4 Critical Life Lessons from a Serial Real Estate Entrepreneur

4 Critical Life Lessons from a Serial Real Estate Entrepreneur

6 min read
Paul Moore

Paul Moore is the managing partner of Wellings Capital, a private equity real estate firm.


After college, Paul entered the management development track at Ford Motor Company in Detroit. After five years, he departed to start a staffing company with a partner. They scaled and sold the company to a publicly traded firm five years later.

After reaching financial independence at the age of 33 and a brief “retirement,” Paul began investing in real estate in 2000 to protect and grow his own wealth. He completed over 85 real estate investments and exits, appeared on HGTV’s House Hunters, rehabbed and managed dozens of rental properties, built a number of new homes, developed a subdivision, and started two successful online real estate marketing firms.

Three successful commercial developments, including assisting with the development of a Hyatt hotel and a very successful multifamily project in 2010, convinced him of the power of commercial real estate.


Paul was a finalist for Ernst & Young’s Michigan Entrepreneur of the Year two years straight (1996 & 1997). Paul is the author of The Perfect Investment – Create Enduring Wealth from the Historic Shift to Multifamily Housing (2016) and has a forthcoming book on self-storage investing. Paul also co-hosts a wealth-building podcast called How to Lose Money and he’s been a featured guest on 150+ podcasts, including episode #285 of the BiggerPockets Podcast.


Paul earned a B.S. in Petroleum Engineering from Marietta College (Magna Cum Laude 1986) and an M.B.A. from The Ohio State University (Magna Cum Laude 1988). Paul is a licensed real estate broker in the state of Virginia.


Email [email protected]
Twitter @PaulMooreInvest
How to Lose Money podcast

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I said it aloud while glancing in the mirror this morning. “My hair is really getting gray. Or should I say, silver?”

Why do I look older than I did last week? I wondered to myself.

I’m just finishing a wonderful 12-day vacation with my family on Sanibel Island, in Florida. The sun has darkened my face this week, which has made my “silver” hair look even whiter. A reminder that I’m no longer in my 20s.

Or 30s. Or 40s. I passed the mid-century mark several years back. And as of next year, I’ll have been an entrepreneur half of my life.

I’m gonna celebrate! Half or more of my life…

…No longer working for the man

…No longer getting a W-2

…No longer punching a clock

…No longer being denied a mid-afternoon snooze or the chance to go to go fishing with my son on a weekday

…And so many more benefits!

But my life as an entrepreneur has not been all rosy. (Surprised? Seriously?).

Since I quit corporate America in 1993, it has meant…

…The end of great health insurance (I spent $41,000 for the birth of my fourth child)

…Using my home equity line to make interest payments on … my home equity line

…A few hasty resume rewrites (I’ve nearly thrown in the towel more than once)

…My young daughter asking me when we’d be “rich again” so we could go on vacation

…Wondering what it would be like to get my 30-year pin at Ford Motor Company this August 1st, and retiring with a fat 401K to start a second career

Lest you think I’m second-guessing my decision to be an entrepreneur today – I’m not. I wouldn’t have it any other way.

But as I discussed in a recent post on my lessons from the school of hard knocks, and as I look at how gray my hair really is, I can tell you that this path has not been easy. Fun, exciting, profitable… but more often than not, challenging.

So one of my great joys is the opportunity to pass along some of my life lessons to my children, younger friends, and BiggerPockets readers. Here are a few more.

Related: Learn from Warren Buffett Failures & Create a Moat Around Your Business

Lesson #1: Make Giving A Priority Now And Watch For A Windfall Later

It is truly more blessed to give than receive. And it’s more fun to see the delight on the recipient’s face than to buy that next big toy.

My wife and I have long had a practice of giving ahead of our increase. This risky strategy has paid off more than once. Put simply, we don’t wait until we have more success to give generously. We try to give outrageously before we can afford it.

I’ve told the story of how we went from almost $2 million in the bank to $2.5 million in debt in the decade leading up to the real estate crash. With our backs against the wall, my wife and I decided to start giving as if we were making about half a million per year.

After a lot of prayer, a lot of hard work, and a handful of miracles along the way, we were completely debt-free within 13 months.

Now, I don’t believe that giving generously is a magic bullet for every situation. I think heart motivation plays a role. And like I said, a few miracles along the way.

Lesson #2: Discern The Difference Between Facts And Truth — Then Practice Thanksgiving All Year Long

There has been so much written on the topic of thankfulness that I don’t need to belabor it. Books, research, movies, and ancient scrolls tell us what we often forget: We were wired to be thankful.

This hit home for me some time ago when I realized that there is a difference between truth and facts. (Huh?) There really is a difference between truth and facts.

  • It was a fact that our marriage seemed doomed because we couldn’t seem to get along. For years.
  • It was a fact that my wife and I were $2.5 million in debt, spiraling into the worst recession since the Great Depression.
  • For you, it may be a fact that you feel enslaved, working for the man in a j-o-b. You may have been, up to now, unable to get that break to jump ship and make it as a real estate investor.

But here is the truth: where I was in these stuck places, and where you are today, is not the end of the story.

And often the link between where you are now and where you want to go is the practice of thankfulness.

I also call thankfulness “celebrating in advance.” If life and business aren’t working like I want, I can choose to “celebrate in advance” that there is something better ahead. And I can be thankful (to myself, God, my spouse, my employer, etc.) that there is a future that is better than my current experience.

And thankfulness leads to peace and joy. And peace and joy directly (and indirectly) lead to lower stress, better health, better decisions, better relationships, and a better outcome.

Trials will either make you bitter or make you better. Often, thankfulness is the difference-maker to get you from point A to point B.

Lesson #3: Don’t Miss Now

This is a song title by one of my favorite bands, Downhere. (Their lead singer sounds just like Freddie Mercury from Queen. You should check them out.)

We all know better. We’ve all seen the movies and read the divorce statistics. We’re aware of the enormous crash-and-burn rates among kids of the super-wealthy and successful.

But it is so easy to fall into this trap. To say, “I just have to focus all of my energy and attention this month, or year, on my business. Then I will focus on my wife, kids, and causes I’m passionate about.”

It’s typically a lie.

I “retired” in 1997, at age 34, when I sold my entrepreneurial company to a public firm for a few million dollars. I had been running hard and had allowed my relationships with my wife and kids to suffer. But now it was time to plug into them and be the great dad and husband I wanted to be.

I didn’t do that at all. I had gotten my self worth from my job, and drive was second nature to me. The next few years were miserable. They produced some of my worst memories as a dad and husband. And I made the worst investment decisions of my life, blowing much of the capital I had.

We have a very limited time on this earth, and that becomes more apparent as you get older. And we have a very short time to enjoy our spouses, children, and other significant relationships. Our kids (or parents, friends, etc.) will never be this age (or at this stage) again, and the time to love and enjoy them is now.

And if you’re married, the time to have a great marriage is today. I have not one, but two successful friends who suddenly got dementia in their 50s, and they will never get to enjoy retirement with their wives.

One of them, a millionaire dozens of times over, was just buried this spring. He did not have the marriage he could have (though his wife is amazing), and his relationships with all of his children seemed strained.

I’m telling you what I’m telling myself: Don’t miss now!  

Lesson #4: Create Moats Around Your Life

Warren Buffett, in a letter to investors, said, “A truly great business must have an enduring ‘moat’ that protects excellent returns on invested capital.”

There are dozens of ways to build a moat around your business, real estate ventures, and life. I wrote about this in a recent BP post, but I want to revisit it here.

What boundaries exist — or can be created around your business, property, or life — to protect you from invaders or competitors?

In my previous article, I told the story of how our company purchased a townhome community in Lexington, Kentucky — a city that has erected moats around itself through its economic development policies — and how we are working to establish the moat of a connected community to assure our residents want to stay.

While thinking about moats, I’ve been asking myself how good of a job I’ve been doing erecting them in my personal life.

What are you doing to create personal moats? Here are some ideas to get you thinking about this:

  • How are you building moats to protect your marriage or significant relationships from predators?
  • What are you doing to build a moat around your children to prepare them for life and guard them from harm?
  • Are you erecting moats around your dreams? In order to follow your big yes, you will need to say a thousand nos to distractions along the way. This is the path of the truly successful.
  • Have you built moats to protect your health and to create downtime and margin in your life?


My path to a successful life and business has included a lot of important lessons. I hope these few will help you along your journey.

I’d love to hear from some of you.

How are you making giving a priority in your life; moving beyond the facts and celebrating Thanksgiving all year long; not missing now; and building a moat around your life? Share your own wisdom below!