The Homeless Entrepreneur

Jason Byer
The Coffeelicious
Published in
3 min readJan 11, 2017

It’s 8 degrees in Chicago, five days into 2017, and I debated taking an Uber from the train station instead of walking the 1 mile to my office in the West Loop at Startup Foundry.

Half way through the walk I see, Larry, directing traffic for those exiting the I-90 off ramp and trying to merge onto Lake street. In the morning Lake street is very congested and frustrated commuters generally don’t let you merge (this is the midwest, though, so we politely turn our heads acting like we don’t see you). I don’t always walk this route but it’s not the first time I have seen Larry.

Several months before I saw him sitting on a crate asking for money at the same intersection. In what seemed like a one-time event he got up from his seat to stop traffic to help a truck driver get through the intersection. However, the next day he was standing near the intersection helping others navigate the busy traffic.

After witnessing this transformation in a homeless man most people pass by I realized that it’s Larry who is the true entrepreneur amongst the thousands of eager people rushing for that title.

With temperatures this cold you cant help but admire his entrepreneurial spirit. Larry doesn’t have a boss making sure he shows up to “work” but he still comes most mornings from 7–9am during the morning rush.

“I just want to prevent accidents and make sure everyone gets a smile on their way to work”

How would you spend your early morning if you didn’t have a job and the weather was well below freezing?

This title is actually misleading because Larry recently got an apartment near Harlem Ave in Chicago a couple of weeks ago. But to most of us we just see Larry’s outward appearance. We suspect he is just another homeless person instead of the entrepreneur he is.

I stopped to shake Larry’s hand and ask what he wanted this new year. He used to make $14/hour doing machine work and die casting until his left forearm snapped through his skin.

What he would like to do is own several vans to make deliveries and offer catering services since he likes serving people and feels that the demand isn’t going away.

Video with permission from Larry 1/5/2017

Entrepreneurs are opportunists who want to make a difference. Larry, has found a way to receive meals and donations from the regular commuters by providing a valuable service instead of simply begging.

What kind of person are you?

  1. Are you waiting for opportunities or are you working every day to find those opportunities even if the situation isn't perfect?
  2. Are you truly adding value or are you simply looking for a handout?
  3. Are you complaining about your situation or do you still have a goal for where you want to go no matter how far away it seems?

I am reminded of the quote from Ryan Holiday in- Ego is the Enemy:

“Impressing people is utterly different from being truly impressive.”

Larry might not be impressing people to the same degree we revere Silicon Valley entrepreneurs but his actions and positivity are truly impressive. He has drive and he is showing up even though life has dealt him a bad hand at the moment.

Larry is the type of person we should want to be in 2017.

Know anyone that’s got an opportunity for Larry?

You can normally find him at the intersection of Lake street and the I-90 Northbound off ramp between 7–9am. Larry wants to own a delivery or catering service and continue to make other people happy. His drive makes him more qualified than most people I know.

Jason Byer builds partnerships and marketing for crowdSPRING.com and StartupFoundry.com

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Jason Byer
The Coffeelicious

Passionate about creating innovative companies @ StartupFoundry. Enjoy endurance races, craft beer and family.