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.
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In This Episode You Will Learn:
Favorite Books:
Seeing What Others Don't: The Remarkable Ways We Gain Insights by Gary Klein
E-Commerce Companies:
Investors Ezra Admires:
Miscellaneous Things Mentioned:
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.
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In this episode we cover:
Neal’s Idols in New Media:
Neal’s Favorite Books:
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.
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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
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.
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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
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.
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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
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.
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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