Ray Winninger is a seasoned video game pioneer who began his career as a freelance designer in high school. His most recent role was as Executive Producer at Wizards of the Coast, where he managed a studio for Wizards’ Dungeons and Dragons. Ray’s career spans over 30 years, leading departments for prominent companies such as Sony, Viacom, Microsoft, and Amazon.    

Here’s a glimpse of what you’ll learn: 

• Ray Winninger shares how his passion led to his dream job in gaming
• What was Ray’s contribution to Dungeons and Dragons?
• What attracts people to continue to play D&D?
• How can historical companies create innovative products while maintaining their nostalgia?
• The future of tabletop games and AI in gaming
• Understanding go-to-market strategies
• Ray’s career advice for overcoming imposter syndrome and succeeding in the industry

In this episode…

The popular tabletop role-playing Dungeons and Dragons celebrates its 50th anniversary this year and is played by more than 50 million people. How can established publishers like D&D maintain longevity and popularity?

As gaming industry pioneer Ray Winninger explains, one of the most significant appeals of gaming is the ability to immerse oneself in another world. D&D developers understand that people enjoy being able to create characters and stories with no restrictions. Although it may seem obvious and trite, Ray affirms that companies must employ product developers familiar with their target market. This necessitates that game designers and company heads conduct polls and studies to determine what’s popular and why their clients prefer certain games. 

Join Lizzie Mintus on today’s episode of the Here’s Waldo Podcast, where Ray Winninger, a pioneer in the gaming industry, joins her. The two discuss the quintessential Dungeon and Dragons, Ray’s contributions to the brand, why D&D has maintained longevity, and how historical companies can create innovative products without losing authenticity.

Resources Mentioned in this episode

• Here’s Waldo Recruiting
• Lizzie Mintus on LinkedIn
• Ray Winninger on LinkedIn
• Tyler Wright on LinkedIn
• Women in Games International (WIGI)
• “Creating Opportunities and Advancement for Women in the Gaming Industry With Joanie Kraut” on the Here’s Waldo Podcast

Sponsor for this episode...

This episode is brought to you by Here’s Waldo Recruiting, a boutique recruitment firm specializing in the video game industry that prioritizes quality over quantity and values transparency, communication, and diversity. We partner with companies, creatives, and programmers to understand the why behind their needs and provide a white-glove experience that ensures a win-win outcome.

The industry evolves. The market changes. But at Here’s Waldo Recruiting, our commitment to happy candidates and clients does not. 

We understand that searching for the best and brightest talent can be overwhelming, so let our customer-first staff of professionals do the leg work for you by heading over to hereswaldorecruiting.com.

Episode Transcript

Welcome to the Here's Waldo Podcast, where we sit down with top visionaries and creatives in the video game industry. Together, we'll unravel their journeys and learn more about the path they're forging ahead. Now, let's get started with the show.

Lizzie Mintus: Hi, I'm Lizzie Mintus, founder and CEO of Here's Waldo Recruiting, a boutique video game recruitment firm. This is the Here's Waldo Podcast. In every episode, we dive deep into conversations with creatives, founders, and executives about what it takes to be successful. You can expect to hear valuable lessons from their journey and get a glimpse into the future of the industry. This episode is brought to you by Here's Waldo Recruiting, a boutique recruitment firm for the game industry. We value quality over quantity, transparency, communication, and diversity. We partner with companies, creatives, and programmers to understand the why behind their needs. We provide a white glove experience that ensures a win outcome. Before introducing today's guest, I want to give a big thank you to Tyler Wright for introducing us. Tyler, we were talking before the show, you are so personable and enjoyable. So thank you for the connection. Today we have Ray Winninger with us. Ray began his career in gaming by working as a freelance designer while still in high school. He's worked in various senior roles at Sony, Viacom, Microsoft, and Amazon, among other places. Most recently, he was the executive producer responsible for running the Dungeons Dragons business at Wizards of the Coast. Let's get started. Thanks for being here, Ray.

Ray Winninger: Thank you. It's a pleasure to be here, Lizzie.

Lizzie Mintus: Thanks. Can you share a little bit about your journey into the industry and how you found yourself as the executive producer at Wizard? Ray Winninger: Yeah. It's interesting because as you touched on a bit in a summary of my bio there, my connection to Dungeons and Dragons, ultimately ended up at Wizards goes all the way back to when I was in high school, I started playing game when I was about 12 or 13 years old. Like many people who find their way to the game, I became quite obsessed with it as a kid. And I spent a couple of summers after I really started getting into D&D. I spent a couple of summers sitting down with an old electric typewriter. This dates me. This shows you how old I am. And banging out manuscripts for D&D, imitating the D&D products that were out there at the time. I was about 14 years old when I started doing that. And that was the level of obsession I had. By the time I was in high school, when I was around 17 years old, I was selling those designs to ESR who published Dungeons and Dragons and other companies that publish similar games. Then I put myself through college doing that. I would hit the books and study for my college exams and then ultra late at night, I would sit down at the word processor and write the latest Dungeons and Dragons book or whatever I was working on. I continued doing that for a few years out of college just working as a freelance game designer, but that was my first step that led me into this much deeper career I had. I went from that to running a small paper and pencil game company. I ran the R&D effort for that. From there, I got into technology. I was one of those math kids, like many of us who love D&D were. So I always had an affinity for that. I found it pretty easy to make transition to computer games and video games. So I worked on the original launch of PlayStation. I worked in a video game unit at Viacom, as you mentioned. I was an executive producer there making all kinds of crazy things and so forth. And in fact, for a while, I took a little detour where I started to become at least as interested in the technology as I was in the gaming stuff. And so my career, I detoured for a while into just more of a traditional technology career. I spent many years at Microsoft in a role that we called platform strategy, which was this very heady, work with the executives on charting the future of Windows and things like that. It's funny when I tell people the story. It seems like a weird right turn to take. But what I found was my early experience as a game designer and working in a creative capacity, served me very well in corporate America. Pretty much whatever I found myself doing, so much of what I was doing at Microsoft and that platform strategy role, for instance was, here's a problem. Come up with a creative solution to the problem. It was much more similar to creating the stories and the characters and the things I used to do in game design than people realize. That was very helpful. To me, that detour of learning more about technology really helped me make better and more interesting video games. When I finally got back to games, it gave me a deeper understanding of what was possible in that realm. And also, my years in big time corporate America, fresh course in businesses and how they work, how to make a business operate at scale, which is very challenging, was very eye opening. I was successful in a bunch of those roles. And I found myself in a place where I was fortunate enough that I could do whatever I wanted. And what I really wanted to do was to go back and work on Dungeons and Dragons again. And so I found my way to Wizards of the Coast found myself in a role where I was heading up the D&D business for a few years. That was basically the story. Lizzie Mintus: What a dream. You're a dream hire for them. That's so exciting. It's really fun to be a recruiter and recruit for a company that have a product that people have so much love.

Ray Winninger: Oh, yes. It truly is not just a product, but a role. One of the things that I would often remind my teams in video games or on D&D, one of the little aphorisms I used to motivate and remind them is, if we were to take a walk down the streets, the local grade school, and we were to sit in a class fourth graders or fifth graders, and we were to do that classic thing of, what do you all want to be when you grow up? A percentage of those kids are going to say, I want to work in video games. That's what I really want to do. By the way, while that work I did at Microsoft, again, was very interesting. I found it interesting. I learned a lot from it. None of those kids are going to say, Oh, I want to be a backend SQL server programmer. That's a fine and noble thing to be and much more interesting than people realize, but there is something special that comes with having an opportunity to be in a role that's like being on a pro baseball team an actor in a big movie. It's just one of those things that people dream about and that's special. And, we in games, we have to keep that in mind. We have to remember that. We're fortunate that we get to work on that. Lizzie Mintus: I have a company that has a game they just released to their fans to start playing and give feedback on. And I went to the convention where they were releasing it. And it was amazing to see all of their fans there losing their minds to get to try the game. They're asking all the artists, all the developers to sign their devices, sign their headsets. Ray Winninger: Oh, yeah. Lizzie Mintus: I think that the team felt so sweet. They're like celebrities. When you take a step back and you do think about it, it is really amazing. And he makes something that so many people love, especially on D&D. I want to talk to you more about you were responsible for in the creation of Dungeons and Dragons products. What did you create and what can you say about the creation? Ray Winninger: Sure. Again, this is a continuation of back when I was in high school. I would write these as a high school kid, I was creating Dungeons and Dragons products. I did Adventures for Dungeons and Dragons, little stories to play, little add ons. I did that for several years, and so by the time I made my way to Wizards of the Coast, one of the things I think that was interesting about me stepping into that role, the gentleman I took over for there was a very smart, capable guy, but he was more a classic video game marketer. And when I stepped into the role, I was much more familiar with the product development process- what goes into making one of those books. His name's Nathan Stewart, by the way, he's at Blizzard now. Nathan, while he'd spent a lot of time on D&D, he wasn't quite as deep into it as I was all those years. Because I was a huge fan for decades. Because of that, I was able to very quickly build credibility with the key creatives on the team. The people were like, Ray can do it. And in fact, I did. I would jump into the trenches and be writing and editing books alongside them. And that served me really well in that role. I had a pretty strong understanding of what the market was looking for and what data to look at to get the right insights into where we should go, and what products we should make. So 1 of the things that I did quite a bit of in my role was really steer the ship on these are the products that we're going to go do. I wouldn't lay that down by Fiat. There's a process we went through a lot of folks had input into it, but that was 1 of the key things that I was responsible for was. Basically, all of the D&D products that came out , the last 3 years and will come out next year are things that I probably had a hand in at least conceptualizing or putting together the original ideas behind what it was going to be. Lizzie Mintus: Wow, what an impact. How did you balance honoring the traditions of the game versus introducing new elements that might entice new players? Ray Winninger: Yeah, that was one of the most challenging aspects of D&D. Next year will be D&D's 50th anniversary. A game that's been around for 50 years is pretty amazing. It's changed dramatically and I don't just mean it's changed because rules have changed over the years. Of course all that's happened, but the people who play D&D, the audience has changed dramatically. One of the things that I'm super passionate about D&D and games like D&D, I think D&D is not only a fun game and a really interesting creation, but I truly believe that D&D is a positive force in the world. So many of the people who find their way to D&D, it's through D&D that they meet their lifelong friends, their future husbands, wives, partners. All of that stuff. I've had countless, heartwarming encounters with people who've come to tell me, you just don't understand what this game did for me. I believe in this game deeply and one of the things that's happened over the last 10 or 20 years, especially is that the audience for it has grown tremendously not just in size, but the demographic has broadened. Back when I was a high school kid working on D&D, most of the people playing D&D were people like me. They were little suburban, young white boys playing D&D. It's just a cultural thing at the time, right? One of the things that we've seen in the broader culture, D&D, video games, comic books, all of that stuff, which all used to have that same sort of narrow demographic when I was a kid, they've all just blown up and expanded in every possible direction. D&D these days, the audience is pretty close to 50 50 male and female as an example, which is staggering considering where it started again. This isn't unique to D&D. You see the same thing. When I was a kid working on D&D, Marvel Comics was a very geeky little thing that had a very narrow demographic that was interested in. Of course, now it's the biggest entertainment juggernaut on the planet and everybody's interested in it to some extent. So that was very heartwarming to me to watch that happen. And I was very passionate about doing what we could to reinforce that. And not just myself, the whole team there, and as you hinted at, that had a big impact on how we thought about products, what products to make. Just the general tone and tenor of the game. It's funny as much as I've always love D&D, I never thought D&D could be even as remotely close to as successful as it actually is today. The number of people who play D&D regularly is right up there with the AAA gaming franchises that we're all aware of- the Halos and Assassin's Creed's and World of Warcraft, games like that. The audience for D&D is in the same ballpark as those games, which are obviously more mass marketing. I never thought D&D was capable of that, honestly, but it has hit those heights and it really was challenging to trade off. Okay, how do we keep what was great about the old game? How do we respect that tradition and carry it forward, let people discover it, and trade that off against tHese new people coming in with new ideas about how to play, which is fantastic. That was really interesting and that, in fact, is the challenge in D&D today. It's getting to the point where the audience is large enough that the old school approach to D&D product development of making one D&D book or one adventure that's aimed at the entire audience, is not working so much anymore. Because the audience is so big and so diverse and interested in so many different things that the challenge that's currently underway in the D&D business is trying to figure out how to segment that audience. We can't just make one product fits all anymore. We have to start looking at the various different groups inside of the D&D audiences, figuring out what they each want. Super fun. Lizzie Mintus: Yeah, like you touched on games are adapting. The audience is different and it's always a challenge when you have this product that's been successful for so long to keep things interesting. Would you say the biggest challenge around that is just adapting to your audience in ways you hadn't before? How can companies that have been around forever stay relevant? Ray Winninger: Having said the demographic is so wide and D&D is unlike other games, it's in some ways more accurate to describe D&D as a pile of suggestions for how to play a game rather than a game itself, because each group makes it their own thing and people play in very different styles. What I found to be very helpful in navigating that was, yes, there are all these people playing the game. They're getting all these very different things out of it, but there's a lot of commonality too. And so let's focus on that. Let's focus on those universal things that do appeal to everybody, that are at the root. We did a lot of soul searching about why do people play this game. What are the things that attract people to this game? My recommendation to people in a similar circumstance really deeply understand that. In my experience elsewhere, I found the answers to those questions weren't what you thought they were. What you think people are playing the game for isn't necessarily it. In fact, that's one of the ingredients. I mentioned D&D went through this huge growth spurt. And one of the factors that contributed to that was the Internet and online communities matured. It was possible for the first time for D&D designers to have a much deeper interaction with the audience, get a broad sampling of what people were doing and how they were playing. Interestingly enough, they were surprised by a lot of that. A lot of the things that game designers had assumed people wanted from D&D turns out, yeah, they're less interested in that and more interested in this other thing. I guess in terms of what can other companies take away, just know your audience. I know that sounds trite and it sounds obvious and simple, but it's so I've been in so many situations where the product development team doesn't really understand the audience or doesn't understand it the way they think they do. Lizzie Mintus: That might be true outside of games as well. Ray Winninger: Oh yeah, absolutely. Windows, I told you about being a platform strategist. I went through the era in which we were desperately trying to build a mobile business for Microsoft. Things like iPhone were coming in and frankly, what was going on was just at heart, we didn't understand the use cases. We didn't understand what people really wanted to do with a completely different idea about what people wanted to do with something like a mobile phone or a computer in their pocket. That's really the short story about what happened. Lizzie Mintus: What do you think makes people still want to play with old fashioned pen and paper when there's digital masterpieces. There's Skyrim, there's Baldur's Gate, it's still so popular. Ray Winninger: Yes. That's one of those things that we pondered at great length. And I think the answer is, when the game is taking place in your imagination, there are no limits. And when there are no limits, you can create in a way that you just can't in those other games. So my mantra about D&D was, it's about two things. People play it for two reasons. They want to be immersed in another world. They want to feel like they're somewhere else. They want to feel like they're someone else. And games like Baldur's Gate or Skyrim can do that. In some ways do it better because they can show you all the fancy visuals and everything.

But the second reason why people play D&D is they want to create. Everybody who plays D&D, every player starts with creating a character. And that character is yours. Unlike creating a character in a game like Skyrim or Baldur's Gate, there are no limits at all. You can be anything. You can look any way you want. You can have any personality you want. When you're talking to another character, you're not limited to those three dialogue choices. You can say and do anything and people's creative spirit really come out. And that's what's unique about D&D, like no other game can deliver that. I think that's what people respond to. I used to do a little demo for the executives where I would show them, let's understand the audience. One of the things I used to do is, back in pre Elon Musk Twitter, I would just search for Dungeons and Dragons. What's going on here? You would just scroll through the feed of things tagged Dungeons and Dragons, which you'd find endless posts of work- pictures that people drew, this is my character in all kinds of different styles, everything from funny little doodles to very professional artists painting their characters. This is the map of my world.

You just see all these things people were creating. One of the aphorisms I used to repeat all the time is that games like Skyrim and World of Warcraft, the major difference between those and D&D is that those games are about consuming content. In World of Warcraft, they'd create a new quest or a new raid, and there's new DLC for Baldur's Gate. Let's go play that. Whereas D&D was much more about creating content. It called upon the players to do that or gave them permission to do that. Magic happens there.

When I was running the D&D team, part of my tenure was during the whole covid. This little anecdote for me just illustrates the magic of D&D and what no other game can do anything like this. There was a group of kids in Australia that were all stuck inside and they were all sheltering in place. And there are actually some wildfires or something going on, which made it even worse for them.

And they started playing Dungeons and Dragons and the game was being run by this nine year old girl. She was running D&D for all the people who are sheltered with her, including her four year old sister had a character and all of that. And she came up with. This incredible story about the dragons are trying to control the climate and they're building this machine that's letting them change the weather. She actually built the machine out of Legos. As the kids were playing, they'd find new pieces of the machine and snap it on with the Legos. Her parents were recording this and putting it on social media. And I was just following this game Oh yes, this is it. The ideas that were coming out of her head were just amazing and just magical. Finally they wrapped up their game and it was actually the four year old who made the final role in the final confrontation that won, and these kids, it's like your team just won the world series. The reaction of these kids are just bouncing off the wall. We did it and we accomplished this big thing that we've been working on for years. It was just incredible. That was one of many aha moments for me. This is why people play this game.

You're never going to have this kind of experience with Skyrim. You're never going to have this amazing, creative little girl just pour her brain out and make this thing that engages everyone else and brings them along for the ride.

Lizzie Mintus: That's such a sweet story. Where do you see the future of tabletop? What is the future of tabletop?

Ray Winninger: Wizards is starting to play around with this a little bit. I think, increasingly the lines between traditional tabletop and these more digital experiences are going to start to get a lot blurrier. I think there's a real future in that.

When I say, technological or digital experience, I don't necessarily mean things like Skyrim or Baldur's Gate, although those are great too. I think there's a lot that technology can do to solve a bunch of the problems that have been around tabletop forever and also give players like that wonderful little girl in Australia, even more interesting tools and things they can use to build their stories and do their own things.

Ray Winninger: You see this now with Wizards. Wizards has an offering called D&D Beyond, which is a website, it's a digital tool you can use to create and manage your D&D characters. Very sort of simple idea, but powerful in the game. By the way, a huge percentage of D&D players now use this tool, which makes sense, right? Because if you think about it, in the 21st century, why are we still sitting down, adding numbers by hand on a piece of paper and erasing numbers over and over again? Some of these more mundane bookkeeping tasks that go along with D&D, why aren't we just offloading that to the text? We can focus on the cool dragon weather changing story and that sort of thing. So I think there's increasingly going to be more of that, and the worlds are going to merge.

You're going to start to see more sort of hybrid experiences. Maybe even it gets to the point where games like Skyrim merge with tabletop in some ways that you can imagine playing a game like The Avengers, for instance. We all come together at the tabletop and have an adventure together. But when we part ways, I go back and have my own adventures in a game like Skyrim. I think you'll start to see a lot of interesting things there.

Of course, one of the big pieces of technology that's just arriving on the scene that has the opportunity to really dramatically transform D&D is AI. I've seen some demos of AI running D&D that are way more impressive than I would have expected even at this early stage. The future of tabletop, in my mind, is what D&D has always been, a bunch of tools that people can put together to make the game exactly what they want. Only now, a lot more of those tools are going to be technological in nature. And we can have games that sometimes I play by myself. Sometimes we play together as a group.

Lizzie Mintus: Happy you touched on AI. It's AI is the new Metaverse crypto NFT. There are many use cases. How do you think people can stay ahead of the curve? Technology is evolving so quickly and it's an adapt or die situation.

Ray Winninger: Yeah, it's fascinating, right? That's always the challenge and. The advice that I would offer there is, I'm not exactly sure how this works, but for some reason, young people can stay on top of that stuff.

Just have more facility to stay on top of that stuff than those of us who've been around for a while. Maybe it's just because we've all internalized all these rules of how things are supposed to work that they haven't internalized yet, and therefore they're more open to new ways of thinking or new ways of doing things.

I think the best way I found to stay on top of the latest tech is, just get more young people in the mix.

Lizzie Mintus: And on from a hiring standpoint, you can also find people from all kinds of different backgrounds and train them and bring them into your culture. And that's really an amazing strategy to get people who don't look just like you on your team.

Ray Winninger: Absolutely. There's no substitute course for when you hire, you're looking for somebody with a proven track record and exactly what it is you're looking for. I've seen so many cases and my own story that I told earlier, I found myself in positions that on paper, you never in a million. Let's put this game designer on the future of windows and what windows shouldlook like. And I was very successful at that. Again, I'm not suggesting something as radical as throw away the conventional wisdom because there's no substitute for somebody who knows how to do exactly what you want. But my career, I've learned that you can't be afraid to take a chance on people sometimes.

Sometimes it's really good to throw a few people in the mix that they've never made a game before at all. They're very smart people who know a lot about something like AI. That can really be a force multiplier sometimes. I've seen that a lot.

Lizzie Mintus: Yeah, I would agree. To figure out what your values are and what characteristics you need in people and hire against those. I have so many companies who are like, this person is not as proficient in XYZ tool. And I do understand there's different stages of your games. And sometimes you're about to ship and you need someone who can plug and play. And that's okay. But if you're not, like you said, there are a lot of people you could take a chance on who shine.

Ray Winninger: Yep. Definitely. I've seen many examples of that. At one point when I was at Wizards, we brought in somebody who traditional software background, never worked on games before, was more of a project management type and just revolutionized. It was much easier for this project management expert to Grok what went into making a game and apply the skills and the knowledge that they have, then the reverse would have been.

I, myself, was at Microsoft for 13, 14 years. For a while there, I took over product management for Internet Explorer when it was at its height. We had about a billion and a half users daily on Internet Explorer. We shipped updates to Internet Explorer 40 times a year in 171 languages. I touched on that earlier that I was fortunate enough to see how to operate something at scale. I was in the mix and in the middle of operating things at scale larger than almost any conceivable game would be operating at. And that just paid such dividends down the road. And so again, there are people who at first blush, may never had made a game before, but have some pretty interesting skills and can really bring a lot to the team.

Lizzie Mintus: If you are that person and you've been in a different role and you get this role in a new area that you aren't necessarily the expert in, do you have any stories about combating imposter syndrome, finding a mentor, figuring out how to succeed in that role?

Ray Winninger: Yeah. Obviously mentorship is great and is. Almost every successful person I've met has had a mentor, whether a formal or informal. That sort of relationship is critical. I urge everyone and at all levels. I used to work quite a bit with the senior Microsoft execs, people like Steve Ballmer had people that they relied on that gave them advice. So I certainly recommend that.

It's interesting that you raise imposter syndrome because, we all feel that in different things, but I think one of those ingredients for success that I've seen is, people who've been successful are the people who just, hate to say it, but just sort of power through that. The people who aren't afraid of making a mistake, aren't afraid of looking foolish, because you never really look foolish. So the advice I have for people there is really that. Everybody around you knows less than you think they do as well. And don't be afraid of making mistakes. Don't be afraid of asking a question that you think might make you look foolish. You're going to exit that phase much faster than you think you are. In a high paced, fast paced, dynamic environment like gaming, a month in the trenches, you're gonna know what you're doing.

Lizzie Mintus: You'll have to. You'll learn a ton. I was very unsure when I started the podcast and nervous. And now I don't know how many I've recorded, but eventually it does seem really natural and you just have to force yourself to do that hard thing.

Think back at all the things that you've done. There's a phase where I'm unsure. This makes me a little bit nervous. I don't fully know what I'm doing, but like you said, just launching into it.

Ray Winninger: It goes back to that experience I had as a 14 year old trying to write the Dungeons and Dragons things. And in a way, I was so fortunate to have gone through that because when you're 14, you don't think about things like imposter syndrome. I just want to do this thing. You haven't yet been trained to believe, what makes you think you can do this. You don't think that way yet. So you just dive into it and you just do it.

It's funny, as a game designer, those early years were very prolific for me and then I started to slow down a little bit and I realized I was slowing down because I started to become much more conscious of, is this really good enough? Am I really doing a good enough job on this? There's some value in that too. You should always be pushing yourself and trying harder, but wow, I never would have gotten started if I had started with that attitude. It was just like, of course I can do this. It's just words on a page. I'll figure out how to write it.

And again, I know people who are in that situation, I know it's just super easy to say just don't worry about that. But really, honestly, I think that's the best advice I can offer. just push ahead. If you make a mistake, you make a mistake. By the way, this is a mental thing I would always do to get over these is, I would always try to understand what's the worst case? What's the worst possible thing that could happen?

The worst possible thing that can happen is, you just aren't right for this job. You just can't do it. Then you'll go get another job and you'll do something else. Honestly. In fact, getting to the point where you understand that has tremendous value. Like getting through and realizing, you know what? Not a game designer. Maybe I should be a producer instead. That has tremendous value. So that's the worst thing that can happen.

Lizzie Mintus: I think about that, too. What are the different worst case scenarios and outcomes and how will I handle those? And then once you know, I think it's just a human thing. Once you can envision all those scenarios, then you can move forward. Ray Winninger: Yeah. For me, it was always, that's not so bad. I could live with that.

Lizzie Mintus: Yeah, you tried and you learned and you could go do something else.

Ray Winninger: And it gets you to where you really should be faster. It helps you understand sooner. That was a very difficult lesson for me to learn as a manager, but a powerful lesson. When I started managing teams and managing other people is, sometimes when you're managing someone and they're just not right for whatever it is, they should be doing something else. You're not doing them any favors by keeping them. You're really not.

I know that sounds bad. And if you've never been in that position, I was. Oh God, I hated being in that position early on. But I learned fairly quickly that the best thing you can do is help them get to a place where they belong. Where they will shine and they will be successful. Maybe that's not in their current role. Maybe that's not in their current company, but that's the best thing you can do for somebody, honestly.

Lizzie Mintus: I would agree with that. And they will be happier eventually too. I've heard many stories of people being let go. And obviously you have a shock and hopefully it's not a shock. Hopefully, it's been coming because you've had some precursor conversations, but then having people thank you later because they found the right thing.

Ray Winninger: Yeah, that's what happened to me early on. I was going to do everything in the world to try to keep you, even past the point where it's clear, this just isn't working well. And yes, and I fortunately had the experience early on of, I'm just so much happy. Thank you because it was really the right thing to do for me to move into something else.

By the way, people listening to this, the situations we're talking about are extremely rare in my experience as well. Don't sweat this. It's important to keep that context in mind. But again, not just as a manager, but as somebody working on this stuff. The best favor you can do for yourself is admit it's not going well for whatever reason. That's the best thing you can do for yourself.

And I know that it's never easy switching roles or switching jobs and there's a lot that goes along with that, but trust me, you will be happier.

Lizzie Mintus: Yes, I had a recent experience where I had a candidate and they really wanted to quit. They were unhappy and then their company came back with a counteroffer. And there's some stats like 90 percent of the time if you accept a counteroffer, you're going to leave within six months. I think it's 90 percent. It's really high. And then we had a conversation a while later and the persons said, I should have left, but I stayed. So I think it's also important to be honest with yourself, when things aren't right, or when you get laid off. Obviously there's a lot of emotions and maybe you're in a terrible scenario on a visa, or financially, but there is a lot of opportunity when Things shift, if you can see it.

Ray Winninger: That's right.

Lizzie Mintus: I saw you worked for Mitch at Harebrained Schemes. Mitch is hilarious and I will have him on my podcast.

Ray Winninger: He just mentioned meeting you the other night. I was with Mitch. I said, I think that's the podcast I'm doing this week. Mitch and I are very old friends. I brought Mitch into the game industry way back when I was still on tabletop. He and I went in the video game industry. We did a startup together in video games, both of us. It was our first video game role, actually.

Lizzie Mintus: I didn't know that he's hilarious and he has a comedian background.

Ray Winninger: That's true.

Lizzie Mintus: You worked there and you worked at HTC on five and both of them on go to market. The big question- what should people consider when they're building out a go to market strategy?

Ray Winninger: It's a huge question, obviously, because it differs so much by the product and all of that stuff. I think, the things that, that I would call out that I think are universal in my experience are, again, I can't stress enough, know the audience. Get the audience using the product in some way as quickly as you can, and then keep a very open mind as you watch what they do with it and how they use it. Because more often than not, you're surprised. I've been fortunate enough, I've had a chance to work on some really innovative. Things and things that are like very different and particularly with that sort of stuff. Slack the tool that we all use as a messaging system. I don't know if you know this, but Slack was actually originally designed to be part of a video game. It was the chat system for a video game and the developers found that the game's not so great, but wow, everybody loves that chat thing that we've built. That's the thing we should be focusing on. We're doing some really interesting stuff with that.

That sort of story is not uncommon at all. So get people using the product as soon as you can. Keep an open mind when you see what people are doing with it, because everything is going to flow from that. Again, understanding the customer. Understanding the business that you're really in. By the way, that's another very common issue that I see is people don't quite understand the business that they're really in. Dungeons and Dragons- I mentioned if you look at that from the outside and you're not terribly familiar with how that works, and we have this issue with various leaders at Wizards, the facile look at Dungeons and Dragons is, oh, we create these stories and these characters that people play with. And they go have all these adventures. Which is true on the surface, but really the business you're in, I believe the data the conclusions I ultimately drew is, that's not really the business you're in. You're really in the business of giving people the tools that they can use to create their own stories and adventures. Don't think of what you're doing is creating a story. Think of it as creating a tool kit that you're handing someone. They're going to make the story out of the pieces you give them. That's a huge conceptual difference, and it really changed the way we thought about products when we started thinking about it that way.

So understand what business you're really in, understand, the customer and again, this is one of those things that seems obvious, but I've seen so many people fail. Set very modest goals for yourself at first, very modest, achievable goals. It is super, super common for people to build models, to build, go to market plans that just. They just call for crazy levels of success early. That happens almost never. That was one of the issues we had with Vibe, with the VR headset is, frankly, the expectations were way out of whack. It's super cool product, super cool technology. We're not going to sell more of these than Microsoft sells X boxes in two year. That's just not going to happen. CDs, compact discs, maybe people in the audience don't even remember those anymore at some point, but compact discs were the primary way music was sold for many years. Compact discs were around for 12 years before they really caught on and really became a consumer thing that were selling a lot. That curve is actually not that uncommon in technology. HD televisions were around for almost 10 years before they started to really get traction in homes.

You see this over and over again. Particularly if you're doing something innovative, in your go to market, build a plan and set modest goals for yourself. And be okay with that.

Lizzie Mintus: Would you say that they really take off when they find product market fit. What is the inflection point and how can you, yeah,

Ray Winninger: Product market fit, absolutely. That's of course what it's all about. But we all know the crazy success stories, right? We all know Facebook. They had a billion users and 6 years or whatever it is. The iPhone. We all know those. Those are exceptionally rare. Those stories where something just hits the market and just immediately becomes a dominant product. Google search engine. There's a handful of things like that. The vast majority of things build their market slowly over time. This is why, by the way, you look at the innovative products that come out- Facebook, things like that. This is why they tend to come from small companies or startups. It's much more rare that you'll see a giant company a company like Microsoft innovates and ships this brand new crazy thing. It's because a product that's gonna take 10 years to build a market. They don't have the patience for that. With the dynamics of how large their companies are and that sort of thing, it's rare that you'll find. Amazon is actually better at that than many companies, but it's rare that you'll find, yep, we know this is going to be a small thing for 10 years and we're going to stick with it. That's why those huge mega successes tend to come from little startups.

The iPhone from Apple, people don't really remember this, but pre iPhone, Apple wasn't that big or dominant of a company. About five years prior to the iPhone, Apple was teetering on the brink of bankruptcy and going out of business. The big, massive things tend to come from small companies. Lizzie Mintus: Yeah, and then the big companies acquire them.

Ray Winninger: Yes, exactly. That's right.

Lizzie Mintus: And sometimes it goes well. Sometimes it doesn't.

Ray Winninger: That is correct. Yes.

Lizzie Mintus: I have one last question inspired from Women in Games International, which is a fantastic organization. Joni was on the podcast, but they have a whole program that's built around. I wish I had known X at Y stage of my career. Good cheat code for the next generation. What cheat codes can you share? What do you wish you knew when you started? Ray Winninger: Yeah. What do I wish I knew when I started? Touched on some of it earlier- just don't be afraid. Be humble and respectful,. Don't be afraid to push yourself and to challenge yourself. Lots of people are much more capable than they think they are. Don't be afraid to push yourself to take some risks do that. That's 1 for sure.

The 2nd one is- there are basically two templates I've seen for very successful people, and it took me a while to understand this and understand that both of these paths can work. There is a particular branch of people who are very successful who, they're planners, they plan out their, they know exactly what I want to do is I want to run a game studio someday. It's probably going to take me 10 years to run a game studio. So in order to run a game studio, I need to first be in this role for a couple of years, and then I need to do this for a couple of years or whatever. That is one path to success. And I know many. Very famous, very successful people who've done that.

However, there's another path, which is leave yourself open to experiencing things, right? There are a lot of people who find that they don't understand what they want to do as well as they think they do, right? In my career, I found myself working on things I never in a million years would have thought I would work on this. But again, I found them very interesting and I learned a lot from them.

I was not a planner as it turned out. But, I raise this and answer your question because that is an equally valid path. Advice I often given people when they don't know what to do next, or they've got a couple of maybe a couple of job offers. Advice I've often given people is, forget about the job for a minute. By the way, in my experience, a lot of times the jobs that you think are going to be super glamorous and super exciting turn out not to be. And the inverse is also true.

Earlier, I took a shot at the SQL server backend program. No fourth grader says, I want to be a SQL server backend programmer. That's a very interesting thing. And a lot of people find that they're super passionate about that. So my advice is often forget about the job for a second, the people, the person who's going to be your boss, which one of the two do you like better, you get along with more, you think is more interesting to you. Because by the way, one of those, one of those pearls of wisdom I can offer people things that I've learned over 30 years is, the single factor that's most likely to determine whether you're happy or not at work is how you get along with your boss. Do you like your boss? Does your boss like you? Do you like the people you work with? That's often way more important than, I really wanted to do narrative design, but couldn't do narrative design. So I'm a associate. Who are the people you're working with? Do you have somebody who you'd like and who believes in you? So that's the other thing that I would offer.

The thing I urge everybody particularly interested in getting into games and particularly, but not exclusively people who want to work in the creative end of games- And this isn't something that I wish I knew because again, this is how I've blundered into things, but: make games. Start making games. We're in a world now where it is very easy for a high school kid. I talked about my manual typewriter and all that stuff. A high school kid can go download Unity and can start watching tutorial videos and can start making simple games. It is well within your capability to do this. There's not any big expense or anything that you have to lay out to do this. Start making games, make mods for games that are out there. Just start making things.

If you want to get into games, any aspect of games, but particularly creative, even if you want to be a producer or whatever, do this. Push yourself a little bit. That is by far the best way to A, learn what you really interested in, what you really want to do. And B, that is by far the best and easiest path to get the attention of a potential employer as somebody who has no experience yet, as somebody who's to break into the business. You got something you can show. I made this little thing in unity. I wrote this little text adventure or whatever, just anything that you can show.

In fact, at a certain level, I think that's almost starting to become almost a requirement for entry level.

Lizzie Mintus: It is because there's so many applicants and there are not entry level jobs. It is an issue, but if you can find a community, get involved with the community, chat with people on discord, ask for them to be a mentor, create something yourself. I had Tim from Global Game Jam and Seattle Indies who shared, go to the meetups. Go to a game jam. Get involved and show that you care.

Ray Winninger: Yes, meet people. Build things and meet people. The tools are out there now. Just start and that will take you a long way.

Lizzie Mintus: You might be really successful at it too. I had Jenny Xu on my podcast and when she was 14, she had one of the top mobile games up there with the Sims that she had created herself. So you never know.

Ray Winninger: It is awesome. Exactly. And that's great. But even if you're not successful , you're going to learn so much, not just about the games, but about yourself and what you're really interested in. Lizzie Mintus: But when you explain what you've done, I think a big pitfall that more junior people have, sometimes they do these little bubbles on their resume and they claim that they're the expert because that's their expertise in X. So I think you also have to have some humble pie and share that this is what I've done so far. I acknowledge that I have not created a game in a production environment. Ray Winninger: Yes, without a doubt. Of course. By the way, if you really get interested in this and you start pushing and you start making things and you start asking, how do you go to the next level on this? How do you make a game even more complex than this? I actually think that's the sort of thing you learn through doing that as well. Yes, I've made this little thing in Unity. It is nowhere near Blizzard is. But I think pushing yourself is actually sometimes the fastest way to learn what you don't know as well. Lizzie Mintus: And you don't have to work at Blizzard to be successful.

Ray Winninger: No, you do not.

Lizzie Mintus: At the beginning of your career, you can work at a startup, you will learn a ton. And Blizzard is a wonderful, classic, iconic company, but it's also not for everybody. People get tied up and working for XYZ, but you can learn things from all different places. Your career path will not be a straight line and that's okay.

Ray Winninger: That is an excellent point as well. And I've seen that. I've seen people obsessed with, I really want to go work on D&D. Or I love Fortnight. I really want to get in there. That's great. But again, as you say, you're going to have a long career. You have plenty of opportunities to do a lot of things. Just get yourself started somewhere.

Lizzie Mintus: Yes. Look at you. I love that your last role was your high school dream, but it took a while, right? Ray Winninger: Oh, yeah.

Lizzie Mintus: Lots in between. We've been talking to Ray Wininger, former executive producer at Wizards of the Coast. Ray, where can people go to learn more about you or contact you?

Ray Winninger: I am on Twitter at WiningerR. I guess they call it X these days. I'm at all the usual social media sites. I never do anything clever with a handle. I'm always under my name. Please feel free to look me up. Reach out to me. If I can give you any advice, I'm happy to do that.

Lizzie Mintus: Thank you.

Ray Winninger: Thank you. Thanks so much for listening to the show this week. To catch all the latest from Here's Waldo, you can follow us on LinkedIn. Be sure to click subscribe to get future episodes. We'll see you next time.