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One of the Most Underrated Investors Shared the Best Ideas (Perhaps) That I’ve Ever Come Across

by | Jul 25, 2023 | Entrepreneurs

Some people are destined for big things.

Jeremy Giffon is one person that fits the description perfectly. At 14 years old, he was the first employee of a company that sold to Workday (so much for high school and university lol).

Then he joined “Tiny” as their first employee to help them acquire the best internet businesses in existence. It does over $110m of revenue and $50mm of EBITDA. Not bad.

Now Jeremy has gone solo.

He recently went on one of the biggest finance podcasts in the world. The lessons he shared were unconventional. They’re bloody good.

Napkin math beat spreadsheets

Most professional investors are geeks.

They do 6–12 months of due diligence on a startup or investment. If they work at a firm like Tiny, they interrogate the founders. They try to get the best deal and squeeze everyone’s pants for the last cent.

Jeremy thinks that’s stupid. Childish.

When he looks to make an investment he does simple napkin math. Nice round numbers. A focus on profitability not revenue. A modest look at expenses. A realistic view of growth.

With a few basic numbers he can see in an hour whether a startup is worth buying/backing.

The other thing that struck me is he focuses a lot on how trustworthy founders are. He’s looking for small white lies.

If he finds them then he’s out no matter how good the business is. That’s how he avoids partnering with sharks like Softbank and from working with people like Adam Neumann of WeWork fame.

The other trait he looks for in a founder is whether they have faced a major setback/tragedy in life. He says people that have gone through sh*t just have higher mental toughness.

They’ve got a lot of their primary learning out of the way. They can take more of a punch to the face. I thought this was interesting. I’ve never seen personal adversity as a criteria for startup investing.

You can tweet your way onto a yacht

It hasn’t clicked with everyone yet.

Social media gives you an unfair advantage in life. Jeremy is all over this trend. He says in the future there will be co-founders who are Chief Audience Builders. They’ll be brought into a business because of their audience.

Instead of creators monetizing off ads, they’ll monetize by pointing their audience toward a startup that has a complimentary product/service.

The bigger idea here is that posting content on the internet attracts opportunities into your life.

It lets you meet new people too. Now, maybe those people are on a yacht and suck billionaire big kahoonas for dinner (not my kind of peeps).

Or maybe they are influential people who introduce you to new ideas that change your trajectory in life. It doesn’t matter.

Use writing to create a breakthrough in life.

Posting online is the last vestige of the American Dream — Jeremy Giffon

Quarterbacks aren’t driven by envy

A quarterback in football doesn’t envy anyone.

They’ve found their calling and now it’s just about delivery. Jeremy says if you envy others it’s a sign you haven’t found your calling. Stop playing in the mud with pigs, full of envy…and go find your obsession.

Another reason quarterback A-players aren’t full of envy is they need to work together with others for their position on the field to have value.

They’ve figured out life is a team sport.

Pay $57,000 to have lunch with your hero

I see this strategy mentioned a lot.

I rarely see anyone use it. Yes, $57,000 is a lot of money. It might be your entire savings or a year’s salary. Or you might have to borrow the money from friends, family, or investors.

Here’s what an expensive lunch does…

It shows you’re serious about meeting someone that can change your life.

Jeremy says one of the founders of Tiny paid $57,000 to have lunch with well-known investor Bill Ackman. He’s now the largest outside investor in Tiny. Pretty cool. That was game-changing for their firm.

You’ve been lied to by your 9–5 job…

$4 coffees don’t buy meetings with influential people.

4–5 figure lunches do and it’s cheaper than most other options. All you do is reach out to their personal assistant and make a large enough offer to have lunch. If the person is already rich, you can offer to make a large donation to their favorite charity.

Only unsuccessful people send emails and DMs all day asking influential people for free help or to be their “mentor.”

Don’t do it.

“The most successful people respond the fastest”

I didn’t expect this one from Jeremy.

He says successful people respond fast because they’re routers. They know exactly what their role is and they focus on a tiny piece of a bigger vision. Everything else gets routed to the right doer.

You’re not the best person for most requests in life or at work. Figure out who is. Then build a relationship or hire them, then route the requests they can handle the best directly to them. Win-win.

The best opportunities slap you in the face

Jeremy saw a lot of investment deals while working at Tiny.

The best deals always slapped him in the face. They were obvious. And he could communicate them easily in a few sentences. That was enough to get everyone involved excited.

Then there were other deals that required long pros and cons lists. They needed due diligence. They were the deals that were hard to decide on and took up a lot of time. They were never as good.

The “Hell Yes” framework from Derek Sivers is a good rule of thumb. If an opportunity doesn’t make you say “Hell Yes,” it’s probably an obvious no.

Jeremy is a future thinker worth following, similar to the philosophy Naval Ravikant teaches. Learn from him.

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