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Month: December 2020

Crippled CEO Blog #063: Corporatespeak

Crippled CEO Blog #063:

Michael McGahee and I have been compiling a list all year of cringe-inducing “corporatespeak” — buzz words typically sprinkled into Zoom meetings and emails by young professionals of huge companies (often companies who view themselves as hip and modern). I believe they do this as a form of signaling, letting you know how up to date they are with the current corporate lingo. 

It’s nauseating. 

You know some of the classic ones: let’s circle back, paradigm shift, synergy, and so on. 

But over the last year, we have compiled many, many more. 

My goal is to write a (fictional) memo using all 39 of them — the cringiest corporatespeak email of all time. 

Because this is how we are ending 2020.

The full list will new below the letter. Feel free to use it to see how many of these terrible phases are in your vocabulary. And if you have any more, PLEASE let me know in the comments. 

Let’s do this.  

Dear team (and remember, we are a team, not staff, because staff is an infection):

I just wanted to touch base about the great meeting today discussing the email about the phone call that originated from last week’s video conference. We managed to really set our intentions and think outside the box

However, I think we need to button some things up. It’s critical that we bird dog the project thoroughly to truly ensure that we are all aligned on this

If we can get our ducks in a row and focus exclusively on our North Star,  there’s no reason why we can’t move the needle in a serious way. 

Let’s unpack that for a minute. 

Does it scale?

That’s the question we most really drill down into and figure out. If I can piggyback on what Karen said earlier in the text message about the voicemail about the talk at the team building exercise, we MUST do a deep dive to make sure all of this is brand-aligned for us and our clients. 

Just to clarify, we are going to have to take a hair cut on this. The margins are very thin, so we really need you to sharpen your pencils on the pricing. Let’s put a pin in that for now. 

If we are going to be successful, we must pivot. 

What is the one thing I can do to make your day better?

That’s one question I use to shift the paradigm and to level up my thinking. 

But I can’t do this alone. If we are going to make this work, we need each and every one of you to be a cheerleader for this initiative. Please, wrap your arms around this for me and help me understand what’s needed. 

Let’s loop back in order to loop me in so that we  can close the loop on this. Because if we all work together, we can create an amazing synergy. We just need some boots on the ground. 

Let’s take this conversation offlineWhy don’t we table this and revisit it later? And then can circle back at the beginning of next week and jump on a call to flesh this out. Just remember that I have a hard stop at 5 pm to meet with the annual trust fall event planning committee. I’ll follow that call up with an email, of course, so be on the lookout for that. 

Thank you so much, everyone. I think we are all in alignment on this. 

We’ll speak soon, and don’t forget: stay POSITIVE and test NEGATIVE!


Karen Karenson

Senior Executive Vice President Director of Employee Compliance, Development, and Accountability 

Here is the full list:

Circle back

Drill down

Take a haircut

Sharpen your pencil

Think outside the box


Shift the paradigm


Touch base

We’re aligned on this / alignment

Does it scale?

Close the loop

Move the needle

Loop me in


Set your intentions

Why don’t we table that and revisit it later

What’s the one thing I can do to make your day better?

Just to clarify

Flesh it out


Let’s make sure this is brand-aligned

I have a hard stop

Put a pin in this

Let’s jump on a call

Button some things up

Loop back

Ducks in a row

Let’s unpack that for a minute

North star

Let’s take this conversation offline

Stay positive and test negative

Wrap your arms around that for me

Boots on the ground

Deep dive

Let me piggyback

Level up

(Happy New Year, y’all. Thanks for doing 2020 with me. If my posts brought you inspiration or info or a laugh this year, maybe subscribe by sending a text with the word CRIP to 484848. I’ll send one message per week with a link to the latest blog post. Complete satisfaction or your money back. Also, it’s free.)

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Crippled CEO Blog #062: Lessons from Chess

Crippled CEO Blog #062:

If you’ve been reading these for a while, then first, thank you, that’s very cool of you, but also, you know that I’ve been making a fairly serious attempt to get as good as I can at chess. I started taking lessons three times a week from International Master (and all around great guy) Vitaly Neimer in July, and I spend a good chunk of my free time playing chess, watching videos about chess, and reading about chess. (And yes, I’ve seen the show. It’s great.)

There are three insights chess has put a spotlight on for me, which apply to real life, that I wanted to share with you — and I don’t mean the typical “thinking three steps ahead” trope you might expect. 

  1. Chess Blindness 

When you first start playing chess, it is very common to just give away an important piece, like a queen, for no reason. You are looking at everything so intensely, but somehow you just missed this very obvious thing right in front of you. While this does get better as you practice, it doesn’t seem to ever go away completely, and there are tons of examples of even world class level grandmasters somehow going “blind” for a moment and donating a piece or making an obvious mistake. 

As you experience this over and over again (and I definitely have), you realize how much more susceptible you are to missing something important right in front of you because you’re focused elsewhere, on something far less important, than you think you are. You THINK you will notice this huge, critically important issue, but if you’re distracted elsewhere, there’s a good chance you might not. In chess, we are taught to take a moment each turn and look for checks, captures, and threats, a sort of mental safety check list, to try to help mitigate this. In real life, you can do something similar, but just being aware how likely you are to miss something both major and obvious will help you to be more careful. 

  1. Time pressure 

All “real” chess is played with some kind of time control. Each player is given a set amount of time to play all of their moves. This can be two hours or two minutes or anything in between. Either way, when it’s your move, your clock is ticking down. 

“Time pressure” is the DRAMATIC impact on your play that occurs when you are low on time. Even the best players in the world become mere shadows of themselves when the clock is getting close to zero. 

We all know that we are prone to mistakes when we are rushed, or that we don’t think as clearly, but it’s hard to appreciate the full extent of how compromised you are until you see it play out on that 64 square board. In chess, you can go back and look at your game again, so the idiotic mistakes that you made because of the time pressure are clear as day, right in front of you. You typically can’t do that in real life, so it’s hard to speculate on what you would have done differently, but chess makes it brutally apparent. Being pressured by a lack of time makes you dumb. You do things that you would never in a million years do otherwise. Tim Ferriss refuses to jump on any opportunity or investment, no matter how good it seems, if there is a short deadline, or if he feels pressured by time. And it makes sense. 

Outside of chess, deadlines and time pressures are almost always artificial. You can almost always get more time if you need it. The sneaky thing about time pressure is that, in the moment, you know that you are rushed, but you still think you’re making the right decision. It is only after the fact, when you have more time to think, that you realize your mistake. The solution to this is, whenever possible, like Tim, don’t make decisions when you’re short on time. Prioritize giving yourself more time to think. Ask yourself, “What is the absolute worst thing that will happen if I don’t make this decision right now?” Usually, it’s not that bad. Give yourself the time, even when you think you don’t need it. You do.

  1. Tilt

I first learned the concept of “tilt” playing poker. It has the exact same meaning in chess. The name comes from pinball machines, which would display the word “tilt” as an error message when the table was lifted or moved violently, as often happens when someone is upset. In chess and poker, someone is “tilted” or “on tilt” when something goes wrong, they get upset, and then start making bad decisions and playing poorly. 

My first ever blog post, #001, was actually about this. Scientific studies have shown that we lose a substantial number of IQ points when we are in a bad mood, and the more upset we are, the worse it gets. You can read that whole post right here:

The basic idea of the post, and the lesson we can learn from chess, is that you’re incapable of making the best decisions when you’re upset by something terrible that has happened to you. You are tempted to try and fix the problem right away, but doing so only makes it worse. The solution is to wait. Don’t do anything until your state of mind improves. Waiting on purpose isn’t laziness, it’s a choice, and an action. And it is often the best one.

There are a ton of other lessons we can extract from chess and apply to our lives. The idea of prophylaxis (seeing a problem coming, and protecting against it ahead of time), how improvements come slowly, in inches — not miles, and so on. But I thought these three were the ones you don’t hear about the most, and were the most interesting to me. Now you can benefit from them without spending a couple hours a day getting beat up by better chess players.

PS: I’m giving a few of my friends chess lessons with IM Vitaly as Christmas gifts. I think it’s a pretty rad gift. If you would like to, as well, let me know, and I will put you in touch with him, or just go to his website 

(I bet you can imagine someone who would like this. You should send it to them. You should also subscribe to my weekly text message so you get notified as soon as I post the latest blog. All you have to do is send a text to the phone number 484848 with the word CRIP and the magic will happen.)

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Crippled CEO Blog #061: You Pick Your Customers

Crippled CEO Blog #061:

Why aren’t you only selling to the customers who want to pay you more?

Seth Godin has been a hero of mine for two decades. I recently heard him articulate something that I had always known intuitively, but he explained perfectly, as he always does.

Some customers like to pay less for things. That is how they identify themselves. They are bargain hunters, looking for the cheapest price. My friend Jen was like this. She once made us drive to another liquor store to save roughly 1 dollar on a bottle of rum. Jen would also always pick the generic brand over the “real” one. Jen was (and maybe still is) all about paying as little as possible. 

Some customers like to pay more. It’s true. I know, because I am one of them. When I redid my kitchen, I gravitated toward the better, more expensive appliances, because I wanted to be certain I wouldn’t have to worry about them. When the new iPhones came out, I got the better, more expensive one with the most space, because I didn’t want to have to worry about ever running out. And I’m currently upset that I can’t find better, more expensive lawn care. I used to be upset that I couldn’t find a better, more expensive doctor, but I now have a private concierge doc (you should, too), and I’m much happier. Part of this is because I can currently afford better stuff, but even when I couldn’t, I was always willing to trade dollars for time or convenience or quality or reassurance as much as I could, whenever possible. I was pretty broke when I moved out of my parents’ house and into my first home at the age of 18, but even still, instead of getting a cheaper bedroom set from IKEA or Rooms To Go, I found this amazing dark wood set from a local store. It was more, but I knew it’d last forever and I’d save in the long run. Two decades later, it’s still in my bedroom and looks great. Long story longer, just like Jen HAS to find a deal, this is programmed into my identity (and I might even make a case that it is one reason why I’ve been able to find some modicum of business success, but that’s a different article). 

So, some customers want to pay less. Some customers want to pay more. It takes the same effort to the sell to both groups, each has their own set of challenges, so why do so many businesses pick the customers who want to pay less? The answer: because it’s easy to hide there, to use it as an excuse for remaining average. Picking customers who prefer to pay more means you have to be worthy of the extra expense.

But if you’re charging more, you can afford to be better. And there is nothing wrong with being the more expensive option. If someone walks into a Rolex dealer and says they want to buy a $100 watch, they will politely suggest going to look at the Citizens a couple doors down because Rolex doesn’t sell $100 watches. Rolex made the choice to sell to customers who want to pay more, and then built their business (and watches) accordingly. 

I have a massage therapist friend who charges $200 for a 60 minute massage. I believe you can get a massage at a place like Massage Envy for around $50. And depending who you get, it might be just as good. But also… maybe not. And because of what she charges, my friend only has wealthier clientele. When they take their yacht to the Bahamas, they invite her to come along to be their on board massage therapist. She made a conscious decision to be the more expensive therapist, and the result is she gets clients who want to pay more.

Sometimes, though, a customer comes along who you want to serve, but who you can’t charge the proper price, and you don’t want to lower your price, thus signaling that you are a business for people who want to negotiate on price. 

Funny enough, Seth suggests something we’ve been doing for years. 

You give it away for free. 

Life Saver Pool Fence is the most expensive pool fence. It’s also the best pool fence. It’s worth more than what we charge, but it costs more than all the others. 

The first time a family called me whose child had just had a non-fatal drowning and wanted to buy a pool fence, I knew I couldn’t charge them the full price, but I didn’t want to turn them away, either. I gave it to them for free, and thus the Save a Life Program was born. 

If you want a Life Saver Pool Fence, you either pay a premium price, or if your family has experienced a fatal or non-fatal drowning, or if you were given free ISR lessons through Live Like Jake, we give it to you for free, but there’s no in between. If you’re the kind of customer who wants to pay less, we politely suggest Pool Corral, our competitor grade, or if you’re handy, Pool Fence DIY, which you can install yourself. 

Spodak Dental is a higher end dental campus in Delray Beach. They have all of the most up to date equipment, every service you could want, all in this super cool high tech building. Their prices are set. They don’t give discounts. But a few times a year they have a day where they give away free dental care to underprivileged children. Full price or free. 

If you’re doing it right, not everyone is your customer. This is good, because it means that you get to pick. You get to choose the kind of customer you get. If you choose the customers who prefer to pay more, then you can afford to be worth the expense. This seems like a win-win for everybody to me.

(Was this worth what you paid for it? You should share it with your friends. And if you want to make sure that you never miss a post, send a text message to 484848 with the word CRIP. That will allow me to send you one message per week with the link to the latest blog as soon as it’s up. It’s a pretty swell deal.)

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Crippled CEO Blog #060: Opinions are Like…

Crippled CEO Blog #060:

Two weeks ago, I wrote a blog, #58, detailing why I 💙❤️ Superman. 

I didn’t like it. 

I’m usually pretty happy with my posts each week, but I was certain this one was garbage. Meandering, lacking in salient points, not clearly useful. Not good. 

But I posted it anyways, because I write a blog every Sunday, that’s my commitment to myself and y’all, and this was the one I had written. 

That post is one of the best received, most liked blogs I’ve written so far. 

People seem to love it. 

I was surprised. I still am. 

It reminded me of an important lesson that’s easy to lose sight of when we create things, or oversee the creation of things. 

Even when assessing my own work, I’m just one opinion, just one data point. Now, I value my one opinion pretty highly, because I’m awesome and have great taste, but it’s still just one opinion, and there’s a possibility my opinion might be in the minority. I might be wrong. 

This is especially critical to keep in mind when we are making things for commercial consumption — a logo, a website, a brochure, and so on. You might hate it, but you are just one person. Despite your opinion, it just might be wildly successful. 

When Chamber Media pitched me the idea of having an Amish family with 50 kids as the focal point of our Pool Fence DIY video, I thought it was dumb. It seemed silly and juvenile. I just didn’t understand how it would work to sell a pool safety product. And the video was a LOT of money — far more than we had ever spent on any other ad or content, by a factor of ten at least. 

But I reminded myself that I was just one opinion, and I also wasn’t the target market. I left the decision up to the group, and we decided to move forward with it. That video has been seen tens of millions of times and has assisted in millions of dollars in revenue. The vast majority of the comments it receives are nothing short of comparing it to sliced bread. It’s been praised by many as the best Facebook ad of all time. It’s been a huge success. 

Thankfully, I didn’t decide my opinion should have more weight just because I was the one signing the check and making the call. That is an easy thing to think, especially since it means you’re the one taking the risk. But at the end of the day, even if you’re paying for it, or even if you created it, you are still just one opinion, and everyone else might just disagree. 

(I bet you can think of somebody that can use this right now. Why don’t you be a pal and send it to them? Also, take 27 seconds and guarantee you never miss a post by sending a text message with the word CRIP to the number 484848. That will allow me to send you a message each week alerting you of the latest post. You will be happy you did it.)

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