So what's it like to quit your job and jump head on into a startup without the guarantee of a steady paycheck?
Ryan Coon, 28 of Old Town, said it's quite invigorating once the initial shock wears off.
"Walking in to work today I was thinking 'Wow, today is gonna be a cool day,' " the Rentalutions co-founder said. "It's certainly challenging, but it drives you to get up every day."
Coon and Laurence Jankelow, 28 of Old Town, are spending their days trying to build an empire in a shared office space in the 1871 startup community on the Merchandise Mart's 12th floor.
"Typical day, we get in, we have our quick partner meeting," Jankelow said. "We talk about our top five priorities, what we need to get out. From there, it's really connecting with customers, getting feedback, talking with developers."
Jankelow said they pay $400 per month per desk for their office space, which consists of a pair of desks in the back part of the room covered with doughnuts, papers and bottles of water, the leftover detritus from their marathon work days.
A Fisher-Price toddler's basketball hoop was brought in to make it feel a little more like home.
"We think it's definitely worth it," Coon said. "We end up eating free pizza 2, 3, 4 times a week up here."
"Maybe not $400 worth of free pizza," Jankelow added.
Of course in the startup world, you've gotta worry about a lot more than just a mean boss or annoying co-workers. With just the two of them on staff, the pair are their own sales, human resources, management and IT staff, often finding themselves at the mercy of others and presenting some rather unique hurdles
"Yesterday morning, the Amazon server farm in Virginia went down, so our site was down for a bit because we're hosted on Amazon," Coon said. "It's things like that that you can't plan for, you can't count on. Every day is different."
So how much money have Coon and Jankelow made since quitting their $100k+ per-year jobs?
"None," Coon said laughing.
"We're still pre-revenue," Jankelow added. "It's definitely high-risk, I would say."
With Jankelow having recently gotten married and Coon being in a long-term relationship, both men said their dream has an expiration date to start bearing fruit in the form of a steady paycheck.
"It works for now, but it won't forever," Coon admits.
But for now, it works.
"If I were to spend $100 grand on an MBA, I don't think I would learn as much as I'm learning right now," Jankelow said. "Here our upside is just too overwhelming."
Matt Lindner is a RedEye special contributor.
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