Jesse Itzler – How This Dad Shows His Kids Why It’s So Important to Keep Learning

Jesse Itzler – How This Dad Shows His Kids Why It’s So Important to Keep Learning

#14: Jesse Itzler (Part 1) - How This Dad Shows His Kids Why It's So Important to Keep Learning

"My enemy is the clock."

These are words that Jesse Itzler lives by.


Jesse Itzler
in 10 seconds

In today's conversation, you'll learn 3 key things:

Jesse Itzler: Dad Life

Time Stamp: [4:00]

Jesse and his wife Sara Blakely (Sara invented Spanx) don’t just talk about how to live, they are out there doing it.

Every. Single. Day.

You have to work at it.

You have to invest time to schedule things and plan.

That’s a big theme in Jesse’s life.

“Because when you’re in routine, life moves very quickly and you hear it all the time…My kids grow up so quickly.  I wish I did more of this or that.” -Jesse Itzler

Here’s what most days look like for a parent:

We repeat this.  Every. Single. Day.

“How you do anything is how you do everything.” -Jesse Itzler

Jesse is super aware of his relationship with time.

How fast it goes. 

The only way to get in front of it?

Prioritize it.

It’s easy to come up with excuses: “I don’t have enough time.”

And Jesse uses those excuses too, but it still doesn’t mean he’s not going to get in FRONT of it and MAKE IT HAPPEN.

Here’s Jesse with his GIANT calendar he uses to make his time COUNT!

Jesse Itzler
Jesse's travel size calendar | @JesseItzler

Why Jesse is learning 50 new things at age 50

Time Stamp:

When Jesse turned 50, he decided to learn 50 new things.  

So, he hired expert coaches and is learning:

Jesse Itzler learns how to play chess
Jesse learning to play chess | @JesseItzler

What new skill could I learn?

After talking to Jesse, I wondered, what new skills could I learn?

Instead of saying, “I’d like to learn how to play the piano” …and never getting around to it, what’s a mini-skill I can realistically learn?

Hmmmm….How about juggling?

I watched a YouTube video and practiced for 10 minutes per day for 1 week.

I can proudly say I can now juggle!

It’s exciting to learn something new.

And now I can teach my 3 kids too! 

Pro-tip: Don’t worry about dropping the ball EVERY TIME you try the first 2 days. Eventually, it just clicks. Then it’s like riding a bike.

Rob after only 2 weeks of juggling!


“Schedule 1-on-1 time with your kids” 

Rapid Fire Questions with Jesse Itzler:

Time Stamp: [19:00]

– What was your first car? Buick (but really a Schwinn)

– What was your first job? Kiddie pool attendant

– Favorite comedy movie? Airplane

– Favorite standup comedian? Mike Young

– Proudest athletic achievement? Running 100 miles non-stop

– Favorite food to eat? Bananas

– Your kids’ favorite food? Pizza

– Your favorite rap artist?  Group – Run DMC, Solo – Rakim

“If you could have a guest verse on one rap album, what would it be?” (from
Paid in Full by Eric B. and Rakim….or maybe “Bigger and Deafer” by LL Cool J…wait, make it “He’s the DJ, I’m the rapper”, since I really want to meet Will Smith

Jesse Itzler: Rapper

Time Stamp: [22:00]

When I was 15, my friends and I would watch rap videos on a TV station called, The Box.

Our favorite song (….ok, our favorite video) was a song by Jesse Jaymes #1 video, “College Girls”

It took me 25 years to learn….

Jesse Jaymes = Jesse Itzler?!

“It was a SMASH hit on The Box.”

“It wasn’t the song, you guys just liked the video.”

“I wrote that song in college in my dorm.”

1992 Rob says “Thank you, Jesse.”

Watch Jesse's 1992 'College Girls' music video:

Key takeaways:

1) Just because we’re “busy”, doesn’t make it ok to let life pass you by

    – Breaking out of routine is hard for everyone, especially parents

    – Our kids model their behavior not on what we say, but how we act

    – Your enemy is the clock. Start something new.  Now.

2) Jesse SHOWS (not tells) his kids why it’s so important to keep learning

    – Jesse committed to learning 50 new things at age 50 such as:

        • How to play chess

        • How to play ping pong

        • How to hold your breath for 3 minutes!

3) You have to prioritize and SCHEDULE what’s important to you

    – Schedule 1-on-1 time with your kids (especially when you have 4 kids!)

    – Carve out “non-negotiable” time for yourself

    – Put something BIG on your calendar every year

4) Jesse’s rap game is STRONG!

Scooby Doo Mystery Machine fo Halloween | @JesseItzler
Turning their van into the Mystery Machine for Halloween | @JesseItzler

Thank you Jesse, for showing us how we can take our Dad game to the next level!

You can learn more about Jesse Itzler

Get More Jesse In Your Life


Living With a SEAL“It’s hilarious” -LeBron James

Living With the Monks  –“Packed with powerful life lessons” – Lewis Howes



“I took Jesse Itzler’s BYLR course and it OVER-delivered.  His passion is contagious. 

Jesse gives you actionable  tactics about how to spark change and make a real impact in your business, and your life.”

-Rob Roseman


P.S. If you’re a Dad, email me at and I’ll choose 1 Dad to shoutout on the show!

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