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Five Quiet Hints You’re Dealing with a Trust Fund Baby

by | Apr 4, 2022 | Money

There’s a plague online.

It screws with your ability to make money, start a side hustle, or run a startup.

Trust fund babies.

They’re those sons of b*tches that never have to worry about money because their family is stinking rich.

A great example is the Kardashians. Kim tells us we have to “get our f*cking asses up and work harder” to succeed in business.

Yet she started with $100M left behind in a trust fund from her famous daddy. She can fail 99 times in a row and still be a millionaire.

I’ve never seen the disease of trust fund babies talked about. So here goes.

Here’s how you spot one (more on that soon) so they don’t ruin your business, side hustle, or ability to make money online.

They go from zero to hero fast

Five years ago I was sitting in a cafe sipping a $2 coffee quietly while reading my Harry Potter book.

A colleague comes in and screams “we all need to get a job with this customer!”

The latte went down the wrong hole and I coughed ferociously. (Story of my life.)

“What you talking about old man?” I said.

He goes on to tell me about a client three streets away that offered him a job. They have a fintech business. It’s doing millions of dollars and is only a few months old. In finance, that just doesn’t happen.

A few weeks later, we visit the client to update the information we need to give our risk team. The office has more than 50 desks and no employees. Kinda stranggggeee.

A softly spoken woman begins to tell us how they’re doing millions of dollars of transactions a day. They’d hired a senior executive from a big four consulting firm to represent them. He told us the same info.

To cut a long story short, weeks later we learned the supposed transactions were just them sending money to themselves and their family.


The dude’s rich father funded the whole sh*tshow as a weekend hobby. They folded, never to be heard of again.

Overnight success is code for daddy’s play money.

Their life is a series of highlight reels

Ever spoken to someone who has no failures? I mean even if you’re freaking Keanu Reeves you’ve still failed a bunch of times.

Failure equals human.

These are trust fund babies. Their family protects them from anything that could go wrong to shield them … ohhh cutesies. Oh, and so they don’t get questioned at dinner parties about their children’s misdemeanors.

Expect to see a lot of rejection and failure in any success story. If you don’t, be suspicious as hell about whether generational money acted as a pillowed wall around the person’s life.

They don’t have to work and yet they still eat

This might sound crazy, but loads of people don’t have to work.

They haven’t become CEO or made life-changing money either. And they didn’t win the lottery. Yet they live each day sipping frappuccinos outside cafes on palm-filled streets.

At first it makes zero sense.

Then you learn it’s trust fund money. Often, though, they legitimately do pay for their groceries and utilities (peanuts).

The part they don’t pay for is the roof over their head. That’s daddy’s investment property aka tax write-off. He pays for it while his little basket of specialness lives rent free.

Be wary of people that have never worked a day in their lives. It’s a red flag.

Something feels off

Sometimes you can’t put your finger on it. Something just feels off about a person you meet in business or through your side hustle.

It’s probably a trust fund baby. Trust your BS detector. Trust your gut.

They have daddy’s safety blanket

Other times you meet this strange human and they legitimately do have skin in the game with whatever they’re doing.

Yet they seem to take bigger risks than commonsense would allow for.

That’s a trust fund baby too. Just like in 2008 when the investment banks gambled like drunken sailors on a trip to Las Vegas, trust fund babies can do the same.

Even if they’ve never been told, they know deep down in the cockles of their heart, daddy will come and rescue them with a fresh check from his checkbook if anything goes wrong.

Taking dumb risks is a sign. Be careful.

Why trust fund babies are bad for you

All of this might sound like innocent millionaire games.

It’s not. People get hurt, I tell ya.

These trust fund babies ruin startups, investing, and side hustles. How? Their results are fake. But no one knows so they try to copy them.

It makes normal people have unrealistic expectations about what’s possible. They start to measure their results against the trust fund babies and get frustrated, so they quit too soon.

Things get worse when the silver spoon kids start giving advice. None of it is based on experience so it does more damage than good.

The lesson here is simple. Work with people who have real results. Don’t take money from a trust fund baby because they’ll likely take unnecessary risks — and when it all blows up daddy’s lawyer will be up in your face.

And if none of these five hints reveal the enemy, ask the trust fund baby this question: “Can you show me daddy’s bank account?”

Okay, joking. (Not really.)

Do business and be inspired by executors, not trust fund child actors.

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