big fan of Jordan Peterson.
And I've been, you know, I just I've just read beyond order, which was which was amazing. And I've been rewatching a lot of his stuff from two years ago before he got sick.
And I just watched these interviews and not so much for the interviewer, but for how he handles them personally.

But just you never get what you want.

Like there's no that being that hard hitting or I'm going to ask you the question no one is willing to ask.

That that method, in my opinion, never actually gets you. You might get an answer, but it's surface.
If you can, as you said, bring them in and look, maybe you don't get it out of them. I guess you're taking more of a chance by trying to really make someone feel comfortable and doing it in an honest way.
Because they come out with it. Like you, you may try to prod them and they may say no, but it, it, that would, Oh, I would always rather that then I'm just going to hit you with this hard question.
If you say no, then you look like a jerk. And you know, I look like a superhero who wants, who wants to be that person.
I mean, I guess a lot of people want to be that person, but certainly not me. Yeah, no, I agree.
Like you, if you look at the interviews of other people interviewing Jordan Peterson, they're all, they're all horrible. And so you can see, oh, the average interviewer is really not that good because they all just don't listen to him and they're just trying to get their own agenda out.
And he, people think he, people without knowing think he's like some bad, weird guy, but he's not. He's like one of the most generous, nice people I've seen.
And people have totally misunderstood his whole thing about language and the issues he got in trouble with. But yeah, he's, he's a, I've interviewed him.
He's a really good interviewee. And I asked him, I think after the podcast, I asked, or maybe it was during, I asked him to sort of help me figure out where I stack on this.
And he's like, you need more confidence. And I've took that to heart, his advice.
I remember when he, I think you put that on air. That was, I don't think I remember that.
Yeah, he, yeah, he, his first book, or his second book, I guess the first book that I read, the 12 rules for life was a big, I took the concept, it embedded the concept of personal responsibility into me as a person. You know, I knew of it, you know, I knew the idea.
I probably gave it lip service. That book really wedged that concept into me and probably made me better in a lot of different ways as hopefully as a human.
I certainly, I certainly do. Dude, I, I, we're coming up against a time and I want to be respectful of your time.
I had like a whole bunch of questions, none of which we got to maybe just a couple of quick ones before, before we got out before we got to run. Yeah, sure.
My favorite quote from skip the Line is, you can't think your way to success. Whatever way you think is important.
I find in my space, in the insurance industry, the type of people who fall into our space tend to be, this is a broad stroke, thinkers, overdoers that now they obviously do because you

have to be able to sell and operate to run a successful business for sure. But they tend to

be over thinkers. And I would love when I heard this, I was like, I got to ask him about this

in, in, in help people put this idea into context. Yeah.
So I mean, a lot of people,

you know, like, for instance, I just described this thing about a zoom related product that I'm making for podcasters. So it's great to think and think and think like, this would be good.
This would be good. This would be good.
One day when I get a chance, I should do this. You know, you should just start doing the more you do.
like one action of doing is like I don't know I'm making it up but like a million thoughts about it and or a hundred thousand thoughts about it and and it's really important because I could think all I want like oh this would be a great product and you know I don't have the time to do it but it'd be great or or I'll do it but first I No, you can do a simple thing. You could, here's one thing I could have done.
I could have asked other podcasters, do you think this is a good idea? It's actually a good way to market because everybody will be asking later, hey, did you finish that? I'd like to use it. And, or I could do by, let's say I want to make a new clothing line.
You know, I had this idea a year ago, hey, if we're all going to be indoors for the next six months or however long, what clothes do you wear indoors? Well, the most comfortable clothes in the world are pajamas, by definition, because you could sleep in them. And I said, well, we no longer need to go to work.
We no longer need to wear a suit or whatever. What if I make outerwear? What if I make clothes that have the design of outerwear, but are actually pajamas in terms of materials? And so what can I do? I'm not a clothing man.
What am I going to do? Call a manufacturer and make some pajamas that have outerwear designs. I just started wearing pajamas everywhere I went, whether it was a plane or a restaurant or meeting people and see what people's reactions were about why I was wearing pajamas.
And these are simple doings. Or let's say I have a book I want to write.
Well, here's like 20 articles I might've written about the topic I want to write about. I'm going to print them up and staple them together.
And that's the first draft of my book. I just created a book in like 20 minutes.
And now is that the book, the final book? No, a book goes through 30 drafts before it becomes an actual book. So the final product will be very different, but I did something and I can hold it in my hands.
This is my first draft. And, and people say, well, isn't that a bunch of articles you just stapled together? Yeah, but it's my first draft.
I did it. And cause have they done? Everybody wants to write a book.
They're like, oh, well, I got to sit down and write it. I'm going to go to a monastery for three weeks so I can have peace and quiet.
Well, why don't you just talk into a tape recorder for a couple hours and you have at least three or four chapters. Get the transcripts.
Print it up. And that's your first draft or your first draft or your first third of the book.
So there's always something you can do to move forward. Okay.
Like, well, I could say, well, if I were running for president, I would do this, this, and this. Well, okay.
Here's an idea. Go to fec.gov, which is the Federal Elections Commission website, and it will take you about 10 minutes and you could file file to run for president.
And guess what? Once you file to run for president, it actually makes you start thinking about it in a more clever way because doing also is a cognitive bias. When you do something, it tells your brain, hey, this is kind of important to me.
So cognitive biases start to kick in about what you should do next and how you think about something. So thinking doesn't trigger that.
The brain enjoys just thinking about bullshit all day long. It's kind of masturbatory to a certain extent.
Yeah. But when you actually do something, the brain like snaps to alert and like, oh, he just did something.
Do I need to help him with this? And the answer is always yes. Like, yeah, I wouldn't do it without a reason.
That's what the brain thinks at least. And so it starts making you think differently about things.
So doing is actually a great way to improve your learning and your interest in something, which further spirals into more, it's like a virtuous cycle, spirals into more learning and so on. And then when you do stuff, you get to see, oh, that was easy or, oh, that was hard.
And you actually learn things you would never learn by thinking. Like I can say to myself all day long and talk at cocktail parties, you know, why don't we make suits made out of pajama slash silk cotton, whatever.
And people like, oh, that's so clever. And they sip their wine and drink and have hors d'oeuvres or whatever.
But if you actually like are partly doing it, you could say, no, really, I'm wearing pajamas right now. Can't you tell? And they're like, no, I can't.
It looks like a suit. And I'm like, yeah, it's a suit, but it's super comfortable like pajamas are.
Now you've actually done something that costs you nothing, really. And that's why in the book, Skip the Line, I have this concept of the 10,000 experiment rule instead of the 10,000 hour rule, which is the idea is, is that if you do things that are experiments to try to learn from them, and, you know, every experiment almost by definition has low downside, what's the harm, and high upside.
If this works, it'll be amazing. And if you're just sitting like every day, just thinking like, here's how I can get better.
Here's how I can get better. Well, I never thought of it that way, but you won't get anywhere as far as by actually doing things and learning that way by experimenting, testing ideas out, and so on just by doing.
It's such an important thing. James, I really appreciate your time, man.
This has been a lot of fun for me. I had no idea where we would go.
This is why I don't normally put stupid notes down on a piece of papers because I never actually get to any of them. But if for all you listening, I highly recommend I'm running for president 2.0 or running for president 2.0 with Phil Stott.
That episode is, I freaking love that episode. Whether you ever have any intention of running for president or for, uh, for, for marketing, for, for how you dialing to your customer base, your audience or whatever you're trying to do.
I thought that episode was really, really good. I mean, some of the things that you guys dial into it, it's very interesting to me, but the book skip the line.
And then when you go to skip the line on Amazon, it's going to pull up, choose yourself as like a buy this book to get that one as well. If you haven't already, both of them are absolutely tremendous.
James wrote a ton of books. Those are the two that I would read first if I were you.

And James, man, I just appreciate that you keep doing your thing, man.

I appreciate it, Ryan.

Thanks so much.

And look, let's stay in touch.

And I'm happy to come on again at some point.

Awesome.

Thank you.

Talk to you soon.

Good luck with Brian Keating.

That's going to be a great one.

Yeah. Close twice as many deals by this time next week.
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This is the exact method we use to close 1,200 clients in under three years during the pandemic. No fluff, no endless follow-ups, just results fast.
Based in behavioral psychology and battle tested, the one call closed system eliminates excuses and gets the prospect saying yes, more than you ever thought possible. If you're ready to stop losing opportunities and start winning, visit masteroftheclosed.com.
That's masteroftheclosed.com. Do it today.
Building a business may feel like a big jump, but On Deck small business loans can help keep you afloat. With lines of credit up to $100,000 and term loans up to $250,000,

OnDeck lets you choose the loan that's right for your business. As a top-rated online small

business lender, OnDeck's team of loan advisors can help you find the right business loan to fit

your needs. Visit OnDeck.com for more information.
Depending on certain loan attributes, your

business loan may be issued by OnDeck or Celtic Bank. OnDeck does not lend in North Dakota.
All

loans and amounts subject to lender approval.