In This Episode
In this episode, Rory Holland sits down with Bill Bloom, wealth architect and founder and CEO of Diane Money, to explore what it really takes to break free from the debt cycle — and why so few people ever do. Bill reflects on his path from Prudential financial advisor to building an app named after his mother, a woman who carried 45 credit cards and inspired a mission to eliminate a billion dollars of bad debt.
They discuss why the financial system is engineered to keep people in debt, how most of us inherit our money beliefs before we ever earn our first paycheck, and what it actually looks like to build a roadmap out of the cycle. Bill also gets candid about pouring over $200,000 into failed development attempts — and why he never quit. Beyond the app, Bill and Rory get refreshingly honest about their own financial struggles, the shame that keeps people silent, and why the most powerful financial tool available to anyone might just be a real conversation.
Key Takeaways
- The system is designed to keep you in debt. From student loans to credit card offers in college, Bill explains how the financial deck is stacked against most people — and why waking up to that reality is the first step toward freedom.
- You don’t know where your money goes until you look. A personal banker was unknowingly hemorrhaging thousands on clothes every month. Diane Money helped him save $3,000 in under two weeks — and he works in finance.
- The average Diane Money user saves $16,000+ in interest. By identifying hidden spending and building a debt payoff roadmap, the app does the math that most of us never learned how to do ourselves.
- Debt shame keeps people stuck. Bill and Rory get vulnerable about their own financial struggles — and why the single most powerful move you can make is an honest conversation with someone who gets it.
- Wealthy people are often the most miserable. Bill makes a provocative case that billionaires are driven by unresolved insecurity, and that no salary or title will ever fix what’s broken on the inside.
- Your money beliefs are inherited. The financial mindset you grew up with — scarcity, shame, or abundance — isn’t permanent, but it is powerful. Bill breaks down how to recognize and rewrite it.
- Gratitude has to come before generosity — not after. Bill’s challenge to give 10% even when you’re broke isn’t reckless; it’s about building the mindset that there’s enough, and that you can be trusted with more.
- Diane Money almost didn’t launch. Over $200,000 lost to failed developers, years of setbacks — Bill shares the raw story of nearly walking away from the app named after his mother.
- Letting go is a financial strategy. Bill argues that surrendering control — in business, money, and life — isn’t passive. It’s how doors open that force and hustle never could.
Transcript
Setting Money on Fire
Bill Bloom: It’s all about Diane Money. Here’s the story, and this was so frustrating because this was named after my mom, and the first developer that I hired, they completely screwed everything up. Nothing worked. Literally nothing works. So that was over probably $115,000 wasted. Gone. Poof. And he actually overcharged me because I had to go through everything and I got some money back, but still, it was literally money lit on fire. It’s getting your master’s degree without a diploma. And then my friend comes along and says, “You know what? I could do this. This will be easy.” Sure as heck wasn’t easy.
Introduction to Bill Bloom
Rory Holland: Hi, I’m Rory Holland, CEO of Customer and the host of Mighty Fintech Insights. Every year I talk with hundreds of financial leaders and innovators. We unpack the highs and the lows of working in financial services and fintech. Today I’ve invited Bill Bloom, a wealth architect who went from serving eight-figure clients to becoming the founder and CEO of Diane Money, an app dedicated to breaking the consumer debt cycle. In this conversation, we discuss how the system is rigged and the debt trap that we’re all susceptible to; the origin story of Diane Money and why Bill is so passionate about helping people retire as they desire; and how gratitude and surrender are essential qualities. Join me as we dive beneath the brand to learn what’s really happening.
Starting at the End: The Genesis of Diane Money
Rory Holland: All right, hey Bill, welcome to Mighty Fintech Insights. So good to have you on the show.
Bill Bloom: Oh, I’m so honored to be here today. Thank you, Rory.
Rory Holland: Yeah, man, you look good. Good lighting. I know you must have got some sun before you came out. I mean, it looks good.
Bill Bloom: Yeah, we were in Florida last week for spring break for a house we just bought. So, tax benefits, tax benefits. I did my hair for you today too.
Rory Holland: I see that. You styled it up. Yeah, it looks good. So, there’s so much I want to cover with you today. You’ve had such an interesting career, lots of different directions, the ups and downs of life that are part of all things that we have to go through as people, but also founders of companies. And where I wanted to start is your latest venture, then I want to go backwards. So, you named your newest company for a reason. I want to know why. Tell us where the name comes from, what was the ambition behind it, what inspired you to start the business?
Bill Bloom: So, it’s called Diane Money and the company is named after my mom who passed away back in 2021. And this is interesting because my parents were always terrible with money, terrible with credit cards. My mom had 45 of them. And I shredded them. I got rid of them. It was such a good energy clearing. But even though she was not great with money, I named it after her because that’s the forward legacy of her for our family. It’s to be the company that helps people get rid of a billion dollars worth of bad debt. That’s our big moonshot project, our big goal. And it’s starting to happen already.
And the ambition was just to help people get rid of bad debt, get a better understanding of where their money goes every month, because if you don’t know where you’re spending your money, it’s nearly impossible to make changes. You just need to have a roadmap and we’ve created that. It’s really simple to do. And this is truly coming from the heart. I mean, I spent years doing this. We’ve had major hiccups from a development stage and a monetary standpoint. It costs a small fortune to do this too. So I’m just excited to put this in people’s hands and let them have a better life.
Rory Holland: Yeah, I love that. It’s so challenging when we have friends or family members that have struggled financially and then that could lead to health struggles, a variety of other things. If you’re not living a balanced life, I’ve found—both with your health and wellness of course, but your financial health is a big part of that. And if you’re unhealthy in any way, that imbalance can cause a lot of challenges. And credit card debt is so pervasive in our society today. And when you think about that, your mom’s circumstance, there’s so many people in this country that are living paycheck to paycheck. I’ve got to imagine the market that you’re going after and the people you’re trying to serve and help is pretty massive.
Bill Bloom: Yeah, I mean there’s 1.5 plus trillion dollars of credit card debt just in the US alone. Just in the US. I mean, I can’t imagine worldwide. I’d love to take the technology worldwide and collaborate with other people. You just need a way to connect credit cards or the accounts that you’re using. So, I know Plaid doesn’t do that throughout the world, but the market’s huge. And we’ve been put into this situation from a debt perspective on purpose. I mean, the system’s been set up to make you fail. And I think people are waking up to that, Rory, to a lot of things in the world. But the system’s set up to have you in debt forever and trapped and stressed and not happy. And very few people take on the initiative to become an entrepreneur or not rely on a salary for their livelihood, and I think that’s a big mistake that people make.
Rory Holland: Yeah, so let’s go a little deeper on that. The system is set up for this. Tell me a little bit more about that.
Bill Bloom: Okay, so think about what you’re taught to do. You’re taught to get good grades to make you obedient, not think outside the box. You’re taught to go to college in order to have a good job and a good-paying salary. When you go to college, you go into debt, unless your parents had the wherewithal to save or have the ability to, let alone just the mindset to do that. So I had $54,000 in student loans coming out of college. If I were able to invest that money instead, I’d have a million dollars maybe, maybe more, just in that timeframe. So if you go into debt right out of college, you’re in trouble. Then you have to get a car, and then an apartment, and then credit cards, right? You’re bombarded with credit card offers when you go to college. So that in and of itself, you’re trained to be in debt. And it’s not the good kind of debt. It’s not you’re buying investment properties that you’re having other people pay off the debt for you. You have to do it. So the system is set up for you to be in debt in and of itself. And I think if you, unless you want to become a lawyer, doctor, dentist, right, something that requires you to go to school, you’re better off using those four years to invest and start working and make money or try something versus being in debt.
How Diane Money Is Helping Break the Debt Cycle
Rory Holland: Yeah, as we move, as society changes, culture changes, I relate to everything you just said. So, I came out of college, got a credit card, didn’t understand it, ran it up. I’m “Cool, I have 500 bucks, I’m going to go spend it,” bought a set of golf clubs. I’m “Oh wait, shoot, I got to pay that off now.” Well, with interest. And I still didn’t learn early, because you’re right, then the cycle starts to turn and it speeds up. You get out, you get an apartment, you get a car, then you get married, then you need a house, then you need a bigger house, and then you’ve got home equity lines to do things that you want to do to your house if you don’t have the cash. I’ve seen friends and myself, I’ve been through it before. And it’s a never-ending cycle if you don’t get off the wheel. You’ve got to get off the spinning wheel at some point. And so I want to talk with you a little bit about that and how is Diane Money helping people open their eyes to this as people start to discover for themselves that the system is a bit rigged? How’s it work?
Bill Bloom: So the biggest insights that we’ve seen with our user base so far is, number one, their monthly spending. So when you sign up for Diane Money, you’re going to get a snapshot every single month of where your money is going. And then you get three new ideas on how to save money for money that’s literally just hiding in plain sight from your spending. So our technology showed a personal banker—this is a real story—that he was spending a fortune on new clothes every month because he thought he had to look really good at the office in front of his clients. But he saved over $3,000 in less than two months just because Diane showed him—an actual banker, you’d think bankers are good with their money, they’re not. He saved three grand. It’s insane.
And then on the other side of things, when you look at the debt, we show you all of your debt, all your interest rates. So if you see you have a 29%, a 24%, and a 16% interest on your credit cards, it’s going to behoove you to take care of that 29% first, then the 24%, then the 16%. So we give you a roadmap on which debts to pay off first, and most people don’t even know how to do that. And the way that I created this technology is how I paid off my student loans in less than three years. I had 8.5, 8, 7.5, you name it, down to 4.5. And I didn’t understand any of this until I opened up all my statements, put them on the table and said, “Oh my God, I’m paying this much interest? This is crazy.” And I was able to pay these off on a $76k, $78k, and a $98,000 salary in three years. So I wasn’t making millions of dollars at that time. I just focused. And the technology does the work for you to show this to you. And I want to add one more point. On average, our users are saving $16,000 plus dollars on interest by using that money that Diane finds for you and implementing that toward your credit card debt. It’s huge. So an extra $16,000, imagine what you could do with that. That’s retirement, that’s vacations, that’s down payment on a property, whatever the case may be.
Bill’s Journey into Finance and Helping People
Rory Holland: Yeah, I’d like to keep going down this path, but I want to back up a little bit for the listeners and what were you doing—what led you into this space? As you were at a financial college, what got you into finance and then you became an advisor? You’re a multi-time author, so you’re an author of many books. You’ve done a lot of things. But where did it start? How did you get out of college, get a job, decide to get into the financial space? Tell me about that.
Bill Bloom: Yeah, when I graduated college was the year 2008. Best year in the world to graduate.
Rory Holland: That was a great year to come out into the job market.
Bill Bloom: A lot of job opportunities. My intuition was saying, go to London. I went to London and Paris for a college trip. I wanted to go work in finance in London, I just loved the city. It was just one of those things where the energy spoke to you. I’m really big into traveling. But it was not happening. The whole world was on fire, financially speaking. So I was interviewing with a bunch of different financial companies and what got me going down this path was the gentleman who taught our finance class in university was a financial advisor. And he showed up one day in a big Cadillac Escalade. I’m “Wow, cool. He must have some money.” And we went to school in a really small town in West Virginia, so it wasn’t normal to see something like that. And I thought, “If this guy could do it, I could do it. I could figure this out.” That was my mindset because I was not a genius and I’m not either. Don’t get me wrong, I’m not some brainiac kind of person, but I was “You know what? I think I can figure this out.” So I just went for it and I applied to a bunch of different places. The same day I got my rejection letter from Edward Jones was the same day I had my acceptance phone call from Prudential. So I thought, you know what, this is a sign, let’s go for it.
And I spent six and a half years there. And it was the best thing I could have done because the gentleman in the office who had been working there for 30, 40 years, literally, one day I said to them, “Can I go have lunch with you guys?” I just wanted to learn and just be a fly on the wall. It was the smartest thing I did because I learned what not to do along with what to do and how to truly help people, because these guys have had experience forever. And I knew I outgrew that place when your managers were asking you, “Can you share this case with this other person so that they could stay on?” or “Could you write this case so that the manager could get the bonus?” I’m “I can’t be in this environment anymore.” It just wasn’t fitting for me. So I left at 28 and said I’ll figure this out myself.
Rory Holland: I love that. Similar in ways, I got into the workforce in the early ’90s, not a great time—’92—to come into the workspace. I decided early on too that it wasn’t for me. I wanted to be my own boss, I wanted to build, I wanted to create. And you said something that I really connect with is, “I want to help people.” We enter the workspace for different reasons and we live our lives for different reasons. Everybody does. But the ultimate desire, it sounds for you, is to help people. Otherwise, you wouldn’t have pursued this path. So I’m curious what happened after Prudential that then led into the work that you’re doing now? Tell me what was the next stage and where was your heart at that point, based on what you had learned from being at another company that you didn’t want to be—in an environment you didn’t want to be in?
Bill Bloom: Yeah, it was more survival at that time. It was 2014, I was 28, started my company. I mean, my first year I think my net income was $24,000. It was really difficult. I lost all my clients for nine months in two years. I was starting from scratch. But you know what? I paid off my student loans. I always thought I could just go live with my parents again. We’ll figure it out if this doesn’t work. Intuitively, I didn’t realize how much my heart was involved to do this. I always thought money, money, money, figure it out, make money. But there’s so much more to that. There was one time my wife and I, we went to one of my clients’ wedding, or his daughter’s wedding. It was actually in this building right down the street from here where I’m recording right now. I was the first person that he thanked during his speech.
Rory’s Commentary
Rory Holland: If you see Bill as just a wealth manager, this story doesn’t look good for the father of the bride. But if you understand the power of what Bill is doing for his clients, it makes perfect sense. Money is the means to an end. It’s how you provide for your family and create the security to pursue your dreams or the love of your life. When our relationship with money is controlled by greed or scarcity, it destroys us. When it’s grounded in gratitude and generosity, it has the power to change lives in a big way.
Bill’s Journey into Finance and Helping People, Continued
Bill Bloom: I looked at my wife—she was pregnant with our second son at that time—I’m “What is going on right now?” Ron was speaking our praises, the first thing during his daughter’s wedding speech. I mean, that’s the importance that you have in people’s lives. My mind was blown. I couldn’t believe it. And that’s when you know you’re on the right path. It’s all about relationships, it’s all about taking care of your people and just listening. That’s the main thing. For what I do, people just want someone to talk to and guide them, hold their hand. Those are the people who we work with in the best fashion. And the same is true for Diane Money. We’re starting to hold once a month on Fridays just open discussions about debt. Just come talk to me. It’s free, there’s no cost. Just come have an open mind and let’s see what we can do. Let’s talk about this. There’s no shame in having debt. Let’s just figure this out together as a group and have a better life. That’s what this is all about at this point in my life.
Overcoming the Shame and Guilt of Debt
Rory Holland: Man, you said the word “shame,” and I think there’s enough shame and guilt in this world, I don’t think men or women, people, need any more. That’s for sure.
Bill Bloom: Amen to that.
Rory Holland: And you made me think about a friend of mine a couple years ago. I was deep in coming to the end of my son’s motocross career. And we had accumulated a tremendous amount of debt. So I put most of everything I ever made into CSTMR agency and grew that over the years, but I was just basically pulling out everything I could to help him fulfill his dreams. And I really to be honest, I wasn’t—I was acting more emotionally out of heart to support him than thinking logically or strategically about what is the rest of my life and my wife and I’s life and my daughter’s life, our family’s life going to look like financially? So I was in a pretty tough spot and a lot of shame and guilt about the decisions I had made because I was in the system. He needed more bikes, he needed more training, we needed to travel more, we needed to race more, all of those sorts of things. It was just on the hamster wheel, so to speak.
And I sat down with a friend of mine that I thought had it all together. And this goes to the shame part. He belonged to a beautiful country club here in Austin, Texas, and owns a couple of companies. He’s the kind of guy that walks in a room just full of energy, he’s got it all together. And he confessed to me that he was almost bankrupt. That the load of his financial activities, his home, his country club, his wife’s things, his kids’ things, kids in college, he’s “I’m more than broke, I’m in so much debt. I don’t think I’m going to make it. I’m month-to-month at this point and I’ve got to start shutting stuff down.” And it was so helpful to me. It’s almost like you talk about these weekly working sessions. For someone you can just talk to. And I think it gave me room because he was being vulnerable and honest to say, “Hey man, let me tell you my story,” right?
And so together we bonded that day. And I’m happy to say that both of us, one, I’ve paid off all—I’ve worked really hard, so I’m confessing stuff on this show, but I’ve struggled with money too and choices, poor choices, some good. I would do anything for my kids and my family, but that’s the tough role we play as fathers and entrepreneurs. We have to make good decisions to support our businesses and our teams and our clients, but also our families. And I’m happy to report that I was able to pay off my debt and I’m also happy to report my friend, we’ve become really good friends, he has completely turned it around. And so now he’s on the upward trajectory and so are we, so is my family. But we walked it together, which was incredible, brought so much power and it allowed me to remove the shame and guilt knowing that someone I thought that had it all together—and then I found out a bunch of my other friends were struggling too. So we almost created a mini group where we get together and have coffee and “how are you handling this?” With your wife or your kids? One kid got into Dartmouth and he’s “I don’t have the finances, but I don’t want to hold my kid back.” I’m “Well just take a pause. Don’t let society tell you what your child needs to do. Maybe that’s not the right decision.” And they ended up making the right decision for them. But if it weren’t for conversation, what you’re saying and you’re exposing it for what it is, those folks couldn’t get help. So I wanted to hear a little bit more. You’ve now opened—it sounds like you have these weekly or monthly get-togethers where you just open your time, I’m here to talk. Is that right?
Bill Bloom: 100%. We’re doing it once a month because I’m realizing people are—they’re scared. It’s hard to make changes. You went through it, your friend went through it, I’ve gone through it. To be absolutely vulnerable, to build Diane Money, I’ve had over $100,000 of credit card debt to build it on the first end, the first iteration, because I didn’t have it at the time. But I thought, you know what, I’ll do it, I’ll figure it out. And we have. But we’ve had a lot of obstacles during that time. But I want to have a safe place for people to just come, ask questions, because what I do for them is I pull up Diane Money, I put them in their situation and show them. So that way they have a framework and other people can see it in action and then they can go do it themselves. I’m just teaching them how to make things better because inevitably you can’t hold everyone’s hand forever. You have to make a decision, you have to act. You can pray all you want, but if you don’t change your mindset or your energy around it, it’s really hard to make those changes.
Rory Holland: I want to ask you about that. Knowing people and money so well, you’ve made this your career, what are some of the types of relationships people have with money?
Bill Bloom: Ooh, how much time do we have? There’s scarcity, there’s abundance, there’s people who don’t care about it, there’s people who think that it’s the cause of all the problems. There’s an amalgamation of energy around your money and where you’re at in your life. You’re only at where you’re at because of your energy and your mindset around money. And you get that from your aunts and uncles, your parents, your grandparents. It’s set early, but you don’t have to believe it. You don’t have to choose to. If you choose that money’s scarce, you’re completely wrong. They print money every year. Money’s made up. It is completely made up. They print money. So there’s an abundance of it. So there’s a plethora of thoughts around money, but it truly comes down to your heart and your education around it. And there really is none. So you get that from your family and they’re not educated on it. So it’s the worst form of education.
Changing the Energy You Have with Money
Rory Holland: Yeah, I think in my circumstance, my kids have learned through my mistakes because I have chosen to be vulnerable with them. Because of the decisions I’ve made in the last decade, particularly with my son, my daughter was competitive with horses, if you look over my shoulders you can see both of them doing their thing. So my wife and I poured into our kids and I wouldn’t take it back. But when time came for them to choose career paths and my son’s 19, my daughter’s 21, both of them chose—didn’t choose college. They’re “I don’t get it, there’s a lot of things I might want to do, but I don’t know what I want to do and it seems silly to spend that much money every year. I would much rather invest that money, start my own thing, learn all that.” Which I’m really grateful for. But it caused me to have to open the books and say, “Kids, I don’t want you to make the same mistakes I made and my parents made,” because they’re right, I feel it’s generational. You grow up with an environment that has a perspective and there’s almost an energy around money that can be positive or negative. But it hangs with you and I had to break a tie. I asked you that question for a variety of reasons and I wanted the audience to hear your thoughts and I think you’re totally right. I had a business coach right before I started this agency that I hired that called it out on me. He’s “You have a weird relationship with money. Let me tell you what I think.” And he nailed it. And it was because of scarcity growing up that I had always held tight and felt there was never enough. And so I was living in this place of fear and scarcity as opposed to abundance. And so the energy was just wrong. So even when I was making a lot of money, I still wasn’t there and I was still seeking other things. I mentioned my buddy that I sat down with a year or two ago and just struggling, both of us struggling but not knowing it. I think that’s the biggest thing is you see neighbors, you see friends at events or you go out to dinner as a family or couples, and you know they’re throwing down their Amex black or whatever they’re doing, right? And then you scratch the surface a little bit and the door gets cracked open and then the floodgates open. And it’s okay, you know I’ve learned that with so many people. And some of the most wealthy men I know are the most depressed and stressed. They’re just in this pursuit of more and it’s never enough. And it’s my goodness, what is that?
Bill Bloom: I can tell you what that is. I know exactly what it is. Yeah. I mean, the reason why people are stressed and depressed is it comes back to their childhood. They haven’t taken care of their childhood traumas and their issues or their family issues. It’s all coming down to an insecurity somewhere. When you look at billionaires, they are the most insecure people on the planet. And they think that habitually when they’re continuously winning or when you become the CEO of a massive company, it’s all ego. They haven’t killed off the ego. And that leads to the same behavior and they think that the next level that they get to is going to make them happy. It goes back to what we talked about earlier. And that thing is not going to make you happy. Getting that title is not going to make you happy. And if you’re not happy presently, none of that stuff is going to matter, Rory. And the more you earn, the more you make, the worse it gets because you’re just building that mountain of garbage. I would use a different word if we weren’t on the show but you’re climbing up a pile of you-know-what and it stinks being on it. And you don’t even know you’re doing it to yourself because you’re trying to impress your spouse, your family, the people around you and they really don’t care about you. They truthfully don’t care. I mean, there’s maybe three or four people in your life that really truly care about you. Most people want to see you fail. It’s the opposite. And when you’re pushing up that hill and climbing over the backs of other people, they don’t want to see you succeed. They could care less about you and that’s bringing even more bad energy towards you. So that depression, that guilt, that stress is all ego. And you have to kill the ego.
Rory Holland: Yeah, I think that speaks very loudly to those who have had a lot of success but aren’t finding fulfillment. And no matter what you achieve, no matter how much you accumulate, if you’re not happy at the core, nothing else is going to make you happy. And then just the weight of all that, being the CEO—there’s so many tired CEOs out there. I think they’re just tired. Because when do you put it down? I heard a guy on another podcast who was the Google Business Executive, so he basically ran Google Business, getting them global. And he was telling his story of “I had made more money than I—I had more zeros in my bank account than I could ever spend in multiple lifetimes.” And he said, “I was depressed and suicidal.” And he said what made me more depressed and suicidal is I could buy and do anything I wanted and it didn’t work, it didn’t help, and that was the only lever I knew how to pull. So when I pulled it and it made it worse, it was a downfall. So he said finally, I’m out, and I’m not going to do this anymore. And he did the opposite. He started to get rid of everything. So he simplified his life and reframed everything and turned his life around in a life of service for others versus service for self. It was a pretty powerful story for a guy at that level to determine that and make that—in that case—a dramatic life decision to get rid of the multiple sports cars, the homes all over the world. “I don’t need all this, I’m going to just help people, I’m going to get rid of all this stuff.” And it changed his life, and fulfillment and joy and peace came. And it was really neat to hear him tell that story. And I think that’s what we can do in very micro levels too. You don’t have to be a billionaire to do that. You could do that on a $60,000 a year salary too.
Bill Bloom: 10%. Help someone with your money. I mean that’s one of my life goals, every month – and it’s not perfect, I’m not saying I do this every single month. But if you try and do 10% to help people, when opportunities come up, do it! Go and help that person. Do the thing. Donate to the charity. Even if you’re short on cash. Do it. That’s the mindset. That’s the letting go. That’s trusting the universe. Trusting that more will come to you because you can be trusted with your money.
Rory’s Commentary
Rory Holland: Ah, I love this principle. To the person who can be trusted with a little, more will be given. You don’t have to be a person of faith to operate this way. And I can’t say this strongly enough. True generosity doesn’t have a number attached to it. Even if you can only afford to give a dollar to someone in need, if you give it with a grateful heart, the positive ripples become a tsunami. Wealth doesn’t precede generosity, gratitude does.
Changing the Energy You Have with Money, Continued
Bill Bloom: Knowing that more will come, it’s meant to be used. You’re not going to die with it. Go and enjoy. And what that gentleman did, I love that. I’ve had those moments in my life too of getting rid of a ton of my watches and getting rid of all the stuff I don’t need. Tom’s laughing at me here in the studio because we love talking about watches, but there’s some truth to that. There really, really is. You hit that focal breaking point where it’s either I’m breaking or the stuff that’s breaking me needs to go, and you need to make that choice because it’s too much energy and it’s happening here and not in here.
Living with a Small Circle of Trusted Friends
Rory Holland: Yeah, I love it. Last thing I was just going to ask your thoughts on is, someone asked me a really great question and he had a bit of a philosophy about a Venn diagram almost of relationships in your life. And he was saying to every man I ask and they have a hard time telling me who their closest friends are. Who would you trust your family with? Who would you trust your finances with? Who in your network—who is your closest friend? Well, how many do you have? He would say most guys would say, “I don’t know, two or three.” Well, name them.
Bill Bloom: I really have maybe two. I mean, I have outgrown the majority of my friends just from a mindset standpoint or a philosophy standpoint or what your heart represents versus your mind, or just it’s hard having conversations with people when they’re so stuck on a Republican or Democrat or this or that. It’s all nonsense. And you outgrow people and you have to outgrow people. You have to let people go. You can’t keep those same friends forever because you’re meant to meet new people. We met each other, right? This was meant to be. You have to let that go. And it’s okay to only have one or two friends. It’s okay to have maybe a handful. You don’t need a million. Less is more actually in my opinion. I really believe that. I have one super close friend and we talk on the phone maybe three to four, five times a week. Another guy, a very close friend of mine. But that’s really it. I mean that’s really it. It’s very hard for me to have other conversations with people at a very deep level sometimes just because we’re not on the same page. And I know that on the onset, so I don’t even waste my time or my energy. But I’ll give some insight, and if they take it great, if not no big deal. It’s hard. It’s really hard. I definitely struggle with that part.
Rory Holland: Yeah, something we can definitely talk about. Community and I think fellowship is tough for leaders of companies because we’re all running and gunning so hard and if you’ve got a family you’ve got children, there’s just not a lot of time. But if you don’t make the time, you want to have people in your corner. My point is that you can trust to be vulnerable with, share the ups and the downs and walk life with. That’s why I mentioned that is I’m the same way. There’s a handful of guys that I really trust, but they’re newer to me. My oldest friends we, you know I still have some, but we’ve all gone different directions. And I’m in a little bit different place in my life than maybe some of them. Nothing wrong with that. But having people we can rely on and why I’m so grateful that you’re doing what you’re doing with Diane Money, being willing to open your calendar to have time to have real conversations with people that are really struggling. It’s equally financial advice as well as in strategy as it is therapy.
Bill Bloom: Oh, it really is and I love doing that. And it really just makes my heart happy. Because if someone takes one takeaway and they change their life and I never talk to them again, God bless. I’m so happy about that. It’s not about the monetary thing, it’s about making that impact on people right now. If someone could pay two dollars a month to literally cover the cost of what the tech costs me, let’s do it. I’m so happy with that because I know we’re making that strategic impact and good things happen on the back end of that and I’m not worried about it. And that’s the art of letting go. Just let it go. See what happens. Then miracles happen. It’s so fun that way.
The Method to Retire as You Desire
Rory Holland: And I wonder what your thoughts are when you think about trying to help people retire—one of your taglines, I think your core philosophy: retire as you desire, right? Boy, that would be great. But people I think seek comfort in everything. Maybe they’re overspending and seeking comfort. If I have that car, if I build that pool, if I buy that house, if I go on that vacation, if my kids go to this school, whatever it is, you and I both know no matter what you achieve depending on where your posture is and where your heart’s at, it won’t fulfill you. So I’m kind of curious what you think about people seeking comfort and I’ll figure out what that quote was because it’s really powerful. I’d love to hear your thoughts on it. But first, thoughts on that.
Bill Bloom: Yeah, the thoughts: you need to be happy now. If you’re not happy now, you’re not going to be happy when you get the thing or do the thing or experience it because you have the wrong mindset, you have a really negative energy around you. You can’t wait. The trick is: when you’re happy now, even if you pretend you have the thing or you pretend you’re doing a thing or you pretend you’re making the money, that’s the gateway to open the doors for it to actually happen. You have to be there now, be present now for it to happen. It’s a very spiritual thing, it’s a very heart, enlightenment thing. But if you’re always waiting, you’ll never have it. You’ll always be chasing and that’s the worst place to be in life is just chasing the thing. You’re going to end up on your deathbed and be “Man, I wasted my life.”
Becoming Comfortable with Discomfort
Rory Holland: Yeah 100%. And I think we have to learn how to—and it’s something I practice every day—be happy and comfortable in whatever my circumstance. Learn to be content in no matter your circumstance. But that’s a spiritual thing, that’s a faith thing, that’s a biblical thing. But actually practicing it is totally different. Okay, so I found the quote and it was just in January that Matthew McConaughey was on a Bit of Optimism with Simon Sinek and he said his philosophy, McConaughey’s that is, centers around getting comfortable today with what I was uncomfortable with yesterday, rather than changing what I was uncomfortable with yesterday. So getting comfortable with what I was uncomfortable with, rather than trying to change it. Trying to change your circumstance, just get comfortable, be content. That’s how I took it. And I’m kind of curious as you feel you’re equal parts financial advisor, therapist. Is that accurate?
Bill Bloom: Always. Every day. Yeah. 100%. Because here’s a perfect example. I just had to fire a client. They had a $600,000 account with us. They run probably a 40-50 million dollar a year business. And when the markets are going down, if you keep adding money to your account, your account goes down faster. That’s the reality. It’s math. It’s you keep adding every month and when the market’s falling, your money falls faster. You’re just you keep buying and you’re losing, you’re buying and you’re losing. So in December—I mean we’re in April now—in December sold half their assets, put in the money market, simple. Then right as this turbulence started in the world, we sold everything on that Monday and the markets were up that day. So it was good. But with the markets being down 10% roughly right now, they saved over $60,000 from that standpoint. But they’re still thinking, “Why is my account now not up because I was putting in a couple thousand bucks every month?” Well, because when you invest in the market’s falling, you’re going to fall and we mitigated a lot of that. We got ahead of it. Still unhappy. I’m this isn’t a good fit. Yeah, so the mindset is just that scarcity is just you have to have patience. People forget about patience. You look at your Instagram, your social media, you think you should have it now. Life doesn’t work that. If you just feel you have everything and you’re happy now, you’re not going to be happy all day, nobody is. And if they tell you that, they’re lying, it’s impossible. And the attitude of gratitude thing—I’m all about that. But inevitably you have to get some fire in your belly to go out and make a change and do something different. Because that attitude of gratitude all day long will keep you in no-man’s-land. You won’t do anything. You have to act. So what McConaughey said, you have to be uncomfortable and just get used to it and deal with it. That’s the best part of life. It’s I feel uncomfortable posting all the time about Diane Money, because I don’t know what I’m saying. I don’t know what I’m doing. Be the first person to admit that. I’m not a marketer. But I’m working on that messaging just to connect with people from a heart level. You know, get out of the mind, get into the heart and say, “This is what we can do for you. We can help you.” And it’s uncomfortable doing that. Building this was uncomfortable and just launching this was uncomfortable. But we’re at a point where people are using it and you’re seeing results. So it’s really cool. It’s really, really fun.
Rory Holland: Yeah. That’s awesome. I mean, I’ve looked at the app, I think it’s wonderful the work that you’re doing. And I wanted to back up a little bit and just thinking about financial literacy in this country and people are arriving at these challenges fast in their lives. I could see it in my kids’ choices if I wasn’t working with them, and if I hadn’t shared everything with them, they would be doing things much different. But they save 50% of everything they make. So I’m you, you’re home right now. Both my kids are actually home. So I’m “just save it.” And I want you to diversify your savings. Here’s why it matters. Your dad didn’t do this growing up. I want you to do it. And it’s been remarkable, actually. But so many of their friends have bought cars, rented houses that they shouldn’t or fancy apartments or going on vacation they shouldn’t do. So I’m kind of curious what you think about financial literacy in this country and the lack of it?
Bill Bloom: Yeah, I mean it’s on purpose. We all know this, right? I’m not saying anything new. This isn’t something that’s profound. We’re not educated about money because they want us in debt and just feed the system and pay your taxes. And keep it going because they’re the ones who are making money on our debt. The truth is that it’s on you and it’s not on anyone else. Because your parents could teach you this, they could not teach you this. I’m a perfect example, my parents didn’t teach me but I figured it out. Anyone can. Anybody can. But it’s on you and you have to take that onus to put it on yourself. It’s your responsibility, it’s not your parents’, it’s not your siblings’, it’s not anyone else, it’s not your spouse’s. It’s on you. And when you own it, you can figure it out. Things can happen. Embrace the struggle, because there will be months where you may do everything right and your car goes out, something happens you need a new roof. It’s “uh oh, gotta figure this out.” It’s happening to you on purpose to expand your knowledge base and your capacity to figure things out. None of it’s random. None of it’s random. But you have to embrace it and take responsibility. That’s what my thought is.
Rory Holland: No, I love that thought. So true. I think we grow in the valleys, not in the peaks. Right. And I think moving through circumstances, what I was saying about what McConaughey said that struck me so much is I think often we seek to move out of uncomfortable situations fast versus moving through them, because the through part can be really hard.
Bill Bloom: Oh yeah, yeah. But I think if you set a framework of “Is this going to impact my life 10 years from now or 5 years from now?” And if it’s not, make a decision and move forward. Don’t spend a week on it. Don’t spend a month on it. Spend five minutes, make the decision. Execute and move forward because then you’re not wasting that mental energy on your life. Just make the decision and go.
Rory’s Commentary
Rory Holland: Don’t overthink it. As someone who has made mistakes and tried to plan for the future, I know how easy it is to get stuck. Bill isn’t encouraging you to be casual or impulsive. As long as you know your values and your “why” for a given decision, you can move forward in faith. Even the best plans are subject to change. The question you should ask is: can I take the next step and trust the doors will open?
The Difficulty of Increasing Financial Literacy, Continued
Bill Bloom: And then you’ll figure out if you’re right or wrong and that feedback will be the truth and then you make another decision and then another one. People wait way too long. I think we’re not taught how to execute. Just make the decision and move forward.
Rory Holland: Yeah, that’s a great way to live. You can get stuck in just thinking about it or struggling with it for too long. Make a decision and move. Some people have that in their DNA, some people don’t. So tell me about becoming an author. What inspired you to write?
The Inspiration to Write Books that Help People with Finances
Bill Bloom: My first book is called The Yachter’s Guide to Early Retirement because I’ve been on the board of our yacht club, the treasurer of our foundation, the nonprofit side of things. I spent a lot of time, effort, energy, a lot of my people whom I work with on the financial side of things are from there. So I was stuck in an airport, we were at my friend’s bachelor party in New Orleans. Everyone booked the 11 o’clock, 10 o’clock flight. I booked the 8 o’clock flight. I thought everyone was staying late, so I was at the airport sitting in the lounge and I literally wrote my first book there. I just did it there. I did the hard outline and thought, “You know what, I’m not going to waste this time. Let’s figure it out.” And I did. That’s exactly what I did.
And I thought, okay, this will be a good lead magnet. That was the truth, I wanted this to be for business and I have some of my best clients because of that book. It’s a really simple short read. I think it’s 30 pages maybe. I might be over exaggerating there, it might be 25. But I wanted something short and sweet to hand to people. And then that evolved into Retire As You Desire because my uncle came up with that tagline. We were bouncing ideas back and forth. And it’s boom. When he said that, I was “Okay, that’s it.” So I took the guts of the Yachter’s Guide to Early Retirement, hired a ghostwriter and they rewrote it into another small book titled Retire As You Desire because I wanted to be able to email that to people, give it to people and give them a short read. But this is literally the foundation of how you can retire as you desire. It’s so simple because that’s how my brain works. Simplicity is great.
And then COVID hit and I realized people were really struggling with money. They didn’t have an emergency fund and all these other things. So I wrote two books during COVID. And then 2022 hit—we had the recession, a big downturn in the market. So I wrote How to Retire During a Recession. We might be going through that right now, we don’t know. So I’m trying to give you the framework from a debt perspective for Diane Money. Free yourself up. Then I have a whole plethora of books that you could read to help get you to that phase of retirement. And then my other company helps you actually retire as you desire and we create lifetime income planning to age at least 100. That’s our goal, that’s what we shoot for, because I think longevity is going to tick up here in the next 5 to 10 years. So if you’re not planning for 100, I think you’re making a mistake there. So I’ve built a whole segment from being in debt to be able to retire, get out of the workforce, and really live your life how you want to, and that’s the messaging. Your money’s here to be used, it’s here to be enjoyed. But I think our money gets caught up in trying to please other people or other people’s expectations or what society says you should have. And believe me, I’ve been down the rabbit hole, I’ve done all of it. Buying things to impress other people. It’s all ridiculous. I wish I would have learned that a long time ago.
Rory Holland: Me too. Yeah. Did you envision the structure you just described with all the businesses and the books and everything, did you envision this all coming together 20 years ago? Was it ever on your mind that you would have all this at this stage in your life?
Bill Bloom: The first year that I worked at Prudential, I knew there should be a technology to handle a lot of this stuff for you. I didn’t know what it was, but I thought working there is “Why isn’t there a website or something that could do all this work for you?” And then I built Diane Money. So it’s kind of funny, I had the foresight for that. I didn’t know what though. I didn’t know what that was going to be. But I remember where I was at, what I thought when that happened. When that brainwave hit, I remember exactly that moment.
Building Diane Money Seemed Like an Insurmountable Challenge
Rory Holland: Yeah, I wanted to ask you—what has been one of the greatest challenges in your career that you didn’t think you could ever overcome?
Bill Bloom: It’s all about Diane Money. Here’s the story. Oh boy. This was so frustrating because this was named after my mom and the first developer that I hired, they completely screwed everything up. Nothing worked. Literally nothing works. So that was over probably $115,000 wasted. Gone. Poof. And he actually overcharged me because I had to go through everything and I got some money back, but still, it was literally lit money on fire. It’s getting your master’s degree without a diploma. And then my friend comes along and says, “You know what? I could do this. This will be easy.” Sure as heck wasn’t easy because they screwed it up too. Their developer in India did not create the different staging environments. So everything was pushed to production. So that was another maybe $100,000 just poof, gone.
The Role that Faith Plays in Finances
Bill Bloom: But because we were all in strategic coach together and were close with Dan and Babs, we’ve had dinner with them and spent time with them, I got a really good sweetheart deal from this. Because the folks who built it, out of their own generosity, they paid to rebuild the back end and make this right. But this is when we transitioned over to the debt side of things, to pay off the credit cards and student loans, etc. because you could put all your debt in there. And I didn’t know what was going to happen but I just didn’t quit. Just didn’t quit. And then it’s at such a solid place right now where we’re: how do we tweak the onboarding? How do we make it easier? How do we provide more value? And this has been over four years. Most people would have quit the first time. So, Rory, to answer your question, it’s purely Diane Money. But it’s all meant to be. Again, these are all learning lessons. Life is a pure learning lesson. And when you let go of trying to control it and just let it happen for you, you’re going to see why things are happening to you. And no one’s a victim. We are all responsible for our own lives.
Rory Holland: No, I love that you said that. I’d love to talk about it. One thing that we share that seems pretty clear based on some of the language you’re using is faith. And there’s some surrender in that, not surrender you’re just gonna lay down, but surrender in accepting that life’s hard, it’s gonna be tough and great things take time. So it sounds you’ve had a conviction for Diane Money and you felt led to do this. Where does that come from for you?
Bill Bloom: I mean, I have five follow through. So I’m not from a Colby perspective, a five, five, eight, two. I’ve got a five follow through and this has taken a lot out of me to get to this point, but reading The Surrender Experiment, so many books along these lines of when you let go, that’s when things come to you. And I’m still working on this. Nothing’s ever perfect, right? My life, no one’s life is perfect, but you have to keep working at these things. And when you let go, again, that’s when things come to you. When you just stop trying to control everything, that’s how we got introduced, right? I just sent you an email. “Hey, would love to be on the show.” And then you let it go. And then look at what we’re doing right now. So many times in my life, things have happened. If you truly allow yourself to just be present, you can call it faith. God is in us. It’s not going to church. It’s not going to the mosque. It’s not going to any of that stuff, your temple. It’s in you. Those things are all distractions. It’s in all of us. That’s what I believe. And if you just allow yourself to be yourself, and be authentic and just be in your aura and your positive energy, nothing really matters. Life will be great because things will happen for you. It’s really a mindset.
Rory Holland: Yeah, I think that’s the hardest part about being an entrepreneur or being a type or different descriptions people use, right? We’re all driven in certain ways, but that drive from what I hear you saying is that that drive can be grounded in something versus just driving for driving’s sake, which would be driving ourselves off a cliff. We burn out. We make poor choices. We hurt people. But coming back to what you said, that’s how I take it, it’s not being content or surrendering from the perspective of not taking action because you got to be responsible. You got to be accountable to your choices and you have to make good ones in leadership in your home and your work in your community, whatever it may be. But letting go a little bit and not always needing to be in control. I think that’s so hard.
Bill Bloom: It’s so hard because you want the outcome, but it doesn’t work that. Once you realize that, then things open up for you. You just have to let it happen for you. And if it doesn’t happen, it’s not meant to be. That one thing that you desire, something better is going to happen for you. That’s the silver lining.
Rory Holland: Yeah, and you just gotta stick with it.
Bill Bloom: Yeah, you gotta keep going. I mean, I’ve had huge opportunities in my career and they fall apart at the last minute. Things just didn’t work out. And it’s all been a blessing. All of it has.
How to Connect with Bill and Diane Money
Rory Holland: Amen to that. And I’ll say that it’s a blessing knowing you. I’m so glad that you reached out and as we’ve gotten to know each other through a few conversations, this has been wonderful. I love the work that you’re doing at Bloom Financial. Diane Money’s fantastic. I can’t wait to see that continue, get in the hands of more people to help more people. How can people learn more about Diane Money, Bloom, and find your books?
Bill Bloom: Yeah. All of our books are free on our website. You can go to bloomfinancialco.com, we give them away. So no email, you don’t need anything. Just read them. Because they’re good. It’s not because I wrote them. They’re short, sweet to the point where you can get great information quickly. It’s not a 500-page book that you’re not going to learn anything from. But Diane Money, you can go to dianemoney.com. We are in the Google App Store, the Apple App Store. Just use it. We have a really cool feature, Rory, that you could pay what you feel the app is worth. So if you’re struggling financially, just use it. There’s no excuse for you not to. Just pay a couple bucks a month, get value from it, and see where you’re making your mistakes. You’re going to be able to course-correct a lot faster than you using Excel or trying to do it yourself. It’s a really simple thing and we have so many great stories from our users from saving over $16,000 of interest or the banker story who saved three grand in two months. Anyone can do it. You have the power. So just try the technology. Diane Money app, use it. We’re in both of the App Stores. There’s no excuse not to.
Rory Holland: If someone wants to get in touch with you, I assume LinkedIn, through the site?
Bill Bloom: Yep. LinkedIn, website. Super active on all of that. So definitely available and happy to collaborate. We’re working with different banks and credit unions to roll this out to their banking customers because then they’re able to find refinancing opportunities, they’re going to show value to their banking customers. There’s a lot of cool ways to use this.
Rory Holland: Man, I’m grateful to know you. You have such a good heart for helping people.
Bill Bloom: Thank you. Same, same.
Rory Holland: Yeah, it’s been wonderful. Well, thanks for being on the show. Very grateful.
Bill Bloom: Thank you for having me.
Outro
Rory Holland: In life, it’s better to work on yourself than it is to wait for the world around you to change. And that’s what Matthew McConaughey means about getting comfortable with being uncomfortable. Check out his conversation with Simon Sinek. It’s excellent. We live with the illusion of control until a tragedy or an outside force shatters it. What if Bill had given up after the first developer failed? Or when the second version wasn’t ready for launch? He could have taken those as signs to stop. After all, he had a successful business working as a wealth manager. Why spend so much time and money trying to help people get out of debt? As Simon Sinek might tell you, Bill’s “why” is about helping people achieve financial freedom. But one person can’t solve systemic consumer debt. We all need to ignite the internal fire that drives action and change. What Bill is doing with Diane Money is helping a lot of people change their lives. And it already has.
