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The landscape of technology and venture capital has changed significantly over the years, and Gary sat down at Transparency ’19 to drop some brutally honest insights about it.

Gary says that “this is the greatest era for fake entrepreneurship,” and that most people are not starting companies to run an actual business but rather as a financial arbitrage machine. In other words, entrepreneurs are starting companies to sell in the future, instead of turning a profit in the present.


The tech company host, FreightWaves, asked Gary about his thoughts on his hiring strategy, culture and business, and the following:

1:07 – Why Gary opened an office in Chattanooga, TN

5:06 – Why Gary didn’t start a VC firm

13:48 – Gary’s thoughts on 8th place trophies

37:28 – B2B businesses need to act like media companies

45:23 – How to adapt to the changing rules of marketing

51:46 – The difference between a salesperson and a marketer

Check out the full vid here: