Transcript of Why Founders Must Rethink Their Teams in the Age of AI

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. I 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 Write 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. I 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 gonna jab at this person, but we're gonna 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. We build products, software, applications, digital experiences, and just flow with it. Full service.

How'd you get into this? Nothing gets my attention like neurospicy creativity.

I am neurotypical. I have autism, but level 1. 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. I mean, a lot of people listen to the show, they're wanting to get the cheat sheet from people like yourself and others. Curiosity. 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.

Yes.

Being both a woman and a woman of color, what's that been like?

I am what my friends call a golden retriever. Always 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 than 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.

What 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. A 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. You know what 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 look. A lot of times with clients when they come in and they meet Hannah and I— Hannah is Korean, I'm Black, we're both women— 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. Usually 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.

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 2 hours, and half the time it ends with frustration on both sides. I've got 4 boys, 3 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. And 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/ryan to get 50% off your first Brainly subscription with my code Ryan. That's b-r-a-i-n-l-y.com/ryan. 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 2 hours, and half the time it ends with frustration on both sides. I've got 4 boys, 3 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. And 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/ryan to get 50% off your first Brainly subscription with my code Ryan. That's b-r-a-i-n-l-y.com/ryan. 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 a humongous company, makeup company, and that was working on things all the way from figuring out what models we're gonna use. I was very vocal about being a Black woman in tech. I say back then, but it was maybe 10 years ago, 8 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. Using models that have a look that's not commercial enough for it to probably attract the demographic you're going for. Here's numbers to prove what I'm saying so it doesn't sound stupid.

Same with Lamborghini. 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, you're 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. Fun projects to work on.

On 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. It'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.

You used a word that I like better than diversity. Accessibility is really what it's about. It'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. 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. People are understanding it now. People are talking about it now. We have the TikToks and the social sites where it's even the neurospiciness 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 in 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. We'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 with 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 it 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. We 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— of 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. We 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. Calculator's 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 100 times, that'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. I'm grabbing something.

Yeah.

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, I 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. Oh, 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 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.

Talking with Veronica Shelton. She is the co-founder of Oak Theory. I love that name. Old and new. Yeah. Old oak wood versus theories. Like, sounds so high tech.

Yeah.

Very good branding. I like it.

Grounded. 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 the those, uh, deep conversations about where we're at in tech and where things are going.

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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 a school that approaches us and they want to develop new ways to get their students to buy products from their store, we 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 There's a psychological side to it. When we have projects come in though, we wanna 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 can 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. Take with it what you will. Open conversation.

I imagine you're on the forefront of seeing different technology on the 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 gonna be the future. We're going through this evolution. That's probably gonna be the big one. That's gonna 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 5 years ago. We had designated spaces for them. Designers were designers, engineers were engineers, or developers, sales or sales.

Now 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 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. There'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 into how vast our skill set or how wide range our skillset is now just because of this one tool.

Our sales is able to put together their own pitch decks without having to go to design. That 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 some of 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 core 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. And 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, dystopian as hell.

I own multiple companies. I worked in New York and I had a team of 100 people, worked in the ad agency world. This is way before AI, and it will build exactly the thing you're about. I was always sort of the 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. You'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 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.

Yes, just very— no perspective.

And lo and behold, that proved to be successful. And then AI's come around and I had the exact discussion with my team. I had close to 20 employees 4 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, and I'm not gonna fire you. You need to understand that you need to be doing not just more— well, you just gotta work more. No, you don't have to work more. Work the same time hours, but the output should be 10x because of what these agents are doing. And you're no longer just this. You can be the writer and the designer and the developer, and your agent can help you do these things with product task management. If people aren't embracing that, they will be jobless.

But if you embrace it, it will be just fine.

It has to be accepted because you need a team that can be fluid and grow with you. And honestly, it's such a battle because we've had people who are like, well, I don't want to. I know you don't want to, but this is us changing software. You have to adjust to the new software. You can't just say, I don't want to learn it, because if you don't, then we can't do anything now together. And I feel like that's what's happening now. We're moving over to this new way of thinking. It is going to be the way of thinking. We have to stay afloat. We're a business, and if you're not on it and you can't do it, that means you can't adapt. If you can't adapt, we can't grow as a business. We have to adapt. That's the whole point.

People have to embrace it though.

They have to embrace it.

Those who embrace it will have plenty of work, but it's just you have to leverage it. And going to be those that leverage it and those that don't. And then if you don't, you need to go get skills trade or something, be a plumber, be a something with your hands that hasn't been replaced yet.

Intel, right? Intel, their CEO just had to make that big announcement that they did that. They did not adapt fast enough. Now they're out of the game. They can't even compete. Their CEO had to say that we failed because that's what happens when leadership doesn't adapt. So we can see that's a huge fail, how that affects everyone.

Now everyone who is like, leadership's job to coach everyone that this is the new reality and you've got to come along, because if leadership puts their head in the sand, then everybody's out of a job because the company's out of business.

I've seen friends' companies where they have leaders or people just don't want to do it. In their minds, they know what works because that's what's always worked, and now they're like up shit's creek. If there's one thing as a company we've definitely nailed is we're very chill as a company. We're 4-day work week, we're not really on everyone's ass all the time, but when we have hard truths like this, this is when we kind of sit the hell down. We gotta, this is real. The hard conversations was pretty soft because it's, we left so much open for where do you see yourself evolving? You have to do it. You have to evolve as if this is what's happening to your role. Here, let's use this same tool to show you where your skillset could take you. Where do you wanna go? Okay, how is that gonna bring value to the company? Like these are conversations we've had with each and every team member. Hey developer, you're doing frontend right now. Now we have these tools. By next week, I want to see you introduce 3 other tools to me that will allow you to expand your skillset using AI.

We'll pay for it, we'll fund it. We pay for them to learn, we pay for their classes, but you have to grow or else we're going to have to replace you because now we won't be able to compete. And if we can't compete, we can't feed everybody. We got family, people with families. We're not about to let them not eat just because yo ass wants to sit here and say, well, I'm comfortable doing this. It's real conversations that are being had, but it's made such an impact on our team and we're stronger than ever. Robots talking in the team, it feels seamless and it feels beautiful and it feels just as homey and cozy as it always felt.

It doesn't have to be uncomfortable unless you make it that way. It should be exciting because for me, I've loved it not because my employee costs are lower. I loved it because how much more productive I know how I could think and spend more time on the stuff that matters versus mundane things. And so if you're not embracing that reality, then And that's the problem, not the other way around.

It gives us space to focus on what matters. It gives us space to look at projects. And now, because so many of those mundane little tasks that had to go into a project that more tactical, more step-by-step process, those can get done. And so now we can focus on real problems and how to solve them. That's even what gave us the room to start this Under the Oak because we were able to now say, holy shit, look at all the psychological things are going into this. It's what gives us space to do more. And I'm watching it with friends' companies. A lot of people are starting sub-brands and other companies now within their company because of this. It gives you room to see things that you couldn't see before because you're so focused on getting the project done. Now the projects are getting done more efficiently, less hands on deck. You're able to really have a wider look and range on what you're working on and why, and there's a beauty in that.

You seem like a great leader. Has that been nature or nurture, your leadership?

Both. A lot of humility. I don't know if it's a neurospicy thing, but I think if there's one thing I tell everyone, How do you deal with so many personalities? I'm like, leave your ego at the door and always be straightforward and honest. People who will want to work with you will work with you. You'll see patterns immediately with people. Always pick up on that. But I leave my ego at the door. I don't think I'm smarter than anyone on my team, or else why the hell would they be there? 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. I'm like, there's nothing in me that wants to feel better than you. I want you to feel like you want to be here because at the end of the day, the true The truth is each one of those people on your team are building your dream and you're giving them freedom. I offer freedom tokens, pay you for what you're doing. That's the trade-off. At the end of the day, they're building something for me. And if they want to be a part of it, that's great.

'Cause I'm like, listen, I'll do whatever I can to make sure you're part of this ride, honey. I'll make sure that you're in it, that you feel like it's home. I think there is that ego thing where you have to drop it aside and be like, that is the hard truth though. If you hire right, talent that you feel like you cannot replace, there's a lot of value that you put on them.

Under the Oak sounds like a podcast to me. And I have a podcast network, so we should talk more about that.

We should. We have so many recordings already, things that we talk about, and it's just putting it out there. And I think, you know, you've been doing this for a while. There's that perfectionism thing that comes in, and there's like this thing that we're working through and still trying to get through. And especially because on my end, I'm very opinion-based with my conversations, and we're still getting through.

That's what makes it spicy.

Listen, that is my personality. We're figuring it out, but it's really fun, and I'm really excited about the conversations we're having. Where can everybody keep up with everything you're doing? Oh, Theory co, co, undertheoak.co, co. My social, if anyone wants to reach out to me, is Ver Shelton. I'm on Insta and everything else. You can follow me on LinkedIn. But undertheoak.co, we have a contact. Reach out if you want to reach out. Let's talk. We're always open to work on new projects and fun new things.

Well, you were awesome. You look great. Let's stay in touch. I'm serious. Hey guys, you know where to find us, ryanisright.com. You'll find highlight clips from today's episode, the full episode download, links to YouTube. We appreciate you for making us number one. We'll see you next time. Right about now. Here's the truth: information doesn't change your life, execution does. So don't just listen to this episode and move on. Take the idea, make the call, launch the thing, fix the problem, build what you keep talking about building. For more, follow Ryan Alford on Instagram @ryanalford and watch or listen to every episode at RyanIsRight.com. This is right about now. Now quit waiting. Go win.