346: David Osborn: What I Learned About Life and Business Founding 50 Companies and Making Millions

After sticking out his thumb and traveling the world, David returned home to Austin, Texas broke and unemployed, at the age of 26. Though his travels may not have yielded wealth, they instilled the key motivation that he brings to every part of his life to create it — freedom.

Through this intention, David began to test his entrepreneurial merits alongside his business-partner mom in the world of real estate. The results were nothing short of remarkable. In less than 10 years, David would go on to build one of the top real estate brokerages in the world, founding over 50 companies.

Yet, more than anything else, the inherent freedom derived from his success awards him the time to focus on the importance on what matters most: being a proud father of two beloved daughters, a son and husband to the wonderful and talented Traci Osborn.

Today, still rooted in his boundless sense of adventure, David continues to travel the world not only to be enlightened by new experiences, but to share his insight and expertise with others so they, too, can truly be free.

Favorite Success Quote

“If you go to work on your goals, your goals will work on you. If you go to work on your plan, your plans will go to work on you. Whatever good things we build end up building us.” ~Jim Rohn

Key Points

1. Create Your Vision and Get to Work on It 

Most people are simply coasting through life.

They live each day in a reactive mindset, allowing circumstances and the whims of others to control their emotions and outcomes.

And most people are miserable.

They are uninspired, financially and emotionally poor.

But you don’t have to be like most people.

The first step to breaking out of the mold that society has cast you into is to take responsibility for your future and make the major definite decision about what you want.

Who do you want to be? What do you want to contribute? How much wealth do you want to accumulate? What is your plan for achieving it?

Creating a vision for your life and achieving that vision is possible.

But it will require you to think differently, it will require that you make difficult decisions, and it will require that you put in the work.

But ten years from now, you will surely arrive…

The only question is who will you arrive as?

Will you be the man that society wanted you to be?

Or the man that you want to be?

2. You Have to Beat Your “Hopium” Addiction

Most entrepreneurs suffer from a strong addiction to a sinister substance that is the insidious destroyer of goals and dreams.


This drug isn’t something that you snort, inject, or smoke, but rather it is a mindset that permeates every aspect of your life and (if you are not careful) can destroy every aspect of your life.

You see, entrepreneurship is challenging, and it requires that you have a positive outlook and a strong mindset.

However, this mindset often leads many entrepreneurs to make assumptions and hold unfounded beliefs about the future of their lives and business that simply aren’t based in reality.

They get overly excited about what might come to pass, they put too much emphasis on what is happening in their business right now and not enough on the possible downsides that could happen in the future.

This dangerous addiction blinds many entrepreneurs to the reality of the business world and causes many fortunes to be flushed down the drain.

If you want to wean yourself off this potent “substance” the first step is to cultivate a sense of positive skepticism.

This does not mean that you approach every deal, hire, or project with a negative attitude, it simply means that you look at it for what it is and ask yourself “Where will this go wrong”.

For example, if you are expanding your company and opening up a new branch, before you sign a $20,000/month lease, ask yourself “How could this decision negatively affect my financial future and stability.”

After some careful thought you realize that this new territory has not been proven yet.

You only have one agent and have no idea how your new branch will perform.

Therefor you make the decision to run a 90-day trial period with no branch location.

You meet up with your representatives and agents at local coffee shops, and wait until they have proven results.

Once the cash flow becomes positive, then you can sign a lease for an office building.

3. Become a “One-hundred Percenter”

The first step to truly living a life on your terms, a life by design, an extraordinary life, is to become a “100%er.”

This grammatically incorrect (yet wildly powerful) term simply means that 100% of your monthly expenses are covered by passive income.

You could get into a car accident, or lose your biggest client, or sell your house and go backpacking across India and you would never have to worry about finances because 100% of your expenses are covered by passive income.

This is a powerful goal that most authority figures on money and financial freedom do not teach.

Who cares how much you can earn if you are constantly living in fear knowing that one bad deal or one lost client could result in a tumultuous end to your financial income.

Your #1 goal for the first part of your financial life should be to build up enough passive income that you never have to work again.

Once this goal is achieved you have true freedom.

You can sleep in every day, watch reruns of loony tunes in your underwear and play xbox for hours on end (not an outcome we recommend).

You can dance your happy tail across South America.

You can continue building wealth and growing businesses.

Or you can devote more time to your faith and your family.

Becoming a 100%er means that you can do whatever you want because you have true financial freedom, and the quicker you can achieve this goal, the quicker you will be able to live a life on your terms.

4. Real Talent Cares More About Upside than Income

Your goal in business should be to “fire” yourself and hire people who are better at your job than you are.

Your goal is to build an empire.

And to build an empire you must become a master at finding and hiring talent.

And with this job comes one critical misconception.

Most entrepreneurs think that great talent cares only about the income that you can offer them, but in truth, talent cares more about upside than anything else.

Ok, so their base pay is only $50,000  a year…

But what is their long term potential when you include bonuses, equity, and commission?

If you offer enough incentives, you will attract incredible talent into your business.

But you have to learn how to create contracts that build up “golden handcuffs” offering your new hires the ability to earn as much as they want… provided that they are earning you even more income in the process.

5. Constantly Grow and Educate Yourself  

The key to all success in life lies in education and massive action.

If you are not constantly expanding your mind, skill sets, and patterns of thought, then you are contracting them.

And if you are not constantly taking action on the new information that you are learning then you haven’t truly learned anything at all.

Your first priority in life should always be to expand your knowledge and skill sets so that you are equipped to face whatever challenges life might throw at you.

From finances to health to relationships, expand your mind and your reality will follow.

David’s Book

Wealth Can’t Wait by David Osborn

Influential Books

1. As a Man Thinketh by James Allen

2. The Miracle Morning by Hal Elrod

3. The ONE Thing by Gary Keller

Connect with David Osborn


Next Steps

We’re on a mission to impact a million men with powerful life changing content. If you enjoyed this article, please share it with your friends on your preferred social network on the left. I spent a ridiculous amount of time creating this article for you and with your support, we can impact the world together.

Want to become the strongest version of yourself?

Then click here to get a free trial to my elite community of 800+ high-performing men, The Secrets of the Top 1% of Men. Not only will you get tapped into your own “band of brothers”, but you’ll also have access to some of my best content and training as well as bi-weekly group calls with my team of coaches.

If you’re ready to push the boundaries of what’s possible in your life and become the man you’ve always wanted to be. This is the fastest way to do it.

The Times Have Changed. This is the Way Forward in 2024.

Here’s how I can help in my new FREE training on becoming a stronger Grounded Man:

1. The new path for men that creates a purpose driven life and doesn’t require you to lose your personal power, put women on a pedestal or sacrifice your goals.

2. Why men consistently settle and ignore the most important areas of life like the quality of their intimate relationships, social life and happiness and how to optimize all three without sacrificing professional growth.

3. The biggest mistake 97% of men make that breeds loneliness, breakups and emasculation that is absolutely reversible with this counter intuitive strategy.