I’ve invested 100’s of millions of dollars, and lost my fair share of deals…
Here’s 19 contrarian lessons about investing & making money:
Learning is the cheapest form of investing
Hard to get a negative ROI, and can pay dividends for years.
When I was young and dumb I was young and dumb.
Which usually means too loose and inexperienced.
Investing has an insider language.
Learn the language and you can enter the club.
I carried a book around in ibanking filled w/ unknown terms:
ROI, IRR, waterfall, ratchet…
Master modeling.
With an excel sheet you can peak into potential futures to believe them or sell others on your dreams.
Most people watch interviews, instead read annual reports.
One tells a tale, one shows the truth.
If I’m faced with a difficult investment decision and I can’t decide… my answer is no.
The best investors are always investing.
It looks like work to others, but it feels like play to them.
That’s how no one can compete.
Because They’re investing, for 12-16 hours a day.
Most suffering in investing comes from not asking enough questions.
The smartest investors ask the dumb questions, unapologetically.
Super power words for you: I do not understand.
Become the best at your target niche.
Refine what you invest in until true.
Opportunities will find you.
Then luck becomes destiny.
My wealth wasn’t made in 1 giant year
It grew little but little until the little mounds stacked up into mountains.
Have a viewpoint on the world and a reason for every dollar you allocate.
And the reason isn’t because I think other people will keep piling in to price speculate.
Those who practice the greater fools theory eventually are the fool
Amateurs talk ROI pros talk investment thesis.
Roi is a lagging indicator, thesis is a forward looking expectation.
Don’t tell me where you’ve been tell me where you’re going to take me.
Investing time & Money: Buy vs build.
“Look at where the two lines will intersect and determine if cheaper to buy or to build. Usually the answer is in acquisition, which eliminates a lot of the risk” - Sam Zell
Don’t become a deal junkie.
I love doing deals but I’m not addicted to it.
How to avoid addiction? Skin in the game.
Never done a deal without my own money on the table.
Follow the incentives they’ll show you the outcomes.
Do you make money only on management fee? How much $ do you as an investor have in the deal? Do they make money if you lose $?
You’d be surprise how often the incentives are bad.
Speed to no is an indicator of aptitude.
Dont waste people’s time on deals. That means you don’t know what you’re looking for.
How do you win if you don’t know what you’re searching for?
Become a historian of your deals done and passed.
I write a thesis on why I invested or passed on every deal. I’m amazed how often my mistakes repeat.
I never would have seen it if I didn’t write my own history book.
Shout your needs from the rooftops.
What if people are looking for exactly you to do their deal? But you’ve played too small, you’ve risked too little.
So they’ll never know.
Advice can often lead to allocations.
There is a reason your twitter is filled with investors offering free tidbits.
They aren’t nice. They aren’t chasing fame. They’re chasing unfair dealflow.
You can do the same.
Consumer voraciously all you can.
My library is filled with books from investors who have lived and allocated across generations.
They made mistakes so I don’t have to repeat them.
I write threads breaking down money, contrarian ideas and investing 1-2x a week.