Jim Downs, CEO of Chicago-based custom trading software company Connamara Systems, has had a fascinating career path. Once an avionics engineer, an Intercontinental Ballistic Missiles (ICBM) telemetry expert with the CIA, and market maker at the CBOT and CBOE, he founded Connamara in 1998. On today’s episode, he shares some of the lessons he has learned along the way about operating and scaling his bootstrapped company, such as adding the missing “gears” of sales and marketing to the “machine” and a SHIFT of mindset from working IN the business to working ON it. His motto is now “If your business depends on you, you don’t own a business; you have a job. And it’s the worst job in the world because you’re working for a lunatic.”

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