Advice to My Teenage Grandsons

Wizard of Ads Monday Morning Memo

To Hollister and Gideon,

You have arrived at that age when everyone you meet will ask you about your plans for the future. I am older, happier, and probably more successful than those people, so ignore them. Listen to me.

Knowledge is important, but experience is what really matters. School can give you knowledge, but it cannot give you experience.

Experience is the name we give to our mistakes.

Success is simply a matter of surviving your mistakes. But first you have to make them. So take chances. Feel the pain of disappointment. Then pull yourself together.

Avoid the mistakes that are bigger than you.

1. Don’t die.
2. Don’t create a baby until you’re ready.
3. Don’t go to prison.

Those mistakes are hard to undo.

Surviving all your other mistakes will require nothing more than financial and emotional “staying power.”

Financial staying power isn’t measured by how much money you have. In fact, an abundance of cash will tempt you to calculate your burn rate. You will say, “At my current rate of spending, I can last until such-and-such a date before I run out of money.”

When you calculate your burn rate, you create an unconscious plan. You have looked into the future and seen yourself collapsing in defeat on that day. Personally, I have never known anyone who succeeded after calculating their burn rate. They imagined running out of money, and then they did.

I knew they had calculated their burn rate because everywhere they went, they said, “I have to be profitable by such-and-such a date or I will run out of money.”

Boys, no matter how much money you have, you can run out of money. True financial staying power isn’t measured by how much money you have; it’s measured by how little money you need to stay in the game. The secret is to keep your monthly obligations so low that it takes very little to cover your living expenses.

The most successful of my Wizard of Ads partners kept their jobs until they were making enough money as my partner that they could afford to walk away from their previous employment. Some of the others were lucky enough to have a life partner who made enough money to cover all the monthly expenses of the household. The partners who struggled in the early days were the ones who had significant monthly expenses and a lot of money in the bank. These were the ones who calculated their burn rate and then slowly began to panic as they saw that money disappear month after month.

Financial staying power is easy. Live modestly. Don’t owe money.

Emotional staying power is what makes you successful. It gives you the ability to fail without thinking of yourself as a failure. So take chances. Feel the pain of disappointment, then pull yourself together, like I said.

Failure, like success, is a temporary condition.

You are going to need encouragers. I have your MeMaw and the encouragement of God that I find in my Bible.

Mistakes are inevitable. Don’t fear mistakes.

Encourage people. Be slow to offer advice, but quick to offer encouragement. Tell people what you admire about them. No one likes a flatterer, but if you speak the truth, they will hear it as the truth.

Marry your best friend. You will know they are your best friend when you look forward to being with that person, even when you are not imagining them naked. Pennie – your MeMaw – believes in me more than I believe in me. I have asked God to give each of you a life partner like that.

I am not the only person who thinks these things. On May 1, 2024, Jason Fried wrote,

“Occasionally a 17-year-old will write, asking for entrepreneurial or business advice. Oftentimes they’re early bloomers and already have something going on. Others are chomping at the bit once they get out of high school. It’s great to hear from them. But my advice is generally that they don’t need advice. You don’t need advice at 17. You need experiences. You don’t need to be told what to do, you need to be told to do. Now, that in itself could be construed as advice, but it’s really not meant as that. It’s anti-advice, if anything. Don’t listen. You’ll learn out there, not in this email. At 17 you have more time than you’ll ever have to just fuck around and find out. Anything else is just getting in the way. There’s no unlock, no sage advice from some oldster that’s going to make a lick of difference at 17. The doing, and the self-discovery, will give you all the advice you need until you really hit a point where the stakes matter and the right suggestion could mean everything. Until then, wander. Be 17.”

Boys, if I’m not around 10 years from now, be sure to share this letter with Eden and Vance.

Love,

Poobah

PS – Some people will like you for who you are. Some people won’t like you at all. But most people will like you for what you can do for them.

It is never okay for a friend to like you for what you can do for them. In fact, that person is not your friend. But it is definitely okay for your employer to like you for what you can do for them.

When you get a job, know that these are the characteristics of the perfect employee:

1. They do incredibly good work.
2. They always get their work done on time.
3. Everyone likes them.

If any two of those things is true about you, it is enough to make you a valuable employee. If all three of those things are true, every business owner you meet will want to hire you.

PPS – I have known highly effective men and women who radiate professionalism. Their poise, polish, elegance, and charm are intoxicating. These people are often perfectionists by nature, so their professionalism comes to them naturally.

I am not, by nature, a perfectionist. Poise, polish, elegance and charm are not my natural condition. The best I can do is try to be kind and considerate and quick to apologize when I do or say something stupid.

Professionalism, when it is authentic, is amazing. But it can also be a pose, a mask that is worn to disguise the fact that a person is just a posturing little weasel with an expensive haircut, sophisticated manners, and a lot of style. These people can always get a job, but it doesn’t take long to see that they are an empty suit of clothes.

Be professional if it is in your nature, but never forget that effectiveness is what really matters. I have always been a little bit scruffy and undisciplined, but my effectiveness buys me a lot of forgiveness.

Be honest. Encourage others. Listen intently when someone is talking.

Know that I love you.

– Poobah

Bryan Clayton uses a proprietary app to match homeowners who need lawn care with small businesses – many of them solo operators – that provide those services. He has more than 55,000 entrepreneurs serving more than half a million customers. Bryan began mowing lawns in high school and never quit. Today, he runs a $30 million company that brings buyers and sellers together. “There are opportunities aplenty,” Bryan tells roving reporter Rotbart, “to leverage technology in service-sector companies.” Want to make some money? Go now to MondayMorningRadio.com