The Struggling Founder’s Checklist to HumbleBragging

The recipe to attracting buyers & investors–you are told–is to be “authentic” and “humble”.

That’s true. No arguments from me.

But the problem founders have is they post the most cringey krap to flex authenticity.

Many of them aren’t even aware of how they look–and why nobody wants to buy from them.

I’m here to ensure you don’t make the same mistake. 

So, here is a checklist I wrote to help you out. 

I call it the “The Struggling Founder’s Checklist to Humble Bragging”.

Be honest with yourself if you’re doing any of these on a regular basis. 

Do you…..

  • Post on LinkedIn about the lessons you learned going from being broke to making boatloads of money?
  • Talk about the struggles of bootstrapping–even if you’re a trust fund baby?
  • Neglect  to mention that your “bootstrapping” was talking to your fellow Yale/Stanford/Columbia  alumni at a dinner party?
  • Post on LinkedIn with book recommendations that include the works of Tim Ferris, Simon Sinek, or Tom Peters?
  • Tag a bunch of  more established founders, tech gurus, and sales leaders   with your top 3-20  lessons you learned from them–and hoping they respond?
  • Post about how you asked an interviewee about a gap in their work history—but gave them a job anyway?
  • Write a (fake) story about how a homeless guy on the street asked you for change–but you gave him a job instead?
  • Pretend that meditation and cold showers are required activities to be rich?
  • Wear rosaries as accessories?

As I said, be honest with yourself. If you have a legitimate business and want to trend these hurtful tactics, I might be able to help you. 

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