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Charlie Ninegar, COO of DSS Games, on Getting People Off Their Phones and Growing Against the Grain

AI for Business Leaders · 2026-03-28 · 16 min

0:00--:--

Key moments - from our scoring

Substance score

55 / 100

Five dimensions, 20 points each

Insight Density11 / 20
Originality9 / 20
Guest Caliber13 / 20
Specificity & Evidence12 / 20
Conversational Craft10 / 20

DSS Games manufactures tabletop card games designed to disconnect people from their phones and foster in-person engagement. While the broader game category contracted a few percentage points in 2025, DSS Games captured market share through differentiated content strategy and brand positioning. Charlie Ninegar explains that despite the threat of AI-generated games flooding the market, the company maintains competitive advantage via high-quality content, consistent brand values, and network effects from word-of-mouth adoption. On the AI front, DSS Games uses custom GPTs internally to empower teams across HR, finance, supply chain, and marketing - Charlie himself built ten GPTs to optimize his generalist COO role. The company deliberately avoids using AI for game design, art, or core creative output, viewing those as critical to brand differentiation. However, Ninegar acknowledges this stance will likely evolve as AI image and video generation improves, particularly for tasks like social media ad testing and packaging mockups. The episode covers content strategy (primarily short-form TikTok and Instagram videos), change management around AI adoption across a 25-person team, and the broader question of how consumer goods companies should adopt AI responsibly while preserving what makes them distinctive.

Key takeaways

  • →DSS Games grew market share while the overall tabletop game category shrank by using consistent, high-quality organic content - particularly short-form video on TikTok - rather than volume-based publishing.
  • →AI tools like custom GPTs can dramatically increase productivity for generalist leaders when trained on company-specific history and knowledge, freeing up time for creative and strategic work rather than replacing it.
  • →Despite team reticence about AI adoption based on environmental and political concerns, educating staff on responsible use and offering multiple LLM options increases adoption among power users and supports skill development.
  • →AI-generated content for game design and art remains off-limits at DSS Games due to brand protection, but the company expects to adopt AI tools for social media ad testing and packaging composition within 1-2 years as quality improves.
  • →Carving out 10% of employee time for learning, experimentation, and agent-building creates a culture where staff develop skills faster and feel supported for their next career move, reducing burnout from pure execution work.

In this episode

  1. 1Introduction to DSS Games and Mission to Get People Off Their Phones
  2. 2Growth Strategy and Market Share Gains During Category Decline
  3. 3Content Creation and Social Media Strategy
  4. 4AI Implementation and Team Empowerment
  5. 5Custom GPTs and Internal Process Improvements
  6. 6AI-Generated Content and Future Vision
  7. 7Community Learning and Best Practices Sharing
  8. 8The Ideal Game: Conversation Starters and Human Connection

Mentioned

DSS GamesChatGPTTikTokOpenAIGeminiClaudeShopifyTargetInstagramCharlie Ninegar

Guests

Charlie Ninegar

Topics in this episode

Custom GPTsBrand differentiationAI-generated contentTikTok marketingMarket share growthLLM toolsDSS GamesTabletop card gamesShort-form video strategyConsumer goods AI adoption

Questions this episode answers

How is DSS Games growing when the tabletop game category is shrinking?

DSS Games is gaining market share through high-quality organic content (primarily short-form TikTok and Instagram video), strong brand positioning that differentiates their simple games, and word-of-mouth network effects. They've shifted from publishing 1,200+ videos annually to fewer, more targeted videos with higher engagement per piece.

What AI tools is DSS Games currently using and how?

The company uses custom GPTs to help employees with task-specific work across HR, finance, supply chain, and marketing. Charlie has built ten GPTs tailored to his COO role. They deliberately avoid using AI for game design, art, and core product creative work to protect brand quality.

Does DSS Games plan to use AI-generated content for game design and marketing?

Not currently - the company keeps creative output in-house to maintain brand differentiation. However, Charlie expects this will change within 1-2 years for lower-stakes tasks like social media ad variations and packaging mockups as AI image and video quality improves.

How is DSS Games handling employee resistance to AI adoption?

The company educates staff on responsible AI use, addresses concerns about environmental and political impacts, and offers multiple LLM options so employees can choose tools they're comfortable with. Leadership also allocates 10% of time for learning and experimentation.

What does Charlie Ninegar consider overhyped about AI in consumer goods?

He believes the hype around AI agents for personal and business productivity is premature - the market is still mostly using AI one or two steps above basic search replacement, and truly functional agents are not yet showing up meaningfully in most workflows.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

11 / 20

The episode contains some useful tactical insights about content strategy (1-in-40 going viral declining to 1-in-70, shift from volume to quality), custom GPT creation for COO work, and AI adoption change management. However, much of the discussion is surface-level (AI is good, it's getting better, use it responsibly) and relies on general platitudes about empowering teams and clearing busywork. The concrete takeaways are limited and somewhat obvious for experienced B2B operators.

We were able to grow. I mean, we stole market share. And I think it's because of the quality of content we've been putting out.
we're getting more views per video. So we are growing our impact and our reach. But it's, it's gotta be a more considered approach rather than sort of a spring

Originality

9 / 20

The perspective is reasonably fresh for a non-tech business (games, not SaaS), and the honesty about team reticence to AI adoption is noteworthy. However, the core frameworks are conventional: custom GPTs for productivity, clearing busywork, learning from peers, and the familiar "today's AI is the worst version" argument. The guest doesn't challenge existing thinking or offer contrarian takes beyond acknowledging that not everyone in tech is as far ahead as assumed.

You could be made to feel like if you're not living in an AI echo chamber all day long, that you're 10 miles behind the front of the pack. I'm not sure that that's true.
If it's bad at it today, it's going to be pretty dang good at it at the next generation.

Guest Caliber

13 / 20

Charlie is a genuine operating COO running a real, growing business in a niche market ($20 card games, 25 employees, measurable growth while category shrank). He has P&L responsibility and makes actual decisions about AI adoption, team management, and product strategy. However, his scale is modest and he lacks enterprise/large-scale operator experience, limiting his caliber relative to C-suite leaders running larger organizations. He is credible but not exceptionally senior.

I'm Charlie. I'm uh, the COO of a company called DSS Games. Our company makes tabletop card games
I'm a sort of a generalist. Right. My role is overseas hr, finance, supply chain, production, marketing.

Specificity & Evidence

12 / 20

The episode provides concrete metrics (1-in-40 viral rate dropping to 1-in-70, 1200 videos published in first year, 10 custom GPTs built, ~25 employees, $20 price point, category shrinkage of a few percentage points) and specific product details (TikTok/Instagram focus, conversation starter card games). However, many claims lack supporting data: no revenue figures, no CAC numbers, no specifics on which GPT use cases generated ROI, and vague discussion of 'quality content' without defining or measuring it.

Back then, 1 in 40 would go viral and we'd see sales lists and then it became 1 in 70.
That year we published something like 1200 to companies.

Conversational Craft

10 / 20

The host asks reasonable open-ended questions and follows up on AI adoption and content strategy, but rarely pushes back or challenges claims. When Charlie makes strong assertions (AI-generated content will have to change, today's AI is worst version), the host nods along rather than probing for evidence or exploring counterarguments. The conversation is friendly but lacks the intellectual rigor of a great interview. The personal questions about game preferences are charming but low-substance.

Yeah, no, uh, that's what this podcast is about as well. Just to demystify AI.
Right, Right. It's definitely the change management for the employees of more forward thinking will be more innovative empower users with LLMs.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B73%
  • Speaker A27%

Most-used words

content15game14games12feel8share7team7trying6tools6interesting6back6category6start5young5tool5play5social5

Episode notes

Charlie Ninegar is the COO of DSS Games, a fast-growing tabletop card games company on a mission to get people off their phones and back around the table. In this episode, recorded live at eTail Palm Springs, we dig into how DSS Games stole market share while their category actually shrank through relentless content quality, brand discipline, and a team-first approach to AI adoption. Topics covered: Growing in a shrinking market through content-first strategy TikTok-first organic content: from 1,200 videos/year to fewer but higher-impact Custom GPTs as a practical first step for AI adoption Change management: why some young employees resist AI (and what to do about it) The coming shift from "no AI in creative" to AI-assisted brand content Why the AI arms race looks different outside the tech bubble Sign up at for early access to episodes, frameworks, and insights we don't publish anywhere else.

Full transcript

16 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Welcome to AI for business leaders podcast. Welcome to another episode of uh, the street format at etl. Uh, right now I'm speaking with Charlie from DSS Games and really happy to have you. We spoke quite a bit about some of the AI adoptions within the companies as well as what he's seeing in the future. So can you just start off by giving us a little 30 second pitch of who you are, what you do and your background?

Speaker B: Yeah. I'm Charlie. I'm uh, the COO of a company called DSS Games. Our company makes tabletop card games, stuff that is meant to get you off your phone and engage with your family or your friends.

Speaker A: Anti AI is that way.

Speaker B: Anti AI at least the product that is really our mission is to try and get you to engage because we're all stuck in these devices all day. So my role as COO is I'm sort of a general manager. I'm supporting every division of the business, more or less. And we're a young company, we're a growth company. Uh, we operate in a pretty small niche, but we're a big player in that niche and growing fast, fast. And we're just trying to kind of catch up to the potential the business has. And the last few years have been great. So. So uh, yeah, that's why I'm here and here at the show to just see what's the state of the state, what's going on out there, what do we not know that we need to know and how are people using tools like various AI models, agents, effectively.

Speaker A: Yeah, no, uh, that's what this podcast is about as well. Just to demystify AI. All the thing goes, uh, something that we were talking about, things will be interesting is that, you know, the past 12 to 18 months is probably as 12, 18 months probably hasn't been the easiest for a lot of retailers. Also consumer brands, tariffs, market conditions, AI, on and on and on. And what's interesting is that you just mentioned you guys are more than growth company. It's been doing really well. Like you see that's more healthy trajectory. Yeah. Can you share a little bit about like. Yeah, a little bit story, half of that, like where it was, what did you guys do and how are you guys able to consistently grow?

Speaker B: Sure. Right. So we're at the start of 26 and when we look back at 25, what happened and if I talk about our category specifically and we get a little access to category, um, information, the consumer feels a little stressed. They bought less units, they paid more for em and ultimately the category didn't grow. It shrunk a few percentage points. That's the broader, you know, gain category. In that category though, we were able to grow. I mean, we stole market share. And I think it's because of the quality of content we've been putting out. Uh, we've done a good job of really identifying and understanding kind of, you know, the mission, vision, values of the business, who we are and how we're different in a crowded space. Because our games are very simple. And what's interesting is there's a threat to this category and the incumbents in it, because it's not that hard. You could use an AI tool to spin up a game real quick, right? If you spin up the marketing images you need, you could probably figure out how to print it and put it on the market pretty easy. It could hit the marketplace and we kind of see that starting to happen. And I think the way we're raising, rising our brand and business above the noise is by having really good quality content, not compromising on our, our values and visions for what the product looks like. And then we need sort of that, that amplifying network effect. If you play the game with your family, they love it. Maybe one of your kids goes over to a friend's house as we play this game, we love it. Or you know, if we play with a set of friends. And that's really what it takes. Cause our games are very, ah, I think very value oriented. They cost 20 bucks or less. So we need to sell a lot of them for it to make a difference and we really need to sell a lot of them. That game's got to cat. So that's so sigua interesting.

Speaker A: You talk, you say content, right? When you say content, do you mean like social media content, blog content, any other sort of mediums, from text to image to videos and all types of content?

Speaker B: A little bit of everything. We spend a lot of time making organic content for social, specifically TikTok, I'll say Instagram, but primarily TikTok first. And then as you know, anybody who manages a catalog, you've got to have a lot of images and for all your product detail pages, whether they're on a marketplace site or on our, um, own, you know, fully owned domain. It's like we need a lot of marketing assets, but mostly it is about video, social content. That's where we spend a lot of time filming and we have a small but mighty team who makes sure we're pumping out a lot of content. You know, I started with a company Three years ago, I think that year we published something like 1200 to companies.

Speaker A: Wow.

Speaker B: We've actually at the time all made

Speaker A: in apps or, uh, some of them

Speaker B: utc, no ugc or. We would have, we'd have, we, we'd have, you know, paid people who were making short little videos, like, like very short videos. Maybe you just saw a card of ours from a game flip over and it was funny. Back then, 1 in 40 would go viral and we'd see sales lists and then it became 1 in 70. And I think that was because it was getting noisier and noisier. And so today we're actually publishing less videos than ever. Still a lot. And luckily for us, we're getting more views per video. So we are growing our impact and our reach. But it's, it's gotta be a more considered approach rather than sort of a spring, so that we're just sort of always, always iterating on what's working and considering what are we not doing. But it's very much, we're focused on that social media, short video format.

Speaker A: Right. More ideas, to be honest. Right. That makes a lot of sense, um, to AI. Right. We talked a little bit about that. Uh, maybe just to start out sharing a little bit. What are you guys doing with AI right now? And perhaps what do you feel like is the biggest leverage for your business and what's overhyped?

Speaker B: What we're not doing is asking AI to give us game content or, you know, art from the outside of our bots. We're keeping that very, very much focused in house. What we're doing with AI is mostly trying to empower our teams to use our company to use it. We want to make it available, we want it to be used responsibly. And we see it as a very powerful tool that should be used in pretty much every aspect of the business. And what's interesting is we have a young team. I'm, I'm in my mid-40s and most of the company is about 20 years younger than me, I would say.

Speaker A: Right.

Speaker B: 15. And some people are power users and they're using AI tools every hour. Many are using it at least every day or every week, but some aren't using it and some are very reticent. And that kind of surprised me to see how much reticence a few or few people have. And I understand it. There's environmental concerns. Right. Political concerns, and there are other concerns. So we're just trying to do our best to educate our staff about, uh, how we feel it should be used appropriately and that we do feel it is important to use in the right space and then try and make them comfortable with the tools they have available. So if they don't like this LLM uh model for one reason do we have another that we know is quality. We know can protect our proprietary data when we put it in but still then we can empower our team to go do whatever they need to do and hopefully they're clearing out. We want them clearing out the busy work so they can focus on the more creative stuff, the more strategic stuff and that's the hope is that you just move a little faster with a tool like an AI.

Speaker A: Right, Right. It's definitely the change management for the employees of more forward thinking will be more innovative empower users with LLMs. Uh, is there any sort of process like you can share that's been working out well for the company.

Speaker B: We've made a custom few custom GPTs and this was fun. I never touched a GPT and made a custom one. So we have a PERTH reading GPT that we can share around the company and Now I have 10 GPTs that I've made to help me And I'm a sort of a generalist. Right. My role is overseas hr, finance, supply chain, production, marketing. All things in my career I didn't spend tons of time on. So it's been a very helpful tool to have an LLM whether it's like a project that has a bunch of history stored in it or a GBT that's been finely tuned to help me work my way through my work. That's how I'm using it. And I'd say other power users are sort of the same saying we're trying to get. We're only really one step above uh, I think using the LLM to replace a Google search maybe two steps above that. I don't see a lot of agents yet showing up in our, in our lives. I'm looking for the point when an agent can help me with my personal and business life and so I'm playing with it. Yeah and the most important thing we're trying to do is clear time. I don't want my employees and staff feeling like a hundred percent of their time is consumed just doing the day to day work. I want them to have at least 10% to go to a conference to play, try something, try to build an agent and maybe it's going to not work the first time or the second or third. Eventually it will work and then I start using it. I'll Never have to build that one again. I'll move on to the next thing.

Speaker A: What I've seen also just my tabs with Shopify when it comes to change management. Also new job shares and you know, boards and so on. A lot of times is that that where you have the high performers who are really excited because you're potentially carving out time for that to develop their career because they understand no matter what AI is here and it's going to be here. So either try to learn or you don't. You may only uh, get but behalf.

Speaker B: Yeah I feel like if we've done our job and I've specifically done mine, I want my. We're about 25 people at the company. When growing we're hiring. You know, I want. Not everyone's going to be there their whole life. I want them to say they came in at this level in their career, they learned a bunch, they accelerated and they come out at this level and help them get that next amazing job. As though we're really trying to empower our team whether it's with AI or just to grow mature with the company. Because we're growing quickly too. Um, so that's been fun part of the process and I do feel like giving uh people time to not be bogged down just a hundred percent of the time on just day to day work that sort of like is by Rogue. You gotta give them space to like stretch their legs and fail 100%.

Speaker A: That's surround leadership. Yeah, by exactly. Uh, you had mentioned about just the importance of content and obviously a win a lot of talks when it comes to AI generated content, whether that's text or image or video. What's your view on that?

Speaker B: Okay, my view. This will be a little hot take for uh, my lovely art art director and team. I appreciate they have a strong on my team they have a strong point of view about not wanting AI uh to compromise our value. So we don't use AI today to produce content uh, in almost any form. But my hot take is that's going to change. It's got to change. I do think if you went to ChatGPT and asked it to produce the COVID of the box of our next game. I'm not sure the results coming but at some point we should be using tools that know our brand voice, tone, our back catalog, uh, the colors. We use the brand values and books and we may not rely on it to produce our next game but the box of our game is very important because at the shelf imagine you're at Target. There's a thousand games worth 10 of them. We've got to stand out. We may not rely on it to produce that content for, but, uh, we might need 20 social ads to test. Rather than go have a photo shoot for 20, maybe we can compose those with an AI tool. I think that, uh, reality is going to be quick. I know there are people using it they're talking about at the conference. They're using it now. Results are mixed. Sometimes it's good, sometimes it's not good. Like, you know what they say about most AI tools. If it's bad at it today, it's going to be pretty dang good at it at the next generation. And if it does that, it'll be exceptional.

Speaker A: Right.

Speaker B: A year from now. So that I think that's going to change fast. So I do think we'll be using it more. But right now we are, we are very protective of our brand image, product quality and we have to do supply.

Speaker A: Okay, yeah, no, that makes a lot of sense. I think what you're talking about is also, I've heard the same part as well, which is just know like today's version of AI. So it'll be the worst version that I know.

Speaker B: It's crazy.

Speaker A: That's what.

Speaker B: Meanwhile, what's the best AI? You know, every three to five weeks it's somebody has a new model comes out or a new portion of a model that comes out and it's open eyes out in front. No, it's all about Gemini now. Claude seems to be making moves and disrupting the market and it's going to be something different or one of the, one of them is going to jump back to the front of the line in the next three to five weeks and it'll be going to be very interesting to watch out.

Speaker A: Well, it's just, it's an arms race at this point. I think that's also why we're kind of doing this sort of media community support education component, which is not to have all the media voices come from Silicon Valley. Yeah, I see. I'm from Silicon Valley by now.

Speaker B: Uh, you're an LA guy.

Speaker A: I'm an LA guy.

Speaker B: LA guy too.

Speaker A: Uh, yeah.

Speaker B: But now I'm in San Diego.

Speaker A: Right. So we'll kind of look at it from the outside end in a sense. Right. And hopefully that brings some kind of value in the sense of not having that sort of voice in the bubble or like the bubble type of like, you know, uh, everybody's kind of buying in. It's once again like there's different Tiers of adoption and where there's noise now, it's just more noise than signal, to be honest. But let's hear from the actual operators, the actual buyers of AI, uh, what are they doing? How are they adopting, how are they seeing it? How do they want to buy the AI products instead of the AI companies sort of dominating the whole entire voice. Right?

Speaker B: Yeah, I think they could. You could be made to feel like if you're not living in an AI echo chamber all day long, that you're 10 miles behind the front of the pack. I'm not sure that that's true. You know, maybe in, in the tech sector.

Speaker A: That's right.

Speaker B: More true. I can't imagine I'd be loved to see inside the tech sector and how forward people are needing these tools. But I think I look back at where I am, the consumer good world, and I think my company is at pace or maybe even a little ahead of others. We've cleared full days to sit down and teach each other best practices, best use cases. That's how I learned how to develop my own GPT. Is somebody on my leadership team was like, well, I use the GPT function. I was like, I've never done that. And you know, I played around with it and you know, a week later I've got five GPTs working for me. And it's like learning from each other is important, whether that's in the organization, from a power user or from the broader business community. That's where I would come to places like this and like, I feel like there's always a little imposter syndrome. You feel like, I don't know if I know what I'm doing, Somebody out here knows what's really happening. And then you find out we're all doing fine. But it is, it is good to find a community that can share those best practices and learnings. Say, hey, I just figured something out. Let me show you.

Speaker A: Perfect. Um, one last question, One question. Since we're in the game equal, if you had a choice to create any game you would like that you would never get sick of playing no AI games, actual games. Uh, what would that be?

Speaker B: So I will say I did not come into this industry as a big gamer, but what my wife and I love to do, we have young kids. They're getting older, but especially as they're really young, we're in this great state. If you're watching this and thank you for watching it. We're in Palm Springs, so Palm Springs is not far from our house. We love to Vacation out here. So typically when our kids are young, you get two or three families come out. We rent a house and we have pool, splash in the pool all day, make dinner. At some point, the kids would go watch a movie and the parents are sitting around the dinner table.

Speaker A: Right.

Speaker B: And we would bring what are called conversation starters. So that's games, but more questions. You know, if you could travel anywhere, where would you go? If you could only eat one last meal, what would it be? You know, And I think, you know, there's 100 cards there. We barely get through four cards because you just start telling stories and get to know people that we knew intimately. Even better. So I think if I had to come up with a game, it would be one of these conversation starters that just helps us share who we are and gets to sort of like a deeper understanding in person and not through our.

Speaker A: Yeah, yeah, that's such a good choice.

Speaker B: What about you? What games do you want to see? No, what do you want?

Speaker A: I would remake Monopoly since such a classic game. Ah. At least from what I've seen, there hasn't been any sort of meme or version. There's some, like, tweaks here and there. Yeah, I would remake some of these older games for the newer generations. But going back to your answer, though, it's so true because now when I go to different restaurants, a lot of times, like, everybody's on the phone, right? Yeah. You can't have a second of downtime if you're waiting for food. There are times where we see a table or family of four and everybody's on their own phone. That's also the part of it where I think there's definitely talks about AI that's going to impact everybody's sort of interaction with other human beings and hopefully not, you know, but hopefully there's some

Speaker B: ways it improves it for the better. Let's cure cancer, figure out what. How chill pill ones are going to save the world. And then if you, like, are stuck on your phone and you want to play a game, DSS games, we got a bunch that, um, get you playing with your friends, family and yeah, we need more of that before too.

Speaker A: There you go. Thanks for having. Thanks for coming. Thank you.

Speaker B: If you're watching this.

Speaker A: Ah, all right. Well, easy to everyone listening if you found this valuable, subscribe to the podcast AI for business leaders on Spotify, Apple podcast, YouTube and leave a comment. Please also share with others navigating the future of AI. Thanks for listening and we'll catch you on the next one.

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