Writing With AI Isn't Like Using a Calculator [Friday Wrap-Up]

Hey everybody, and welcome to the Friday wrap up on Streamline Solopreneur, a short

episode where I cover four things, what's on my mind this week? Recommended reading

something fun and something to help your systems. This is the show that helps solo

business owners go from doing everything themselves to saving 25 hours per month

without over-reliance on AI or hiring a team.

Hopefully this week's curation gets you thinking about your own systems. Before you

close the laptop for the weekend,

I'm your host, Joe Casabona, and here's what's on my mind for August 28th, 2026.

Okay, number one, writing with AI is not the same as using a calculator for math

financier. Stanley Druckenmiller is in hot water this week for using AI to write

his criticism of Scott Bessant

and he said when facing this criticism that he's not embarrassed because using AI

to write is akin to using a calculator. When I do math problems,

I've seen this more than once over the past couple of weeks and I've even referred

to large language models as word calculators. But maybe I should stop because when

you say writing with AI is like using a calculator for math shows a deep misunderstanding

of math calculators and words,

there are stark differences. For example,

you still need to know the calculation you are trying to solve.

You can't just shout solve for X into a calculator without more information.

And maybe you're thinking, okay, well I know I want to criticize Scott Scent. Maybe

I even know I want to criticize him for inflation or tariffs or whatever, right?

Write me an article that does that.

But here's the other side of that argument.

Each math problem

yields one result. One answer.

As my computer science teacher back in college, Dr. McCloskey often said The beauty

of math is that it is not ambiguous.

You have a math problem, an equation, and it will yield one answer and the same answer

over and over again.

If you ask a large language model to criticize Scott Besson,

you'll get vastly different answers between large language models, prompts, or even

attempts.

Claude will not output the same article twice.

If you give it a prompt of, I need an article that criticizes Scott Bessant on inflation,

you will get different articles every time

you can use any calculator in the entire world. Any working calculator, I guess I'll

say to solve five times five,

you will get 25 every single time. If you're using a more advanced a scientific calculator

and you say, solve for 10

equals X over two, you'll get 20 every single time.

But that's not even

my biggest gripe with this analogy.

my biggest gripe with this analogy

is that it is extremely troubling

when people use calculators for basic math.

I recently paid for takeout with cash at a restaurant.

The total was $47 and 46 cents, and I handed the cashier $48.

She had no intention of giving me my change. And I looked at her

And she said, do you want the change? It's just a few cents.

I said, it's like 50 cents.

And she brought me two quarters

and I'm confident that she brought me two quarters because she didn't actually know

that the true change was 54 cents. And I just said like

50 cents.

She did not know the amount of change I was supposed to get.

This is something I see constantly. I was at an airport one time and

the guy who was ordering in front of me,

his total came to $10 and 19 cents. He hands the cashier a 20 and then says, oh,

I just found a quarter.

So the cashier says, how much change are you supposed to get back? And the patron

said, I don't know.

I was like, guys, it's 6 cents. 6 cents, 25 minus 19. It

is extremely troubling. That's bad.

Everybody should be able to do basic math

in their head,

but

not being able to articulate

your own thoughts

without

assistance from ai,

that

is so

much

worse,

especially

if like

Stanley Druckenmiller,

you are a billionaire financier,

but you don't need to be a billionaire

to be able to state

your thoughts.

I'm not saying you need to do it cleanly or clearly the first time,

but you should be able to articulate your own opinions without asking ai.

Do you have something on your mind? Let me know.

What do you think about my screed? Just now?

You can head over to streamlined feedback.com, write in or leave a voice note.

If you leave a voice note, I might even play it on the show.

Alright, let's get to recommended reading this week. The recommended reading is the

Unraveling of Podcaster Ashley Flowers True Crime Empire. This is from journalist

Ashley Carmen for Bloomberg.

And I am, I'm really not much of a True Crime podcast listener anymore.

I enjoyed the first couple of seasons of Serial.

I used to listen to Criminal by Phoebe Judge

and Dr. Death plus some limited run shows. Those were interesting to me, but

it's been a while. I realized that listening to too much true crime actually had

like an adverse effect on the way

I was thinking about stuff.

And to my knowledge, I haven't listened to any of

audio Chuck's shows Audio. Chuck is the company that Ashley Flowers

owns

The most interesting bit of this story for me is not necessarily

about Crime junkies or audio Chuck. It actually came towards the beginning of the

story for me and I'm gonna read this verbatim from the article.

A growing number of top performers from Call her Daddy's Alex Cooper to Jimmy Donaldson,

AKA Mr. Beast are attempting to parlay their internet clout into broader, more diversified

companies.

But such transitions can be difficult

to pull it off, the already harried hosts typically have to take on expansive new

leadership duties while continuing to star on podcasts or YouTube channels with intensely

demanding schedules. Often it amounts to a frantic juggling act for even the most

industrious hustlers

end quote.

I see a lot of parallels between the personalities described here and solopreneurs.

When you try to build an empire based on you, you're going to hit up against some

limitation time,

most likely money.

The resources that you have at your disposal

appeal,

something like that. You try to grow beyond yourself. You cannot do it by yourself.

I knew when I made the decision to stay a company of one

that I wasn't going to build an empire or generate massive generational wealth.

But I did know that I could make more than enough money to support my family

and spend time with my kids.

I think the framing of this story is also interesting to me as a dad who has made

very different decisions from a lot of business owners.

Ashley Flowers admitted that she killed a popular show to spend more time with her

young daughter, but later in the article it quotes her as saying this

quote,

No one at this company works more hours than I do. Yes, I am the founder, but that

is not why.

It's because I care so much about this company and the work we do.

I regularly set my alarm at two or 3:00 AM and work over the weekend holidays and

when I'm sick,

that statement

feels diametrically opposed

to the idea that you are ending something to spend more time with your daughter.

Unless you're saying, I set my alarm at two or 3:00 AM so I can work from three to

seven before she wakes up. But I don't think that's the implication here.

'cause she's also saying she works weekends, holidays

when she's sick.

I think two things can be true.

You can care about the company you've built while also not doing everything yourself.

The story routinely states how things that she tried delegating out, she took back

over

and micromanaged.

And this is a parable for us as solo operators as well.

How many times have you said No one can do what I can do?

Increasingly automated systems can take a lot off of our plate.

And if our goal really is time freedom,

preventing burnout, spending more time with our daughters,

well, we should let those automated systems take things off of our plate.

I'm not saying you need to hire,

I don't want to hire any full-time employees. I have a VA

and a couple of other contractors to do things that I literally don't know, like

can't do. Well I

don't have any employees and I never intend on having employees,

but that doesn't mean you can't take things off of your plate.

You can and you should.

So I think that article's really interesting.

Alright, let's move over to something fun.

The something fun this week is

one of my favorite YouTube channels, epic Rap Battles of history

or ERB

has a new video out Tom Cruise versus Evil Knievel.

I love epic rap battles of history. I think they are clever, well researched and

catchy. My wife, when she was pregnant with our oldest, was worried that our daughter

would be born knowing some of these epic rap battles of history because I listened

to them so much.

But I also appreciate that the guys took a step back from doing videos every two

weeks to prevent burnout from them and their team. It's kind of like the opposite

of what you see

in the Crime Junkie story.

They were doing too much

in too little of amount of time and they took a step back. And even though they went

from publishing fortnightly

to every few months, now I greatly look forward to new ones.

This one, Tom Cruise versus Evil Knievel is just as funny as and and Clever as their

previous work.

Plus the guy they hired to play Tom Cruise is, is

incredible. At first I thought it was one of the guys. Nice Peter. Then I realized

it wasn't. Then I

thought, is that,

is that actually Tom Cruise? But obviously it, it was not.

Uh, so the guy that they hired to play Tom Cruise is incredible. I think he's, I

think his handle on Instagram is at not Tom Cruise. So

check him out. Really good love, love their body of work.

this is a really good one

and uh,

I strongly recommend the channel in general.

Okay, moving on to something to help your systems.

I wanna talk about the stream deck today. And yes, I mean I talk about,

the stream deck a lot.

usually when I'm

talking about my systems, right? But over the past few weeks I showed off my mad

stream deck skills.

Sorry, I'm not 20 anymore,

on calls and recordings and folks were really impressed by it. The ability for me

to seamlessly switch or add things or move

between cameras.

And while I've written about my stream decks several times,

it's always worth resurfacing. So in, in the description, in the show notes for this,

uh, you'll find a link to how I've configured my stream deck.

But if you're looking for a place to start, I'll put this video in the cards on YouTube.

I've made a video about what your first six stream deck buttons should be.

And I think that that is a

really good starting point if you are unsure if you want to use the stream deck.

'cause I, I gotta tell you like, uh,

keyboard shortcuts are great, but having a button with a label or a an icon is much,

much easier in my opinion. And

it's how I run this whole show. So

if you're looking for a great piece of hardware,

maybe there's gonna be a Labor Day sale.

Uh, as this episode comes out,

it is a week from Labor Day here in the United States.

Uh, the stream deck is, is a great purchase in my opinion.

But that's it for this episode of the Friday wrap up from Streamline Solopreneur.

These episodes are about taking more time off, especially on the weekends. And the

best way to do that is by having good systems in place, good solo ops.

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Thanks so much for listening, and until next time, I hope you find some space in

your week.