Executive Letter #22: What I Wish I Knew When I Was Younger

This is a question I am asked frequently, especially from my team members who are relatively early in their career. And in part, this question was inspiration for creating The Grind, so I could try to distill my decades of business learning into clear actions that any of our readers could implement.

What do I wish I knew when I was in my 20’s, 30’s, 40’s? If I could go back and talk to my younger self, what would I say?

To an ordinary person, this might be an overwhelming thought, triggering years of regrets, missed opportunities, or misfortune.

Not me. 

First of all, I'd tell myself to start earlier. Even though I know that every hardship led me here, and I don’t regret a single moment along the way, there are certainly lessons I wished I’d learned earlier. I know that even if I’d heard those lessons directly from my future self, my hard head would still have taken just as long to truly learn and live them out. So the earlier you can get started, the better.

Maybe you’re like me. Or, maybe your head isn’t quite as hard. Regardless, let me give you some further insight into what led me here, and how you can avoid some of the mistakes I learned from the most.

Build a Team You Can Trust

I've done every job in this company and I find it invaluable to educate myself and my team on every aspect of what makes things run efficiently. Building a strong team and bench strength is essential, and I wish I had got started earlier surrounding myself with smart people, educating myself better, and seeking advice from mentors.

I’ve spoken to you several times now about how important it is to surround yourself with people who are smarter than you. I’ve found smart people to be an invaluable resource, especially for someone like me who never went to college or business school. 

Today, I want to share another story about why you can't skimp on a good team.

You may have heard in a recent podcast from my son Chris that early on in his turnkey days, he worked with a property management company whose model was structured in a way that had everything funneling up to one central property manager who oversaw it all. She managed leases, move-ins, move-outs, rent issues and collections, as well as maintenance.

Until she didn’t.

One day, she ran off with the deposits and rent money of all of the residents they had in their system, and that company was left to pick up the pieces, paying out vendors and investors out of pocket. They could no longer trust their systems, because often a resident did pay a deposit or a month’s rent but since they had paid in cash the property manager hadn’t reported it, keeping it for herself.

There were a lot of lessons we learned from watching that fiasco—including the decision to never accept cash from residents so the same thing wouldn't happen to us.

From then on, we knew we needed systems that were meticulous, recording every transaction down to the penny; and I knew I needed a team who would care about the details and a bench full of people who could keep things running.

My trust is hard-earned for a reason. But once you have it, it’s because I know I can trust you with some of the most precious resources we have in our company: residents and investors.

Think Fast, Decide Slow

Because I’m an entrepreneur—someone whose drive is to be bigger, better, and first—I’ve played an active role in every business enterprise I’ve ever been a part of. Perhaps even a hyper-active role. I like to get in the weeds, know all the numbers and details, because that’s how I know it’s being done right.

Some people would call that mentality micro-managing. I don’t deny that I’m “micro” with my focus at times.

So, the hard lesson has been to know when to lean in and when to step back. When to trust my team and when to trust my gut. That’s not an easy lesson to learn. It takes plenty of time and plenty of mistakes.

The biggest mistake has been hasty decisions. When you feel like everything is on your shoulders, you might not take the time necessary to think through your steps. You leap, because time is money. Sometimes leaping has been the best thing I’ve ever done. Sometimes, it puts things at risk of falling apart due to making decisions too quickly.

The second biggest mistake has been the risk of burnout. You can’t possibly be everywhere all of the time, but boy have I tried. And though I have more energy than most—especially for someone my age—I have my limits. Trying to deny that I do sets a bad example for my team. After my heart surgery 9 years ago, I had to learn to take better care of myself and slow down a little when needed. 

Finally, another mistake is missing out on an opportunity to develop your team, to invest in their learning and growth. It’s been a gradual process, but I’ve been able to trust my team with more and more of the details, and it’s led to an incredible group of thinkers and leaders running this company alongside me.

You Will Amount to Much More Than You Think

When I was young, I was told that I wouldn’t amount to much. The adults in my life—my family, my teachers, and my early managers—didn’t have faith in my potential.

My time in high school sports was cut short because people around me thought that I was best spending my time in ROTC, preparing for a war I never fought in. Then, in my adult years, I heard more discouragement from people around me who didn't encourage my ambition.

As hard as it was to hear those messages over and over again, I never let them stop me. If no one had faith in me, I’d have to have twice as much faith in myself. It came across as overconfidence or arrogance perhaps, but it was an attitude I had to adopt to propel myself past everyone who doubted me.

I still remember when my mother was still alive and how overwhelmed she was when she first visited REI Nation’s offices. She couldn’t wrap her head around just how we bought so many houses, let alone renovated and sold them! That moment meant a lot to me, but I still wish those other family members, teachers, and early managers could also see what we've accomplished here and the potential still to come.

I can believe in the potential of my team because I know firsthand how far a person can grow. With support, with words of advice, with professional development, and the strong positive affirmation of people believing in you, you can achieve whatever you wish.

Commit to The Grind

I’ll leave you with one final lesson I hope you take to heart: there’s no such thing as “luck.”

From the outside looking in, people might think we have it made. That we always knew what we were doing, and that things will continue to come easily to us. 

The idea of anything coming easy to me makes me laugh. You don’t get lucky with an eighth grade math education.

Take pride in the hard work that led you here. Wear your grit on your sleeve. Why? So that no one could say it was luck. You and I both know better than that.

Until next time,

Kent Clothier
Chief Grind Officer