Every entrepreneur faces rejection, but not every rejection tells the same story. Sometimes what feels like a devastating “no” in the moment reveals itself as a blessing in disguise. This is the story of how one investor’s deceptive behavior taught me that some rejections are actually protection.
Table of Contents
The Setup
In one of my first businesses, we were almost out of money. An investor who had been stringing us along for months invited us to a steak dinner to discuss the terms of his investment.
We never would have chosen this restaurant, and my partner and I tried to order the cheapest thing on the menu.
Red Flags in Plain Sight
The evening should have been a celebration of our upcoming partnership. Instead, it became a masterclass in recognizing red flags.
While we carefully selected the most affordable options, conscious of our dwindling funds, our potential investor showed no such restraint.
Looking back, there were signs long before the dinner. Follow-ups that went unanswered for weeks. Last-minute cancellations with no explanation. Vague answers every time we pressed for a timeline.
Each one felt excusable on its own. Busy schedule. Competing priorities. But together? They were telling us exactly who this person was.
We just weren’t listening.
Moment of Truth
When the bill came, the investor said, “How do you wanna do this?” dropped a $50 bill on the table, and left in his $200,000 car.
His steak alone was $49.99.
Unsurprisingly, he never invested in our company.
Resilience in the face of rejection is one of the human skills I discuss in The Human Skills That Make Us Irreplaceable.
How to Read the Room Earlier
Now I watch for signals before any dinner happens.
How someone treats the waiter. Whether they make eye contact or spend the meal scanning the room. How they talk about the last deal that fell apart, the last founder they passed on.
And this: do they ask about you, or do they just perform interest?
There’s a difference. You can feel it. Real interest has follow-up questions. Performed interest has a tell: the pivot back to themselves, every time.
I do most of my reading in the first five minutes now. Not the pitch. The handshake. The small talk before anything is at stake. That’s when people are most themselves.
What signals are you still ignoring?
Conclusion
This experience taught me that some rejections are protection in disguise. The investor who seemed like our salvation would have likely brought more problems than solutions.
In fact, a couple of years ago, I saw an article about him being sued by the federal government for massive tax fraud.
In that moment, everything clicked into place. What had felt like rejection was actually protection.
The bottom line? Not every open door is worth walking through. Some closed doors are the universe doing you a favor.