Running Two Companies, Mastering Sales, and Building Without Fear
David G. Ewing shares hard-won wisdom from surviving the dot-com nuclear winter to running two companies simultaneously, a consulting firm and a software startup.
David answers the opening question: does entrepreneurship age you prematurely or keep you young? He explains how it felt like the weight of the world in his 20s, but now in his 40s, he feels younger.
David shares the story of starting his first company after a colossal startup failure, during the ".com nuclear winter" when no one would invest—not even his own father.
A mentor gave David some blunt, unforgettable advice early in his career: To succeed as a CEO, you need to either learn how to make things or learn how to sell them.
David reveals that the most effective sales technique he ever learned wasn't about talking, but about listening. He explains the concept of "Socratic selling"—asking the best questions to lead a customer to their own conclusion.
How do you scale a company beyond $100 million? David breaks down the three fundamental levers of growth: get more customers, increase their basket size, or get them to buy more often.
David shares one of his hardest-won lessons: As the CEO, no one on your team will ever give you the hard truth because you hold the power to fire them. He describes being called a "happy knight with a super sharp sword," and the importance of self-mastery.
Getting the first customer is almost as hard as getting the next ten. David compares it to being the first patient of a brain surgeon and shares his strategy for "launch marketing" to get the first 20 customers at once.
On his 40th birthday, a mentor shared a shocking lesson: The human mind is a completely emotional tool. We make all our decisions emotionally and then justify them with logic after the fact, a key insight for sales and marketing.
David tells the story of learning to hold his breath for 4.5 minutes with coaching from a world-record freediver. The key takeaway was a lesson in leadership: when you eliminate fear, people can achieve things they never thought possible.
After being elected president of the Austin chapter of the Entrepreneurs' Organization, David attended a conference for all the new presidents. When the trainer asked who felt like they didn't belong there, almost every hand in the room went up.
David explains how his new software company, Content Lion, was born. When Oracle decided to exit a product line, it left 2,500 customers stranded. Seeing no good alternatives on the market, David's team decided to build one themselves.
Costa and David discuss the trend of AI dramatically reducing the time and cost of writing software. They explore whether this commoditizes software development or simply shifts the value proposition from raw cost to time-to-market.
David recalls a talk by futurist Ray Kurzweil, who predicted that the technological progress of the entire 20th century would be matched in just the first 25 years of the 21st. David reflects on how that seemingly outlandish prediction has largely come true and what it implies for the next seven years.
What's the ultimate test for powerful AI? Costa and David humorously conclude that by 2035, AI should be able to generate a proper, satisfying ending for Season 8 of Game of Thrones, using the original actors at the correct age.
David shares a personal story about coaching his son's high school drone robotics team, which placed second in the nation. Now that his son is in college, they're starting their next project together: competing in the "ant weight" division of BattleBots.
