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 69 Episodes

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...

Marvel What If...?: Why Imagination is Key to Character Development

This time the guys visit the alternate timeline of Marvel's What If...?. In the midst of a series focused on Becoming Curious Explorers (like some of our favorite lea...

Shang-Chi: How Curiosity Leads to Character Development

Curiosity drives character development. Plain and simple. The directions we are curious towards will be the directions our character moves in the long term. Join Der...

Arrested Development: How to Continue Exploring When You Feel Like a Failure

This week's Tour is a character study of everyone's favorite magician GOB Bluth from Arrested Development. GOB seems to fail quite often, yet he always has the persis...

Elf Pt. 2: How to Be Inspiringly Curious

Buddy the Elf shows us all how to be curious in any environment. Each of us could ask ourselves the question: how might I be more curious given my life experiences an...

Elf Pt. 1: Why Be Curious When It's Safer Not To

In this week's Christmas themed episode the guys put themselves in the shoes of Buddy the Elf, examine why we would choose to be curious when it generally requires tha...

Loki: How to Take On the Mindset of an Explorer

(Loki S1 E1) To kickstart the series on Becoming Curious Explorers Derrick and Drew travel with Loki to visit the Time Variance Authority. Much like Loki, we are ofte...

Interstellar: How to Pass On Your Work at the End of a Chapter

As leaders, we all want our work to live beyond us so we must be effective at passing it on to the next generation. In the bridge episode between the Game Theory seri...

Ready Player One Pt. 2: When to Adjust Our Strategy and Tactics

The guys go deep into Halladay's character and approach to mentoring, seeking to understand how we do like the great founders we look up to, can "pass on" our greatest...

Ready Player One Pt. 1: How to Run at Your Own Pace When the Game Seems Too Fast

It can feel hard to keep up with the pace of change in today's climate. Thanks to the virtual world of the Oasis in the year 2045, the game moves at an even faster sp...

Anchorman: How to Prepare for (Inevitable) Confrontations

Off on another rabbit hole, the guys take a crack at the infamous Anchorman fight scene. As humans, we all run across conflicts from time to time. Some seem avoidabl...

Hunger Games Pt. 2: Creating Alternate Win Conditions

Continuing the Hunger Games Tour with Danny, the guys ponder how Katniss is able to use her empathy to create an alternative win condition for the game. While it ofte...

Hunger Games Pt. 1: Mixed Strategy Games

Another week another Wonder Tour first. Derrick and Drew are joined by our first ever special guest, our friend Danny. Danny brings his outstanding passion for peopl...

Return of the Jedi: When to Enter the Game

Introducing a new type of WonderTour, a rabbit hole. If we truly believe at not all who wonder are lost, then it follows that even by going down a side road in the jo...

The Office Pt. 2: Games within a Game and Buttlicker Challenges

The guys take a lot of joy in analyzing one of the funniest scenes in all of the Office, Jim's portrayal of the crusty customer, William M. Buttlicker (Season 5, Ep 7)...

The Office Pt. 1: Zero Sum Games and Prince Family Paper

The guys break down The Office season 5 episode "Prince Family Paper". The focus of the show is the Zero Sum game where there is a clear winner and loser. How do we ...

Fellowship of the Ring Pt. 2: How to Win with the Weaker Hand

The guys discuss games with incomplete or hidden information by looking at how Saruman and the Fellowship's strategies differ in the war for Middle-Earth. They then u...

Fellowship of the Ring Pt. 1: Game Theory

The first Wonder Tour of Lord of the Rings is a milestone. Derrick and Drew celebrate by looking up to one of the most cherished mentors in any media, Gandalf. What...

Doctor Strange Pt. 2: Strategically Breaking the Game

The guys begin by unpacking the wise last words of the Ancient One, "Arrogance and fear still keep you from learning the greatest lesson of all: it's not about you". ...

Doctor Strange Pt. 1: Developing a Growth Mindset

The guys enter another dimension as they analyze how Doctor Strange grows from being a selfish leader to a servant leader. When someone, like Stephen, is stuck in a f...

Inception Pt. 2: Moving on from Unfinished Endings

In the second part of the Tour of Inception the guys unpack the ending, debating if the top is still spinning and what it all means. Alikening our shared journeys to ...

Inception Pt. 1: How to Tear Down our Projections and Let the Truth Have It's Day

The Wonderers begin by wrestling with the way shared dreaming works and what rules and formulas might apply in the movie. They focus on Saito to learn about the spons...

Parks and Rec: Does the End Justify the KABOOM!?

This week's Tour focuses on Parks and Recreation Season 2 Episode 6 (Kaboom). Keef (Paul Scheer) inspires Leslie to KABOOM her pit problem. Along the way Derrick and...

Guardians of the Galaxy: Turning Up the Vibrancy Levels on Life

In one of the guys favorite episodes yet, they weave together elements of music, visuals, themes, and story coming to the conclusion that living life vibrantly is a ke...

Fight Club: Renovating our Over-Structured Lives (and Businesses)

For this Tour the guys attempt to navigate the dream-like arc of Tyler Durdin, Jack, Marla, and Bob. The narrator, Jack, is a great example of how an over-structured ...

Rey Skywalker: How to Lose Phantom Weight

As leaders, we tend to carry extra weight that isn't really ours to wield. Weight that's projected onto us from our past, from our present, from our colleagues, from ...

Batman Begins: The Purpose of Leadership

This week we are throwing back to the first recorded episode of Wonder Tour that we never aired. The guys discuss mentor theory and then work through how we might dig...

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