My Grandpa's Advice Made Me Millions (And Got Me The Girl of My Dreams)

When I was a kid growing up, my grandpa used to tell me I could be anything that I wanted to be. I'm sure many of you heard something similar from people important to you growing up.

Call me a dreamer. Call me crazy. Call me someone with level-one autism who takes things too literally sometimes, but I'll be damned—I believed him and lived the vast majority of my life under the belief that I could do, have, and be anyone and anything that I wanted.

The Pattern of Achievement

The interesting thing is, for all intents and purposes, anything that I've really set my sights on and gone after, I've gotten. I don't say that to sound arrogant—I'm not special. I didn't have any special advantages growing up.

But when I look back on the things in life that I truly wanted and went after, I've made them happen:

• When I moved to Texas in my early 20’s with nothing more than a high school proficiency exam from California and saw the campus of Southern Methodist University, I said I'd get my graduate degree there—and I did.
  

• When I said I wanted to get into politics (a passion of mine at the time), even though I didn't have connections in Washington, a college degree of any kind at the time, or any experience—I found a way in. 10 years later, I was Managing Director of the US Chamber of Commerce and my teams and I had raised a hundred million dollars in political fundraising.
  

• When I wanted to get into private equity, I was told the odds were stacked against me. I was in my earlier 30s, didn't come from an investment bank, only had an online undergrad degree at the time, and had no real investing experience to speak of. Three years later, I was CEO of a PE-backed company and have worked with multiple investor groups since. Now I have my own venture company where we help lead growth in exchange for ownership.
  

• Perhaps the best example is my relationship with my wife. She was gorgeous, fun to hang out with, shared many of the same interests and hobbies as me, but as her dad told me several years later when I asked for permission to propose to her, "You know you loved her before she loved you." True, but 10 years later, here we are.

This has been a pattern in my life. And when I sat down to think of examples to the contrary, I really couldn't. From college degrees, to new jobs and relationships, to raising a family on a Mexican beach, when I set my sights on something and really go after it, I make it happen.

Hard Work Behind Success

Don't get me wrong—none of these things were easy.

To get my graduate degree, I had to go to school full-time to earn my undergrad, while holding down a growing career, earn my way into SMU largely through my career track record, and then power through their executive MBA program. I graduated summa cum laude and was invited to Beta Gamma Sigma.

Getting into politics wasn't any easier. I nearly missed my chance by bombing my first interview at the Chamber, but I made up for it literally on the walk out the door with a political discussion based on hundreds of hours of self-study in politics—which left the manager virtually no option but to give me a shot. Then, to keep my role, I had to learn how to sell, which I knew nothing about and frankly, didn’t want to do. (Kind of ironic now.)

Getting into private equity required taking on networking as a full-time job, with more breakfasts, coffees, lunches, and dinners than I can count. I left every meeting with an ask for introductions to two other people because I knew that was the best way to build my network. This went on for years.

As for my gorgeous wife, we went on more "friend dates" than I care to admit. We jokingly look back at my bank statements because I could tell you exactly what days she was working at her bar—my credit card rang up charges every time she was there. But I managed to navigate through the friend-zone and win the girl of my dreams.

The same has been true with every big goal I've had. It's never been easy. But I've never missed the mark.

And I’ve thought a lot about why that is.

Two Fundamental Truths

Through all these experiences, I've come to believe two things:

1. I'm a lucky guy. I've had my fair share of lucky breaks and opportunities along the way, and I'm not discounting that. So let me get that out of the way.
   

2. There is nothing that I truly want that I can't get if I'm willing to put in the work.

The Formula for Achievement

As I've gotten older, I've had the opportunity to look at these patterns and realize what I think makes this possible.

And that's the real reason for this newsletter—I want to share why I have the degree of confidence I do that when I set a goal in my mind, I'm going to attain it.

Because I've come to believe it has very little to do with me, and has everything to do with these 3 things.

1. Having the Courage to Dream

Too many people sell themselves short out of fear of failure, or more accurately, fear of what other people will think of their failure.

So they don't dream. They think small, believing that's the best way to maintain a high batting average.

But the reality is: you get what you set your sights on.

If you set your sights on small goals and small dreams, you will get small wins. If you have the courage to dream bigger, that's what you're going to attain.

Having a bigger dream doesn't change your batting average—it changes how far the ball flies.

2. Being Crazy Enough to Believe Your Dreams

I'm not talking about those fleeting thoughts and wishes that I know I'm not willing to put in the work or sacrifice to attain.

Would I love a billion dollars? Sure. But I'm honest enough with myself to say I'm probably not willing to make the sacrifices necessary to get it.

But when I do have a dream, when I do lock it in and can visualize it, I believe it is possible.

I believe if anyone else has attained it, there's no good reason I can't either. If somebody else has figured it out, I can figure it out. If somebody else has earned it, I can earn it.

That's just a belief system, which is a choice.

3. Overachieving To Get It

I go after it with everything I have. Even if there's a chance the initial route to get there is wrong, or someone else who attained the same thing had an advantage I don't, I lock in and methodically execute and push through at a level that some may consider obsessive.

I make my goal non-negotiable. I take quitting off the table.

I may look for alternative approaches, experiment with different paths, ask for help along the way, or pivot if needed.

But the destination doesn't change.

The Ultimate Realization

Looking back and realizing this pattern, I've come to understand why, when I think about the goals I've had, I can't think of one that I really locked in on and haven't achieved.

It's the courage to dream it up, the craziness to believe it, and the willingness to invest the work, time, and energy—taking quitting off the table.

When you approach life this way, fear of failure becomes irrelevant. Success is all but inevitable. It's just a matter of time.

You Don't Have to Be Special

You don't have to be special for this to be true.

In fact, you could be a kid who had plenty of things stacked against them, someone who would've never been voted "most likely to succeed" in high school, and had any number of disadvantages at the starting line...

And finish with a life that's better than anything you could have imagined—living on the beach of your dreams, with the partner & family of your dreams, doing what you love to do, with achievements no one else in your family has ever reached.

I know, because I feel like that's my life in a nutshell.

I share this for anyone who's reluctant about putting themselves out there and going after what they want, or for anyone who's in the process of doing it and feeling that resistance.

Dream big. Believe it's possible. Work relentlessly. Don't quit.

Adios,

Ray

P.S. - Next week we get back to sales and marketing advice. 😉