Here’s an un-boring way to invest that billionaires have quietly leveraged for decades
If you have enough money that you think about buckets for your capital…
Ever invest in something you know will have low returns—just for the sake of diversifying?
CDs… Bonds… REITs… :(
Sure, these “boring” investments have some merits. But you probably overlooked one historically exclusive asset class:
It’s been famously leveraged by billionaires like Bezos and Gates, but just never been widely accessible until now.
It outpaced the S&P 500 (!) overall WITH low correlation to stocks, 1995 to 2025.*
It’s not private equity or real estate. Surprisingly, it’s postwar and contemporary art.
And since 2019, over 70,000 people have started investing in SHARES of artworks featuring legends like Banksy, Basquiat, and Picasso through a platform called Masterworks.
23 exits to date
$1,245,000,000+ invested
Annualized net returns like 17.6%, 17.8%, and 21.5%
My subscribers can SKIP their waitlist and invest in blue-chip art.
Investing involves risk. Past performance not indicative of future returns. Reg A disclosures at masterworks.com/cd
Live: ‘Tis the Season… To Accidentally Wreck Your Budget
December has a unique ability to turn financially responsible adults into raccoons digging through their own wallets at 2 a.m.
Gif by chrixmorix on Giphy, Ah yes, Christmas dumpster diving.
“Should I buy a gift for my roommate’s boyfriend’s dog?”
Suddenly, yes. Obviously.
Holiday spending has range of options from travel, food, and decorations, to random Secret Santas you got peer-pressured into. It adds up faster than Santa heading to the beach on the 26th of December.
So what?
Getting creative with how you save and spend money is especially important this time of year.
If there’s ever a moment to make your credit card points work for you, it’s right now, when every swipe has potential to give something back.
Might as well earn while you hemorrhage.
Learn: How To Use Your Credit Card Points
Most of us collect credit card points the way toddlers collect rocks: obsessively and with zero plan for what to do next.
Here’s your quick guide to understanding the types of points and turning them into something useful.
Step 1: Know What You’ve Got
There are three main types of rewards:
Cash Back: Pretty self-explanatory.
Travel Points (Fixed-Value): Worth a predictable amount when used through your card’s travel portal.
Transferable Points: Flexible, powerful, and confusing if you’ve slept fewer than 6 hours.
Points are typically worth about 1 cent each. But professional credit card maximizers will use transferable points to find deals that maximize the value of each point up to 1.5, 2, or more cents a point.
Step 2: Maximize While You Earn
Credit cards are like the dude at the gym who never hits leg day. They have their strengths and weaknesses.
Most credit cards will offer extra rewards/cash back/points for shopping in specific categories, for example groceries, dining out, or gas.
If you have multiple credit cards, try to use the card that provides the most rewards for the category of purchase you are making. You can determine this by searching up the name of your card, and then “cash back categories,” and you should get the answers you need.
If you only have one card, just use it consistently to earn rewards.
Step 3: Actually Redeem Your Points
A lot of people will let their points stack, smile with glee, and then never use them.
That’s the equivalent of getting $500 in gift cards and then forgetting about them. This is free(ish) money. Use it.
Here’s how to use each type:
Cash Back: Redeem as a statement credit. Anything else (gift cards, Amazon checkout) is usually a not as good a deal. Statement credits pay down your credit card without using your bank… so free money.
Travel Portal Points: Log into your card’s travel portal → Book flight/hotel → Pay with points. Note: this is typically not the best way to redeem travel points, because they often can be transferred for better deals.
Transferable Points: This is how you get bargain flights and hotel stays. Find a flight or hotel you want → compare cash price vs. award price → transfer points from the card to the partner (simplified) → book.
Step 4: Don’t Overthink It
Using points well doesn’t require spreadsheets. It just requires using them.
Remember: points are not wine. They don’t improve with age, and they may lose value, as companies can devalue them over time.
So keep your eye out for deals, but use the points when it feels right. You earned them.
Leverage: Credit Card Offers
Most people think credit card rewards end at points and cash back.
Plot twist: many cards quietly offer rotating deals, discounts, and bonus multipliers on points that you only notice if you scroll past the part of the app trying to sell you a loan. Forget the loan.
To find these offers, click on your card and then scroll down or select the menu option for something like “offers,” “deals,” or “promotions.”
What these deals usually look like:
Extra cash back at grocery stores or gas stations
Discounts at online retailers
Bonus points for travel bookings
Holiday-specific boosts for dining, shopping, or delivery apps
Pros:
Genuinely good savings if matched to your normal spending.
Often includes surprisingly useful holiday offers.
Can stack with points you’re already earning.
Cons:
Deals rotate constantly, so you have to check every month.
Easy to justify impulse purchases “because there’s a deal.”
You must manually “activate” offers (because nothing can ever be simple).
You may be required to hit spending minimums on certain deals. Beware of this.
When it’s worth using:
When the deal matches something you already planned to buy.
If not? Scroll on.
Also, quick reminder that I am not sponsored by any of the tools I note here. I wish I was! These are just the tools I use.
Launch!
Do a 60-Second Reward Check.
Right now, open your credit card app and:
Look at how much points/cash back you have and how much it’s worth.
Check the active deals.
Activate all the ones you’ll actually use this month.
This tiny habit takes less time than heating leftovers, and it can save you real money over the holidays.
Stay holly and jolly, my friends. ;)
Hey!
Thank you so much for being a part of this newsletter. I am grateful to write to you weekly and I hope this helps you feel more confident with your finances.
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—Ben Brosnahan
