Why Founders Must Rethink Their Teams in the Age of AI

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1:06Progressive Casualty Insurance Company and Affiliates. National average 12-month savings of$946 by new customers surveyed who saved with Progressive between June 2024 and May 2025. Potential savings will vary. Leave your ego at the door and always be straightforward and honest. People who will want to work with you will work with you. I don't think I'm smarter than anyone on my team or else why the hell would they be there? I think with those things in mind, it allows me to be honest with my team and open. I'm not anyone on my team's competitor. There's nothing in me that wants to feel better than you.

1:36I want you to feel like you want to be here because at the end of the day, the truth is each one of those people on your team are building your dream. Most business advice is wrong, built on opinions, echoed by people who've never done it. But the truth, it's simpler and harder. You don't win by following the playbook. You win by rewriting it. 700 episodes deep with the people who actually built something real. No theory, no fluff, no shortcuts. This is Right About Now with Ryan Alford. Hello and welcome to Right About Now. We're always mixing things up. You never know what to expect, even with our countdowns for our guests.

2:24I am excited today. I'll be honest. You do this show, I've had 700 guests. Sometimes I get in here and I start talking with the guests. I'm in the job of this person, but we're going to make some lemonade out of lemons. I don't have a problem today. We have the lovely Veronica Shelton. She is the co-founder of Oak Theory. What's up, Veronica? What's up, Ryan? Hi, how are you? I am fabulous. Reading everything you've done, all the brands you're working with, everything you're doing with Oak Theory, it's cool. What the hell is Oak Theory? Oak Theory, We're a product design studio. Now we're calling ourselves a creative tech studio.

2:55We build products, software, applications, digital experiences, and just flow with it. Full service. How'd you get into this? Nothing gets my attention like neuro-spicy creativity. I am neurotypical. I have autism, but level one, that played a huge part in me being within the industry that I'm in. I'm obsessed with, and not just tech, but how humans use it and how we adapt to things, which is going crazy right now with AI. There's a huge psychological side to it. What's the key to success? Because everybody wants the blueprint. A lot of people listen to the show. They're wanting to get the cheat sheet from people like yourself and others.

3:29Curiosity. The most successful people are the most curious people I know. They have to like figure something out because if you don't have that, then you probably aren't solving a problem that you would get paid to solve anyway. If you're curious about something, go deeper. You just like something like, oh, I like this business. I'm just going to do this business surface level. Well, you'll just stay in that space. You'll never get more. You're a woman of color. You got two things that are very untypical for that space. Being both a woman and a woman of color. What's that been like? I am what my friends call a golden retriever.

4:01Always happy. Smile glued. Even in that situation, I feel like it's been such a superpower. I have a perspective that not a lot of people have because of who I am. I bring that to the table with everything. The way you look at tech is probably different sometimes in the way I look at experiences in tech. in the way that I even have to go into meetings and how I am listened to versus not listened to sometimes. There's been, of course, these learning moments. I'd rather call them learning than negative. Across the board, there's been a lot of positive in it. If you're vocal about the value that you bring and you don't hide it, it leaves a lot of space for us to lean in and focus on innovation and how to do things and stay curious about things together.

4:38What I think, wouldn't Veronica's perspective, because she's smart, she understands the stuff, the diversity that you bring. I'm totally stereotyped here. So I don't need another dorky 27-year-old guy telling me something about tech. What do you think when you have those discussions or you're working with clients, what do you think that diversity and thought process for you, what colors do you paint with? What do you think changes it from your perspective when you get in those discussions about technology or building products? With technology, the one beautiful thing that I like about it is similar to math, certain demographic data doesn't matter.

5:11A lot of times with tech, it's more so about our brain, how we navigate things. That's something we share across the board as humans. It brings us together. It's why there's so much unity in it, because there's so little bias that is surface level. It's all here. Usually the conversations never have to do with how I look until we get past. A lot of times clients come in and they meet Hannah and I. Hannah is Korean. I'm black. We're both women. And people do not expect us to be who we are because of the biases and shit that's out there. That is a mountain that we have to climb over in a lot more meetings than I'd like to admit to be able to get to the good stuff.

5:50Usually we've had it more times. Are you guys who would be working on the project? Hi, who's the tech lead? Hi, really? Yes. Can we please just, I promise you, if we can get to it, you'll understand. Google, Disney, and Sephora. Can you talk about the types of projects or things you've done with some of these companies? With Disney, I was working on children's books. I got to creative direct quite a few big titles, which was really fun. And that was me working with brilliant artists and copywriters and printing team publishing. There was a lot of different books that I worked on. It was going into a project, doing a global campaign with the humongous company, Makeup Company.

6:28And that was working on things all the way from figuring out what models were going to use. I was very vocal about being a Black woman in tech. I say back then, but it was maybe 10 years ago, eight years ago. It was a bit more on the publishing side. With Sephora, it was like, hey, you have these models. You have one type of Asian model. You have one type of Black model, one type of Latina model. If we look at some of the stats, I was able to come to the table and be like, if we look at the numbers, this is not what they all look like. Usually models that have a look that's not commercial enough for it to probably attract the demographic you're going for.

6:58Here's numbers to prove what I'm saying so it doesn't sound stupid. Same with Lamb Sonomo. I was able to work on a project that introduced the first family of Black family in their catalog. So those are things that were race-related in those projects. And then when we go to things like Google, working on their diversity supplier platform, which is bigger. It's a bigger issue when it comes to diversity because we're talking about a lot of people across the board. Google's huge or global. We're looking at a diversity platform. It's not a black and white thing. There's people of all shades and all colors and all backgrounds who go into that.

7:30Fun projects to work on. If you've got kids in middle school or high school, you already know homework can turn into a whole situation. What should take 20 minutes somehow turns into two hours, and half the time it ends with frustration on both sides. I've got four boys, three of them right in that middle and high school range, so I see it all the time. They hit a problem, get stuck, and it's not that they don't want to figure it out. They just don't know how to get there. That's why I've been looking into Brainly. Brainly is basically a 24-7 AI-powered tutor that actually walks them through problems step-by-step, not just giving answers, by helping them understand how something works so they can build confidence and keep moving.

8:12And as a parent, that's the part I care about. It's not about the shortcuts. It's about them actually learning the material. It's also just practical. You don't have to deal with scheduling a tutor or trying to find things that line up around sports and everything else. It's there whenever they need it, and it's a lot more affordable than traditional tutoring. Honestly, it just takes a lot of pressure off. Finals are coming up. Build your teen study plan now. It only takes minutes. Go to brainly.com backslash Ryan to get 50 % off your first Brainly subscription. With my code Ryan, that's B-R-A-I-N-L-Y.com slash Ryan.

8:52If you've got kids in middle school or high school, you already know. Homework can turn into a whole situation. What should take 20 minutes somehow turns into two hours, and half the time it ends with frustration on both sides. I've got four boys, three of them right in that middle and high school range, so I see it all the time. They hit a problem, get stuck, and it's not that they don't want to figure it out. They just don't know how to get there. That's why I've been looking into Brainly. Brainly is basically a 24-7 AI-powered tutor that actually walks them through problems step by step, not just giving answers, by helping them understand how something works so they can build confidence and keep moving.

9:33And as a parent, that's the part I care about. It's not about the shortcuts. It's about them actually learning the material. It's also just practical. You don't have to deal with scheduling a tutor or trying to find things that line up around sports and everything else. It's there whenever they need it. And it's a lot more affordable than traditional tutoring. Honestly, it just takes a lot of pressure off. Finals are coming up. Build your teen study plan now. It only takes minutes. Go to brainly.com backslash Ryan to get 50 % off your first Brainly subscription. With my code Ryan, that's B-R-A-I-N-L-Y.com slash Ryan.

10:18On the diversity side, how do you balance if there's sides to an argument? Diversity for diversity's sake versus getting the best whatever for whatever it might be. The best solution or the best diverse solution. Those things aren't always the easiest to align, are they? They should always align. Diversity is not just race. It's age, ableism, gender, anything that you can do. There's some people who can't function their hands the same as others. There's some people who are colorblind. There's some people who are dyslexic. Those are all things that come into tech that a lot of people miss when we're talking diversity.

10:53It's ageism. There's some people who can't see text that's below 14 points. With technology and how we use it, tech is only as good as how easy and accessible it is for the user. Otherwise, it's a waste. You get the best product in the world, the best application, the smartest tool. OpenAI still needs a UI team. perplexity. Google, they still need a team of designers, UI specialists, psychologists, anthropologists to make sure that their tool works well for people. They have to work together. You have to have diversity in tech. Use the word that I like better than diversity. Accessibility is really what it's about.

11:27It's making complex things accessible to diverse groups that might not always be representative or thought of. That accessibility really helps frame it better. This isn't about diversity for diversity's sake. It is that accessibility because we're all blinded by our own ignorance sometimes and not what's in our sphere of influence. And so if I don't see through the eyes of these people what they go through, how they do things, that is what has to get unlocked. That's the superpower you bring is that accessibility to diverse groups. It's the empathy towards accessibility. It's becoming more mainstream.

12:07People are understanding it now. People are talking about it now. We have the TikToks and the social sites where it's even the neuro spiciness came from somewhere, right? It's because people now understand where it comes from and what it means. I'm happy with the direction we're going and which accessibility is becoming very important. What's been your favorite project? I love all my projects. I love all my clients. You guys are all amazing. Maybe you weren't sure what it was going to be, but damn, you walked away proud and excited about it. My favorite project right now is Under the Oak. It's a media project that we're working on that's coming from Oak Theory.

12:39We're very technical. We build, we make products, we make software, we build applications, and it's very project focused. The team is very project focused. We have an amazing team. We're working on this new thing where at the end of the day, we're still human. Sometimes we can get lost in trying to make things more efficient and trying to the burnout of trying to make everything, oh, it has to be super profitable. It has to be all these things. Under the Oak brings in that psychological side that Hannah and I needed, honestly, as a breakaway to be like when we do work on projects that feel maybe a little heavy.

13:11With AI coming in, there's a lot of projects that are coming in where there's this feeling of, this is so smart. This is so great, but how is this going to affect mankind? What are we seeing happening? How is this affecting our brains? How is this affecting our youth. How is this affecting how we interact with people? We know we're smart girls, so we know based on research that a lot of the things that are happening right now with AI and just with technology in general, we've seen some Asian countries like Japan, how that can lead to isolation and depression in certain groups of people. We see it in places in Europe and even in America with the youth losing their critical thinking skills.

13:45We wanted a place where we could talk about those things openly and more from an emotional side. That's my favorite project right now. What does this actually mean for how our kids are developing? It's important to look at things, especially with gaming and children. There's a lot of games that are being government funded and processes and things that are being government funded because our youth are going to lose a huge part of how they have cognitive abilities. They're not going to have the same critical thinking skills that we have. I'm a millennial. We're part of a really huge transformational era.

14:16We went from cassette tapes to now music being pulled out of thin air. we've adapted really quickly but now we're in a place where adapting is insane it's faster than that if you look at how we've changed over time and how we've become dependent we used to never have cell phones in our hands it wasn't a way of living now you cannot go without a cell phone in your hand you are completely dependent your whole life depends on it how you connect with your friends and family depend on it you don't even know what writing a letter or stamps look like these days it's completely changed how we do things calculate is out the door so if you think about that and you think that that is what we can consider a healthy timeline to adjust, if you squish that, probably I would say condense that a hundred times.

14:57That's the timeline that this new generation has to adapt to a new way of being. Technology, we used to have expectations of technology. Now we're at a place where technology is now having expectations of us, changing how we work, how we live, how we think. These are really huge things to consider when we're looking at AI and how these things come in. It's talked about, it's definitely not talked about enough. I came up in analog world. We converted to digital and now we're going from digital. And this is one second of thought, probably a better word to generative because analog and digital still require a pull.

15:30I'm grabbing something versus it's now generative. It's creating itself and pushing whether it was digital or analog, we're pulling information. We're pulling songs. We're pulling data. Now it's pushing out. There's this rumor going around with Jeff Bezos buying Vogue for his wife. If he did it, it's exactly what we're trying to do now. Even when we started and wanted to be the Condé Nast of this generation, those magazines, those are things that kind of kept us grounded. They had the quizzes in it and they had all these things that just kept us in this place where we still had fun. We were still able to look at things without this new culture to be more efficient, be more productive.

16:06Oh, you like doing that thing? Here's how to make millions doing that thing. And it's yes, yes, but that's not all life has to offer. You need to remember yourself and what's going on in here. You have kids, they still need to experience outside these influencers and all this stuff, but here's the effects that that can have on them and maybe some healthy ways in which you can go about it. We're still figuring this out. There's just this conversation that is missing in this new transformation, a new era of AI. You shouldn't be having all those conversations with AI. Those conversations need to be had among humans who are experiencing things.

16:37Talking with Veronica Shelton. She is the co-founder of Oak Theory. I love that name. Old and new. Yeah. Old Oakwood where I said theories like sound so high tech. Yeah. Very good branding. I like it. Good ground up. Thank you. Is this print? Is this digital? Right now it's digital. It's blogs. It's articles. We even have a podcast. It's a digital media platform that we're building out just to have those deep conversations about where we're at and check in where things are going. As we're hearing in this conversation with Scott Clary, entrepreneurship today is really about how fast you can adapt.

17:14Whether you're building a business, a brand, or a career, the people who win aren't necessarily the ones following the traditional playbook. They're the ones willing to rethink how value gets created and where opportunity is actually moving. That same shift is happening in investing. Sharp investors are applying that same entrepreneurial mindset to their retirement. That's where BlockTrust IRA comes in. Instead of relying on outdated traditional allocation strategies, you can move your IRA into Animus AI, an advanced system designed to help identify opportunities and navigate changing market conditions.

17:51Since 2020, BlockTrust IRA's Animus AI has significantly outperformed Bitcoin as a benchmark. Visit writeaboutcrypto.com to get started and see if you qualify for up to$2 ,500 in bonus crypto. Block Trust IRA, smart crypto investing powered by AI. There's definitely a lot of white blue ocean space for that type of content. It's unlimited. We work on a lot of projects that are coming in that are technical and especially building with AI. A lot of times there's a lot of research that goes into building things out. We might have a school that approaches us and they want to develop new ways to get their students to buy products from their store.

18:32We have to go into the psychological aspect of what makes them want to do that. What can hit them in certain places? Why do we still like nostalgia? What triggers us in nostalgia to make us want to buy something? Those are psychological things that we probably don't look at off the shelf. Like we're like, oh, it's just buying something. But it's like, no, there's a reason why you looked at that product at Target. it was a color that made you feel something and suddenly you're picking up something you didn't even come into the store for and you're getting it there's a psychological side to it when we have projects come in though we want to be able to talk about those things and what we gain from our research and bring that to the to the public under the oak is kind of our way to do that we do it with permission of course but it's like hey we did a lot of research on this thing that shows what we were talking about earlier how certain tools that your kids are using and really affect their critical thinking skills here are some ways that we've learned can help here are some ways that we've learned are impacting it.

19:23Take with it what you will. Open conversation. I imagine you're on the forefront of seeing different technologies, software or hardware side. Are you seeing stuff that would blow people's minds or is it more practical than you think? The biggest thing that everyone's talking about is AI and where it's going. It's the best tool that's ever existed. There's so much that's coming from it, from building agentic environments. That's a whole new world of its own and mind of its own. My excitement honestly goes into something that we're not going to get to for a while, but it's AR. It's quiet right now on purpose, but AR is probably where I'm definitely focusing a lot of attention to know about because I do think that's going to be the future.

20:04We're going through this evolution. That's probably going to be the big one. That's going to be the cell phone of just having augmented elements in reality in our real world. That's probably what's making me excited. I can go down the deepest tunnel with accessibility features and why that's great. It's going to change the game for a lot of people whose brains and skill sets we haven't been able to experience. I have an amazing team. I have a team of brilliant people. We started Oak Theory five years ago. We had designated spaces for them. Designers were designers, engineers were engineers, developers were developers, sales were sales.

20:35Now that we're in this new place for the past year, this is where we're seeing this huge shift in jobs and what people are capable of. Designers are now able to develop. Copywriters, people who weren't naturally creative are able to create. It's creating such a fluid space in work environments that it's ridiculous. On top of that, I've been struggling as a founder with the integrity to keep your team and not replace them with AI because AI is coming in and doing a lot of things that project management wise and things like that are just no brainer. You don't need it anymore like you used to, but you still need that human side.

21:10There's this really cool area that I've been playing around with where it's being very transparent with the team. Like, hey, jobs are changing. We need to adapt. Creative person. Now that you have AI, what else can you do? Suddenly our designer is able to write things. We're able to have copywriting done by them and they can finish projects easier. Suddenly our developers, our engineers are working across the board on in every area. I can't even go in to how vast our skillset or how wide range our skillset is now is because of this one tool. Our sales is able to put together their own pitch decks without having to go to design.

21:45That saves us a lot of money a year. That's something that I really find interesting. And I'm working on processes after processes. We've replaced our team in the past year, I will be honest. It's saved us mid six figures. And in that, we've been able to do so much more. And our team has become so poor that it's almost like a new kind of core where our team works together in such a fluid way. Our Mondays and Thursday meetings are the most amazing things I've ever seen because they're touching so many things. Now it's not so horrible to be a jack of all trades. It's not so horrible to say, I have a team that does a lot because it doesn't feel like they're carrying as much anymore.

22:19And in fact, they're like learning and having fun with it. So that is a place where I think is really fun. And having them work with agents is really interesting. Watching them work with the agents that were built in this like hybrid environment, stoping as hell. I own multiple companies. I worked in New York and I had a team of a hundred people worked in the ad agency world. This was way before AI and it will build to exactly the thing you're talking about. I was always sort of a jack of all trades in the ad agency world. And it was not the most popular thing because the ad agency world, especially likes putting people in boxes.

22:52You're the creative person. You're the writer. You're the account person. You're the strategy person. You're the media person. And how dare the account person ever be creative, strategic. And I was the strategic creative account guy that made the agency a lot of money, but wasn't always the most popular. And I started my agency radical with the intent to create sort of a flat environment way before AI and agents, because I knew you're not extracting the best out of people. Yes, you need specialization and you need to know what your job is and what your functions are. But I always believed you weren't always extracting the best out of your team when you limited them to only one function.

23:28And lo and behold, that proved to be successful. And then AI has come around and I had the exact discussion with my team. I had close to 20 employees four years ago. We have less than a quarter of that now. I've only fired one person. It's just been natural evolution of leaving and going other places and me not replacing as some of these technologies have come along. I had that exact discussion that you did. And a lot of business owners are having to have this discussion with their teams to go, this can do a lot of what your job was. I believe in you and you are talented and I need you to embrace this.