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What I Learned by Losing $100,000

What does it mean to “be humbled“?

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I laugh when people win awards and tell you how humbled they are.

I don’t believe you are humbled when you win. I believe you are humbled when you get punched in the face and brought to your knees.

For 2 years I was undefeated flipping houses, making (at least a decent) profit every time.

It wasn’t until my biggest project by far, with huge profit margins potential, that it all went wrong.

In one week:

I lost $100,000 in one deal.

Ended a business partnership.

Witnessed the birth of my first child.

Endured the disappointing look in my wife’s eyes.

I spent the next year repaying investors by pivoting my company towards the next market opportunity, and away from the previous one.

I had no personal liability to my investors. I could have walked away with no financial obligation. Instead, I made one of the worst financial investments but one of the best decisions of my life by buying out their interest in a failed company at full value. Because of this, I could raise capital overnight if I ever need to. But also because of this, I never will.

Not because I’m afraid of failing again, but because of how much I love the slow grind, the process, and the climb, when it all falls on me.

Losing the money humbled me.

Writing that check 1 year later made me feel invincible.

 

Instagram: @skylerirvine

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