Taking the Leap

About 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.

Publisher

Robert Dickie III

Category

business · business

Language

en

Explicit

No

First episode

2 Oct 2019

Latest episode

24 Jan 2026

Latest episodes

66 episodes in the feed.

1. 

   24 Jan 2026

   Todd Wilcox - Assistant Secretary of State - Bureau of Diplomatic Security

   This episode with my friend and HBS classmate Todd Wilcox was recorded before Todd was nominated for his current role as Assistant Secretary of State, Bureau of Diplomatic Security. We speak about his background and views on business and the world. Todd Wilcox was sworn in as Assistant Secretary of State for Diplomatic Security (DS) on October 14, 2025. In this role, he leads the security and law enforcement arm of the U.S. Department of State, ensuring a safe environment for U.S. foreign policy operations. He oversees a global team of Special Agents, Diplomatic Couriers, Security Engineering Officers, Security Technical Specialists, contractors, and administrative personnel. Mr. Wilcox brings decades of leadership experience as a decorated combat veteran, former CIA case officer, and successful entrepreneur. Before joining the State Department, he founded Patriot Defense in 2005, a company dedicated to supporting those who defend America. He served as its Chief Executive Officer for 10 years before transitioning to Executive Chairman, where he guided the company’s vision and acquisition strategy. Prior to his business career, Mr. Wilcox served as an Arabic-speaking CIA Field Operations Officer focused on Middle East and counterterrorism issues. His final assignment was as the CIA Liaison Officer to the FBI’s Joint Terrorism Task Force in Orlando. He joined the CIA in 1997 after serving in the U.S. Army, where he earned the Green Beret as a Special Forces A-Team commander and completed a combat tour during Operation Desert Storm. Mr. Wilcox’s achievements have been recognized by the U.S. Army ROTC Hall of Fame, Ernst & Young’s Entrepreneur of the Year award, and the Orlando Business Journal’s Veterans of Influence Award. He has served on the boards of the National Defense University Foundation, RAND Corporation’s Center for Middle East Public Policy, and the Orlando Economic Partnership. An active member of the Young Professionals Organization (YPO), Mr. Wilcox also serves as Treasurer of Business Force, a nonprofit political action committee.

2. 

   22 Jun 2024

   The Wright Formula: Building and Leading a World-Class Hospitality Business

   Our guest today is Larry Wright Jr., the CEO and President of Wright Investments. His multi-generational family business represents over 200 hotels and 26,000 hotel rooms in 28 states. They specialize in hospitality investments, hospitality management, and hotel and real estate capital projects. Larry graduated from the University of Tennessee with a degree in Hotel and Restaurant Administration. He then earned his Master's Degree at NYU and graduated from the Harvard Business School OPM program. Larry is a member of the Young Presidents Organization (YPO) and an avid outdoorsman. I am excited to learn more from Larry about the hospitality industry, the story of how his father got started, what Larry learned leading his company through the COVID shutdowns that radically impacted his business, and how he inspired confidence in his staff during challenging times. I also have questions on how he navigates today's difficult political climate while serving customers, why continued learning is important to him and his career development, and what books have impacted him most. This will be a fascinating discussion, so let’s jump right in.

3. 

   15 Jun 2024

   Leading in Challenging Times - Christine Assouad, CEO of Dunkin Lebanon

   Our guest today is Christine Assouad, the CEO of Dunkin Donuts Lebanon and Semson Lebanese Cuisine. She has been successfully growing and leading restaurant brands in the Middle East for over 27 years. She is a board member of Food and Beverage companies in the Middle East and provides business workshops at conferences in in the UAE, Saudi Arabia, Kuwait, and Lebanon. Her work also includes business development, franchising, and acquisitions across the MENA markets. Christine is passionate about supporting female entrepreneurship through the “Empowering Tribe” community, where she helps provide online classes, bootcamps, and one-on-one CEO coaching to empower female entrepreneurs to achieve their full potential. Christine earned her Bachelor of Science in Nutrition and Dietetics from the American University of Beirut. She received a Master of Science in Food Science from McGill University and a Master of Marketing from the ESA Business School. She is also a graduate of the Harvard Business School President’s Program and a member of the Young Presidents Organization, also known as YPO. I am really excited to learn more from Christine about her journey leading various businesses, overcoming obstacles in her career, reinventing herself at 47, mentoring next-generation leaders, and her passion for spreading a little happiness and joy in all she does. I know you will be motivated and inspired to hear her story, so let's jump in.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

59 ratings

Spotify

5.0 / 5

18 ratings

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Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.