January 24, 2020

Side hustle

I was having coffee yesterday with a freelance marketer at Joe & The Juice on Montgomery St. She’s lived in SF for 25 years. Her side hustle is giving chocolate tours on the weekend through a touring agency.1

It reminded me of when I moved to Chicago. I was driving a big yellow Penske truck up I-65. I was going to need help unloading once I got there.

So I searched on Taskrabbit and booked the only guy available on a short 3 hour notice. He was going to meet me at my new apartment and help me unload my table and chairs and bed and boxes.

I almost missed him at first. He was a 60-year-old man wearing glasses and a Northwestern quarter zip. Hey, are you Will?”

This was my mover. Not what I expected.

But we got to work. He was high energy. He’d jog from the door of my apartment back to the truck. He was directing me to unload boxes in a certain order and showing me how to properly lift boxes.

Most people pay money to go to a gym,” he said, but people pay me to work out.”

He then told me that he’s a math professor at Northwestern. He moves people via Taskrabbit on the weekends for the hell of it. He was telling me how he also teaches chess lessons to middle and high schoolers, and how he also will do handyman services for people around his neighborhood.

I loved that.

My mind started spinning with Airbnb Experiences and Taskrabbit at what all was possible. Maybe I should start putting together Ikea furniture for fun.” Maybe Elizabeth should give a running architecture tour in the mornings before work along the riverwalk.” Maybe I can get paid to workout too.”


  1. I asked her if she listed herself on Airbnb Experiences. She said she’s really interested in checking it out. But her hesitation is the rigidity. If one person books a tour it doesn’t matter if nobody else signs up, she has to give the tour.


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