I’m four days into gathering documentation to pay 2025 taxes.
Here are a few important lessons you might find useful:
1 – Avoid tax shelters
Every entrepreneur that makes a good deal of money eventually faces the day when he or she must write a large check to the government.
The entrepreneur then goes down the inevitable rabbit hole of ways to reduce taxes.
- No income tax states
- Offshore companies
- Conservation easements
- Life insurance
- Real estate
- Opportunity zones
- Trusts
- Oil & gas partnerships
My advice: just pay your taxes.
Anytime anybody offers you a tax savings strategy in which they earn a large commission, run the other way.
Every tax savings strategy complicates your life, involves some level of legal risk, and often ends up costing you more than it saves
Here’s the simple way to reduce your taxes:
- Build or buy assets (businesses, stocks, real estate, etc.)
- Don’t sell them
If you can reinvest profits in a business at a high rate of return, do so. Whatever you can’t reinvest is taxable profit. Good.
Pay your taxes.
2 – Do the worst thing first every day
Charlie Munger often spoke of Granny’s Rule: eat your carrots before dessert.
I too often fail to follow this advice.
Doing so makes me miserable.
I don’t exactly sit around and watch reality TV in the morning. I’ll write, create, read, or plan, all useful activities.
However, I’ll often do those things to avoid doing what is uncomfortable, provides no immediate reward, and I despise.
Like tax preparation.
It’s better to do the most annoying, most necessary things first every day.
You reward yourself with the work or activities you most enjoy.
Eventually, with enough annoying work-reward cycles, you make discipline automatic.
You slowly rise, becoming a stronger, more capable, more reliable, more successful person.
3 – Most things don’t take as long as you think they will
Starting a despised task the hardest.
That’s why you do it first thing in the morning.
Once you start, however, you often realize that the size of the task was much larger in your mind than in reality.
Most things we dread are often smaller than we anticipated.
So get started.
4 – Heroic consistency over heroic effort
I recently read a book on excellence by Brad Stulberg.
The main lesson I took away from that book is on consistency.
I too often have prided myself on how much I can accomplish in a short period of time.
What matters more is how much one can accomplish over a long period of time.
The tortoise, slowly chugging along, accumulates more miles than the hare that starts and stops.
Some things, especially hard things, are more easily done by chipping away than by one smash with a sledgehammer.
What produces the greatest long-term results is a gigantic volume of total work, not how much work was done in any individual day, week, or month.
Keep chipping away.
In case you skipped to the bottom of this email, here’s the summary:
- Avoid tax savings strategies that earn promoters large commissions
- Just pay your taxes
- Do your most dreaded tasks first thing in the morning
- Most of what you avoid doesn’t take as long as you think it will
- Consistency beats short-term heroic effort
—Matt
