Derrick Cobb

Derrick Cobb

Derrick Cobb comes from a digital transformation background. He enjoys solving problems by using a computer like a swiss army knife. With his Enneagram type 4 ("the Individualist") Derrick brings a deep empathy and emotional unpack to the Wonder Tour so that lessons can be understood for everyone to benefit.

Appears in 65 Episodes

The Dark Knight Rises Pt. 1: How To Climb Out of a Deep Pit

At points in each of our lives we have our own dark nights where we feel trapped in the proverbial pit without the ability to escape. In The Dark Knight Rises, each o...

The Force Awakens Pt. 2: How to Follow the Invisible Map

As we transition into a new series called "Hope and Belief" we return to a beloved franchise and character to guide our learning. When we first find Rey she is capabl...

The Force Awakens Pt. 1: Why Do We Run Away But Hide the Map So We Can Still Be Found??

Whether its a stagnant job or a repetitive personal life, we can find ourselves lacking joy and hope, trapped in a closed loop without meaningful disruptions. Like Ja...

Stranger Things Pt. 2: How to Have Compassion On Those Above and Below You

It's hard enough to have Compassion on our peers but how do we have Compassion on those above us and below us in the organization chart? All too often we hear blaming ...

Stranger Things Pt. 1: How to Have Compassion on Someone We Don't Agree With

We would all probably say that we want to be compassionate people. But what do you do when you don't agree with the person you are trying to have compassion on? In St...

Obi-Wan Pt. 2: How to Make the Small Pains of Life Meaningful

Energy management is one of the most challenging parts of being a functioning member of the world, much less a magnanimous leader.  When the weight of the world feels ...

Obi-Wan Pt. 1: When is Compassion a Liability?

While our world might not seem as dark as a galaxy under the veil of the evil empire, like Obi-Wan Kenobi closing himself off from the force it can sometimes feel like...

Thor Ragnarok Pt. 2: How to be the Leader the People Need (Instead of the Leader You Want)

In the MCU oftentimes what we remember most about our favorite heroes is their overcoming moment or how they vanquished the bad guy in the final fight. Yet, in our da...

Thor Ragnarok Pt. 1: How to Find the Balance Between Compassion and Wisdom

Choosing to act compassionately can feel like it drains our energy levels. On top of that the world is full of people in need and our time and resources our finite so...

Wisdom, Money, and Stories Pt. 2: Is There a Limit to How Fast We Can Develop Character?

With humans like with money it just seems like it can't grow fast enough. We want our investments to compound sooner. We want the hard work we are putting into our c...

Wisdom, Money, and Stories Pt. 1

In our first Bonus episode, Derrick and Drew go on The Cash Podcast with host Adam Koos. If you resonate with WonderTour but are wondering how we go about applying wh...

The Batman Pt. 2: How to Inspire Hope When All Seems Lost

As humans, it seems like hope is a currency that we are always short on. As leaders we seek to inspire hope in those around us, but without a formula to execute, it's...

The Batman Pt. 1: Why Subverting Expectations Changes Everything

Normally it's considered a negative to subvert expectations. When it comes to compassion, if we wish to see lives transformed then we must look for opportunities to u...

Parks and Recreation: Why Compassion is Essential

As we begin episode 1 of a series on compassion, we return to Parks and Recreation (S2E19) to check out everyone's favorite lovable goofball Jerry. It's so easy to fi...

Top 10 Moments of Wonder: How to Become Magnanimous

Why can't we be like the magnanimous leaders from our favorite movies, extending ourselves for the good of others? Over the first 50 episodes of WonderTour we've journ...

Parks and Rec: Integrity is Worth the Cost

One of the main reasons we might examine ourselves and find we don't measure up to the integrity of the ideal leader is because integrity seemingly must come at a cost...

The Prestige Pt. 2: Why Integrity is Worth Founding Your Life On

Integrity is a foundational building block for a leader. A cornerstone that all other character traits are built upon. Much like a magnanimous leader, the film The Pr...

The Prestige Pt. 1: How to Prevent Character Deterioration

Continuing our series on integrity we examine the lives of two rival magicians Alfred Borden and Robert Angier as they each seek to become the world's greatest. Over ...

Boba Fett: How to Transform Without Losing Who You Are

In life we often feel the stress of conforming to established structures like organization charts and governments. While these things are great for sustaining order t...

Don't Look Up Pt. 2: How to Share Unpopular Truth

Like Dr. Mindy and Kate, it sometimes feels like we are swimming upstream to deliver a message of critical importance. "We need to transform our business model!" "Yo...

Don't Look Up Pt. 1: How to Stay Intact in the Face of Existential Threat

It's so easy to compartmentalize ourselves into a work self vs a personal self. Psychology shows that if we aren't careful we can end up flipping a switch in our brai...

Dune Pt. 2: Character is Destiny

In today's world, it almost seems impossible to maintain integrity in all we do. To consistently take the long view, making decisions that prioritize the good of othe...

Dune Pt. 1: How to Achieve Team Goals By Acting With Integrity

This week's Tour brings a new guest, but a veteran of living out the Wonder Tour, Brian. As leaders it can be a struggle to get everyone rowing in the same direction....

Encanto Pt. 2: How to Lead with Integrity When the Magic Seems to be Fading

Integrity has the power to hold everything together in our lives but it also has a power to set us free. Mirabel's superpower of integrity fixes the cracks in her fam...

Encanto Pt. 1: How Integrity Allows Us to Win in the Long Run

As we begin a new series on integrity, it's nice to start with a working definition. On Wonder Tour, we define integrity as acting consistently for the good of others...

Treasure Planet: How Curiosity Changes the Character of Others

As a finale to our series on curiosity, we take off on a whimsical air ship with James Newton Howard playing in the background to learn how our curiosity impacts the c...

The Matrix Pt. 2: Breaking Out of the Cultural Matrix for the Good of Others

If you've seen The Matrix you might have found yourself wondering if your life might infact be some grand simulation. Derrick and Drew flip that question by asking ho...

The Matrix Pt. 1: What If We Aren't the Protagonists?

This time our Tour leads us to the Matrix as we continue our series on Becoming Curious Explorers. Often, when we are searching for our role in the stories playing ou...

Marvel What If...?: How to Avoid Succumbing to the Dark Side of Curiosity

This time on Marvel's What If...?, what can we learn from Doctor Strange's unyielding pursuit to raise Christine from the dead? In this exciting, yet haunting episode...

OutRoar Digital Experience, LLC.