We all know a terrible boss. And we all hope we’ll never be that terrible boss. But as your real estate investing business grows, how do you avoid becoming the next Michael Scott?It’s not about dynamic speaking or motivating emails. It’s about your leadership philosophy and the foundation of your team building. If you want to be a great leader, build your team on three pillars: truth, daring, and caring.

Living (and leading) this way leads to living a regret-free life. So let’s explore each of these three pillars.


It sounds cliché, but it’s 100% true… when it comes to achieving success, you need to start by finding what you’re passionate about (and what you’re good at).

I was raised to hide certain facts about myself. As a kid, if someone hurt my feelings I wouldn’t necessarily tell anyone because that was considered being too sensitive. It goes back to wanting to fit in. But think about how stuffing our feelings in a box causes us to hide so much from our partners, our customers, our coworkers, and ourselves.

When we live this way, we’re like a billiard ball universe, bouncing off of one another. We’re never vulnerable, so we don’t have true connection. And when we’re missing that deep connection with people we try to satisfy it in food or alcohol or caffeine or entertainment.

The antidote to all this superficial connection is truth. We need to start revealing our experiences first to ourselves, then to others.

Be Honest with Yourself

Start by tracking your physical state and your emotions. Pay attention to the energy level in your body. Be aware of your physical discomfort and try to exercise or eat something healthy in response.

Once you’ve adjusted to tracking your body, move to the ninja level or tracking your feelings. Notice when you get defensive. See if you can track it back to a feeling of criticism. That will allow you to choose how you respond rather than just reacting.

This level of tracking is a black belt leadership move. If you’re a leader and you’re not aware of what’s happening in your body and your emotions, the people you’re leading aren’t likely to trust you. They want a leader who is in touch and understands what’s going on.

Be Honest with Others

Once you’re honest with yourself, it’s time to be honest with others. This doesn’t mean you put every detail of your life on the table for anyone to see. You need healthy boundaries. But you should also be vulnerable even with your employees. Sure, being that authentic is scary and you might lose some relationships. But those are the relationships you were meant to lose, and it will help you attract the people who really want to be around you.

Being honest about your own struggles and mistakes is also how you earn respect. Your partners, employees, and investor friends don’t just want to hear about how great real estate is and how much money you made. They want to learn what you learned from the wrong turns you took, not just the right ones.

The goal of your honesty isn’t just respect, though, it’s connection. And you can build that connection by tracking. When you’re talking to a colleague or friend who’s facing a problem, don’t just start suggesting solutions. Focus on listening and naming what’s happening. Repeat what you’re hearing back to see if you understand the core of the problem. Ask the other person to tell you more. Let the other person know they are being heard. Once they feel heard, you can move on to talk about the solution, and the conversation never gets heated.


The second pillar of a ninja leader is daring. This one is extra personal for me because when I was diagnosed with pancreatic cancer I needed a daring surgeon. The cancer mass was as big as a basketball and wrapped around my organs, and once my surgeon opened me up, it looked worse than he expected. But where 95% of surgeons would have closed me back up and told me I had a few months to live, my surgeon pressed on and saved my life.

That kind of decision-making takes daring, but instead so many of us live in a bubble. We’re afraid of rejection and failure and we let those fears stop us from being daring. And those small choices to protect ourselves add up over time.

At the end of our lives those choices that were made based on fear lead to regret. So rather than basing your decisions on fear, base them on a desire to give your everything and fully live. Suck all the juice out of the orange. When you live that way, you’ll find your edges.

Remember that everyone has different edges. Your daring decisions should be based on your values and they should be appropriate for you. If you’re making decisions based on what’s right for someone else, you’re still living in fear. Instead, live in freedom. Consider the worst possible outcome. Are you willing to handle that risk?

And being daring doesn’t have to be one massive step. Just start by doing one thing differently. Let’s say you want to get in shape but you don’t have much time. So instead of driving to the store to pick up the milk, walk or ride your bike. Let’s say you want to expand your real estate network. Go to one new meet-up. Take a step or two outside your comfort zone. After you accomplish that step, take another one. Peel back the layers.

Lastly, remember that this is about what’s right for you as a method of self-expression. Focus on doing this for yourself, and if you wind up with a new deal or a personal gain, that’s a bonus.


The third pillar, caring, starts with caring for yourself. Honor yourself and your limits. You’re human, and you can’t do everything. If you don’t care for yourself, you can’t care for others. You need self-care. It’s the cure for anxiety and self-doubt.

This applies to business and relationships too. If you don’t care for your business by doing your taxes, keeping your systems in order, and checking in on your employees, you’re going to lose that business.

This may seem obvious, but that’s one reason it’s a pillar—it’s critical to successful leadership.

If your only goal is to make money, then you’re going to forget to take care of yourself and your business. You’re going to struggle in your relationships. Make caring a priority.


If you want to grow your own ninja leadership skills, pick one of these three pillars (truth, daring, and caring) and write down one concrete way you’re going to work on that pillar. Then find someone to hold you accountable.


What ninja skills have made you or others you know better leaders? Give me a shout out below.

Be Daring,


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