In this episode of the Winning at Business and Life podcast, host Professor Pete Alexander interviews Gregory Kassim Rutledge, a PayPal UX designer who also works as a confidence coach and motivational speaker. Rutledge shares why he enjoys uncovering user frustration in design, likening coaching to serving vegetables with different seasonings. He emphasizes that company culture originates from the CEO’s values and urges leaders to model the behavior they expect. He advises business leaders to address imposter syndrome early, reframe anxiety as excitement, and improve communication, claiming it can boost perceived value by up to 50%. Rutledge introduces two acronyms for managing fear—FEAR (Fictional Evidence Appearing Real) and FACE (If Anything scares you, Face it). He names several peers and mentors he’d like to see on the podcast, including his business coach James Hilliard and various community leaders. Discussing his first job as a fry cook at McDonald’s, he highlights the fast‑paced environment as a character‑building experience valuable for corporate life. Finally, he provides his social‑media handles and platforms where listeners can find his coaching content.
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This is Professor Pete Alexander with the Winning at Business and Life podcast, where business leaders share their insights. It is 6 questions in 7 minutes because successful business leaders are busy and rarely have more time to spare. So let's get to it. Question number 1: In a few sentences, please tell me who you are and what you do.
All right. Thank you for that question, Pete Alexander. I am Gregory Kassim Rutledge. I am a UX designer for PayPal by day, and I am a confidence coach and motivational speaker by night. I take people from confused to confident in 90 days without the need for outside validation.
Ooh, I really like that, Gregory. It's a pleasure to have you on the show. Question number 2: What is something that makes you smile and/or laugh about working in your industry?
In the design industry, it's that we're on the other side of the apps where people get frustrated, finding out why people are frustrated and how to eliminate that frustration. It's funny because on the other side of it, you get to kind of laugh at the other side of the the mirror, you know, stand the other side of the black mirror where you're like, oh, okay, I get it now. I understand why things operate the way they do. A good little chuckle in the coaching industry. I think the funniest part is that we're feeding people vegetables. Everyone is feeding people vegetables in the coaching industry. It's just what brand and what seasoning that you, that you put on those vegetables in order for people to eat them.
Oh, go ahead.
No, sorry. And the meat that you put with it, of course.
Mm-hmm. Well, and I like that. That's a great analogy, the vegetables, because, you know, they're healthy for you, but there's different ways to serve them up and spice them up, I suppose. So that's a great way to look at it. Question number 3. I have a fictitious book with all the answers for business. What chapter would you think most companies should read?
The chapter where the culture trickles from the top down. So 9 times out of 10, if there is a culture problem, if there's a problem with a company, it starts with the CEO. It starts with the, the values that that CEO lives by and the way that it is interweaved into that company and trickles from the top down. So there's that quote, be the change you want to see in the world, and treat people— treat your people the way you want them to treat your people. It's basically the golden rule, right? But I think that it's, it's missed that there's this disconnect between the owner of the company or the CEO or that, that person that has established this business and the business itself or what it stands for or where it's going. And I would really encourage people to look at that chapter in the book.
I really think that is so insightful because it really is true. Anyone can want to feel a little bit appreciated and treated well. And it doesn't take a lot for a CEO of a company to acknowledge somebody be one of the people down the organizational chart that's doing a, you know, a great job, and it would mean the world to them. But so often that's forgotten, and I really think that your insight is wonderful on that.
Thank you.
Question number 4: Other than the generic work harder, have a great attitude, and care for customers, what advice would you give to other business leaders?
I would say to deal with the imposter syndrome before it becomes the place that you lead from. So we skip over mindfulness so many times, and this just kind of ties into the last question. If we're aware of who we are, what we want, where we're going, why we're doing something, if we have those principles in stone. And we— it just helps build that confidence so that we're not leading from insecurity or a place of fear. We're leading from a place of trust. And this is why I do what I do. This is why I have the trust that I do, because these principles are the guidelines that I follow in my life and my business. And the other thing I will say is learn to communicate. It's proven that learning how to speak and articulate your decisions or your— just learning to articulate in general can increase your value by 50%. Yeah.
No, no, I was just going to say, you know, the 50%, I mean, I think you're— it's probably higher than that. I think that's a conservative number, you know, because if you think about all the different ways that one can communicate with others, if you can really effectively do that and do that confidently because you don't have that imposter syndrome, as you mentioned, I think that that can make a huge difference. Am I right?
Absolutely.
Mm-hmm. Mm-hmm. Yes.
Oh, go ahead. We feel like an imposter because we haven't done it before, and we feel like, who are we to do what we're doing? The only way to cure it— because essentially it's that, that energy is the same imposter energy, anxiety, nervousness, fear— it's all the same energy. But when we relabel it as excitement, or we just take the action, right? It changes that energy to something that can be used rather than something that hinders and holds back. So just the action cures anxiety. If I just do it and I keep doing it, the law of averages will eventually take over there, and I'll find myself doing better at and learning, even though I don't realize I'm learning. I'm still learning. As I go.
I really like that too. And, you know, it's that taking that action. And I like to also think of fear as a 4-letter acronym: Fictional Evidence Appearing Real. And, you know, we so often are fearful about something that may or may not happen, and it lets us get into this stuck state instead of a state of action, as you're suggesting. So I think that that's really insightful.
I love that you used an acronym. My acronym is actually empowering. I know that one, actually. That's false events appearing real was, was the one I heard. But then there's face everything and rise. Here's a prompt to face everything that— and, and I've taken the 'if anything scares you' or 'do one thing every day that scares you.' Eleanor Roosevelt, that quote really inspired me. I turned it to a personal motto that is if Anything scares you, face it head on so that nothing stands in your way. Once you battle those fears, I mean, it's like taking a cold shower in the morning, that priming exercise. Once I've done that, nothing else is going to be as hard as that was in that day.
So very, very true and very insightful. And thank you for teaching me a couple different of those acronyms. I like that. Question number 5: What other business leader like yourself yourself would you like to acknowledge and invite to be on my podcast?
So I have a few people in mind. First one that comes to mind is my business coach, uh, James Hilliard. He has been an integral part of my last 6 months, actually almost a year now. But I remember him from when I was barista at a software company. I got moved up and just, it just started my journey. But I remember him stopping one day and saying, what are you doing? Because I had created such an experience at the Starbucks and I'd brought all these employees together that had never seen each other to congregate at this bar and just created an atmosphere. And he's like, you're wasting your time. So that jump-started. But then fast forward 3 years, he's now my business coach. I've started my own thing. I've moved up, no longer in the service industry. So he was an integral part in that. And my life coach, Jessica Cosine. Then there's other people that have been integral parts of my journey, but they're all comfortable on camera. They're all very business-minded, dynamic leaders. So there's Everett Swain. Nandi Manning, Tracee Lovejoy, Shannon Lucas, Lee Andrees, and Lauren Greif. I probably— I don't know if it's Greif or Greif, but they have all done so much in the communities that they serve and for me and everyone I've seen them interact with. And I just think that giving them that 7 minutes would be Amazing.
Well, thank you for that, and I appreciate all those, uh, those people, and I'll look forward to connecting with them. And our final question, question number 6: please tell me about your first job.
My first job was McDonald's. I was the fry guy, and you wouldn't think that you would learn much from working at McDonald's, but I think that was the best place to get a foundation because you learn that for pennies— I think I was making $5.15 when I started— you have to do so much so fast, and you have to be able to read people on the spot to match their energy, to make their experience right. You have to make sure that you keep up with the fries because lot of people come through and get McDonald's fries. So we went through pounds and pounds and tons of fries every week. And although I only did it on the weekends, it really strengthened my character and, and was a perfect start. If I could get— if I could recommend to anyone where you should start in your career journey, it would be at a fast food restaurant because that's going to be that character building exercise that intestinal fortitude that you need to be able to survive once you get to the corporate world and be able to communicate well with people, think on your feet.
Mm-hmm. You know, and it's funny that you say that because I know a lot of people who've had that as their first job as well, and they say very similar things because you just have to move. You just gotta have, you know, do as quickly as you can because it's all about efficiencies. And I think it's important that, as you said, that the experience that the customer is having, because, you know, McDonald's is the perfect example of the— you walk into their location and the person expects a certain experience. So, you know, they have to live up to that. And so it's, it's really insightful and a great story because I can totally appreciate that. And I'm sure a lot of our listeners are going to as well.
Thank you, Pete. It's been a joy being on this show. I know we planned this back in, I want to say, January or last year, so it's been a long time coming.
It has, but it's been worth it. We finally got it to happen. And Gregory, I absolutely appreciate you being on the show. How can people find you?
Uh, so I run my Facebook page like my landing page for like my website, so All the coaching stuff is on Facebook. You can find me under my full name, Gregory Kassim Rutledge. On YouTube, it's Gwiz Insane is the channel. I am on TikTok, Question Everything LLC, and Instagram, I believe, is Gwiz Inquisitive. I was trying to have some kind of parity between it all, but you know, people steal my name and I just— there will be a rebrand at some point that we're working on that. But yeah, those are the places you can find me. And then of course here on LinkedIn, I've become sort of the LinkedIn guy in my field. That, well, at least that's what they used to know me as. Now they know who I am, but it started as, hey, you're the LinkedIn guy. So here on LinkedIn, I'm under my full name as well.
Perfect. This is Professor Pete Alexander with the Winning at Business and Life podcast. Thanks for listening.
