Tech In Chicago

Ezra Galston is a VC at Chicago Ventures. At CV, Ezra focuses on consumer facing investment and is actively involved with BloomNation, Kapow Events, Luxury Garage Sale, Shiftgig, SpotHero, Zipments, and Havenly. He writes one of my favorite VC blogs at BreakingVC.com and his thoughts on startups have also been published in the Wall Street Journal, TechCrunch, VentureBeat, and Re/code. Before becoming a venture capitalist, Ezra was a professional poker player and the Director of Marketing for CardRunners Gaming.

Listen on itunes listen on stitcher

In This Episode You Will Learn:

• How Ezra got into angel investing?
• What motivates Chicago Ventures?
• What's the one question every founder should ask of their VCs?
• Why Ezra prefers growing a business over starting one?
• Where Ezra sources his investments from?
• Why producing content as a VC is important?
• How they look for outliers in the entrepreneurs they back?
• How Ezra finds and cultivates his mentors? Hint: cold emailing
• Why Ezra thinks e-commerce companies are underestimated?
• What Ezra wishes he knew when he first got into the venture industry?
• Why some venture capital investments never get announced?
• Why Ezra thinks Chicago is so good at building great business?
• What we can do to make Chicago even better for startups?

Favorite Books:

• The Little Prince by Antoine de Saint-Exupéry
• Ayn Rand
• Sweet Pickles by Richard Hefter

• Seeing What Others Don't: The Remarkable Ways We Gain Insights by Gary Klein

E-Commerce Companies:

• Stitch Fix
• Trunk Club
• Wayfair
• Zulily

Investors Ezra Admires:

• Bill Gurely, VC at Benchmark
• Fred Wilson, VC at Union Square Ventures
• Brad Feld, VC at Foundry Group
• Stuart Larkins, VC at Chicago Ventures

Miscellaneous Things Mentioned:

• Taylor Caby, founder of CardRunners
• Chris Fargis, founder of Instant Fantasy Sports
• John Tough, COO at Choose Energy
• Report Says Chicago Has the Highest Percentage of Female Entrepreneurs
• The Little Prince (2015 film)
• The Counterintuitive Thing About Counterintuitive Things by Startup L. Jackson
• Tilt (poker term)
• The Big Short (2015 film)
• Dear Brad, Fred & Mark: How The Hell Do You Do It? by Ezra Galston

Neal Rothschild is the founder of Rooster, a 6-minute daily podcast that updates you on all the news you need to know. Neal just launched Rooster at the beginning of this year and it was great to interview a founder just getting started on a really promising startup. Neal initially came up with the idea while walking back and forth to the school he was teaching at in Romania. Before Rooster, Neal was also a journalist with pieces published in the New York Times and USA Today.

listen on itunes listen on stitcher

In this episode we cover:

• Why he decided audio is the most effective and efficient way to get information?
• How he landed on the name Rooster?
• Why critical feedback is the best feedback?
• What the process is like producing a daily podcast?
• How he stays on top of all the news in the world? Hint: Twitter lists

Neal's Idols in New Media:

• Ira Glass, This American Life
• Alex Blumberg, Gimlet Media
• Bill Simmons, The Ringer
• Deadspin.com
• Gawker.com

Neal's Favorite Books:

• Boomerang: Travels in the New Third World by Michael Lewis
• The Big Short: Inside the Doomsday Machine by Michael Lewis
• The Life and Times of the Thunderbolt Kid: A Memoir by Bill Bryson
• A Short History of Nearly Everything by Bill Bryson
• Game Change: Obama and the Clintons, McCain and Palin, and the Race of a Lifetime by John Heinemann
• A Heartbreaking Work of Staggering Genius by Dave Eggers
• The Goldfinch: A Novel by Donna Tartt

Aaron Dallek is a serial entrepreneur and Co-Founder of Opternative - the world's first online eye exam. The exam can be taken from anywhere, at anytime, and a doctor issued prescription can be used to shop everywhere. The exam only takes 25 minutes and a digital prescription is delivered in 24 hours or less. listen on itunes listen on stitcher In this episode we cover: -How to raise money in the current down market - In February 2016, Opternative closed their Series A ($6 million) from Jump Capital, Chicago Ventures, Pritzker Group, Tribeca Venture Partners, Corazon Capital, and NextGen Partners. -How they built an online eye exam that rivals the traditional phoropter -How to recruit the best talent against larger companies with deeper pockets -Why you have to take things one step at a time as an entrepreneur Aaron's Favorite Book: The Art of the Start 2.0: The Time-Tested, Battle-Hardened Guide for Anyone Starting Anything by Guy Kawasaki

Ryan Coon is the founder of Rentalutions and a former investment banker. Rentalutions provides all-in-one landlord management software. Whether you manage one unit or multiple buildings, Rentalutions gives you the ability to receive electronic rent payments, manage leases, find the right tenants, and deal with maintenance issues. Listen on itunes listen on stitcher In this episode we cover: Making the transition from investment banking to entrepreneurship Starting a company for the right reasons How the Chicago tech scene has changed Finding your first customers Ryan's Favorite Book: The Monk and the Riddle: The Art of Creating a Life While Making a Living by Randy Komisar

Rod Rakic is the founder of OpenAirplane, a plane sharing marketplace. OpenAirplane makes it easy for pilots to find, book, and pay for aircraft rentals online or on their phones. Renting an airplane is now as easy as renting a car. Listen on itunes listen on stitcher In this episode we cover: The benefits of private aviation over commercial travel The secret to avoiding parking fees at airports Why you ask for advice instead of money Making things work as a distributed team Rod's Favorite Book: The Customer Support Handbook: How to Create the Ultimate Customer Experience for Your Brand by Sarah Hatter

David Gardner is the founder and CEO of ColorJar, a Chicago-based creative tech agency. Before founding ColorJar, David was a professional basketball player and a founder of a social network in India. ColorJar specializes in branding and creating custom websites and mobile apps and has worked with everyone from Fortune500 corporations, to venture-funded startups. Listen on iTunes listen on stitcher In this episode we cover: Why he decided to start an agency What makes a great name and brand How to approach building a new brand to cut through all the noise Why user personas are better than talking about demographics How the Chicago tech scene has changed in his 8 years since founding ColorJar The surprising benefits of having a distributed team Why employees and employers should date (contracting) before marrying (full time) Why he prefers to hire freelancers Why you should follow your instincts David's Favorite Book: Blink: The Power of Thinking Without Thinking by Malcom Gladwell