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In this heartwarming episode, I had the pleasure of welcoming Jonathan DeYoe, a true sage in the realm of financial wisdom and the host of the Mindful Money podcast. Jonathan's journey is a testament to resilience and transformation—from his humble beginnings in a financially constrained family to mastering the art of mindful money management. Together, we dove deep into the intricacies of our shared pasts and how they've shaped our pursuit of not just abundance, but meaningful, value-driven lives. I'm thrilled to share with you Jonathan's remarkable story that is sure to resonate with anyone seeking to chart their own course from scarcity to security.

There's a certain magic that unfolds when storytelling intertwines with financial empowerment, and this episode is rich with both. As a parent and someone who is genuinely empathetic, Jonathan brought to light the delicate dance of instilling the value of money in children without overindulgence. We swapped tales from our banking days and explored how service and inclusivity can redefine success in the finance industry. As Jonathan approaches his 100th episode, I invite you to join us in this celebration of connection and wisdom. Jonathan's insights on democratizing economic security and investing with purpose are not just compelling—they're transformative. Tune in, and let's embark on this journey of mindful finance together.

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Key Takeaways

00:00 Jonathan DeYoe's Finance and Mindful Money Journey

06:08 Parenting and Success in Finance

10:00 Wall Street and Personal Finance Lessons

17:05 Investing Success

28:05 The Evolution of Podcasting

36:59 Gaining Strength, Helping Others

43:31 Celebration of Podcasting and Conversation Journey

Tweetable Quotes

"I was raised without any money, so the thing that you don't have when you grow up is kind of the thing you end up coveting or wanting or desiring."

"Just knowing more about how to invest does not mean you're a more successful investor... Investing is 100% forward-looking. It requires us to either know something about the future, which is impossible... So what can I do? Well, oddly, there's a ton of academic research that tells us what we should do and it's very clear. It's not complex."

"The largest benefit that the advisor provides is behavioral support... The point of that is to provide some calm and to move people out of the amygdala fight-or-flight response into the frontal cortex. Have them think about it, reflect on their plan, realize that, hey, probably the best thing I can do for myself is sit on my hands right now, not do anything, ride this out, this too shall pass."

Resources Mentioned

Jonathan's Email - jonathan@mindful.money

Jonathan's Twitter - https://twitter.com/MindfulMoney_Ed

Jonathan's Instagram - https://www.instagram.com/mindfulmoneyplan/

Jonathan's Facebook - https://www.facebook.com/jonathankdeyoe

Jonathan's Linkedin - https://www.linkedin.com/in/jonathandeyoe/

Jonathan's Website - https://mindful.money/

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Podcast Junkies YouTube: https://www.youtube.com/c/Podcastjunkies/

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Podcast Index, Value4Value & NewPodcastApps: https://podcastindex.org/

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Mentioned in this episode:

The Podosphere

Podcast Blueprint 101

So Jonathan DeYoe, host of the Mindful Money podcast, thank you so much for joining me on podcast junkie.

I'm excited to have this conversation actually.

You're the expert, I'm just in your own. Well, what's interesting is, you are the expert in your domain of expertise and I think what's been exciting to see over the years is how podcast hosts can bring that expertise and share things that have only been accessible either to your clients or your students or your close friends. The work that you do and I think, as we unpack your journey, I want the listener to discover how much is available to you in terms of what's been opening up for you from a network and perspective, even just finding your own voice perspective and I'm sure that's been happening for you over the year. So we'll rewind the clock back a little bit and I want you to share with the listener a little bit of your background in terms of you don't need to give the whole resume, but the short version of if you think about the milestones and the highlights that got you to where you are now. How would you summarize that?

Yeah, I think there's probably three or four good points in time to highlight. I didn't go to school. I mean, I started off in school to study finance but I got bored of it and so I ended up studying philosophy and comparative religion and going to grad school in literally Buddhist studies, did that for three years and then my first wife said, hey, it was her turn to go to school. So I dropped out and I had a degree in philosophy and that was a dropout of a Buddhist studies program. So Wall Street, wall Street made sense. I interviewed for one job at Dean Witter and they hired me and I was a sales, cold collar sales guy for Dean Witter and I spent five years at seven different firms. So I jumped around a little bit.

How does one dropout of a Buddhist school? Is it where you caught smoke in the bedrooms, or is it just a little bit of a dropout?

I needed to work full time to support my wife and so I just I withdrew. And it's an interesting question because they actually make you for me to leave. I had to sign a document that said I wouldn't try to reengage and try to, I wouldn't come back a year later and change my mind. I don't know what it was, I don't remember, I don't have the document, but it was interesting. Exit program.

Yeah, what was it about the world of finance that attracted you? Is it something you were good at? Is it a math proclivity or just curious? What pulled you towards that?

I mean, I think that the way I've explained this in the past is I was raised without any money, so the thing that you don't have when you grow up is kind of the thing you end up coveting or wanting or desiring. So I had this sense that I was never stable financially as a kid, and so I wanted to make sure that I could be stable, and I thought the best place to do that would be where the money is, which is Wall Street.

Yeah, and so how did that manifest when you were younger? Or did you feel that as a need, that there were things that you wanted to do in life or wanted to have in life and you just didn't have access to them, and did that create some sort of longing with you or a way to make sure that you didn't feel this?

in the future. Yeah, longing is a really nice way to put it. I wouldn't say longing, that's very intellectual. Just the best example I love playing soccer. I played soccer my whole life and I would go to soccer practice and literally all of my friends would have the leather Adidas They'd have Nike didn't even have cleats then this is pre-Nike. They had this MITER. Mitre was a brand that everyone had. I had plastic shoes from Payless Payless Shoe Source and I was embarrassing and I was embarrassed by it.

Go to an after school event as a middle schooler. My friends' dads came and they had suits and they had the tie on and my dad came and his overalls and as he worked manufacturing and the car we drove I had, the way the doors closed in the back was there was a rope between the two doors holding them closed. So there was all kinds of things that I wanted and I couldn't have and hey, we can't afford. That was like. That was the phrase that I heard the most often, and on weekends I would sit with my mom and go through the Sunday paper and we cut out the coupons that we would use when we went to the grocery shopping wherever we went grocery shopping and we were couponners before. It was cool. It was because we couldn't afford to eat otherwise. So it's there was a lot I wanted and I had kind of expensive tastes like I wanted to. I wanted nice things and so I started working when I was 12. So I could afford some of my own things and kind of went from there.

Looking back and being a parent yourself, do you see or do you have a different perspective in terms of what your parents must have been feeling or going through during that time, and or have you had conversations about that to just look back at it and see what from a different lens?

Absolutely spent a lot of time talking to my mom and dad about this. My dad was raised, so we had more money when I was growing up than my dad had when he was growing up and we didn't have any money. So I'll just quick story. My dad tells stories about when you're driving along in the middle of the country and you see to the side of the road a gray wood like one or two room shack. Pain is all worn off, there's no windows, the doors hanging off its hinges. The place my dad lived as a kid was they would basically squat in that kind of a place and then they would use cardboard to cut the wind, because we're talking South Dakota, so it's cold and snowy and they would cardboard, cut the wind and they would sleep with the dogs to stay warm.

So I had a lot compared to what my dad had and my kids have grown up with plenty like insane amounts of everything and it's interesting. I think that the reason I have what I have was because I was raised with very little and I create a drive and I maybe want to be successful and maybe want to, and that's the one thing I worry about as a parent. I worry that maybe I have given them too much. My wife would say, jonathan, you have given them too much. I've been trying to ratchet you back, but you know she kind of understands why I do it. But yeah, it's an interesting conundrum Like how do you raise kids? How do you teach them about money? Do you hold back? Do you make them work? But we've done all that. We've made them work and we've held back and they've had chores and all that kind of stuff. But it's a tough question.

Yeah, that story resonates with me as well. I'm the child of immigrants. I was actually born in El Salvador, so I came here when I was a year old. But I'm conscious of that struggle that parents go through and we had, you know, those four siblings. We even had an older sister that passed away when I was two. So there's a lot of, I imagine, trauma going on and I'm feeling that like what your story is really resonating with me, and trying not to get emotional about it because I'm just putting myself back in a situation.

I remember our parents were like we need to buy a home because we were living in an apartment somewhere downtown and we had a little family meeting at the table and for the next whatever it was six months, we were going to be eating rice and beans and tortillas.

And they're like this is what's going to happen, because this is what we need to go to get to that next level. And I even think about the fact that my dad came here when he was in his early 30s. I could never leave this country to go to another country where I don't speak the language and I don't know anybody. And then I think about that and that's sort of what drove the question. Just kind of, even with the mens work that I'm doing now we talk about we see our fathers as this father figure, but when we think about they're just someone in their 30s and if I try to transfer myself to what he was thinking and going through and feeling and struggling with and stressed out about, like I see him in a different light and I feel like all sorts of compassion for him. I see him as a child and as a boy and as a young man, as a teenager, and it really changes the dynamic and puts a lot of things into perspective.

For sure. Yeah, no doubt. And there's an experience I had in high school and I share this with friends and friends all cackle and laugh at this. But my dad, he would get really frustrated with my brother and I and then he would literally walk into the garage and he would open and slam the cabinets. We just hear this crashing and stuff falling around and like he wouldn't hit us, but he would go outside in the carotid like vent. That was so funny, but yeah.

I just imagine what the sense that I can't provide the life I'd like to provide for my family how does that? And that frustration kind of builds and then it's got to go somewhere. So, yeah, it's better for him to do that than smack us around. So I appreciate that.

Yeah, yeah, yeah, yeah. And so, as you are moving into this new direction in your life and working in finance and then seeing that world as well, because I worked in banking I worked the JP Morgan Chase and E-Trade, so I wasn't directly financed, worked in marketing, but I got to see I mean, I started my first job as a bank teller I got to see people like coming in and doing transactions for them. It is a weird situation because on one end, I'm a bank teller but I'm seeing these people depositing these at that time would seem like ungodly amounts of money into their account. I was like who are these people? And like how do they get to be someone like that? You know, and at that point it's probably thousands or tens of thousands and I was like whoa, that's a lot of money.

And so, as you are progressing through this journey, I feel like there's two directions people will take. When they're in finance, they'll just go for it and they just become filthy, rich head-tron managers, you know, and with so much money they don't know what to do with. But it seems like you, and maybe it's because of it seems like it's because of like the original path of Buddhism, and that colored how you viewed the world of finance, but also this idea of making it accessible to more people, and so was it a gradual transition for you. Or did you know when you got into finance or like, and you see that world from the inside, that maybe this is not all it's cut out to be?

I learned like one lesson at every firm I worked and I got to. I could go off, I could go hours on these kinds of things. There's so many funny stories about not funny like horrible stories. Just one quick story.

There's a guy that I worked with the first company I worked for at Dean Witter. He was the golden boy of the San Francisco office. He basically stole a bunch of data from Bank of America when he worked there and he moved to Dean Witter and it became Dean Morgan Stanley, dean Witter very quickly and he took that information, which is basically maturing CDs at V of A and cold, called and into these people and then told them we had CDs or broker sold CDs and he brought their CD money over to Morgan Stanley Dean Witter. And I remember coming on a Saturday, because I worked 15 hours a day, six days a week and I come in on a Saturday, one Saturday, and he never was there, ever like he was never there One Saturday and he was there. All the managers were there, everyone was there and they're all shredding a bunch of documents. A lot of good sign.

And I was like this is juicy and I don't want to be here for this. I don't know what's going on. This is crazy. And what turned out is he was repapering all kinds of accounts, right, he had claimed that all his clients were like other, certain risk tolerance and that didn't match the way they were invested, and so we had to redo all bunch of stuff and didn't get signatures. It was a big night and this is the kind of stuff that you run into all the time.

Yeah, Thanks for that perspective. I think people see movies like the Wolf of Wall Street and they're like is it really like?

that.

And you're like, I've had examples of that as well in the little that I've spent there and I'm like, yeah, there's some of that probably more of that happening than they let on as well. So I'd love for you to share a bit more about the drive for this and your relationship with your brother. You shared this story on your podcast as well. I know it's a top subject, but I think for some context, I really resonate with the mission that you had and that you started with your brother, so I'd love to share a little bit of that with the listeners.

So in I think it was 2012, my brother and I started a separate company called Workers Financial and we were going to basically it was registered to the state of California we were going to try to build tools for, and educational tools and other things for people that were just chicken off, just starting their financial journey, needed to learn something, needed to get savings going, maybe needed to borrow a little bit for a down payment house, whatever. So we wanted to teach people how to do that and then provide them support, coaching and stuff to along to along with that.

So after I merged the firm, I talked to a couple of different people. I ended up starting my podcast about a year later with you and I so much appreciate the help and everything you guys have given. I started writing. I have this weekly newsletter. I've been doing for 15 years. For the first early years, I was pretty canned and I started writing all of that myself. I published my first book and my second book. I'm working on the third book and I've got the fourth and the fifth lined up already. So basically I'm trying to create information, education and really psychological support for people to get to better outcomes without needing to have a million dollars to start, like without needing to qualify for advisors or advice, and so we've had coaching programs, we've got a boot camp, we've got all that kind of stuff for that. But it's really how do I take this thing that my brother and I want to do together without the technical skill set and get it in front of more people and really help people out? Thanks for sharing that story.

I know we're probably sharing it a couple of times, maybe more since all the other shows, and I know it could be a podcast, but it's helpful, I think, to provide some context in terms of you talk about the mission and even talking about your back history, about how you're wanting to help people, because it does, having been through that system, the banking system, the money system it's really foreign to so many people and they feel like it's out of their reach. It's not something that's something the wealthy people do, or that's something rich people do and not coming growing up myself as not having those opportunities, you feel awkward in situations where that's being discussed or the little people tell you about savings, or you feel like what am I going to save if I don't even have enough coming in? And you talk about the psychological support that you specifically mentioned. Why use that phrase? I'm curious about that, because is it really a mix of not just the actual book smarts to do what needs to get done? I'm curious why you consider there's a psychological aspect to it as well.

I mean, finance is interesting because finance is like it's the one thing that I know of where the smarter person doesn't win. Just knowing more about how to invest does not mean you're a more successful investor. I know everything Like I've read all the books, I've read the academic studies I've read, but that doesn't give me any insight into what happens next, because investing is 100%, it's forward looking. It requires us to either know something about the future, which is impossible, which nobody knows, anything about the future. There are no facts about the future. I don't want the next pandemic hits. I don't know if we're going to have a world war. I don't know who's going to be like the president. I can't know any of these things, so I can't really make investment policy out of chaos theory. I can't do that. So what can I do? Well, oddly, there's a ton of academic research that tells us what we should do and it's very clear. It's not complex. You do very simple things. There's three things. There's only three things that actually lead to great financial outcomes. Right One you already touched on this one You've got to earn some money.

You have to earn money. You have to invest as much of the money that you earn as possible. You have to invest as much money as you earn as possible in equities. In equity whether it's your own business or a real estate or whatever, in ownership. That's it. Those are the three things. The first part, earning that's I've got to become better, I've got to be a better employee. I've got to earn the raise. I've got to deserve a higher income. I've got to hustle to create a second income. I got to. That's something that some intellect, but it's mostly psychology and action. Right, the idea of saving or investing a percentage, that's also a choice.

People say, oh, I don't make enough, I can't save. Listen, I know people that come into this country for the first time. They'll have eight people to a room so that they can save A guy. An Uber driver picked me up from the airport in New York and drive me to my hotel. He said we had this great conversation. It was a 30-minute drive. He was like, yeah, I got to get the car back to my cousin. My cousin's going to take the car. He's got the next Uber shift. I'm like, oh, your cousin, you live in the same place. Yeah, we all live in the same place. There's six of us. We live in the same room I live in my uncle's house. There's 12 people in the place. It's a two-bedroom place. We're saving money so that we can get another car, so we have another Uber driver. That's all the time. We're starting another business.

You make choices that enable you to save and invest in something I feel for people that don't feel like they have a choice, but they have a choice. They have a choice. It can be hard, but there's a choice. That's psychology. Then the last thing is that I've written about this for the last two months on a very steady clip every single week, like 10 pages a week it's been. I've gotten more feedback on this writing than I've ever gotten. I'm finally kind of coming into my own and being honest about this.

I love equities. I'm a zealot. There is no better passive investment on earth and people are afraid of them and they're worried about the volatility and that all becomes. That's all psychology, because if you look back at any 20-year period, the worst 20-year period in the last 100 years is a 6% positive return. But if you look at it day to day, any day I might lose 4%. I could lose 6% tomorrow, I could lose 40%, 50% next year, but the average annual return over that 20-year worst period is 6% average annual.

So I mean, it's just, you get bogged down in the details and you get worried about the current gathering, darkness and the news headlines, and that's psychology. So by introducing psychology and this is where that mindfulness comes in the fear of the thing that might happen, where the fear that's expressed in the headlines which, by the way, those headlines are intentionally designed to create fear that's how they write the headlines. How do I make people more afraid so they click on my stuff more often? That's what that's about. So if you get over the psychology and your mindfulness can keep you from making bad choices, then I can do lots of good that way, and I don't have to do it one-on-one.

I can do lots of good for lots of people in a group setting, because we're not talking about your finances, we're talking about psychology, our, I think, what's been interesting for me is also seeing some of your recent writings and you did mention that, something that's changed for you recently and most people think well, I'm a podcaster. I started podcasting because I didn't really like writing back in 2014. I thought I'm just going to talk because there's writers that write. I just like talking and getting my conversation from other people. So I'm in. A big part of what I do is feeding off to my guests as well. But I've noticed recently myself I'm trying to be consistent with my Saturday newsletter as well. How have you seen that that shift has either complimented what you're doing from the podcast perspective or helped you have this more long form way to teach the things you talked about? The coming dark. The series is called the Gathering Darkness Gathering Darkness.

So how has?

that opened up for you this ability to cut to in your mind. I think how you put it was like speak what you've been meaning to say or what's been in your heart for a long time.

Actually. So I've been writing every day for 20 years Like I can't help but write. It is how I think, and so part of it is maybe in the last couple of months I've clarified my thinking and so I've been able to and the comments I'm getting are Jonathan, I've never heard it put this way. This makes so much sense. I can now engage equities more easily, and that's heartening. That makes me feel good and that's what I want to do. So I'm taking, I'm trying to take those last eight weeks and package them in a different way, because huge positive response from the public, from my clients, from the subscribers of the newsletter Obviously that does great work.

I've been trying to do this. I've been saying the same thing for 25 years, but I get response for this, so this needs to be the core of something. So I got to. Maybe it's the next book. I don't know what it's going to be. There's a lot of stuff there. Yeah, just, I've been very successful for 25 years basically focusing on. I've tried every kind of investment, no demand, but the one that's worked consistently throughout every cycle is owning great companies. I'm just trying to help people own great companies. You can be the brand new investor. You can have $100 and you can own great companies without $100, but you got to commit to it, you got to hold it, you got to stick with it. When you have another hundred bucks, you got to add to it. This is how this works.

That's how you do it and I was going to ask you the next question. Like, when people are just getting started, they always feel like I don't have enough. I don't have a thousand dollars, I don't have $10,000. But I think what you just said is that it's really the mindset to decide that this is the path you want to take and then to start. It sounds like you can start with $100 or $500. And obviously it's not going to be a ton of companies, but maybe and we'll provide the links to your program so maybe you could talk a little bit about that, because I want people to know that it's something that I'm actually considering joining myself for the record, because I've been just reading the notes over the past couple of weeks, I'm like I should probably be in this. But talk a little bit about what you're putting together to make it more accessible.

Yeah, so I actually come January this is going to anyone in a content creation world we iterate, like we have to iterate to figure it out right. So we're actually shifting January, maybe February, to it's going to be 100% membership-based and all the stuff that I do is going to go into the membership. And really the question is going to be if you're a full member, there's going to be three tiers. The largest tier is going to also have an hour conversation with me one-on-one. The middle tier is going to have access to everything in the live group. The lowest tier is going to have everything from video. Really, it's the same information. It's just going to be which package do you get? You had an original part of the question that I want to answer.

Just talk a little bit about how people think this is only accessible to people who can work with a financial professional. Yeah, so just yeah, oh yeah.

Yeah, I mean, the basic, simple rules are just so easy to do and so I can do and I have clients that I've done really, really, really deep, forensic financial planning where we look at every single detail in their lives. When I look at all those that I've done, you can pull out there's like seven main things that you do and there's sort of an order of operations to finance. First you get out of your high interest debt, then you build your emergency fund, then you start saving in your retirement program, then you maybe save either more in the retirement program or you pay off your low interest debt. So there's really some very basic, simple, step-by-step processes you can apply. That means you don't have to do a very, very deep financial plan and most people don't really need. Our financial lives are very similar In reality.

If you've got a job and you get a paycheck, that paycheck has to go to pay for some stuff that you spend money on your rent, your food, your cell phone plan, your car and then you got some leftover. Well, we got to flip that. Maybe we should save some first right and then spend the stuff on the other things. Maybe you should know what you should need to save. So that requires a small calculation. But I have a simple spreadsheet that I share with people and how they can do that themselves. So it can be really simple for the basics and, I would guess, 90% of people. It's just the basics, it's really just the basics.

The thing and this is Vanguard's research says this, morningstar's research says this and this is we do this once a month. The thing that an advisor, the largest benefit that the advisor provides is behavioral support. That's the psychology. So once a month we have a session. We call it ignore the noise and I'll present the current noise. This is what people are saying in the media. This is why that probably doesn't matter in the long term. This is why they're presenting it right. The new data came out and this is what it is, and they can get you to pull this lever and maybe change to their portfolio and maybe get worried about stuff.

So we talk about everything once a month and then when the world goes haywire which it hasn't in the last six, eight months, but when it goes haywire we have some special sessions. I'll touch on those things, right? They'll say, hey, let's do this on next Thursday at four o'clock. We're going to have this conversation because people are scared. The point of that isn't that we're going to do anything differently. The point of that is to provide some calm and to move people out of the amygdala fight-or-flight response into the frontal cortex. Have them think about it, reflect on their plan, realize that, hey, probably the best thing I can do for myself is sit on my hands right now, not do anything, ride this out, this too shall pass.

The world tells us. This time is different. We respond with nah, this too shall pass. And that we do that over and over, and, over and over again, because it's like vitamin C. We need a vitamin C every day, but every day we need more vitamin C. We pee it out, it doesn't stay, so we need more vitamin C. So this is that. This is financial psychology. It's a vitamin C for our wealth development.

I'm going to just title this episode Thanks, that's great. Yeah, thanks for sharing that. We'll make sure for the listener, for the viewer, that we have the link for that program in the show notes as well, because I think it's highly valuable. So, shifting over to the world of podcasting I know you talked about us getting started working together. I'm wondering if you can think back to that first nudge that you felt. Were you listening to them? Were you watching them videos? Or did you just feel this pull to like I got something to say and I think it's about time.

So my development of podcasting was sort of three steps. The first step was I published my first book and so my publisher said, hey, we should get on as many podcasts as we can be on. This was 2017. We should get as many podcasts as we can, and I was on like 100 podcasts and maybe 110 podcasts in a year, which was super fun. I just talking to people and had a great time.

But it was kind of slow moving. It wasn't specific to the thing I wanted to do with the audience for education wise. It was very big picture. It wasn't granular enough. It wasn't decisions on the ground. How can I help people? It was like, how can I help society, but I don't have any pole there, like I can't really change society. I can change things for one person, one at a time. So I said, hey, I need to do this other thing. And then I just started researching, cause you know me, like who can handle the technology, cause I can handle the technology, I can talk to people. I love talking to people, but I can't do any of the tech stuff. So I started looking at people and I found you guys and podcast junkies and I was like, hey, how do we do this? So can you help me set?

it. I know, in the beginning, you know we were talking about getting set up with your first guests and you had a dream list, you know, dream 100 or wherever it was that list of people you want to speak to, and there's some heavy haters or people that you admired in the space and I imagine I think we talked about it a little bit like a little bit of apprehension, like, oh, I'm gonna have this call schedule with this guy and I really admire him. And I'm curious, those first interviews, if you could talk a little bit about what you were feeling going in. And then, once you had it and once you saw what the flow was like and that you know you got a couple of them recorded Did you notice a shift in how you were feeling as a first time host?

So I kind of I mean my first guest was probably the heaviest hitter guest I've had to date Like I went straight for the and I used the story Like the point of this podcast is to help people out in the way that my brother and I would have been able to get together without my brother and he was like yeah, let's do this. And we had this great conversation and I've been reading his stuff and listening to him for I don't know 30 years and so he was like a guru to me and so I was really happy to have him on and he was totally gracious. He actually said he'd come on again. So yeah, he was awesome. But then I kind of went, you know, I was like oh, that was kind of nerve wracking.

So I went kind of to some local people, some people I knew, some people that would definitely say yes, and I have found I was always worried about getting the next guest and occasionally you don't have enough in the can. So you're like I got to get someone on here, right. And so I said now I have a process Like every other Monday I send up five invites and usually I got one or two people respond, you know. So it's like a pretty consistent process now. But once you build a process around it, I can talk to anybody. Like I can talk to Biden if you'd be on there and it would be fine with me, like I wouldn't be afraid of that. Like I can talk to anybody, ask them questions, do a little bit of research, figure out two or three really good topics that we could dig into and the conversation just happens Cause, just like you, I'm a conversation I like having conversations.

You mentioned the hundreds of shows you had been on as a guest. How did the dynamic change when you're in the other side of the microphone as the host, because you have to control the conversation right? I'm conscious of it always when I'm speaking to people and I'm making sure we're having a flow, there's no awkward breaks, that I'm having follow up questions ready, that I'm staying connected, I'm maintaining that sense of curiosity, but it's an active thing that I'm doing as a host and I notice it. When I'm a guest I'm more relaxed, but also the host mindset. I'm just like you could have asked a follow up question or you could have. There's a little bit of silence here, like should I jump in and it's like I don't want to take over someone's show. So I'm curious how you started to develop that skill as a host, which is a bit different than just showing up as a guest on a show. I think the hardest thing is as a guest.

You're supposed to talk Like you're supposed to offer complete answers and you're supposed to be that. I mean, you ask good questions and I answer those questions, but usually I don't know what the percentage is, but 75%, 80% of the talking is from the guest, right? So the shift as a host is shutting up. That's the hardest part, right? The hardest part is not driving the conversation in time. For me, that's the hardest part. It's not driving the conversation, it's asking a question and then teasing out more answer and they close and you're like, okay, well, let's get a little bit deeper on that. What about this element of that? Or what did your dad say about that? Or I just tease out a little bit more and just get them to keep talking. But usually more people like to talk, so it's not that much of a problem.

Shutting up is hard. You can see it and I referenced it from an editing perspective back in the day. You would see the two files. You see the host and you see the guest and you see the way file and when the way file of the host is bigger than the way file of the guest, you already know like the host is talking too much. You can see it in the visual representation and it's to your point.

Being comfortable with silence, I think has been a big one because you just you want to jump in and you feel like there's an awkward moment, and video has made this easier, as you can see people's reaction.

You can see they got their finger to their head, they're looking up, they're like thinking about should I give them the politically correct answer? Should I give them the answer from the heart? And I think what I've found is that ability to break the ice in that first five to 10, 15 minutes is really crucial because as you progress through the conversation you'll want to probe a little deeper and I think it's surprising to see how much of a connection you can build with someone in an hour-long conversation. But if done correctly, you know, what I've discovered is that you can get people to open up and I think most people are just dying for like good conversation and trying to connect and they want to share their story and they have a voice inside them that needs to be heard and I think it's a skill when I've seen it done well that a host can bring that out gradually in a safe way for their guests.

Yeah, I think that I get better at it with every episode. I think in the very beginning didn't know what I was doing, which is, you know, I think that's fine. Like this is the whole thing we become. Like we have to be willing to let go of our old selves to create our new selves. That's how we learn, that's how we get better. So I think I'm approaching 100 episodes. So by my 500th episode I'll be good yeah.

I love so much. Have you refined your dream list now? Do you have a couple new names on there?

Oh, yeah, yeah, I have a bunch of names on there and they will respond to me. They won't say yes just yet, but I will.

Yeah, I've heard of some hosts when they start, you know, swinging for the bigger names, there's probably five to 10, 20 different like either no answers or rejections. But there you can see, and people describe it like, yeah, you just have to be persistent and continue asking and it could be a couple of years, but eventually you know, this year, show, grow your visibility to grow and they'll be like, oh, yes. And then you'll send back that original message from three years ago like, yes, this is what I originally asked you, so thanks for coming on right now.

But you do notice it as a host.

Yeah, yeah.

I'm curious, like that you've gotten better and more comfortable in your skin as you're having these conversations.

Yeah for sure, yeah, yeah, yeah. I mean I still prepare for every single one, like I still, you know, I read the book or I look up the persons what they're doing. I see some of the other interviews that have been on and I do this for every interview and I wanna do this for every interview because I wanna make sure that every I wanna be in the space that they're most comfortable playing in. I don't wanna ask them any zingers, and occasionally I still ask them a zinger. Occasionally I'll be like wow, that seems. I was on with Spencer Sherman recently and he said something that I was like nah, I don't think you're right on that. I was like no, no, I think there are people that could reasonably give up an eye for a billion dollars. Like I think that's, you know, I think I would. I would be one of the ones. He was like no one would ever do that. I'm like, no, you know, there's a price for an eye. Like I think that people would. Anyway, that's a good one.

No, but I think it's just a function of being comfortable in your own skin and being comfortable that you are directing the conversation and that you're controlling the flow of it. And that's the responsibility that you have to your audience and to your listeners, because they're counting on you to share. Bring in these guests that they don't, that they wouldn't have had access to, but also they're coming in for your insight. And what's your take on this guest and what can you get out of this guest? And I think that's fascinating to always think about. I always keep harping on about the three people in the conversation the host, the guest and the listener and try not to be excited about it, because without them we don't have a show. That's right.

I have a couple of questions that I always ask my guests as we get close to the end. The first is what's something that you've changed your mind about recently?

There's always a nice little pause when I ask that same question, the thing I've changed my mind about recently, trying to go back. It's interesting because it's there's the big things and I want to actually come up with a big thing that I've changed my mind about recently, but there isn't really a big thing, it's little things Like, so this maybe gets into things.

So my brother died two years ago. So if all the holidays for the last couple of years we've hosted at our house and we've invited his family to come to the house, and this year for the first time, I'm like you know what, judy, how about you host this year? We'll help, we'll be there, whatever. But let's bring some cheer to your house, let's not happen all at our house, let's go to your house. And you know she said yeah, let's do it. So I was like all right, cool, we'll make it as easy as possible for you. Like we'll be there, my parents will be there. So we'll make it as easy as possible, but not just always solving the problem and not just always just allowing, allowing some of the joy to go that way.

Well, prompts another question for me what sources do you draw from to have this? What I sense is like this sense of that there's goodness in the world and that there's people that need, always need support and feel like you always do whatever you have in your capacity to do to help people whenever you see that there's an ability to do so. And sometimes, you know, we all are going through our own personal challenges as well. So I'm curious if anything comes up for you when I ask you know where do you draw from to get that strength to make those calls and to provide that energy? Because it requires some more of you. You know, and you may be going through your own things as well, so I'm pretty sure what resonates for you when you think about that.

Well, so I've lived an incredibly blessed life. I've always been super optimistic. My dad was super optimistic. I used to a client would lose a loved one and I did all the things that would be supportive of the client who lost a loved one. They have flowers and send an email, and send them a text, and send them. Just love on them a little bit right. And then I lost a loved one, and no texts or flowers or anything changes anything about that. They're all nice gestures, they're all beautiful things.

I had one client and this is two or two and a half years later. I had one client who, for like the first seven or eight months, would send me she walks her dog around Berkeley and she would send me a photo of something that looks like a heart with her dog sitting next to it. Every day, every other day, for months and months and months and months. And then it became every two days and it became every three days. It was once a week. I just yesterday got another one, like two and a half years later. So this is someone who is going through her own family struggles. She's got her own stuff and she said right out of the gate, you don't have to respond anyways. I'm just showing you love, like I'm just showing you that people are here and they care about you, which I can get through a conversation about losing my brother. But when I think about that I'm like that is amazing. So I think she draws on not a religious background, but she just draws on this the desire to be a good neighbor, the desire to be a good person. I think my dad and my mom really said you got to be a good person and I got that.

I was raised Christian and I went to church and I wouldn't call myself Christian I mean, I've been baptized and all that kind of stuff catechism but what I learned was you got to love your neighbor. You got to be vulnerable to difficulty and I didn't really understand that until I lost my brother and so I was always very optimistic and very positive and very upbeat and I would get to step out. I was a guy that helped, that I could do all these things, but I never needed help and I didn't want help and I didn't want to until I lost my brother and then I learned the other side and it took me probably six weeks to actually say to somebody I need help, like I'm really not going to, I cannot do this myself. And in doing that I got help and I saw the benefits of that. And so now I kind of dropped from history of optimism and I dropped from the experience of needing and just if I can do something to help, I'll help. Like that's and the experience of those people who stepped up.

I had a buddy who met me outside my front door every day for I don't know three or four months and we just went for a walk in the park together. Like it's 6am dark, cold, 6am walk every single day, because he had a good work Right, and I had to go to work. So, and people step up and so I want to. I don't ever want to not be that person. I want to step up and I have never done as awesome things as they've done. Like I'm there, I can be helpful, I want to help people, but people have shown me the way, so I try to be better.

That's incredible, inspiring. They put your shirt in that. I'm glad I asked what is the most misunderstood thing about you?

So I'm six foot five. I weigh 220. I'm strong, I'm fast, I'm athletic. I seem to be pretty outgoing and various. I'm not. I'm a very sensitive, vulnerable, easily affected person and sometimes, yeah, I wear my heart on my sleeve and it gets crushed like it does, and that's you look at me and people don't think that. But yeah that's the thing that people miss.

And I think it's a thing that a lot of people miss in their outward perception of others, and I feel like I'm a similar. So because of it I'm sensitive to faults. Sometimes I'm like a little too much, and you know my partner keeps me checking. She's like, you know we got to balance this out a little bit so but it's I think, about everything that's conditioned me family stuff, life stuff. You know everything that's gotten me to this point now.

So and I don't want to be defined by my past, and so I'm glad you share that, because I think it's also a reminder that we can be that way, but also we can also function in this world in a way that allows us to contribute the best of our abilities to make the world a better place. So I appreciate sharing that.

Yes, I know that I don't know if this is a quote I hear all the time, but it's so true. It's like be yourself. Everyone else has already taken right. It's be your authentic truce up. I can't imagine how awful would it be to pretend you're somebody else, pretend you wanted other things and then be really, really successful at that. That would suck, like you would end up. I would rather be myself and have it my own skin, be honest, be authentic and fail than try to be something I'm not and get really successful Like. I just can't think that that would be fun.

Doesn't sound miserable. Oh, that's right. Well, tom, thank you so much. I was really looking forward to this conversation, just from watching your journey and you evolve as a podcaster, a podcast host, and seeing how much excitement you get from having these conversations and building these connections with your guests.

Closing in on 100 is no small feat. So I just want to publicly thank you for being consistent, because that's the biggest challenge. People they call it the pod fade. You get to seven. You're like whoa, this is like a bit more than I expected and I think it's getting over that hump and then seeing and having that vision to see that you are making a change, because people are hearing you directly talk about the things that you're passionate about and that resonates with people and I think I imagine it's something, some of what you're experiencing by having these conversations the feedback you're getting not only from you later but from the podcast itself and even from your guests.

So again, I applaud you for your consistency and I'm looking forward to your hundredth and your 500th after that, because I think you'll see just how that journey evolves is really exciting. So I appreciate you for being vulnerable to appreciate your story. I know some of them. Sometimes it's challenging, but I think it's helpful for the audience to hear different perspectives and also a reminder that we're all on similar paths and we're going through similar challenges of different varieties. But I think conversations like this are important for people to hear and be inspired by.

Yeah, Harry, thanks for having me on. I always love having a conversation with you. It's been great.

Where's the best place for folks to?

connect with you. Mindfulmoney. All the socials are there. They're nocom, it's just mindfulmoney.

Okay, we'll make sure we have all those links and the program you mentioned in this show, and us as well, for people can learn more. Thanks again, jonathan, I appreciate it. What the heck Yeahami?