#105 David Guttman: Leading Your Career With Humility

In a candid conversation from his Miami office, veteran tech executive Dave shared insights from his journey from IT consultant to running companies with thousands of employees. A former wrestler and Division I athlete, Dave's path has been anything but conventional - from managing a help desk at 24 to leading multiple successful exits and navigating the volatile crypto space. Known for interviewing every single employee when he joins a company (whether it's 20 or 100 people), his philosophy centers on humility and service to others. "If someone isn't humble, doesn't matter what their talent stack looks like," he says about his top hiring criteria. After raising millions in capital, managing over a dozen acquisitions, and developing innovative business models that disrupted established players, Dave's most profound insight might surprise you: success isn't about being the smartest person in the room, but about being the most willing to learn from others. His advice to spend 100 hours a year mastering new skills (just 18 minutes daily) offers a practical roadmap for continuous improvement in an era often characterized by quick fixes and instant gratification. Here's what you'll learn from this interview with Dave: How a veteran tech executive approaches hiring - why humility trumps talent and experience, and his unique strategy of interviewing every single employee when joining a company A practical framework for skill development: the "100-hour rule" that explains how spending just 18 minutes daily on any skill can put you in the top 5% of practitioners Why focusing on individual employees first (rather than company objectives) counter-intuitively leads to better business results, and how to implement this "servant leadership" approach Inside stories about raising capital and scaling companies - including how investors often act like "sheep" and why it's sometimes harder to raise $500K than $5M A contrarian view on career development - why "do what you love" is bad advice, and how to instead build a career by systematically stacking skills and choosing the right mentors -- email questions to omaid@omaid.me