Charlie Gilkey

Charlie Gilkey is the kind of guy you can throw any question at.

What's the difference between a philosopher soldier and a soldier philosopher?

Where did the phrase “what fires together, wires together” come from (and what does it mean)?

How can we get metaphysical and explain the formation of galaxies?

These are the kinds of questions Charlie is ready for and has mind-blowing answers to.

In a way, Charlie's approach, smooth speaking, and being effortlessly persuasive reminds me of Todd Tressider. Todd and I got deep in episode 013 and Charlie swims in the deep end too.

Here's just a taste of the insight Charlie offers up in this Smart and Simple Matters episode:

Experiences are really what we're looking for. Not stuff… Asking yourself, ‘Is this stuff?' means questioning what is serving you. Abundance, contentment, and happiness are tied to experiences and the quiet times you hear yourself talking about what [you] need. – Charlie Gilkey

[Tweet This]

Adding to Charlie's grooviness is his popular public speaking about taking action and the practical steps needed for big change. He has been featured at MSNBC, Seth Godin's Domino Project, The Guardian, and Lifehacker, but he's most often found at his home base,

His latest hit is the Amazon best-seller The Small Business Lifecycle and you'll get to hear him explain how we can apply the principles of business to anything.

Get ready … 'cause here comes Charlie!

In This Episode You'll Learn About:

  • Why most things you want won't get you what you need.
  • How a philosopher becomes a warrior.
  • Why growing up poor can help you become an entrepreneur (not stop you).
  • Different types of abundance … and which ones will let you thrive.
  • Stage 1 of Minimalism: the core metric.
  • Why everyone hates stage 3 of the small business cycle.
  • The look and feel of a campaign against stagnant energy.
  • How to simultaneously curate experiences for yourself and someone else.
  • Why the phrase “what fires together, wires together” is so important.
  • If people are actually more capable than they think they are.

Resources and Items Mentioned in This Episode Include:


  • [09:11] Charlie's seeds of awesomeness
  • [12:27] The philosopher solider
  • [15:34] Simple living and relieving pressure through nature
  • [20:49] How the small business lifecycle helps all facets of your life
  • [29:05] Email Triage
  • [35:02] How Charlie curates his existence
  • [41:13] Switching from connecting to consuming to creating

Awesome Ways to Subscribe to the Show

If you're not already subscribed for automatic notifications of a new show, please do so with one of the links below.


The transcript will not be available until I find a new transcriptionist (if you know someone good, let me know).

I'm Grateful for Your iTunes Reviews!

If you enjoyed this specific episode or the Smart and Simple Matters show in general, I always appreciate when people go to the iTunes page and leave an honest review. Every single review is a huge help and received with gratitude!

If you want to make me incredibly thankful, like the people who have recently left an iTunes review, here are the four quick steps (assuming iTunes is already installed):

  1. Visit the Smart and Simple Matters iTunes page here:
  2. Click the blue button on the left labeled “View in iTunes” below the cover art of the show
  3. When iTunes loads, scroll down below the “Customer Reviews” section and click the link labeled “Write a Review”
  4. Write a review with whatever title you like, whatever length you have time for, and give the show an honest rating. If you don't think it deserves five stars, don't rate it as a five star show.

And if you have someone or something you'd like us to cover on an upcoming show, tell us in the comments below.