G104: Mike Ragsdale

Riding the Dot-Com Wave, Getting Paid to Play & Life in a Simulation with Mike Ragsdale

I’m back from my sabbatical and I couldn’t be more excited for this first guest of the year. But I’d first like to thank all of the incredible Gravity guest hosts who took over the show while I was away. Their variance in experience and perspective only grows what we’ve established here and I’m appreciative of those contributions. 

In this edition, we’re sitting down with Mike Ragsdale, Founder and CEO of 30A, a Florida travel guide that has transformed into a full blown lifestyle brand shaped around the American beach way of living. 

Our conversation begins with Mike’s childhood upbringing where he was pushed to become a high achiever before falling into a successful career as a marketer working in advertising. Mike stumbled upon an AOL disc in the early ‘90s and the rest was history. He was instrumental in the creation of one of the world’s first humor websites, building a highly successful online community in the process and creating a highly successful company in the process. 

Sadly, as we know, The Dot-Com Bubble didn’t last and Mike pursued other ventures and interests. Eventually, he realized that there were things in life more important to him than money, and following his bliss inadvertently led to the creation of 30A – now a wildly popular brand in its own right. 

We discuss everything from what he’s learned along his remarkable life journey, to the ever-evolving perception of video games in society and culture, to whether or not we exist in reality or if we’re just living a simulation. This is exactly what Gravity is all about. It’s great to be back.

What Brett asks:

  • [01:47] Let’s start at the beginning: tell me about your upbringing.
  • [12:25] Were you interested in gaming as a kid and how did that affect your childhood?
  • [15:44] Tell us about the awakening you had.
  • [23:03] Tell us how you got into marketing.
  • [36:02] How did your experience with AOL unfold?
  • [44:59] What caused you to step down as CEO and found a new venture in 30A?
  • [52:21] How are you building community with 30A?
  • [59:46] What role do you think community will play in Web3?
  • [1:08:51] Any final thoughts?

Lessons for intentional living:

  • Mike considers himself to be a lazy person – yet he’s one of the hardest working people out there. He says that he loves the mental work he engages with so much that it powers him up rather than it draining him. There’s a real lesson here about the importance of pursuing your passions, even if it comes at the expense of things like material wealth. As Mike says, where he’s from, success is measured in how much spare time you have to sit on the beach and enjoy life.
  • On a similar note, we should make sure that we don’t lose sight of what our passions actually are. Mike did just that when one of his companies became so successful that he was suddenly in a management position instead of on the ground, doing the work he enjoyed and that had made the company successful in the first place.