Welcome aboard to episode 2 of the Uncovering The Aviation Mindset podcast.

Today, I am joined by my friend Grady Montgomery, a full-time US-based Gulfstream contractor, entrepreneur, ex-firefighter, and self-confessed dreamer.  

Grady and I met over ten years ago on the Gulfstream 650 type rating course in Savannah, USA, and have been great friends since. 

Grady inspires me as he has always had the confidence to go it alone and not rely on employment to make his living.  He is also a successful businessman, running his property and t-shirt retailing businesses. 

In his spare time he enjoys spending time with his daughter, flying his light aricraft, and motoring around on his boat.  

In this conversation, Grady and I discuss his journey in aviation, starting from his late entry into flying and progressing to becoming a Gulfstream pilot. 

We explore topics such as taking risks, overcoming the fear of failure, dealing with challenging situations, teamwork, decision-making, leadership, and supporting others. 

Grady emphasises the importance of confidence, believing in oneself, and empowering others. 

He also highlights the role of mentors and the responsibility to help the next generation of pilots.

Takeaways

• Taking risks and investing in one's passion can lead to fulfilling careers.


• Overcoming fear of failure is essential for personal and professional growth.


• Teamwork and effective decision-making are crucial in aviation.


• Leadership involves empowering others and supporting their growth.


• Mentoring and helping the next generation is a responsibility for experienced professionals.

Chapters

00:00 Introduction and Background

02:23 Starting Flying and Career Progression

06:05 Taking Risks and Investing in the Future

10:25 Overcoming Fear of Failure

13:19 Dealing with Challenging Situations

17:34 Teamwork and Decision-Making

25:10 Gaining Confidence and Empowering Others

29:59 Saying No and Making Difficult Decisions

38:49 Leadership and Supporting Others

42:35 Mentoring and Helping the Next Generation

• If you are interested in exploring how to develop your mindset and confidence with me, why not click the link to my website and book a FREE 30-minute discovery call during which we will discuss whether I am able to support you with my coaching program?


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Transcript

Ben le Fleming (00:00 .322)

think that's right we all have our intrinsic fears actually one of my fears is heights I've got a real fear of heights so we can because that's quite an interesting one you know I know for a pilot and I know other pilots that are afraid of heights too so I always find that just a little ironic but it is what it is yeah I'm here I'm here today with my lovely friend Grady and I've known each other for about 10 years we did our Goldstream 650 course together

month in July, we both got some experience on the 550. We made friends immediately, went out, socialized together and just really became great friends. And we've seen each other all around the world now for nearly 10 years. So welcome Grady. Thank you, Ben. Pleasure to be here. Thanks for having me on your podcast. Lovely to have you. Grady's got a really interesting background because he didn't actually start flying until he was 34. And you came, as you...

Talked about, as I well know, we've talked plenty of times about as you came from not a privileged family in terms of finances. So you've had to work all through your life and you went through and did the business and finance degree, set up a t-shirt business, worked really as an entrepreneur. You didn't start flying until 34. That's all correct, Ben. You know, being a pilot had been a childhood dream.

So, you know, I wanted to do it, just didn't have the financial resources to pursue it through college, out of college. You know, I started a different company, a t-shirt company. And before that, you know, I had done various jobs. I was a DJ, a lifeguard, a bartender, just a lot of different things. And the t-shirt company provided the financial wherewithal to get my pilot's license. And I'm pretty much a goal already in person. So I decided, well, I know nothing about flying. I know nothing about aviation. So.

I'm going to stick with until I solo. And if I don't like it, then I'll drop out then. But I actually loved it. And I went on and got my private pilot's license and then just kept moving forward. Like everybody else, Instrument Commercial, ATP, started a little aerial tour company, which I turned into a 135 charter, which led into me becoming a co-pilot on a Citation II that was based on the local field where I lived and did my flying. And that's kind of how I got into aviation.

Ben le Fleming (02:23 .246)

Yes, that's such a brilliant story. But I can't actually remember, I've asked you this specifically. When you got into flying, did you do it to become a commercial pilot or was it just literally to get to that first stage of sailing and seeing what happens after that? It was, there was no goal to become a commercial pilot. It was strictly to get a private pilot's license. Like I mentioned, my goal was to solo. And then once I reached that, then I wanted to get my private pilot's license. And you know, what...

I did it for multiple reasons. I've always had a travel bug. I've always liked to travel and I've always had a sense of adventure. And, you know, weekend trips, when you have a small airplane, take on a whole new meaning because three and a half hours in an airplane can take you a lot further than three and a half hours in an automobile. So, that's how I got into it. And then, like I said, it was my passion. So, even though I was later in life, I just kept pursuing it. And, you know, this brought me to where I am today. Yeah, such a good story. The thing that I...

I'm really impressed about we talked about this back in 2014 because I've got that sort of basic mindset. What I think I'm pushing through it now about the idea, well, let's stick with the safety thing and get a job so that you've got a guaranteed income and you've got a bit of a pension and things like that. But you went against that grain. I know being an entrepreneur, you have that mindset and I think I'm very much developing that in my later years now. Very it's wonderful. It's very liberating, very empowering. But you.

You did that early, because you've been a contractor. We call it freelance over here. But you've been a freelancer for the last 14 years. And to go from... I mean, you had your first job, I think, on citations and Falcons, but to actually go and decide... That's just such a good story, the way you went from chief pilot on the citations to the Falcons to the next stage of becoming a Gulfstream pilot. I mean, I love that. It's such an impact. Tell us that story.

Sure. Well, it's not a great story, but it's, I was chief pilot for a great part 91 flight department. And, you know, the financial downturn, they got behind it. They couldn't get ahead of it. So that department closed. And I was just starting, trying to figure out what I wanted to do. This is in 2009, 2010. And, you know, the aviation market wasn't great. So I was looking at everything. I was doing contract work in the Citations and the XL.

Ben le Fleming (04:43 .094)

And I'm going like, if I want to do this, you've got to go large cabin. You got to go global or Gulf Stream. And I've lived near Savannah. I have friends at Gulf Stream. I have other acquaintances that flew Gulf Stream. So I chose to do that route. So I did, I paid for my own 550 type, my G5 type, which was a 550 to 450 of the G5. And it took me a couple of years to become successful at that because

You know, it's like any other business. When you've got to go out and you market yourself, you've got to go to the event, you've got to let everybody know who you are and what you're doing and that you're available. And you just got to meet and greet people. So I was a, it took me a couple years, but I turned into a successful G5 contract pilot. The G650 was announced and I told a buddy of mine that like, oh, that's, I'm going to school on that. And he kind of chuckled and said, okay, yeah, sure. And when it came out,

I was in one of the earlier classes with you on the 650. And, you know, I paid for all my own training. So I had paid for my G5 initial. I paid for all my recurrence. And I bought and paid for my G650 type. And, you know, it's a leap o