#10 Pivoting, Grinding, Disrupting: Lessons from a Successful Entrepreneur with Raymond Lee


Matthew Levy’s Summon Courage, Change Everything podcast examines courage – what it is, what it isn’t, how to summon it – in our lives and work.  

Join Matt and his guests for insightful personal stories about success and useful advice on how to overcome fears, failures and limiting beliefs to pursue a bold vision.

Each episode is a guaranteed dose of inspiration, motivation and practical advice to help you achieve big goals in life and work.


We are excited to have Raymond Lee with us this week.

Raymond is the founder and CEO of Careerminds, executive coach and a speaker. His company is a provider of affordable, effective and efficient solutions for organizations that are downsizing. 

Raymond holds a master’s degree in I/O Psychology from Louisiana Tech University and brings over 18 years of human resource leadership, career consulting, and outplacement experience to Careerminds. 

He started the company in 2008 with one goal in mind: to create an outplacement program that was forward thinking and to reduce the stress employees face during career transition. 

Questions asked and answered in the podcast:

How did your upbringing ultimately influence your career direction?

What made you choose the career in Human Resources?

As a mentor, do you recommend pursuing a graduate degree to others?

What was your first job after getting a master’s degree?

How did your HR career unfold and what was the defining moment when you decided to start your own company?

What kind of mindset does it take to move halfway across the country, and what challenges you have to overcome?

When things got tough, were there moments when you were thinking of pulling the plug and going back to your home state?

What was the incubation period of the entrepreneurial spirit before you took the leap of faith?

How did you wrap your head around giving up the safety of a regular paycheck job?

How do you see Devotion (DREAM Action Plan), sense of purpose playing out in your career?

How do you balance all of the responsibilities of running a business, being a family man and having other leadership roles?

What books do you recommend?

What is one quote that you might want to put on a billboard?

What was the best piece of advice your parents gave you?

What advice would you give to your 21-year old self?

What are other ideas that you might want to share with the audience?


Podcast show notes:

1:10  Introduction.

2:34  How Raymond’s upbringing shaped his entrepreneurial spirit.

04:27  Why Raymond became a psychologist.

6:19  Why having a graduate degree is advantageous.

7:56  The funny disadvantage of having a master’s degree.

10:30  Raymond’s corporate career journey, from humble beginnings to bigger roles.

13:15  The mindset it takes to move halfway across the country.

15:49  The “Keep Moving Forward” mindset and how it helped Raymond to persevere through career challenges.

17:46  When prosperity evaporates overnight, it’s time to pivot. From recruiting to outplacement.

23:00  When you know that you’ve done everything you could at your current position, it’s time to summon courage and change.

25:55  Don’t put an expiration date on your ideas; and reinvent your business if you must. Careerminds.com’s journey as a startup.

33:08  Bootstrap, grind your way and get support. Raymond’s silent partner and further success in capital raising.

37:55  The purpose comes from the search of fulfillment (DREAM framework).

42:12  How discipline and going virtual helped Raymond to create a work-life balance (DREAM framework).

48:08  The innovation of Evergreen Retirement solution and how it was developed to serve the unique social-emotional needs of retirement lifestyle.

54:31  What books Raymond recommends.

56:17  The one quote that he would put on a billboard.

57:02  The best piece of advice Raymond’s parents gave him.

58:28  What advice he would give to his 21-year old self.

59:37  How to get in touch with Raymond and Careerminds.


You can contact Raymond at:






The Art of the Start: The Time-Tested, Battle-Hardened Guide for Anyone Starting Anything by Guy Kawasaki

The 4 Disciplines of Execution: Achieving Your Wildly Important Goals by Sean Covey et al.



Enjoy this podcast? Here are four more things you might like:

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