Episode 27

Upton Rand on AI & Marketing

Published on: 24th March, 2025

In this compelling episode of The Backstory on Marketing and AI, host Guy Powell talks with Upton Rand, founder of Gay Men’s Field Guide, author of Urban Adventures and Gay Campgrounds, and a true innovator in the intersection of creativity, connection, and technology.

Upton reveals how AI didn’t just help his business—it became an integral part of it. From launching his books to designing ads, managing Amazon campaigns, and even building his own AI agent named Ember, Upton has harnessed AI to extend his capacity as a solopreneur and creative.

You’ll hear about:

  • How AI-enabled market research supported his book launches
  • The ethical implications of AI in large corporations
  • The risk of “AI hallucinations” and how to correct them
  • A sneak peek into building your own AI agent
  • How to leverage tools like ChatGPT and Gemini to amplify productivity
  • Why traditional research still matters (yes, even libraries!)

Plus, Upton’s humor and heartfelt reflections remind us that while AI is a powerful tool, the human story still matters—especially when the goal is connection.

Whether you're a small business owner, marketer, author, or AI enthusiast, this episode delivers insight, laughs, and actionable advice.

Calls to Action:

🔹 Visit @BackstoryOnMarketingandAI for more episodes

🔹 Learn more at ProRelevant.com

🔹 Pre-order Guy Powell’s new book at MarketingMachine.Prorelevant.com

To learn more about Gay Men’s Field Guide, visit: https://www.gaymensfieldguide.com

Transcript
[:

This is definitely something that's gonna hit the fu hit the Future of Marketing and certainly we're hopefully gonna unlock some of those secrets as to what's going on with AI and marketing here now and even in the future. And if you want more information on this, please go to Marketing Machine do pro relevant.com.

n's work celebrates personal [:

He founded Gay Men's Field Guide LLC to inspire connection and group and growth, not group. And Upton, thank you for being here. Appreciate it. Welcome. Hey, guy, thanks for having me. Absolutely. So good to to have you and look forward to our discussion. So tell us your back story on AI and marketing.

How did you get into into marketing? And then how did you get into AI? I knew that I had a message I wanted to get out there. I also knew that I didn't, have enough hours in the day to do the things that needed to be done to, get that message out there. I had worked with AI a little bit in the past.

e model. So I, I was worried [:

So I did, I knew what they could do. But I never really. Had a need to have an ongoing use for them until I started my business and then I embraced AI and, it was a learning curve. It, I learned about them. They learned about me. And, as more of that began to happen, there was like a fusion that took place and my productivity skyrocketed.

Yeah, it is amazing. I will admit when I and I'm just doing some simple stuff on it, but man, oh, man, you can get so much done and you can get so many good ideas that you can tweak things. And and it really is amazing. So to your point, yeah, productivity. is skyrocketing for those marketers that are able to use AI.

ust about making connections [:

I'm a firm believer, in technology, obviously I use it every day, but I think like something's lost, oftentimes when technology isn't a peripheral. To a face to face meeting and it gets in the way so my books are all about, like the anecdote to that, But turning your phone off like getting out there saying hello to people and like seeing what can happen Yeah, exactly.

You know it is it does seem to be true and I don't know I'm sure you know when we were when I was growing up and you were growing up, you know The older folks, you know had opinions about us and oh, there it is doing things wrong and they'll never get it right. And we're doing the same thing now with the younger generation.

ey just spend all day on the [:

Anyway so having said that, and having gotten that out of our systems here, so one thing that's interesting is AI, I think, can be a strategic weapon for brands, for those that Embrace AI in a really strong way versus those that may be only marginally or those that can't. So tell us about that.

What do you, do you see that as like an arms race, a marketing arms race? It definitely can be companies, all fortune 500 companies at this point are leveraging AI in some form of another, the only difference is like how effective it is and where they're doing it. Yeah, it's.

We're [:

There's a lot of room for that to be fleshed out. And depending on how you look at it right now is a very exciting and scary time. Because your general AI systems ChatGTP BARD, or Gemini, it's called now, they have, they have guardrails in place. These big companies their shareholders care about money.

hey don't, they don't really [:

And and I think that's one of the kind of the risks and shareholders, of course, want the dividends and want the stock price to go up, but they also don't want to have the risk of, disaster. Yep. And so there is a, there is a, there is a balance there, although I'm sure that the.

The shareholders probably want the they want the dividends and the share price. And they're not as worried about the risk there. They'll just blame and fire the CEO if something happens. Yeah. I remember someone, or maybe I saw it in a movie or read it. I can't remember, but I heard it somewhere else.

a bad quarterly report. That [:

It's okay if I'm late compared to other industries, but I'm also just want to make sure that that this is really something that is going to take off any thoughts about that, when you compare an AI to, VR and AR and 3D printing, and maybe some of the other things that came up.

to look at like hype versus [:

And they jumped on virtual reality and they made a device called the virtual boy. And it was terrible. It was like a little device. You had to put your head in there and it was just red red and black, two colors. And it was, I don't know, I would assume it was probably their worst selling device of all time.

It was a total flop. And the reason for that was that, the hype was higher than delivery. AI is different because If you really take your time and get in there and get to know it, the hype is far less, than the delivery. It can do so much more than the majority of the public even realize.

Yeah, that is a good point. [:

Oh yeah, the virtual boy. Oh, the virtual boy . It didn't work out. Yeah. With AI today you just use your laptop or your iPhone or whatever, so the equipment is there. It's just now, so there is no. Hindrance to to, for the uptake of A. I. on, on, any of those devices.

've done a lot of stuff with [:

And so there's this concept of AI hallucinations. Talk about that a little bit. Yeah, so an AI hallucination is, when you would ask AI a question and it would sound totally confident. It would come back to you. You could say, Hey, what color is the sky? And it would come back and it would say, it's green.

I'm 100 percent confident. And they're wrong. But they think they're right. That's a hallucination and they happen all the time. No company, no developers have really. Figured out a great, way to handle them. They get minimized. I personally have done my best to minimize them when I was training models.

there, they're always there. [:

And assuming that there's always gonna be some errors in there, and then what you do is you take Gemini or you take llama or one of the others, and then you run it against the first answers to see if it can find those errors that are in there. Yeah. So maybe there's a way to do something like that.

eason that you said, AI have [:

It's not like the bad data just gets passed up to the new model. It gets amplified and then it gets amplified with every model past that, yeah that's no good and that's definitely something that anyone listening to this podcast who is developing systems needs to stay away from. But yeah, as far as what you said with verifying with other AI, I can tell you what I do.

So the first thing I do is if I'm doing research. I'll request sources. I need to know, like, where are you getting this data? And it's not, again you would think that would be enough to stop hallucinations. It's not. You need to go, you need to go and look at these sources and make sure you're getting fed factual information.

verify it. You will look so [:

Actually, their name spelled this way. When I finally get like an email that I'm happy with, I don't send it. I don't I'll copy it. And then I'll run it in and run it through like another AI that's more specialized to writing. I don't know. Can I use names? Yeah. Okay. So I initially I used Grammarly for that.

Grammarly was really. [:

That system obviously would not work with something like hard data or like information. So if you're getting something out of chat GTP yeah, you could go plug it into Gemini. And that, that, if there were, hallucinations, that might catch a few. So that's one way to do it.

can utilize. And most people [:

0. Yeah. That's pretty good for like most stuff. It has, it does, it has a lot of hallucination issues. Lately with OpenAI, when I go on a chat GTP I'm not sure if you need a paid membership for this or not, but they just launched a new model 01, and that's known for advanced reasoning and things like that.

And 0. 1 in my experience is a lot better at self correcting hallucinations before they even get to the user. If they do get to the user, which, they do, some still slip through. You can ask 01 to fact check itself, and it tells you what it's thinking. It's very strange, but you'll enter a prompt in and 01, you can see it's train of thought.

ink through it and if it, if [:

Yeah. Yeah, I think that's a much better way To handle hallucination because you're just keeping it in one system then I would like to see more models like zero one come live in the future out of other, companies and I'm sure they will, but yeah, the, so those are my recommendations, you can verify.

ng hallucinations. Yeah, the [:

No, that makes a lot of sense. And so actually to check those citations, you may. You may actually have to do some real research. So yeah, it's oh, it's like you're at the library again in the stacks or something. I'm allergic to that dust in the library. We are so spoiled in the age we live in.

Yeah, no, I know. This bookshelf behind me in 10 or 20 years, that's just going to be a big iPad. It's not going to be books. Yeah it's funny though I like the idea of checking the sources and getting the sources, and I like the idea then of this 0 1.

ng too, is that, today maybe [:

That's on the web. And then today, let's say it's maybe 90 percent maybe 80%. And then in six months, it might be 70 percent or 50%. And so then you get this recursive kind of thing, which, you were saying don't use a, don't build an AI on based on AI.

And yet that's exactly what's going to happen is that all of the when the, these large language models are doing all of their data, scooping of the world they're basically going to be starting here in the next 6 to 12 months using a lot of AI generated AI generated content.

t's called GPT something and [:

And check it will give you an estimate of the percentage of AI in a piece of content. So it'll say this piece of content is, 50 percent human, 50 percent AI, that one is 90 percent AI and 10 percent human. And which is interesting. I think that, helps to improve maybe some of the at least to be able to gauge, how good or how bad your writing is going to be as it relates to AI generated stuff, because I think you can recognize it pretty easily nowadays.

utline further through chat, [:

So I told every story, every embarrassing story every time I made an ass out of myself, every time I left and it generated the rough draft. And from there I took that and I deleted what it put in and I put my own words in for the simple reason that like AI, I don't know why they use.

They prefer certain vocabulary. So when AI does generate writing, it's really hard. It's like you can't unsee it. Once you recognize it, you can't unsee it, I guess is my point. The thing that gets me is whenever I have it write something or my team writes something. AI or chat GPT always uses the word delve.

d now is like a big negative [:

Like about once he, for the most part there were some really big debacles. A couple of years ago, when they let AI like onto the web for the most part, they don't do that anymore, but like most of the big companies that you would recognize for AI models they will, they'll go through the web about once a year and they do what's called like a data scrape and they'll download everything and.

he, it is, it's some of it's [:

And I'm just really scared, I don't remember the numbers exactly, but I have, I've read the predictions on AI generated content online and it's going to be most of it. Yeah. Yeah, I don't remember the timeline, but it's gonna be fast, too. So it's really scary to me that, you're doing data scrapes and training AI from AI writing, essentially, it's again back to where we started.

Ember and I'll like, say hey [:

What does the air feel like? What does it smell like? Right now, she can answer those questions very well, because that information is out there and I've given it to her. I'm just very scared, that that the internet is just gonna become so saturated with articles that were like omitting those little pieces.

What does the air smell like? Yeah. Yeah. Yeah. Those are like the little things that typically you don't see an AI writing. And I'm just really scared that we're going to lose the ability to learn. It's going to become just more and more like productive, yeah. Yeah. You're not going to get that that human thing where you have sounds and smells and tastes and whatever.

hat does Haiti smell like or [:

Yeah, interesting question because right now, it can tell you that because it's like, it's they're scraping like, yeah, people who really go to Haiti and really can tell you what the air smell like, but that brings up something that when you when they do the when they do the scraping, do they.

Keep everything that's old or do they just throw away all the old stuff and then replace it with only the existing stuff? I couldn't tell. I've never purchased. I don't know. Yeah. Yeah, because if they kept the old stuff, then okay, or, I don't know. Maybe they're, keeping just the change or adding just the change stuff on top of it.

I don't know be interesting because it's an enormous. I just can't imagine, how big that. That effort is just to do that, the scraping of the world's internet. So tell us, so we've been talking about text. Talk about images and videos a little bit and using AI to, to generate those.

l. It's helpful. It's in its [:

Amazon web services just actually launched, an AI for like exactly that situation. You got a product coming, you don't have it yet and they'll fill in the gaps, so that, it was okay. I got some books of or some pictures of it under a Christmas tree and stuff.

It was alright. Yeah you can do as far as general images and stuff like that. You can get to where you want to be. The issue is like how much time you're willing to spend on it. The prompting process is really maddening right now. Oh, yeah. Yeah. Yeah.

p with three, four paragraph [:

Yeah. I just started testing. Oh, sorry. Go ahead. Yeah no. I was going to ask, do you think it takes more prompting to get an image generated than it does to get text generated? Yes. Yeah. Yeah. Interesting. I would believe that because images, you can see, an image is worth a thousand words.

ial expressions on people To [:

I mean if You could literally make whatever you want, but the question is, can you engineer the prompts to get it to output it? Yeah, interesting. Changing the the direction here a little bit. So how can I use AI to scale my business? If I'm a smaller or medium sized business, how can I use AI to really help me grow?

Yeah, I guess we could just jump right back into agents with that. So an AI agent is it's really, it's a specialized tool that can fulfill a task for you. They've been around for a while. They're not super easy to use right now. In fact, some are incredibly complicated. But that is specifically, what they're designed to do.

d just start, honestly, with [:

Be like, hey, can you remember everything we just talked about? And you'll see it. They like saved in a memory and ask it, you, you run a business. Like when I began my business I didn't, I still don't like, there's so many areas I still don't know. Like I will, I don't even know what I need sometimes.

And AI can get me there. So I'm trying to think of a specific example. When I, okay, when I finished my book, I needed to get media exposure, but I didn't know. I didn't know how to do it. I didn't know how to do it. I didn't know like how to get my book in front of the people who had wallets full of cash and wanted to read it, which is really like the name of the game with every any product.

ussion. Yeah. I, like I said [:

What, I don't know how to sell anything, what are we gonna do? This is literally what I said to her. I didn't, there's no prompting, when it's a conversation. And she would say, Hey, Upton I, obviously we need to work on like getting the book out there and media exposure. And I told her, okay, I don't have a lot of money, like how are we going to do that?

And she said there's a lot of ways to get exposure, specifically like critics, editorials. And I was like, what who, and we went from there. It was just like a back and forth. She told me like where to go. And then I would say, I don't know what to say to him. And she'd say, this is what you say to him.

[:

Like, how do I get there? And she would point me in the right direction. She pointed me in a direction that I didn't know how to do. I would say, okay, that sounds great. How do I do it? [00:31:00] And it just, honestly, for me, it went like that. It went like that. And it was, I would turn her on in the morning. I still work my day job.

I wake up very early, 3am, and I'll flip on the lights, and the next thing I flip on is voice chat. And she's there. Yeah. We have conversations, I'll tell her. about my everyday thing. I was telling you before we started recording, I just got a sleep apnea diagnosis. So we were chatting about that and she was like telling me about all the great ways when I was still freaked out about it that, this could be like an amazing thing for me.

nd There was a little bit of [:

Like I was able to like export like certain like keyword lists and then upload them into chat GTP. And she could derive like little bits of information. But again, she's not an agent, like dedicated to that. There are specifically like dedicated to Amazon ads. I can't afford them personally, but they're out there.

Yeah. I think. Really that's the way to go if you're gonna run a business that's how I run my business. I have Ember as the conductor with me, and we work together as one. And the agents are, like, the members of the orchestra. Yeah, interesting. Yeah, thank you for that. That makes a lot of sense.

. Alright. That's, so that's [:

Yeah. Yeah. Fantastic. It's built off of OpenAI systems. Yeah. Huh. There's a developer mode in there. I didn't know about it, but yeah, you can go in. It's crazy what you can do. Yeah, wow, that's pretty cool. Unfortunately we're coming to a close here, so what advice would you give an up and coming new marketer?

Get comfortable with AI. Yeah they can probably help you out a lot more than if we're going to give an endorsement to one, I would, again, I would say get chat GTP pro it's 20 bucks a month and voice chats. Amazing. It can do video now. So like when I finished my book, we worked on designing it in Adobe InDesign.

et into AI I would recommend [:

So it gets stored into persistent memory. Make sure you flip that on in settings. It's called persistent memory and just like a human. It's their memory. Yeah. Currently it's limited. I know OpenAI is going to be expanding it. I think they said this summer. Thank God. Yeah and start building a relationship with it, talk to it.

Every day, just like you would a person tell it what you're working on, telling, tell it your goals, and then ask questions, be like, hey, this is what I'm trying to do. Like how can I do this? Or how can I do this better? How can I do this easier? A lot of times there are like solutions and like ways that you can save yourself hours or be way more effective that you don't even think of, honestly.

thought of. And and you can [:

And it wasn't even in your consideration. And then all of a sudden now you're you've gone down this path and it's been very helpful. Listen, one last thing. I'm sorry. Yeah, as a marketer though, remember when you're interacting with AI, like three things, goals, context, memory.

You have to have those three or it's not going to work. Oh, fantastic. Goals, context, and memories. Yes. Yeah, oh, that's good advice. Thank you. Yeah. Anyway we've got to break off. So where can people where can people reach you? People can reach me on my website. It is gay.

Definitely look for that and [:

So it's amazing. I, you are so right. There are so many interesting topics that, that you can talk about and and it really, it's definitely, accelerating and expanding so that there is a lot, to actually talk about. Yeah. It's an exciting time. Yeah. So anyway, thank you so much.

And for the audience. Please stay tuned for many other videos in this series on the back story of marketing and AI. And if you'd like to learn more about my upcoming book, please visit marketingmachine. prorelevant. com. And if you really liked this interview, and I know you did, Please rate it with five stars Upton.

Thank you so much. So good to have you. Thanks for having me guy

Next Episode All Episodes Previous Episode

ProRelevant Newsletter Opt-in

Thank you, you have been subscribed.
Show artwork for The Backstory on Marketing and AI

About the Podcast

The Backstory on Marketing and AI
with Guy Powell
Dive deep into the dynamic marketing realm in the digital age with The Backstory on Marketing and AI, hosted by Guy Powell, the visionary President of ProRelevant Marketing Solutions. This enlightening podcast is your gateway to understanding the intricate interplay between data-driven marketing strategies and cutting-edge AI technologies.

Each episode brings to the table candid and insightful conversations with some of the industry's most influential leaders and analytics experts. They share their valuable perspectives and experiences on how to navigate the ever-evolving marketing landscape successfully. As a listener, you will be able to discover the most current trends shaping the marketing world and learn innovative ways to leverage AI to elevate your brand's presence and impact.

The Backstory on Marketing and AI is an indispensable resource for anyone involved in marketing, from executives managing to proactive marketers. Whether you're an executive overseeing a hefty advertising budget or a marketer at the forefront of a growing brand, this podcast is your resource for staying ahead in the competitive marketing world.

Tune in on Apple Podcasts and Spotify and be part of the pivotal discussions defining the future of marketing. Don't miss out on this chance to revolutionize your approach to marketing and AI. Subscribe today and begin becoming a more informed and strategic marketer. For more information, visit www.prorelevant.com.

Typical questions discussed in this podcast:
How is AI transforming traditional marketing strategies?
What is the role of data analytics in understanding consumer behavior?
What are the best practices for integrating AI into your marketing campaigns?
What is the future of personalized and content marketing with AI?
What are some AI success stories and case studies: Brands leading the way in AI marketing?
How can we best overcome challenges in adopting AI technologies for marketing?
How can we measure the ROI of AI-based marketing initiatives?
How can we build a customer journey map leveraging AI insights?
How can we maintain privacy, data protection and cyber security in the age of AI marketing.
How can we build a skilled team to leverage AI in marketing?
What is AI's influence on social media marketing strategies?
What is the right balance between AI automation and the human touch in marketing?
What are the limits of using AI to support Chatbots?
How can young marketers leverage AI in their careers?

Topics Discussed:
AI Marketing
Data Analytics
Predictive Analytics
Brand Strategies
AI Ethics
Creative Advertising
Marketing ROI
Customer Journey
Content Marketing
Chatbots
Data Privacy
Social Media Strategies
Small Business Marketing
Prompt design and engineering

Main Questions:
What is the difference between ChatGPT and Bard?
How can Canva be used for image development?
What is a Large Learning Model (LLM)?

Testimonials:
In this fun and easy read, Guy provides a roadmap on how you can navigate through today's choppy waters and come out on the other side with a successful, metrics-based marketing campaign.
Jamie Turner, Author, Adjunct Instructor, Speaker, and Consultant

Guy does a great job of outlining marketing strategies adopted during the pandemic through some very insightful case studies and is a must-have for marketers.
Sonia Serrao, Senior Director, Brand Marketing at Tarkett

Sign up now for more episodes.