The Greatest Startups in Chicago History, and Their Proteges

When you think about the many different, successful tech ecosystems spread across the US there are a few givens that just can’t be dethroned. You’ve got New York, Silicon Valley, and Washington DC for sure, but I’d also say that you have to include Chicago as well.
If you think otherwise, I’d push you to dig in deeper to the city’s rich culture of startup companies. Not only do they have the quintessential Midwest mindset, they also show strong support for females in tech and offer an incredible amount of resources for entrepreneurs. This celebration of the Chicago ecosystem is brought to you by @properties, the leading Chicago real estate brokerage serving both the city of Chicago and North Shore through dynamic marketing and innovation. Follow the full content series here.
Not to mention, it’s where our own CEO Frank Gruber hails from, so we know it produces some top notch talent. Outside of that though, there’s a whole list of damn good reasons to startup in the Windy City.
Chief among any of these reasons, though, is the amount of local success they’ve produced and maintained since the days of the .com boom. To that end we’ve gone in and uncovered some of the greatest startups in Chicago’s history that have helped put the city on the map and are still kicking today:
Basecamp: While the company has their operation spread out across 26 different cities, they’ve maintained their HQ in Chicago since they got their start back in 1999 – 37signals at the time. Over the years they’ve remained committed to helping companies and teams focus on one common goal: finishing a project together. It’s actually something they focused on internally when Jason Fried decided to pivot 37signals’ main effort towards their best product, Basecamp: “We’ve become a bit scattered, a bit diluted. Nobody does their best work when they’re spread too thin. We certainly don’t. We do our best work when we’re all focused on one thing.”
Belly: They were founded on the principle of making loyalty rewards easily accessible to all customers and readily available at every business. The Belly team offers different programs that cater to each business’s personality, culture, brand, and objectives in order to foster more personal relationships with their customers. It’s that kind of attitude and attention to detail that landed them in Dell’s Founders Club 50 an elite society with access to exclusive efforts and resources provided by Dell.
Edmodo: Although they’re currently operated out of San Mateo, CA, Edmodo started up in Chicago when two school district employees set out to bridge the gap between how students live their lives and how they learn in school. They’re now the number one K-12 social learning network in the world. Back in 2010 they got a round of funding from Union Square Ventures, who summed up their expertise: “Edmodo is based on the premise that teachers need an easy way to share content with their students. Around this central concept, Edmodo has created a social and mobile experience that appears to be resonating well with teachers and students. The team at Edmodo, existing investor Learn Capital, and we are committed to supporting the learning community in schools across the country and the world.”
Groupon: Everybody is familiar with Groupon at this point. Further, everybody is more acutely aware of the troubles they encountered while on their startup journey. However, you don’t get to become one of the greatest of all time without your challenges. What separated Groupon from other companies was how they dealt with their shortcomings. In 2014 they made some big announcements about how they plan on owning the market as they recovered and moved forward into the future. They put their heads down to focus on charity, partnerships, merchant services, acquisition, and travel in an effort to shake things up: it definitely worked for them.
Grubhub: The nation’s leading online and mobile food ordering company has been long dedicated to connecting hungry diners with local takeout restaurants. In fact, their platforms allow diners to order from around 35,000 restaurants in over 900 US cities and London. They’ve maintained a strong commitment to always putting the needs and wants of their users first and foremost, going so far as to implement an ordering setup in their own office to ensure everything worked properly. We’ve had the pleasure of covering and following GrubHub since their early, early days in Chicago and we’ll follow them for, well, forever.
These next five startups might not be Chicago’s greatest yet, but they’re definitely well on their way to greatness.
Charlie: This tool compiles one page summaries on the people you’re about to meet with, before you see them. An hour before every meeting in your calendar, Charlie makes sure you walk in with the intel you need to make a killer impression: breaking news on their company, the passions and hobbies you both had no clue you shared, and stheir professional history.
MentorMob: Billed as a crowdsourced learning website, MentorMob consists of a community of enthusiasts who curate online courses from the web’s best content. Everything is organized into comprehensive courses that can teach you everything from entrepreneurship tips to snowboarding. Each course covers beginning, intermediate and expert skill levels, building a full, free online class for you from existing online content.
MobileX Labs: It’s their express goal to change the mobile landscape of how artists and companies currently interact with fans and followers. To that end they offer ways to make an iPhone app in five minutes or less. Specifically they have MXL Build, MXL Apps, and MXL Games – curriculums that are all designed to teach users how to build their best apps and games with little to no coding.
Silver Chalice: This next-generation digital sports media company owns and operates multiple digital networks as well as a standalone tech division. The founders built their platform on three capabilities: production, distribution, and monetization of sports content. They specialize in building custom, digital networks bringing top tier execution capabilities into the mix as well. In a major sports city like Chicago, there’s no denying why they made the list.
WeDeliver: They were recently acquired by Deliv, and they also won our 2013 Chicago Mixer not long before they applied, were accepted, and graduated from Techstars Chicago. The platform is simple, too: you order, you track, and you get a delivery. It doesn’t matter where you order form because the delivery specialists at WeDeliver work for you, the user, first and foremost.
Have a suggestion for a startup not on the list? We’d love to hear your opinion! Feel free to leave a comment below.

When you think about the many different, successful tech ecosystems spread across the US there are a few givens that just can’t be dethroned. You’ve got New York, Silicon Valley, and Washington DC for sure, but I’d also say that you have to include Chicago as well.

If you think otherwise, I’d push you to dig in deeper to the city’s rich culture of startup companies. Not only do they have the quintessential Midwest mindset, they also show strong support for females in tech and offer an incredible amount of resources for entrepreneurs. This celebration of the Chicago ecosystem is brought to you by @properties, the leading Chicago real estate brokerage serving both the city of Chicago and North Shore through dynamic marketing and innovation. Follow the full content series here.

Not to mention, it’s where our own CEO Frank Gruber hails from, so we know it produces some top notch talent. Outside of that though, there’s a whole list of damn good reasons to startup in the Windy City.

Chief among any of these reasons, though, is the amount of local success they’ve produced and maintained since the days of the .com boom. To that end we’ve gone in and uncovered some of the greatest startups in Chicago’s history that have helped put the city on the map and are still kicking today:

  • Basecamp: While the company has their operation spread out across 26 different cities, they’ve maintained their HQ in Chicago since they got their start back in 1999 – 37signals at the time. Over the years they’ve remained committed to helping companies and teams focus on one common goal: finishing a project together. It’s actually something they focused on internally when Jason Fried decided to pivot 37signals’ main effort towards their best product, Basecamp: “We’ve become a bit scattered, a bit diluted. Nobody does their best work when they’re spread too thin. We certainly don’t. We do our best work when we’re all focused on one thing.”
  • Belly: They were founded on the principle of making loyalty rewards easily accessible to all customers and readily available at every business. The Belly team offers different programs that cater to each business’s personality, culture, brand, and objectives in order to foster more personal relationships with their customers. It’s that kind of attitude and attention to detail that landed them in Dell’s Founders Club 50 an elite society with access to exclusive efforts and resources provided by Dell.
  • Edmodo: Although they’re currently operated out of San Mateo, CA, Edmodo started up in Chicago when two school district employees set out to bridge the gap between how students live their lives and how they learn in school. They’re now the number one K-12 social learning network in the world. Back in 2010 they got a round of funding from Union Square Ventures, who summed up their expertise: “Edmodo is based on the premise that teachers need an easy way to share content with their students. Around this central concept, Edmodo has created a social and mobile experience that appears to be resonating well with teachers and students. The team at Edmodo, existing investor Learn Capital, and we are committed to supporting the learning community in schools across the country and the world.”
  • Groupon: Everybody is familiar with Groupon at this point. Further, everybody is more acutely aware of the troubles they encountered while on their startup journey. However, you don’t get to become one of the greatest of all time without your challenges. What separated Groupon from other companies was how they dealt with their shortcomings. In 2014 they made some big announcements about how they plan on owning the market as they recovered and moved forward into the future. They put their heads down to focus on charity, partnerships, merchant services, acquisition, and travel in an effort to shake things up: it definitely worked for them.
  • Grubhub: The nation’s leading online and mobile food ordering company has been long dedicated to connecting hungry diners with local takeout restaurants. In fact, their platforms allow diners to order from around 35,000 restaurants in over 900 US cities and London. They’ve maintained a strong commitment to always putting the needs and wants of their users first and foremost, going so far as to implement an ordering setup in their own office to ensure everything worked properly. We’ve had the pleasure of covering and following GrubHub since their early, early days in Chicago and we’ll follow them for, well, forever.

These next five startups might not be Chicago’s greatest yet, but they’re definitely well on their way to greatness.

  • Charlie: This tool compiles one page summaries on the people you’re about to meet with, before you see them. An hour before every meeting in your calendar, Charlie makes sure you walk in with the intel you need to make a killer impression: breaking news on their company, the passions and hobbies you both had no clue you shared, and stheir professional history.
  • MentorMob: Billed as a crowdsourced learning website, MentorMob consists of a community of enthusiasts who curate online courses from the web’s best content. Everything is organized into comprehensive courses that can teach you everything from entrepreneurship tips to snowboarding. Each course covers beginning, intermediate and expert skill levels, building a full, free online class for you from existing online content.
  • MobileX Labs: It’s their express goal to change the mobile landscape of how artists and companies currently interact with fans and followers. To that end they offer ways to make an iPhone app in five minutes or less. Specifically they have MXL Build, MXL Apps, and MXL Games – curriculums that are all designed to teach users how to build their best apps and games with little to no coding.
  • Silver Chalice: This next-generation digital sports media company owns and operates multiple digital networks as well as a standalone tech division. The founders built their platform on three capabilities: production, distribution, and monetization of sports content. They specialize in building custom, digital networks bringing top tier execution capabilities into the mix as well. In a major sports city like Chicago, there’s no denying why they made the list.
  • WeDeliver: They were recently acquired by Deliv, and they also won our 2013 Chicago Mixer not long before they applied, were accepted, and graduated from Techstars Chicago. The platform is simple, too: you order, you track, and you get a delivery. It doesn’t matter where you order form because the delivery specialists at WeDeliver work for you, the user, first and foremost.

Have a suggestion for a startup not on the list? We’d love to hear your opinion! Feel free to leave a comment below.

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