AI as Executive Coach

 

Prompt: "create a graphic that will represent a real human founder/CEO 

interacting with an AI executive coach"

Of course it was going to happen...

Sam Parr has had some serious success in the startup world, and in recognition that an executive coach would help him along the eay, he built his own executive coach using AI. Check it out, here.

That sounded interesting to me, seeing as I've been advising startup founder/CEOs for the last 25 years, and using AI for the last several years. What could go wrong, right? 

The first stop on the journey is, as you might have guessed, is to ask AI. Duh.

Here's how I started: https://chatgpt.com/share/681b8309-7908-8005-9beb-357b7e1eba27

I'm not suggesting that using AI as your personal executive coach is going to work well in every case, and I'm sure there will continue to be hallucinations, but it may give you some interesting and possibly even useful insights. It will almost certainly help you prepare for meeting with a real human executive coach.

Try it out; let me know how it goes!

Pin Boy: A tale of value added service

Remembering my days in the pit...

It was the mid-1950s. I was just a kid, working as a pin boy — the human reset button for a game that never stopped. My job was simple: scramble into the pit, reset the pins, return the ball, and get the hell out of the way before the next bowler launched a twelve-pound rocket down the lane. There was no warning, no buzzer, no mercy. Just speed, timing, and a little bit of luck.

The pay? Low. The hours? Long. The danger? Constant. Flying pins had a mind of their own, and I had the bruises to prove it. The pit itself? Hot, grimy, and loud — no air conditioning, no breeze, just stale air and the smell of machine oil and worn-out shoes. It felt more like a boiler room than a part-time job.

Resetting pins wasn’t just about speed — it took strength. Each one stood 15 inches tall, almost 5 inches wide, and weighed in at over 3½ pounds. Gathering three in each hand with still-growing fingers was a challenge, especially when your grip slipped on the glossy lacquered wood. You’d hustle to scoop up six, crouch into place, and balance them just right before diving back to safety. It was part ballet, part battlefield.

Most nights, I kept my head down and my legs up — literally — sitting on the back of the pit with my knees tucked and head turned away, minimizing my target profile. It was part survival instinct, part street smarts.

Sometimes, under just the right conditions, I could nudge a bowler’s score a little higher — a discreet kick of a lingering pin at just the right moment. Not exactly legal. Not exactly wrong. Let’s call it… value-added service.

Turns out, value-added service came in more forms than one.

When the last frame was done and the pins stopped flying, I’d climb out of the pit, brush myself off, and hustle up front to catch the bowler before they left. A well-timed, “Nice game!” or “You were on fire tonight!” often turned a lukewarm tip into a generous one. It wasn’t flattery — it was recognition. People like to feel seen. And I learned, even back then, that timing, effort, and a little charm could turn hard work into real reward.

And just to keep things interesting, I sometimes reset two adjacent alleys at the same time. Twice the pins. Twice the pressure. Twice the chances of getting smacked by a rogue bowling ball. But if you could pull it off — if you could keep pace and stay safe — you doubled your earning potential. It was risky, sure. But it also made the job fun. And more importantly, it gave me my first taste of scaling under pressure — the art of doing more, faster, with the same tools and the same 10 fingers.

Those nights in the pit were loud, gritty, and unpredictable. But looking back, they were a masterclass in customer service, hustle, and entrepreneurial instinct — long before I had those words to describe it.

I didn’t know it then, but I was already learning how to run a business: show up early, work hard, stay alert, treat people well, and never be afraid to find a creative edge — even if it meant kicking a pin once in a while.

Al

Clarity of Vision +

 “The trick to being a great founder… is your ability to be presented with a problem unlike anything you’ve seen before and solve it very quickly.

When Sam Altman was CEO of Y Combinator, they were looking at 20,000+ companies per year and tracked the founder qualities that correlated with certain startup outcomes. In no particular order, Sam believes the following qualities matter most:

1. Clarity of vision. “Can the founder explain what they do and why? If the founder can’t explain it clearly to us, then (a) they’re not going to be able to recruit, hire, sell, talk to the press; and (b) it means they’re not the kind of person who is a really clear thinker in general and that’s so important to a business.”

2. Determination & Passion. “There are founders who don’t take no for an answer and bend the world to their will and those are the ones we want to fund. Then there are founders that every time they run across a small impediment just turn around. Unfortunately you run into so many impediments every day that if you’re the kind of person who just turns around, that’s really a problem. You also have to really believe that what you’re doing is important. The best companies are always mission-oriented.”

3. Raw intelligence.

4. The ability to get things done quickly. “It’s not entirely accurate to say that speed and quality of decision-making correlate exactly with startup success but it’s not a bad first approximation. Being quick, decisive, and getting things done quickly—if you look at our data, that would just correlate almost exactly with all of our successful founders. And other founders that look on paper like they should be really successful but fail are often missing this one trait.”

https://www.instagram.com/reel/DFqJAkzoY4O/?utm_source=ig_web_copy_link

On the Non-physicality of Software

This is a relic from the times when software had a physical form, you could hold it in your hand.

In this new age, software comes streaming into your device, nobody touches anything, it has no physical form whatsoever.

The photo is a recent ad on eBay, for the Mac version of a product I wrote in 1985 which (humblebrag) just happened to turn out to be the first of a new class of software, called CRM, Customer Resource Management for people with a PC. Boring, I know, but at the time it was interesting to me.

There was one event that brought into sharp focus this concept that software has no physical form...

I was selling my product, the software I called TeleMagic, to a man in London. He was buying the right to sell my software in the UK. It was a very informal event. We sat at a table at a local café and crafted a handwritten agreement without lawyers involved. We signed, he gave me a check.

And then, for the true magic moment, I opened my briefcase and removed a stack of 10 "floppy diskettes" that contained the source code to the product, and copied them one by one onto the customer's hard drive.

Then I took the diskettes back. The customer had nothing physical at all. I went on to sell a few other countries on that trip, and it was just so delightful to get big checks for something that had no physical form.

Software is pure thought made real, just not real in the sense that you can sense its physicality.

The idea I had for the product was transferred from my brain through my fingertips onto the keyboard and into the computer. I used a specialized language called dBase II to get the computer to understand what I wanted it to do.

That first session of programming TeleMagic into existence was followed by thousands of others, addictively debugging, improving, inventing, throwing away long hours of work after rethinking, and overthinking, all these insane purely mental hours to create something that doesn't exist in any physical form.

Software is an entity that can take thousands of hours to create but can be eliminated in an instant with a simple Delete keystroke.

A product without a physical form has enormous advantages over all other products. It doesn't wear out or break down, it doesn't cost anything for transportation or storage, and it can be reproduced infinitely for almost zero incremental cost. It's this last one that is why software companies are so profitable.

In the pre-internet years, software needed a physical form so you could buy it and put it into your PC to make it do what you wanted. That's what the diskette was for: backup, storage, transportation.

That's all gone now. The software business is now even more profitable without all the mess of a physical product.

I keep having thoughts about getting back into the software business. It was fun...

Shortcut to Success in Life and Business

 

One of the only true shortcuts in life is finding an expert and apprenticing under them.  

James Clear

Learn from Your Mistakes or Other People's Mistakes?

 

It's good to learn from your mistakes. 

It's better to learn from other people's mistakes.

Warren Buffett

Your mistakes aren’t the best teacher—just the most expensive.

You can start at the bottom of the mountain and make every mistake from scratch on the way to the top, or you can take a sherpa with you and master the best of what other people have already figured out.

The successful learn vicariously; the foolish insist on first hand pain.

Farnam Street

Don’t try to figure everything out on your own. Hire advisors who’ve been there before and can offer insights you wouldn’t get otherwise. Test advisors before committing—do a workshop to see how they add value before making a long-term hire. And always be evaluating if they’re still contributing.

Lenny's Newsletter

It's a (human) process

A couple of days ago I had just finished coding a feature in EZchecklist that I'd wanted to do for a long time. It took about 5 hours to get working, and it looked good, but the underlying coding was so ugly that I couldn't bear it if anyone ever saw it. The odds of someone seeing the ugliness were extremely remote, but before I went to sleep I promised myself to rewrite the code so that it was more presentable (to myself, at least).

That opportunity came the next morning because I just couldn't live another day with all that ugly code living inside my computer, even though it was invisible to the world except me, of course.  Another five hours and it was done.  Two hundred plus lines of code replaced with 39 lines.

Feeling much better about the transformation, I then had the thought that chatGPT 4.o might be able to do better, so I copied and pasted the code into the AI and asked it to optimize it... if it can. AI got it down to about 18 lines and did it in about 5 seconds, tops, but it's not as easy to follow as my code.  Sure, it would run a bit faster but speed is not the issue here.

Having a coder to coder chat with AI about the various approaches to the problem was amazingly educational.  For me.  I doubt AI learned anything, and sure didn't have that warm fuzzy feeling of getting something to work.

Maybe I'll go back later and implement AI's optimized coding.  Maybe not.  There's something to be said for pride of human workmanship rather than the sterile perfection of AI.

And I'm happy that, at 82, my mind is still capable of learning new approaches to coding.

Note: I asked AI to illustrate the concept. It took about 10 seconds. I couldn't have done it in 10 years.