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The Money Outlaw Financial Philosophy

What is The Money Outlaw Philosophy?

In short, it is an alternative way to view personal finance, investing, employment, and life that is different than many other approaches. It involves looking at all these things very differently, but in a way that, if followed, will create an amazing quality of life for you.

Why Write Another Financial Blog?

The Internet is full of personal finance, investing, entrepreneurship, lifestyle blogs, and podcasts, so you may ask if the world needs another one? I will argue yes, because I have never found anything like what I will be covering in one place. Believe me; I have looked.

I have seen bits and pieces of things I discuss all over, but I have never found a single site that brings all the bits and pieces and expansive ideas into one coherent system, lifestyle, and comprehensive philosophy.

I am going to write the blog and create the content I wish I could have found 20 years ago when I started all of this. I spent a considerable amount of time building an amazing life and slowly digging information out of whatever crevice and place I could find it. I slowly assembled piece by piece the philosophy and ideas I will share here.

While I articulate this as one philosophy and strategy, it is made up of many elements. I understand that you may not be ready to implement what I discuss all at once. You may never be. That is perfectly OK, I have assembled and personally live it as one, but you are free to pick and choose the ideas and concepts that make the most sense for you. You can stop with just one or go all in.

The bottom line is this is a personal and individual approach to business, life, freedom, and financial independence. However, you choose to tackle it; you will be happier for your efforts.

Let’s get started.

Money Outlaw Core Concepts

The core lifestyle/philosophy is built around three main concepts:

  • Entrepreneurship
  • Alternative Investments
  • Economic Systems


Having your own business is probably the single greatest thing a person can do to achieve financial independence, freedom, and happiness. I have been a full-time, self-employed freelance consultant, copywriter, web designer, professional speaker, investor, and entrepreneur for almost two decades. I will stay an entrepreneur until I choose to no longer work. From my perspective, working a 9-5 job that you find OK, or worse, dread going to each day is the stuff nightmares are made of.

A Living Nightmare

Have you ever woken up in the morning when your alarm went off and quickly calculated how many years you had left until you could quit because you hated your job so much? Have you ever dreaded working, seeing, or interacting with co-workers because they were truly horrible people? Have you ever had to hang out with those same employees at “official” company functions and pretend you liked them?

Have you ever stood before your boss and had to sell him/her on why you should get a promotion or raise? Have you ever tried to convince that same boss why they should invest in you and send you to some training or conference? Have you ever been fired or laid off with 5 minutes of notice, given no severance, and had your household income cut by 50 or 100% in an instant?

Before I started my own business, I experienced every one of these things at one time or another. This was my living nightmare that filled my waking hours. Some people go on living this way for decades. I have met some of these same people at various times in my life.

These are people that are almost dead inside with nothing left to give to anyone. To make matters worse, many of them have such crappy investment and savings choices that their “retirement” will be an extension of the same nightmare they have already lived, except with more poverty to add to the misery.

Vow today not to let this be your life and legacy.

Freedom for Life

As an entrepreneur, I work on projects that truly inspire and excite me. I get to create, build, and grow every single day. I don’t feel like I have “worked” a single day in almost two decades. I start and end work when I want and take vacations or time off when I want. I work with inspirational and talented people that I enjoy every day. I make the money I want and create an incredible work/life balance.

I am a passionate lifelong learner. When I want to boost my income, I learn a new skill. I attend seminars and conferences when I choose. I start activities that I find interesting whenever it strikes me. I have created new businesses and ended them when they bored me or became unprofitable.

If I found myself working with a client or contractor I found disagreeable, I fired them and never looked back. I can stay light on my feet and move as the market changes. I have multiple streams of income to make sure 100% or even 50% of my income will never disappear in a single blow.

When we have a beautiful summer day, I can simply take the day off or choose to work outside on a laptop. If I get bored working in my home office, I can move to another location or another country. I have complete freedom and you can as well. What I did isn’t magic, or a choice limited to a few lucky people. You simply need to decide you want it enough to overcome the fear of taking this step.

Flexible Approach

How you set up and operate your business can be infinite. You can choose the route of a freelancer, or you can choose to build a large company with employees that you one day sell for a massive profit. You can also strike a balance and build small or even micro-businesses that you later decide just to end and start something new or sell-off. You can set up businesses that are location independent where you can travel the world and run from anywhere. You can work in one industry or many.

My own personal choice was to start working as a freelancer and over time start side-hustles or micro-businesses that complimented my interests or existing freelance activities. Over the years I have tried a lot of different things. Some of them worked out and some didn’t. I became bored with some and stopped doing them, but I used my freelance business as the engine that funded and gave me the flexibility and freedom to try new things. In the blog you will see that I focus mostly on freelancing as that is where my own interest and experience is at and the one I think most fits in with the Money Outlaw vision.

My Story

Some of you right now are totally jazzed and ready to start a business today. Some of you are reading with abject terror and thinking you could never do this. Some of you may be thinking you could never leave your “secure” job and steady paycheck. I was in the latter category when I started. I was just fired from the last traditional job I would ever hold.

I had a young son and another new baby on the way with a mortgage to pay and very little savings. My corporate ladder-climbing ambitions of previous years didn’t work out. I tried finding a new job, but nothing worked out. I had to do something, so I decided to start a business. This is NOT the optimal way to begin a business.

I grudgingly worked day after day, kicking and screaming into entrepreneurship. I didn’t even have business cards when I started. If someone had called me up and offered me a job in that first year, I would have dropped what I was doing and joined them in a heartbeat.

I remember the exact day when this changed. I had been in business for about three years. Each year had been progressively better than the previous year. A friend thought she would do me a favor and introduced me to a large Fortune 500 company that needed a senior marketing vice president overseeing a divisional level digital marketing program.

The company sent me the job description. It was written for me. Everything on the job description was a perfect fit for me. It was a 6-figure compensation package. It started with five weeks of paid vacation. There was even a plausible path to the C-suite if I performed well. The job was mine for the asking…

I turned it down.

I had zero regrets with my decision. I have never looked back. I hit the delete key and went back to work on my current project in front of me and never gave it another thought. Being an entrepreneur for almost two decades has been one of the single best decisions I have ever made.

Alternative Investments

Most people have no idea what alternative investments are because Wall Street firms spend an extraordinary amount of marketing money to make sure you don’t. Compound that with the general population’s attitude on learning about investing and you have a recipe for mediocre investment returns for life. When they think of it at all, most people think of investing as a company-sponsored 401(k) plan with a bunch of mutual funds inside of it with fancy names like “Total Growth & Income Fund” and other lofty-sounding names.

These funds often come with a prospectus that boldly puts the One, Five, and Ten-Year investment returns showing impressive results at the top followed by pages of micro-printed disclosures that nobody ever reads. If you are lucky, your plan comes with a match that your HR director tells you is free money, which is good because you will need it to overcome all the disadvantages!

In smaller companies, these plans might be set up by somebody’s brother-in-law that became a financial planner last week! Their only expertise is having taken a 40-hour class in a hotel ballroom and passing with at least a 70% on a state-sponsored exam! This is the person that could be responsible for your financial future during your retirement years! A plan and advisor like I am describing are far more common than you could possibly imagine. Yes, I have had “access” to a plan like this in my early life and have the financial scars to prove it.

Financial Services Industry has Dirty Laundry

Most people have no idea which investments they should choose, so they hire a financial planner who they believe has their best interest at heart. They put money away each paycheck, rarely open or understand their statements, and meet with their planner once per year who assures them, they are on the road to a comfortable retirement somewhere warm.

Boxer, the hard-working horse in George Orwell’s Animal Farm, thought the same thing until the day of his retirement when he received a one-way trip to the glue factory!

Sadly, many of these fancy-sounding funds perform poorly and are loaded with tons of fees. They have horrible returns that are doctored up by fancy marketing that makes your average con man look like an amateur. The worse thing is some of these funds are managed by self-centered, incompetentgrifters, managers that can be beaten by a monkey throwing darts at a stock chart! The only person that is headed for a comfortable retirement in this scenario is the mutual fund managers and your broker for selling you this garbage!

Investors that can outperform the market in the long term, such as Warren Buffet, are beyond rare. I think of them as once-in-a-lifetime geniuses. In my opinion, the vast majority of fund managers don’t fall into this category. Some might be able to beat the market for a short period of time, but most will eventually lose their footing and either match the market or more likely, under perform it over time. Between their high fees combined with the long-term poor performance you end up losing.

Does this mean you should swear off all Wall Street investments? Not necessarily, I invest in them and they can be a part of a well-diversified investment strategy. I decided that the use of low-cost index funds, ETFs (Electronically Traded Funds), and carefully selected individual stocks was my best strategy. In another article, I will explain why. However, notice the keyword I just said, these are part of your portfolio. So, what makes up the other part?

The Hidden Investment Market

Wall Street and all the products they sell are a small microcosm of an infinite world of investment possibilities. The investments I am talking about can have great returns and easily dwarf the stock market’s returns in any given year. These investments can be tax-advantaged by using self-directed retirement plans where you can easily make double-digit returns and never pay taxes on it! It is 100% legal and done every day by smart investors.

I call this the hidden or alternative investment market because these are investments you will need to find and put together. They are not going to be mentioned by your financial planner or offered by your company’s 401(k) plan. You will need to find and, in some cases, create them. It is investing for the active, motivated, and knowledgeable investor.

I am talking about real estate, private lending, limited partnerships, notes, private equity, cryptocurrencies, alternative energy, and startups. These are NOT investments that you log into your brokerage account, click a button, and buy 100 shares. My focus has been on real estate based investments which include rental properties, flips, private lending, lease/options, and other related vehicles. This will be my primary focus on the blog, but understand there is an even wider world of alternative investments.

You will need to study, actively find, evaluate, assemble, and manage these investments. They can be risky if you don’t know what you are doing, but so can giving all your money to a financial planner and letting them put all your money in actively managed mutual funds with enormous fees for 30 years.

Risk is based on your perception. I don’t consider these investments risky because I take the time to learn how they work and never risk more than I can afford to lose and still recover. I also employ strategies to maximize my upside potential and minimize my downside risk. This is much easier to do with alternative investments. You have considerably less control over stock market investments. In the stock market, your choices are to sell or pray the investments bounce back. In alternative investments you have numerous options, often limited only by your imagination, to find, manage, and profit from.

Your financial planner will tell you they are some of the riskiest investments on earth and warn you in the strongest possible language to stay away from them. They will tell you to put your money in a nice, safe, actively managed, diversified mutual fund that the colorful marketing brochures say will go up year after year (or not). Your financial planner is right; these investments carry sky-high risk. Risk to his retirement when you figure out you can do better elsewhere!

Your Money – Your Responsibility

The bottom line is nobody, and I mean nobody cares as much about your money and financial independence as you do. If you are a parent, would you ever give your child to a total stranger to raise for 40 years and hope they are there to help you in your retirement years? As absurd as this example is, that is the financial equivalent of what people do every day when they hand all their money to a financial planner and Wall Street.

YOU need to take responsibility for your money and your investments. Study and learn about investing, find profitable investments, actively manage them, and use those investment earnings to create the life you want. I am sorry to say, but you can’t outsource this job and hope things will work out. It won’t. Be a Money Outlaw Investor that actively finds profitable investments, manages your portfolio, and enjoys the rewards for doing so.

Economic Systems

Think of this final cornerstone not as the study of the single social science of economics but rather of anything that impacts the economic world in which we live and how that intersects with your financial life. Those things could be laws, regulations, taxes, government policy, or economic forces such as inflation or interest rates. I classify this entire area of study under the term economic systems because each element has a broad impact on the economic environment that we must live and function in.

For example, new tax law will impact your businesses and investments. As a real estate investor I have to deal with many laws from the local to the federal level. As a citizen I am affected by inflation and interest rates like everyone else. However, there are strategies that you can set up that blunt or remove some of these obstacles from your path. If you know how to use them you will benefit from them. This is especially true in the area of tax, but also other areas as well.

The world we live in is a rules-based world made up of systems, processes, and people. These elements come together to create governments, laws, and economies. Those governments don’t often have your best interest at heart when they form the laws, regulations, or taxes that are part of modern economic life. Too many times their actions are driven by lobbyists, political pandering to key voting constituencies, or getting re-elected. Your general financial welfare doesn’t usually rate very high on their list no matter what they say to the contrary.

Sometimes the laws and policies created have devastating and unintended consequences that can hurt you in ways you could never have dreamed of before it happens to you. Here are just a few examples of what I am referring to…

Taxes – The Great Game

The U.S. tax code has a mind-boggling number of pages. Buried within this blizzard of paperwork is a complex set of rules, but not just one set of rules, but several. Those that understand how to navigate those rules can arrange their life, business, and investments in a way that they pay considerably less taxes than someone that doesn’t plan as well.

For example, if you own a business and have it appropriately organized, you have many ways to write off expenses and control how and when you are paid income. Using these rules can dramatically lower the taxes you pay compared to another business owner or to someone who works as an employee and only earns W2 income, which is the most expensive income on earth!

If you invest in real estate, you get many other tax incentives that other people don’t get, but still, get to enjoy the income from these investments. You can also buy and sell properties in creative ways where you minimize or defer, sometimes forever, the taxes you pay.

If you set up the right investment accounts and learn ways to manipulate those accounts, you can minimize or eliminate taxes on your investments. For example, do a real estate flip inside of a self-directed Roth IRA, make $25K, and never pay a dime in taxes on that gain.

I am not a CPA, and I don’t give tax advice, but I am a student of systems and rules and figuring out how to move in and around them to benefit myself financially. I study the tax code, think creatively, and work with professionals to minimize taxes every conceivable way possible, and I do it legally. It is possible, but you must decide you will invest the time and energy to learn how.

Inflation – It That Devours Wealth

Everyone has heard of and experienced inflation, but few people understand it. In fact, as I write this, we are experiencing some of the highest inflation numbers we have had in 41 years! It is now an everyday occurrence in every developed nation on earth, but it wasn’t always so. When governments discovered they could print their own money in whatever quantities they wanted and force their citizens to use it, the genie was out of the bottle. Inflation became a plague on humanity, and today people don’t even seem to question it any longer.

People simply accept that prices will go up on everything they buy year after year. The Federal Reserve Bank just announced that they believe 2% is an “acceptable” inflation rate. It’s only 2%, how bad could that be? A 2% rate will eventually double prices on just about everything you buy. That is horrible news if your savings are in bonds paying .05% or bank CDs paying .02%, and you need to live off the income those investments generate. You are getting poorer every single day.

I once met an investor that described having cash or bank deposits like CDs as being equivalent to having an ice cube sitting on a sidewalk in the middle of summer. It just melts away and becomes less valuable every single day.

I recently read an article by another financial blogger that was discussing the 4% rule. If you don’t know what this is, it is the withdrawal rate that financial planners agree you can draw from your savings each year safely and not run out of money during retirement before you die. This blogger said that now that interest rates on safe investments such as bonds and CDs are so low this rule should be adjusted to a .5% withdrawal rate each year…


For those of you reading this in 2023 and thinking I am off my rocker since interest rates are now above 5% and you can get CDs and interest on savings near this level, don’t think it will last. I don’t care what the Fed says. They need and want inflation. It is what causes the Federal government to borrow massive quantities of money and grow the national debt by trillions. They get to use cheaper dollars when inflation exists to pay back that money. The Fed doesn’t want to eliminate inflation, just reduce it. That means that eventually interest rates will drop again and interest earned on savings accounts, CDs, and bonds will drop into the toilet again. You can choose to not believe me, but I have seen this play before. You might do OK for a little while with high yield checking account, but eventually you will be wondering how the interest paid dropped back to less than 1% again.

With a 2% accepted inflation rate and taxes to boot. Talk about a recipe for poverty in old age.

When you understand how inflation works, you can start to create strategies to mitigate its horrible effects on your life. Do you want to know an investment that generally rises with inflation, is stable, in high demand, and has low risk? Real estate, specifically rental property. Housing is something needed by everyone. The real estate itself generally rises with inflation, and so do the rents you collect.

This is one example of how economics affects your quality of life and understanding it and working around it can make your financial life better. To do this, you need to be active and learn how this stuff works and create strategies to mitigate it.

The Matrix

In the fantastic 1999 science fiction movie (Outlaws love science fiction), The Matrix, we learned machines controlled the world, and people essentially lived like slaves in their own minds. Some of those people learned how to break out of this prison. Those that got out could travel freely in and out of the Matrix.

The heroes understood it was a rules-based world created on systems and processes and how to work in and around those systems to do what they wanted. That is the same philosophy I want you to adopt when thinking about this final cornerstone of what I call the Money Outlaw philosophy. Take the red pill and see how deep the rabbit hole goes…

The forces, systems, processes, and people that build our economic world can be outmaneuvered. You must always be asking how and why things are the way they are. You need to be continually thinking creatively on how you can maneuver around them. These rules are typically foolish and dumb or the result of outdated thinking and unintended consequences. You can either throw up your hands and live by them or find ways around them.  

An Alternative Way – Think Differently

You can see, what I call The Money Outlaw philosophy is simply a way of looking at the world we live in differently. It involves being more active in every area of your life. It requires asking questions, thinking creatively, finding new ways to think and maneuver. Life will happen if you do or don’t choose to live it actively. The rewards are better if you choose the active path.



You can get a job somewhere, make straight W2 income, elbow your way up the corporate ladder, probably not be happy, or build a business, and enjoy freedom while moving through life. I chose to be an entrepreneur, and that decision created the first corner of my foundation and philosophy on life.

Alternative Investments

You can choose to invest the same way a vast majority of society does, be ripped off by high fees, watch your nest egg vanish in a market crash, have your paltry gains eaten away by taxes and inflation, or you can choose a different path. The world of alternative investing became the second corner of my foundation and philosophy.

Economic Systems

You can accept the world, laws, taxes, and economic forces at work around and on you at face value, or you can choose to understand them and learn how they can work for instead of against you. Deciding I would learn how these forces worked and how I could work in and around them creatively and grow my wealth was the final piece of my foundation. My freedom trifecta.



Active Living is Key

If I have used the word “active” once, I have used it a hundred times. I don’t want you to breeze past this because it is a critical component of everything I do. Being active means taking decisive action. It means spending time thinking creatively. It involves a lot of studying, learning new skills, and lifelong learning.

What do I mean by that? It means that on a sunny Saturday in October, instead of being at the football game you might be in an investing seminar learning how to finance and flip properties. It might mean instead of finishing dinner and binging on Netflix every night that you read books on small business, investing, economics, or take an online class.

Your investing also looks very different. Instead of the “set it and forget it” of an actively managed mutual fund, you hunt down a dilapidated house in a rising neighborhood, negotiate a great price on it, actively rehab it, refinance it, and rent it out.

Instead of making 7% (if you are lucky) on a mutual fund that taxes, fees, and inflation will rip apart, you created an asset that throws off $400 each month, before you retire. It also markedly magnifies your net worth. Repeat that four times in a year, and you just created $1,600 a month of additional income that is nearly tax-free because of favorable tax laws. I am pretty sure Netflix can’t do that for you.

Some of you may be saying this sounds like a lot of work. You would be right. I never said this was easy. Anything worth doing takes work. If it were easy, everyone would do it, and it would cease to be noteworthy. I said it would be rewarding and allow you to create an extraordinary life, and it will. As Morpheus says to Neo, “remember, the only thing I am offering you is the truth, nothing more.”

Think Differently

As I said in various parts of the site, the Money Outlaw lifestyle is about thinking and living differently. That requires you have an open mind about what constitutes a career, sound investments, and how you interact with economic systems, the impact of taxes and laws on all of these things. Most people accept the mundane and traditional because they can’t think differently.

They assume that the traditional way must be the best way because everyone is doing it. Millions of dollars and legions of marketing and public relations professionals put out advertising, PR, content, entertainment, and other media to continually massage your mind into believing and thinking this way. You need to be able to step outside of that thinking and manipulation and realize there is a better way to live.

In the early days of the computer industry in the U.S., the dominant computer company in the world was IBM. They were called Big Blue, and nobody challenged them. They were the proverbial 800-pound gorilla in the room. They had a tagline that read: Think

Other players eventually entered the scene and began chipping away at Big Blue. One of those pioneers was none other than Steve Jobs, the founder of Apple. Apple is the first company in history to reach a trillion, with a “T” stock valuation. He came up with a new tagline for his company that most people have seen. It read: Think Differently


The information contained within this website is provided for informational and educational purposes only and is not intended to substitute for obtaining legal, accounting, tax, or financial advice from a professional tax planner or financial planner. Full disclosure

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