220: STOP Ignoring These 7 Leadership Mistakes That Can Kill Your Startup | Ken Gavranovic
Release Date:
September 25, 2025
Release Date: Sept 25
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.\
What 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)
In This Episode:
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 executive, global keynote speaker, and a member of Thinkers50. He built Web.com from scratch to $200 million in revenue and has led 18 successful exits, overseeing $3 billion in P&L. Ken’s leadership at companies like New Relic and Cox Automotive have helped scale products and organizations to global prominence. Known for his passion for elevating teams and building winning cultures, Ken is also an active advisor, investor, and advocate for data-driven, people-first leadership.
