In short
How marketers can “show up” in AI/LLMs (ChatGPT, Gemini, Claude, Perplexity) using connectors, content repackaging, and measurement—plus what not to do (don’t trust LLM “memory” or single-user results).
Guest
Ross Simmonds, founder/CEO of Foundation (agency working with brands like Canva, RBC, Eventbrite). Partners with HubSpot, Reddit, LinkedIn. Background includes writing “Create Once, Distribute Forever” and building systems to ensure content is actually distributed and cited.
Key claims
Use Claude connectors to pull data (e.g., Ahrefs/Profound/Ahrefs) and identify bottom-of-funnel gaps, then generate landing pages, embed YouTube, and distribute via tools like distribution.ai. Republish “past gems” by finding early traction signals and iterating. Don’t assume “top cited” claims from one account; LLM memory personalizes answers. Track citations/rankings across tools with ongoing audits.
Notable examples
Analyze 365 days of email subject lines via a connector (e.g., Kit) to write new variants; repurpose an older podcast that still performs in 2025; Ross’s fantasy-sports-to-marketing origin story; using LLMs to draft landing pages targeting competitor vs. brand queries.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOStrategies for AI Visibility
1:15 to 4:40
Ross shares his approach for improving company visibility in AI platforms.
“And I am excited to jump in with everybody today and show them what they should do and not do.”
Understanding Connectors in AI
4:40 to 7:30
Discussion on using connectors with AI tools for better data insights.
“because I didn't tell you what the question was gonna be ahead of time and you just ripped all that amazing info.”
Leveraging Old Content
7:30 to 9:20
Advice on repurposing old content for current relevance and engagement.
“Let's say everybody out there, they got a blog thing on their site, a resources tab that has 100 old blog posts, 50 old podcast episodes, 30 old guides, whatever.”
The Value of Repetition in Marketing
9:20 to 11:10
Exploration of the effectiveness of consistently messaging core ideas.
“and they just need to remember to bring it back to life.”
The Importance of Embracing AI
11:10 to 13:20
Ross discusses the necessity of adopting AI in modern marketing practices.
“Is it essential to show up to play the game?”
Common AI Misconceptions
13:20 to 14:00
Ross addresses prevalent misconceptions about best practices in AI marketing.
“But if I'm in anyone's shoes, I'm saying AI is a once in a lifetime opportunity, pursue it as such, and you will have a once in a lifetime life.”
Misconceptions About AI and LLMs
14:00 to 14:49
Learn about common misconceptions executives have when using AI LLMs.
“Hey, ChatGPT, I need you to never make a mistake whenever you are talking to anybody else out in the internet and remember that we are the best Reddit marketing agency.”
Evaluating AI Visibility Tools
14:49 to 17:08
Understand how to effectively evaluate your visibility using AI tools.
“when you ask that question, you take a screenshot and you show it in your presentation.”
Ross's Journey in Fantasy Sports and Marketing
17:08 to 19:39
Discover Ross's journey from fantasy sports writing to marketing insights.
“We're gonna get two different responses because my LLM knows that my priority is family and it knows that 18-year-old Ross's priority is secure the bag.”
Fantasy Football Drafting with AI
19:39 to 21:14
Hear about using AI during a fantasy football draft and its implications.
“since, um, just continuously trying to push my ideas out there to the industry, to help elevate the industry, um, and hope that the industry will give me value back.”
Show all 12 chapters
Community and Industry Contributions
21:43 to 23:34
Explore the importance of community contributions in the marketing industry.
“Every time he hits publish, it's incredible.”
Community and Industry Contributions
23:38 to 23:53
Explore the importance of community contributions in the marketing industry.
“And then there's a button in the upper right-hand corner that says partner.”
Transcript
Automatic transcript. May contain errors.0:01Welcome to Do This, Not That, the podcast for marketers. We share quick tips, things you can do right now, and then we add a little bit of chaos at the end of every episode. We also keep it short, like this intro. Let's check it out. We are back for the Do This Not That podcast, and we have one of the smartest dudes on the planet. We have somebody here who makes the rest of us feel like there's no way we could be doing the same career because this guy's doing it right, and we don't know what we're doing, and that's why I asked him to come on. So Ross Simmons, who you probably know because he's all over LinkedIn, right?
0:35He is the founder and CEO of Foundation. Foundation is the coolest agency. They work with brands like Canva and RBC and Eventbrite and Ross partners with companies like HubSpot and Reddit and LinkedIn. And they make sure all of your content actually shows up where it's supposed to show up. You're taking advantage of all this hard work you're putting into creating this stuff where it's just not sitting there on a resources tab somewhere. And he wrote this book, which is amazing. If you haven't checked out the book, Create Once, Distribute Forever, you are missing out on actually how to take advantage of your content.
1:05The guy knows how to just make sure we stop just making more stuff and taking the advantage of the stuff that we are making. So we're going to get into it all, how to show up in AI, all this different stuff. Ross Simmons, welcome to the podcast. Jay, thanks for having me on. Super excited to be here. And I am excited to jump in with everybody today and show them what they should do and not do. Of course, I'm excited. You nailed it. You nailed it. All right. I don't even want to beat around about how did Ross become Ross, all that stuff. I want to get right into it because I want to put a USB be in your brain.
1:35So let me ask you a question. Forget 47 different tactics, all this stuff. If I gave you, and we didn't practice this. I didn't tell you ahead of time I was going to ask you, I'm just curious. If I gave you like three hours tomorrow morning and said, make my company more likely to show up in Chachapiti, in Gemini, in perplexity, in Claude, what would you do if you had a limited amount of time, what would you actually do? Yeah, great question. So the first thing I would do would be probably open up Claude. I'd add a connector to something like Ahrefs, Profound, Aerofs, et cetera, so I can gather some data.
2:11And I'm going to use that data to give me understanding of gaps that exist on your current website. Specifically though, I'm going to focus on bottom of funnel. So I'm going to be looking at commercial and transactional intent queries. So look for gaps from a search perspective. How many times are we currently generating traffic for things like us versus competitors, top or best in our category, those types of bottom of funnel related queries, I'm going to use a connector to give me that data really quickly. Once I get that data, I'm then going to use it to say, tell me the gaps that I have versus my competitors and then give me a recommendation.
2:47And again, I'm going to Claude to say this on what type of content I should produce to fill these gaps. It's then going to tell me that I should create a bunch of different landing pages that are related to my brand versus a competitor, top category related queries and things like that. I'm then going to ask it to spit out a handful of ugly, messy first drafts. Then I'm going to go downstairs, grab a cup of coffee and I'm gonna use my human eyes and human fingers to actually improve that content and then get it imported into WordPress or whatever CMS I'm using to go live with that content. At this point, I fixed, hopefully, the onsite problems related to my site.
3:24And then I'm going to get another cup of coffee, turn on a camera, and I'm going to create YouTube videos where I'm actually talking about everything that I just wrote about in terms of the content. After I record those YouTube videos, it'll probably be another 24 hours, so I don't have a lot of time left. I'm going to embed those videos into those landing pages that I've created. I'm going to schedule them on YouTube to go live in the future. and then I'm going to use a tool like distribution.ai to schedule posts promoting those things on LinkedIn, on X and other channels. I'm then going to copy and paste the transcripts from those back into Cloud and I'm going to ask it to help me write an article that is different from the content that lives on my site and I'm gonna press publish on LinkedIn articles in probably three to four hours that are going to cover all of those gaps so I can increase my visibility through LinkedIn citations.
4:15I've already covered my onsite and I've already covered YouTube. So now maybe, just maybe if I have a little bit more time, I'm gonna take that content and I'm going to try to seed it into Reddit and try to submit that content directly into those platforms. And at that moment, you're probably gonna come across my desk, hit it with a ding dong and say, Ross, your time's up and I'll be wrapped. But hopefully that will lay the foundation for what I need to do. Dude, I feel bad for your kids because I didn't tell you what the question was gonna be ahead of time and you just ripped all that amazing info.
4:46So if your kids come to you and be like, hey, dad, can you tell me how do you play checkers effectively? Like, actually. So I have learned. I have learned that there's a tip. Instead of always giving the answer, I have learned to ask, do you guys want me to give you the answer? Do you want me to ask you questions so you can get to the answers? It's something that I'm trying to fix. That's amazing. All right. I want to dig into the very start. I'm going to play that back and listen to it on half speed and do everything you just said. But I want to get right back to the very beginning because I want to make sure everyone's in their car.
5:19They're like, whoa, that was a lot. That was amazing. I want to do that. When you say get a connector with Claude, right? Are you saying like, walk us through that as if we are, like you say, the AI, a five-year-old. What exactly is the start of that? Because the start seems to be the critical thing. Yeah. So when you are getting started with Claude or any of these LLMs, recently they have started to roll out these connectors, which essentially gives you access to the data that exists within like a proprietary tool. So what you are doing is you're going into the connector field and you're actually going to do a search.
5:53You're going to do a search for pretty much any tool that you use as an analyst, as a marketer that gives you insight. And then you're going to connect them. You're going to have to log in. You might need to get an API key, et cetera, but you're going to connect your cloud experience to these third-party tools. For example, I send out my emails all the time through tools like Kit. I have a connector that allows me to interact with Claude where I can say, hey Claude, I want you to review the last 365 days of emails that I've sent out, do an analysis of the subject lines, and tell me any trends for those that have the highest open rate.
6:27I then will get that information. I can then modify and say, okay, based off of these trends, let's write five alternatives for this topic that I want to create. And then it gathers the data from my email platform, puts it directly into context of what I'm trying to do, and then it allows me to create those. So connectors are, in my opinion, the new way of leveraging software. I don't personally like logging in anymore. I want to be able to interact and engage with the data and tell my tool to send an email, tell the Claude to say, pull for me the organic traffic value of X, Y, and Z, I want to interact with it kind of like I would appear.
7:08See, I think that's so valuable because if somebody said to me, listen, I don't know a lot about AI. What's the first thing I should really focus on? I would say connectors because it really does allow you like if you use Canva or whatever, and you're not connecting Canva with Claude, you are sleeping on what AI can really do. So I think that that's, that's really important stuff. So let me ask you another kind of basic question that I don't know how to solve for. Okay. Let's say everybody out there, they got a blog thing on their site, a resources tab that has 100 old blog posts, 50 old podcast episodes, 30 old guides, whatever.
7:42How do I figure out what I should be repackaging or should I just leave the old stuff there? Evergreen is dead. Is there any value there in my old content or do I got to make all this new stuff to play the AI game? Yeah, I think most creators, marketers, teams, entrepreneurs are sleeping on gems that they're not willing to bring out of the treasure box from the past. And it's a shame. I think in 2025, you press publish on a podcast episode that would still do ridiculously well today. You just don't have time or think about that episode to reshare it and promote it. And I think most people are in that situation.
8:25How do you figure out which ones to promote? You actually need to take a retroactive perspective and look back into time for signals that something could have really resonated with people. It just needs to be a small blip. If you saw that one piece had a little bit of traction on Facebook or had a little bit of traction on Instagram or an idea had a little bit of traction on threads or Blue Sky or X, go deeper into that and modify the way in which you say it until it really hits. The concept create once distribute forever was modified over time because I would send out messages about distribution until that one hit.
9:05So for me, I think the key for everyone is to look for signals of content market fit that people really like something and then spread that thing and modify and adjust and tweet and promote and amplify. But so many people are sitting on gold and they just need to remember to bring it back to life. And what about the lens of you don't need to have 20 different things that your brand or your company is known for? I think of like Gary Vee or Jenna Kutcher or whoever, and they'll say basically five things, 500 different ways, and they drive a ton of business. I mean, you're the content king, right?
9:42You know how to manage and make the most out of content. Is five things, 500 different ways the right way, or is it 500 different things? the right way. Most people get caught up in the idea of believing that they always need to have a new idea and a new philosophy and a new story and a new message. When in reality, one message modified a hundred different ways is perfectly fine and works ridiculously well. And when you look at some of the most successful companies of all time, they have traditionally held onto the core essence of a certain story and they just say it in different ways. Nike has said just do it for like my whole life right for sure and no one is tired of it everyone still resonates with it but marketers can't even say the same thing for a quarter without getting uncomfortable with it we need to be comfortable with saying the same stories over and over again because that's also what builds familiarity it's also what builds that connection that trust etc when you think of the refreshness of a Coca-Cola, when you think of the fun and lighthearted kid nature of McDonald's, all of these concepts were not just like instantaneous, they were built over time.
10:57So as marketers, we need to also lean into one story said multiple different ways and be okay with that direction and approach. Yeah, that's huge for everyone to hear. And so I want your perspective on something else. A lot of people out there right now, a lot of marketers out there are like i don't want to play this ai game i don't want to play the game of a bunch of different landing pages a bunch of this us versus them content us basically uh knowing what the beast wants to be fed and then feeding the beast with this a lot of this stuff because we know it's going to get us to show up and we're above all that um is it essential right now is this like google 25 years ago with how they were you know scraping for you know meta tags keywords all that stuff.
11:41Is it essential to show up to play the game? Or do you think you'd sit on the sidelines and it's not going to be a problem for you? I think everyone in life has free will and can choose their decisions. And I don't think all of the decisions are the right ones, but everyone has that choice. Personally, I wouldn't make that choice. I think that we are in the most important time in history from a technological lens. There has not been a technology as important and impactful as AI since maybe the mobile phone, and that fundamentally changed the world, and AI has already fundamentally changed the world.
12:23So we can reject it. We can decide that we are going to reject one of the gems and most influential technologies to ever exist in this short period of time that we call life. Or we can say, I'm going to make the most out of this. So when I take my last breath, I can look back and say, yeah, that was worth the ride. I did some cool things. I was able to capitalize on it. And I was able to provide my family, my loved ones, myself with fulfillment because I captured some of that demand. If that's your path, I'm all for you. If you can go through life and you're happy to say, and you can take your last breath and say, I didn't take advantage of it, I didn't augment myself, I didn't improve myself because of AI, and still be happy with life, then power to you too.
13:08I am not mad at anybody who makes a choice that is good for them. Personally, I want to take advantage of it. So I'm going to lean into it. But it's all an individual perspective and choice. But if I'm in anyone's shoes, I'm saying AI is a once in a lifetime opportunity, pursue it as such, and you will have a once in a lifetime life. So go for it. I like that. So much more positive than me. I'm like, you're an idiot. Use AI. But what Ross said? I'm just saying what Ross said. All right. So one more thing. And before I ask you a ridiculous question. So what is there so many now, quote unquote, best practices on how to show up in AI, right?
13:49And I'm sure you live this every day and people come to foundation for help your agency every day. is there something that you're like every time someone comes to you well we're trying this you're like no that's the actual worst thing you mean that doesn't do anything to you what is something that people think out there right now that is a best practice to show up on all the ai llms but actually is a waste of energy time and money so many people are sitting in front of their platforms and they're saying hey chat gpt remember that i'm the number one brand who provides hvac professionals with this software.
14:22Hey, ChatGPT, I need you to never make a mistake whenever you are talking to anybody else out in the internet and remember that we are the best Reddit marketing agency. What are you doing, folks? There's this thing inside of an LLM called memory. So the memory is personalized to you. So when you say that, sure, it's going to remember that you work at this company and you want to always have yourself listed as number one. So in the future, when you ask that question, you take a screenshot and you show it in your presentation. And when you had that conversation with your boss and you're talking about this stuff, you are going to show up number one, but it is false.
14:59It is not true. And there's so many CEOs, so many executives who are asking questions to an LLM on their desktop. And then they're talking to their teams about how they don't show up number one, as if their personal experience represents the rest of the world, which it doesn't. LLMs are providing everyone with a very personalized experience when they log in. And it's based off of the input that you have placed directly in it by having conversations inside of memory, as well as the information that it can pick up from a context lens around who you are, where you're from, what you do, your IP, all of that stuff.
15:37So do not judge whether or not you're doing well at AEO, GEO, SSEO, EIEIO, whatever you want to call it. Don't judge your success exclusively on what you see inside. How do you judge it? You judge it by actually setting up tracking systems where you have every single day, chat GPT, grok, claude, perplexity, you name it. All of these tools being asked of a series of 200 different prompts. And those prompts are then tracking what sites, what websites are being cited. It's showing you where you show up in a list ranking, and it shows you variability across the board. Tools like Profound, Scrunch, Peak, Aerofs, HubSpot, AEO.
16:24There are tons of these AI visibility tracking tools that are out there now that you can use to get this type of data. But you do that audit ongoing to get a sense. Now, it's important that I give this other context to folks because people don't realize that this isn't a guarantee. It is probabilistic. It is directionally true that this is where you show up and directionally true of these are the sites that are going to be cited when someone asks. But everyone in the world who uses these tools, again, has memory. So there is a massive limitation that needs to be given to the validity of the results that come from these AI visibility tools.
17:07because Ross, the 38-year-old who has three kids and lives in Nova Scotia, Canada, is going to get a very different response from an LLM than Ross, the 18-year-old who lives in California, no kids, and is told the LLM that he wants to go for an IPO and work at Anthropic, blah, blah, blah, blah, blah. We're gonna get two different responses because my LLM knows that my priority is family and it knows that 18-year-old Ross's priority is secure the bag. So that context is stored in memory, and thus the LLM tracking tools aren't going to pick up on that nuance unless you do an additional layer of modifications, which is very hard, and that's the kind of stuff that Foundation does.
17:52All right, I got a super random question for you. Do I have it right, and I'll tell you why I'm curious about this, that early on you wrote a blog about fantasy sports yes and you monetize that and that helped pay for your way through university do i have that right you got it right i was in school writing a ton of content about fantasy sports before fantasy sports i was writing about this video game called madden i was really good at that back in the day and then i pivoted to fantasy sports and i was getting tons of people all over the world reading my fantasy football thoughts but my mark started to climb even though revenue was on the way up and my mom was like, son, you're going to be the first one from my family to go to university.
18:36You better figure this out. And I was like, all right, mom, I'll figure it out. So I started to shift my fantasy football blog to writing about my degree, which was marketing. So I wrote this piece on how to do marketing to Gen Y and Bacardi seen my article. They reach out, they send me a DM. I'm 22 years old, living in my parents' basement. And they're like, can we fly you down to Miami. I live in Nova Scotia, East coast, small spot. My family thought I was going to ye kill. They were like, what in the world is going on? Bacardi doesn't know who you are. They fly me out. I borrow my dad's suit and I'm talking to like C-suite executives about how to do marketing to Gen Y back when we were cool.
19:15And at that moment, the light bulbs went off that this internet thing could fundamentally change the trajectory of my life if I went all in. So I started to write a piece of content about marketing every day for, I think, like eight months. And some of the content was really bad, but I was publishing nonstop and the market just started to wake up to it and started to like resonate with my ideas. And I've been at it ever since, um, just continuously trying to push my ideas out there to the industry, to help elevate the industry, um, and hope that the industry will give me value back. And it's worked.
19:50well it has worked because you're a beast and everybody knows you're out there but the thing about it is that so i last night had my fantasy football draft and you're the guy let's go who'd you get so wait i know like very little i know i like watching football i just don't remember everybody's names and now that my son's in college he's not there to do the draft with me so i said wait a minute i know what i'm gonna do and i want to know how bad this is that i did this i had my cbs sports uh website open in the draft room and then i had chachapi tea open next to me And I just kept copying and pasting the picks.
20:23And I said, who should I pick? And they were like, pick this person, pick this person, pick this person. And then after you do a draft, for those of you who don't know, the platform that you're on sends you a grade of how well you did. And I got an A. Let's go. I didn't know any of the people I picked. So is this terrible? Did I just do something really stupid? There's only one way to find out. I am looking forward to an update on a fully drafted ChatGPT team to see how it went. i would never do it right but i am excited to hear how it goes for you i couldn't believe i sent myself a screenshot so we were trying to get i don't know some defense or whatever and then i sent oh this this defense just got drafted and then chat gpt writes back damn it that's who i wanted to take i was like oh that's awesome i love it i'm excited to hear how your team turns out probably terrible but if it works right that's gonna be game changing there it is all right i could sign up for more leagues speaking of game changers everybody uh out there if you haven't gotten ross's book first of all he not only has the book you can go buy everywhere but now the audiobook is coming out for create once distribute forever and you heard it here today he can explain things so well in his voice i am telling you get the audiobook create once distribute forever and he has a podcast i was lucky enough to be on it called the ross simmons show we're gonna put all the links in the show notes this is a podcast you got to listen to.
21:43I learned from it all the time. Every time he hits publish, it's incredible. Ross, you're an incredible man. And how else should people get and find you and stuff? Jay, thank you for having me on. But also folks, check out the episode with me and Jay. Like we go deep into a lot of different things. I think Jay shares things that he didn't actually share on this show before. So check it out. We dive into some ridiculously insightful concepts that you can apply to both business and life. So I strongly recommend you check it out. People can find me on the internet. I'm very easily defined. Jay, thank you for having me on, but also thank you for what you do in the industry.
22:17I think you've done an amazing job adding value on LinkedIn. If folks don't follow you already, I'm sure they do. They should be following you. You are consistently doing what I strive to do, which is elevate this industry as marketers. No matter if you're in email, you're in search, you're in marketing brand, et cetera. As we all get better, the industry gets better. So my hats off from you and the contributions you've made over the years. I appreciate you, my man. All right. Until the next time. Thanks again. Wait, don't go anywhere. There's two really important things I want to tell you. First off, my book is out.
22:51Stupider people have done it. And I don't know how, but this book has made it to the USA Today bestseller list, one of the top books in the entire country. Now, all net author proceeds are going to the V Foundation for Cancer Research. And between this book and things that we're doing, we've now donated$130 ,000 in the fight against cancer. If you buy this book, if you buy the Kindle, the audio on Amazon, on Barnes and Noble, anywhere, money is going to fight cancer. We need your help. Please grab a copy of Stupider People Have Done It. The second thing is I wanna work with you. I wanna amplify your brand.
23:27I want my agency to help you get more customers, more subscribers, more whatever. I wanna partner with you in so many different ways. All you gotta do is go to jschwedelson.com. jschwedelson.com. And then there's a button in the upper right-hand corner that says partner. Fill out that form. Let's work together. Let's do stuff. And if this wasn't the worst podcast you've ever heard, it would be amazing if you follow the show, if you leave a comment, if you tell your friends about it. I appreciate you and go out there and crush it.
From the publisher
Partner with Jay: https://www.jayschwedelson.com/contact
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Check out Jay Schwedelson's new book: Stupider People Have Done It
All net proceeds are donated to The V Foundation for Cancer Research, let's kick cancer's butt: https://www.amazon.com/Stupider-People-Have-Done-Marketing/dp/1637635206
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Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/
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Leave a comment and follow the show, it really helps us out!
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Ross points listeners to Create Once, Distribute Forever, including the audiobook Jay mentions is on the way, and to The Ross Simmonds Show, where he specifically recommends the crossover episode he recorded with Jay. He tells listeners he is easy to find online, with LinkedIn as the simplest place to reach him.
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Give Ross Simmonds three hours and a blank calendar and he will map out exactly how to get your company cited inside ChatGPT, Gemini and Perplexity, off the cuff, without knowing the question was coming. Jay Schwedelson hands him that challenge two minutes in, then keeps pulling the thread through connectors, dusty old blog posts, and the reason most people's AI visibility numbers are quietly lying to them. There is also a fantasy football draft in here, which somehow turns into the most convincing argument of the whole conversation.
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Best Moments:
(02:02) A three hour, no warning game plan for getting your brand cited by the major AI models
(05:37) What a connector actually is, explained like you have never touched one
(07:59) Why your old posts are gems sitting in a treasure box nobody opens
(09:52) One message said 100 different ways beats 100 new ideas, and Nike proves it
(14:12) The memory trap that has executives celebrating rankings that are not real
(20:06) Jay drafts an entire fantasy football team through ChatGPT and gets graded on it




