Holding Employer Stock

Okay, this is an interesting question.

I know you're going to talk about some nuances.

I actually like the idea, Cale.

I'm not always a big fan of this kind of thing, but I would say, number one, you are in a better position than any to know how your company is doing.

Now, I'm going to say this, and I'm also going to throw a caveat.

Don't drink the Kool-Aid.

What do you put in here that makes it taste so good?

Okay, what do I mean by that? Well, if you, I've had people over the years when I was in the business, they'd been at a company for however long, they always owned the stock, they remember the time it was down 50% and it came back to new highs and they went through it again and it always comes back until that time it doesn't.

And I've watched retirement.

I watched somebody ride Kmart into bankruptcy.

It was devastating.

Now, they came to me after, like as it was approaching zero.

But it was so devastating because they just had become so conditioned to these difficult times, you know, moving through them and them doing well.

So that being said, assuming you're not drinking the Kool-Aid, And you're just watching, you know, Wall Street, for whatever reason, punish your company stock.

And you're like, this is dumb.

We're doing better than we ever have.

And you would be buying the stock in the employee stock purchase plan.

That's what ESPP means, for those that didn't know.

And you're saying, you know what, I'm going to sell it here, assuming you can.

Logan will talk about that in a second.

but I'm going to sell it.

And let's say you've got a loss or you have very little to no gain.

And so you pay small amount in taxes and you're going to buy it in your Roth.

I like that strategy.

Like, I think that's a good strategy, especially if sometime down the line, you know, you're like friends that I've had in the tech industry over the last five years.