Episode 30: Future-Proofing with Terry Dry

Episode #30

Mike O'Neill: Welcome back to the Get Unstuck & On Target Podcast. I'm Mike O'Neill with Bench Builders and we're speaking with thought leaders to uncover tips to help you break down the barriers that may be keeping you or your business stuck. Joining me today from LA is Terry Dry. Terry is the founder of Future Proof Advisors.

His team specializes in advising mid-market businesses and their executive teams on how to transcend the barriers that are inhibiting growth so they can achieve bigger and better outcomes. Welcome, Terry. 

Terry Dry: Thanks. Good to be here.

Mike O'Neill: I'm glad you're with us. Let me tell our listeners a little more about you. I've had an opportunity to spend some time with, with Terry and he is best described is he's a serial entrepreneur, but he prides himself on practicing what he preaches. Not only does he advise existing companies, he also creates his own. So for over 25 years, Terry has founded, grown and reinvented companies.

And it's that entrepreneurial journey that I like us to spend some time while we're together a little bit about that journey and the lessons that he has learned along the way. So Terry, why don't you kind of get us set up. Your first venture into business? What did that journey start? 

Terry Dry: Well, first of all, thanks for having me. I love the introduction. I need you to introduce me no matter where I go, including you know, just downstairs to be with my family. So, that was, that was wonderful. I, I the I sound great. I feel good. 

Mike O'Neill: Well, you're going to be good. I'm confident of that. 

Terry Dry: I love, I love them buildup. The question is my first sort of business venture, or my first foray into any kind of business. 

Mike O'Neill: My understanding is you started in the music industry. Is that right? 

Terry Dry: Yes, it did. Yes. I was born and bred in Chicago and not a fan of cold weather and wanted to be in the music business. So I came out here to Los Angeles for college and never left, and I did everything I could during college. I took every odd job, every internship, everything you could imagine from selling t-shirts at concerts to just everything, to get my tastes and my fill.

And, luckily I started working in the music business straight out of college and all through my twenties. 

Mike O'Neill: So you work in the music industry through your twenties. And my sense is you pretty early on got the entrepreneurial bug. 

Terry Dry: I did. I would actually tell you I studied business in school and I kind of knew I wanted to run a business.

What I didn't realize is that I wanted to own and run a business. And that took once I got into the music business. And it was an interesting experience in that. The business was fantastic. I always joked that working in this industry in the nineties, which is when I was there, was sort of the last great moment of it before all of a sudden digital came and dramatically disrupted the business.

And so I got that run. And when I had that fun run, I was like, Oh, I want to run a record company. And then when digital came, I was very fortunate and I could kind of see it. And I was like, wow, this is going to be incredibly disruptive. And the fact that I was sitting inside this industry, That was very slow to respond.

In fact, if you remember when file sharing and Napster started, they not only were slow to react. They actually were suing people. They were suing their customers for quote unquote, stealing music. And I was like, That doesn't work. That's not good. Instead, we should have listened to our customers and try to pivot and offer music the way they want to digest it.

So all of that said, I, I kind of, again, being in my late twenties, naive, maybe a little arrogant, maybe a little over confident was like, you know what? I could do this better. I want to do this myself. I want to control my own destiny. And that's when I kind of set out on my first entrepreneurial journey, but that's where it really came from.

I wanted to run something and then I realized, no, I think I want to own it too. 

Mike O'Neill: So you had a background in the music industry. What was your first entrepreneurial venture? 

Terry Dry: So, well, I had several along the way, I guess I started little companies, little things here and there. At one point I was pitching a game show.

I was trying to do all sorts of different things. That was my Hollywood, era. And then, the first big thing that we really, embarked on was our agency called Fan Scape. And that started, was born out of the music business and was originally an online merchandise and fan clubs for bands.

And our whole thesis was we could use the internet. Now this is 1999, 2000, 2001. We could use the internet to keep artists and their fans closer together. That was the logic and we could cut out a lot of the middlemen. So we were selling merchandise, doing all these things, and that was sort of the very first venture.

And when I quit my you know, pretty great job that I had at a big record label. It was to just go do this. So I definitely have that entrepreneurial moment of going from the big salary and the cushy job to on Friday to Monday, literally, writing the check for the first and last month's rent on a big office space and with no revenue.

Mike O'Neill: That was obviously one of the first times you swallow really, hard. Tell us more about what happened with that business. 

Terry Dry: Well that business. I had to pivot a few times before we found the sweet spot, but we learned what we were great at was marketers. We weren't great at being let's call it merchandise fulfillment operational people, the data we were getting and the relationship we were creating between artists and their fans.

Was really, really valuable. And that helped us realize, okay, there's something here. And we pivoted and pivoted and became essentially one of what is called the very first social media marketing agencies and our happy accident was we came out of the music industry and music lent itself so let's call it digital marketing or social marketing really before any other big industries.

So we were doing, I always say social before it was called social. And that was a great, great training ground to grow and evolve. 

Mike O'Neill: You use the word pivot and I know that's a term in the last 12 months in particular, we've used a lot. But as an entrepreneur, do you find, have you found yourself pivoting a great deal?

Terry Dry: Always. And I think it's one of my kind of foundational things. And I think it's relatable to your, you know, this podcast of getting unstuck is the concept of continual optimization and continual change. And I kind of live by this phrase of change is inevitable, but struggle is optional. And if you kind of embrace change and then always look to optimize, always look to what can be better? What can change, what can evolve? You're going to stay ahead. You're going to be able to quote unquote, get unstuck and [00:07:00] enjoy getting unstuck and really enjoy this process of doing it. So I would tell you, in the first few years, pretty much of any business I've had, there has been a few pivots and the key is to keep pivoting, even when you're successful, keep evolving, keep pivoting.

Mike O'Neill: So let's kind of key in on the, the back half of that expression change is inevitable struggle is optional. Elaborate. What do you mean by that? That's why did you choose that phrase to almost be a tagline for your business? 

Terry Dry: Well I think what happens in the entrepreneurial journey is you get a little paralyzed, right?

You're looking and you're hoping, okay. I hope something sticks. I hope something works. And then if that's something does work, you're like, please nothing change. Just stay exactly the same, you know? And I came out of this industry in this business that did that. Right? So my exposure in the music business was, Oh my God, this is so great.

Everybody buys music on these CDs. Let's not change that we've got a business model that works. It's great, but Oh, look over here. Everybody's trying to consume their music digitally. There's another way I don't like it. No, let's sue them. Let's keep, I want to keep shoving this down their throat. So I think the concept is similar, which is. Yeah you want to get to that sweet spot, but if you don't keep looking in the, on the horizon, which is why I named my current company. Future Proof. If you're not always looking for what's ahead, you're going to get stuck. And you're going to, and eventually that's going to be a slow, slow death of your business.

And it's also, it's not fun, you know, it's not exciting. It's not invigorating, but the speed of change as you just brought up the need to pivot, especially in the last 12, 12 months is exponential. And that's because COVID sort of accelerated the inevitable, it accelerated all this change and it just made it happen faster.

So there's that much more reason to sort of sit back, look and keep pivoting, but embracing it. So back to the struggle is optional. A lot of people who they know there's change, change is inevitable, and it's all about your mindset and what you do with it. And if you recognize it, there's always going to be change.

Then you can decide I'm not going to struggle against it. I'm going to ride it, you know, like riding waves and I'm going to find the ways past it. 

Mike O'Neill: Terry, you just introduced something that I guess I've been thinking about as you were just commenting on that, kind of resonated with me. And that is, as we're recording this, we're recording this and March of 21, which means we've crossed in the United States about the one year mark of COVID, but you made a comment it was kind of interesting. And that is if change is inevitable, what you said something, and maybe I misunderstood you. But it sounded as if you're prescribing is the change that we have all dealt with has really, it sounds like to me, the way you said it, it's almost accelerated where this was going anyhow, did I hear that right?

Terry Dry: A hundred percent.

Mike O'Neill: Okay.

Terry Dry: Yeah. Yeah. I really believe that all of these things, you know, I called it COVID was the great accelerator of the inevitable, which was this transition to using technology to make your life better using technology for business realizing, you know, I come, the business I had after was I was in the advertising business and all people look to do is jump on a plane and meet the client, jump on a plane. You know, I had a day when I went LA to Miami and back in the same day.

Mike O'Neill: Oh!

Terry Dry: I went there for one meeting and came right back and you're just like, Wow, this could happen via Zoom. And, you know, I could've seen my kids for dinner, so I think there's a lot of things. And then let alone everything from Instacart to Tele-health.

So many things have changed and I think all these things were going to change, but when you get forced to behave differently, and really technology is this great enabler. It accelerated. 

Mike O'Neill: I know you came from out of a technology background. We've not talked about what you did after the record industry, and what you're doing now, but you've embraced technology very readily.

What might be some of the downsides? Again, our audience, as leaders, as leaders, we know that technology can be quite beneficial, but what might we need to be mindful of, of how technology may have some unintended consequences? 

Terry Dry: Yeah, I think, you know, there's, there's this concept out there of, the COVID 19, you know, meaning I I've heard it address where people are putting on 19 pounds cause they're sitting at home all the time, but I actually applied it to the COVID 19, as far as all of a sudden it's a 19 hours, Workday and technology makes it, you know, especially working from home, there is no more barrier, you know, I think you and I are old enough to remember you went to work you came home. Like there was no laptop. There was no smartphone. There was no, you know, in fact, when I started, there was no pager. They couldn't reach me unless they had the home number and you really had that disconnect. And now that's thrown out the window. There is no work-life balance. It's a blended lifestyle blended balance.

So what has tended to happen is people are working more, as well as in technology is enabling it. Where you really can do more. You know, you're not commuting, you're not you, you you've, you're finding more time in your day. So there is a danger in that you overdo it or you over-commit. Because technology enables everything to go that much faster can be a downside.

And then there's just the downside of human interaction of the loss of human interaction and what that does do people mentally and emotionally as well. And that's the cultural impact on a business. 

Mike O'Neill: Without a doubt. As we work with clients, one of the things we've spent quite a bit of time on in last year is helping clients make this transition to a virtual workplace, working from home.

And it's been really phenomenal to kind of observe how seamlessly some companies have been able to do that. Versus others. And I say that seamlessly because it's not a technology issue per se, but it's almost a cultural issue. And that is the point that you were making earlier is if we're not careful business owners, business leaders are on 24 seven.

You mentioned that the employees feel like they're on for 19 hours. Work life balance is a challenge. And I know that you have owned businesses, you've run businesses. You sold businesses. You still do that, but in your current business, you work with a variety of clients. I describe it is mid-market clients.

Let's talk a little about. What you're doing now, I have to start with the name of your company. I just thought this Future Proof Advisors, I love that. But when you named your company Future Proof, what will you hoping that the person who sees that interprets that to mean? 

Terry Dry: Thank you first of all. The hope is that they, they want to keep building right.

That they want to be future-proofed and it's trying to tap into that sort of entrepreneurial insecurity that we all have of like, what if I'm wrong? What if it doesn't work? Or what if this isn't going to last for another six months or a year or two years? Like everybody has those fears. I remember when things were going really well.

I would sit there going. Okay. When something going to go wrong, you know, and, and it's just trying to help, really elongate that. And future-proof, and I think so many entrepreneurs, especially in the emerging and middle market, which is what we focus on, which is what I've always been. You suffer from that sort of E-Myth moment where you spend all your time working in the business and very little time working on the business.

And it's a trap that we all kind of fall into. And so then you know, you're like, Oh, I'm going to get to that strategic thing. And you just don't. And so the idea is now let's future proof you forward. Let's help you really take some a longer look at your North star at your vision at the landscape around you.

There's probably things maybe that you haven't even thought about that we can be thinking about and seeing, you know, down the road that are potential pivot options or different options for you. And that's the whole idea. It's, future-proofing your business, but it's also future-proofing the entrepreneur themselves, because sometimes we become servants to our own business rather than having the business serve us.

Mike O'Neill: You're making an interesting point here. And that is, a entrepreneur who find who, who is the founder of a business, finding a founding, a business and running the business are very distinct. Roles.

Terry Dry: Yeah.

Mike O'Neill: But you made an interesting point in that is, it sounds as if you and your team, when you're working with business leaders and the organizations you're focusing and encouraging to look not only at future proofing the business, but they have to pay attention to themselves.

The description that you just made, sounds to me, more strategic planning, execution. Describe the kinds of services your group provides your clients. 

Terry Dry: Yeah, I think, it's really, you know, you described it really well Mike. It's so much of the entrepreneur or the it's about their mindset, you know. And if you just go straight into the tactics of, okay, we're going to put this process in place or whatever you might lose, what might be underneath.

And I know this is a lot of what you do in your business of coaching or just unearthing, what's really driving them, you know. Do they still like it, you know, like, so, you know, some of the companies that I've worked with, it turns out, you know, one of the founders, like, you know, I'm kinda over it, you know, and, and I've, we've had a good run, but I'm, I'm tired.

Like I want to have an exit or I want to do something else. And so it really starts there, but it really worked with people who want help. And I've set this company up my concept is we kind of function as this almost like an outsource board an outsource board of directors, because what I find in a lot of the mid-market companies is they haven't really established a board.

It was somebody who went and started something. And they're great. They're a great operator, great hustler, if you will. And then it grew and it grew, and it grew, and it's time to move from small business to like professional business. And they never really had this surrounded themselves with these experts. And it's born out of what I wish I had had 10, 15 years ago when I was learning and growing and doing all, this was like, Oh my God.

If I had had this kind of, I jokingly call it the justice league of America, like having superheroes in each one of their specialties. If I had someone who really understood MNA and I had somebody who really understood operations and somebody who really understood strategic partnerships around me as sort of mentors, confidence, coaches, whatever.

I could've gotten so much further, faster, but I just didn't know what I didn't know. And I was like, God, I would really love to be able to do that, that for the next company. So they can learn from mistakes I've made or I can surround them. It's not just about me, surround them with these other experts that will just help them.

Not only get further, faster in their businesses. But enjoy their life and enjoy the quality of their life. And I saw that, you know, I think on your website, it was just like, I'm going to help you sleep better at night, you know? And that, that's a big, big piece of this. So that's a big part of what we do.

And I've found that the middle market just they're almost being ignored on that. So we're trying to help with that. And I call it like, we're like your secret weapon, or, you know, this, this secret thing that you have their guide to help them go because we've kind of been there, done that and that, that helps them along.

And then there's a process and that all those other things that come with it, but I think it's really that concept of, of helping from that level. 

Mike O'Neill: Yeah, I kind of want to break down what you just share with me into two different camps. One is when you're working with the founder of the business and you use a term North star, I'm going to make the assumption that when you begin working one-on-one with a founder, one of the things you're trying to get a feel for is to what extent does that founder still find excitement that they get up and do they have that same excitement that they had when in the early days. And you've already mentioned, you've had situations where they just don't. And what happens from that is a variety of things I would suspect. One thing would be, is it maybe it's time for them to transition into a different role or perhaps out, or, how, how do you think that one through, when you're talking about the North star, do you help business owners clarify what their North star is personally?

Terry Dry: Yes. Definitely helped them personally and professionally and where I find myself being obnoxious is that I get so excited about their business. I'm like, I think I know what your North star is. Like, I see something else. I see this opportunity and I want to be able to collaborate with them. But I luckily know enough to like shut up and listen to them and really try and get like, what do you, so when we get into it, it's all about that.

It's like, what are your goals? Like the first thing is just like, what are your goals? Not just for your business, but for your life. And some people will tell you, I just want to enjoy what I'm doing. Some people are like, I want to make a hundred million dollars. Some people, you know, there's so many different things that you'll hear.

But just getting that to come out because sometimes, and again, I went through this, I was so gung ho I had to be successful on the entrepreneurial side that I wasn't even sure what the goal was. And I just, I just, the goal was like, I don't want to not make payroll, you know, like you still came from that like scary time.

And so just helping them with that. And then once you know where they're coming from and their desire, then you can start to put the North star together for the, for themselves, for the company. And oftentimes that's how we do it. We'll work with the entrepreneur, the owner, and understand just like, what do they want out of their life and out of their business.

And then you set it up so that the business can support that. And then it can be a whole North star strategy for the entire company. You know, it's not necessarily about the owner wants to make all this money. It's about, let's grow this business. And you're right. Sometimes somebody wants to hand it off to somebody or they're not even sure.

But they're, they're kind of aimless and they're like, wow, 10 years just went by, like, and that's why they're calling me. Like, I can't believe it 10 years just went by and like that. And I'm still, and we're doing fine, but I want to have more of a strategic plan. And so that's when, when you know those goals, you can sort of back the planning into it, but it's this combination of personal and business that'll really help drive it.

And that's how we try to help people do it. And it's a lot of fun. 

Mike O'Neill: You know, business owners oftentimes start and they have to wear every single hat. And as the company grows, they realize they can't do it alone. They began to hire people. And what you described is the niche that you like to work in you and your team is that mid-market and that is, they are growing, but they haven't necessarily built the infrastructure or the processes necessarily to sustain that.

When you are working with a business founder who started wearing all the hats, do you find that there is  to let go of some of the duties that they've always had? 

Terry Dry: Yes. Sometimes. Yes. And sometimes, you know, I've had people like myself, for instance, when I'm starting a business, I'm like, I want to build it and I can't wait to, I want, I want to replace myself.

I just want to keep replacing myself. Some of them do and some of them don't. But what's interesting is some of them are like the creative force behind it. Or the creative energy or, you know, whether it's somebody at an agency or somebody in an e-com or somebody who's a designer or somebody who's a writer, like I've seen them all where they're like, I really just, I love the work.

I started this business because I love to work, but now I have to deal with all that stuff. And they, they just haven't realized, well, let's hire a great operator, let's hire this. And it's just trying to help get the infrastructure. But I guess to the point you're making, it's identifying what is their sweet spot? What do they enjoy? And then give it, making sure they have that role. And you can still be the founder the whoever, but you don't necessarily have to wear all those hats. But sometimes they literally don't know that, or they're not sure. They're not sure how to go about it, or don't even know that about themselves just yet, but that's only sort of the phase, one of, you know, I'll call it advising, coaching, whatever. But then there's so much more like operationally structurally that we help them do.

But you're right. You'll find that people either don't know how to give it up. Don't want to give it up or don't even realize what they're not doing as well, which is always interesting.

Mike O'Neill: Your quick to point out the theme of this podcast is getting unstuck. So let me ask the question along these lines. Can you think of a situation where either you Terry or a client that you were working with really just got stuck and when that happened, what did it take to get unstuck? 

Terry Dry: Yeah. You know, I'll, I'll use myself as the example because the company I was telling you about our agency, we kind of built as one of the first social media agencies.

It grew out of music. Then all of a sudden we were working with big brands and we really became one of these first social agencies. We were doing well, but we were always kind of hovering around, you know, it was somewhere around 4 million in revenue and maybe half a million or so in profit, which was nothing terrible.

Everybody's getting paid everything was fine, but we were just hovering there and I'm like, wow, we're in this really sexy space that's growing. And, we're kind of, we're doing fine. We're doing well, but you're just like, it felt we were stuck. And, and I was stuck because there was literally like, I don't know.

And my partner and I were like, we're not sure what else we can be doing. You know? And I would also say 2008 had happened, which the business went down. So that scared the life out of us too. And you're just like, okay, I just got to make this work. And what started to happen was it started getting bigger.

Like I realized the industry was getting bigger, but we weren't. And I, I felt very stuck and we made a decision. We're like, we're either we need to sell this company or partner with somebody else in order to grow. And so you get to this stuck point and there were different moments where it happened, where I lost a big client or something, and you're like, wow, I'm playing in a different field now.

And we're going to need to either become, you know, hate the player, hate the game, or become part of this thing or partner with it. And we made a very conscious decision that it was time and that we needed to sell the company to actually grow the company. And so that was this period of being stuck and kind of frustrated and a little scared.

And then, and going, no, this is the right strategic thing to do for the business. And it absolutely was. We wound up selling to a big public company and had a very successful earn-out and. All great things happened. And, but it was as a result of feeling stuck in sort of shaking ourselves into no, we've got to make a change or this isn't going to work. And I think 2008 and that problem of the economy, if we weren't going to shake ourselves, that sure did shake us. 

Mike O'Neill: Terry, I think that's a perfect illustration. Why I suspect that you resonate very well with your clients because you literally have been in their shoes. And, you can just speak from firsthand experience.

You know, we have very quickly kind of recapped your professional journey, your entrepreneurial journey, but if you were to kind of reflect on the things we've talked about, or maybe things we haven't, and you want to make sure that. People have as a takeaway, what might be some things you want to make sure our listeners remember about this conversation?

Terry Dry: Well, thank you. It's been fun talking to you. The thing I'd want them to remember is you don't have to be stuck. You know, and I, and if you're listening to this, it's because you probably feel stuck in some way, and it just doesn't have to be that way. And there's all sorts of people from what Mike does with his company, to what we do, who can be helpful to you.

And sometimes it's one thing that you need it, but you need to kind of want it and embrace it. And I can't tell you how valuable it is to sort of be vulnerable as a leader and open yourself up to saying. Help me, you know, or ask for advice and seek help, because it can help you in so many ways, because being stuck is just no fun way to live your life, really. And, and, there are people like myself where I've been very fortunate to have success in my life and. I'm really enjoying this phase of my career, where I'm able to help and give back to people and help other people be successful. By sharing what you just said, I seem to have had every scenario good and bad. We're we're talking about the good ones here. I've had the bad ones too. And, and just try to do that. And, the only other thing I always like to say to people is just try to be kind and be respectful and do what you say you're going to do. And you're ahead of most everyone in business. 

Mike O'Neill: That's not only good business advice. That sounds very fatherly advice.

Terry Dry: It is.

Mike O'Neill: Very well said. Terry, if folks want to reach out to you and connect with you online, what's the best way for them to do that? 

Terry Dry: I think the easiest way is just to find me on LinkedIn and, and shoot me a note there. Or you can always send me an email at Terry@futureproof grp.com, but it's future proof than GRP short for group.

So Terry@futureproofgrp.com. 

Mike O'Neill: Excellent. We will include your contact information in the show notes. We will include a link to your LinkedIn profile and we'll include a link to your website as well. So if folks are out driving, listen to this, don't worry about it. It will be in the show notes. 

Yeah. Keep your eyes on the road. 

Yes, that's exactly right. This has been a real treat. Thank you, Terry. 

Terry Dry: You too. Thank you so much.

Mike O'Neill: I also want to thank our listeners for joining us for this episode of Get Unstuck & On Target. We upload the latest episode every Thursday. And if you haven't already please subscribe.

You know, life is too short to live. This is problems. Keep you up at night at Bench Builders, we love helping clients solve the problems that are holding you back from the success that you deserve. So you've been listening to my discussion with Terry and you're realizing that something's keeping you or your business stuck.

Let's talk, go to our website, bench-builders.com or just go to your browser and type. unstuck.show to schedule a call. So I want to thank you for joining us and I hope you've picked up on some tips to help you Get Unstuck & On Target. Until next time