Millennial Travel Podcast

Mental Stretch Marks and Confidence Boosts with Daniel DiPiazza of Rich20Something

Matt Wilson
January 16, 2024

Our Guest

Daniel DiPiazza of Rich20Something joins us to talk about doing great work you and how to overcome self doubt.  This is the message you need to level up your confidence.

Daniel has launched several successful businesses which have allowed him to live life on his own terms and do the things that he enjoys.

Over the last few years Daniels has successfully:

Daniel is one of my closest friends, so in this casual conversation we talk about what to do when things get harder in life. 

The Episode

We cover everything from meditation, to using motivation from the death of his grandmother to write his second book, to his use of medical marijuana as a performance enhancer.

After we talk about book suggestions, supplements, workouts and diet in our speed round, Daniel drops some sage advice about being patient and staying bored if you want to create your best work.

We even get to hear Daniel’s story of escaping Atlanta and buying a Benz in Santa Monica.  (Mixtape coming soon!)

For a living, Daniel helps young people bridge the gap between their education to actually marketing those skills.  If you are a graphic designer, writer, yoga teacher, trainer or anything in between, the Rich20Something Community is an awesome place to learn how to actually make money doing those things.

Topics Covered:

  • Papa John's Pizza
  • Intermittent Fasting
  • Writing as a form of meditation
  • Morning routines
  • The health benefits of putting yourself in your natural enviornment
  • How to work on and grow your following authentically
  • Self Doubt
  • The one word you need to keep in mind if you're struggling to figure out your next step


"Thought leadership can now be a career"

"Your following is only a small part of the equation"

"Self doubt will always be there its like a constant companion, but its only a bad thing if it stops action."

"Our generation needs to get more comfortable with the idea of boredom"

"Hustle is great and hustle will get you some things, but patience will help you keep those things"

Listen in Now and begin chipping away at that self-doubt...

You can get this episode directly to your iPhone on iTunes or your Android on Stitcher!

Edited By: Eric Aguirre

Matt Wilson
Matt Wilson is Co-founder of Under30Experiences and Author of The Millennial Travel Guidebook: Escape More, Spend Less, & Make Travel a Priority in Your Life. He is host of the Live Different Podcast, Millennial Travel Podcast, and formerly Co-founder of He is committed to helping people live more adventurous lives.


last minute deals


As Seen In...