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Ryan Hanley

Rogue Risk

Ryan Hanley

@0:17 - Gabriel Flores (The Shades of Entrepreneurship)

 Hello everyone and welcome to The Shades of Entrepreneurship. This is your host, Ryan I'm here with Ryan Hanley of Rogue Risk.

Ryan, how are we doing?

@0:37 - Ryan Hanley

It's my pleasure to be here, man. We're doing great. It's a beautiful day in upstate New York.

@0:42 - Gabriel Flores (The Shades of Entrepreneurship)

So we don't get many of those. So we take advantage of them when we can. Yes, I was actually telling Ryan right before going to show of how this podcast card that started is up in Syracuse up in upstate, little bit north Syracuse or New York, I would say.

But yes, they're very seldom really. He's no really pretty side-tays around that area. Yeah.

@1:04 - Ryan Hanley

So I went to school at the University Rochester, so about an hour west of Syracuse. And I live in the greater Albany area, so about 2 and 1 half hours from Syracuse.

And I think in Albany, we get 66 days of sun a year. Syracuse, they get like 62. And in Rochester, I think it's under 60 days of sun a year.

@1:26 - Gabriel Flores (The Shades of Entrepreneurship)

It's crazy. Now, folks, listen. I want you to understand, this is days. Now, percentage of the days.

@1:32 - Ryan Hanley

This is individuals of sun.

@1:34 - Gabriel Flores (The Shades of Entrepreneurship)

Yeah, it's crazy. two months of sun. That's why everyone's a little ornery up here. you come to New York, very nice people, hardworking, blue collar.

You know, I enjoy being from upstate New York, but everybody's got a little bit of ornery-ness in them. it's just that, uh, might have indeed division C, you know?

I didn't say it. I didn't say it. All right. So Ryan, go ahead and introduce. Could you please introduce yourself and share a bit about

Your educational background, career journey, and any personal experience that helped shape your entrepreneurial journey.

@2:06 - Ryan Hanley

Yeah, so I take people just back a little bit only because I think it gives context to how I got to be what I am today, which is the CEO and founder of a national digital kind of commercial insurance agency called Rogue Risk.

I went to the University Rochester, as I said, was a math major mostly because I flunked out of engineering school and tried a whole bunch of crappy, big jobs American Express.

worked for our accounting firm and, you know, the companies, I'm sure, are fine, but my role in them was terrible and hated it.

It eventually met a young woman who I wanted to marry and when I asked her father, know, is it, you know, I'd like to marry your daughter, can I have your blessing or whatever.

He kind of sat me down and did like a mafia oh so style like made me an offer I couldn't.

He was essentially, he owned an independent insurance agency. And he basically said, I think because he didn't want his daughter to be married to a bum, he said, hey, will you come?

I would like you to come work at the agency. So basically I became an insurance agent as the dowry for my wife's, well, she's my ex wife now, but my wife's hand in marriage, basically was the deal.

And, and I was, I was terrible at it. I just struggled and I just, I couldn't, one, I didn't at the time understand the value of the product that we were selling or what we were actually trying to do.

I just thought we were selling stuff, you know, I didn't, I didn't think through what insurance really meant and look, insurance is not a sexy product.

Most people hate it. Most people, you know, kind of, it's synonymous with, Huxterism and, you know, just kind of the worst qualities, the worst type of qualities that people have.

Associate with big business. And I'm interested in this, but I'm not sure if you're in But I had no idea how to sell the value of the product.

So I was terrible at it. And after about 18 months, father-in-law sat me down and said, he basically tried to fire me.

And I literally got down on my knees in the office. I was on my knees in the office. And I basically just said, I will do whatever needs to be done to not have you fire me right now.

And he agreed and he agreed to give me more time. But I had to do something different. I had been doing it the traditional way.

And that's where I kind of found digital media. This was 2008, 2009. The internet was still considered a fad by some people, especially in the insurance industry.

So I just started adopting basic principles and other industries and applying them to insurance and things. Everything started to change from me because I was way ahead of my competition on LinkedIn, on blogging SEO.

There was a time when was the This small independent insurance agency in Upstate New York was the most trafficked YouTube channel in all of insurance.

And there's a lot there, but I did that for eight years. And essentially, they came back to me, her family came back to me and said, you know, we love you, but your name will never be on the box.

You'll never, your last name is different than ours. So you'll never is never be anything more than a producer here.

And that, you know, I was in my early 30s, if that was just an unacceptable answer. just had too much entrepreneurialism, even though I don't know that I could have classified it that way at the time.

I just couldn't accept that. So I took a series of other jobs in executive positions. was a CMO for two different national technology companies in the insurance industry.

I then was a CEO of a fitness franchise and was summarily fired from all three of those positions. And in that really when the core, the core of it was, I was an entrepreneur.

I wanted to be a leader. had a vision for these companies and the stakeholders, the equity owners of those companies didn't.

That's not what they wanted. They wanted a bureaucrat. They wanted someone who would come in and, you know, make 17 page decks to describe why we were, you know, adding a new conference table to, you know, whatever.

And I just, I didn't do that shit. I was like, I want to grow. I want to win. I want to develop people.

And that's that's what I'm going to focus on. And I'm not going to do all this other nonsense. And I'm just, we got fired over and over and over again.

Essentially, essentially I found myself sitting in at 8 30 every morning. was working for this fitness franchise. We had six locations.

And when I started, we had 2000 members. And in nine months, I took us from 2000 members to 3200 members and two more and two new locations that were just opening and cranking.

So I think we're doing great. And we were doing great. And I'm sitting there 8th or 8th the morning on a Monday.

And the best part about being a CO of a fitness franchise is you literally just show up and like woo woo gear every day.

@7:09 - Gabriel Flores (The Shades of Entrepreneurship)

That's like your outfit, your uniform. Yeah, that's awesome. That's We just show up in scrubs. Right?

@7:15 - Ryan Hanley

Yeah, you're in your part of your job is working out at noon with like the with the clients. You know, that's like what you did.

So I was loving life. was home. wasn't traveling. It was great. And, and the, the founder came in. And except he came in a suit with his attorney and said, Hey, you've done a great job, but I want to be the CEO again.

I was his biggest expense. That was long story short. I done a great job. I'd grown his business. I got him way past profitability.

And I was as large as expensive. He just caught me and I said, I can't put myself in this position again.

I can't be beholden to some, someone's whim, someone's own personal self interest. Like, you know, I have a family.

Yeah, I have my own life that I have to live and I have to look out for myself. So at 8.36 am on October 6 of 2019, I was jobless walking through the parking lot of this of our headquarters.

And I decided that it was time to start my own company. That company was going to be an insurance agency that that I had kind of mapped out in my mind with some differentiating core values from what you see in the traditional space.

And that was going to be my goal. And I started it seven days before the zombie apocalypse, March 9 of 2020.

So we're still here. We survived the zombie apocalypse, thankfully. it was a very interesting journey. was 40 years old when I became an entrepreneur.

@8:51 - Gabriel Flores (The Shades of Entrepreneurship)

Wow. And that's a great story for anybody who's listening. doesn't matter what age you are, you can become an entrepreneur anytime in your life.

@8:59 - Ryan Hanley

you kind of alluded to it. Now, what is this current venture of business and what inspired you kind of kind of alluded to it again, but what really inspired you to pursue this particular you mentioned insurance so one what is it and what inspired you to pursue this particular entrepreneur and whatever.

Yeah, so there's some realities. If you spend too much time in the insurance industry, you develop an arcane set of skills that do not apply anywhere else.

@9:23 - Gabriel Flores (The Shades of Entrepreneurship)

So I didn't really have a whole lot of places to go.

@9:27 - Ryan Hanley

So, I had spent so much time in the industry, both as a low, you know, seeing kind of what a local small independent traditional agency can provide what the best parts of that business were what the parts that I thought were kind of holding it back.

And then being that I was an executive for two different national technology companies in the insurance industry, I got to see the other side of the space, the entrepreneurs, the Silicon Valley startups, the tech, the fast moving, I got to see both right.

So, I wrote down a couple core ideas. To start this business, I wrote down the term human optimize. So what I felt was an issue in our space was there was really a dichotomy.

Sorry, a polarization in our industry. You had people that, but the humans were the problem and that tech automation, all these things, that was the future.

needed to get humans out of the transaction as much as possible. And then you had this very traditional side of the industry, which thought all that stuff was nonsense.

None of it helped. All of it was just distraction and that really, you know, pounding the pavement, human to human press the flash, know, shake hands, kiss babies.

That was the best way to do it. And all, all my idea was, I'm, I'm going to cherry pick the best ideas for both and put them together.

So, so the kind of idea that I wrote down was, let's assume. If we were going, right. So in order to be a successful entrepreneur, you have to be solving a specific problem.

You believe exists, right? That's kind of a core aspect of entrepreneurialism. So the major issue that I wanted to solve first was the service issue.

So what that means is let's say, let's say the cost of service in the insurance industry is very high.

It costs a lot of money to service insurance. So let's say you have an issue, Gabriel, and you call my agents.

In a traditional agency, you're going to get. But the person's going to get you on the phone, to figure out what your problem is as fast as possible.

Say they have a 20 minute block of time to spend on your problem. Okay. So we're going to try to spend the least amount of time on the phone with you as they can.

Because they know it's going to take 15 to 17 minutes to actually process whatever your problem is. So they're spending this tiny little amount of time on the phone with you, the customer, the person actually matters.

Because all this data entry in this system. And that's it in all its not okay. So what I wanted to do was flip that on its head.

I wanted to create technology, automation, self-service, issues like that, so that my service people, my team, could spend 17 minutes on the phone.

Gabriel, what's going on? Why is this a problem? How do we make sure it doesn't happen again? What other problems may you have?

Let's really get to know you as a customer, make sure that you're properly serviced, that you're happy with what's going on, that you feel like you have a trust, knowledge that you need to continue to interact with us.

And then we have everything baked in in the background from a technology perspective that then only takes three minutes to do that transaction.

So to me, that's what I call human optimize. Put the humans in the positions where they add the most value, remove them from the places where they do not add value.

So that was core value number one. Core value number two was what we call no ceiling insurance career. I've never wanted, because your last name is Flora, a mind is handily, that you couldn't make all your...

While the streams come true in my business that someday you couldn't have a partner track that allowed you to own an asset relating to your work here.

I never wanted your last name to impact your ability to build a true asset for your family with our company.

So that's the second. And then the third was an idea of no customer left behind. In our industry, it is incredibly difficult to make money on small business, small business accounts the main street there's 30 million of them.

It is incredibly difficult to be profitable as a business as much as that might sound crazy to people listening.

You pay $3,000 in insurance premium for your business. I'm making $300 before I pay any of my systems. I pay any of my people.

I pay any of the bills. I'm making $300 in that account. Me. So like, I'm not making three grand.

You pay 10. Right. Basically, you make 10% commission. So like, you're, you have to write a tremendous number of those accounts.

And then the service needs stack up on the back. So like, it's very difficult. So what happens is, so what happens is that small businesses get shit on, basically.

They get crap service, they get these, you know, automation tools that don't really help them or they just get shoved through a system and they get treated like a number.

And what they get is very poor service, very poor understanding of the product they're purchasing. And that is, I wanted to make sure that these small businesses, the core of our country, what makes our country such a great place, the ability to own property and to own an asset and to start a business that can't be taken from you, insurance protects that.

We're in the sustainability business. That's what we do. Insurance is a sustainability product. I wanted to make sure that you, Gabriel Flores, who owns this small business, that you were able to have the same level of service, the same level of access to products that someone who runs an enterprise.

Level company with thousands of employees gets. And those three core ideas set the bedrock for rogue and that's what we've built upon to this day.

@15:08 - Gabriel Flores (The Shades of Entrepreneurship)

I love it. Now, why would you say, you know, why is it important to not only serve your employees, but also serve the customers?

@15:19 - Ryan Hanley

Why, in your opinion, why is that so important? Yeah, employees are always more important than customers. There's 30 million customers for me in the world.

But I only, but I have 20 employees. Well, if you count our virtual assistants, we're at 25 and those people, if those people aren't happy, if they don't have fine meaning and purpose in their job, if they don't like showing up, and they, it doesn't matter how hard we work to create a great product.

It doesn't matter how good our sales process is, how good our marketing is. They're not going to do a good job for our customers.

So your people have to be happy first. You can solve so many customer problems, so many product problems. Great people in your company who feel supported, who feel pushed.

Now granted, I don't want to give away some of my politics or whatever, but I do not believe in the safe space bureaucratic mentality that we have developed today in our corporate culture.

I think that a lot of it is nonsense. I do believe in a meritocracy. I do believe that people need to be pushed.

I do believe that people need to be held accountable, but at the same time, we have to treat them like humans.

have to give them a place where they can feel safe or they can feel like they can push back.

Right. What I find is in most of the bureaucratic organizations that I've worked in, is they, they confuse being able to share your opinion with your opinion being good and mattering.

Right. So those are two different things. You, if you work for me, you can share your opinion with me and there is no repercussions.

You can say we're doing this wrong, or I don't appreciate this, or you said this this way and I didn't like it.

That's great. You can say all those things. I don't have to agree. I with you.

@17:01 - Gabriel Flores (The Shades of Entrepreneurship)

That's the difference.

@17:02 - Ryan Hanley

And unfortunately, I think what a lot, how a lot of people as leaders get caught up in is they feel like just because their employees say something that they have to take action on that thing.

And that is not the case. In my opinion, it's, you should be able to say whatever you want without that.

That's, that's the beauty of America as you can. You can share with me. I want to hear it. I just don't have to agree with you.

And so we are like a merit based organization. We hire a lot of. Single moms or moms at young kids because our industry tends to throw them away because their schedules are less flexible.

So we are fully remote work from home. And I have this just incredible team. And like I said, we, we bring on a lot of single moms and moms and young kids because we have the flexibility in our business to that their lifestyle needs.

And we're getting rock stars that other agencies and insurance organizations have thrown away because they can't work a traditional 830 to.

For 30, know, punch the clock kind of thing. We hire adults and we treat people like adults. If you got a steal an hour in the morning because your kids throwing up, go deal with your kid.

Take care of your kid. Get that square away. them safe. Get them happy so that you, when you do show up at 930, you're ready to rock.

Your mental is here and you're with us, right? Where other places, you're scrambling. You're running around. Another rest of the day, you're thinking about this sick kid that you didn't really get to take care of and you're feeling bad as a parent or you don't really know where they're at.

So like, so it's a it's a give and take. I expect that on the back end. I expect you to get me that that hour back somewhere, right?

But I'm going to treat you like an adult and assume that you're going to get it back. I'm not going to have it in some system where I'm like you owe me an hour or whatever.

Not if you can't trust the person to get you that hour back, get rid of them.

@18:51 - Gabriel Flores (The Shades of Entrepreneurship)

That's that's what it is. I'd agree. I think I think that's one thing that a lot of people can take away is, you know, having autonomy in your role of being empowered, feeling like the empowerment.

I like make the right decisions, but also to your point, being held accountable for those decisions. work in healthcare and there's so many times where my words can truly affect massive relationships, huge relationships and can swing in various ways in the healthcare industry.

And so my relationships with others is very important. I have the autonomy to make those decisions and have the empowerment.

However, if I make the wrong decision, if I say the wrong thing, I should be expecting to kind of get that call to the office and hey, what exactly was this?

let's kind of bring it back to the business area. What you're in the insurance world. Let's talk about the benefits of utilizing insurance as a small business owner.

@19:43 - Ryan Hanley

Yeah. So, so talk about insurance. Everyone talks about insurance as protection. And if you went and checked out our website, you'd see we use that word to.

But to me, insurance doesn't protect you. You know what I mean? Like, if you're a pipe burst, we're not there.

Like grab it and, you know, fix the pipe. mean, eventually, someone's going to go. Insurance is about sustainability. So what we're trying to do is create a series of financial levers that allow you to sustain your business when something really bad happens.

That's what that's what insurance is. Our economy runs, whether we like it or not on insurance. If insurance didn't look outside your window.

The buildings you see they would not exist if there wasn't insurance. The bank wouldn't give you a loan. You wouldn't have credit.

People wouldn't buy stuff. All these things are levered on the back of insurance. That if something really bad happens, there is this product which comes in and creates sustainability.

So when we think about insurance, I try not to get people to think about protection. That's the wrong way of thinking about it.

It's, do you want, if you have a really bad day, do you want your business to continue to exist?

This simple yes or no? If the answer is no, then screw around with insurance. Don't really take it seriously, buy the cheapest thing, do it, right?

If what you're saying is the hard work, the effort, the time, all the stress, all the anxiety, all the hours, those are meaningful to you, and you would like to keep that business going if you have a bad day, then an hour a year of thoughtfulness to your insurance with a professional that you trust will make sure that that is as close to reality as possible.

And so what do I mean by bad days? Well, if you own a shop, right, you own a shop.

Someone drops a bottle of water on the ground slips and falls in your shop and breaks their head. Right, we have an aging population.

My dad just had hip surgery last year, right, because he, well, he did it because he placed too much golf, but, you know, I actually had an aunt who slipped and fell broke her hip had to ever hit replaced, right?

So like these things happen all the time. we can say it's not going to happen to us. We can say, you know, those are all things.

Thank you for those are excuses.

@22:00 - Gabriel Flores (The Shades of Entrepreneurship)

It's not reality. How about let me give you an example of maybe you can kind of tell me how insurance can help.

So obviously Portland, Oregon, we have a lot of a trans it's in our community. This is not this is not say bad thing.

These are individuals that are kind of down on luck right now. We're trying to help them out now with that said we do have individuals on our community that also unfortunately just love destruction.

Right. And fortunately our small business community has been hit hard by a lot of theft and break ins and vandalism.

How and how does insurance kind of help that that community.

@22:34 - Ryan Hanley

So let's say you have a storefront and someone's high on fentanyl grabs a rock and throws it through your front window.

Replace. Let's say that person decides to then take a lighter light piece a newspaper on fire and throw it in the front window after they throw the rock through that fire burns down your business.

That's insurance. Let's say. I Let's say you, one of those people comes in, right? So one of the things that's happening across the country right now is vagrants or whatever, they're doing, there's a lot of insurance scams that are happening.

So a way to get money because there's a lot of unscrupulous ambulance chasing lawyers, especially in, and again, this is not a political statement, it's just truth, in more liberal states who allow for large-scale judgments from a liability standpoint, right?

You have these individuals going into stores and faking slip and falls, or actually hurting themselves and then going to attorneys and having them come after store owners as a way to go after the insurance money.

What they think is, I'm sure this business has insurance, I'm gonna come after them. If you don't have insurance and they file the claim, guess what?

You're still on the hook. They can come after your business. Let's say two people getting a brawl in your business, right?

see scenes from all over the country and this This is something that's happening. You have you have a brawl in your business between people, right?

So it doesn't matter who it is. could be, you know, take take vagrants or immigrants or whatever out of the question.

It could just be to run kiddies walk into your store and get into a fight. They can sue you because it happened in your building.

You are responsible as a business owner, whether you rent or not for everything that happens in that business. Now the physical damage stuff is fairly straightforward.

There are only certain scenarios where your state or town can actually kind of screw you if they, there are, there are some types of policies that will, that will exclude riot.

There are some that will exclude states of emergency. So if they declare something a state of emergency, that can kind of hose you up a little bit sometimes.

Those are obscure. But for the most part, physical damage is going to be covered most of the time. And then the liability one is where you really get hit.

So liability is you sell a product. And someone says it hurt them or it doesn't function properly. Someone gets hurt on your property, there's violence on your property.

Say you have to defend yourself, right? You have to, let's say you have to actually defend yourself. You're a shop owner, someone attacks you, you have to defend yourself.

Unfortunately, in a lot of states, the person who initially attacked you can then sue you. And in that case, insurance is going to be what defends you.

And people don't realize that in most insurance policies, that's first dollar defense, which means that you are not going to have to pay for that legal work out of pocket, that insurance company is going to pay every dollar from dollar one to defend you up to your liability limit.

Now, the other thing that I'd tell you what's happening outside of the scenario that you described is there is a lot of interpersonal lawsuit happening.

And what I mean by that is sexual harassment, Those are really big ones where business owners can get hung up is that the laws are not meant to protect the businesses.

They're meant to protect the individuals. So let's say you interview three white people. Someone who isn't white can sue you because you interviewed for a position and did not interview someone of that wasn't white.

You could just be like, I didn't even realize I just interviewed three people. The third person was great. hired him.

I wasn't even thinking about it. Right. Um. And that in some states, that's illegal. You can't do that. And it doesn't matter that you're a small business.

It doesn't matter that you don't have the time. It doesn't matter that you didn't know the law that you're you're going to get sued for that.

@26:41 - Gabriel Flores (The Shades of Entrepreneurship)

I mean, look at the NFL. They have the Rooney rule that was created. know, I think, know, one of things you mentioned to their piece was you're talking about also individuals that are kind of strategically going out there and trying to find reasons to create a issue.

A great example. Former guest. Large company. They were actually, and this is starting to become a trend. So small business owners, please take heed of this warning.

Your website even is becoming targeted if it is not in compliance with ADA rules. Now again, 88 year thinking like wheelchair access into a building, but you also need to have the capabilities for individuals that maybe have hearing impairment or reading impairment to access your website.

And if not, more are now targeting those websites and coming at them and suing them for not being ADA accessible.

so again, this is not to say this is any, I think people are just taking advantage of opportunities, just like we saw during the pandemic and then the PPL loan or the PPL loans, right?

And then people really took advantage of those opportunities. There are people, unfortunately, they're out there. They're going to try to take advantage of small businesses or individuals in general, right?

is just kind of a Really nice to have it when you need it. Like, sure, I understand sometimes probably sucks to have to pay for it because sometimes you're like, man, I don't need it.

Like, but hey, I get glasses every year because I pay for insurance. now, Ryan, how can businesses use insurance strategically to gain a competitive edge and outlast arrivals?

@28:18 - Ryan Hanley

Yeah. So to me, I think of insurance as the foundation upon which you grow your business, right? You want to hire new people.

You want to expand and grow. Like I said, you're going to need EPLI because if anyone knows you have humans who work for you, they're going to bump into each other.

They're going to piss each other off. Someone's going to say the wrong thing. You're going to have problems. The larger you get, the more apt you become a target from a cyber attack, right?

So if you want to grow and grow without major obstacles creating financial instability, you have to have these products in place.

are the foundation upon which you grow your business. Business owners policy, workers comp policy, commercial auto policy, there are a lot of people driving around doing

Commercial work in their personal vehicle and don't realize that if they get into an accident doing a commercial job with a personal auto policy, your personal auto carrier 100% has every right to deny that claim and they're going to go, insurance is the worst but but you don't, you did not do your job.

Your job was to adequately and accurately describe the usage of that vehicle, which was commercial purposes, you tried to save a few bucks by having a personal auto policy.

And that's the nature of the deal. So like there are, it's not, insurance is tough because, again, you're getting a promise, you're paying all this money for what we don't even get paper documents anymore, right, we just get an email that says, hey, you have coverage now.

And that's it. That's it. It's a difficult thing for people to wrap their their head around that value. But I have seen over and over again.

give you an example. I had a, I have a furniture store, a large furniture chain. That's a client of ours.

And they got. A, my client, the owner of that business, got an email from one of his larger customers who frequently buys furniture from him.

Hey man, what's this? What's this $50,000 we spent on furniture? So my customer goes into my client goes into his database and he said, we don't have a we didn't charge you $50,000 for anything we didn't we didn't we don't have a transaction the record.

So a hacker spoofed the email address of my client sent an invoice to this to his customer for $50,000.

The guy saw it, boarded it on to his account executive or whatever she paid the bill. Didn't even think anything of it.

Three months later, they're going through their finances, you know, going through the records and they're they're wondering exactly what they got for this.

Come to find out. That's a cyber liability claim. That's that's that's that he that guy got that guy got.

It's social engineering, but yeah, they got they got spoofed and that my client didn't do anything. And he. But he's responsible because the person who spoofed him used his name and a version of his brand in the email address.

It was like, you know, name, underscore, name, underscore, whatever to get to it. And the guy just didn't, you know, he's just moving fast as we all do.

And, and here he got, he got took for 50 grand and the cyber policy had to pay. So 50 grand to him, thankfully, even if he did have to pay it out of pocket wouldn't have like, killed his business.

But I'll tell you. You four years ago, when he first started that 50 grand would have been enormous hit on him.

I mean, possibly even like a game changing hit for him. If you know today he's big enough, but he didn't have to pay the cyber insurance.

So that's the kind of thing where like you're just going about your day. You didn't do anything wrong. You didn't, you didn't make any mistakes.

You didn't even click on a link. This, they just used your likeness to to to socially engineer this other business got $50,000 on him and you're responsible.

So it's like, these are the kind of. Things that, again, it's sustainability. It's how important is your business to you long term?

It is, in my opinion, you don't need every insurance policy that exists day one. I think if you work with a broker, and this is something that we try to do, and I try to train my people on, is we don't want to be hooksters.

We're not trying to sell and maximize everybody's account to the max number of policies they could possibly buy every time, We want you want to try to work with someone who's going to understand your current situation.

You don't need a commercial auto policy if you're not using your vehicle for commercial auto. You may not need certain endorsements on your policy if those things aren't appropriate.

When they are, you can add them, but, you know, so be smart about what you buy. don't need to get, I'm not trying to scare anybody into go out and buy every policy that exists.

That might impact your cash flow, and you might, that might hurt your business. But by working with someone, having honest conversations, you know, lot of times small business owners rely on the truth.

If they're an insurance agent, because they feel like it's going to save them on premium, that is, if you have to do that with your insurance agent, that is not the right insurance agent to work with.

Find someone who you can have an honest conversation with who isn't going to push products down your throat that you don't need, but will help you strategically build a portfolio of products that matches the risks that you actually have.

And you will, you'll find them when these really terrible things happen and hopefully they never do. But if they do that, you get a check from the insurance company because here's what I do not.

It's not the 1700s anymore. If something bad happens to your business, the town is not rallying around you to put your business back together.

If your business burns down tomorrow and you don't have sorry, it's a story in the newspaper. People forget about it within a week and you're sitting at home no job and no business.

everyone's just like, that's too bad. We're sorry. If you have the insurance policy, a check comes in the mail two or three days later and you're rebuilding your business already.

And. You know, I've just seen it too many times. mean, that example I gave you about the furniture thing, that's one of a thousand examples I have of just all the crazy wacky, stupid, you know, things you just could have never seen coming that happened.

That could be a bumps in the road. They could be just little nuisances, or they could end your business if you're not properly detected.

@34:24 - Gabriel Flores (The Shades of Entrepreneurship)

Now, what would you say? Because you mentioned, you know, trying to avoid working with some insurance companies if you're trying to negotiate prices.

One, what questions should small business owners entrepreneurs be asking insurance companies? then two, what are some of the red flags that an insurance company says this might be a red flag?

@34:44 - Ryan Hanley

Yeah, that's a question. So the first thing I'm going to tell you is, and everyone's going to think this is a sales pitch.

guess you could say out in the marketplace. you do not need to work with us. What I'm saying is, if you go direct, your.

For the insurance agent, a lot of small business owners being entrepreneurial, being self starters, they think if they go online or they go direct to a company that they're just they're making the smart decision I'm cutting out the broker I'm not going to pay them a fee.

Well, one, understand that you are you are not paying less by going direct. That's just not the case to you become the insurance agent.

So let's say I give you bad advice. I say, you know Gabriel. You know what an Oregon. Workers comps kind of like a secondary thing.

You don't really need that man. You're good. You're fine. And someone gets hurt and you get sued. That's an Arizona missions claim on my insurance policy that I have.

I'm a professional just like a financial advisor, just like a lawyer, just like a doctor, just like a dentist.

I have errors and omissions insurance, right? So I give you inappropriate bad illegal advice. That comes back at me.

So now you're you're by working with a broker, you are protected in you have an extra layer of protection and.

And you can come back after me if I don't do my job correctly, especially if I don't do my job correctly intentionally.

So you become the broker if you go direct. So if something bad happens, it's not the insurance carriers fault.

They're selling a product. They're a manufacturer. They create the t-shirt. You're the one that's wearing the t-shirt, right? That's the way to think about it.

The insurance carriers are manufacturers. are manufacturing a product. They are not the ones who are supposed to be giving me the advice.

Okay, that's one. Do not go direct. Avoid going direct if you can. And if you have Geico and you're listening to this, you should slap yourself in the face and get rid of that company.

Because you are making a very bad decision. They have 11 exclusions that no other insurance carrier in the country has that they don't talk about.

And that's how their prices are blessed. So everyone thinks they're being smart. It's you're not. That means. Okay, so let's talk about this.

So, so go. Okay, so you should find a broker. First, use the smell test. Do you think you can trust them?

Like a trustworthy person. They seem like they have their best interests in mind or they just trying to blow through your account, sell you some stuff and move on.

Right? So use the smell test. You know, use your intuition. If that makes sense, then start to ask them real questions.

Like, what's your philosophy on protecting my business? You know, how do we make sure that I have the right coverage without having too much coverage?

Right? You know, I think if you're just shopping for the cheapest thing you're going to put yourself into in a tough place.

But it's very appropriate to ask them. How do you weigh the coverage you think is the best for me versus my needs from a price perspective?

Right? ask them these questions and see what they say. Everybody's going to have a slightly different answer. But how the answer is going to give you insights into how they think, right?

Because what you want is someone who's going to say, okay, I have three carriers I'm looking at. There's maybe three different prices, three different levels are covered or types of coverage or claims situations.

Right? like, a good example. I write a lot of business with the Hartford for small business. like to Hartford a lot.

Pricing is very consistent. Product is very robust. Claim's handling is very consistent. Are they the cheapest? Sometimes, not always.

Maybe less than 50% of the time are the cheapest. But what I know is when one of my customers has an issue with the Hartford, it's going to get taken care of.

They're going to solve the problem. going to figure out what it is. to the best of their ability, they're going to get that customer back to whole.

So if I have the Hartford and say, maybe I'm not going to name so negatively, but another company that maybe is even a hundred or two hundred bucks less.

If we're talking small business, maybe sometimes thousands less of we're talking larger businesses. But I know that when they have a bad day, it's going to be a pain in the butt, right?

It's they're going to they're going to haggle them. They're going to nickel and dime them. They're going to maybe they have some coverages that aren't in there that are kind of important.

I'm not going to present that to them. And I'm going to tell my customers that's my philosophy is like, I would rather you go do business with someone else.

That me puts you into a product that is knowingly going to not help you in your moment of need.

And since there's 30 million small businesses, I'm okay with you choosing someone else. It doesn't mean I'm going to put you in the most expensive thing.

And trust me, we don't make enough on a percentage basis for these differences in premium to mean anything to me, like, from an income perspective, it is strictly that I want to be able to look my customers in the face.

And there's many agents, not just me. so what I'm saying is I'm trying to embody what I would look for in an agent, not necessarily us.

Obviously happy to work with anybody, but there's plenty of agents that think the same way, but like, find someone who would feel who would be regretful or disappointed in themselves if they didn't properly take care of you.

Do any for the wrong reasons you'll you'll you'll be able to hear it, you'll be able to smell it.

I think, you know, how do you marry that as a good one? How do you pick which company you offer us as a good one?

How do I manage my budget versus all the coverages I should have? Do you have a way of creating a plan for me as I grow?

Those kind of things. And I think you'll get a good feel for what they're all about.

@40:20 - Gabriel Flores (The Shades of Entrepreneurship)

Yeah, and you know, this is a grid point not only for, you know, when you're looking at insurance brokers, but also as entrepreneurs, your differentiator sometimes is your customer service.

You know, if you, you can schedule a dinner at a five star restaurant at five thirty, but if they don't sit me down until six o'clock, I don't care how good the food is.

The service wasn't there. Right. When I go to Starbucks and I ask for my, you know, grande, he's not latte with whip.

I want it to be correct all the time, not sometimes not usually, but always. Right. And that's kind of the same thing with customer services.

We kind of want things to be done the same way. Boy, pretty consistently to your point, Ryan, we don't want to be nickeled in time every time we call someone.

Now, that was some great advice, I think, for the listeners and things to kind of think about and questions that ask for them.

And you also mentioned, hey, you'd be happy to work with some of these folks. So how do they get in contact with you if they're interested in learning more?

@41:20 - Ryan Hanley

Actually, first before I ask that.

@41:22 - Gabriel Flores (The Shades of Entrepreneurship)

What's the five year plan for Rogue Risk?

@41:25 - Ryan Hanley

Where do you see yourself in five years? Yeah, so we are. We. We are continuing to grow and expand.

We work with both individual companies. We also, a division of our company that we're continuing to grow is actually our partnership division.

So companies that have, say, client sets. One of them is we have a very large trucking transponder company. And what we've done is partner with them.

And we've created essentially a custom program for their customers, where the customers the trucking clients who. Work with them from a transponder perspective.

They now will refer them over to us and know that they're getting great service that it is dedicated that the product set was approved by the transponder company so they know what products were offering.

And now they know their come their customers being taken care of so we do a lot of that too.

So that's like a big part of our, but I'd say the core is getting. I want, I want to give people who are looking to have a light like I grew up poor as shit.

I did. People use my friends used to refer to my house a crack house. People used to say you could keep your doors open in our town because the criminals live there they didn't steal from there.

Right. It was 900 people we were in the middle of nowhere in the woods. Insurance. And entrepreneur is a mindset and the insurance industry has given me a life I could have never expected in a life that I could have never imagined that my kids have.

I'm very blessed. thing. lot of hard work but but but this is an amazing career amazing industry. It's challenging, it's thoughtful, yes, people will hate you, but you know you're doing something close to God's work and trying to protect people's lives and businesses like to believe.

And I want to give as many people who are as willing to put in the work the opportunity to experience this career and change their life.

And it doesn't matter, you don't need anything more than a high school diploma to work for real risk. We're not, we don't hold you to some crazy standard.

If you're hardworking, if you're willing to come in and be part of our team and buy into our process and work hard for the people that choose to work with us.

There's a lot of money to be made. There's a wonderful career, flexibility, you can have a life, you can have a family, and that's the part of the business that I really want to grow.

The clients will always come, right? we'll, but I want to give humans an opportunity to change the course of their life if that's what they want and selling insurance products.

It's particularly property casually insurance products. It is a wonderful career. challenging. It's exciting. There's big deals. There's small deals.

You get to work with all, learn about all these amazing people and especially on the commercial inside. You get to learn about all these businesses.

And then the variety of businesses that exist in the United States is insane. these people are crazy. mean, you talk to entrepreneurs all day, podcast.

That's what we do all day. We're talking to these wacky people. One guy was, you know, we just wrote a guy that he scrapes barnacles off the bottoms of boats off the coast South Carolina.

And he's talking about how he puts them in, he racks them and all the things he does. And like, I don't know.

I mean, it's just wild to hear about this guy's business and what he does and how he does and he loves it, right?

And makes, you know, makes good money. And so that's, that's really what I to, I want to get this process dialed in and start to put.

Not just, you know, today we have 12 producers. I'd like to have dozens, if not hundreds of producers someday coming through.

And experiencing what this career has to offer and hopefully giving them a similar change in dynamic of lifestyle that I've experienced over the 42 years of my life.

So that's really, that's really my focus as the leader of the company. Obviously we're always trying to expand into other areas but giving giving our people that that experience and that ability in that career path is is my big mission.

@45:25 - Gabriel Flores (The Shades of Entrepreneurship)

I love it. Now for the folks again at home, if they're interested in connecting with you, how do they find you?

What's your website, social media location?

@45:32 - Ryan Hanley

Yeah, awesome. So one, I just, I just appreciate the opportunity, man. love talking about this stuff. love talking about entrepreneurs.

so if you're interested in our company, you go to just rogue risk ROGUE and you can check us out.

Actually, we just launched earlier this week, the first ever commercial insurance search engine. So we're using, we've partnered with an AI assist company and we basically took, we have, we have thousands of pieces of content because education, obviously like the talk.

Education is a big part of what we do at Rolks. We have all these YouTube videos, all this, and we've indexed it all.

And now you can ask it questions and get all your answers right there. It's the first ever kind of AI-assisted search engine commercial insurance.

So can check that out if even if you don't work with us, even if you use it to hold your agent, like accountable to what they say, use it.

It's yours. It's free. You can go on and check it out. to do that. If you're interested in what I'm doing, I'll give you two places.

I create and communicate a lot on Instagram. I'm Ryan underscore Hanley, H-I-N-L-E-Y, Ryan underscore Hanley on Instagram. And I share all the entrepreneurial ideas, concepts, things I've learned.

journey has been crazy. And I try to share those ideas there. And if you like this kind of stuff, I write about it at FindingPeak,

You can check that out. And yeah, just appreciate the hell out of And this has been super fun and we should know about the best and same to your audience.

@47:03 - Gabriel Flores (The Shades of Entrepreneurship)

Love it and love it and folks again. So if you did not write all that information down, this is a great time to plug the Shades of Entrepreneurship newsletter.

All this information will be on the newsletter the week before the episode airs, the week the episode airs, and the week after the episode airs.

So Ryan information will be on the newsletter for three weeks straight. So again, to subscribe to that, please visit

Ryan, thank you again so much for coming on the show. I really do appreciate it. think you brought a lot of value to the listeners, especially in questions that I ask and things to avoid when looking at small businesses.

I really do appreciate your time. For those folks listening at home, again, please subscribe to And you can also visit us at the Shades of E on Instagram, Facebook and LinkedIn and TikTok.

Without that, thank you and have a great night. 

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