In this concise 7‑minute interview, Professor Pete Alexander talks with Terry Dry, founder of Future Proof Advisors, about his career and business philosophy. Dry describes himself as an advisor‑entrepreneur who helps mid‑market companies overcome growth barriers, emphasizing his passion for enabling others. He shares what makes him smile—seeing people grow and laughing at his own past mistakes to teach others. When asked which chapter of a hypothetical business book is most essential, he highlights the mindset chapter, distinguishing a "play‑to‑win" versus a "play‑not‑to‑lose" attitude as the foundation for leadership success. Dry’s core advice for leaders is to be resourceful: seek existing solutions, partnerships, or freelancers rather than reinventing the wheel, leveraging the internet and tools like Zoom to act quickly in a fast‑changing environment. He recommends fellow entrepreneur Steve Schwartz of The Art of Tea as a compelling podcast guest. Finally, Dry recounts his first job at a Chicago record store, noting how retail and service experiences taught discipline, customer interaction, and curiosity about systems—lessons he now applies in advising agencies, e‑commerce, and service businesses. Contact information is provided via futureproofadvisors.com and LinkedIn.
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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.
I'm Terry Dry. I'm an ad— an advisor and an entrepreneur. Which really just means I've founded, grown, and kind of reinvented companies for the last 25 years. And now I'm at this point in my career where I've been successful, and I just get so much passion and drive from helping others be successful. So that's why I'm the founder of Future Proof Advisors, which is where we help mid-market businesses on essentially how to transcend barriers inhibiting growth so as to essentially achieve much bigger and better outcomes. Because ultimately, that's me. I want to create a better future for people and for business.
Well, Terry, it's an absolute 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?
Yeah, it's funny. I think what makes me smile is really helping people. And maybe that sounds a little sappy, but it's helping people grow and make breakthroughs, and it just makes me so gratified. And then I would actually tell you, on the side, What makes people laugh is when I share my own experiences in business, essentially where I screwed up in the past and where I've made mistakes so I can help them not make a mistake. So not only do I laugh, but they laugh too.
I love that. And it's great when you can laugh at yourself because, you know, it just makes you more real and approachable. So I love that.
Yeah, I have those moments where I'm like, okay, that's why that happened 10 years ago is so that I could help this person not screw that up now. Now I get why I went through that trauma. That's a great way to look at it.
I love it. Question number 3: I have a fictitious book with all the answers for business. What chapter would you think most companies should read?
To me, it would be the chapter— whatever chapter is about mindset. And really what that means is, do you have a play-to-win mindset, or do you have a play-not-to-lose? Because in business more than anything else. It's all about the mindset of the— essentially the leader and their energy. And to me, that's always the biggest area of focus. But sometimes people just skip that and move right into the thing they're doing.
I love that, and it's so true because, you know, if you have the wrong mindset, you're just going to create unnecessary obstacles, stress, whatever you can think of. And so if you have that right mindset, boy, you're going to be sailing through all the challenges that come your way, I would imagine. Is that your experience?
Totally true and so hard to do, right? Like any entrepreneur, you've got self-doubt, you've got anxiety, you've got team, you've got a lot of stuff going on in your head. So it's not always easy, but if you stay focused on mindset in general and you're aware of it, like there's just so much you can gain.
Absolutely. Question number 4: Other than the generic work harder, have a great attitude, and care for customers, what What advice or insight would you give to other business leaders?
It's kind of my mantra always, which is be resourceful. And I kind of use this little statement, which is the right answer is out there somewhere and your job is to go find it. And there's so many people who I think in business will focus on, I gotta solve this problem, I'm gonna solve this problem, rather than stepping back and going, am I trying to solve a problem that's already been solved? And if so, be resourceful and figure out what that is. Is it a partnership? Is it a person? Is it something, a freelancer that will help you? And just being really resourceful, especially today, because the internet is an amazing thing and Zoom is an amazing thing. And there's so many different ways now where you can be really resourceful.
It's very true. And, you know, I love the point that you make about, are you trying to solve a problem that's already been solved? I mean, why, you know, for using an overword, worked recreating the wheel. I mean, why, why try and do something difficult like solving something that you can just go and you can find, as you say, a resource or a tool, etc.? It's very, very, very important to remember that time is such a valuable asset that we have. And if we waste that time on— by not taking advantage of something that could be very cost-effective for us, it's nuts. Would you agree?
Completely agree. And there's so many times where people are trying to do things that, like, someone else can do this better. So why wouldn't you give that to your customer or give that to your business? Why on earth would you try to recreate it when it's already there? And now it's about, to your point, speed. And also the rate of change is greater than ever before. So if you're not able to be resourceful, adaptable, agile you're kind of— you're archaic in a sense. You've got to move forward, and being resourceful is the easiest way to do it. And I do that in life too, every which way you can. If you can find people or things that can help you get further along and play to your strengths and play to someone else's, that's a win.
Yeah, I would agree with you 100%. Thank you for that. Question number 5: What other business leader like yourself would you like to acknowledge and invite to be on my podcast?
Well, I thought about this. There's a great, great friend of mine, and he leads a company called The Art of Tea, which, if you haven't ever heard of it, I recommend it. It's just the most high-end, fantastic tea. And his name is Steve Schwartz, and he's mission-based. It's a terrific story behind it, fantastic product, and he's just this entrepreneur with this growing, fantastic business. And I think he'd be great for what this is as far as the combo of winning at business and life. He, he's a great one for that.
Wow, thank you for that. It sounds really like a great person to interview, so I appreciate that referral. And our final question, question number 6: please tell me about your first job.
My first job is in a kind of, um, store that doesn't exist anymore, which is a record store. I always wanted to be in music business. I loved music, and I worked in a big record store in Chicago where I grew up I loved it. And it's funny what I learned, which like, I was in the retail business obviously, and I was also in the service business because I was on the floor helping people, asking questions. And fast forward, those are the businesses that I work with today as an advisor, is agency business, service business, retail, e-com, and how that's changed. And it's kind of funny when I think back that it formed that, but I learned so much, everything from like being on time, being disciplined, to just regular ins and outs of business, people, how things really work, even like the CD music business. And even, I'll never forget, there was a Ticketmaster computer back there. And whenever it was slow, I would sit there and just play around with the computer and learn how interesting that system was and how it worked. And so it was a great experience for me, but that was my first job now in a, in an industry or area that doesn't even exist anymore.
It is really true because as you were describing it, I was thinking of Tower Records, you know, and they're no longer around. And I actually, one of my first jobs as well was a huge chain, Radio Shack, that really is no longer around anymore either. It's just the way it is. But it's a great story. And I appreciate you sharing it with us. And I really appreciate you for being on the show. So how can people find you?
You can find me at our website at futureproofadvisors.com. You can find me on LinkedIn, or you can always just me an email. I think your links, uh, you're linking me to that, so you don't want me to spell anything out, but feel free to reach out if I can be helpful. Perfect.
This is Professor Pete Alexander with the Winning at Business and Life podcast. Get hundreds of amazing business insights from previous guest episodes on your favorite podcast app. Thanks for listening.
