Last Time the Market Was This Expensive, Investors Waited 14 Years to Break Even
In 1999, the S&P 500 peaked. Then it took 14 years to gradually recover by 2013.
Today? Goldman Sachs sounds crazy forecasting 3% returns for 2024 to 2034.
But we’re currently seeing the highest price for the S&P 500 compared to earnings since the dot-com boom.
So, maybe that’s why they’re not alone; Vanguard projects about 5%.
In fact, now just about everything seems priced near all time highs. Equities, gold, crypto, etc.
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It’s post war and contemporary art.
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*Investing involves risk. Past performance is not indicative of future returns. Important Reg A disclosures: masterworks.com/cd.
Someone asked me yesterday why I’d rather finance a new vehicle than just pay cash for a used one.
On the surface, paying cash sounds responsible.
No debt.
No payment.
No interest.
No bank or lender involved.
But that logic doesn’t hold up inside a real, growing service business.
Here’s why.
The Tax Math Changes the Deal Immediately
A new truck can be depreciated on an accelerated schedule.
That means instead of slowly writing it off over many years, you can often deduct a large portion of the purchase price up front, reducing taxable income right away.
Example:
If you buy a $90,000 truck and can deduct a large chunk of that in year one, and you’re in a combined federal/state tax bracket of, say, 30%—
That’s roughly $27,000 back in tax savings.
So the real cost of that truck is no longer $90,000.
It’s materially less.
That alone changes the math compared to paying cash for a used truck with limited or slower depreciation benefits. And not to mention the ironclad warranties on a new truck.
Downtime Is the Silent Killer
More importantly, new trucks don’t live in the shop.
They don’t:
nickel and dime you with repairs
randomly take you off the road
kill your ability to run a full schedule
Downtime is expensive.
A truck in the shop isn’t just a repair bill either.
It’s:
missed jobs
missed revenue
crews waiting around
guys looking for other work
momentum completely disrupted
That cost never shows up cleanly on a spreadsheet.
But it always shows up in your bank account.
Cash Matters More Than Ownership
Cash gives you options.
Cash lets you:
scale when opportunity shows up
absorb slow weeks
handle emergencies without panic
keep flexibility
Once you dump cash into a used truck, that money is locked up.
It’s in the truck.
It’s no longer liquid.
You can’t pull it back out when something else breaks.
And here’s the part most people get backwards:
A truck isn’t an asset because you own it outright.
It’s an asset because it stays on the road and makes you more money.
That’s what assets are supposed to do.
Enhance cash flow.
Produce more than they cost.
Financing equipment does three important things at once:
it keeps you operational
it keeps cash in reserve or to be deployed into marketing
it keeps you earning every single week
That’s not reckless at all!
That’s discipline.
The Rule I Use
My rule is simple:
Only use debt for income-producing assets.
Never for anything else.
Protect cash for scale and survival during slow periods.
That mindset has saved me far more money than “owning things outright” ever did.
One More Thing People Miss
If you’re running a real business, you’re not trying to make just enough money to pay for the things you buy.
You buy trucks and equipment for one reason:
to grow.
You only consider financing—new or used—if:
you plan to bring in more jobs
you plan to hire people
you already have the work, or clear signs the work is coming
If that’s not true, the question isn’t new vs used.
It’s whether you should be buying at all.
Let’s get it 🫡
— Justin ✌️ & Tony 🏁
P.S. If you’re looking to finance a truck or heavy equipment and want a solid, no-nonsense connection, we’ve got a great one. Just reply to this email and I’ll make the intro.
Have questions? Hit reply and let us know.


