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Why our cities are soft tomatoes🍅

Jackie DiMonte
3 min read · Jul 25, 2019

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🛴1/ Scooters are taking over Chicago and the city is not taking it lightly!

But don’t take my word for it, jump on your favorite social media platform to follow the
backlash.

Instagram accounts dedicated to documenting scooter mishaps in Chicago

🛴2/ If you also reside in a city with scooters, you know that this controversy is not
exclusive to Chicago.

Scooters are a great solution for cities, but often solve one set of problems by causing
another.

🛴3/ At the core of the conflict is our cities’ infrastructure: it has not yet evolved to
meet the needs of scooters.

🛴4/ You know what I’m talking about if you’ve ever driven behind a slow-moving
group of scooters. Or if you’ve come across them head-on on a one-way.

If you’ve been on those scooters and were aware of the anxiety you were causing, you
know what I’m talking about too.

City infrastructure related to scooters

🛴5/ Cities comprise hard and soft infrastructure. Both are inadequate when it comes
to scooters.
Hard → Where’s the best place for me to park outside my friend’s house? The parking
space? The sidewalk? [Ah, ok, I’ll just leave it in the street]

Soft → Do I keep to the bike lane at stop signs? How do I make left turns without getting
hit?

🛴6/ We see this conflict happen over and over as new technologies emerge

We identify a problem

We develop a solution using technology

We realize the technology does not fit into the existing system

We make adjustments to the system so that the technology works well

Process of introducing new technologies into existing environments

🛴7/ Florent Crivello coined this the “tough tomato principle.” Growers adapted
tomatoes so that mechanical harvesters could work.
 Tough Tomato Principle

🛴8/ And like tough tomatoes, our cities will need to adapt.

Tough tomato principle applied to scooters in cities

🛴9/ If scooters persist, I have little doubt that we can adjust our infrastructure, soft
and hard, over time.
The clearest analog is Chicago’s bike initiative, Divvy (Ford GoBike in SF, CitiBike in
NYC). It impacts the development of our bike lanes, street traffic, and commuting
habits.

🛴10/ But for now, our cities are still soft tomatoes.
Scooters Chicago Startup Technology Venture Capital

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Written by Jackie DiMonte

176 Followers

Early stage venture investor at @chicagoventures. Formerly @hydeparkvp, #IoT at @silverspringnet, and #tech
at @Accenture

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