5 Expensive Mistakes I’ve Made in My 30s That Could’ve Ruined My Life After 40

5 Expensive Mistakes I’ve Made in My 30s That Could’ve Ruined My Life After 40

A few weeks ago, I owned up to the biggest mistakes I made in my 20s… mistakes that cost me literally millions.

This video is the sequel.

Believe it or not, when I turned 30 I didn’t magically become an angel, with a perfect track record of success. 

(Shock! I can hear your gasps from here)

I squared up to that decade as a new man, confident and determined to avoid past mistakes.

…but immediately started making new mistakes!

The reason I’m sharing this is:

  1. To humanize me (I’m not a flawless success story, I’m a patchwork of mistakes.)
  2. To show you that mistakes are ok (Heck, they’re necessary.)
  3. So you can avoid my mistakes (Don’t screw up the way I did.)

My 30s started out strong.

I was on the brink of exiting my second company, Flowtown, ready to add a few more zeroes to my bank balance.

Right after that, I started Clarity.fm and without any help from co-founders, I scaled the company, closed $1.6M in funding from investors like Mark Cuban, then successfully exited that company too… 

…and then launched one of the biggest YouTube channels for SaaS Entrepreneurs.

But during this decade, I faced a new beast:


My 30s was full of mistakes that came from within me. Broken thinking.

I had to reinvent myself – more than once – to become the leader I needed to be.

Please… don’t make the mistakes I did. 

Watch my latest video where I roast myself, shake your head at my expense (I encourage it) but don’t repeat my screw ups.



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Today I’m sharing with you:

  • How I lost 30 – 40% in market value by drifting
  • The wrong narratives that shaped my leadership
  • The day I knew I crossed the line (and I had to change)
  • My anti-portfolio mistakes
  • How I passed on a $250M company *face-palm*
  • Why I have 3 coaches… right now

Look, I get it.

Every advert in your feed, every case-study in your inbox, every silicon valley interview is screaming “SUCCESS!!” right in your face.

You just want a break, right?

I hope you can see that that’s why I make these videos.

It’s not to show off or to wave dollar signs in your face.

It’s because I want you to live a better, more fulfilling life while growing a richer business.

That’s what motivates me even if it means sharing my embarrassing mistakes. I hope you can see that I’m doing my best to help.


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