The hardest sale you’ll ever make is selling yourself

Rejection is easy. You know what’s hard? Selling yourself.

Sales is a numbers game—every "no" paradoxically brings you closer to a "yes."

So, if rejection isn’t the most challenging part… what is?

Getting people to trust you.

But how do you build trust?

That’s unique to you.

I’m very direct and honest, but as an ex-comic, I can get away with it because people will laugh at my delivery—and I’m always kind.

I’ve been in sales my whole life across different industries, and it’s always the same—if you can’t sell yourself, you won’t sell anything.

When I started in real estate, my first listing presentation was from a mailing I sent to a building—I was meeting virtual strangers.  I walked in armed with a thick presentation, market comps, and data.

But that’s not what they wanted.

They wanted jokes.

I almost missed the sale trying to sound “professional” instead of just being me.

So, I dropped the pitch and told stories instead.

The next day, I followed up, and to my shock, they told me to send the listing agreement.

Lesson learned: Showing up, taking a risk, being yourself—that’s what makes someone want to work with you.

Not being who you think they want. Being who you actually are.

This applies in any sales role—whether you’re convincing a doctor to try a new product, selling a service, or guiding a seller through a tough market.