Why a first-grader? Cuz I was watching one of my daughters who happens to be a first-grader and whom recently showed tremendous bravery.

Why a first-grader?

Cuz I was watching one of my daughters who happens to be a first-grader and whom recently showed tremendous bravery. I watched her step into her courage and felt an equally tremendous pride.

Before I get to that, let me back up a month or so…


When we were at Disneyland just weeks earlier, my first-grade daughter spotted a ride she wasn’t quite sure about.

It was the spinning one with swings.

My daughter decided to give it a whirl… literally. At the end of that first ride, she vowed she would never do it again. The ride scared her; she backed off.

She stuck to her word… until four weeks later when we were at the Orange County Fair. (Again, just a month after her first experience with the “scary” ride.)

My heart swells when I think about this moment. Call me a doting father.

As my family and I walked through the fairgrounds, we found the rides. My daughter spotted the same twirling swing ride and announced that she wanted to take a spin.

I was in awe. How courageous, I thought!

As we waited in line I watched my little girl’s face; she was thinking her way through her fears. She had done the ride before; it wasn’t exactly a positive experience; she was willing to give it a second go; she wasn’t sure what would happen; she climbed up in the seat anyway.

Guess what?

She loved it! She looks forward to the next time she gets to take it for spin! In fact, she can’t wait!

Maybe that’s because she was more familiar with the ride the second time around.

massey family disneyland 01

That got me to thinking.

If my daughter could work through her fears to conquer one that had her in its grips because of a questionable prior experience, why can’t we as investors and entrepreneurs do the same?

This is something I talk about in different episodes of my podcast. Here’s one… in case you missed it.


If you are new to real estate investing, you might be experiencing fears around some of the tasks involved in, for example, writing offers.

My question to you is… are you braver than a first-grader?

What I mean by that is can you work through your fears to do the tasks involved in real estate investing anyway?

It is the same process as I watched my daughter go through.
My question to you is… are you braver than a first-grader? Click To Tweet
Understand something. You are in control of your responses to your fears; they are self-made.

The great thing is that once you’ve worked your way through your first time doing anything, you can stop worrying about doing it wrong or something “bad” happening. (I promise you’ll make mistakes… but so what? Keep moving.)

There will be a lot of firsts if you stick with your goals:

  • Making your first offer
  • Writing your first Letter of Intent (LOI)
  • Creating your first purchase agreement
  • Negotiating your first deal to make a win-win for everyone involved
  • Raising your first $10,000 or $100,000… or first million dollars in private capital
  • The first time you hire an assistant, an accountant, CFO or any member of your team

Good news!

You can and will do every bit of what you need to get done if only you walk away from the negative voices in your head telling you that you can’t. That’s just fear talking.

Here’s another podcast episode that might help you over that hurdle. It’s on the power of positive thinking. Give it a listen!


If you are struggling with writing your first offer or LOI, I want you to remember something important…

An offer is only an invitation for a conversation!

That’s all.

Don’t make it more than it is.
An offer is only an invitation for a conversation! Click To Tweet
When you find a property you want to put under contract don’t wait. Get in there and make an offer. You can start with any number you want. Literally. Even a dollar. (I’ve done it.)

You want a conversation-starter? I double-dog dare you to open your offer at a buck.

Once you have put your written offer in with the seller, you have to follow up. It’s a conversation. That’s all it is!

You will speak; the other person will speak… and so on.

You cannot let your fears about talking to other people, to strangers, stop you from success. That’s another topic I cover in live events and in my podcast. So do lots of my guests. Here’s an episode from one of my recorded live events. It’s the first in a three-part series.


You want a sure-fire technique to help you deal with your fears?


It boils down to two simple questions you must ask yourself whenever you experience fear around doing anything new:

  • What is the absolute worst thing that could happen?
  • Can I live with that [outcome], and if not… what part of “that” can I live with?

By keeping it simple like this, you realize that taking the action that you dread so much isn’t going to kill you.

For example, let’s say you fear writing your first offer.

Ask yourself, “If I write this offer what’s the worst that can possibly happen?”

  • Will my life end? Um, no.
  • Am I still going to have food to eat? Quite likely.
  • Am I still going to have a car? Yes.
  • Is anyone going to get physically injured? Probably not.
  • Will it alter my life in a way that you can’t come back from? No.
  • If I write the offer, and I get out of my own way, can this action propel me forward so good things can happen for me? Bingo! Yes!

Follow that with, “Can I live with that?” and likely the answer will always be yes. However, if it’s no, what part or parts can you live with?

Conversely, if I were to ask you to jump behind the wheel of a high-performance Lamborghini and you’ve never driven one before, that’s a horse of a different color.

You’d ask yourself, “If I jump in here and drive this thing, what’s the worst that could happen?”

  • Could you die? Yes!
  • Could it literally wreck your life? Maybe.
  • Is it something that could bring harm to others? Possibly.

So the follow up would be for you to ask yourself, “What part of that could I live with?”

The short answer might be none of it and you shouldn’t get behind the wheel. However, you should ask yourself, “Are there things I could do to prevent bodily harm so I could actually give the car a really fast test drive?”

In that case, the answer is yes.

You could buckle up, use a helmet or take a driving-safety course and all sorts of things before getting behind the wheel. In short, you would educate yourself so you’d have a better chance at a satisfying and dare I say fun outcome. You would remove your fears even in this case.

When juxtaposed against truly frightening and even life-endangering actions, you can see how writing an offer or taking action steps in your real estate paths isn’t so scary after all.

You can move through your fears and step into your courage quickly just by asking yourself the two questions.

We can all do more!

It’s a funny thing about us human beings. We can be more, do more and achieve more than we ever thought possible if only we let go of our fears, get out of our own way and tell our negative thinking to take a hike. (Those voices are just our anxieties hollering out anyway.)

We also have to move away from people in our lives who are negative.

When it comes to this, ask yourself WHY you continue hanging out with negative people or people who don’t try new things or those who never take a risk in life.

If you only hang out with people who play it safe, there might be a reason. It’s a real safe bet that they will support your reasons for playing it safe, too.

Take a little risk in life…

Being a real estate investor inherently comes with a little risk… at least when you participate in higher-level deals. With higher risk may come a higher level of anxiety, but that’s okay.

You know what to do about it. Use the same technique I shared with you earlier in this article.

At the wholesale level there simply isn’t a whole lot of risk, and that’s why a lot of investors start there. If that’s what you’re wanting to get into… what are you waiting for? Start writing offers. What’s the worst that could happen?

You can start by taking our Deals at Discounts video course.

Need a little inspiration to help you get motivated? Read my book.

I started as a wholesaler and the book is about my journey, what I learned along the way, how I got beyond my fears and how I moved my own needle forward in my investing life… and how you can do the same!


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