Smart and Simple MattersMy timing was awesome for a change.

After months of coordinating details for a Smart and Simple Matters (SASM) episode with one of our Simple Sages – Scott Dinsmore – we got to chat shortly after Scott starts blowing up the Internet.

It's not just his recent How to Connect with Anyone course/community launch or his powerful TEDx Talk on How to Find and Do Work You Love. He's on Zen Habits, Smart Passive Income, and just about everywhere else I look.

I've been following Scott's journey at Live Your Legend for three years and I see why he's taking off like a rocket. The clarity and impact behind his message resonates because of statements from our SASM episode like these:

Doing work you love, doing work that is you…is a right. – Scott Dinsmore


I believe the purpose of most of us trying to help people is to inspire possibility. – Scott Dinsmore

I've been fortunate to have other Simple Sages like Pat Flynn, Courtney Carver, and Colin Wright on the show. Adding Scott to the lineup fills me with gratitude and his words are going to help a ton of folks.

Scott and I have much in common like our shared passion for the power of “why,” building amazing relationships, and doing the impossible. But we have different approaches to a number of things.

For example, Scott has investors outsource responsibility to him for growing their money while I empower others to insource their investments through Start Investing with $100. Both are principled positions with the same goal, yet we help people meet a need in very different ways.

With that said, I can't wait for you to listen to these 45 minutes of awesomeness. Like the other Simple Sages on SASM so far, there was much more I wanted to cover. But I'm super proud of the value we generated in the time we had.

Just make sure you check out the resources from this episode I link to below. There's a ton of great stuff waiting to be discovered, so please click a link or two after listening. If you want my curated list of Scott's greatest Internet hits as well, let me know in the comments.

As I say in the intro to the show, get ready for some serious fireworks baby!

What You'll Learn

What will you learn in this one? Geez, where do I start? I'll give it a shot though.

In this episode you'll learn about:

  • Scott's definition of success and how it leads to remarkable relationships.
  • Why you want to “brainwash the impossible” (and how you do it).
  • What event in Scott's life was the ultimate 80/20 return on investment.
  • How much bigger your “why” can be than your “how” and “what.”
  • What Warren Buffett knows a ton about besides investing.
  • The formative event that sent Scott down the path to success.
  • What relationship step out of twenty being connected via social media is.
  • How to build a habit of “controlling what you can control.”
  • What's in the Passionate Work Framework (and why you want it).
  • Reciprocal inspiration and how it starts.
  • Why field learning is more powerful than classroom learning.

Resources and Items Mentioned in This Episode Include:


  • [04:52] What's shaped Scott since his college days
  • [11:49] What success with relationships means
  • [16:34] Insightful investing commentary and Scott's role at Cumbre Capital Partners
  • [21:11] Weighting the role of “why,” “how,” and “what” at Live Your Legend
  • [27:50] Scott's partner charity impossible2Possible
  • [34:40] A vivid verbal recap of Scott's TEDx experience
  • [37:49] The Mt. Everest of physical challenges

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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.