August 26, 2023
Read time: 3 minutes

Your 20’s are full of consequential decisions:

  • Who do you want to marry?
  • Where do you want to live?
  • What makes you happy?

The choices you make in this decade often define how your life will evolve over the next 40 years.

Unfortunately, our education system doesn’t do a great job preparing us for these consequential decisions.

I went to UCLA.

Like many universities, my education skewed theoretical.

As they like to say, my college degree taught me “how to think”.

Valuable—I guess—but in my opinion, sorely lacking.

I spent the first decade of my career trying… stumbling… trying again… failing.

Eventually, things turned out OK.

But it should have been easier.

So today’s issue is meant to help anyone early in their careers.

Here are 3 practical tips about business (and life) you won’t learn from a textbook:

Iconoclasts Win

An iconoclast is someone defined as “determinedly different, a challenger of societal norms.”

On the surface, this seems intimidating.

A title reserved for the Elon Musk’s of the world.

But it doesn’t have to be that way.

We can all aim to be different—or compelling.

People like other people who are interesting.

How do you become interesting?

Dive way too deep into something most people find kind of interesting.

For example, coffee.

Most people like to drink it.

Few people study the origins of coffee and can confidently articulate the subtle nuances of Ethiopia v. Columbia single origin beans.

So if you really like coffee, don’t just drink it like everyone else.

Become an iconoclast.

Be the outlier who takes a strong interest and turns it into a passion.

Then confidently share that passion with others.

They’ll remember (and respect you) for it.

No One Owes You Anything

Most of us, myself included, were raised with a traditional, middle-class upbringing.

We had parents who loved us and showed us their love by serving our needs.

As wonderful as that can be, it has a downside.

Some call it “privilege”, others “entitlement”.

We grow up with things mostly given to us.

And then we expect others, in a career setting, to do the same.

Well here’s the hard truth:

The corporate world doesn’t work that way.

If you want something, you’re going to need to earn it.

And even more importantly, once you earn something you need to take it (ie. advocate for yourself).

In practice, this means shifting the dialogue from:

“I’ll stick around until it’s time for them to promote me.”


“I’ll make myself invaluable and, once I have leverage, advocate for my immediate promotion.”

The former assumes you’re owed something.

The latter assumes you’ll earn (and advocate for) something.

Big difference.

Be a Funnel

Two common things old people tell young people:

  1. Get advice from others (find mentors!)
  2. Don’t be influenced by others (walk your own walk!)

Each piece of advice independently makes sense.

But together, don’t they form a contradiction?

How do you solicit the advice of others, but not become influenced by it?

Here’s how I think about it:

Be an information sponge.

Seek opinions, perspectives, advice from a broad range of highly diverse people across various life stages with different political/religious beliefs.

But then learn how to filter.

Give yourself permission to hear someone’s perspective and then completely ignore it.

In fact, the ability to filter opinions is what makes great leaders great.

A coach takes input from his many assistant coaches, weighs potential biases/blind spots, then makes an informed decision.

Same with CEOs and Capital Allocators.

So the next time a managing partner of your firm tells you he thinks you should do [x] with your career, before letting it affect you, ask:

  • “What about his unique circumstance is influencing his opinion?”
  • “What biases might he have as a result of his unique experience?”
  • “Where might his values and priorities diverge from mine?”

In short, never take advice at face value.

Always filter it based on who it’s coming from.

What worked for one person very often won’t work for you.

Your 20’s are an incredible time for personal growth and professional development.

Full of opportunity, success, disappointment and even failure.

Try to embrace things as they come and never take things too seriously.

Oh and remember, the best is ahead of you 🙂


Over the last year, my business partner and I have acquired two cash-flowing small businesses from retiring Baby Boomers.

We are preparing to raise outside capital to accelerate our playbook and take advantage of a generational wealth transfer.

Over the next 20 years, we plan to buy and own over 50 companies (with no plans to sell).

If you:

  • Admire the success of companies like Berkshire Hathaway, Constellation Software, Permanent Equity and Enduring Ventures
  • Love essential, but “unsexy” (and often niche) businesses
  • Have at least $50,000 of patient capital to invest

For the many of you who already completed the survey—thank you!

We’ll reach out over the coming weeks.

Happy Saturday friends,


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