#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
SHOW NOTES
Key Topics & Timestamps
[00:00] - Introduction and early career background
First job at Anderson Consulting (now Accenture)
Early lessons about equity and company value
[15:00] - Education and career development
Why he chose Wharton for his MBA
Experience at the Small Business Development Center
The value of practical experience over classroom learning
[30:00] - Building and scaling businesses
Raising initial $450,000 from angel investors
Completing 13 acquisitions in 18 months
Running a 500-person company by age 29
[45:00] - Leadership philosophy and hiring insights
Why humility is the #1 hiring criteria
The importance of interviewing every employee
How focusing on individuals leads to company success
Quotes
"If someone isn't humble, doesn't matter what their talent stack looks like... you won't take in new information." "I focus on the person first and the company second."
Resources Mentioned
Book: "Influence" by Robert Cialdini
Book: "48 Laws of Power" by Robert Greene
Book: "How to Lose at Almost Everything and Still Win Big" by Scott Adams
Key Takeaways
Spend 100 hours per year on any skill to reach the top 5%
Focus on people first, company objectives second
Humility is the most important quality in hiring
Building through service to others leads to success
Choose who you work for over job title or company name
Get In Touch
Connect with Dave on LinkedIn