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Month: October 2021

Crippled CEO Blog #107: Manners matter

Crippled CEO Blog #107:

There’s an aspect of success that I don’t think gets talked about enough.

We hear a lot about intelligence, hard work, creativity, and determination.

You’ve heard me talk a lot about integrity and character. Doing the right thing is always the right thing.

But you know what is tremendously important that you practically never hear about?


Being polite. 

It sounds silly, doesn’t it? Anachronistic. Outdated. 


OK, boomer. 

But seriously. Manners. 

I’ve had vendors who provide quality products and objectively solid customer service whom I actively try to replace with other companies because they’re rude. 

I just don’t like them. They’re not nice.

I left the bank I’d been with for over 20 years for the same reason, and the bank I switched to was the flip side — my contact at BankUnited, Javier, is the most polite, most courteous, nicest to work with banker on the planet. His employer earned millions of dollars in new accounts exclusively because of how nice he is. 

The same goes for customers. I’ve fired otherwise good customers because they are jerks. I’ve kept around poor performers because they are really nice.

Employees, too. If you do great work, but you’re rude to the people around you, I don’t want you. I would much rather have the person who isn’t quite as productive, but makes the environment a lovelier place for everybody around her.

So, yeah. Politeness. Go figure. 

(Do you know who I always let be rude to me? Your mom. She gets a text from me every Sunday, as well, with a link to the latest blog. If you text the number 484848 with the word CRIP as the message, you can, too.)

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Crippled CEO Blog #106: Fail Small

Crippled CEO Blog #106:

“Fail early, fail often.“

This is a frequently repeated mantra in the world of entrepreneurship and management.

You hear it often as a vote in favor of a risky venture or a new idea.

It sounds forward thinking and innovative.

It also gives you something to lean back on when you do, in fact, fail.

It was all part of the plan! Fail early, fail often. Mission accomplished.

I understand the rationale behind this idea. We can’t be afraid of making mistakes. We need to be willing to try new things.

And we learn from failure.

And while failure does teach us what not to do, you can only learn what TO do from success. 

And when it comes to owning a business, failing early and often is fine if you are young, able-bodied, you have no employees, and don’t have a family depending on you.

If it’s just you that you’re hurting, then take those risks. If the result is you end up crashing on couches for a while, that isn’t the end of the world.

But someone like me can’t do that. Being disabled is expensive. If I fail at this business, I end up living in a nursing home. I will end up in a situation that is impossible for me to recover from.

There is a famous legend about Julius Caesar invading the Celts. He and his armies arrived by sea, and it became immediately apparent that they were outnumbered. His troops were scared, and many wanted to turn back.

“Burn the ships!” he ordered. 

His leaders and troops thought he was crazy. If they burned the ships, in the very real possibility that they were defeated, how would they retreat?

They couldn’t.

And that was the point. With their ships on fire, they knew they HAD to win. Their enemies knew they had to win. And with no other choice but victory available, that is exactly what they did.

My ships are also burned. There is no recovery for me if I fail. I run my businesses knowing that I I have no choice but to succeed.

So, with that in mind, how do we take risks? How do we try new things? As we know, the only person who doesn’t make mistakes is the person not accomplishing anything. But with the boats on fire, what do we do? 

Fail small. Instead of failing early and often, I prefer “fail small“.

Take risks with large upsides and minimal downsides.

Try new things in the smallest possible way first, see if there’s success, iterate on that success, grow it a bit, try it again, and so on.

You can survive failing small. You can lose the battle and still win the war. I have projects that started tiny that are now multi-million dollar revenue streams. 

I have other ones that bombed, but we started small, so it’s fine.

And I have a few in the fire right now that will either be amazing or dissolve into nothing, but I haven’t thrown all of my eggs into those baskets, so if they fail, it’s not going to affect my life.

“Fail early, fail often“ is a good example of advice that’s great for some people, but not everybody. We like to think of these quotable heuristics as being ubiquitously beneficial, but the truth is, like most things… it depends. 

(Do you know who never fails me early, nor often? Your mom, that’s who. She also loves getting a text from me each week with a link to the latest blog. If you send a text to the number 484848 with the word CRIP as the message, you, too, can be so lucky.)

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Crippled CEO Blog #105: Interview Your Dream Customer

Crippled CEO Blog #105:

If you own a business or you’re in sales, you probably have a dream customer.

If you are a real estate agent, you probably would love a serial real estate investor.

If you sell shoes, a shoe collector aficionado might be your ideal prospect.

If you’re a yoga instructor, you probably live meeting health-conscious stay at home moms with nannies and disposable income.

I have a secret to getting these clients without having to pitch then the standard way.

Interview them.

Let them tell you about their passion for that thing you do.

 And then publish it on Facebook, Instagram, and YouTube, with the audio on all of the podcast platforms, and post the transcripts as blogs. 

Not only is the entire thing great marketing for you, but you have almost certainly earned that customer for life.

The person you interview is going to share it with all their friends — you just made them look important. And because people like us do things like this, as we know from Seth Godin, customers similar to the people you interview will start seeking you out.

It is a win-win for everybody, and a whole lot more enjoyable than going to a Chamber of Commerce meeting.

(Do you know who always wants to interview me? Your mom, of course. She also gets a text each week for me with a link to the latest blog post. You can, as well. Send a text to the number 484848 with the word CRIP as the message.)

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Crippled CEO Blog #104: My mom and blackjack

Crippled CEO Blog #104:

Two days ago was the 10 year anniversary of my mom passing away.

It definitely doesn’t seem like 10 years.

It also, simultaneously, feels like an entire lifetime.

In a lot of ways, I am not the same person she last had a conversation with. And it’s easy to think that the person I am now is the true, finished version, but I’ve lived long enough to realize that I will be somebody else, with different hobbies, beliefs, and obsessions, 10 years from now (I’ll actually probably be dead, like my mom, in 10 years, but that’s besides the point). 

But there are a lot of things that are still the same as the son she knew, and I’m grateful for those as well.

But that’s not what this post is about today.

My mom loved blackjack. She loves the game, but more importantly, she loved socializing with the people at the table.

And my dad also liked blackjack. I was taught the rules and the nuances of correct play from a very early age, and on cruises, we would often take part in blackjack tournaments where all three of us would end up placing. 

I also love poker, Texas Hold ‘Em specifically.

So, in honor of my amazing mother, I wanted to relay a lesson that she taught me through blackjack and poker.

You cannot base the quality of your decisions on the quality of the outcome.

In chess, if you play all of the very best moves, you will win.

In chess, you have all of the information available on those 64 squares. There is nothing random. There’s no luck. The quality of your decisions directly leads to the quality of the outcome.

But life isn’t like chess.

Life has lots of unknown variables and randomness.

Like poker and blackjack. 

In both those games, you can play perfectly, you can make every correct decision, and still lose. And likewise, you can also do everything wrong and still win.

It is easy to learn the wrong lessons from this. You can justify your terrible play by pointing out the result. You can also decide that what you do doesn’t matter, because in the end, it might not. And you can pick up bad habits based on these individual anecdotes.

But this doesn’t work long-term. If you successfully drove through a red light once, and then got hit by a car driving through a greenlight, you shouldn’t start only driving through red lights. That’s a terrible idea. 

But just like people do this in blackjack and poker, which drove my mom insane, people do it in real life, as well. They look exclusively at the outcome, and decide their success or failure by that. 

In blackjack/poker, you can lose a lot of hands and still win the tournament. Life works the same way. Losing doesn’t have to mean failure. For me, failure comes from making bad decisions. If I lose every now and again, in cards, life, business, and so on, but my decisions were correct — I’m still winning. Eventually. 

Because, once again, doing the right thing really is always the right thing. 

(Do you know who makes me make lots of bad decisions? Your mom. She’s the worst. One correct decision that she makes, though, is subscribing to get this blog each week by sending a text to 484848 with the word CRIP as the message. You should try it, too.)

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Crippled CEO Blog #103: Procrastination and Gray Fun

Crippled CEO Blog #103:

I’ve been procrastinating writing this blog all day because I’ve been in a poopy mood. 

That seems to be a thing more and more often lately. 

But no worries. I’m fine. Everything is fine. 


So, what have I been doing instead? 

Speed chess and YouTube videos. Things I don’t really want to do, that don’t take a long time, because my plan is to start the blog.

But then I did that for hours. 

And while it might have been enjoyable otherwise, it wasn’t, because I knew that I was procrastinating. I forget where I first heard this term, but I’ve always called this phenomenon of not enjoying the thing you’re doing while you’re putting off what you SHOULD be doing “gray fun”. 

It’s feeling bad doing something that should feel good (which also describes my 20’s). 

The good thing about labeling this phenomenon is that you can identify it when it’s occurring and, usually (though clearly not for me today), you can then talk yourself into doing the thing you should be doing so you can then ACTUALLY enjoy this other thing you’re doing now. You just have to flip the order around. 

Before I had a name for it, it was harder to realize exactly what was happening.

And that’s the beauty of naming things. It makes them easier to spot and fix. My favorite allegedly ancient Chinese proverb: “The first step of wisdom is calling things by their correct name.”

Hopefully, this will help you, too. 

And now that the blog is done, maybe I can actually enjoy my next game of chess. 

(You know what I never procrastinate on doing? Reviewing my companies’ financial statements. Ha! Gotcha! But also your mom. Your mom, the lady who sent a text to 484848 with the word CRIP as the message and now receives a text from me every week with a link to the latest blog. What a gal.)

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