How 'Fake It Til You Make It' Fails Entrepreneurs

A person wearing a black mask

How 'Fake It Til You Make It' Fails Entrepreneurs

What drives entrepreneurs to keep expanding and building beyond initial success?

It’s funny—my wife and I just got back from lunch, and I was saying, “What if we just paid out everyone on our team, kept things as they are, and didn’t acquire any more land or houses?” She made a good point, reminding me that many of our properties will pay off in seven or eight years.

But honestly, I think the real reason we keep going is that we’re entrepreneurs; we have a growth and building mindset. Without that drive, we probably wouldn’t have built any of this. If I didn’t have that mindset, I might’ve stayed in the military or kept my W-2 job, letting someone else set my schedule and dictate my life.

But that’s not who we are as creators, builders, and visionaries. We keep pushing forward—expanding, hiring, entering new markets, starting coaching courses, podcasts, YouTube channels, and even considering TikTok. There’s always something to do. As the saying goes, “Idle hands are the devil’s playground.” I don’t enjoy sitting around; I’d rather keep building.

How does time blocking help entrepreneurs reach their goals?

One of the biggest lessons I’ve learned is time blocking. When I was in the military, my schedule was intense. I had to be on base by 6:00 AM for physical training and often couldn’t leave until 6:00 PM. Add to that a new baby, a recent move across the country, and a brand-new marriage. It would’ve been easy to say, “I don’t have time to start a business.” But my goal was to eventually leave the military, so I had to find that time.

I committed to getting up at 4:00 AM six days a week, blocking out two hours each morning to work on my business. While I couldn’t make calls during those hours, I could email sellers and buyers and message them on Facebook. Those two hours each day added up—12 hours a week, 48 hours a month. Over a year, that time was crucial for building my business.

It was one of the best decisions I made. I’d be exhausted by 9:00 PM, but that early morning time, free from distractions, made all the difference. Even now, when I feel overwhelmed, I still get up at 4:00 AM. Those two hours, when the phone isn’t ringing and the kids are asleep, are invaluable. You just have to find the time.

What lessons can business owners learn from early successes and failures?

There have been so many lessons. I remember hearing Tony Robbins say, "When we win, we party. When we fail, we ponder." I was winning a lot—I was still in the military and had just started buying and selling land. I’d buy land for $285 and sell it for $5,000 or buy for $500 and sell with financing terms. After ten or twelve successful deals, I’d made a couple hundred grand, and I thought everything I touched would turn to gold.

I stopped taking precautions. I’d see a piece of land, decide to buy it at a third of its value, and skip steps like title insurance. Then came the mistakes. One property turned out to be a huge crater; another had a title issue. I had buyers lined up, but these problems surfaced after I’d bought the land. My arrogance caught up with me, and I realized those steps are there to protect you from bad investments.

This was one of many mistakes, but I learned a lot from it. I dug myself out of the hole, and now I teach others to avoid the same pitfalls. Looking back, I’m grateful it happened.

How does tracking ROI help measure company and team success?

As far as metrics go, if I had to narrow it down to one metric to track company success, I’d focus on return on investment (ROI). We need to know exactly how much we put out to get a return and what that return is. Currently, across all our companies, for every dollar we spend, we make about $3.95 back.

This metric also includes investments in people. Every team member is an investment, and if they aren’t bringing a positive ROI, they may be a burden. In those cases, it’s important to either find them a new role within the company or let them go. We recently let go of an employee who no longer fit with our culture, and we did so with a severance package. It wasn’t a negative thing; it was just the best choice for the company and the individual.

Why should business owners prioritize intentional networking over casual connections?

I’m very intentional about networking. I don’t attend random networking events; I go specifically to speak or learn something valuable. This podcast itself isn’t a random networking event; it’s intentional networking between us. I’m even starting my own mastermind. It’s incredibly powerful. Years ago, I started a real estate meetup, which is still growing, and it led to hundreds of thousands of dollars in business. So, while you can begin by attending events, I believe you should also consider creating your own.

*This interview has been edited and condensed for clarity.*


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