Mr. Hobo Millionaire Observations on Life and Money

AuthorMr. Hobo Millionaire

I blog about money, financial independence (FIRE), life, and entrepreneurship. I got rich slowly (over 20+ years) with a niche software business. I also failed at a number of other things (and mild success with a few others). I share what I did right along the way, and a lot of what I did wrong, with a goal to encourage you think differently about life and money.

GoFundMe Is Not A Financial Plan


A couple of weeks ago, I ran across a story of a semi-famous radio host who had passed away. I didn’t know him, and I had never heard of him, even though many seem to know him. I’m not going to mention his name, because I won’t be pointing out very kind observations about him and his life.

The reason he jumped out at me was because of how many people have talked about the impact he had on their lives. He evidently spoke a lot about small business and entrepreneurship.

What others said about him…

I highly respected [person], listened to him every morning when he was on [radio station]. I spoke to him both on the radio and in person more than once. 

[Person] taught me a ton! Will be greatly missed…

Your heart toward small business and entrepreneurs was incredible. Someone should start a [The Person] Foundation, whose sole purpose is to help, encourage, and support small business and entrepreneurs.

What does this have to do with GoFundMe and Financial Planning?

He apparently had no net worth and no life insurance in place.

Yes, you read that correctly.

You see, he was in his early 50’s, he had a wife, and he had 3 young children. No net worth. No life insurance. How do I know this? Because a close friend started a GoFundMe for him. It reads:

It comes with a heavy heart, that we announce the passing of our good friend [First Name, Nickname, Last Name]. [Nickname] loved his job as a radio talk show host, and he was a great husband and father.  This page is to raise funds for expenses and the needs of the family.  [Nickname] leaves behind his wife, [Wife’s Name], and his three children [Child 1], [Child 2], and [Child 3]. 

GoFundMe is not a financial plan.

This guy should not have been giving advice to anyone. He was an utter failure. He was NOT a great husband and father (good maybe… but not great). He was living a lie of success over the radio about being a successful entrepreneur. Successful entrepreneurs don’t need a GoFundMe to take care of the family after dying. And even an unsuccessful entrepreneur could have a cheap life insurance plan in place to take care of his family. Instead, his family now apparently has no savings and is dependent on GoFundMe in the short term just to get by. Understand, this guy was famous enough that his GoFundMe has raised over $130,000 in just a week.

Term life insurance is not expensive.

A $500,000, 30 year, term life insurance policy, might cost ~$25/30 per month for a healthy 30 year old. I had a $2,000,000 term life insurance policy for many years while I was building my net worth. It was only ~$150/month.

Bloggers who say you shouldn’t waste money on term life insurance are foolish.

I won’t name names, but there are a number of financial bloggers who reason term life insurance is a waste of money… that the likelihood of dying is too minimal to waste the money. This is utter foolishness. Super wreckless. Dumb. Am I making myself clear?

Term life insurance is a super cheap for the peace of mind you get in return. $30/month over 10 to 20 years while you are saving to become financially independent is not going to slow down your savings rate that much. $30/month, over 20 years, compounded at 7% totals $15,000. You’re trading the “wasting” of $15,000 for $500,000 of financial peace for your family. It’s nothing.

I would recommend getting enough life insurance to cover your eventual FI number.

The idea being your wife/family could live forever off your “FI” life insurance amount “forever” with a ~4% withdrawal rate. And once you reach FI, you could remove this term life insurance completely, or reduce it to simply cover funeral expenses.

Why am I being so hard on [Person]?

I’m speaking strongly about this situation, because I too lived wrecklessly for a number of years. I was divorced in my early 30’s and had a 9 year old son. I was early on in my entrepreneurial struggles. I had a good 10 year window from roughly age 30-40 where I didn’t have any life insurance, and had I died, my son would have been in really bad shape. Really bad. I used to get on plane flights and think… if this thing wrecks, I’m leaving my son in such a terrible situation.

PLEASE get a term life insurance policy for your family. Please. I don’t sell life insurance. I don’t have anyone in my family who does. I don’t have any friends in the business. I’m not trying to convince you of it so I can make money from it somehow.

Note: I am recommending TERM life insurance, NOT whole life insurance. I am 99.9% against whole life. I am leaving a .1% option for some rare case where it might make sense in the future.

Don’t be this guy. Don’t be me (in this way) in my 30’s. You owe it to your loved ones to consider what things might look like financially if you weren’t here. It’s selfish and wreckless to do otherwise.

Death never comes at the right time, despite what mortals believe. Death always comes like a thief.

Christopher Pike

Be financially prepared… just in case the thief shows up unexpectedly.

Mr. Hobo Millionaire


My Dumbest Financial Mistake Ever


I’ve made a number of dumb, bad, financial decisions over my 50+ years of life. But the single, dumbest, financial mistake EVER… was buying a set of encyclopedias. I know what you’re thinking. Oh, that’s not that bad. At least encyclopedias are educational and you can get a lot of use of them! Yes. Yes, but…

But… Except…

Except for the fact that I was in my early 20’s, newly married, we had NO other furniture except for a bed, and the rest of the apartment was 100% empty. Why did I buy them? Because it came with a “free” TV, and I didn’t have one. And I bought these from a door-to-door salesman at an apartment complex. I spent around $1000-$1500 for them.

How bad can it be?

$1000-$1500 is a lot of money all by itself. To make matters worse, had I invested that money in the S&P 500, and re-invested the dividends every year, that $1000-$1500 alone would have grown too… wait for it… $20,000-$30,000 today.

So in the end, as of today, I spent $20,000-$30,000 on a set of encyclopedias… and a TV.

A man must be big enough to admit his mistakes, smart enough to profit from them, and strong enough to correct them.

John C. Maxwell

Financial mistakes are dumb now. Compounding makes them worse.

Mr. Hobo Millionaire

Minimize the financial mistakes you make over your lifetime. Don’t beat yourself up, but understand, financial mistakes compound. The money you lose from a bad financial decision is gone forever, and so is the compounding of that money. You must limit these bad decisions.

One other tip

One other tip that will save you way more than it hurts you is don’t answer the door if you’re not expecting someone, and don’t pick up the phone if you don’t recognize who’s calling you. This one decision will save you more than any “missed” opportunities. Sometimes what you don’t know can’t hurt you.

What about you?

What was one of the dumbest financial decisions you ever made? I’ll be outlining my full list in a future post.


Entrepreneurial Success Doesn’t Look Like An NFL Sack Celebration


Mark Gastineu was a great NFL defensive end for the New York Jets. Some time in the 80’s, he started the NFL craze of over celebrating a tackle. In some ways it’s kind of entertaining, but ultimately I believe it sets a bad example (more on that in a moment). At this point in time (20 years into the 2000’s), it’s gotten out of hand in the NFL. We now see players over celebrating a tackle even when their team is losing! I also understand that the Madden football video games had a big affect on current players, too. They grew up watching the video game characters over celebrate, and now they are modeling that behavior.

What’s wrong with over celebrating?

I believe it sets a bad example, because it models incorrect behavior in terms of competition, struggling, and perseverance. Long term success takes years, not one day or one moment. Yes, professional football players have put years into being where they are, but on that day, the “success” goal is to win a football game, and to win multiple games over a season, and win in the playoffs, and eventually win a championship. The goal is not to make one good play.

Over celebrating is a distraction. Plus, most of the time, you’re doing it because you’re looking for a pat-on-the-back or praise from others. As an entrepreneur, you need to be able to push on without praise. If you believe every day is going to be jumping up-and-down with joy, you have a big shock coming. Most successful entrepreneurs plug away for years, working many long days, many alone, in solitude. Sure, you should celebrate small wins internally, but never lose focus of the end goal.

Facebook and Instagram posts are not real life (not IRL).

Many people think entrepreneurship is what the celebrities post. No, that’s advertising. They’re trying to sell you on how they live, so you buy what they sell, so you can feel like you’re as successful as they are. Don’t buy what they’re selling. And unless you’re a celebrity already, that kind of advertising won’t work for you. Any entrepreneur working towards a goal doesn’t have time to post silly stuff on Facebook or Instagram on a daily basis.

Ever see people post stuff like this?

Started a diet today — Ate a salad!

Ran 1 mile today! Marathon here I come!

Started writing my book! Chapter 1 done!

And then they never post anything about it ever again. You know why? Because they quit.

Coffee is for closers only.

Blake (Alec Baldwin in Glengarry Glen Ross)

Over the years, if social media would have existed, and I was being honest, I would have posted stuff like this:

I worked 16 hours today to fix an issue with my software. I got nowhere. Off to bed and to try again tomorrow.

Invested 20K to get a chance to work with a bigger company. They said no.

It’s 3am and my customer just texted me. I’ve got to get up and work on a problem.

I’m rewriting our software from scratch starting today. I’ll finish in 2-3 years after 16 hour days. Shipped! Oh now I have 5 more years of bug fixes and iterations, working 16 hours a day.

My son just asked me why I work so hard with so little to show for it.

I’m working two full-time jobs for a chance to chase my dreams. I’ve been doing this for 3 years. 

My investor just pulled the plug on my company after only 3 months. I worked 3 years to create this product. And it’s over. I have to go ask for my old job back.

There is no such thing as an overnight success.

Entrepreneurial success is bunch of big struggles and private, hidden little wins. I cry when I listen to other entrepreneur stories about the long years, days, and hours put into creating a product… and they’re finally having some success. I know how hard it is. I’ve lived it. Multiple times. I have no idea what I would have done had I not eventually started having some success. I’m pretty sure I would have kept plugging away since that’s what I had to do for 20+ years anyway, but you never know. It’s SO hard. I can promise you I was never running around with my arms up high celebrating saying “look at me”! Most people, except my family, have no idea what I went through to get to where I am today. Friends and acquaintances had no idea how hard it was then or how good things are now. That’s why I blog anonymously. I don’t want personal attention, but I do hope you get something from this blog. I hope you know you’re not alone in your entrepreneurial journey. I’m rooting for you, even if it’s in private.

Now go do the work…

Successful people do what unsuccessful people are not willing to do. Don’t wish it were easier; wish you were better.

Jim Rohn

Now go do the work…

Mr. Hobo Millionaire


Don’t Set Your Goals Too High


The secret of getting ahead is getting started. The secret of getting started is breaking your complex overwhelming tasks into small manageable tasks, and starting on the first one.

Mark Twain

Don’t set your goals too high.

Mr. Hobo Millionaire


What Do You Mean Don’t Set Goals Too High?

I am all for setting big goals, but goals should not be impossible. Furthermore, you can be a big success with small goals. Let me give you some examples…

You don’t have to have the success of Warren Buffett (Berkshire Hathaway) to be considered a success in investing. 

You don’t have to have the success of Bill Gates (Microsoft) to be considered a successful software entrepreneur.

You don’t have the success of Mark Zuckerberg (Facebook) to be considered successful as an app maker.

You don’t have to own as much land as Ted Turner (he also created CNN/TNT/TBS) to be considered a success in real estate.

You don’t have to sell as many books or have as many podcast downloads as Tim Ferris to be considered successful in media.

Do I Need To Go On?

If you only acquired $1,000,000, or $2,000,000 or $5,000,000 saving and investing over your life time, are you a failure because it’s not billions?

If you only created a software company or app maker that earned you $200,000/year for  25 years, are you a failure?

If you only bought and paid for 3 rental houses in your lifetime, and used the rental income for your early retirement, are you a failure?

It doesn’t take selling millions of books or having millions of podcast downloads to have some success with writing, blogging, and podcasting. If you only make $50,000 a year writing, blogging, and podcasting, are you a failure?

No. Of course not. But many people set goals that are way too big and end up quitting from disappointment when things aren’t moving quickly. Some set so high a goal they don’t even get started. They quit. They don’t even try. If I can’t be [insert name of famous person], I don’t want to even try.

Many Extremely Successful People Were Lucky

I’m not taking anything away from Mr. Buffett, Mr. Gates, Mr. Zuckerberg, or Mr. Ferris. They are all individuals who have worked very hard. Very hard. And you know I admire hard work. If they had 1/100th of their success, they would still be crazy successful. But the fact most are billionaires (except Ferris), there’s a lot of luck involved in their stories.

The world talks and prints so much about billionaires these days, though, it starts to feel normal. There’s nothing normal about a billion dollars.

And because it gets talked about so much, it may make you feel like you need to create a “billion dollar idea” or you’re not successful. You do not need billion dollar idea. And please understand I’m not knocking those billionaires. I promise. I’m a fan of entrepreneurship, free markets, and capitalism. I’m simply trying to stress to you not to compare your goals and aspirations to what they have accomplished — it’s not normal accomplishments, and some, if not a lot, of luck was involved.

Have You Heard About The Concept Of “1000 True Fans”?

Kevin Kelley created and documented this concept of 1000 true fans. He could have rephrased it as “Don’t Set Your Fan Goals Too High”. You could earn an income of $100,000/year if you could find 1000 people willing to spend just $100/year with you (or $8.33/month). Not too bad is it? Kevin’s “1000 true fans” concept is much more than that, and I encourage you to read the link to his original post (he’s also written a book about it).

Some of you are familiar with my own personal story. I created a successful, niche software company. Not a company you’ve ever heard of though. And I only had about 1000 companies or so as customers that did, on average, about $1000/year with me. Saving and investing that money allowed it to grow into millions. Am I a failure because I’m an unknown, small time, multi-millionaire? Of course not. And neither are you if you only create a $50,000/year income doing work you enjoy.

Set Realistic Goals

One of the most important factors of success is getting started. No one has ever been successful who hasn’t started. Don’t set unrealistic goals and then get overwhelmed with getting started and getting nothing done. Figure out your “minimum viable audience”.  The minimum number of people you need to engage/sell to that, if they supported you financially, you could be happy with earning that kind of living. Seth Godin had an interesting blog post about this topic. I also highly recommend his book “This Is Marketing“.

The topics “1000 true fans” and “minimum viable audience” weren’t being talked about when I started my journey in the software business in 2000. Actually, I re-started my software journey in 2000. My initial foray into software was 1993-1995, but that’s a failure story for another time. Study up on these topics, make a realistic goal, and get started!


Just “Showing Up” Allows You To Beat Most People


Let me say from the beginning, before the PC police show up, by “beat most people”, I’m not wishing any ill-will towards others. But if you don’t think life is a competition… you’re losing.

Life Is Hard

Life is very hard, unless you figure out a way early on to be very strategic with your goals. You won’t be able to map out a perfect strategy in your 20’s… or really at any age “perfect” is probably not attainable, but you should try. Don’t wander through life waiting for things to happen to you; work towards making them happen for you.

I wish everyone could be successful in some way. Most are not willing to put in the work necessary to be successful, though. And if your definition of success is a 9-5 job until you’re 70, 5-10 years of retirement, and then you die… then I wish you well. I’m not here to change your definition of success.

My personal story of success took a long time. I’m not the smartest guy, and I made a lot of dumb decisions along the way, and I had a lot of failures. The one thing I did right was every day, no matter what, I did something that improved my life just a tiny bit. As an entrepreneur, you never run out of things that need to be worked on. So, every day, I made progress on something, consistently, for years. And I don’t mean 1 or 5 or 10 years — I mean 20-25 years. And all that consistency finally paid off.

Do You Want More?

If you want more (and by more, I mean freedom to choose what you do with your time — NOT necessarily money), you better be willing to hustle and “show up”, consistently.

Passion is overrated. Consistency is underrated.

Passion is overrated. Consistency is underrated. Everyone talks about “find your passion”. Don’t take a job unless you have “passion”. Finding work you’re passionate about is great if you can find it — and it’s worth trying to find… but working passionately is more important.

Working Passionately is More Important

Working passionately, and doing it consistently is more important. Let me give you an example. Would you agree that everyone from doctors to nurses to trash collectors don’t always feel like doing their job? Would you want your doctor to stop mid-way through an operation and say “I don’t feel like finishing this right now”? If you need assistance at the hospital and call on a nurse, you wouldn’t want her to say “I don’t feel like helping you right now”. Everyone has bad days and negative feelings, but you must push through and be professional. If you’re waiting on an emergency transplant, and your doctor has an argument at home with their spouse, you wouldn’t want him to cancel your emergency surgery just because he’s having a bad day, right?

Are You Better Than A Squirrel?

If you’ve ever observed squirrels for very long, you’ll notice one thing for sure. They work on a daily basis to improve their lives by planting nuts for the winter. My wife and I have even fed squirrels peanuts. If you give them 10, they’ll eat 2-3 and plant/bury the rest. Oh… and they’ll usually plant/bury first — then eat. And they do this no matter what else is going on — every day. They “show up” every day to try and improve their future.

Feelings are Real, But They Should Not Always Control The End Result

I’ve known some psychologists that have given some really bad life advice to their patients. They tell people it’s OK to have feelings (and it is), but they do not explain that you need to carry on about your business no matter what your feelings are (at least most of the time). We live in a world where everyone wants to acknowledge their feelings and let it rule over how they react to everyone else. No one cares about your feelings (except maybe your parents and hopefully your spouse). If you work in customer service, it doesn’t matter what else is going on in your life — you need to be professional and be kind to the customer you’re serving.

“Showing Up”

You won’t always feel like “showing up”. But if you want to be desired and respected professionally, you must show up. You must honor your word. If you commit — do it. No one is perfect, and there are times you just can’t do what you said you would, but those times should be rare. And because “showing up” consistently is so rare, you will shine and be valued by others.

Don’t follow your passion, but always bring it with you.

Mike Rowe

Showing up (consistently) is a plan for success.

Mr. Hobo Millionaire


The Road Grader


As a child growing up in the country, and I mean way in the country, I lived at the end of a mile long dirt road. “Randy Road” was the name of this dirt road. Being it was a dirt/gravel road, it required monthly (maybe even bi-weekly — I can’t remember it’s been so long ago) maintenance to keep it flat, smooth, and drive-able. The maintenance was performed by an older man driving a large road grader (slightly smaller than the one pictured). Without the maintenance, the road would develop deep holes and bumps due to rain.

As a small boy, as you can imagine, this road grader was larger-than-life. Enormous. It had to move kind of slow to do a good job flattening the road. With it’s rumbling and roaring engine and grading of the road, I could hear it coming when it got to within a quarter to half a mile away. I would sprint down our driveway to watch the big machine go by our house (actually it was a trailer/mobile home).

Seeing the big machine would have been special for this little boy in-and-of-itself, but you see, the old man driving and waving at me made it just a bit more special… he would throw bubble gum to me from the big rig! Super Bubble gum to be exact. I’m tearing up while writing this… just remembering the excitement I had of this childhood memory. This would be the highlight of my week. I have no idea of this mans name, and I’m sure by this time he has since passed away. I hope he knows how special he made my childhood (and many other kids). You see, he wasn’t just giving out gum, he was giving out love, joy, and happiness. I, of course, didn’t see it that way as a child, but I sure do as an adult.

My point of this story? Be the road grader to someone (especially a child).

It’s not how much we give but how much love we put into giving.

Mother Teresa

Be the road grader to someone.

Mr. Hobo Millionaire


A Very Basic Intro to Investing and the Stock Market


An investment in knowledge pays the best interest.

Benjamin Franklin

A knowledge of investment builds wealth.

Mr. Hobo Millionaire

First and foremost, I want you to remember this one thing from this article, even if you don’t remember anything else… YOU need to know and understand YOUR money and investments.

  • Never stop reading and studying about money and investing.
  • Do not depend on others to handle your money.
  • No one will put your interests first like you.

With that said, here’s a few basic terms and things to understand about investing and the stock market…

  • Stocks are share of ownership in a company.
  • Stocks go up and down in value.
  • You make money (build wealth) from stock ownership either by buying a stock at a lower price and selling it at a higher price or by earning a dividend from the ownership of the stock.
  • Some stocks have dividends, some do not.
  • Dividends are when a company, that you own at least one stock in, decides to share it’s quarterly profits with shareholders. If a company pays a $1 dividend for the quarter, this is $1 per share that you own. If you own 10 shares, and the dividend is $1, you made a $10 dividend. If the company paid the same dividend over 30 years, and they paid the $1 dividend every quarter, those same 10 shares that you bought at the beginning would pay you $40 in dividends per year, for 30 years. That’s $1200 for doing nothing other than holding a stock for 30 years.
  • Companies that pay dividends can stop paying dividends if they choose to. There are no guarantees that a company will always pay dividends, although most large companies do continue to do so. For example, Microsoft (MSFT), AT&T (T), and IBM (IBM) have paid quarterly dividends consistently for the last 10-15 years. I am not recommending these stocks to purchase specifically, simply giving an example using well-known companies.
  • Some companies also reduce dividends. Some increase dividends. Again, they can do so when they choose.
  • A risky way to try and build wealth is to buy and sell stocks in very short periods of time. This is what “day traders” do.
  • One conservative way to try and build wealth is to buy stocks over your lifetime (buy and hold stocks over 30-50 years) that pay dividends, and use those dividends to buy even more stock. This is called “dividend investing”.
  • A stocks dividend yield is the yearly dividend amount (all 4 quarters of dividends added together) divided by the stock price. A yearly $5 dividend on a $100 stock equals a 5% dividend yield. A yearly $3 dividend on a $100 stock equals a 3% dividend yield.
  • Imagine owning a wide range of dividend stocks, valued at $1,000,000. Let’s say they have an average dividend yield of 5%. Every year, you will make $50,000 in dividends for doing absolutely nothing. Now imagine having $5,000,000 in dividend stocks… and you earn $250,000 per year, doing nothing, with that same 5% dividend yield.
  • You can sell a stock at any time. If you sell at a higher price than your purchase price, you’ve made money on that stock. If you sell at a lower price that your purchase price, you’ve lost money on that stock.
  • If you sell a dividend stock, you will not continue to receive dividends. You do get to keep any dividends you’ve made prior to selling the stock though.
  • Mutual funds are a large group of stocks that you purchase by putting money into the mutual fund itself. It’s called a “mutual” fund because many people put there money in as a group and buy large amounts of stock together. You are not in control of the stocks purchased or sold in this mutual fund. You are are investing in the fund itself, not so much the stocks. If you have no idea what stocks to buy, it is considered a conservative approach to invest in mutual funds. That said, as I pointed out at the beginning, I don’t believe in buying/investing in anything you don’t understand, and I don’t believe throwing money into mutual funds is conservative if you don’t know what you’re buying. Not all mutual funds are the same.
  • An extremely conservative approach to investing in the stock market is buying into a fund that purchase shares in a stock market index. If you look at historical data, there have been ups and downs (serious ups and downs), but over the history of the stock market, it always ends up, not down. You may have to wait years for a full recovery though. The stock market is not a short term investment plan. For example, the most recent “crash” was in 2009. From 2007 to 2009, the stock market trended down (per Dow Jones Industrial Average), dropping from 14,000 to 6,600. That’s over a 50% loss in value. So if you owned this group of 30 stocks, and average value of each stock was $100, they were valued at $50. If you panicked and sold at the bottom, you lost half the value of your investment. Here’s the good news, though. Since that time, the DOW market has recovered and gone to about 26,000! If you held those stocks, they’ve recovered and now would be valued at almost $200. And better yet, if you bought MORE shares at the bottom of the market, your money has quadrupled. If you bought $10,000 of shares at the bottom, those same shares are worth about $40,000 now. Dow Jones is what’s considered a market indicator. Just because it goes up or down doesn’t mean your stocks go up or down (unless you own those specific 30 stocks). The bottom line is if you can buy and hold investments for a long period, you’ll more-than-likely come out ahead. You never lose investment money until you sell the investment (at a lower price).
  • Generally speaking, when a stock that you believe in goes down, you should buy even more shares. If it was worth buying at $25, isn’t it worth even more to buy at $15?
  • There are income tax considerations with making and losing money in the stock market, too. Don’t let this scare you. Just be aware. This blog is about building wealth, so we’re encouraging you to save, not withdraw/spend. If you take money out of retirement accounts before you are of retirement age, there are usually penalties. There are pre-tax ways to save and post-tax ways to save. There are IRAs, 401ks, and SEPs… for the most part if you invest and save in these accounts, you do not pay taxes on it until you pull the money out at retirement. You’ll want to get more financial advice from a CPA in terms of taxes and tax planning.
  • Bonus note: You used to get an actual piece of paper when you purchased shares of stock. It would have the company logo on it, your name, the value, and how many shares you owned. It used to be a cool gift to buy shares of stock in a company and gift them to a newborn. This is all handled electronically now.

There are many ways to make and lose money investing in stocks. With this post, I simply wanted to highlight some basics. I probably went a little more into it than I planned when I started. But I wanted to make sure I covered most of the basics. There are a number of financial blogs out there (just google “financial blogs”). Hopefully, this gives you a more basic understanding than you had when you started.

  • Keep reading and learning.
  • Don’t take any one persons advice on money.
  • Learn and make your OWN decisions.
  • And RUN from anyone who tells you they know everything about money — of they have a “for sure” investment deal.



Summer Camp 1984 Changed My Life

Believe in yourself! Have faith in your abilities! Without a humble but reasonable confidence in your own powers you cannot be successful or happy.

Norman Vincent Peale

Don’t let anyone determine who you are or what you do in life.

Mr. Hobo Millionaire

You know how some teens are great at sports (gifted naturally to be the quarterback, running back, linebackers), popular because of their good looks, or super smart? That was not me. I was only a slightly above-average teen. I say “slightly above average” only because I was I was a pretty good kid, respectful to others and my parents. I was also a member of a church-based boys group much like the Boy Scouts, and I achieved the highest possible rank/awards in that program (achievements were mostly related to camping and nature). That said, I was not super popular, not picked first for sports teams, not the teenager everyone thinks of first (or even second or third). I wasn’t necessarily odd or picked on… just kind of normal and unseen. That all changed for me the summer of 1984.

Every summer from the age of 13-17, I went to a one-week youth camp in July. Here teenagers from all over the state got together, camped out in dorms, played co-ed sports, and did church stuff (but this story isn’t about the church stuff). The group of teens that went there from my own tiny church was about 25 people. The total camp was about 750 teenagers. My “social ranking” within my own church was in the middle or just below, so at the youth camp, it would have been in the bottom 30% by default.

One odd thing at these camps (and really a good thing) was that you hardly ever got grouped or teamed with anyone from your church. The camp leaders randomly divided all the kids coming in into mixed groups of teams so you could compete in softball, volleyball, and the likes. When teams were formed at the beginning of the week, the counselors would always ask who wanted to play what position. Of course, the popular people would always play infield in softball, and the short-stop position was the most popular.  At the end of every week, there would be an All-Star game with the best/most popular person from each team participating (usually this was the short-stop or pitcher). The All-Stars would play a softball game against the camp counselors and leaders.

I wasn’t terrible at softball, but I wasn’t that good either, but a switch flipped in my brain that summer of 1984. When the counselor asked the teens in my group who wanted to play what position, I immediately (and confidently) spoke up to play short-stop. And somehow, magically, I played the position like I never could before. I made zero short-stop mistakes during the week (until the All-Star game). And yes… I made the All-Stars that week! I was the only person from my church to make the All-Stars. It was surreal. I had always wanted to be “that guy”, and I made it!

Look, I know teen events don’t make a lifetime, and I’m sure no one remembers me from that summer camp. I’ve never even spoken to those folks again. But that summer changed my life. I realized I could be anyone or anything — it was up to me. Even if I had to leave my normal world to move to a new world, I wasn’t ever going to let anyone who knew me or believed I was someone else to limit me. I was a different guy when I got back from that trip (even with my own church friends).  I moved away from home a year later to go to college in Texas. In Texas, no one knew me or my past, and I had a blank slate to be whoever I wanted to be. And I had the confidence to do it because of the Summer of ’84. 

What does this have to do with wealth? Simply to encourage you to pursue and do whatever it is that you want to pursue. Don’t let anyone or anything hold you back. I’m not saying don’t get advice or listen to someone else’s wisdom (like mine!), but don’t let someone else’s negative feelings or emotions prevent you from pursuing what you’re passionate about.

An old picture of the actual campgrounds

What about you? Any life-changing moments from your teen years? Please comment below.


Cars Are Money Pits and Kill Wealth Building


Money may not buy happiness, but I’d rather cry in a Jaguar than on a bus.

Françoise Sagan

You will really cry when you see how much money (wealth) you lost on cars over your lifetime.

Mr. Hobo Millionaire


Million Dollar Mistake?

Raise your hand if you’ve heard the following: “Cars depreciate 20% when you drive off the lot.”

I had heard that many times in my life, but it never really sunk in until later in life when I started analyzing common expenses and building wealth. My goal with this post is for that saying (and MUCH more) to sink in, regarding what buying cars (especially new cars) does to your wealth building.

A $30,000 car financed over 5 years is about $500 per month. Most people look at a $500 car payment these days as no big deal. If you’re saving at least 3 x’s that amount per month AND you’re going to keep the car for 10 years, MAYBE you can justify doing 5 years of payments on a 30k car. Maybe. I still don’t advise it, but at least you’re using the car a long time AND you’re saving $1500/month to build wealth. For the rest of you, if you do this your entire life, and have little-to-no wealth built in 30-40 years, you have basically driven multi-million dollars cars your whole life. I hope you really enjoyed them! Because if you had spent less and saved the difference, you would have added millions in wealth. Don’t believe me? Check out these numbers:

If you took your $500 payment and reduced it to $200 per month, and saved the difference ($300 per month) for 40 years, this is how much wealth you would accumulate:

  • 0% return: $144,000
  • 6% return: $557,143.08
  • 8% return: $932,603.47
  • 10% return: $1,593,333.20
  • 12% return: $2,761,529.11

Think of all the people you know that are in their 60’s or later that have driven many large new cars over their lifetime and are broke. Think of all the young people (late teens and 20’s) that drive 30k+ cars. How much are they losing? I used that picture of the 4×4 truck above, because I see so many 20-somethings driving these in the South. It’s nuts. For the record, when I need a new ride, I pay cash for a used, 3 year old, Ford F-150.

Most people simply do not consider how much they are spending on cars. I have a friend who hasn’t built any wealth, who recently bought a 75k sports car on payments. He’s probably 20 years from retirement. Let’s assume he was going to spend 25k either way to buy a new car… he still spent an extra 50k that will be 100% lost over time. Do you know how much money he REALLY lost because of how that 50k could have increased his wealth:

  • 0% return: $50,000
  • 6% return: $160,356.77
  • 8% return: $233,047.86
  • 10% return: $336,375.00
  • 12% return: $482,314.65

That’s how much that extra 50k in car cost him over the next 20 years.

When you waste money on cars, you are decreasing your wealth… your net worth. If you wanted to “blow money” on something nice, buy a house. Blow all your money on a house. At least it won’t go down 20% in value as soon as you buy it (under normal circumstances). In most cases it will go up in value over time. A car, except in extremely “struck by lightning” circumstances, never goes up in value.

You say, yeah, but I’ve got a to have a new car to be safe or to not worry about it breaking down. That doesn’t take a 30k car. For that matter, you can generally get a really great, safe, used car for 10k. Until you build a large amount of wealth, you should probably drive good, solid, 10k used cars.

Build wealth and you can buy whatever you want when you’re rich. Check out this used car bargain…

Used Lamborghini Gallardo - A Bargain at $100,000
Used Lamborghini Gallardo – A Bargain at $100,000 (They Are 500k+ Brand New)

You’re welcome to argue how much you should spend monthly on a car, but you can’t really argue the numbers are astounding for saving just $300 a month over 40 years.

Question Everything



Question those in authority.

Question your political beliefs.

Question your spiritual beliefs.

Question everything.

Believe only half of what you see and nothing that you hear.

Edgar Allan Poe

Believe none of what you hear, and only half of what you see.

Benjamin Franklin

Question everything.

Mr. Hobo Millionaire

You are taught as a child to listen to (and mind) your parents, teachers, and leaders. You’re taught never to question anything (except strangers — don’t talk to strangers).

The older you get, and for some it may take many, many years… but at some point you’ll realize that SOME of the things you have believed in your life are flat out WRONG. Personally speaking, I came to that conclusion with my spiritual beliefs, and I came to it with my political beliefs. I’m not going to share what those beliefs were or are now, because I’m not looking to influence your personal beliefs… other than to encourage you to question whatever they are.

If your political beliefs go one way, listen to people from the other side, or the other middle. You will hear many people with one political belief turn off listening to other political beliefs completely.

You can learn a lot by listening to your enemies.

Mr. Hobo Millionaire

Since I’ve changed my opinion of certain spiritual beliefs, I’ve asked old friends and acquaintances that I grew up with and/or knew in my teens/twenties “Have ANY of your beliefs changed, at all, in the last 10/20/30 years?” And there response is either “No, not at all.” Or “No, why?”

Are you kidding me?! You’re 40, 50, 60 years old, and your belief is EVERYTHING you learned or was taught over your life was 100% correct?

I once asked a 50-something year old minister if he really believed EVERYTHING he preached was 100% correct. His answer was yes. So I said, out of all the world religions, all the different denominations, believers and non-believers in whatever, YOU, you are the single person in the world that has figured out religion for the entire world for all eternity? He said yes. It takes a special kind of narcissist to believe that.

Some people question what they see on the news. Some question whether the Earth is laid out the way we’re taught it is. Some question whether we really landed on the moon. Some question if we’re really exploring Mars now. Some question why certain wars were started. Some question what the government tells us. Some people think Edward Snowden is a traitor, some do not. Is it crazy to question those things? No (ok, well maybe one or two of those things). Everything should be questioned.

What does this have to do with wealth? Well, a lot of people have beliefs about money that deserve questioning (ie. they might be wrong). Beliefs like…

Money is the root of evil.

Anyone with money is evil, and they either inherited it or stole it.

People with money are selfish.

Money is bad. I’d rather be poor.

Rich people are spoiled.

Life is against me. I’ll never be successful.

Rich people are lucky.

Any of those sound familiar? Of course. And if you’re someone who believes any of those lines, you will probably never attain any kind of wealth. That’s what this has to do with wealth. Those are limiting beliefs in my opinion — but please, question me, if you disagree.

You will never change your beliefs or learn anything new if you always turn off the other opinion. Read books. Read other peoples opinions. Open your mind. Open your heart. Never stop learning. Question everything!

What beliefs have you done a 180 on in your lifetime? Please comment below.



Mr. Hobo Millionaire Observations on Life and Money

Mr. Hobo Millionaire

I blog about money, financial independence (FIRE), life, and entrepreneurship. I got rich slowly (over 20+ years) with a niche software business. I also failed at a number of other things (and mild success with a few others). I share what I did right along the way, and a lot of what I did wrong, with a goal to encourage you think differently about life and money.


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