As a President’s Scholar at Southern Methodist University, I was fortunate enough to have a full scholarship along with access to dignitaries and business leaders.


Al Casey was one of those leaders.

And he happened to be teaching a class on leadership. I was nothing but fascinated by how he -- a real-life CEO -- made decisions.

He was the CEO of American Airlines.

He was Postmaster General of the United States. He had a million employees, deciding things like when to increase the price of a First Class stamp.

He ran the Los Angeles Times, too.

At the time, I couldn’t imagine what that was like.

Al bought and sold companies, had dinners with Presidents, and regularly met with famous people that I only read about in the Wall Street Journal.

Me, just being a kid, had nothing to offer him. I didn’t want to waste his time because -- clearly -- he had other things to do besides teach a class once a week.

But, there he was, fifteen feet away from me. He was telling stories about how business actually works -- how it was all about relationships. Not textbooks, not spreadsheets…


I worked up the courage to ask him a question. To my surprise, he not only answered it, but invited me to visit him in his office to discuss it further.

That was the one thing that shaped my entire career.

Al wasn’t a big and scary guy like people think CEO’s are. He was so kind to me and I never felt like he was trying to rush things along when we spent time together, even when there were important people right outside his office waiting to see him.

If he was alive today, I know for a fact that he wouldn’t be on his phone when at lunch or try to multitask. He would be giving me his undivided attention.

It’s been twenty years and that’s something I’ve always carried with me when interacting with people.

Over time Al introduced me to high-powered friends of his. I got a job at American Airlines -- a place where you couldn’t even get an interview.

When my friend totaled my brand new Camaro, he called the chairman of Allstate and made sure that the claim was processed immediately. The feeling of sitting in his office while he talked with Richard Haayen on speaker was unexplainable.

Though at the time I didn’t know why he took an interest in me and why he wanted me to read certain books, it started making sense later on in my career.

I never applied to be Al Casey’s apprentice. Our relationship was built off of a few small touches and grew over time, as most lifelong friendships do.

Don’t believe me, think of your best friend and how they came to be that.

I didn’t considered myself to be smarter or more talented than anyone else. But one thing I could do was follow-through on his recommendations. That was 100% in my control.

All it took was knowing a few high-powered CEO’s to earn cred with their friends, which -- surprise, surprise -- were high-powered CEO’s, too.

Being two-thirds younger than everyone, I found myself attending fancy dinners in mansions and private clubs. But, I was their go-to-guy when it came to making a website.


Now, I know making a website isn’t hard at all anymore -- a child could do it. But this was back in the late ‘90’s when you could make a living off of that. And with the introduction of social media, guess what…

Older people will call on the young adults to run their accounts -- namely Facebook campaigns that will drive sales.

Communicating with People

The #1 assumption I had about people like Al Casey was that they’re unapproachable.

I was wrong.

While people who are close to the top are playing the “rat race” -- staying in the kill or be killed mentality -- the people who are at the top are super nice. They’re also super busy and have a ton of people asking them for favors. So they’re not dumb either.

Don’t expect a “yes” when you walk up to a person at the top and ask them to spend five hours a week mentoring you. You need to find a way to be helpful to them. Maybe you can manage their social media accounts for free, transcribe speeches, mow their lawn, or whatever.

My next door neighbor was the CFO of a billion dollar company. One day I was washing my Camaro (pre-my friend wrecking it) and he complimented me on how good a job I was doing.


So off of that, I ask if he wants me to wash his car. And he’s not going to say no.

Two and half hours later, his black Mercedes LS400 was washed and waxed -- the inside vacuumed immaculately.

When he came out, he was so impressed that he gave me $40, a lot for a college freshman.

But even better than that., he invited me to his office, introduced me to other executives at the company, and offered me a job. I turned down the job, but you best believe I followed up on the connections I made.

A “secret” of mine was to go to Hallmark and get thank you cards.

Today, that may seem old-fashioned, now that we have SMS texting and Facebook and Twitter. But I’ve actually found that sending someone actual, physical mail is more important than a text. Nearly all communication is digital nowadays, so a real card or gift stands out.

The #1 reason young adults aren’t getting mentors in this day and age is that, they don’t reach out. Afraid of getting rejected or feeling unworthy of that important person’s time.

So fix that, and go for it! Just be sure to do your homework in advance. You’ll realize just how much you’ve been missing when you can have an expert in your corner.


Studying in a Mentorship

Before I had a lot of experience working with mentors, I read several-thousand books -- mainly autobiographies (not biographies, those aren’t from the source).

When I read those books, instead of getting through it as-fast-as-possible, I’d pretend that the author was there with me. I’d pretend that they were explaining their life lessons to me, and I’d pay close attention, with the same respect as if they were actually there. No distractions, just me and them.

I would consider WHY they made the decisions they made and stop to ponder why. I’d sometimes ask aloud.

Yes, to a book.

But you can still imagine what they might say. And that’s where the real learning occurs.

Reading this way is how I practiced being a good mentee before ever having a mentor. When I finally had the honor of meeting the CEO of Southwest Airlines, George H.W. Bush, Colin Powell, and other such people, it felt like I already knew them.

This is a huge advantage to have when meeting someone powerful. You don’t want to ask them a question they’ve been asked a million times, do you?

I enjoyed reading autobiographies by people like, Sam Walton (Made in America), Ray Kroc (Grinding it Out), and Bill Gates (The Road Ahead).

I also read books such as, Snow Crash, Founders at Work, Discovering Your Personality Type, The Laundrymen, and Rogue Trader, which have inspired me and helped me learn.

Blogs like, Ben Thompson’s Stratechery and The Exponential View by Azeem Azhar are also great sources to learn from.

Changing Your Beliefs

I’ve made mentoring akin to having Lebron James on your team. While it’s a huge advantage and your likelihood of winning has gone up exponentially, he demands excellence.

Be ready to up your game.


Change your bad habits that you’ve been clinging to for a long time and be honest with yourself in ways that can be quite painful.

I’ve definitely made some bone-headed mistakes and have tried to cover them up by making excuses that sounded good… in my head.

My mentors have definitely been frustrated by my behavior and even to this day, they catch me rationalizing things so I can see it my way instead of how it is. This need to be right cost me relationships and money.

Only now have I started to see why my mentors gave me certain advice, which I didn’t listen to when I was younger -- I find myself giving that same advice to the bright, young people I mentor.

“Knowitallism” is something I wish I didn’t have when people were trying to help me, I wish I had more humility.

I hope that you can spot and stop this behavior, instead of frustrating your mentor and risk losing them.

How I Received Al’s 14 “Dos and Don’ts”

Al didn’t have a computer, believe it or not. He didn’t do email, instead he had all of his communications printed out and dictated all of his messages between his three secretaries.

Over twenty years ago Al gave me the piece of paper with dos and don’ts. I’ve been extremely careful to preserve it. Through the years of changing dormitories, apartments, and houses, I’ve made sure not to lose it.

Sure I could take a picture with my phone and not have to worry about it but, I’m superstitious about having the actual, physical paper.

While all of the dos and don’ts are supposed to be equally important, he always stressed the importance of listening.

Ironically, the people who are terrible listeners don’t get it, and the people who insist that they’re amazing listeners are usually the worst.

Technology has made listening worse, in my opinion. The young people believe that they can be on their phones and still pay attention to the conversation that’s happening around them.

They’re sure of it, but a plethora of research shows that it’s just not true.

Mistakes People Make

The more important someone is, the more valuable their time is.

People -- believe it or not -- will ask for money and favors right off the bat. Do not make that mistake. While these potential mentors don’t want to be rude when you ask for such things, they’ll politely decline you.

Stay Updated in Your Job

Al Casey’s 14 tips are timeless. He advises us to be a constantly curious observer of the passing scene.


I translate that into being super selective of what books, blogs, music, and other media you consume. I also take it as to surround yourself with people who can challenge you -- which may require hard choices about dropping friends who “waste” your time.

The second you see your job as a mere way to pay your bills or as an activity you “have to” do until 5:00 every day is a sign that you’re not growing or learning anymore.

What’s Wrong with College?

Colleges are great -- there’s nothing “wrong” with them, as they’re doing what they’re supposed to do.

Though if you have the expectation that you’ll be able to use your diploma as a redemption code for a job at the window, well… you’re going to get slapped by reality.

It’s all about what you put in.

It’s fashionable nowadays for young adults to say, “College is a scam, overpriced, irrelevant, and an overall waste of time.” But in reality, it’s where you can connect with amazing people. You of course have to take advantage of those opportunities when they come your way.

If you already have an amazing network of people and are ready to become an entrepreneur, then go right ahead.

There’s a lot of twenty-something year old CEO’s (whose company is them and only them) that had learn this lesson the hard way.

Start Now

Take everything you’ve just read in and add this on top of it.

Start building your personal brand now, before it’s time to look for a job.

If you don’t, you’ll be too late and you’ll wish you had started building your knowledge, network, and experience sooner.

If you want to become a digital marketing pro through our training program (free to young adults who qualify) and want (real) work experience, go check out