Charlie Epstein, Creating a Life of Desirement with a Yield of Dreams (#235)

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Charlie Epstein

Charlie Epstein is a financial pioneer who has worked in the financial services industry for over 40 years. As Vice President of Wealth and Retirement at HUB International (previously Epstein Financial Services), he is responsible for over a billion dollars in assets under management. The company helps entrepreneurs, medical professionals, and people from all walks of life to create “paychecks for life” with retirement plan consultation, fee-for-service financial planning, and complete asset management. Charlie was renowned as the 401kCoach across the country, having trained over 10,000 financial professionals on how to best serve the needs of their clients. He has also written two best-selling books on the topic, Paychecks for Life: How to Turn Your 401k Into a Paycheck ManufacturingCompany and Save America, Save!: The Secrets of a Successful 401(k) Plan.

Charlie Epstein has also worked as a professional actor in roles ranging from Shakespeare to Neil Simon, as well as stand-up comedy in New York and improv with Chicago City Limits. What makes Charlie’s story unique is how he has incorporated acting and entrepreneurship, something that he has manifested with the production of his solo show, Yield of Dreams – Paychecks for Life. His show takes people on an experiential journey using humor, storytelling, animation, and gamification to engage and inspire the audience to achieve their wildest dreams.

Entrepre-trainer and Entertain-eur

Charlie’s philosophy is “Do what you love and the money will follow”, something that he has been able to successfully implement by being both an “entrepre-trainer and entertain-eur,” which is what made him turn his dreams into reality. He approaches his work as a financial counselor, professional actor, and bestselling author with the same enthusiasm and creativity, putting the entrepreneurial mindset on stage, and his entertainment skills in the financial world.

With his eccentric approach in all of his ventures, Charlie motivates others to live life with an infectious spirit bound freedom for curiosity, joy, laughter, and play; to chase their aspirations and attain the success that comes with living a life they love in all of his endeavors, Charlie motivates others to live life with curiosity, joy, laughter, and play; to chase their dreams and achieve the success that comes with living a truly aligned and abundant life.

And now here’s Charlie Epstein.

Show Notes

[3:31] How’d it happen for Charlie Epstein
[9:48] Did he grow up working in the business?
[11:27] Charlie’s life in college
[15:47] What does he collect?
[17:23] Starting his business and getting a mentor
[22:43] Charlie’s biggest lesson in business
[31:07] What’s in his DNA
[34:36] On selling his company
[38:48] On his one-man show
[48:07] Find out more about Charlie and his show
[51:15] Outro

Full transcript below

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Podcast with Charlie Epstein. Creating a Life of Desirement with a Yield of Dreams.


charlie, strategic coach, paychecks, entrepreneur, podcast, shares, selling, dreams, talking, taxes, life, story, days, funny, college, 401k, epstein, discovery, successful, create


Mike Malatesta, Charlie Epstein

Mike Malatesta  00:13

Hey, everybody, welcome back to the How’d it Happen Podcast. I am. So happy to have you here today as I am with every episode, and I am fulfilling my promise to you today, as I do with every episode, to share with you an amazing success story, one that will inspire and activate greatness in you. My guest today is Charlie Epstein. Charlie welcome to the podcast. Let me tell you a little bit about Charlie and you kind of get excited like I am for the for the show. So Charlie’s philosophy is do what you love and the money will follow. And he is an entrepreneur, although he has funny names for this that I’ll let him talk about on Trip pro trainer. And, and turret entertain, or I think it reads better than it print than I could pronounce it. So I think I’m just gonna go with I’m just going to answer, Tina. Okay, it says trainer. Entrepreneur. Okay, so anyway, Charlie is an entrepreneur. He’s an entertainer. He’s an author. He’s a podcaster, and a ton of other stuff. He has simultaneously straddled both worlds and successfully achieved his dreams that being an entrepreneur and entertainer. He brings the same passion and innovation to his work as a financial advisor, professional actor and bestselling author. In all of his ventures, Charlie inspires individuals to live life with an infectious spirit, bound freedom for wonderment, joy, laughter and play to pursue their dreams and achieve the success that comes with living a life you love. How can you how can you not get behind that? Charlie has known nationally as the 401k Coach, having trained more than 10,000 financial professionals how to best serve the needs of their clients. His two best-selling books at least to our paychecks for life, how to turn your 401k into a paycheck manufacturing company love the subtitle on that book. Charlie, and save America save the secrets of a successful retirement plan. Most recently, Charlie has combined his acting and financial talents in the creation of a new one-man show called yield of dreams paychecks for life. Working with a team of professional comedians, Charlie has created a financial theater experience designed to make money funny while illuminating the 15 minutes of money that inhibit people’s ability to achieve financial independence and live the life they they’ve always dreamed up. Charlie’s podcast is called I believe it’s called same thing yield of dreams paychecks for life. Is that correct? Charlie? And I’m looking forward to being on Charlie’s podcast later So Charlie i i start every show with the same question, which is how did happen for you huh okay, well you get second for that I had someone else tell me that as an answer out of 200 and some episodes that’s only the second one where it’s been born oh it’s. And Where Where did both of those get started? I mean, we heard where the laughter started that happened when you got hit on the butt butt



Charlie Epstein  08:27

that’s right yeah

Mike Malatesta  09:06

and what was it? So let me ask let me ask you about your your high school production days. What’s the what’s the most memorable for you? If you have one, you know from your from your high school days. A role


Is there anything that you do forget Yeah, okay

Mike Malatesta  10:37

okay walked right into that one. Matt your producer called me Matt So my name is Matt so um What else were you into in high school Charlie?


I underachiever yeah sure

Mike Malatesta  12:02

everyone you okay so you decided to go get a degree in economics when you went to college was there I always I always loved talking to people whose parents were entrepreneurs because I always think to myself okay, did you grow up working in the business and was it something that you liked to do? Yeah, that’s a lot of money right did you oh go ahead No, go ahead finish Did did you I guess when you got to to college did you continue with the productions and did you do I don’t know if you did sports in college. I’m just trying to like what was your life like difference in college versus high school?


Yep Okay That

Mike Malatesta  15:53

That’s a true story you just stopped dead and we’re like that’s that’s I’ve had I’ve had enough I’ve yeah okay that is


right yeah

Mike Malatesta  16:41

maybe my parents should have told me that because I was an English major that although right yeah I think I learned how to think too as an English major because that’s all you do you know you take one yeah okay


huh yeah and I bet right

Mike Malatesta  17:48

I bet that came in handy too when you wrote your books because that’s a big part of writing a book is you have to trim trim trim trim


trim right to get hopefully

Mike Malatesta  18:01

you mentioned Charlie collecting the the art from your from your grandfather I think was your grandfather and then the comic books it made me think to myself do you collect what else do you collect? I don’t know if you ever collected still still collect comic books or what else but what do you collect


ah got it

Mike Malatesta  19:12

Okay, I like to ask people about that sometimes because some people just are very very into you know collecting things and it’s always intriguing to me what makes somebody tick when it comes to that kind


of thing okay got it. So okay,

Mike Malatesta  19:39

when you when you got got through college you did you start your business right away or did you continue to act after that, that kind of thing you may have but what was the path


Huh Of course yes



Mike Malatesta  22:15

yeah but yeah yeah in a lot of ways he in a lot of ways he


was yeah right what what

Mike Malatesta  22:56

what were some of the things that you remember him saying to you that kept you going because so if I understood it right 14 years selling life insurance with him Is that correct or


are okay with him okay yeah sure gratulations okay and it’s

Mike Malatesta  24:22

okay, a lot of times I think to myself like who have been my mentors and I’ve I feel like I’ve gotten you know pieces from a bunch of different people but I always I always struggled to identify one person so clearly like you identified him and it always makes me you know long for you know wanting to change that sort of maybe you could say I’m in the gap about that because


it Yeah, yeah so Right Sure. Okay


so you turn the tables on his threat basically yeah so okay well I’m gonna give you some

Mike Malatesta  29:00

well thank you I’m so I’m honored by that and I’m also kind of blown away that you would have you know told this very glowing story about your mentor and never brought up any of that other stuff and I feel like a lot of people in your shoes would skip the story skip the first part of the story and they would make up something else because you wouldn’t want to give that credit to someone who ultimately or at least it seems like may have betrayed all that was yeah threaten to of course yeah


right All right what he did right yeah it’s lawyer

Mike Malatesta  31:32

yeah well not just a lawyer, but not just a lawyer I


guess I would say yeah. Right. Right right

Mike Malatesta  31:53

I was saying to talking to my wife the other day about because I do agree with you that there’s this narrative right that if you’re a successful entrepreneur or successful anything that somehow you got that by taking it away from someone else so it’s exactly the opposite of what we learn in Strategic Coach and abundance 360 and all these other things right you create more you don’t take away but there’s this narrative that I think a lot of people and a lot of politicians prey on, which is we’re going to create the story about how if you’re successful you’ve you’ve done something that you know, that’s that’s been wronged or taken away from someone and on top of that you don’t pay any taxes. And it reminded me of a couple you know, the last couple of weeks, Elon Musk has been selling the shares of Tesla, right. And he said, Well, why are you selling the shares? Well, I got a tax bill, billions of dollars of taxes and I think, where’s the front page story about how much taxes he’s paying, you know, on whatever his options were? And that’s just one example of that. There’s always a story written about someone who didn’t pay any taxes and that’s like a headline but I don’t know I never got away with that. Charlie. I already I always had to write big checks for taxes because that’s part of the game when you Yeah, I’ve been that I’ve been there unfortunately. But but that’s the way that’s the way it goes.


That’s the way it goes.

Mike Malatesta  33:22

So Charlie, I wanted to ask you when this you know you the first couple years and the life insurance were were miserable. Sucked I think is the word you used and I’m wondering you know, it sounds like this Wunderman Joy laughter in play is something you grew up with but did it how did it did that experience take it away from you and then you had to get it back? Somehow? Right Yeah, it was it eat what you kill sort of thing.


Right I love what you Yeah.

Mike Malatesta  35:53

Yeah. When it gets hard is, right. Yeah. And that’s and it’s, it’s the, you know, people say all the time that, you know, maybe entrepreneurs are born and they’re like, you know, it’s different. And I think there may be some of that, but I think, really, for most of us what it comes down to is, like what you just said, you know, are you going to stop like 90% of the people are 85 or 95? Or what are you whatever percentage you put on it? Or are you just going to keep going? And the ones that keep going? You know, that that just being on the path helps you figure out something that getting off the path wouldn’t at least that’s how I feel. Now Yeah, yeah, yeah, yeah. Good. Good, good. So can I ask you about you know, how you came to the decision to sell your company and because I have my own story that we can, you know, talk about at some other point but it’s always it’s never well, sometimes it’s an easy decision if your real backs really up against the wall or something that doesn’t seem to be the case for you and you know, your names on the door you know, it’s your the 401k Coach, I mean, you got this whole brand about Charlie Epstein and it’s tied to your company now I know there’s other parts to it I’m not saying that’s a soul thing but it’s still it’s it’s a challenging decision I think.


RIGHT. Okay Right, right Right Okay,

Mike Malatesta  39:58

well, I like that. Thank you for explaining that. because that’s



Mike Malatesta  40:12

right right yeah, yeah well there were I had funny but from my Strategic Coach days I had these goal we had a decade long goal planning back back in the day so I had my goals from when I was 40 to 50 and 52


So let’s go ahead finish try okay the the

Mike Malatesta  40:42

Yeah, sounds like a nice situation so with with Yoda dreams this one man show How long had you been kicking that idea around? And was it like you know like those goals I was talking about in my for my Strategic Coach days where I had these goals that I wanted to accomplish and I wasn’t getting to them because I would always put the excuse of the business in between that’s really what it came down to it wasn’t because I couldn’t do them it’s just I made excuses for myself and I wanted to get to those so I’m curious for is that something similar or did this just sort of pop in your head one day when you are in your discovery mode and you’re like okay I’m gonna move forward on that



Mike Malatesta  42:32

and and balls which you got from


the yeah YEAH? Right And

Mike Malatesta  44:31

and so if you well, you described yourself as perhaps being a coward back when you were, you know thinking about going to New York and being a starving actor and then you do you think do you think if you hadn’t run into Mike and he didn’t have this skill set in this collaboration mindset do you think you’d still be I don’t want to say dragging your heels because I don’t know if that’s what you were doing but it’s sure so Seems like you had this thing in your mind and it was and of course once you have what is the what is the dance say when your brain is open to something your eyes and ears find it or something like that and it sounds like


yeah yeah yeah




right yeah




right yeah right Right

Mike Malatesta  47:17

so it exceeded your expectations right off right out of the gate



Mike Malatesta  47:36

what do you think it needs to be better




more drama less talking Okay


funny okay yeah

Mike Malatesta  49:00

right the skinny branches I’ve heard you call it before


okay so the right

Mike Malatesta  49:14

so 30 city tour when do you are you touring now with it you mentioned the two sold out shows but so you did the two shows and then you


yeah okay right repeat yeah Nice

Mike Malatesta  50:05

nice how do people see it or find out more about Charlie? Yeah and also in abandonment about it or some similar word where they just ignore it right just


hopefully it’s there. Right?

Mike Malatesta  51:29

Well Charlie’s, by the way Nick Nanton was on my show you have you had him on your show that he’s he’s fun. He’s he’s really fun and I’m going to watch that documentary. I didn’t get a chance to do that yet but I’m going to I’m going to find out and watch it started Hollis. Do you want people to get a hold of you? Is there any other way that you I connected? Desire meant I really like that’s a great, that’s a much better word than retirement desire, man. I love it.


Got it? Well, Charlie,

Mike Malatesta  52:32

this has been a very awesome first conversation. I’m so happy that you joined me today. And thank you so much for coming on and sharing your story sharing something new about you that you hadn’t shared on the podcast before. That’s always great. And and just congratulations on you know, being a person who’s committed their life to wonderment joy, laughter, play and discovery. I always forget the last one discovery Yes. Which I equate to curiosity but so it Yeah, it’s been a great podcast. Thanks so much for coming on. Really enjoyed it sounds good? Okay, sorry about the microphone thing that’s happened. I don’t remember that ever happening before. Yeah, my pleasure. Yeah, I wish really fun I’d like to later maybe we can do it again sometime because there’s a lot of other stuff to get to and you know, you’re just really fun to talk to so and easy to listen to. I will say that too. I’ve listened to you a bunch and it’s really easy to listen to.


Alright. Yeah, I’ll

Mike Malatesta  53:47

log off here. I’m gonna go to the bathroom quick and then I’ll be back.


Okay, thank you. Alrighty, bye bye.

Mike Malatesta

Mike Malatesta

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