Lessons from 40+ Years of Entrepreneurship | Ilana Golan

The GaryVee Audio Experience

Gary Vaynerchuk

Business, Marketing, Entrepreneurship

4.8 • 18.1K Ratings

🗓️ 10 February 2025

⏱️ 47 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

🔥 In this episode ofThe GaryVee Audio Experience, I sit down withIlana Golan, host of the Leap Academy podcast for a deep dive into the journey of entrepreneurship, personal branding, and the mindset it takes to win.

💡 I get real about my early days—selling baseball cards, working for $2 an hour in my dad’s liquor store, and building a $60M business before striking out on my own. We also cover why personal branding isnon-negotiable in today’s world and how fear is the #1 killer of dreams.

🔑We talk about:

🚀The immigrant hustle—why I had no choice but to be an entrepreneur
💡Personal branding = career insurance (you NEED to build yours)
🔥Fear vs. optimism—which one are you choosing?
💰Why making millions won’t guarantee happiness (but purpose will)
🎯The biggest mistakes people make in career decisions
⏳How to avoid regret & take control of your future

This episode is amust-listen for entrepreneurs, professionals, and anyone looking to break free from limitations. If you’re playing it safe, it’s time to change the game. 🎧🚀

Leap Academy Podcast Links:

Official Website:https://www.leapacademy.com/podcast
Instagram:@ilanagolanleap
YouTube:Ilana Golan - Leap Academy
Spotify:Leap Academy with Ilana Golan
Apple Podcasts:Leap Academy with Ilana Golan

📍DO YOU FOLLOW OUR INSTAGRAM?
📌@garyveeaudioexperience

Transcript

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0:00.0	This is the Gary Vee audio experience.
0:04.8	Gary, we chatted a little bit before we started.
0:08.4	You were entrepreneur from day one, basically, but I want to take you back in time.
0:14.6	So this is going to be all about your career and how you got to where you are.
0:17.5	And you, you know, a small kid yeah immigrant family yes why it's almost like
0:26.9	the reverse it's like it's almost it's funny when you just said why it the answer was that bounce in
0:33.6	my head is like why not? Meaning I had no choice.
0:38.5	I cannot explain in any other way than I'm about to
0:43.6	why entrepreneurship was my life.
0:46.8	Me gravitating towards entrepreneurship when I was six
0:50.3	with lemonade or when it would snow instead of,
0:55.0	you know, I would play a little bit,
0:56.1	but if there was two snow days in a row,
0:58.6	it was impossible that I was sledding,
1:00.5	snowball fighting, playing football in the snow
1:02.8	and making a snowman.
1:04.0	One of those two days, I was ringing doorbells,
1:06.6	shoveling snow, washing cars, trading cards,
1:11.5	and everything I've done in my career.
1:13.7	The only way I can explain it is,
1:15.5	if I was to ask everybody on the other camera right now,
1:18.4	why do you breathe oxygen?
	...

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