Taking the Leap

Drayton Wade is a millennial entrepreneur, start-up veteran, Clemson grad, Knoxville Fellow, and graduate of London School of Economics. As one of the youngest delegates at the Christian Economic Forum, Drayton has worked at multiple start-ups and is currently working at a start-up in the area of technology and automation at UiPath. Drayton joins Bob in this podcast to talk about his unique passions and how they helped him pivot in his atypical career path from his college studies that started out in engineering to his post-grad days working for start-up companies in AI and automation. Together, they banter back and forth on sales, education, technology, and books.

Show Notes

"If work is going to be that consuming and that integratable into life, it better be something you’re interested in. I keep making these pivots because of A.) self-awareness and B). what I am interested in. If I’m going to put in lots of hours, I want to be interested in it. [So I ask myself,] is it something I’m interested in? Is it something that leads to more opportunities?" -- Drayton Wade 


Drayton Wade (@draytonwade) is a millennial entrepreneur, start-up veteran, Clemson grad, Knoxville Fellow, and graduate of London School of Economics. As one of the youngest delegates at the Christian Economic Forum, Drayton has worked at multiple start-ups and is currently working at a start-up in the area of technology and automation at UiPath. His passions include counterterrorism, economics, automation, artificial intelligence, nonprofit work, and sales.


Drayton joins Bob in this podcast to talk about his unique passions and how they helped him pivot in his atypical career path from his college studies that started out in engineering to his post-grad days working for start-up companies in AI and automation. Together, they banter back and forth over what sales really is, the differences between American education and British education, and the many remarks people make about millennial career men and women. Not to mention, they discuss countless books they’re reading, how they implement education into their life, and the mentors that have authority to speak into their lives. 


Quotes from this episode:


-“People with backgrounds that are atypical can leverage that in sales because they have a good EQ. They have a good understanding of how to communicate precisely and concisely. [At the London School of Economics,] they wanted to know how you thought, how you could structure an argument, and how you could communicate. That’s sales in a nutshell.”


-“We aren’t rational creatures. With sales, it’s the same way. It’s all about the relationship. It’s about understanding the person, it’s about getting to know the person on the other side.”


-“The atypical path has helped me. I don’t know any better. I don’t have this rigid path I have to follow. I jumped around, and I pursued whatever there was.” 


-“I’ve changed jobs almost every 2 years. It’s often viewed as a negative [for millennials]. It’s total crap to me. Think about the expectation you’re setting on them. You’re expecting them to be self-aware enough to know their interests and gifts God has given them [for their lives at the young age of 18 - 22].”


-“If work is going to be that consuming and that integrable into life, it better be something you’re interested in.”


-“I keep making these pivots because of A.) self-awareness and B). what I am interested in. If I’m going to put in lots of hours, I want to be interested in it.”


-“Too little options cause unhappiness and too many options cause unhappiness.” 


-“[With a mentor], there has to be the freedom to just straight up tell you, ‘You’re wrong.’ That’s really valuable in a spouse and in a mentor. Otherwise, you don’t really have a mentor. I’m giving you authority over my life to tell me no or to tell me I’m wrong.” 


-“Every day is running up the score. Every day, [I ask myself] what meaning can I derive from this particular day.” 


-“If you truly believe what you say you believe, it doesn’t matter. You’ve already won. I’ve gotten more than I deserve to begin with, so I’m just running up the score.”
 

Links in this episode include: 


The Knoxville Fellows, a branch of the Fellows initiative in Knoxville, TN 


The Fellows Initiative, a network of Christian Fellows programs all over the US 


Thinking, Fast and Slow, a book by Daniel Kahneman on Amazon


Force multiplication, a military term to multiply power to have greater effects than without it


Napoleon Hill, a Wikipedia article on his life and work as an author 


MOOCs, these are massive open online courses available to all via the web that are free


Khan Academy and Coursera, both are online learning platforms where you can find lots of courses on various subjects


New Way MBA, an online learning community designed to help entrepreneurs fill the gaps in their education


Wine MOOCs, a list of MOOCs that feature wine specific courses 


AI Superpowers, a book by Kai-Fu Lee on Amazon


Harvard Business School Case Study Method, this is the education method Harvard Business School uses that isn’t based on memorization but experience


London School of Economics and Political Science


Bottom Line Upfront, this is a business principle about saying the conclusion of the argument first 


The Fifth Discipline, a book by Peter Senge 


Cuban Missile Crisis, a brief synopsis on this situation from JFK’s presidency


Groupthink, a psychological phenomenon on the mindset a group takes on


Virtual reality, a brief overview of what virtual reality is


Oculus, the virtual reality (VR) equipment and technology Facebook acquired 


Apple AR glasses, a brief article on the release, price, and specs of these augmented reality glasses 


Augmented reality, a brief overview of what augmented reality is


Microsoft Hololens, mixed reality technology Microsoft developed


Metaverse, the collective space we live in, including both virtual and physical reality 


Principles for Success, a book by Ray Dalio


Saudi, Inc, a book by Ellen Wald


The Messy Middle, a book by Scott Belsky


Dichotomy of Leadership, a book by Jocko Willink and Leif Babin


Loonshots, a book by Safi Bahcall


Blitzscaling, a book by Reid Hoffman


What You Do Is Who You Are, a book by Ben Horowitz 


The Hard Thing About Hard Things, a book by Ben Horowitz 


Hacks on Tap, a podcast on Luminary with Mike Murphy and David Axelrod


Jocko Podcast, a podcast on leadership and discipline 


The Tim Ferriss Show, a podcast by Tim Ferriss 


Slowburn, a podcast by Slate Magazine 


Dan Carlan’s Hardcore History podcast


To learn more about Bob’s two books, find them on Amazon here: The Leap and Love Your Work.

Follow Bob Dickie on Twitter @RobertDickie

Creators & Guests

Host
Robert Dickie
CEO, Author, Entrepreneur, Investor
Designer
Tristin Dickie
Nashville Fellows Program 2022, Marketing Assistant for Affinity Technology Partners, Professional Photographer freelancer. Go VOLS!

What is Taking the Leap?

Taking the Leap Podcast hosted by Robert Dickie III discusses changes in our global economy impacting the way we work and live. For young professionals starting their careers, mid-career professionals navigating changes and late-career professionals thinking about starting an encore career, Robert and his guests discuss the global economy, technology, workplace developments, and all the latest changes impacting our professional lives.