Grey, I’m so excited to have you on season two of the Frontier podcast.
I am very excited to be here. It’s cool being on the guest side of the equation.
Hell yeah. It’s also fun, because I feel like with these staff interviews, I am learning so much about everybody on the team. We talk every day. You and I have been working together for four years, and I feel like there’s still just so much cool stuff we haven’t talked about. I had a conversation with Wade last week, and I learned that he was a college water skier, like a competitive water skier. (Grey: Yeah.) You knew this.
Yeah. Only because he floated like a screensaver at some point of him on a slalom course. And I was like, ‘Is that you?’ But he never would’ve mentioned it otherwise. But we ended up talking about these things—these manmade lakes. I was like, Where’d you ski? Or whatever. Yeah. I didn’t know about this. There are hundreds of manmade ski lakes all over the country. (Faith: Really?) And like when you’re sort of a pro or a teaching pro, a lot of the sort of semi pros make a lot of their money doing like summer courses and stuff. So they’ll just hop around to these different manmade lake—and they’re awesome—and teach people how to do courses and competitively ski and all that kinda stuff. It’s like a whole thing that I didn’t know existed.
I had no idea that existed either. And I feel like I grew up probably closer to lakes and water sports than a lot of other people. So I’m a little bit embarrassed that I didn’t know that.
He’s got a map.
Ask him about his map, yeah.
Okay. Maybe we’ll put that in his show notes. Do you have any surprising previous professional stints that I don’t know about, other than being in a band?
Not that I’m gonna talk about, nope.
What? Come on.
No—everybody’s got a life before their current life. Well, when you’re my age, you have several.
Yeah. You’re not old, by the way, Grey.
Old enough. Old enough to have several phases. (Faith: Yeah.) I had—it’s relevant, ‘cause it dovetails nicely into what I do now. Like, I started out moving to Nashville to pursue music, like everyone that moves to Nashville, pretty much—and did that for a while, and ended up getting in—this was a long time ago, so this was like early days when artists were first starting to think about electronic press kits and like their web presence. No one had a website. Like there were barely any websites, you know. So that kind of drew me into technology and gave me a nice jumping off point out of the music industry, which was gonna be a dead end, you know, ‘cause it is. But yeah, so you know. There was definitely a former rock and roll life before technology, but that’s been a good while.
That’s an interesting segue. I hadn’t thought about how you got into tech before, and I was actually just having a conversation with a friend who was probably working in music around the same time, and he had a pretty high level position at one of the publishers here, but he was doing all the print packaging, like all the CDs. (Grey: Yep.) And he saw the writing on the wall. He’s like, I have got to get outta this. And now he’s like a real estate mogul. So I’m glad that everybody found their way out of that world and into something that that was good for them.
Yeah. I mean, it’s interesting, because most people that you talk to around town—and maybe your friend is in a similar position—like there are a lot of people in music that were basically generalists, you know, and they were drawn to music, and they wanted to make a run at music, because it interesting to them. But, you know, their aptitudes or talents could be applied in many ways, you know? And you know, for me that happened to be, you know, sort of a pension for technology and an interest there. And that drew me into the studio, which drew me into the internet, which drew—you know, like that was that path. Yes. And it’s through music, but I was never gonna be a musician. That wasn’t my core thing. It was something that was sort of adjacent to music that ended up being the thing. And I think a lot of people are like that. A lot of people here, especially in town or in music industry towns, do something else starting in music. But music is a great jumping off point for doing lots of other things.
Yeah. I wanna put a pin on in this and circle back to it in like 30 seconds. I think probably to start, it’s gonna be relevant for folks to know what you do here at Gun.io. So what’s your job? What do you do every day?
I try and guide the product to be super useful to clients, be super useful to talent, be super useful for our internal teams to help companies and developers find one another. So the perfect gig, the perfect hire is sort of our North star. And so everything that we do is sort of aligned around trying to make that happen. And you know, we can get into the nuts and bolts of how we do that and what parts of the application, if you wanna dive deep. But yeah, my sole focus is on building our software to support all parts and all parties— staff, tools, talent, and clients.
Yeah. When I think about your role, I think of the animated ‘How it Works’ videos that you see everywhere, where it’s kinda like the inside of some machine, and you’re following like a ping pong ball as it goes through mazes and whatever. And it’s all about kind of getting everything on the right path and filtering out things that aren’t relevant. And I feel like that’s really your job. You’ve got so many input, so many requests from people, whether it’s our users or on the outside, right? Like our clients, our developers, or our internal users, which are our staff. It’s not as probably fun and forward facing as it seems sometimes when it’s like, Oh cool, Grey just gets to think about building cool stuff. It’s really, I imagine that filtering mechanism is hard sometimes. Kind of deciding what to build and how to group things and what the value is.
It’s certainly the challenging part of it, but that’s also why you do it, you know? To be that conduit between something that could be, and then shaping that into something that ultimately exists is super gratifying. And so the challenge of everything that you said is spot on and, and you do a lot of that, but I have always been sort of drawn to, you know, things that feel like puzzles and making sense of things and translating things, you know—not to dwell on the music thing—but that was a big part of what music was for me. It was in the studio, and it was taking a song and assembling it, and at the end, you take these disparate parts, and you iron them out and you craft something that in the very end is sort of the sum of all the inputs. So the product to me is sort of that same part of my brain where you take a lot of inputs and try make sense.
What’s up y’all? (Grey: Hey dude.) Sorry for joining late. I wanted to be here for this one ‘cause this is a fun one, so yeah.
Sweet. Teja, I’m glad to have you here, because I feel like Grey, similar to Wade, has just like a really fun professional story of how he landed here with us, so we’re gonna dig into it.
Yeah, totally. He’s one of the, the Emma Mafia as well.
Well, let’s circle back to that. We started getting into kind of how Grey found himself in technology, which obviously led him here eventually to Gun.io, but there was a decent chunk of time in between. So Grey, take us back to, you know, you kind of found a path away from the music industry following this line of tech, and where did that take you? What was your first stop?
My first stop was a new startup, sort of a 10 person startup, in the email marketing space called Emma. And it was a local company, and I didn’t know what email marketing was—and most of the world didn’t know what email marketing was.
What a time. What a time.
Yeah, right? I mean it was—yeah, these are early days. I mean, people didn’t even know what an iPhone was, much less what email marketing was. So there was constant contact that was kind of out there, but it was a little bit like, mm I don’t know, it’s kind of hard to use. So a couple of guys, Clint Smith and Will Weaver, started this company sort of on a whim in Nashville, which you didn’t do, because the technology scene was not a scene all. It was just some developers and some ideas, and hey, we can make a dent in the space because it’s—the incumbent is not good, and there’s tons head room here, and we wanna create a brand. And the brand element of that was an important through line with that whole company. It taught me a lot just about, you know, the intersection of technology and brand and brand positioning and where those things need to compliment one another. So they decided to start this company, I jumped on board super early, and we were all just wearing a bunch of hats and stuff like you do in startups, and eventually found my way sort of sitting beside one of the co-founders every day thinking about what the next version of the product was gonna be. Because the version that was out in the world in production that people were paying for was kinda a first iteration. It was like, oh, people like this? Great. Let keep buying it. Oh, but there’s some stuff we gotta work out over here about what this next version is gonna be. So he and I worked together for a couple years and sort of developed the notion of what product was at the company. We had some really talented engineers who were grinding every day to build and maintain the product, but there was technology, but there was really no function thinking about what the next thing was, or what the user experience was, or how even to get feedback.
So he and I sort of laid a path to create a bonafide product organization. And over the years we were able to do that and bring some talented people on, which, you know, at some point we sort of had our bearings. And that gave us the opportunity to actually start thinking even further out. So I started essentially what’s a kind of skunk works type of idea where it was sort of, you know, product development that was way out in front, and it was in an innovation space, and it was what’s happening adjacent places in our industry. Where’s the industry going? And this is the beginning of really social media and brands starting to use social media in a meaningful way. What does that mean? How does that intersect with marketing? Those types of questions that weren’t about like, hey, what’s the next incremental feature that we’re gonna build or maintain or fix. And that was really—that’s been meaningful for me as a throughline throughout my career, is being able to help navigate where things are going, and taking market inputs and reading tea leaves and trying to figure out how technology is gonna play a role a year and half, two years, five years down the road.
And eventually, you know, when I left Emma, it was those 6, 8, 10 years of learning in product that was the impetus for the next phase of what I did, which was hop in as a consultant to other companies that were at that earlier phase, now that Nashville kind had a little bit of momentum, and there were more startups around, a lot more companies needed help getting over that first or second hurdle. So I was able to take all of those learnings from how to build a product team, how to think about the intersection between engineering and product, how to build roadmaps. ‘Cause my first roadmaps were a disaster And then thinking about how that dovetails with business strategy. ‘Cause technology enabled business or people building products, I mean it’s the business, its what people are paying for. So there is a fundamental intersection there. And so helping other startups navigate those first couple phases is what the first phase was for me, and then Gun happened to be one of those clients. Five years ago now, met Teja at a coffee shop, and he let me know what you guys were up to and the vision, and I was like this is super cool, let’s work together.
You remember what coffee shop we’ve met at?
It was in Germantown.
No it wasn’t Steadfast, it was right down—it was right there near that 3, 2, 1 pizza thing.
Probably Red Bicycle.
It was Red Bicycle. Yeah. A little picnic table out in front.
That’s hilarious. ‘Cause Grey, that’s where you gave me my offer when I got hired, was a little picnic table in front of Red Bicycle.
That’s exactly right.
Very good through line.
We should put a plaque there.
We really should, this is where Gun.io was built, this little picnic table.
And so one thing led to another, and you know, we started thinking about who we can bring on, and you came along, Faith, and then we started building websites, and you know, then it was a product, and now we’re here and it feels like a year, but it’s actually been quite a few.
It’s been a long time. There’s so much—like I can see how, if you think of yourself as a T shape, not just like marketer, but professional, you’re kind of deep obviously in product, but I feel like there’s so much at the top of that T. Like I go to you for advice about everything growth and marketing related. So I’m curious if you had to kind of categorize yourself, if there’s like one kind of area of expertise that you think you’re strongest in, what would that be?
I think it’s probably product strategy, because that really is the intersection of all the things. Like I don’t really like that phrase, because it doesn’t mean anything. But being charitable with the phrase, I think it’s important. Because if you’re doing things right at the product level, then you are reflecting the needs of the opportunity in the market. You’re reflecting solving problems, you’re creating value. And for us that is, there are a couple of stakeholders in that. You’re doing things that are unique and differentiated in the marketplace that draw people to you. You’re helping support a brand. Like, so all of those things, if you’re doing product well, have hooks into all other parts of the business. It informs packaging, it informs how you sell and informs how you position, you know, and some of it just so happens that I’ve been around long enough, Faith that, you know, I’ve had to dip my toes a little bit deeper into the weeds in a couple of different areas, marketing and sales etc. to kinda understand the lay of the land at an operational level. But I think it all—the understanding really stems from how to create that, you know, and then how to translate that into software.
So, you know a lot about a lot of things, and you’ve worked in different facets of the organization, not just ours, but you know, any tech startup. What’s your learning process, and how did you acquire the expertise, you know, breadth and depth? Did you learn by doing, did you seek counsel? Did you have a peer network? Did you read a lot?
Yeah, it’s a great question. And it’s all of that. My personal opinion is you kinda need all of that. You need those inputs, because you learn different things from different sources, you know, early on, you know, this was— when I started in technology, I mean the, the Agile Manifesto had just been written.
Wow. That’s crazy.
Yeah. I mean, so those early days were about sort of building a community almost around these core principles, and what does the next era of software development look like and what role does product play in that? And can we do things better, and how do we not legacy waterfall enterprise and how can we, you know, all of these were new questions. And so building a community, having mentors you know, either local or online mentors, early days Steve Blank and the Eric Reeses of the world that were really spearheading some of these early movements who were critical. And then the complimentary stories and postmortems from people who had either been successful or failed, where it was a critical part of just consuming what, you know, beyond my experience, how can I learn quicker? You had to learn from experience. My list of bookmarks is like a thousand entries. It would be like an interesting archive actually to go back and check that out from like the very early days. It’s like, it’s a thing.
We should do a blog post on that and then put it in the show notes. I think that would be really, really cool. Even like, ‘cause you know, you’ve been doing this for years, throughout your whole professional career. And so it’ll be really interesting to think about bits of that, that are no longer relevant, that have been proven wrong, that we now have a better way to do it. That would be really cool. Let’s do that.
Yeah, I’ll curate it.
Ok, fine. Deal.
Like I remember when we were first started working together, what really struck me is like the extent to which we shared like a common context and understanding already about like where the business needed to go and of what we were trying to do with the business. That’s actually what was like really, I don’t know, like comfort inducing—there’s probably a better word for that.
Comforting. There you go. Yeah, because—no, because to your point in Nashville, right? This whole notion of like building a tech company, trying to be capital efficient, trying to have the optionality to be venture backed at some point like that is actually, it’s a fairly—of all the possible business outcomes, it’s like a niche within a niche, right? In terms of a strategy that you’re trying to pursue. And there was like a sense of like, you know, maybe it’s the ecosystem that Emma had maybe accidentally built by virtue of hiring and building the company that people like you exist here in a city like Nashville. That was like, really a surprise. I have to give credit to jumpstart and everybody else in the ecosystem too but I remember that, being like, holy shit. Like I’m glad that we are working together.
Yeah, well I mean you guys actually deserve the credit for that, because I would—I was reacting to the way that you guys were already operating and your sort of philosophical approach and building a solid business, and then thinking about, you know, funding and scale and all of that, those sorts of things. And you know, especially at that time, dude, that was not true. That was not true. It was get funding first and figure out how to do something relatively cool later. That’s where most startups fail. It’s because they’re not approaching it about—they’re pursuing an idea, not building a business. And you guys were already building a business. So we were super aligned on, okay, let’s keep that intact. And then let’s figure out ways to accelerate that. But let’s not forget the fact that you guys have a great fundamental core business. And so to me it was something that alignment was, because you guys were already doing things right.
It’s so funny to me. I feel like that belief about business, Grey, that you just described, like let’s build a solid business, kind of do like the super unsexy, like manual, just business doing and then think about funding is like..It’s all so—that trickles down into how you think about product level decisions on the team. Like let’s do it manually, let’s prove it out. Let’s run kind of as an experiment based company and then we’ll invest product and engineering resources and automating it. So I think that’s the thing that probably makes you a good product owner too.
Well, thank you. But you’re right. Like that spirit, that through line of, you know, I mean even going back to the Agile thing, like that whole principle was based on can you create something of value quickly and how quickly, and the quickest you possibly can create some value. And then once you’ve proven that it’s valuable, then do the next thing. And so it’s pragmatic. And to your point, sometimes it can feel a little bit like, hey, can we, you know—
Hit the gas a little.
Yeah. Or what—but that is hitting the gas. Because moving recklessly in the wrong direction is going to catch up with you. And so ultimately, you do move more quickly when you can build on the momentum of doing the right thing over and over.
I’m curious—if somebody’s listening, and they heard you describe kind of the role of a product strategist, and they’re like, Man, that’s what I wanna do. That sounds really compelling to me. What advice would you have for somebody who’s getting into the work that you do in 2022, which is much different than at the precipice of like, Agile?
Yeah, right, exactly. I would say don’t try and become a product strategist. I would say—
I would say find a company that you believe in and—I’m not trying cheesy—but belief in what you’re trying to accomplish. The vision of the company is super important, because that’s gonna give the motivation to go out and talk to customers. It’s gonna give you the motivation to study the industry to see what’s going on. And it’s gonna give you the opportunity to actually apply all of that learning in a practical way at a level of the company that you can see immediate output for. Because the problem with strategy is that it’s vaporware a lot of times, it’s speculation. But being a product owner and being steeped in the discipline of doing that day to day and actually being able to see the result of your work and then to have that measurement and that feedback, positive or negative feedback from users, that’s informed strategy. Because your empathy and your intimate understanding about what creates value is the thing that’s gonna drive the strategy. So strategy is something that you get as a benefit for being really good at being an on the ground product owner.
Right. And working on something that gives you a lot of energy.
So one question is, how do you assess what company to work for?
Like as a consultant?
Yeah, as as a consultant, and then how do you assess or—as a consultant, I guess it’s actually more appropriate, like how do you assess what company to consult with and partner with? ‘Cause the relationship is a little bit different. But then also how do you assess what company to actually go and build, you know, with the founding team. Like what, especially as an experienced person, you know, you’re kind of stepping into like, this company might be a clusterfuck or whatever. How do you, like—what are some things that you think about?
It has to start with the founders, or whoever’s setting the vision for the company. You have to be aligned with that. And it has to be interesting to you, right? Like, I’m sure I could look at a business in an industry like healthcare—I’m not really interested in healthcare—but I could probably sit down for coffee with the CEO of a healthcare firm and be aligned with them about how they’re thinking about their business. Just not interesting. So like to me, it being interested and aligned with the vision of the company is the first thing to even—and then you start actually, for me it’s like what does this company look like without me in the mix and what does it look like with me in the mix, and how much room is there for me to bring value to the table?
Because ultimately that’s the thing that’s gonna mutually beneficial, and you know, it’s gonna keep interested. It’s also gonna create value for the company, and the relationship is gonna be good there. And so sometimes I’ve found opportunities that, for whatever reason, like, it wasn’t firmly, directly in, you know, my skillset, or whatever it was—it was like on paper, yes. But practically, you know, two or three months down the road, this is not gonna be my sweet spot, and we’re gonna be looking for someone to replace me. So i’d rather just advise them to go find that person from the jump. You know? The interest and being able to actually have enough headroom for what you bring to the table is critical from a consulting standpoint. But then jumping into a team—it’s everything about the team, you know, for me, because the level of commitment’s obviously super different. Investment is different and you know, as a consultant, you can work in one department or even with one person, maybe even a sync to the business itself, but to become a member of the company, to me, it’s all about the belief in the group of people that’s being assembled to do the thing. Probably check the couple boxes already align with the founders interesting work. But jumping in is all about, alright, well who else is there, and how well does that team function as a team to align around the common goal? And that’s probably the hardest thing to do. But that’s the final checkbox for me is can I play a meaningful role on this team as a teammate? And then can I help shape who else we go get to help us accomplish what we’re trying to do?
I think often, I mean, we work with people who contracted businesses, that’s our job. So, and it’s really easy for us to tell when there’s a business who has a need for a contractor, but they haven’t done the pre-work of bringing in a consultant like you where they really understand like, here’s the value we expect this person to drive. And I imagine that that’s part of your calculation as well. And it, you kind of touched on it, right? Like is my expertise and my unique skill set a fit for what it is they actually need? And if the business doesn’t know what they need, then that’s a pretty easy no, I imagine.
Yeah, for sure. I can’t tell you how many businesses I talk to. That are like, you know, we need help with sales.
Right, we just need to grow faster, we need to make more money.
Right, exactly. Like, what business doesn’t need more sales? Like everyone always wants more sales, but that doesn’t tell you much of anything, and we may need to drill in here a little bit. To your point—sales is a really big thing. And so like, what are you good at? What are you not good at? What’s the market like— it’s the weedy stuff that really, you know—and I mean that’s true with all aspects of any business. Like generalizations are usually like, you just haven’t put the work in.
Right? Yeah, exactly.
Yeah. It’s interesting, you know, I mean you touched on like product strategy. I think what made the relationship feel so good I think, initially, was that there was clearly an opening and a lack of, at least on the existing team, a lack of knowledge and experience around product strategy. There are a lot of CEOs or founding team CTOs who have strong opinions about product that probably actually, like, there’s not enough actually cognitive or strategic room to have a fully fledged sophisticated marketing department even, let alone a product strategy and product function, right? It’s like basically order taking on marketing or order taking on product, or even order taking on roadmap, right? But that didn’t exist here actually. Like, you guys kind of stood up both things. So, you know, I don’t know, like that’s probably unique. I think a lot of founders would have strong opinions about those things, but we certainly didn’t. And I think it’s worked.
I think building new things, it’s, you know, it it’s ultimately about communication and transfer of ideas between people. ‘Cause people do all the things. And so if you can sort of have a vision for what you want the future to look like, then the methodology or, or how you would put the idea into a department who actually does that work—they’re very similar. You know, it’s just the skillset of the person that is executing the deliverable, you know? Product strategy and marketing strategy and business strategy and for a technology business , you know, like I said before, they’re so intertwined and the Venn diagram is almost a circle. The question is less about strategy and more about like, alright, who’s gonna go do the thing that we want done? And what skills do does that require, You know?
Yeah, exactly. Well, Grey obviously is a great person to talk to about product strategy, but also about music and Nashville hiring strategy, all kinds of stuff. So if you wanna get in touch with Grey, he’s on Twitter sometimes. So you can find him there. And you can also find him here on the team at Gun.io. Get in touch, and we’ll make sure that you guys get connected. Grey, thank you. I learned a ton. You did not disappoint. Very interesting career arc, and we’re just thrilled to have you here, too.
Thank you! I appreciate the invitation. Yeah, this is fun.
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