Name: You’ll Regret Playing It Safe in Your 20’s & 30’s
Uploaded: 2025-12-23T11:54:23.000Z
Duration: 8 min 35 s
Description: Thousands of YouTube videos with English-Chinese subtitles! Now you can learn to understand native speakers, expand your vocabulary, and improve your pronunciation...

To-infinitive

What advice would you give to people that are in their 30s or entering their 30s about how to operate in life?

And I don't think it's that much different than in your 20s.

I think every person in their 20s and 30s should lift heavy weights and run long distances in their brain and in the gym.

When you're in your 20s and 30s, you don't even realize.

And in 20 years, you're just going to look back on how strong you were and just marvel at it.

And you're going to wish, as strong as you were, that you even push yourself harder.

I remember in the midst of a race, it's a 2000 meter race, and

I remember not being able to feel my legs starting to black out and having to concentrate on not blacking out from exhaustion.

Tastes like blood and metal in your throat.

And that was at 800 meters and you'd go 2000.

And that ability, just when you think, just when you think you can't take any more, that means you're about a third of the way to your limits as a human, as a species.

Learning that as a young man or woman is a blessing because what it means is you have the confidence that when things are hard, physically, emotionally, mentally, you realize, oh, my God, I could take so much more and still be fine.

And when I worked, my first job was at Morgan Stanley, an investment bank, and

I was undereducated relative to my peer group.

Not because I didn't go to a great school.

I spent the majority of my five years there making bongs out of household items and watching Planet of the Apes.

So I decided every Tuesday morning I was going to come into work and I wasn't going to leave till Wednesday night.

And it sent a signal to the rest of the organization that I came to play.

Develop that kind of grit and strength emotionally, physically and intellectually.

In your 20s and 30s, you're capable of it.

You're just going to look back on that era and be like, just marvel at how out of fucking control strong you are both mentally and physically.

And that sounds very practical or rote, but

you'd rather be good in a big city than great in a small city before you collect dogs and kids.

You know, being in a city is like playing tennis with Roger Federer or Nadal.

When you play with people much better than you, your game gets much better.

You're playing against the best when you're in a city.

Create as many opportunities to find a mate.

Start whenever you're waiting in line at Starbucks.

Develop the skills to begin opening and establishing relationships.

And by the way, the only thing I can guarantee you in life is rejection.

And the only thing I can guarantee a lot of if you want to be successful is a shit ton of rejection.

Being an entrepreneur just means you're willing to take out a big spoon and eat shit all the time.

Talking people into working for you, talking clients into engaging you, talking investors into investing, and

having 90 plus percent of them saying no.

And the same is true with successful mating.

The most important decision you'll make in your 20s and 30s isn't where you live, where you work, what industry you go into.

It's who you decide to partner with, specifically who you decide to ultimately have kids with.

And I have close friends who are monstrously successful by every external metric.

And they don't have great lives because they don't have real partners and their spouses.

And I have other friends who struggle economically.

And it's hard, but everything's a little easier for them because they have a real partner.

And the way you punch above your weight class and find a great mate, you know, emotionally, intellectually, from a value standpoint, sexually, is you give yourself as many opportunities as possible.

And my story is I met my partner, who I had kids with, at the Raleigh Hotel, at the pool at the Raleigh Hotel in South beach about 17 years ago.

It was the middle of the day and I walked in and I think it's important to do this.

I walked in and I saw someone I was really attracted to and I said, I'm going to talk to this person before I leave.

And I promised myself and I went up in the full light of midday sun when she was sitting with another guy and another girl and opened and without the aid of alcohol.

If you Nothing wonderful is going to happen to you unless you take an uncomfortable risk.

Get good at sending blind emails to LinkedIn contacts to ask them for coffee to see if they'll talk to you about that industry.

Reach out to people, tell them you admire them, try and become friends with them.

I was just thinking to myself, I'd love to know this guy.

Get comfortable taking those sorts of risks.

Nothing wonderful will happen to you unless you take an uncomfortable risk.

The most important thing you can find in your life in your 20s and 30s is something that you're good at so that you can start building a base around economic security.

But the real key is to find a great partner, and

that is going to be a function of liquidity.

How many great partners, potential great partners, you approach and unfortunately, the far left of which I'm a part as counseled men that if you start talking to a woman at work and you express any sort of interest, it means you're toxic.

If you don't know the difference between expressing interest in having coffee with someone and harassing them, you've got much bigger problems.