- 37signals – Jason Fried
- A Space Apart
- Abby’s Digital Photography
- Adam Siegel
- Airbnb – Nathan Blecharczyk
- AKA MEDIA INC
- Allie Osmar Siarto
- Amy Hoy
- Annie Sorensen
- Apply in the Sky – Emily Chiu and Chiara Piccinotti
- Awayfind – Jared Goralnick
- BabbaCo – Jessica Kim
- Barcelona Creative Group
- BatchBlue Software – Michelle Riggen-Ransom
- Behance – Scott Belsky
- Big Teeth Productions
- Black Cat Strategy – Beatriz Alemar
- BlogDash – David Spinks
- Bonsai Interactive Marketing – Danny Brown
- Brad Flora
- Braintree – Bryan Johnson
- Brazen Careerist – Ryan Paugh
- Brenden Mulligan – 2009
- Brenden Mulligan – 2010
- Buffer – Joel Gascoigne
- Carol Roth
- Centro – Shawn Riegsecker
- Cheezburger Network – Ben Huh
- Chegg.com – Aayush Phumbhra
- Chicago Art Department
- Chicago Street Musicians
- Chris Bennett
- Cimaglia Productions – Matt Cimaglia
- Cool People Care – Sam Davidson
- CoSupport – Sarah Hatter
- Crosstown Scenic
- crowdSPRING.com – Ross Kimbarovsky & Mike Samson
- Dabble – Jessica Lybeck
- Daily Planet
- David Rothstein Music
- DealsGoRound.com – Kris Peterson
- Disqus – Daniel Ha
- DreamChamps – Jill Felska and Jenn Krenn
- Emerson Spartz
- EnGreet – Adam Weinstein
- ExtraOrdinary Casting
- fathead design
- FeeFighters.com – Sean Harper
- Fifth House Ensemble
- Fig Media
- Firebelly Design – Dawn Hancock
- Firespring – Jay Wilkinson
- Flashpoint Academy
- Flowtown – Dan Martell
- FoiledCupcakes.com – Mari Luangrath 2009
- FoiledCupcakes.com – Mari Luangrath 2010
- FoodieRegistry.com – Ben Reid
- Foursquare – Dennis Crowley
- FusionCharts- Pallav Nadhani
- Garrick Pohl – Zipments
- Gini Dietrich – 2009
- Gini Dietrich – 2010
- Github – Chris Wanstrath
- GiveForward – Desiree Vargas Wrigley
- Grasshopper – David Hauser
- Groupon – Andrew Mason
- GrubHub.com – Mike Evans & Matt Maloney
- Grubwithus – Eddy Lu (2010)
- Grubwithus – Eddy Lu (2011)
- gtrot – Brittany Laughlin
- Hudl – John Wirtz
- Ideal Project Group – Andrew Wicklander
- Imagination Publishing
- IndieCollision.com – Carlo Navarro
- Instant Technology – Rona Borre
- Inventables – Zach Kaplan
- ItStartsWith.Us – Nate St. Pierre
- IwearYourShirt.com – Jason Sadler
- Jonathan Pasky
- Jones
- Jun Loayza
- Kartemquin Films
- KMA Management
- Lakeshore Branding
- Laura Roeder
- Lifesta.com – Eran Davidov
- Little Independent – Lesley Tweedie
- Long Pork
- Manifest Digital
- Mark Lawrence – SpotHero
- Maternal Instinct – Kat Gordon
- MCC Recycling – Michael Mills
- McKinney Chicago
- Melissa Pierce
- Mightybytes
- Mightyvites
- Milk Products Media – Todd Tue
- Mindlight Films
- Motion Post
- MyDadNMe.com
- Natiiv Arts & Media – Leah Jones
- NextStep Test Prep – John Rood
- NogginLabs
- Orange Chair Productions
- Particle Audio
- Paul Singh
- PerkSpot – Christopher Hill
- Phil Tadros
- Photogram – Bob Armour & Brian Hand
- PitchEngine – Jason Kintzler
- Plugola
- POP! Social Media – Jill Felska & Jenn Krenn
- Proxibid.com – Joe Petsick
- Red Frog Events – Joe Reynolds & Ryan Kunkel
- Red Frog Events – Joe Reynolds 2011
- Reddit – Steve Huffman
- Restaurant Intelligence Agency – Ellen Malloy
- Rhythm Cafe
- Rob Matthews – AirRun
- Robomodo
- Roscommon
- Ryan Evans – Bite Size PR
- Sarah Evans – 2009
- Sarah Evans – 2010
- Savor Agency
- Saya Hillman
- Scalewell
- Scriptito.com – Chad Stansbury
- SeatGeek.com – Russell D’Souza
- See3 Communications
- Shane Mac
- Shotfarm – Mike Lapchick
- Sittercity
- SocialKaty – Katy Lynch
- Sole Search – Brandon Williamson & D.J. Grant
- StorageByTheBox.com – Phil Murphy
- Storenvy – Jon Crawford
- StoryStudio Chicago
- StudentOfFortune.com – Sean McCleese
- StyleSeat.com – Melody McCloskey
- SYDCON Web Development – Dave Devitt
- TandemSpring – Tomer Yogev
- Tatango – Derek Johnson
- Teletech Video
- The Big Playoff – Chris Vankula
- The Ocean Agency
- The Printed Blog – Josh Karp 2010
- The Printed Blog – Original 2009 Launch
- TheLocalTourist.com – Theresa Carter
- Threadless – 2009
- Threadless – Jake Nickell 2010
- Total Attorneys – Ed Scanlan
- Towers Post
- Urban Theater
- Visual Website Optimizer – Paras Chopras
- Vitamin
- WeaveThePeople.com – Paul Caswell
- Wedobo.com – Amanda Sudimack
- Wendy Piersall
- Where I’ve Been – Craig Ulliott
- Windy City Social
- WooThemes – Adii Pienaar
- Wufoo – Kevin Hale
- YouTern – Mark Babbitt
- Zaarly – Bo Fishback
- Zacuto
- ZocDoc.com – Cyrus Massoumi
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