Entrepreneurship Podcast post

Continuous Improvement with Ryan Hanley

George Grombacher July 13, 2023

share close

Continuous Improvement with Ryan Hanley

LifeBlood: We talked about the necessity of continuous improvement, the challenges of intrapreneurship as well as entrepreneurship, dealing with negative situations, and finding success doing great work, with Ryan Hanley, Founder and President of Rogue Risk.      

Listen to learn why you’ve got to just keep moving!

You can learn more about Ryan at RogueRisk.com, FindingPeak.comFacebook, YouTube and LinkedIn.

Thanks, as always for listening! If you got some value and enjoyed the show, please leave us a review here:


You can learn more about us at LifeBlood.Live, Twitter, LinkedIn, Instagram, YouTube and Facebook or you’d like to be a guest on the show, contact us at contact@LifeBlood.Live. 

Stay up to date by getting our monthly updates.

Want to say “Thanks!” You can buy us a cup of coffee.


Invest in yourself. Bring it All Together.

Work with a coach to unlock personal and professional potential.

Our Guests

George Grombacher

Ryan Hanley

Episode Transcript

george grombacher 0:00
Hey, what’s up? This is George G. And the time is right, welcome. Today’s guest struggle, Paul for Ryan Hanley. Ryan, are you ready to do this?

Ryan Hanley 0:08
Yeah, let’s do a man.

george grombacher 0:09
Let’s go. Ryan is the founder and president of rogue risk. They’re an insert Insurance Agency aimed at helping small businesses reduce the complexity, cost and time waste with their insurances. Right? It’s also about your personal life’s more about your work and why you

Speaker 2 0:24
do what you do. Yeah, well, no one goes to the insurance industry, because they grew up wanting to be in the insurance industry. As boring is everyone’s hit their brain when they heard what I do for a living, I can promise you it is that boring. However, it’s also incredibly important. And what happens is, it’s a very nerdy profession. And you also develop this like arcane set of skills that’s not applicable in any other space. So if you, it’s like a black hole, like if you, you get a little too close and you spent a little too much time near it, you kind of can’t get out. But the good news is, there’s a lot of interesting challenges, you are kind of doing God’s work to a certain extent. Because as much as people hate insurance, if your business burns down tomorrow, or someone slips and falls and breaks their arm in your store, no one cares, no one’s coming to help you. The only people that are coming with a check to keep your business running is insurance. So as much as people hate me and our company and every other insurance company, you know, we all we all sleep well, knowing that we’re we’re helping people behind the scenes that’ll being said, how I get there was really a dynamic series of so everyone knows my son decided to come in you go what’s up? Good morning, buddy. That you want to use? You want to use this? Alright, go ahead. Give me like 15 minutes, I brought in close the door. Sorry. For the if we keep this part, just know that my son decided to walk into my bedroom at 130 last night and puke all over me. So we’re dealing with that today. parenthood. Yeah, he has Joyce parent, it’s it. So how I got in this business? I actually it was it was the payment for my wife’s hand in marriage. It was like her dowry, I guess I think her dad, her dad owned an independent insurance agency, a local agency that you’ve probably driven, you know, anyone who’s in the States has driven by probably 10,000 times you’ve driven by one of these places, these little local agencies that have someone’s last name on them and and, you know, I wanted to marry my boss. She’s not my ex wife, but I wanted to marry my wife at the time. And I think he didn’t want his little girl to be married to a bum. So like, he pulled me out of a Christmas party. And this is like, straight out of like Godfather something pulls me out of this Christmas party into his office, which is like, it literally it was like a movie, the high leatherback chair, wood paneling. And, you know, it’s like one of those offices that you look in, and you’re like, wow, that looks really nice. But that’s got to be completely uncomfortable to do any kind of work in. So we sit down and he’s like, hey, you know, I heard you, you know, not happy where you were. And I was working for American Express at the time doing like, consulting work. And it was, it was not, it was work, and it paid the bills, but I didn’t love it. And he said, Have you ever thought about sales, and I said, you know, I had actually I’m fairly outgoing guy and like to talk to people high energy, and I just said I have thought about it. It makes me nervous. I grew up incredibly poor and to to parents who are not entrepreneurs who, you know, kind of scraped by doing doing basic work. So I was never taught like to them, the, to my parents, the risk of being a salesperson was never worth the security of, you know, kind of a standard job. And so it made me nervous, but he said, hey, we’ll teach you you’ll be fine. There’s a lot of money to be made. It’s a good profession, all that kind of stuff. So at this point, I would have said yes to any job, you know what I mean? Like I just, you know, when he basically said, he basically implied, like, if you want to be part of this family, you need to come do this. So, you know, I wasn’t whacking people. So I figured that, it was it was worth the time. So that’s how I got in. And I did that for eight years. Unfortunately, the family business dynamic kind of got in the way. My, my my ex family, they, they only recently acts but at the time, they basically came to me and said, Yeah, you’re doing great work. But your last name is different from our last name. So you’ll never be anything more than just a salesperson here. And at 31 or 32 whatever I was at a time that was completely unacceptable to me. I just to think that there was never going to be a path to equity or partnership or anything. And just this is I was gonna be an insurance producer for the rest of my life. That was I just couldn’t handle that. So I put my two weeks notice in about two days after that conversation happened that was 2014. And I had become during that eight years fairly proficient in digital marketing, which in the insurance industry still is They’re like magic to every other industry, digital marketing his like, you know, table stakes, but in insurance, it’s still magic. So I get became the Chief Marketing Officer of a national technology company based out of Minneapolis, became a speaker. And I flew all over the country speaking, doing workshops, and running 20 person marketing department for this company, and we grew fast. And we, we built a sister media company brand, from zero to 500,000 eyeballs in less than four years. You know, we it was a really fun time put on a bunch of conferences. Unfortunately, it wasn’t an organization that valued intrapreneurship and my desire to grow, do projects, try things push, you know, I’m fairly ambitious guy eventually rubbed a few people the wrong way. And I was summarily fired from that job in 2018. Took another job that lasted about nine months kind of same issue. Being an intrapreneur in the insurance industry has not necessarily worked very well for me. I was fired from that job after nine months, at which point I said, maybe it’s the insurance industry. So I actually took the job. I took a job as a CEO of a fitness franchise, independently owned fitness franchise, they had six locations. I actually worked out there, it was local to where I’m from Albany, New York. And I was like, wow, this is really good. Like, I love fitness, I’d love to work out. I was like, I’m getting to kind of do do the leadership business stuff that I love that I’m good at that I’ve kind of shown a propensity for. And I get to do it in the fitness industry. You know, what could be better I’m wearing Lululemon every day is my instead of a suit and tie, I’m wearing Lululemon, like, it’s amazing, I get sweatpants on and part of my job is I have to work out at noon every day. Like, right, you know, I’m just terrible, surrounded by all these like, fit fun young people. So, so I thought I had hit the jackpot. And to a certain extent, I had, you know, I was in great shape, loving life. You know. And we grew from 2000 members to 3200 members and nine months summary for some reason, nine months is not a good number for me. We had two new locations opening, one had already opened, we’re crushing, at which point the founder decided the business was quote unquote, fun again. And that I was his largest expense. And he wanted to be CEO. So he fired me 8:36am On October the sixth of 2019, it was a Monday, I was sitting there waiting for our standard Monday meeting. And, you know, because we just kind of had, hey, what’s going on this week kind of thing. And I’m just, I don’t know, I’m thinking about all the things we have going on, we’re opening this location, I had a, I had a couple things like problems, I just had to solve that day that were small things, but whatever. And I’m just, I don’t know, I got a cup of coffee going. And he walks in and a suit and tie with his lawyer says, hey, you’ve done a tremendous job, thank you for your service, but we no longer need you. And I realized that that was the universe telling me or I hoped that that was the universe telling me that it was time to become an entrepreneur. So I kind of, you know, after, you know, a lot of cursing, and a heavy night of drinking. The next day, I woke up and I started working on Rogue risk, which was basically the derivative a derivative of all these conversations that I had had, I’ve done 375 keynote presentations, I’ve done countless workshops, I’ve spoke to 10s of 1000s of insurance professionals from every walk of this industry. And I had this concept of what I call the human optimized Insurance Agency. And I’ll wrap up the backstory here in a second. But I spent the next five months putting that together. And on March 9 of 2027 days before the zombie apocalypse hit on New York State. I launched rogue risk. And because of the zombie apocalypse, I did not sell my first policy till August. So I launched a brand new business that I put $50,000 into and didn’t sell a single item for the first five months and and now we do over an hour. We did over 5 million in sales. We’re growing like crazy. We have 25 people and you know, in three years, I think we’ve accomplished something pretty special. So that’s how we got to today.

george grombacher 9:40
I love it. I appreciate sharing the story. And are you grateful for all those experiences?

Speaker 2 9:48
Oh, shit. Yeah. I mean, look, I wouldn’t. At this point. You can’t, you know, I mean, I’m sure you could. I’m sure it’s possible, but like, I’m not scared of anything in business. So I’m not scared of tough conversations. I’m not scared of clients who have problems. I’m not scared of vendors. I’m not scared. I’m not scared of anybody. Because I’ve been literally knocked down 1234 times in a five year period. And then and then started my own thing and the universe, you know, you know, just said, Hey, yeah, we get that you’re trying to do this entrepreneur thing, but no, thank you. Right. And, you know, what I’ve learned is that I’ve just learned a lot about myself, I’ve learned a lot about leadership about perseverance, discipline, all these kinds of basic concepts. And, and ultimately, I’ve developed a core set of skills, and we’ll call them mental models, although I think that’s a very, I think it’s a cliche kind of bullshit term, but, you know, mental models for dealing with stuff. And now I just, it doesn’t bother me, whatever comes comes, we solve the problems, we move forward. And I don’t get down, I have tools to deal with it. I’ve developed a lifestyle that allows me to put my mental and physical well being in a place where no matter what happens, we’re able to figure it out and push forward.

george grombacher 11:13
Amen. So you, you did the opposite of me. I tried to never do math at all. And you’ve graduated with a math degree from college Australia. Talk about mental models talk about starting a business, going back into the insurance industry, and not selling a policy for five months. Yeah, did that. Did that shock the heck out of you? Were you terrified? Were you Oh,

Speaker 2 11:39
yeah, I kept I kept the Kentucky bourbon business, in business for that period of time. No, I mean, I made jokes. But you know, I think that if I hadn’t had all the experiences prior to that, if I had launched this business, and then that happened, I may have done the Woe is me. Why is this happening to me bullshit that so many people do. And then what happens is people do the woe is me stuff and they get some likes on Facebook for the wall with no, you’ll be fine. And then that becomes the thing, right? I honestly, I write a lot. And if anyone’s interested in how I think and how I operate, I have a blog that they’ll I’ll share with you at the end that I posted an article every Friday, but I wrote an article the other day, I don’t give a f what people think was the name of the article. And it kind of, it’s not like the most creative and I’m sure that some people will find it masturbatory but um, you know, the idea was, Aye. Aye, aye, honestly, don’t care what you think of me what anyone thinks of me. And I don’t mean that like, I don’t care I do. I want you to like me, I want your audience to find value. But you if you liking my posts, you like, you know, this, this trial, we’ll call them trivial. Trivial wins. I don’t value them at all right? To me, I have 20. I think I said 25. Before, I think today, we have 23 or 24 people, we did somebody, we just let someone go. But like, the 23 or 24 people that I have working for me, that’s who I work for the kid who just came in here and interrupted our interview. That’s who I’m working for my own my own desire to see how good I can be, which is what drives me every day. You know, my simple drive when I wake up before even my kids or the people that work for me is how good can I be? That’s what I want to know. That’s my life goal. My life goal is not to have a lake house, or Rolex, even though I do love watches and Rolexes are beautiful. I don’t desire any of that stuff. I don’t desire you know, I have, you know, like I said, I’ve done keynotes, I’ve had all these things I’ve had a lot of, you know, maybe not like international splash, but I’ve certainly had a tremendous amount of success and felt what that feels like in the, you know, had posts go viral on LinkedIn, and Instagram and all that kind of stuff, which is awesome. I mean, it feels good for a minute, but, but none of it means anything to me. It’s how good can I be? That’s what I want to know, How good can I be. And then from that comes an ability to take care of my kids to make sure that my my employees have paychecks and that they have a workplace which which they’re proud of and challenges them it gives them purpose and meaning. And like when I started realizing that it wasn’t about validation from an investor or a boss or some media company or a client or my spouse, I don’t need validation from anyone. I it is only about how good I can be. When I when I when that when that framework hit my brain when I started really believing that and not just saying right because because for a while I just said and I said oh how good can I be you know, whatever it felt like something fun to Say on an Instagram video or whatever, right? Like, when I started actually believing it. And I’m not sure when that was when I started actually believing it, maybe it was just getting fired by a holes enough times that you’re just like, Hey, I can’t, their validation can’t mean anything to me because they’ll they don’t care about me they care about themselves. When I started believing that, that’s when things really started to change when I was just like, I can get through this, because this challenge is a way for me to get better. This challenge is a way for me to get better. 18 months ago, out of the blue, I was on my way to one of my biggest business meetings of my life. My wife at the time called me and said, I’m not living my best life, I want you out of the house. Out of the blue, shocking. never cheated. No, Dad, I’m not an alcoholic, you know, pretty reasonable dad. On no idea. She just was unhappy. She basically was having a midlife crisis. And look, I want her to live her best life. But it was it was, it was like getting hit by one of those big balls on the end of the machines that knocked buildings down. It was like that I’m mentally prepared for this enormous business meeting. And that I’ve been preparing for for months. And on the drive, she decided that was the time to tell me that she wanted me out of the house. And it took my breath away. I didn’t. And it took me a minute and I pulled over the car. And and I mean, I’m not gonna say that I was perfect in that moment. But, but believing that these are just obstacles if anyone’s ever read Ryan Holiday, the obstacle is the way like, like, I just believe that that the all these things are put in front of us to make us better to challenge us. And even though I’m gonna say that I handled every moment of that situation and even posed perfectly. Because I don’t think that’s a proper expectation. I was able to sit there and go, this is a thing I have to get through. I could fall apart. Sure I could fall apart, I could fall apart people do all the time, I could fall apart and no one would second guess me everyone would be like we get it. You know, she’s this she’s that whatever, you know, or that, you know, the situation sucks, or what was you? I could absolutely I’ve done that and gotten all the likes on Facebook and all the sympathy cards and fallen apart and had a pure justification for that. I could have done that. Or I could have just stepped the fuck up and said this Sorry, I keep swearing. I don’t know if you can go and see it for what it was, was another test. It was a test. Can you be amazing? And have your crazy ex wife kick you out of the house an hour before the most important business meeting of your entire life? Can you do that? And so you know, I dominated that meeting and got a deal, right. I then afterwards, went to the closest pot store and got extremely high to pull myself back together just so you guys know, I want to be I’ll be honest about what happened. My mind was going 10 bazillion miles an hour. And I was still freaking the fuck out. But so I had to kind of smile, make my world little smaller for a little bit. I waited till I got home now while I was driving. But, you know, I saw you know, it’s not like everything’s perfect and all this you know, I want to be candid, but but the idea is, I think it’s very easy to fall apart and you’re gonna get people are gonna have sympathy for you if you do. And that’s fine. I just refuse to do that. And that’s how I get through things. And that’s how I keep pushing forward. And as I just said, Okay, this employee went bananas and started calling people crazy names and being a complete Jackass and, and that’s a really tough situation. It’s just another challenge. This client, this huge client decides that they’re going with another broker. It’s just another challenge, right? I can’t figure out how to get, you know, there’s leat, we got a leaky sales pipeline, and, and I’m really struggling with what’s happening. And I feel like I have blind spots and I can’t figure them out. It’s just another challenge, right? You know, it. You You have the option, you have the option. I mean, and that sounds so simple, but really, that’s what I tell myself all the time is okay. You can fall apart Ryan. Or you can just keep going and you can figure it out and what it’s allowed and you do that enough times that becomes the habit. That’s the thing is now I would never even consider falling apart the idea of it is in it’s it’s it’s something I wouldn’t even consider it’s not even an option that I would consider now it’s how do I turn this shitty situation into a 10x moment for me, how do I turn this into something that allows me to develop a skill or harden or strengthen in a way that I can go even farther? Right? What What can I use from this? Even though I’m, you know, maybe I mean, I used to cry. I mean, I lived in a hotel for four months, I cried myself to sleep every night, right every single night. But I use that as a moment, I wasn’t going to fall apart, you know what I mean? And that starts to become the habit, and then it’s not even an option that you consider, and then it doesn’t matter what comes in front of you. And look, I haven’t even experienced the worst things, right, my parents are still alive. My kids are very healthy. I have a tremendous set of friends. Like, there are worse things that could happen to me that have so I don’t want to act like my life has been this horrible thing. You know, I’ve had challenges, but I do think we have that choice. And if you can lock in and create that mentality and whatever version of words, you have to say to yourself to get yourself there. I think that’s incredibly important.

george grombacher 21:04
I think that’s really powerful stuff, man, asking yourself, How good can I be and answering that question, and then you just keep swimming, just keep swimming.

Speaker 2 21:14
That’s the deal. That’s, that’s it, like, you. Just everybody else is gonna give up. Everybody’s gonna give up. So I just don’t want to. But I mean, it’s, I wish I had better words, I wish I you know, I mean, I gotta come up with some cool catchy slogan for that, that I can like trademark or whatever, I don’t have it. I just, like, when bad things happen. I allow myself to feel them. i That’s not my I picked that up from a mentor of mine. He, when the actually when when the marriage thing happened, and it fell apart. He said, dude, allow yourself to feel this, let it let it he goes, if you got to freaking cry, or you got to yell or whatever it is that you got to do, like allow it to happen, allow it to flow through you. Because if you bottle it, you’re never going to get rid of it. So just let it let it go through you. So I that’s what I tried to do. I tried to let the thing happen. If it’s terrible, let yourself feel terrible. Somebody lies to you, somebody stabs you in the back somebody, some you know, someone gets sick, you know, all these things that you don’t want to have happen. You’re gonna feel something and let yourself feel. And that was his thought that was not my original thought he he said, Let yourself feel this thing, let it let it flow through you, and then be done with it. And then and then keep going forward. Because everyone else is gonna fall apart, they’re gonna give up, they’re gonna bottle it up, they’re not going to be willing to talk about it. And they’re going to, they’re going to play to the sympathy. I’m using social media references, right? Not everything’s a light, but like, they’re gonna play to the sympathy sympathy social media likes, that’s what they’re gonna go for, cuz that’s gonna feel good, it’s gonna make them feel like the fact that they’re eating shitty food and drinking all the time and not working out. And not reading and not studying the Bible and not doing these things that are productive, right? They’re gonna not do those things, and use that as an excuse. And if you can get through that and keep doing those things, you’re just gonna be a better person on the other side. So he was a Smart enough guy that I said, if he’s telling me to do this, it’s probably worthwhile. So I’ve kind of taken that and made it my own. And I still you know, what I do? I steal your watch. Mandalorian I love that this is the way you know me. And I think that’s fucking brilliant. And I will say that to myself all the time. Like, I’ll just I’ll just be like, this is the way this is what you have to do. Like I No, no, no, I’m completely ripping off the Mandalorian. I’m not trying to pretend again, like that’s an original thought. But I just loved that simple concept of like, there’s no other option. This suck. But it’s also the way forward, what are you gonna do? You could ditch about it, you could play and give up? Or just keep fucking going. And so I use I do, I literally will say it. Sometimes I’ll say it out loud. When I’m really struggling with something. I’ll just be like, this is the way alright, let’s go. You know, here we are. And then and then off you go.

george grombacher 24:18
So let’s go. I love it. Ryan, thank you so much for coming on. Where can people learn more about you? How can they engage? Who should? Who should be coming to rogue insurance?

Speaker 2 24:28
Yeah, so we are a national commercial insurance agency. We have people spread throughout the entire country. Our whole mission was really to take enterprise level service that is given to some of the largest, you know, think of fortune 500, fortune 5000 companies and bring that down to the middle and small market space. So we’re working with really any if you do 50 million in revenue or less, we probably have a solution for you. If you’re interested in that, or if you just want to check out the business and see if you know if any of this nonsense is actually what’s happening. You can go to rogue risks. That’s the name of the business, rogue risk.com. You can check us out, if you like this mental stuff. I have a blog. It’s free law essay, whatever wanna call it, it comes out every Friday. And you can find that at finding peak. So when I got like peak performance, finding peak performance, it’s finding peak.com. And the whole concept there is like, how do we deal with all the nonsense in our head so that we can actually become the best version of ourselves? And that comes out every Friday. So if you like, if you like that stuff, I encourage you to go to finding peak if you want to check me out, go to rogue risk, and then you can find me on all the socials. There are other Ryan handles, but they all hate me because I dominate the search results. It’s like It’s like Highlander. There can only be one. Like I literally had a guy. I literally had some Ryan Hanley from Scotland sent me an Instagram DM the other day. I effing hate you. I can’t, I can’t make it to the first page of Google. And I did a fist pump when I saw that I was

Unknown Speaker 26:03
Yeah, that’s right.

Ryan Hanley 26:07
Thanks so much, man. I appreciate it. This has been great.

george grombacher 26:09
It’s amazing. If you enjoyed as much as I did, surround your appreciation and share today’s show with a friend who also appreciates good ideas. If you are a small business owner, go to rogue risk.com and check out the great resources get better service save money and time. And then check out Ryan’s musings on all things peak performance and, and living our best lives at finding peak.com Find them on social media. Just type in Ryan Hanley and none of those other loser Ryan Hamleys will be popping up certainly not Sugaya, Greg. Sure. Sure. Thanks. Good. Thanks, but, and until next time, remember, do your part by doing your best

Transcribed by https://otter.ai

Thanks, as always for listening! If you got some value and enjoyed the show, please leave us a review wherever you listen and we’d be grateful if you’d subscribe as well.

You can learn more about us at LifeBlood.Live, Twitter, LinkedIn, Instagram, Pinterest, YouTube and Facebook.

Our Manifesto

We’re here to help others get better so they can live freely without regret
Believing we’ve each got one life, it’s better to live it well and the time to start is now If you’re someone who believes change begins with you, you’re one of us We’re working to inspire action, enable completion, knowing that, as Thoreau so perfectly put it “There are a thousand hacking at the branches of evil to one who is striking at the root.” Let us help you invest in yourself and bring it all together.

Feed your life-long learner by enrolling in one of our courses.

Invest in yourself and bring it all together by working with one of our coaches.

If you’d like to be a guest on the show, or you’d like to become a Certified LifeBlood Coach or Course provider, contact us at Contact@LifeBlood.Live.

Please note- The Money Savage podcast is now the LifeBlood Podcast. Curious why? Check out this episode and read this blog post!

We have numerous formats to welcome a diverse range of potential guests!

  • Be Well- for guests focused on overall wellness
  • Book Club-for authors
  • Brand-for guests focused on marketing
  • Complete-for guests focused on spirituality
  • Compete-for competitors, sports, gaming, betting, fantasy football
  • Create-for entrepreneurs
  • DeFi-for guests focused on crypto, blockchain and other emerging technologies
  • Engage-for guests focused on personal development/success and leadership
  • Express-for journalists/writers/bloggers
  • General-for guests focused on finance/money topics
  • Lifestyle-for guests focused on improving lifestyle
  • Maximize-for guests focused on the workplace
  • Numbers-for accounting and tax professionals
  • Nurture-for guests focused on parenting
  • REI-for guests focused on real estate

Feed your Life-Long Learner

Get what you need to get where you want to go

Rate it
Previous post