Your Money Story and Your Life

Suppose you were given $100,000 today. What would you do with it?

Pay off loans?
Invest it? If so, where?
Spend it? If so, on what?

Does $100,000 make a substantial difference in your life?
If so, why?

What about $10 million? What would you do with that much?

Pay off loans?
Invest it? If so, where?
Spend it? If so, on what?

What do you think about money?
Do you love it, or hate it?
Do you understand it?
Do you judge those who have it?

What does money mean to you?
What does money stand for?
What is your money story?

How important is net worth to you?
How important is cash flow?

What does your spending say about your relationship with money?
What does your investing say about your relationship with money?

These are questions I am taking more time to ponder at this time of year and this stage of my life.

For the first decade of my business life, I followed a process that led me to financial independence…at least, temporarily.

I took far too much risk and it was short-lived. I didn’t know how to value my time and therefore made investments without considering the impact on my life, schedule, and family.

Most of my initial investments were considered “passive income.” But the reality was that they weren’t passive at all. They required time to acquire and even more time to manage.

In 2008, the economic downturn exposed my investment philosophy, and I lost my economic independence.

The good news is I asked new questions, learned valuable lessons, and developed a new model and approach to a more sustainable path of economic independence.

For the better part of the last decade, I had enough recurring revenue to cover my expenses. But due to selling my company, combined with increasing my lifestyle, I found myself no longer economically independent.


Upon selling my business, I could have stayed in my same home and invested my funds in fixed-income instruments like bonds, treasuries, or annuities. These would have provided plenty of cash flow to cover my lifestyle. It would have been easy to create enough cash flow to cover my expenses, but only by playing small.

I don’t want to play small.
I wouldn’t feel fulfilled being retired.

I’ve already done many of the things people reserve for retirement. I’ve traveled extensively. I haven’t delayed doing the things I enjoy for someday. Since 2017, I’ve gone all in on my hobbies. Comedy. Coffee. Whiskey. Writing. Shooting my bow. Fly fishing. Projects improving my cabin.

How I am choosing to invest came from answering the following questions. These answers have informed and guided my actions.

What does money mean to me?
What does money stand for?
What is my money story?
How important is net worth?
How important is cash flow?
How important is Soul Purpose, happiness, expression, fulfillment, and joy?
What does my spending say about my relationship with money?
What does my investing say about my relationship with money?

The answers were clear, so I invested heavily in several projects very meaningful to me:

Rather than spending time raising funds and answering to investors, I chose to invest my capital in these projects. Instead of putting the money into a bank account, retirement plan, or something that I could cash out the next day, I chose to invest in myself. To make investments that take time to create cash flow and fully pay off.

Sure, some of these projects could have paid me up front, like a book. After having success with multiple books, I could have gone with a traditional publisher, and gotten an advance. But instead, I went with a co-publisher.

A co-publisher gives me options. I front all of the costs and keep full control of the content, marketing plan, and timing. With co-publishing, I get access to an amazing team of designers, editors, and team to distribute the book. It is the best of both worlds: the control of self-publishing with the distribution and team of a publisher.

I’m taking the bet on me.

And rather than start slow with the One Man Show, I jumped in by hiring a director, acting and performance coaches, a world-class playwright, a video team, musicians to add a score, etc.

I invested heavily in these assets.
I’m all in.

The path is less certain than me selling financial advice through education courses and content delivered at scale through memberships and programs. Yet it is more exciting, challenging, and fun for me.

And the good news is that it isn’t an either/or proposition.

I have found partners who have developed the technology to deliver content in a timely, relevant manner that is connected to balance sheets, income statements, and all financials. By collaborating, it will allow me to do what I do best, and deliver more value than I ever could before. (More to come on this…)

My money story is this:

Money is a means to utilize the value others provide so I can focus on creation using art, comedy, and entertainment. I’m investing in my vision by developing intellectual property.

If I were addicted to numbers on a piece of paper (net worth) like in my twenties, or cash flow from assets that I don’t relate to (portfolios) like in my thirties, I wouldn’t be excited, happy, or fulfilled.

I am choosing to develop assets most aligned with my Soul Purpose.

I knew this would temporarily reduce my financial certainty and cash flow. I could have gone slower and taken my time. But again, that would be thinking small and not aligned with how I want to operate.

Momentum matters.

I want to plant a seed of hope, connection, and expression in the hearts of one billion people using entertainment to educate and help people heal their relationship with money.

No small feat.

There is evidence this can happen though. But not exactly like the model and delivery I am called to. And evidence isn’t always available when we choose to live our Soul Purpose.

Our Soul Purpose is a combination of our values, abilities, and passion for the highest context of living- purpose. It is who we are when we are at our best, fully self-expressed.

When I chose to write and perform a comedy special around money, I felt alive. Stressed at times, often uncertain, and fulfilled throughout. It wasn’t about being comfortable or avoiding all risk, it was about doing what I love. It is about living a life I love.

This could seem to be at odds with my finances. And again, temporarily it is. But some assets produce immediate results and others take time to develop. When inventing a model, it is usually the latter.

Strangely, the time of my life when the most money came in regardless of what I did, the less happy I felt. It wasn’t the worst time. I felt much worse during 2008 as my net worth was lost while my real estate portfolio declined.

But the level of recurring revenue (a.k.a. passive income) to more than cover my lifestyle took a decade to build. It was a great accomplishment, but left me with less passion and excitement as the process became mundane and predictable.

This felt boring.

Don’t get me wrong, I was grateful for the abundance, just not fulfilled.

I was able to create economic independence following a faulty model in my twenties. It didn’t last.

I was able to create a more sustainable model in my thirties, but was losing the zeal for my work.

Now, it is about doing the most meaningful work with those I love working with. My assets are not stocks and bonds, but books and software. I am not investing in someone else’s vision, but my own.

This time around, it will be easier, and faster to regain economic independence. I get to take my Mental and Relationship Capital with me.

The years of building relationships allow for my vision to come to fruition through the ideas and models that I have discovered along the way. I have a quarter of a century of knowledge and relationships that have come to my aid.

This is about doing things in flow, which gives me energy, and therefore making an even greater impact—on myself and others.

What can I dedicate decades of my life to?
What work makes me feel alive and fulfilled?

These questions are guides in my money story, in my life story.

What do you want your money story to be?
Where do you want your life to go?

Are you living your Soul Purpose? If not, why not?
Do you carve out time to discover and develop your Soul Purpose?
Are you waiting to have the money first?

What is at odds with your Soul Purpose?
Investing in yourself?
Your childhood stories about money?
Your worries and fears if you can make it work or not?
Other people’s opinions or doubt?

What does Soul Purpose have to do with your money story?

Living your Soul Purpose is not about doing more things and adding more to your life. Usually, it’s about cutting things out of your life that aren’t aligned with your Soul Purpose.

But this can be hard when you feel trapped in the struggle of trading time for money, trying to pay off debt, and keeping your head above water.

The key here is to learn to be more efficient. Pay less in interest, reduce taxes, take underperforming assets and pay off high-interest rate loans. Find the room to breathe and take time for yourself.

This isn’t about working harder, but finding time to discover yourself.

One of my past clients was an accomplished dentist and an extreme crossfitter. He was a highly-accomplished, driven A-type who could get anything done. He had been working hard in his business for years.

But when he attended one of my retreats, he figured out more about his business just by meditating for a couple of days than he had over years of grinding in the trenches. He returned home and made several changes that simplified his life, freed up his time, and ultimately made him more money.

What is your ideal life?
And what’s the fastest, safest, most efficient way to get it?

It is easy to say money isn’t that important when cash flow is abundant.

Regardless of the phase of life you are in, now is the time to answer these questions and let your Soul Purpose be your guide.

You are your greatest asset.

Invest in yourself, discover your Soul Purpose, and live the life you love.

Know anyone else who could benefit from this?

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