Bill Bloom – Be a Boss with Diane Money (296)

Share this blog:

Bill Bloom - Be a Boss with Diane Money (296)

In this episode, I welcome back Bill Bloom and we talk about the amazing new financial goal planning app he’s developed called Diane Money, Powered by Artificial Intelligence, Diane Money helps users set, plan for, and achieve their money goals. Sign up for the beta version in the Apple or Android app store. It’s free – and priceless – to use.

About Bill Bloom

Bill Bloom is an independent financial planner and principal of Bloom Financial Company. He helps individuals and business owners understand their current financial situations, define future goals, and develop a flexible strategy that will allow them to reach their retirement objectives. Bill provides clients with practical techniques for a variety of financial issues, such as investments, risk management, tax planning, and insurance needs assessments, enabling them to “Retire as You Desire.”

As an independent financial advisor, Bill has a lot of options for tools, services, and solutions that are in the best interests of his clients. He understands that every client’s situation is unique and requires a customized strategy. For Bill, it is not just about creating a plan, it is about building long-term relationships.

He holds “Retire as You Desire” educational events for clients and guests on a regular basis. Bill believes
that when clients truly understand the financial landscape of retirement, they make better informed
decisions about their retirement planning.

And now here’s Bill Bloom.

Full transcript below

Video With Bill Bloom About Being a Boss With Diane Money

Watch the Taxes in Retirement Masterclass by Bill Bloom

Visit to Learn More About Bill’s App

Discover Bill Bloom’s Website

Check Out Bill Bloom’s Books

Listen to the Retire As You Desire Podcast

Follow Bill Bloom on LinkedIn

Get Motivation, Inspiration, and Ideas to Level Up Your Life.

Subscribe to the How’d It Happen Podcast

Want to be the first to know when new episodes are released?  Click here to subscribe

This image has an empty alt attribute; its file name is Howd-It-Happen-Podcast-Listen-on-Apple-Podcasts.jpg
This image has an empty alt attribute; its file name is Howd-It-happen-Podcast-List-on-Google-Podcasts.png
This image has an empty alt attribute; its file name is Howd-It-Happen-Podcast-Listen-on-Stitcher.png
This image has an empty alt attribute; its file name is Howd-It-Happen-Podcast-Listen-on-Spotify.png

Thank you for being a How’d it Happen listener. Please enter your email address below to subscribe, or subscribe on Apple Podcast, Stitcher, or wherever you like to listen.

Subscribe to My Newsletter


Write a Podcast Review

Also, podcast reviews are important to iTunes, and the more reviews we receive, the more likely we’ll be able to get this podcast and message in front of more people (something about iTunes algorithms?).  I’d be extremely grateful if you took less than 30 seconds and 5 clicks to rate the podcast and leave a quick review.  Here’s how to do it in less than 30 seconds:

Click on This Link –

Click on the “Listen on Apple Podcast” Box

Click on “Open iTunes” – You will go directly to the iTunes page for the Podcast

Click on “Ratings and Reviews”

Click on the 5thStar (or whatever one makes the most sense to you 🙂

Podcast with Bill Bloom. Be a Boss with Diane Money.


money, people, bill, diane, thinking, app, pay, financial, goals, blum, company, student loans, life, wind, built, work, colby, bloom, student loan debt, collaborators


Bill Bloom, Mike Malatesta

Mike Malatesta  00:14

Hey everybody, welcome back to the How’d It Happen Podcast powered by WINJECT Studios. This is a really special day for me, because I’m bringing you another amazing success story that you’ve heard part of. In episode number 130, which was a long time ago, we’re up to 270-something now. But in episode 130, you got to hear all about Bill Bloom’s. How’d It Happen story, and Bill is joining me again today. Bill. It’s such a pleasure to have you back on the show.

Bill Bloom  00:51

Mike, thank you for having me. I always, always love spending time with you. I love how you have the ownership hat on right now for the folks watching on video. I love the book. I’m gonna listen to it as well. So for y’all, you are gotta read it. Gotta listen to it. It’s an incredible book. It’s helped me already. So thank you, Mike.

Mike Malatesta  01:09

Um, well, thank you, my pleasure. So see, that’s a great way to get a podcast started, you compliment the host. And then everything goes really well from there. So you can see that happy Bill is very smooth as well. So anyway, Episode 130. You can learn all about Bill. Today we’re going to talk about something that’s more recent than the last episode. But first I want to tell you a little bit about Bill Bloom. First, I want to start Bill Bloom is a friend of mine and a collaborator. I think Justin Breen connected us at some point but knowing Bill has made a difference in my life. He’s just a very, very kind, genuine and abundant-thinking person. And those are the kinds of people that I enjoy spending time with. So thank you for that. Beyond that, Bill is an independent financial planner, and the principal of Bloom Financial Company. He helps clients ‘retire as you desire,’ which is also the name of Bill’s brilliant podcast that has two episodes a week, check that out, Retire as you Desire. He helps clients by providing them with meaningful strategies to a wide range of financial matters, including investments, risks, manage risk management, tax planning, as well as insurance-needs analysis. He’s based in Chicago, but he works with people all over the country. And you can find out more about Bloom Financial and Bill at his website, which is bloom And today, I’m going to ask him the ‘how’d it happen’ question, but we’re going to focus on this new development that Bill has created called Diane Money. So with that built, let’s get started, how did it happen?

Bill Bloom  03:06

How did it happen? Well, this one’s definitely going to be different from Episode 130. That was, I think, one of the first podcasts, Mike, I’ve ever been on. So things have definitely changed for us here.

Mike Malatesta  03:17

You’re probably an expert now. But I’m glad we I’m glad we broke that ground with you. Very good.

Bill Bloom  03:23

Absolutely. It was such a great learning experience and talking about learning, talking about growing, the whole premise and the whole purpose of doing things in life, you have to start, no matter if you’re building a big company, or you want to start a family or you want to do this, that or the other, you have to start. And Diane Money came from the same story of my childhood where my parents couldn’t figure out how to make $1 work for them. I mean, when my mom passed away about a year and four months ago, now, Mike, they had the same amount of debt on their house that they took out when they bought the house over 30 years ago. Oh, same amount. Okay, is. So I grew up in a really painful but a very loving environment. The painful side was the whole financial aspect. I mean, there were so many times when my parents would be fighting. How do you figure out how to pay the mortgage, who’s gonna pay that? How many months later, there’s always issues with that. And now my wife and I have our second kid. That was something that I never ever, ever wanted to have in my life. And that’s why I built Bloom Financial, my first company, because I wanted to just have that financial freedom, but also give other people financial freedom. And then here’s how it really happened to really get into the details of things. I was sitting in a Strategic Coach session with Dan Sullivan. And this idea popped into my brain. Now you and I have the same Kolbe, A lot of people probably know about that who listen to your show. But I was thinking about, how can I create a company that’s going to show your relationship with money, whether it’s good, bad or indifferent? And then I thought to myself, if I create this, who’s going to use it? Who’s going to pay for it? What’s the point of it? And there really wasn’t one. So I’m glad that I hit the brakes with that, stopped doing that, because that would have been a disaster. But

Mike Malatesta  05:31

where was that company going? Like, what in your mind? Where was that? Where was that going?

Bill Bloom  05:37

I thought that I could create this really cool assessment. And people would pay for this, where they could understand their mental and their mindset around their money, whether they’re stressed spenders, or they are happy spenders, or they are super scared and they save every penny because their parents had a bad experience, or they came from a different country and they didn’t have much right you hear those success stories all the time. But that’s where that was going. Like, I wanted to really dive deep into that. And I talked to the people at Kolbe. Yep, we’re not, we’re not into that we don’t do those sorts of things. And I’m glad they said, No, I’m glad I didn’t waste a lot of time on that. And that helped me really dig deeper into my vision. And that was to help more people on a bigger scale. My time is limited, just like Georgia, we have our 24 hours. So leveraging the technology is really what helped me build Diane Money to where it is right now. And going back to my parents’ situation, going back to a lot of people’s financial situations here in America, you get your paycheck, or when you get your dividends, or you get your distributions from your corporation, a lot of people don’t know where their money goes every day, every week, every month, every year. And then you get to the end of the year, it’s like where’s all my money. So what I’ve done is I’ve partnered with collaborators to build the technology, using artificial intelligence, to look at where your money is going every single day, every week, every month, and then start to give you different ideas and recommendations based on your goals. So it’s all going to be about you. And the app is going to do the thinking for you to take the guesses and stresses out of your financial life.

Mike Malatesta  07:37

Okay, first I want to go back to this idea that you abandoned before we go forward. So you had this idea to create an assessment tool. So think about that, I think, is it fair to say people think about that as a survey of sorts? Like, here’s a bunch of questions to answer? And the result is going to be some score, like, you know, ‘how you feel about money score,’ or whatever. And you had seen that as something initially where people might pay to do that. And then what would, in your mind at least, and I know you’ve abandoned the idea, so I may be asking you something that’s unfair, but I’m interested in iteration. You know, if I’m asking you anything that’s unfair, just say so, but in your mind, after they get the score, where’s that going to go?

Bill Bloom  08:29

That’s where I hit a roadblock. Like that’s where I’m like, Okay, I need to pump the brakes with this because it was going to just be an assessment. It’s not really a company and a guy by the name of John the Dukkha, he and I were having a conversation about this, his wife used to work at Strategic Coach actually many years ago. Okay, and he’s like who’s gonna pay for this? And then I go I have no idea. I had the idea. I was starting to kind of get the ball rolling in my head because my eight Quick Start, okay, let’s go go go, but I’m thankful I put the brakes on that. Because what are you going to do after that? Build courses and do this and do that? I didn’t want to do that. That was not my unique ability. That’s not what I’m good at. I could find who can do that for the company, but it seemed like it was gonna be a big distraction from my current company at the time and it was really growing really, really well and still is. So it was a great form of restraint on my part.

Mike Malatesta  09:37

Okay, because I thought maybe you were thinking, you know, do the assessment, you get the score and then you get a chance to talk to Bill so it’s like a lead generation sort of thing, but that’s not what you were interested in, it sounds like

Bill Bloom  09:53

I wanted millions of people to pay for it. Use it, figure out their money Kolbe and

Mike Malatesta  10:00

And then take it from there and be Yeah, okay. Okay. All right. So, you mentioned that meeting with John. Tell us about the meeting you had that, or the experience you had that sort of connected that first idea with what has become Diane Money.

Bill Bloom  10:26

So this was right before the pandemic started. Literally, we had, I think, the last in-person session with Dan, right before the pandemic started, okay. And that’s where the ideas were really coming to fruition, because you know, you’ve been there, when you’re in the room with the people, magic happens, these ideas come out of nowhere, you’re talking to people. And there’s something really special about that. And that’s where the whole artificial intelligence, taking the mind Kolbe, the thinking tool, into an actual application, a platform where you can have something do the thinking for you. That way, we all have stress with money, we all have money problems, whether you have not a lot, a little bit, middle of the road, or millions and millions of dollars, there’s different money problems along the way. But the majority of people have student loan debt, they have credit card debt, they don’t know how to really efficiently use their money. And that’s the majority of people. I’m guilty of that too. I’ve been in the business for almost 14 years. But who wouldn’t want to use a tool that’s going to do the thinking for you, and help you reach your goals sooner faster, quicker and more efficiently? And that’s why our app is so different from everyone else’s. There’s a million financial apps now. But this is purely AI-based to do the thinking for you just so you don’t have to stress about this anymore.

Mike Malatesta  12:03

Okay, you’re saying that there might be people who are stressing over the fact that it’s AI-based. So what does it actually mean, Bill? Because even I get confused sometimes. Like you say, Okay, we’re going to use artificial intelligence, and that’s going to help you. How does it? How does it really work? Can you explain it like, you know, like, sort of to the fourth grade? Yeah, absolutely.

Bill Bloom  12:33

Thanks. So the fourth grade, I kind of act like that most of the time. So that’s a way to do this.

Mike Malatesta  12:39

Me too. That’s why I brought that up. Thank you. Single syllable words are always good. Yes. Like your name Bill. Bloom. Yeah, teaching a thing. Totally different than mine. It’s so confusing. All right, sorry.

Bill Bloom  12:53

Oh, good. All right. So the fourth-grade-level explanation, it’s, I’m just going to tell you a story on how to think about this. So imagine if you’re 30 years old, and you have $30,000 of student loan debt, you have a 6% and 8% and 9% interest rate on there. You have a job, you’re doing pretty well. You’re renting, you have $100,000 of a salary. You have a goal to pay off your student loans. By the time you’re 35. You want to go to Cabo, because you have a friend’s wedding in two years, because all the weddings have been delayed now. And then you want to save $3 million for your future retirement goal. So how do you look at your $100,000 of annual salary? After taxes, after your health insurance, your 401 K? And where do you put your money to make it work for you? So the app is going to break down those numbers for you. Because you put your goals in there. You tell us I want to have my student loans paid off by the time I’m 35. So it’s going to give you those suggestions on how much to pay off per month. So you don’t have to think about it. That’s the guesswork eliminated to do the $3 million of retirement. The app is going to do the thinking, where pay off first, especially that 9% one because there’s no arbitrage there. And then we look to put that freed-up money from the debt perspective into the future retirement, the future investing and how much should you be doing a month to get there? How much risk are you willing to take, I mean, everything’s a risk. I love how Jim Rohn says that everything’s a risk. First you don’t invest. But the price of not knowing it, and the end is much greater than not taking the risk now, so that always sticks in my mind. So that’s the fourth-grade-level view, from a thinking process is just algorithms, it’s smart-thinking computers to do the thinking for you.

Mike Malatesta  15:29

Okay, so the user puts the goals in, do they also put in their spending? Or how interactive does someone need to be with the app?

Bill Bloom  15:43

yes, so we will connect the bank accounts, and the credit cards and analyze all of that, through Plaid for you. Plaid is a 250-Encrypted service that really helps you connect your bank accounts, it’s I think it’s the most widely used one here in America, huge financial company. And that’s where the data is gonna really flow from, Mike. And that’s, that’s the fun part. That’s what makes it customized for you . It’s like, we’re gonna look at your spending, we’re gonna look under the hood, basically, you know, we’re gonna,

Mike Malatesta  16:21

okay, so you’re gonna take away the. . . you know, if I have to write things down myself, for example, I may not tell you everything, because you know, the latte or the expensive dinner, I know, I’m not supposed to do that. So I’m going to tell you that I didn’t. I mean, I did. And I’m going to fool myself into thinking that it never happened.

Bill Bloom  16:46

You hit something right on the head there; we want people to incorporate that into the app, we put in there, I want to go to out to dinner three times a week, or three times a month, whatever your lifestyle is, put money towards that. And then we’re going to give you the recommendations to move that money here, there or everywhere for you. So that you can do with that. Or you can do the latte. You know, penny pinching the last days. I don’t really agree with that. I think you should spend your time doing a new skill, getting a better job, starting a side hustle, getting the company going. I think that’s how you get ahead, not the penny-pinching thing. So the app is really an abundant mindset-type aspect. And we want people to have fun with it and make money fun. And we have a really cool feature that makes it shareable. So when you pay off your student loan, share that with the world, celebrate that ,we want the people to send us their videos on our social media, send it to us, and we want to share that for you. Because we want to celebrate you, we want to celebrate the user. And if we can make money fun, but also make it a community where people are supporting each other. That’s a big win right there.

Mike Malatesta  18:11

So, I don’t know if gamification is the right word, but it sounds like there’s a little bit of, you know, woohoo, sort of as you go along, like, Yes, we did it. Right? You earn something you earn?

Bill Bloom  18:27

Absolutely, we should celebrate this, I celebrate my wins all the time. But I had to learn that skill, I had to figure out how to do that. The little ones mean everything. But if we can start getting people to celebrate those things, for instance, when you do pay off your student loan, that’s when you go take that trip to Cabo, or you go to France, or you go to Japan or Argentina, wherever. But if you don’t know where you’re going, you never know where you’re going to end up. The wind will take you anywhere. And that’s the whole premise. Set a goal, start somewhere, it doesn’t need to be perfect, you could change it, we may need to alter course. But if you’re able to do that, in a much more efficient manner than guessing. That’s where Diane Money is going to become your motherly financial figure to help guide you down this path.

Mike Malatesta  19:34

You know, I’ve heard it said to that without a target, you miss it every because, you know, so many times you think about a goal as being one point to another point. And that’s not really how most goals are achieved, right? Like sailing, you are going towards it, but you have to go back and forth, maybe to get there. I think that’s actually apropos of how many, many goals are achieved; you start, which is what you said, you have to start at the beginning, but you can’t get so hung up on not knowing how I’m going from here to there. How exactly I get there, I’m not sure, because there’s going to be all these things that happen to me over time. And if I get knocked off course, and that makes me end because I’m like, oh, shoot, I’m not going toward the point anymore. That’s, I think that’s a real challenge for a lot of people, like, get it in your mind that you are going to get knocked off course. So take the first step, know where you’re going. But also know that the world’s gonna happen, and you’re gonna get knocked this way, that way, the wind is gonna blow, the wind is gonna blow. And wherever you go, you say, Okay, that’s a natural way for me to get where I’m going. I didn’t expect it. But it’s natural.

Bill Bloom  20:59

Absolutely. I mean, I’ve been out on the racecourse, I love being on sailboat races, especially when we do the race to Mackinaw, I have one of my sailing jackets on right now, there’ve been times where we’ve been sitting for almost a day with no wind or expect it to be a full day and it’s hot, the bugs. One time we had 32-degree weather in July on the lake; it was super cold. And other times it was 115 miles an hour of wind in my face. So you have to be ready for those things, and having an open mind to be able to change your course, that’s where you’re gonna win. And that’s where you’re gonna have these new ideas through the financial app. the Diane Money App is gonna give you those recommendations. And the best part about what we’re building is that I found a lot of great collaborators, a lot of great collaborators. And the end game for the app for a couple of versions into the future, is that we actually want to be able to do the work for you, or you give us permission to go, Okay, we’ll put the money towards your student loans for you, we’ll pay this off faster for you, we’ll do this for you to really just eliminate a lot of that thinking process and just with the click of a button. So the future is going to be bright, it’s incredible. And I’m just really, really happy to honor my mom, she was the most amazing person in the world. And I miss her dearly. I really, really miss her dearly. And, you know, this is all for her.

Mike Malatesta  22:38

So how, how does someone get Diane Money? You know? Well, first of all, who should get it? You explained some of the scenarios, you know, if you have debt or whatever, who should get it? Where do you get it? And how do you learn more about it.

Bill Bloom  22:53

So the people who should have this are the people who really don’t understand where their money’s going on a day-to-day basis. This is not a tracking tool. Like we’re not going to just give you tracking reports, we’re actually going to be giving actionable suggestions to make your life better and simpler. So I think that’s a great thing for kids coming out of college with student loan debt, people going out to get their masters who have started their careers. 18 to 40 age-range, very, very broad, right? But those are the people who are having the most financial issues in our country right now. All the studies show that. And then how do you get it, you go to That is our website. And you could sign up for the beta right now. So we are actually going through live testing. And I would love, love, love your feedback. And we have a new version being released with the plan and a bill pay service where we’re going to be able to help you pay your bills for you and actually, potentially save you money as well. Instead of paying $300 a month for your cell phone, we might be able to get that for one half. We’re gonna have some really cool and really neat tools coming out in the summertime. So definitely sign up for the beta now, the beta list has been growing and we want you to save your spot.

Mike Malatesta  24:25

And it’s Diane with one ‘n,’ correct?

Bill Bloom  24:28


Mike Malatesta  24:33

And is there a cost to sign up for the beta? What is it?

Bill Bloom  24:38

No cost. Both Apple and Android are completely free to use right now. We really, really want to get a lot of feedback. So if things are crappy, tell us want to hear that. I would love to hear the bad feedback if you don’t like this or you do like this. Even if you don’t like the colors we chose. Please, please tell us, because this is going to be built around the people who use it and their needs, it’s going to be very, very similar to the book, The Lean Startup, for the company that they built. It needs to be around the users and we just want to make their life so much better. And that’s what the target is.

Mike Malatesta  25:21

All right, well, Diane Money, pick up the app, sign up for the beta. Sounds really cool., I kind of think about it like a diet, though. So yeah, that I know, I need to lose weight. But I don’t want to go on a diet, right? So Diane Money is going to help you lose the weight without putting you on a strict diet. It’s going to teach you over time to do the things that you say you want to do, right? You’re telling it what you want to do. It’s going to teach you and encourage you to do the things you say you want to do. Am I overstepping my bounds there?

Bill Bloom  26:00

It’s that perfectly. Yeah. Why would you limit yourself, make it abundant, make it big, set budget goals and let us help you figure out how to get there.

Mike Malatesta  26:11

All right. Bill Bloom, thank you so much for coming back on the show. And congratulations on this, this breakthrough and for honoring your mother in such a special way.

Bill Bloom  26:21

Thank you. Thank you so much for having me back. It’s always great to spend time with you. And again, you have to take action. Just go for it. Have fun, learn, make mistakes, and always, always, always have your destination on the horizon.

Nice. Thanks, Bill.

Mike Malatesta

Mike Malatesta

Leave a Replay

About Me

I help entrepreneurs get unstuck, take back their power, achieve their life objectives, and create the futures they want.

Listen to the Podcast

Get My Weekly Newsletter

Recent Posts

Sign up for My Newsletter

By signing up you will get the weekly “Inspire & Activate Greatness Blog” every Thursday.