South Mountain Messaging

Messaging Strategist & Storybrand Guide 

Western Athletic Conference

President of Student Athlete Advisory Committee

Messaging Strategist & Consultant at South Mountain Messaging.

When I was 11 years old, my dad and I scoured the neighborhood for potential lawn mowing clients. A few days earlier, I had pitched my dad on the opportunity to be an "investor" in my grass-cutting venture. 

If my memory is correct, I asked for $365 to buy initial supplies and calculated and pitched my dad on the upside based on how many lawns I could cut that year. Lucky for me, my dad kept the deal terms simple and offered to loan me the $365 if I paid it back. 

Fast forward, and I’ve got everything I need to start making money… except customers. As he and I drove around the neighborhood, we began looking for long grass. Yards that hadn’t been cut in a while. 

Found one. 

“Go knock on that door…”  he prompted me. I was terrified. Slowly, I walked to the porch, hoping they wouldn’t answer. I couldn’t handle the pain of rejection or being told “no thanks.”

They answered. Shoot. I don’t remember what I said, but it must have been good enough to convince them to let me mow their grass. I think my Dad and I had devised a “first mow free” incentive. 

I ended up mowing that lawn every summer for the next seven years until I went to college. 

Since that day, nearly every dollar I’ve earned, I’ve sold myself. Minus a brief stint at the local grocery store in high school and a couple of years of driving Uber in Phoenix (yes, I have some wild stories) in college, I’ve always had to close a deal to make my living. 

At the same time, I have always somewhat resented selling. It can feel awkward. And in the words of Scott Galloway - “asking strangers for money is embarrassing.”

Maybe you can relate....

Jonny Holsten

There's a Better Way to Sell | CEO @ BridgeSelling

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