No Thanks, Forbes. The ACTUAL Hottest Chicago Startups

Look, I’m a huge fan of Forbes. I read Term Sheet religiously. I have friends who work there as journalists. And I think their April 2015 issue feature articles about Benchmark Capital and Chris Sacca are two of the most intriguing VC profiles I’ve read in a while. Flat out they are killing it.

But their take on Chicago’s “Hottest Startups” can at best be described as, well, laughable?



And from ChicagoInno’s Will & Jim:

While they certainly got some things right, the inclusion of two public companies, Grubhub & Groupon is obviously a miss. It’s not 1999 where you could IPO off a biz plan and some wireframes (I once put $2k into eFax when I was a teen, oops!!). Those companies are 9 years old now. That’s not a startup. And the inclusion of GoHealth? It’s a hell of a biz, but it was founded in 2001. I was 16. 14 year old companies are not startups. I think what much of the media often conflates is the difference between “startup” and “tech company.” Protein Bar is much more of a startup than GoHealth…

So with all that said, here’s my list of Chicago’s Eight Hottest Actual Startups (in no particular order):

  1. – Is the fastest growing marketplace for buying/selling unused giftcards. What makes special is their mobile focus, enabling consumers to purchase a discounted gift card, on-demand, at a Point of Sale kiosk, to immediately save money on a purchase (above and beyond regular coupons). In the past 24 months, has raised $81M in VC funding and now boasts 125 employees.
  2. AvantCredit – The fastest growing full-stack digital lender of consumer loans, Avant was started by Enova Financial (CashnetUSA) founder Al Goldstein. With over $500M in equity and another $500M in debt raised over the past 24 months, the company is now valued above $1 billion.
  3. – Super secretive Uptake was founded less than 18 months ago but has made a significant mark on the Chicago scene, hiring over 100 employees in six months and consuming the bulk of Brad Keywell’s time. Fortune has the only deep scoop to date, revealing among other things that they have a deep partnership with Caterpillar.
  4. Shiftgig – The early leader in people marketplaces for temp or hourly workers, Shiftgig had a tremendous 2014 growing 10x year over year, while its member base eclipsed the 1M verified profiles mark. With a recent $10M announced Series A and over 100 Chicago based employees, the company expects to keep growing into 2015. **Chicago Ventures is an investor in Shiftgig.
  5. Civis Analytics – Founded by former Obama for America techie Dan Wagner and funded by Google Chairman Eric Schmidt, Civis is “building a data driven world.” Although mostly secretive about both their clients and products, they acknowledge working with Boeing, Discovery and the American Red Cross are known to build deep analytics platforms to service both enterprises and non-profits to better understand their customers, strategy and spending.
  6. Signal – Founded in 2009 with well heeled technologists Mike Sands, Mark Kiven and Eric Lunt at the helm, Signal (fka BrightTag) has raised over $50M in VC financing while scaling past 150 employees. Its suite of products enabled brands and agencies to track the offline to online conversion path of customers as well as glean advanced analytics from digital tag management. It may not be sexy but its consistent with strong institutional and corporate investors.
  7. Keeper Security – Despite being entirely under the radar, Keeper is consistently amongst the top grossing apps on iOS month after month for its password manager and digital vault. Having now eclipsed 50 employees (according to LinkedIn), Keeper looks to become the next great bootstrapped Chicago story.
  8. Kapow Events – Barely three years old and already the leading platform for curated corporate events booking, Kapow has made big moves including adding Grubhub co-founder Mike Evans to its board (according to LinkedIn). Despite having started 2014 active only in Chicago, Kapow now services 8 cities with Houston, Philly & DC also listed as Coming Soon. **Chicago Ventures is an investor in Shiftgig.

Close Calls: Mu Sigma (11 years old), kCura (15 years old…sorry half my age is not a startup), ContextMedia (9 years old), TrunkClub (acquired, although still effectively a startup), Sprout Social, SingleHop (9 years old).

Have a suggestion for what I missed? Post it in the comments and I’ll make some changes if people think I’m wrong.

Till next time,



About the author

Ezra Galston
Ezra Galston

Consumer focused hustling @Chicago Ventures, Young Entrepreneur @Foundation Capital, Class 18 @Kauffman Fellow, and Chicago Booth MBA. Former professional poker player, with 4 years experience doing marketing/biz dev in the online gaming industry. Launched a "poker hedge fund" in 2011, a record label in College, and produced a festival screened short film in 2006.

  • Samuel Nissim

    First of all, love the blog, and I think you’re quite handsome.

    I’ll throw a plug in for the startup I joined about a month ago: Spotlite. They do benefits enrollment in the cloud (not unlike Zenefits although targeted at slightly larger companies that customize and self-insure). We were acquired last fall by Rally Health, which does wellness gamification, and we’re in the process of integrating the two.

    • egalston

      Good to hear from you, man! Yea, we were the first investor in Spotlite…shhhh! 🙂 Great company!

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