220: STOP Ignoring These 7 Leadership Mistakes That Can Kill Your Startup | Ken Gavranovic

What separates good leaders from truly transformative ones? In this powerful full-episode conversation, Damon welcomes Ken Gavranovic—seasoned tech executive, Thinkers50 honoree, and serial builder of billion-dollar businesses—to The Learn-It-All Podcast for a no-holds-barred exploration of leadership, entrepreneurship, and the future of work in the AI era. Ken unpacks his unique path from humble beginnings to leading 18 exits and owning $3B in P&L, revealing how the world’s best leaders don’t just excel individually—they elevate everyone around them. From the lessons hidden inside failed startups to why AI is redefining the playing field, this episode is overflowing with hard-won wisdom, tools, and real talk for leaders who want to level up themselves and their teams. 

Packed with actionable advice, personal stories, and candid reflections, this episode is your blueprint for becoming not just a high performer, but a meta performer—one who inspires, coaches, and wins with others. Whether you’re scaling a startup, transforming a legacy business, or aspiring to lead with more impact, you’ll leave fired up and equipped to turn learning into lasting results. 

In this episode, you’ll learn: 

• What it means to be a “meta performer”—and how great leaders elevate entire teams, not just themselves 
• How Ken went from scrappy founder to building a $200M company from the ground up 
• The critical difference between measuring outcomes vs. activity (and how to actually set targets that drive results) 
• Why money alone won’t make you happy—and what true success and options look like as a leader 
• How to ask better questions, foster a culture of feedback, and avoid becoming a bottleneck as you scale 
• What AI means for every business: why it’s a massive equalizer, and how to find quick wins (without making million-dollar mistakes) 
• The career-defining lessons you’ll learn at a failed startup (that big companies can’t teach you) 

Timestamps: 

00:00 – How “meta performers” level up those around them 

00:33 – Welcome to the Learn-It-All Podcast: About Ken and what’s ahead 

01:43 – Ken’s first questions when starting something new 

02:19 – The childhood experiences that shaped Ken’s entrepreneurial drive 

05:33 – Money, happiness, and the real options of wealth 

07:44 – What mentors look for: Grit, honesty, and taking care of others’ capital 

08:25 – Building Web.com from scratch: The inside story 

11:33 – Mistakes of the dot-com era (and lessons for AI today) 

14:51 – Why neither “experience” nor youth guarantee right answers 

17:13 – Outcomes vs. activity: How busywork derails companies 

18:08 – Measuring results at New Relic: Asking the right questions 

21:16 – How to coach with questions instead of answers 

22:35 – Moving from high performer to meta performer (and why it matters) 

25:18 – Elevating your team: From leadership to “teamship” 

27:23 – Is it the product or the people? How Ken evaluates startups and investments 

31:37 – AI’s disruptive power, past and future: What’s next for leaders 

35:02 – AI, jobs, and the future of work 

40:19 – How to start leveraging AI today (without melting down your org) 

43:24 – The power of prompt engineering for every professional 

46:49 – The future of leadership—and why vision still sets winners apart 

48:18 – The best career risk advice for aspiring founders 

50:18 – The one thing you need with data to run your business well 

51:13 – Where to connect with Ken and closing thoughts 

About Ken Gavranovic 

Ken Gavranovic is a renowned technology...