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.



  • http://pfypc.com Mark D. Bullard

    Dan, you said you have three coaches. At first I wondered if you meant three business coaches, but then you mentioned the ironman coach, etc. So, what are the three types of coaches you have and what do they do for you? Also, I’m becoming increasingly convinced that a coach would be a great idea, but I’m hesitant because I’m afraid I’m going to have someone who is just spouting rote truisms at me. When I think about my daughter’s amazing volleyball coach, he is way more knowledgeable about volleyball than her and is helping her refine her skill through specific instruction. I would love a coach like that, but every business is so different than the next. The best coach would be a business professional who’s done what I’m doing. But a lot of coaches just took some coaching training and call themselves coaches. So – what do YOU look for in a coach? Do you look for a specific coach who is strong where you are weak? Thanks Dan!

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