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How To Become Financially Happy with Wes Moss

We are talking to Wes Moss. If you're getting to know him, Forbes named him one of the Top 10 Best in State Wealth Advisors and Barron's named him one of America's Top 100 Independent Wealth Advisors.

What's fascinating in this episode is the data that Wes put together surveying families in over 46 states in the United States to put together a book that he put out and it was interesting because the whole topic is around retirement and happiness. We talk a little bit about the book and what makes people happy, how you can get to retirement a whole lot sooner than a lot of the big-name gurus, media personalities and big banks are leading you to believe.

In addition, we talk about what happens in Trump Tower, 2004 on The Apprentice. Wes competed on the show. We talk a little bit about that if you're looking for a great interesting story. Do you want to know what is it that buys happiness? Is it money? How much money? What do you need to do? What things do you need to be in place for you to be happy when you retire? Maybe you don't want to retire. We talk about that too.

Wes, it's 2004. You're in Trump Tower and you're about to film The Apprentice. Essentially, not your boss but three levels up from your boss from the institution of UBS is on the phone with you and simply says to you, "I'm not sure. We can't approve it." That changes directions for you. Will you tell us a little bit about what happened?
Wes
If you go all the way back to 2004, reality television shows were still pretty nascent and especially for somebody from what was supposed to be a hoity-toity financial institution. UBS is still a giant global bank and investment firm. The last thing they wanted one of their advisors to do is go on some reality show, particularly with Donald Trump. Obviously, they didn't know he was going to be the president more than a decade later. It probably was the very height of that because the first season was one of the largest reality shows of all-time ratings-wise. It was 18.5 million people average per episode. The second season usually gets a bump from there. It was in the interim between the first season and the second. I'm ready to go. I'm in Trump Tower. It went all the way up to the top of the food chain. The president says, "This is something we cannot approve you to do." I sat there sweating and very nervous. Ultimately said, "I know you're not going to sanction this, but as long as you're not going to fire me, I'm going to go ahead and do it anyway. I'm going to roll the dice."
Dustin
Take us through what happens after you rolled the dice.
Wes
Ironically, even now looking back on it, it was probably half luck, half naivety. There were several people on my show that was fired due to the show. It's because on reality television you can be painted in an even worse light than you already are. Particularly if you're on a show at the time was must-see TV on Thursday night on NBC. People will watch it. If you said something wrong, you offended somebody, your employer the next day said, "You're out of here." That happened to several people in my season. A lot of contestants on The Apprentice over the years have lost their jobs because companies are like, "You didn't represent us well. You're gone." Particularly these big investment firms. I get this because I have an investment firm. If you've got 10,000 financial advisors, you’ve got to have a strict set of rules for all of them to follow. You can't have rogue people doing twenty different things in the media potentially harming your brand. Their answer is always, “No.” Quite frankly, this scenario says, "You can't go do this," was the minute in my mind I realized I have to leave this place. I'm not going to leave it now, but I've got to get out of here and start my own company.
Dustin
When you were auditioning for the show, when you were thinking about it, was your mindset like, "I'm going to do this because it sounds fun and exciting?" Were you thinking, "I'll get a ton of business out of this?" Was it a mixture of the two? What was the mindset going on there?
Wes
It was the adventure of it. It's like, “I want to go climb Machu Picchu. I want to go to Nepal. I want to go to Moscow for the adventure.” I knew deep down as long as I didn't make a fool out of myself and I think in retrospect, I would have maybe even been more nervous now knowing how many ways you can mess it up. In my gut I said, "Some way, shape or form this can translate to something positive." That's why I was adamant that I would do it.
Dustin
It's important in life you have these moments that make you question everything. In your particular case you said, "I’ve got to get out of here." You can't have someone making those decisions for you. You went to go build your own firm. Talk us a little bit about that transition. Eventually, you would go to leave and having the gumption to go start your own thing.
Wes
One thing that The Apprentice taught me is the power of media. I don't think anybody questions that now. You have a wonderful podcast that's popular. I've been doing radio for a decade. Coming from a farm, growing up in rural Pennsylvanian Amish country, I went to the University of North Carolina and majored in economics, but I still was pretty naive when I was first in the business world. It was that experience to open my eyes up to media and being able to understand public relations and all those things that I learned quickly. I'm a big believer in writing and creating content. That's when I started to realize that I wanted to do that. In a big firm, in a big global investment bank, you can't do it.
What that put in motion as I've got to at some point figure out a way to be able to go independent and leave a big-name firm, which was not a very popular trend in 2004. Not a lot of people left big firms to go start small independent firms. Ultimately, that's what I realized I needed to do because I was adamant about doing my own writing, my own video, my own audio. Part of that was from learning about that through the show. I wrote a book after The Apprentice about entrepreneurship. Ironically, I wasn't even an entrepreneur but I interviewed a bunch of entrepreneurs. The book did fairly well. That let me get my foot in the door to do my first radio show, which was about the topic that I do for a living, which was about investing. I wanted to do it. I started that in my late twenties and I've been doing it ever since, which has been impactful on my career.
Dustin
Wes, I want to talk a little bit about it. This ability to write, to be a communicator, every entrepreneur needs to be able to do that. What I'm most interested get into is a lot of the research that you did. I'm interested in the timeline. You did the radio show and then you get this idea for a book, I presume, and you go and you do a ton of research to create the fodder. How much of the radio show was an impact on the book?
Wes
The first book did pretty well about entrepreneurship. The second book was forced. It still took up a lot of time. It was called Make More, Worry Less and it came out right as the financial crisis was hitting, when everyone was making less and worrying more. It was dead on arrival. The topic didn't resonate with folks at the time. It made me say, "I'm never going to write a book again," because it's hard to sell any financial book. There are literally a million of them. It's hard to get any traction. I said, "I'm not going to do any book at all." I shut it out of my mind for a lot of years. What it was is shutting that idea out. Opened me up to say, “The only thing that's going to change my mind is if I think I have a unique winning idea.”
I think I was shaving one morning. I had one or two children. There was a popular book called The Happiest Baby On The Block. It made me think of retirees a little bit. It made me think of, “What if I did a book that is about the happiest retiree on the block? What did that guy do? What did that couple do that all the other unhappy retirees didn't do?” I said, "Let me start with a survey and a research project," not a book because they were getting still in my head, "I'm still not doing a book," but I'm going to do a research project because I'm still fine on writing articles. I was still fine to put out new content to be a thought leader. The survey I did, which was at the time through SurveyMonkey, which allowed getting out there and getting a huge amount of data, 46 states, 1,350 families did the survey.
I asked a series of questions of consumer habits, financial habits, where people shop, what people drive, how many vacations they take. How they live their life financially and through what they love to do it from an experiential standpoint. I also asked a series of these questions that were able to segment the happy group and the unhappy group and then compare those two. The data of that research came back interesting. I said, "This is a book. This is fascinating," because I'm going through the data, I'm like, "This is cool. This is interesting." That's why I embarked on this book project and I think the thesis of it became how much money does it take to be happy?
Dustin
Wes, you've got us hanging here. I know that people should go out to get the book to get the insights and truly ingrain into what they're doing. Can you give us a little taste of some of the interesting things that you found with the happy folks? We shall learn from the unhappy too.
Wes
The overarching premise here was that can money buy happiness? There's an empirical answer here is yes, it does, which I don't think anybody's falling out of their seat to hear that. In a non-shallow way, I feel as though I've answered the question more empirically. The answer is yes, it does buy happiness but only up to a point. One thing I was able to graph in this book and I asked them, "What were your peak earning years before you retired or what is your peak earning years were? How much have you saved for retirement? Liquid money. All of these financial questions that allowed me to graphically try to understand what money lead towards happiness and when it started to effectively no longer add to happiness.
An early theme at the beginning of the book is that wealth, let’s call it money and happiness, creates a very distinct plateau effect. If you graphically look at this, you're able to see that at the early stages of either making more money or saving more money, there's a huge jump in happiness in those early stages. When we get to a certain point, this important inflection point in America. I say in America because barring some of the most expensive cities costs around the same to live in 95% of America, barring Palo Alto and maybe downtown Manhattan. We've got to get to a certain income to get to that happiness level. We've got to get to a certain retirement savings level to hit that happiness inflection point. The next part of it, and this is something that is important about the book too, is that it's counter to what Wall Street wants you to hear.
If you think about it, let's go back to UBS where I used to be or any of these big insurance firms or financial firms. These are publicly traded companies. They want to grow their asset base year-over-year no matter what. If you get to a certain point, that's enough. That's why you'll see articles that will say, “New studies show that you need at least $2.6 million to retire. Sponsored by The Hartford.” I've seen articles that say now you need $3 million. In fact, Suze Orman came out and said you need $5 million to $10 million in order to retire. To me, that shuts a lot of people down. It says, "I'm not going to even try." Your readers are more entrepreneurial and they're in real estate and their investors. They probably think of, "I need to get a couple of million dollars to feel good about it."
This is one of many bullet points in the book or one of the inflection points. Most of America, you’ve got to get to about $500,000, which is the median number, median net worth where I see people crossover from the unhappy group to the happy group. That's one of the metrics within the book that has to do with what do I have to get from a liquid net worth perspective in order to hit that happiness level. Maybe happiness isn't the right word. Maybe it's peace of mind. Maybe it's financial security. Whatever that is, but the book lays out all these different pieces of how do I get to this happy place that doesn't necessarily need to be $10 million. It's much more attainable than what a lot of Wall Street will make you believe.
Dustin
They say that the journey of saving and working is often where people get the most joy. They might not say it at that moment. When they look back, they think back of all that. Does your research show any of that? Once someone has reached it, do they get unhappy a little bit?
Wes
I spend a lot of time in the book on this. You've got to have a tremendous amount of purpose. I call these core pursuits in the book. Once you hit your magical financial number because you've got to have some economic, financial and intellectual stimulation once you've stopped working. You will quickly get bored. It’s because you have enough money if you don't have enough to do it's not a lot of fun. I had a good friend of mine test out retirement in his early 40s because he has plenty of money. It didn't work well because he didn't have a ton of different things he wanted to do. He started to miss the stimulation of work, being challenged, and the interaction with all the folks that he was working with.
It's the same thing if you're 62. The problem when you're 62 is that most of those people don't have the opportunity to go back into the work world if you're not already an entrepreneur. If you've worked for two different companies, let's say you’re fifteen years at one and twenty at another. You've got 35 years in Corporate America and you're out by 62. A lot of folks in America are having a real tough time finding another job that pays even close to what they used to make. We're in Coca-Cola territory here, Atlanta headquarters. I'm not going to pick on Coca-Cola here, but I can tell you if I did identify one trait, I've seen this year, one circumstance. Coke is relentlessly getting rid of people the minute they hit 55. They've totally restructured this giant company to say, “We want only a few people at the top, no more middle management, and a whole bunch of people working down here on this level.” They're eliminating this massive amount of people in any middle management.
When you're 55, you're out of there. You either have to have a lot of things you want to keep doing in your life and be ready for early retirement. You might not even be able to get another job even close to your salary. When it comes to planning for your life, once you get plenty of money, you've got to think about it because whether you hit $500,000, which is one of the criteria in my book you've got to get to. A paid-off mortgage is number two. Does it mean paid off real estate? Rental income is another part of the formula to be able to stop working at your day job. In the book I labeled this as you've got to have 3.6 of these, I call them core pursuits, which are hobbies on steroids. If you don't have 3.6 hobbies on steroids, you're in bad shape. That was a big difference between the happy group and the unhappy group. They have a hugely different number of different things they absolutely lived to do.
Dustin
There's a conversation of happiness and also the book titled, You Can Retire Sooner Than You Think. How do those work out in the book? I see them as two different thoughts.
Wes
First of all, what ultimately happened here is that this originally was a study of happy versus unhappy folks and comparing the financial habits of the happy group and the unhappy group. Ultimately, the happy group ends up being able to retire sooner. They've hit these certain checkpoints and none of them in their self are hard to get to. You have to do all of them in order to have a framework or a foundation where you're able to then stop working at XYZ job. It's the happy group and those financial habits that they get to a point of early retirement sooner than most of America. When I originally went into the book thinking, “If you're 62 and you can stop working in America, you're way ahead of the curve. You're in the top maybe not 1% of folks, but you're in the top 10% of people from a net worth perspective in America.” That was my original thought.
Over the years though since I published Retire Sooner, I've had a steady stream of younger and younger folks call me and say, "Wes, I'm 59. I'm ready to stop working. Let's walk through the numbers. Can you help me do this? Wes, I'm 54 and I'm ready to stop working." I wrote the book to say, "If you're 60, you're lucky to retire that early. That's still early.” It's been a good decade for the economy and stocks quite frankly and real estate. I see more and more people that have built an income stream or multiple streams of income. Whether it's publicly traded equities, whether it's rental properties or putting all those pieces of income together, they’re the ones that are able to stop working early.
Dustin
From a tactical standpoint of being happy and retiring early, what would you say the steps are to be either one of those or both of those? What would you say tactically those are?
Wes
Number one, what are the pure financial steps? First of all, remember that it's still a rare group of Americans. Let's call it 10% of people. They are lucky to ever be able to get there because it's a long journey. I've done some additional research to show the sheer amount of time. You've got to start either saving early. You've got to start your entrepreneurial journey as early as you can. It starts with starting as early in the process as you can get going. That's the first piece of the equation for people in real life who are able to get here. It's tough to start when you're 60. It's a lot easier to start when you're 25.
The next part of this is that I'm a big believer in these core pursuits. Even though that has nothing to do with your finances, it is a real step that psychologically drives you. If you've got three to five things that define you, it drives you financially to be able to have the independence to do those things in the future. They become a self-fulfilling prophecy. The core pursuits are not, "I love to go hiking or biking or running." You’ve got to have a sense of, "Once I have economic freedom, these are the things that I'm going to go do." You can't just start them once you get a bunch of money, that's another problem in America. I see entrepreneurs do this all the time.
Their entire life is work. They hit 55, they hit 65, 70 and they stop working. They have plenty of money and they have no idea what to do with it and it. At that stage, what's the point? The next thought here is you've got to hit these financial minimums, which would be you got to get to $500,000. Your readers probably look at that and say, "We can go way better than that." Anything above that is above the median in my data. You want to shoot for $1 million, $5, million and $10 million. I work with a family that has $100 million. Quite frankly, they're no happier than my families at work that has $1 million. If you want to shoot for $100 million, that's fine.
Here's a soft data point I'll give you. Happy retirees take more vacations than unhappy retirees. I don't think it's the financial aspect of it. Instead, they value experiences even more than the unhappy group and they're willing to spend more money to do so. Another financial one, happy retirees I see in the data showed this clear that they don't have a mortgage on their primary home. It doesn't mean they don't have rental homes that might have debt on it. That doesn't mean they don't have apartment complexes that might have debt on it. Their primary home, the place where they live is paid off. I talk about that in the book. Graphically, it's an interesting chart. It shows as years to pay off mortgage comes down, happiness levels go up.
It's light at the end of the tunnel because then you get to a point where if you're starting to put these pieces together, this may resonate with your real estate oriented readers. The number of different income sources is tremendously important. We've talked about in the book that this plateaus at a certain level. There's a higher propensity to fall on that happy group or the happy camp when you increase the number of different income sources. This makes sense too and I graph this out in the book, but if you think about it, the average happy retiree has called it three and a half different income sources. The unhappy group has called it two.
If you think about this, would you rather get one $10,000 check a month in the mail or ten $1,000 checks in the mail? If you think about this for me, you’d think, “It would be nice to get that one check every month. Logistically be easier.” In the real world, you’d rather have ten streams of income than one big river of income adding up to the same place. If one of them gets cut off or goes dry, you've got plenty of back-ups. Happy retirees figured that out. Either they figured it out or it's an inherent trait in the happy group. Multiple streams of income are important. In America, there are a lot of things and ways we get income. We've got Social Security for me and my spouse. An older generation, you might have veterans' benefits. My client base, about a third of them, still has pensions. Your reader group probably has 0% that will have a pension. Do you have a pension in your group? I doubt it. Have you ever worked? Does Get WealthFit have a pension program? Have you ever worked for a company with a pension?
Dustin
No.
Wes
Your readers probably are like, "I don't even know what that is." That's another income stream. The more of those we can put together. Maybe imagine you have a rental home. The majority of my client base that has an IRA or a brokerage account that we're investing for them. In income perspective, so generating cashflow from dividends and interest in distributions, they may also have five or ten or fifteen properties are paying them an additional monthly income as well. You look up and you're 55, your Social Security doesn't start until your early 60s but rental income, income from my portfolio that's paying me through dividends. I want to start adding as many of these as I possibly can. Another part of this and all these folks are trying to retire even earlier like 55, 51. There's the FIRE movement, the Financial Independence, Retire Early. These are folks that are 39 and they're ready to retire. You've got to have all these different income streams in place in order to have a fighting chance at making that happen.
Dustin
One of the things that jumped out to me in prepping for our time together was the line, “How to financially ruin your children in three easy steps.” I've got two young boys. I'm curious as to what exactly that little tidbit that I came across means? Can you give us the strategy as to potentially avoid it?
Wes
I read it at will, which is such an awful thing to do. Nobody wants to do a will. I have four little kids. I've got all boys. I've got eleven, nine, six and two. I'm trying my best to raise them without screwing them up completely. I'd say that there's a 50/50 shot, so maybe two will be totally screwed up and two will be good. I know exactly how to screw all of them up. That’s through not allocating money to them in a thoughtful way because I've seen it over and over again. I'm in the wealth management business. My families have anywhere from $1.5 million to let's call it $100 million, but let's call it $5 million and $10 million. I have seen this over and over and over again.
If families do not give their children an early purpose for money and if they don't teach them to gift charitably well, to begin with, that's a problem, number one. Number two, if they're allocated money too early, then that is the biggest killer of making you completely lazy and nonproductive in life. If you think about this a long time ago, the trust would say, "At eighteen, my grandchildren can start to get money." That makes some sense. They're going to college at that point. Maybe we can give some. What happens if your family has a several-million-dollar trust? Most trust payout 4% or 5%a year. If a family has left a seven-figure amount to a grandchild or even a child and they're able to take out 4% or 5% a year income. All of a sudden, they've got a base level of income enough to pretty much do whatever you want when you're young.
You're 22 or 21 and you've got $50,000 a year coming in, you're loaded. Think about college, I would earn $1,000 and that would last me a semester. You get $50,000 a year from your inheritance portfolio. You're probably going to be ruined for life because you don't have that same struggle that 99% of Americans have, which is, “I've got to be able to create my own path, my own income. Get my own place, get my own job, and struggle like all the rest of us.” If I'm not ever told or forced to do that, then I miss out on a huge part of normal economic life in America. I miss all the discipline that it takes to try to make it in the real world.
When I don't learn the key lesson, which is how unbelievably difficult it is to get to be financially independent or to make a dollar. It's hard to do that. I argue that it's getting even harder. It's getting a lot harder. If we're allocating money too early to our kids too soon, that's the easiest way to guarantee that they're going to be complete failures. What's the cutoff? For me, in the way I wrote up my things and my family if I untimely die, hopefully that doesn't happen. As long as you have been given no money by the age of 30, you've learned enough to understand how hard it is to make money in America. After that, it's okay to have your adult children start to get money. Before that, you got to get to at least 30 before you give any real money, anything of any significance whatsoever to your adult kids.
Dustin
That's important that they go out and get that discipline and earn that buck thinking over my past years in that. That's incredibly wise. I hadn't thought about ruining that process. It's sacred as you talk about.
Wes
I've seen it over and over again. If I get money at eighteen and you're 60 now, you still have the mental money mindset of somebody who's 22. You never develop that muscle. It's something I see successful because I work with successful families. They've got a minimum of $1 million or $2 million minimum. They all are thinking, "What am I going to do with this over time?" It's easy to pay for things for your kids in a significant way, even in their twenties. You’ve got to wait until you're 30 or 35 for your kids to get anything significant. Otherwise, you're doing them a disservice.
Dustin
You're the host of Money Matters. You've said you've been on the radio for many years. You've got one of the longest running personal finance shows or investment shows. What has surprised you in doing the show over that many years?
Wes
I turn it into a podcast once I'm done, but I'm still surprised that people still call in every time we say, "Give us a call here in the studio." Maybe it's because we're lucky to be on a station down in Atlanta on one of the oldest stations in America was founded in 1925. It's been around. People are listening on a Sunday morning. I'm always surprised that people over the air call in with their money problems and investment questions. I hope that never changes. Over time, it allows me to understand what people are scared about or most nervous about because the calls ended up having a theme.
Over the last few months, we've gotten a lot of calls about this. That is an interesting thing that's happening in the consumer marketplace place. What's happening? I can tell you the last many months, it's been an influx of calls and questions about lump sum pension rollovers, which sounds pretty wonky. A lump sum pension rollover is typically the result of a corporate downsizing. As strong as our economy has been, there are a ton of companies who are still getting rid of people. We heard General Motors make an announcement about this; 10,000-plus people being laid off from General Motors. It's happening in pockets of 500 or 1,000 in all sorts of companies. That's an interesting way to keep a pulse on what's happening in the corporate economy as well.
Dustin
What's your guilty pleasure spend? When life is cranking and you want to treat yourself, what do you spend on?
Wes
A guilty pleasure spend is my house stuff. It sounds boring. I've spent a ton of money staying in a location that is the center of everything. I'm always a big believer in A locations. I would call that a guilty pleasure.
Dustin
What is the most worthwhile investment you've ever made?
Wes
My best investment ever was leaving Corporate America and going independent.
Dustin
What's that investment you don't want to talk about?
Wes
I did a commercial for the Zune MP3 player. Zune went out of business a year and a half later.
Dustin
Wes, I appreciate you spending time with us on this episode and giving us your wisdom especially towards the end. It's always good to know that you're human and you have false starts as we all do in life. I appreciate you sharing. If folks want to learn more about the book and keep tabs with you, perhaps even tune into the show in Atlanta, how can they do that?
Wes
The podcast is Wes Moss Money Matters on the podcast app. My website where you can find that book and links to the book is WesMoss.com.
Dustin
Thanks, Wes. I truly appreciate you being on this episode.
Wes
It’s very much a pleasure. Thank you.

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Cutting your cable bill is an easy way to save tons of money. If you have home internet you already have access to on demand entertainment.

Cut the Cable (Bill) - 10 Alternatives to Cable Television

Lance Cothern

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Budgets for the Service Industry: How to Budget When You Work for Tips

Learn how to budget when you work for tips. How to take control of your finances in the service industry.

Budgets for the Service Industry: How to Budget When You Work for Tips

Jill Huettich

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Freeing Your 401(k)

Freeing Your 401(k)

How to Route Your Retirement Funds into Passive Investments

Andy Tanner

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The Hidden Power of Life Insurance

The Hidden Power of Life Insurance

How to Protect Your Ass(ets), Save Smarter, and Start Putting Your Money to Work

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