Benjamin Arney

If you plan to sell your business in the next 3 to 5 years, what you do now may matter more than the year you sell.

We recently helped an owner preparing for a sale with an 8 figure capital gain.

A few tools we used to shrink his tax bill:

1. A donor advised fund. He gets the deduction the year he funds it and gives over time. We funded it the year before the sale from savings and business cash flow, so the new 0.5% AGI floor didn't hit his sale year.

2. Direct indexing. Instead of one fund, he owns the individual stocks. Some always drop. We sell those for losses and swap into similar ones, so he stays invested.

3. Muni bonds. These are bonds that usually pay interest that is free from federal tax, which is why top bracket earners love them. In September they had their worst month since 2008. We stayed the course, harvested the losses, and they bounced back in October.

Capital losses carry forward indefinitely until used to offset capital gains.

Sell for $10M with $2M of banked losses, and $2M of that gain is wiped out.

The sale is one day. The planning takes years.

Jack: fierce lion, king of the jungle.

Also Jack: asleep by 7:15.

Happy Halloween, everyone 🎃

I have the best job AND clients in the world.

One of my clients loves to collect sports cards and he gave me two Jeremy Doku cards after our meeting this week.

I mentioned that he was my favorite player in one of our meetings, and he remembered.

If you do not follow soccer, Doku is one of the shiftiest wingers in the game right now, and the main reason why I like him so much is because he is open about his faith and uses the platform he has to point at something bigger than himself.

So getting these from a client meant more than he probably realized.

This job is supposed to be about numbers and plans and tax brackets, and most days it is.

Then something like this happens and you remember what it actually is.

I really do love what I do.

Almost all money advice is written as a recipe.

Save 15 percent. Six months of expenses in cash. Max the 401k, then the Roth, then the brokerage.

Recipes are great right up until you are missing an ingredient.

Save 15 percent of what, exactly, when your income swings by six figures depending on the year? Six
months of which expenses, the ones from your best year or your worst one? Max the 401k by when, and does that cost you the match?

The steps do not tell you. They were written for someone with a steady paycheck, and the moment
your situation stops matching the recipe, you are guessing.

If you only teach the steps, people are stuck the second an ingredient is missing. If you teach the system underneath the recipe, they know how to find a substitute.

So instead of save 15 percent, the system is that you are trying to convert a variable income into a fixed savings rate, which means the percentage comes off the top when the check lands rather than out of whatever survives the month.

Instead of six months of expenses, the system is that your emergency fund covers the gap between your worst realistic income and your fixed costs, so the number is different for a rep with a $60,000 base than for one with a $150,000 base.

Instead of max the 401k, the system is that you capture every dollar of free employer money first, then decide where the next dollar has the best after tax outcome.

Same three topics. But the second version keeps working when your comp plan gets rewritten, and the
first one does not.

This is most of why generic advice fails people with variable income. It is not that the advice is wrong. It
is that it was never built for a situation like yours, and nobody handed you the reasoning to adapt it.

Learn the system, not the steps. Then the missing ingredient stops being a problem.

The best tax years of your life are probably the ones right after you stop working.

Think about what happens. Earned income drops to almost nothing. Social Security has not started.

Required distributions are more than a decade away.

For a stretch of years you are sitting in a low bracket holding a large pre tax balance.

That window is the cheapest chance you will ever get to move money from pre tax to Roth.

You convert enough each year to fill the bracket you are comfortable in, pay tax at that lower rate, and
shrink the balance that would otherwise become forced distributions later.

Do nothing and those accounts keep compounding until the IRS requires withdrawals, frequently at a
higher rate than you would have paid during the quiet years.

The mistake is treating retirement as the end of tax planning.

If you stop working at 50, it is the beginning of the most valuable decade of it.

You can have $3 million and still not be able to retire at 50.

Not because the number is wrong. Because of where the money sits.

Most high earners build almost everything inside a 401k. That money is locked behind 59 and a half.

Touch it early and you pay a 10 percent penalty on top of ordinary income tax.

So if you want to stop working at 50, you need close to a decade of spending sitting somewhere you
can actually reach.

That means a taxable brokerage account. No deduction, nothing exciting about it, and the account
almost nobody funds because the 401k feels more productive.

There are workarounds. A 72(t) schedule lets you tap an IRA early, but it locks you into fixed payments for five years or until 59 and a half, whichever is longer. Break it and the penalties come back retroactively.

The cleaner path is building the bridge on purpose, years ahead of the exit.

At your income, early retirement is not a savings problem. It is a sequencing problem.

Something I have been chewing on lately.

I think there are three stages to a man's why, and you kind of graduate into each one.

The first is money. Work hard, climb, make a lot of it. Millions if you can. That was me not that long ago.

The second one hits when you figure out the money is actually doable, or you get there and it does not fill anything.

So the question flips. What am I leaving behind? Whose life did I actually touch?

The third took me a while to see, honestly. Mostly from sitting across from mentors who are a few decades ahead of me and paying attention to how they carry themselves.

It is using what God gave you to honor Him in all of it. Not just the legacy part. The work, how you treat people, all of it.

And from here, the first two look pretty small.

Not that a career and money do not matter. They do to an extent.

Maybe there are more than three levels. I do not know. But I am at the third one and I could not be happier.

My friend Matt and I are the 2026 Cimarron pickleball champions.

Full disclosure. The average age of everyone we played was probably 40 years older than us.

I do feel a little bad about it. Not bad enough to give it back. But a little.

The finals were actually against people I play with every week, which made it more fun and also meant I had to see them two days later like nothing had happened.

Here is the best part though.

The prize is a reserved parking spot with Cimarron Pickleball Champs on it. Just for us. For a whole year.

I have never cared about a parking spot once in my life and now I think about this one constantly.

Come take it from us next year.

At your income, your savings rate matters more than your returns.

Someone earning $100,000 and saving 10 percent needs a strong portfolio to retire early. There is very
little margin for error.

Someone earning $350,000 and saving 35 percent is putting in so much money that returns are almost
a side note for the first decade.

This is the part high earners miss. Enormous energy goes into fund selection and almost none into the
percentage.

Move from saving 15 percent to saving 30 percent and you take years off the timeline, not months. No
investment choice does that.

The reason it does not happen is simple. Income grew and spending grew alongside it, so the percentage stayed flat even as the dollars climbed.

So the question is not what your portfolio returned last year.

It is what percentage of your income left the building before you got used to having it.

Nobody warned me about the daycare plague.

Jack has been going about 7 months now and I think he has been fully healthy for about nine of those days.

Every Monday he picks something new up, and by Wednesday he has generously shared it with me.

So here is the only real advice in this post.

If you are about to have a kid, do NOT get a HDHP. You do not want to be chasing a referral at 7am because a toddler has a fever and the pediatrician is already booked.

Honestly though, the money has not been the hard part. I just quietly stopped buying things for myself and barely noticed.

The sleep is the real cost.