“There is no end to education. It is not that you read a book, pass an examination, and finish with education. The whole of life, from the moment you are born to the moment you die, is a process of learning.”
— Jiddu Krishnamurti
I was 26 years old when I did my first real estate investment property.
It was a single family house in Billings, Montana.
I moved there to be a youth pastor years ago.
Since then, I’ve upped my portfolio to over 2,500 multifamily units.
We’ve also raised around $50 million.
Today, I wanted to share a few of my secrets.
Let’s jump into it!
1. Wins and Losses
First of all, I think it’s important to talk about wins and losses.
We all have things we do well and things we don’t.
Even when you do things well, things can go wrong and trip you up!
For example: We’ve had a few deals go wrong because we didn’t have to fix the debt.
If I were to do those deals over, I would get involved with more deals with fixed debt.
Also, deals with more experience on the operator side of things.
We did have a black swan deal recently where we saw the rates rise ridiculously fast.
But those are not common at all, and we definitely learned our lesson in real estate deals.
If we would have learned those lessons sooner, we would have saved ourselves a lot of trouble.
2. Diversify Your Investments
One of the mistakes I see a lot of investors making is only focusing on real estate.
Now, don’t get me wrong.
Real estate is great.
I’m a huge real estate fan.
But right now, the tax benefits are not as good as they were a few years ago, thanks to the Tax Cuts and Jobs Act.1
That may very well change, but it’s not a guarantee.
At the present moment, though, cash flow is the thing that really allows you to quit your job.
It also allows you to retire early.
Stocks don’t really let you do that.
You should look into investments like oil and gas or other private business deals.
Those have great cash flow!
Real estate does pick up sometimes, but generally, it’s not great for cash flow.
Interest rates and insurance costs have also gone up.
If I were to start over, I would get into more investments as soon as I could.
3. Avoid Single Family
The last secret I want to share is to avoid single family investing altogether.
I got my start in single family, but if I were to do it over again, I would not have chosen that path.
I had four single family houses, and it was a lot of work to manage all of them.
They also didn’t really provide cash flow.
Remember: Cash flow is key!
Single family can eventually build wealth, but only after about 10-15 years.
You still have to continue working.
If you want flexibility, which most people do, it’s not a great fit for that.
It also does not pass the scalability test.
If you were to scale your single family investments 10x, you would be overwhelmed with work.
That type of asset doesn’t scale well at all, especially if you’re a passive investor.
I also have one piece of bonus advice for you before you go:
If I was going to start over again, I would pay money to get in the best rooms I can.
This can vary depending on what you can afford.
Some masterminds can cost up to $50,000 just to get in.
But if you can swing it, go!
It will allow you the opportunity to be around people who are pushing themselves to grow.
That mindset can and will rub off on you.
Mastermind groups in particular, according to the American Journal of Pharmaceutical Education, help members receive psychological support, encouragement, and inspiration.
They can also offer suggestions for solving problems and resources to manage challenges.2
Now I want to hear from you!
If you were to start your investing journey over, what would you do differently?
Let us know in the comments.
Before you leave, make sure to check out our special report about inflation investing. It shares the best choices to invest during an inflationary environment.
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Disclaimer: I am not your investment advisor. This is for educational purposes only. I am not giving specific advice on what you can do. I am simply giving my opinions.
Works Cited
1. “Economic Effects of the Tax Cuts and Jobs Act.” Congress.gov, April 7, 2025. https://www.congress.gov/crs-product/R48485.
2. Jayesh Parmar, David Fuentes, Jeremy A. Hughes, Grace M Kuo and Annesha White. “Leveraging Collective Expertise, Wisdom, and Guidance through Mastermind Teams.” American journal of pharmaceutical education (2024): 101345 . https://doi.org/10.1016/j.ajpe.2024.101345.
