From Fighter Pilot to Business Maverick with Waldo Waldman (Ep. 39)

The parallels between the skies and the business arena are striking. Both demand a tenacious spirit, unwavering commitment, and a relentless pursuit of victory. Just as fighter pilots can never predict how they will respond in the heat of battle, entrepreneurs face similar uncertainty in their quest for success. However, the key lies in approaching every challenge with the same level of seriousness, dedication to rigorous training, and meticulous preparation. 

In this episode, Brett talks with Waldo Waldman, hall of fame keynote speaker, executive leadership coach, and New York Times bestselling author. Helping leaders & teams adapt to massive change and grow collaborative cultures of courage, resilience, and mutual support, Waldo speaks about how he places a high value on preparedness and authenticity, how joy brings purpose in life, and why you should never fly solo.

Known as "The Wingman," Waldo is an Air Force Academy graduate, MBA, combat decorated Air Force F-16 fighter pilot turned sales manager, performance consultant, executive coach, and motivational keynote speaker. An expert on change management, peak performance & resilience, Waldo works with entrepreneurs, sales teams, managers & executives to help them break performance barriers, overcome obstacles & build cultures of collaboration, courage, and trust. His philosophy — No fighter pilot flies solo, and neither should you. Whether achieving victory as a fighter pilot or in business, the same qualities that ensure success apply: relentless commitment, disciplined training, dedicated teamwork, and servant leadership. But most of all, trust.

Enjoy!

In This Episode

01:52 - Backstory of Waldo Waldman

09:08 - Waldo's take on veterans having head trash

16:01 - How Waldo places a high value on preparedness

18:47 - Steve's thoughts on the power of authenticity in sales

21:38 - What Waldo has to say about success

28:36 - What Waldo means when he says the pain that keeps you awake at night must be aligned with joy

37:40 - How joy brings purpose in life

40:29 - Reasons why you may not want to fly solo

45:47 - What the Check Six in the military is and how it applies to businesses

53:47 - Waldo's final thoughts

Favorite Quotes

10:13 - "You never know how you will respond in battle, but if you take it just as seriously in your training and preparation, the stakes may not be as high. Your life may not be on the line, but your lifestyle is. Especially as an entrepreneur, it's the life and death of your business, future, and dreams." - Waldo Waldman

11:58 - "Those soft skills we learn in the military will allow us to fly combat missions against those veterans or the celebrity brands who are out there trying to squash your business, commoditize you, and impact your lifestyle." - Waldo Waldman

25:57 -"You can't just have a positive attitude. Know your tools. Know your technologies. Find out how to make it more authentic in your business. Humanize it, and then leverage your technologies, the digitization, and all those things that we have to make it easy for the prospect to say yes to you or your client to continue to say yes to you." - Waldo Waldman

31:03 - "It's not what keeps us up at night that matters. It's what gets us out of bed. What keeps us up at night is fear-based. It's debilitating. It distracts us. It holds us back. What gets us out of bed is joy. It builds courage." - Waldo Waldman

47:23 - "As an entrepreneur, especially as a veteran where it was about teamwork and trusting your wingman to do their job, get your ego out of the way, and then continuously get coached." - Waldo Waldman<