title: Transforming Frustrations into Opportunities in Healthcare
author: Founders Podcast
contenttype: podcast
publication: Founders Podcast
published: 2026-02-03T09:00:00
sourceurl: https://anchor.fm/s/10542bd40/podcast/play/113590911/https%3A%2F%2Fd3ctxlq1ktw2nl.cloudfront.net%2Fstaging%2F2026-0-6%2F415600819-44100-2-0b85aba82caf1.mp3
word_count: 5642
Hello, Donovan. How are you doing today? Excellent. Good to see you, Ash. Great, great to have you on Founders Podcast. Before we start on do you have a favorite course, Something that motivates you, inspires you, you would like to share with our audience? Sure. I mean, Charlie Munger has lots of great quotes and one of them, one of the ones I love is, you know, show me an incentive and I'll show you an outcome. And I think that's really instructive for the the industry. And the challenge is that my company solves for businesses. Show me incentive and then I'll show you the outcome. Impressive, deep, give you a food for thoughts. Nice, great stuff. So, gentlemen, let's imagine that we are in a room of full of ambitious founders, early stage builders, right? No one knows your name. No one knows. What do you do? You walk into the room, the spotlight is on you. You have the mic, everybody's looking at you. Who is this handsome guy walking on the stage? What he's going to tell us? What will you tell them so that they can stick with us for the next one hour? Sure, So what? What if your one of your company's greatest frustrations was actually one of your biggest opportunities? Greatest frustration becomes the greatest opportunity. Well, that is basically creating, I mean if that opportunity brings a lot of money or profit, then it's just creating money out of thin air, I guess. Exactly. OK. And how would you proceed further with it to explain one of the customers, clients or mentees you have helped out with which can explain the transformation? Sure. So we've had customers who, you know, businesses that have been been in existence for for decades and healthcare has always been a extremely frustrating topic is what was what was considered an uncontrollable expense, right? A runaway expense. Nobody can do anything about it. Healthcare costs just go up every year, you know, sign the renewal and say your prayers and hope for the best. What we did was we showed them a different path and a different way to finance and procure healthcare for their organization, resulting in not only much better plan for the employees, but unlocking millions of dollars in enterprise value when they exited several years later. And we've done that over and over again for our clients. Interesting, interesting. And I would love to know more about this strategy and how do you perform it. But before we get into that, I'm eager to learn more about you as a person. Can you take us back to your roots and share with our listeners about your upbringing, your childhood? How did your early experiences shape your journey and eventually LED you to become a visionary interpreter and potentially were there any key influences from your family or surrounding. You know the book we are, we have all read right, rich dad and poor dad. We always had this uncle or the friend's dad or or even, you know your own father who who has actually played a significant role in shaping your entrepreneurial spirit. Sure. So I, I grew up in upstate New York in the Catskill Mountains, which is essentially a, a great combination of hippies and rednecks living peacefully together in harmony. And so when I was I started playing drums professionally when I was 15 and I actually joined a a Grateful Dead cover band when I was 15, right after Jerry Garcia died in 1995. That opened up a whole new world of of existence and being and thinking to me at a very young age. But, you know, to answer your question regarding, you know, inspiring figures in my life, you, my dad, my dad taught veterinary science and primatology for 40 years at the State University of New York, where I lived. And so he had a very, very stable job. And there was a lot of beautiful things about that. You know, he never really made much money as a professor, but he had a lot of time. So in the summertime we would just, we would just get out of Dodge and go camping all summer and fishing and just doing amazing things and traveling all over the place. My dad is the oldest, is the oldest of seven, and some of his younger brothers were much more entrepreneurial. And so when we would meet up, you know, around Christmas time or what have you, you know, my brother and I were exposed to some very different kinds of, of existences and, and ways to live. And so, you know, being with my uncles who were entrepreneurial and seeing how they thought about challenges to unities risk and how to spend your time was just really eye opening to see this dichotomy of, of different ways to go about it. And I wouldn't say there is, you know, you got to decide what's, what's right for you. I mean, being being an entrepreneur sounds amazing in theory. In practice, it's much more difficult. So there's certainly virtues in in both of those past. At the end of the day, I think everyone's just got to decide what kind of life they want to live. Indeed, indeed. And when you stepped into your entrepreneurial journey, were you always an entrepreneur? Did you do any early, like initial jobs after your degree or what was going on there? And if you did jobs and then you moved, why? Yeah, I, I mean, I, I, I played drums professionally in Manhattan for 10 years after college. So I, I was, I was an entrepreneur, but not really someone who thought that way necessarily. I just kind of thought about myself as I do this thing and this is what I do. I didn't really have any kind of strategy around marketing myself, promoting my services. I mean, there was, there was so many, so many gaps in my, my business in my 20s in, in, in, in New York. So, yeah, it was, it was absolutely a struggle, even though I had some, you know, what people would consider masses success, successes. I mean, just just the fact that I was able to sustain myself for almost 10 years in Manhattan, playing music in itself is, you know, puts you, puts you in the, you know, .1% of, of people that call themselves musicians. But yeah, I didn't. At the end of the day, I was touring with a band that got signed the EMI and then right after we we recorded our debut album in in El Paso, TX, Sublime was recording one of their new records right next door to us. We got to hang out with the guys from Sublime, right? It was just an incredible experience. But then right after we recorded that album, EMI went bankrupt and we were done. And so I said, geez, you know, it's been a great run, but I'm 31 years old and I want, you know, stability. This is the height of the Great Depression or I'm sorry, recession rather in in the United States. And what's the I want the opposite life experience. So what's the opposite complete opposite of the music business? Well, it certainly sounds like the insurance business. And so I got it into it not knowing a darn thing about it. And it actually took me on some mistaken me some pretty interesting places which we can certainly discuss. Interesting. And was the was getting into insurance was your choice or was it just something and like an opportunity came to you and then you couldn't say no to it? Well, it's a great question. So I think, you know, one of the challenges that we inherently have living in America is that we we are swimming, especially as a young person, you're swimming in an ocean of opportunities, especially if you have any kind of skills or, you know, just the ability to think and solve problems. But, you know, frankly, at that time, I wasn't seeing a lot of angles in the marketplace. And I had very good family friends who owned an insurance agency for decades where I grew up seemed like a very stable, good pain profession. And frankly, the, the barrier to entry, for better or worse, is actually pretty low to get into the business. So between all these things and just thinking about the context of what I've been through in the previous ten years, you know, working as a musician and in New York City throughout, throughout the great housing bubble, etcetera, I was looking for stability. I, I was hungry for that. So, so yeah, the, in one sense, I, I guess you could say I was kind of forced into it. In another sense, it was, it was certainly a choice that I made after much deliberation and mental turmoil. It's a big transition. So how long it took you? So early, early 30s. A chap looking for more stability in his life found a job but with family connections, quite stable job and insurance. I'm guessing because you enter the industry fairly new, you might be starting from the, you know, base level. I guess, you know, cold calling for insurance or something like that. I don't. Know Oh yeah, no, you're you're absolutely right. And so the irony is that, you know, I was looking for stability, but the first job I got hired to in the insurance business with was with a company out of Chicago called Combined Insurance, which was started by the gentleman by the name of W Clement Stone, who used to wrote books with Napoleon Hill. And you know, the irony was that it was 100% commission's job. So you know, here I am with someone with basically no, no real sales experience, you know, cold calling businesses and brokers and, and selling, attempting to sell our insurance. And actually after a couple years I got really good at it and I was in the top 5%. I was one of our best, best producing agents nationally for for several years. You, you, you literally painted a picture in front of my eyes for, you know, the Wolf of Wall Street movie. It's like that, you know? Well, yeah, I mean, you know, there there are certainly ethical ways to sell anything and unethical, well, ways to sell anything. And, you know, W Clement, and this was one of the beautiful things about W Clement Stone was the culture that he built was just tremendous. In fact, Tim Ferriss was interviewing Jack Canfield on his podcast a few months ago. And Jack, one of Jack's mentors was W Clement Stone. He, he got hired by, by Stone when he was a young, young person and the beauty and, you know, Stone had created this whole methodology around how to live. It was just unbelievable. And that culture and one of the central themes of his, his methodology was, was what we call PMA, positive mental attitude. And it wasn't just a slogan on the wall. It was, you know, it, the whole culture, the building really just dripped of it. And so it really was, I was incredibly lucky to land there because as it, you know, as someone with no real sales experience or corporate experience, the I needed, I needed that, that positive environment to really, you know, keep me, keep me in the, keep my head in the game, right? I mean, I think that's one of the most challenging things about being an entrepreneur is, is keeping your head straight, right? Because and, you know, having the ability to get punched in the face over and over again and get up and smile and do it again. So, so it was it, I was just incredibly lucky to land in that place. I was incredibly lucky to have some mentors internally at the organization that really, you know, showed me and taught me the landscape of the insurance industry and how to do well on it and how to do well on it by by doing the right things for our clients. And, you know, you know, one, one of one of Stone's many sayings was do the right thing because it's the right thing to do. And so we, you know, we were very adamant about not overselling our customers, only getting them what they needed based on their risk tolerance, their their needs and their budget. So yeah, it just just a very, very positive experience and pretty transformational for someone coming from the music business. Indeed, Indeed. So let's talk about where your entrepreneurial story started. Did you lose the job? Did you resign? What was happening that time? And why did you move to to become a founder? So, yeah, so there's a couple of gaps I'll fill in here. So as I worked my way up through the organization, you know, a combined insurance got acquired by Chubb, which is as you know a multi national insurer and we got rebranded and and towards the tail end of my tenure at Chubb, I was actually managing our largest broker relationship. So just so everyone understands the distribution channel insurance companies develop and administer insurance products, but they're not very good at selling them. So they typically rely on brokers. We sell through brokers who sell them to employers. That's the distribution model that's been in place for, you know, about 100 years. And so I was managing our largest distribution partner. You know, this was a $30 million block of business that we were growing 18 to 20% a year. And I was actually developing the, the bonus programs for, for that client, for that broker, you know, literally flying them and their families on, on luxury vacations around the world when they hit their earnings targets, which they did. So, so, but at the same time, you know, I'd go to these open enrollment meetings and, and I, I, I'd listen to executives complain about rising health care costs. I'd listen to employees complaining about rising health care costs. And it's like, geez, why aren't these brokers at least recommending some of the strategies and solutions that a gentleman by the name of Harris Stone, who founded Rosen Hotels in 1974 in Orlando where I live, He he saved his company over a half a billion dollars by providing a superior health plan to his employees over the last 30 years. Why aren't these brokers at least recommending some of the strategies and solutions that that Harris Rosen had pioneered years ago? And I very naively thought, jeez, if I just moved to the broker's side of the business, I can probably scale some of these innovative solutions. I can probably help a lot of people and I can probably make some money doing that. And so I went and worked for a national brokerage firm and had some successes with clients, but I was ultimately terminated for quote being too hard on a health insurer who happened to pay this brokerage firm their largest bonus each year. And that's when the label went off for me is that the brokers and I should have known better given my previous experience, but the brokers at the end of the day, they work for the insurance companies, right? They are retail distribution for insurance companies. They are not in the business of helping employers maximize their healthcare investments. It's a different value proposition, a different role. And I said at that time, wow, I got fired for really advocating on behalf of our customers. And so if we're actually going to meet the demands of employers and patients and, and by the way, in the United States, employers cover about 50% of the population with healthcare benefits. That's about 164,000,000 Americans. If we're, we're going to help them solve these problems, we have to develop a revenue model so that we can, you know, financially sit on the same side of the table as the employer and protect them from the insurance and medical industrial and complex, not sell it to them. OK, So that's a very different value proposition. So I was inspired by the work of a gentleman named David Contorno, who had had built a fee based fiduciary based benefits consulting firm prior to me. So I said, you know what, this, this is the, this is the, the business I want to be and I want to be solving these problems for business, for employers, not selling them the problem. So that was really the, the, the, the origin story of, of Health Compass in 2018. So you you understood that if you go to the other side of the wall, there might be an opportunity sitting for you. And you also got into a pickle when you were working at the side of the world where you understood like primarily the agencies are actually employed by the insurers in a way that they are their biggest assets, right? When you understood it, what, what when you had this epiphany, did you looked into the market or you already had all these research with you? Were there other services or products in the market which was doing exactly what you wanted to do, but in a different manner? What was going on at that time, and what did you see from your research that encouraged you to move ahead with the idea? Yeah. So, so honestly, I, I, I didn't really recognize that I had trans transition from selling products for commissions to selling services for a fee. I didn't fully, you know, recognize that mentally. And it might have been because there was a lot of things going on in my personal life at the time that I was terminated. My wife and I, we had just bought our dream home and we're in the middle of completely gutting it ourselves and renovating it. And actually two weeks after I was fired, I broke my ankle severely working on the House. And then, you know, it gets better and then found out my wife was pregnant with our first child a few weeks after that. So it was a very tumultuous time. I was able to keep one client after my termination and I really started my business with that one client and now that I was free to do, to give them, you know what I thought was the best advice on how to manage their health plans and how to finance, procure healthcare for their employees. I ended up building them a bespoke solution to customize, you know, parts of all funded products, yada, yada, yada and save the company over $3000 per employee that following year with better coverage for the employees. And so and coincidentally another, that was another actually the first time we had this happen where our our customer was able to exit the following year at a multiple that they were very happy with. So we essentially created millions of dollars of enterprise value for that client. You know, by making a few simple changes. Very interesting, very interesting. So I think we have reached to a point where I can actually ask you don't tell me more about the product, the service, who is it for, what does what, what's the main problem you're helping to solve, who is your ICP, etcetera. OK, So just to level set for your audience, I mentioned that you know in the US employers cover 164,000,000 Americans with healthcare benefits. Here is the opportunity. 25% of what they spent last year was completely wasted. That's $325 billion or stated differently, $4000 per employee per year that should be sitting on bottom lines was completely wasted. And it, it comes back to a simple thing. Most finance teams and HR teams have no technical experience in healthcare financing or procurement. They don't know how to buy right. Just like I don't understand U.S. tax policy. And so I I hire an accountant right. I hire ACPA to watch my blind spots. The situation in health U.S. Healthcare is unique. Employers unknowingly ask the fox to guard their hen house. In this area. 81% of them work with brokers and without realizing that brokers are supply side vendors, they make more money when the employers costs go up, not down. So it's akin to you know, if my CPA was getting paid by the IRS behind my back, well I probably end up paying a lot more in taxes than I should. And that's exactly the situation that many employers are unknowingly in. And it's not necessarily their fault. It's not the, the, the broker's fault. This is the industry. This is how the industry evolved. And I actually detail this in my my book, which came out November 12th. So, so fiduciary based management consulting firms like Health Compass and there's a number of us in the market now, which is great. We serve as an antidote to the brokerage industry. The brokerage industry has been captured by a small number of insurance companies and pharmacy benefit managers for distribution purposes. And so at the end of the day, legacy brokers actually are financially penalized when they maximize the return on a business's healthcare investments. And so that's, that's a, you know, who wants, does anyone want to do more work for less money? Nobody wants to do that. And so asking these brokers to do that does not work. And, and we've, we've, you know, the, the proof is in the pudding. You know, healthcare has become a top three expense for most businesses in the United States. For many companies, it's the fastest growing financial risk on their PNL. And so it all comes back to you. You're not getting unbiased advice. And so you know, the, the, the healthcare transformation road map that I lay out in my book, the first step in that transformation is getting unbiased advice. Because if you don't get that, you'll never get to the second step. And again, we have decades of proof supporting that claim. Would you be able to take us through use case or a case study from one of your past customers or clients who have utilized your strategy in order to save a lot of money which you have already mentioned? What was the legalities around it? Because if somebody's listening our show and they are actually in this situation. So I would like you to explain first what kind of situation they were in, what were the legalities around it? And then how did you got them out of it so that they can not just save more money, but make it better for their employees? Yeah. So just a little context, you know, business leaders, anyone who has discretionary discretion over decisions that are being made regarding health and welfare plans is considered a fiduciary under U.S. Federal law, OK. That means that you can be held personally responsible if you do not uphold your fiduciary responsibility and make sure that you're not wasting your employees and your company's money. And as I just mentioned, most businesses are wasting a ton of money. So that's just some context. So I'll tell you a quick story that illustrates the power of getting unbiased advice. Couple years ago, we got a call from an executive director at a large teachers union here in Central Florida. And they said, listen, you know, we've got our some of our union members sitting on this insurance committee that meets every month. And they're smart people, but geez, they don't understand a lot of this insurance stuff. You know, they, they don't have any training in this and they're being asked to make decisions about this $65 million healthcare budget that is just spiraling out of control. Can you just come in and kind of show us what we should be pushing for in these committee meetings? They had been with the same broker for years. And so they hired the union, hired us outside of their broker and the union, you know, the union was, didn't really wasn't really sure if they should trust the district. They were, they weren't sure if they could trust what the district's broker was telling them. So they wanted an, an, a qualified second opinion. And so we came in, we did an analysis of their plans and their programs and we said, wow, your plan, you haven't gone to RFP for a new pharmacy benefit manager in seven years. Pharmacy just contacts. Pharmacy benefit managers are the entities that organizations rely on to manage their, their drug supply chain. You haven't gone to RFP for a new, for a new PBM in seven years. And by the way, you're with one of the worst ones. Why don't you push the district to go to RFP for a new pharmacy benefit manager? So they did that. They were successful and they got a new pharmacy benefit manager and that PBM saved them about $3.6 million last year while improving coverage for the employees, $3.6 million. This is something that their broker could have done seven years ago and and if they had done that, you know, the district would have north of $15 million more in their budget right now. But because they didn't, because of the misaligned incentives or whatever, the teachers and the taxpayers were suffering. And so this is low hanging fruit that frankly, municipalities all across the country are making similar mistakes. It's completely unnecessary. It's completely unsustainable. And and you know, this is really the why I wrote my book is that executives have the power to solve these problems, but only if they know how. And so that's why I wrote the book, to give them the executive playbook on that problem. Indeed, indeed. And I think I think that is very, very crucial because if the employers, the businessman, the founders, the executives understand how to make it more beneficial, saving money for themselves as an organization, as well as improving the lives of their executives or their employees, why not? It's a win, win situation. 100% again, Harris Rosen from Rosen Hotels saved his company over a half a billion dollars, OK by providing a superior health plan to his employees, so much so that his turnover rate that his hotels is a fraction of what his competitors is. Talk about compounding returns, right? When you consider the the cost of turnover, it's just unbelievable. So these opportunities are all over the place. It's at $300 billion a year. Opportunity hiding in plain sight. Indeed need Don, thank you so much for sharing this. Visit them. Can you tell our listeners again what what's the name of your book? Can you show it again please? Sure. So the, the name of the book is fixing Healthcare, how executives can save their people, their business and the economy. All right. And it's, it's actually been a, it was a best seller the week that we launched in multiple countries in multiple categories. And funny story, my uncle, one of my uncles was skeptical about the thesis of my book. And so he ran it through or he, I gave him the entire manuscript and he ran it through ChatGPT to get chat GBT's opinion on whether I was right or wrong. And it mostly agreed to, only criticism was that it didn't. My book doesn't address the things that employers have no control over, you know, regulation out of Washington, DC. That's not the scope of the book. People love having these thought experiment conversations around, you know, what if we started with a blank slate of paper, sheet of paper, and that's all fine. But you know what? I wrote the book to show executives how they can leverage the power that they have today, not hoping and wishing that, you know, some change happens in DC. Yeah, yeah, definitely, definitely great stuff. Well done. On at the end of our episode, we have this quick fire round where I've got 6 quick fire questions for you at any stage. If you want to not answer one of them, just give me a skip and then we can move to the next one. How's that sound? Great stuff. Number one, what are the top 3 strategies for executive make sure they have in their organization when they're looking for healthcare insurances for their employees in 2026? Yeah, so some easy things that you need to do 1 I already mentioned, get unbiased advice. You're never going as a leader in your organization. You're never gonna become an expert in this area. The like it's gonna take you 10 years of focused effort. The chances of you doing that are extremely low. So you need to know how to hire the right people to watch your blind sides, right? Number two, stop paying for healthcare that your employees don't actually use. Same. Simple, but it's amazing how many companies don't do that. Number three, stop overpaying for the healthcare that your employees do use. Healthcare prices in Orlando where I live are you over 1100%. Why buy Mris for $4000 when you can get them for $400.00? It doesn't make sense. Interesting. And that I think this concept could be applicable in a lot of other industries also, but I'm just holistically thinking about it. If it is applicable in insurance, there might be some other opportunities in other verticals too. But thanks for sharing that. What book other than yours would you recommend to our audience? And why? Wow. Well, one of my favorite books on healthcare that covers regulatory issues as well is David Gold Hill's book from 2013. That's for Off for Care. If you do want to go down that rabbit hole and, you know, really widen your aperture about the system, the systemic problems in general, Gold Hill's book is just masterful, just beautifully done. Great stuff. What 1 attribute or characteristic in your mind of a successful founder? I, I would say tenacity. If you don't, you know, if you are easily rattled by things, I would say your chances of success are extremely low. You have to be tenacious and just kicking down doors and getting things done, get it done, executing over just constantly. And this is something that, you know, I struggled with early on was, you know, increasing productivity. I think I'm a lot better than I was even just a few years ago, but if you really just focus, it's amazing how much you can get done. Indeed, indeed. What's your favorite personal productivity tool or habit? Productivity tool, I would say I love the Google suite honestly. I just love the way those tools interact and make make life so much easier. I know that's not the the most fashionable answer, but it's it's served me well. Indeed, indeed. What's a new or a crazy busy business idea you would love to pursue if you had time? Well, let's see, there are, there are several groups in the United States that basically they're called aggregators and they basically they're, they're a way for smaller brokerage firms to increase their, their purchasing power with vendors. And I would actually consider building one of those for fiduciary based management consulting firms. It doesn't exist today, but I think there's there's certainly a need in the marketplace for it so that we can solve, solve the challenges that, you know, American businesses and patients need us to solve at scale. It sounds very complicated to me because I am not from the insurance background, but I guess you know your stuff, so that must be a really good opportunity. What's an interesting or fun fact about you that most people don't know? Well, you know, I, I started playing music professionally at the age of, of, of 15. I, I, if you're watching TV in, in the early 2000s, you definitely heard me playing on commercials for Chevy, Nike, Motorola, HBO and others. And I actually ended up working with you too on an album as well. Awesome. That's great. That's great, Dano, and thank you so much for joining me and sharing your story and back in the years of building the product and service and and and and then your new book. If people want to check out your book, people want to get in touch with you if they have any question, what's the best way to do it? Sure. So you know, if you're an executive who's who's frustrated by rising healthcare costs, I would encourage you to go to fixinghealthcare.com, download the the free executive summary of my book. It's going to give you the six step road map for solving that problem. If you're an employee who's frustrated with with rising healthcare costs or stagnant wages, again, go to fixinghealthcare.com, download the free executive summary and give it to your boss. They have the power to solve a lot of these problems, but only if they know. How indeed, indeed. And thank you so much for joining us today and sharing your inspiring journey and the impactful work you're doing. It's been an absolute pleasure having you on Founders Podcast. Great seeing you Ash. Thanks for having me on.