Entrepreneurs Unpluggd in Chicago!

The first ever Entrepreneurs Unpluggd event in Chicago, organized by Stella Fayman and Tim Jahn, was a relatively intimate gathering of like-minded individuals, brought together to hear the stories of some of the most successful online business owners around. Since I’m on a journey to starting a media social enterprise of my own, I figured it’d be a really good learning opportunity. The lineup for the night? The founders of Sittercity.com, ContactKarma.com, FoiledCupcakes.com, crowdSPRING.com and GrubHub.com. Pretty impressive stuff!

Missed out on the event? No worries. Here’s a quick re-cap of what went down:

Genevieve Thiers – SitterCity.com SitterCity Logo

“Don’t let perfect be the enemy of good.”

  • Started what’s essentially a match.com for parents and caregivers when she saw a pregnant woman walking around campus flyering for a nanny.
  • Startup cost was $12K and it was just her and her laptop for the first 4 years.
  • Marketing your online company has 3 stages: Grassroots level -> Direct Marketing -> Brand Marketing
  • Pitched herself as the “babysitting expert”, which later landed her 6 segments on The Today Show.

YSL: She’s essentially taken what people were already doing, and put the process online. Brilliant.

Dan Ratner – ContactKarma.com ContactKarma Logo

“Customer = someone who pays you for stuff.”

  • Started a service for finding vendors your friends use. Site’s still in beta.
  • Selling to small businesses is just as hard as selling to big ones
  • Get the customer to tell you what they need
  • Talk about your product. A lot.
  • Sometimes intuition is not the same as reality

YSL: Interesting concept that’s kinda like yelp.com and facebook rolled into one. Injects some fun into searching for services.

Mari Luangrath – FoiledCupcakes.com FoiledCupcakes Logo

“People love opportunities to interact with other people with common interests.”

  • Found there was no bakery around that would deliver cupcakes to her without charging exorbitant delivery fees.
  • Started this online cupcake store 1.5 years ago with social media as her only form of marketing
  • Targeted office admins because they wanted to sell by the dozens. Who organizes parties? Who has $$?
  • Hire people who are smarter than you

YSL: Those cupcakes look delicious. Keeping them in mind for my company’s next event! I loved the way they handled a mistake they’d recently made. It’s a great example of what to do.

Ross Kimbarovsky – crowdSPRING.com CrowdSpring Logo

“Look bigger than you are.”

  • Wanted to help small and mid-sized businesses find graphic design services more easily
  • Found first buyers by paying friends to post projects on their site
  • Held a public project where designers were invited to compete to design the crowdSPRING site.
  • Had to very carefully manage the backlash from the design community because they were changing the way the world of design worked.

YSL: I love this. Crowdsourced design services. Just what I’ll need for when I revamp my website! Discovered them when they featured JJ’s List on their blog as one of the top influencers in the world of crowdsourcing.

Matt Maloney – GrubHub.com grubhub logo

“Find a good partner who brings different perspectives and skill sets to the company.”

  • Started online food delivery directory in 2004 when he got sick of pizza delivery from this one place
  • Started with 2 people in his house
  • Customer Service must be at the core of his business.
  • In case of a screw up, make the resolution A LOT better than the problem.

YSL: This is the only service that I’d actually used before the event. Definitely made my being sick and unable to go out to buy food a lot easier to manage. Their ads are peppered all over the trains… which I would imagine has paid off well for them, since that’s how I discovered them in the first place.

What a great event. Thanks Stella and Tim for organizing this. I can’t wait for the next one!