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Leveraging AI for more engaging content with Ross Simmonds

Ross Simmonds is the founder and CEO of Foundation Marketing and author of “Create Once, Distribute Forever.” Ross is a serial content creator and expert in AI and encourages nonprofits to leverage AI tools for added efficiency and effectiveness in their fundraising and marketing efforts.


In this episode of the RKD Group: Thinkers podcast, Ross discusses the importance of understanding your audience and creating content that educates, entertains, engages and empowers. He shares:

  • Why effective distribution of content is key in reaching target audiences
  • How to leverage AI tools for efficiency
  • Ways to use old stories with a new twist to resonate with audiences


Show chapters

  • 3:58 Ross’s journey into content marketing
  • 9:45 Formative principles of content creation
  • 13:02 Building efficiencies in your content creation strategy
  • 16:42 The story behind his book “Create Once, Distribute Forever”
  • 22:59 Leveraging AI and technology for analytics


Meet our guest

Ross Simmonds Group Thinkers Podcast



Justin McCord

Welcome to RKD Group: Thinkers podcast. I'm your host, Justin McCord. With me is Ronnie Richard. And, Ronnie, today we welcome our first Nova Scotian.

Ronnie Richard

That's right, yes, our guest today, Ross Simmonds. He's the CEO and founder of Foundation Marketing. And more than anything, he's a fellow content marketer. So I was super excited to have a fellow content marketer on. We even talked―he even references fantasy sports and The Sims. So I mean, I was all bought in already before we started talking about his specialty, which is really about creating content but also distributing content and the balance you have to have between the two parts of content and marketing So I, I was fascinated by the whole conversation and took a lot out of it

Justin McCord

Yeah, this is one that obviously benefits Ronnie and I in terms of what we do, but we think there are some incredible applications to the content that Ross creates and distributes that connects to fundraising strategy. And it connects to the 2024 Compass that the RKD team put out earlier this year and some of those beacons of, you know, just authenticity and of thinking about your data differently and of being more audience centric.

One of the things that you're going to hear Ross talk about are the four E's of content. So, in the back of your mind right now, you might be thinking, geez, how does this, like, how does this relate to, to fundraising? I have my, you know, two page or four-page appeal letter that I send out, and it focuses on the same story across various segments. And maybe I've got a dabble of personalization. And something that Ross said that is sitting heavy with me right now is that your content may be designed to educate or to engage or to entertain or to empower.

And, Ronnie, I'm stunned thinking about what would it look like if our fundraising messages were segmented, created and distributed through one of those, based off of the data that we know about the end individual. Just some interesting ideas. It's a super cool conversation. We talk about AI applications into marketing content. And so, I'm excited for this episode.

Hey, listen, if you are a fan of this episode or of the Thinkers podcast in general, throw us a review. We love hearing from our listeners and seeing folks provide us feedback. So, if you like this episode, give us a review and that will help us. So without any further ado, here is Ross Simmonds with his book “Create Once, Distribute Forever” on RKD Group: Thinkers.

Justin McCord

Ross, I can't decide, man, if you're a serial content creator or a serial entrepreneur.

Ross Simmonds

I think I got to say I'm both. As long as I'm the right type of serial something, then I'm good with it, and if it's entrepreneur or creator, I'll take it.

Justin McCord

Right on, yeah, yeah. Yeah, so, and diving through your background was actually the latter part. You came into our sphere through the content that you create and through LinkedIn in particular.

What drew you, like, how did you navigate to this being something where you found a passion? Walk us through that path to find that passion of content distribution and content marketing.

Ross Simmonds

Yeah, when I first got started into content, it was by accident. I just had a complete passion and obsession with two things. One was this video game called The Sims, and the other was a passion for fantasy football. And I loved both of those things. So much so that as a young, probably like 17-, 18-year-old, I decided that I was gonna start creating content on the internet about these two topics.

So, I started to write a bunch of content on The Sims. I started to write a bunch of content about fantasy sports, and I started to get a bunch of traction when I took those content assets that I was creating and started to spread them in communities. And at that moment, the light bulbs went off that, okay, I have decently good ideas that I've been talking about and writing in my little private bubble for a while, but the moment I started to see them into communities and those communities spread them and share them and love them, I realized that distribution was actually the key to the game. It was not just about creating interesting stories. It was about getting those stories in front of people who would then share them and get them in front of more people who would then share them and vice versa and vice versa.

So when I started to see that happen, I said, this internet thing could be ridiculous for me because I live in this small place called Nova Scotia on the East coast of Canada, and I want to have an impact on the world. I still want to stay here for now. The cold isn’t bugging me too much. Let's stick around in Canada.

So, I decided that I was going to create content online and see if I could build a career on the back of it through this idea of distributing it. And the content continued to get distributed. I started to get opportunities to go and work with some of the top brands in the world, collaborate with these businesses, speak at conferences and events, all on the back of this idea that if I can create value on the internet and share it freely to the internet, the internet will give me value back. And that's been essentially my playbook that I've run not only for myself, but also that I've taught my team and my team has now applied every single day to our partners and clients.

Ronnie Richard

A man of my own heart with this Sims and fantasy sports and content marketing.

Ross Simmonds

That's it. I am. I'm fully after it.

Ronnie Richard

I have a small side story here. We played The Sims a long time ago, and the maddest I've ever seen my wife in her entire life was when my brother on The Sims trapped her character inside a box, and she died.

And it actually, the character gets taken out of the game if you die in another player's house, and she pouted on the couch, got so angry, maddest I've ever seen her. So anyway, getting back to the point, so you get started, you're distributing your content, you're making connections. How do you start building a business off of that? Like, did you just start introducing yourself to people? How did that begin?

Ross Simmonds

That's hilarious. Yeah. Great game. Great game. Yeah.

Yeah, so I did work for … so after university … so I was doing a lot of this while I was in university, and it was helping pay for my tuition. And it was generating revenue because I had things set up on the back of these blogs, like affiliate links and stuff like that, that were ultimately paying me. But as the traffic to my blogs on fantasy sports and video games started to go up, my marks started to go down. So my mom was like, listen son, you're gonna graduate from university, and you're not failing. So you need to shift this blog thing that you're doing online, start writing about what you're learning in school, which was marketing. So my blog, stopped being all about all of my other passions and started to be about marketing. And when I started to write about marketing, two interesting things happened. One, local companies started to reach out and wanted me to work for them. So I got a job working at CBC, and then I got a job working at a local agency through CBC. I was able to really get the confidence that, okay, if I can come in and train all of these rep supporters and people on social media and they actually trust this 22-year-old kid with this stuff, I probably know what I'm talking about.

So that gave me a lot of confidence. And then I was like, okay, cool. If CBC wants this, other companies will want this. Let me go and see if I can get other people to buy into it. Then I started to get emails from organizations all over the globe wanting me to come and help them understand how to do social media to Gen Y and Gen Z. And I was like, cool, let's do it. So I went out, started to do that.

And then I always, at the core, wanted to run my own company. I've always been an entrepreneur. I sold do rags from my locker when I was in high school. Like, I've been obsessed with entrepreneurship for a long time. So when I started to see traction in the world of, like, me providing a service, whether it was writing blog posts, managing social media accounts and things like that, I just went all in.

And I said, all right, I'm going to put in my notice against this agency. I learned the agency game. I'm going to go out and become a freelancer. And then I started to do that type of work for brands. And it's been, it's been a great ride. It's been about eight and a half years now since I’ve been out on my own, doing my own thing.

Justin McCord

God, dude, this is fascinating. And Ross, like I mentioned, like, LinkedIn is the space that you came into our purview. I shared with you, and as we were exchanging messages, that a single post that you put on LinkedIn became an anchor for an internal presentation and training that I did, which, which read something like, “Create the content that your competition is afraid of.” And, and that spoke to me, and that spoke to our team. And, and so, you know, as you're thinking about and walking into these, you know, to corporations to provide them counsel and training on, essentially, being a creator, what are the formative principles that someone needs to wrap their minds around to become a creator in that sense?

Ross Simmonds

So, our industry at large as content marketers, storytellers, as marketers in general, I think, has gone through a very dark period. We've gone through a dark period where we've forgotten that content marketing is a two-word industry. We focus so heavily on content because gurus go on stage, and they preach at the top of their lungs: Marketers need to create content. You need to create content. Content is king. Create more content, blah, blah, that we have forgotten the fundamentals of marketing.

And the fundamentals of marketing tell us first and foremost that you need to understand your audience through with a level of empathy. If you go back to some of the early writings of people like David Ogilvie, he talks often about not viewing your customer as like an enemy or viewing your customer as like a distant relative, but to view them the same way that you would view your actual partner in life. And when you tell stories, to put yourself into their shoes and understand the nuances of the pains, and the problems and the layers that all of us have as humans and really understand that.

And then once you do, once you do the research, which is a key part in marketing, which a lot of people don't do for some reason, you then create stories that fall into the categories that I would call the four E's: Educational content, entertaining content, engaging content, or empowering content. If you can create content that does one of those four things, then well done, you're doing your job. ee

But that is not where the job ends. It's great that you're creating educational, engaging, entertaining, and empowering content. That's an amazing feat. Most marketers end there, and they don't do anything else. Like, most marketers don't even do that. So if you're doing that, well done, you're doing your job. But the next step is to actually distribute that content in the channels where your audience is spending time. You have to think about the value that you've just created―the energy, the resources, the story, the message that you've just developed that educates, engages, entertains or empowers―and how you can see that into the communities, the spaces and the places where your audience is spending time.

And if you do that consistently over and over again, you will eventually get to a point where your brand takes on a real sense of community, where people feel connected to you in a way that reduces all of the cost per click that you have to spend on PPC, that reduces the friction of that first cold email, that when you pick up the phone to cold call a donor, they're gonna say, “Oh, I just seen something that you guys just done,” and it makes everything easier. But we've fallen into this trap of content, content, content. And we've forgotten that marketing requires research, and it requires distribution. And it has to be rooted in the idea of adding value to the person on the other end of, back in the day, a billboard, but today, a screen.

Justin McCord

Yeah. Yeah. Yeah. Full stop. Nonprofit leaders, just listen to Ross; follow Ross. Full stop.

Ronnie Richard

Yeah. Yes, to all of that.

Yeah, I am curious, like, all of that, yes. How do you take that and apply that for nonprofits in a way that they often, there's often a limited amount of resources, people wearing a lot of hats. So if you don't, maybe, have time to create all this content, how do you apply that to the nonprofit?

Ross Simmonds

Yes. There's a lot of different ways that you can find time savings and efficiencies. One of the most effective is to realize that if you had a story in the past that resonated and connected with people, then that story that you had that resonated with people in the past is probably gonna resonate with people today. Because at the end of the day, we're still all just chemicals. We're all the same chemicals that we were 20 years ago, 10 years ago, five years ago. Cool.

Sure, some stuff has changed in the system, like the ... the story that you tell might have to alter differently depending on if it was reacting to something that was going on. But for the most part, stories still connect with humans. There's a reason why Disney rolls out Lion King every two decades with the exact same story, except they throw in some new graphics, and they throw Beyonce in to be Nala or something like that, right? Like, the same story, just new graphics.

Okay, so it's very likely that a lot of nonprofits have told a story maybe in 1994 that really resonated with people, that hooked people, that got them to have the most donations that they ever had before. But they forgot to retain that story. They never told that same story again. They let that message live and die in 1994, and they haven’t touched it again. That is a huge mistake. What you need to do is the same model that Disney would do. They’d look back at their greatest hits and they’d say, how do we make this modern and relevant today? How do we take an old story that connected with people emotionally back in 1994 or 2004?

Let’s say you don’t have any access to 1994 because VHS is 2004, 2014 even, right? We’re going way back, but you find it, and then you say, how do we apply this in a social lens? How do we tell the story with this through UGC? Cool. You didn't need to do research. All you had to do is go into your archives. So you use old content with a new twist, with a new adjustment, and you bring it to market. Cool.

Ross, we still don't have a lot of time to even do that. So, one of my recommendations would be to leverage one of two things: Either you're gonna leverage technology. AI is a fascinating time to be alive, and you can use AI to do things much quicker than you used to be able to do. If you're focused on a lot of administrative tasks, leverage things like ChatGPT to do the things that you wouldn't have done before. Leverage AI tools to let you do things faster, more efficiently, so you can focus on the things that need a human touch. The third thing, the third option, is to leverage your partners, right? Like, you can spend two things in life: time and money. So if you can't spend time, then you might have to spend money.

And I know that doesn't always feel good, but it's the reality. You can spend time or money, and if you can spend your money having a partner support you and execute it, that's the best bang for your buck if you don't have the time to do it.

Justin McCord

One of the things that makes Ross so compelling for those who have yet to follow him―but I'm guessing that throughout the tuning into this episode, you're getting more folks―is just your passion. And that it just, it comes out, and I think it's a part of what makes your voice so unique in talking through these things. I believe that you can't write a book without being passionate. There has to be something that helps create that drive. And your book, “Create Once, Distribute Forever,” is now out. It's just out. It's just been out for a week.

Where did the seed for that book come from? And talk to us about the journey to getting that into the ether.

Ross Simmonds

Yeah, the book is called “Create Once, Distribute Forever.” You can check it out wherever online. You can find books and order it online. You can also go to to get access to a few special bundles and offers that we have. The path has been essentially my entire career. Like, this book is everything that I have learned about distribution, about content marketing in, essentially, my entire career.

And I view it as, in many ways, like a, the, a stamp on my path to this point with insights that I've learned the hard way, whether I'm talking about how I got banned from Reddit, like, six times, but I came back and figured it out, or I'm talking about some of the successes where we've been able to help brands and generate ourselves millions of dollars on the back of some distribution campaigns. I break it all down. And my goal with the book is twofold.

One, I believe truly that some of the best ideas, some of the best, probably even nonprofits, with the best causes, with the best, they're solving super important problems, are not being held back because they don't have a good story. They're not being held back because they don't have good content. They're not even being held back because what they are doing doesn't matter. They're being held back because they don't know distribution, because they don't know the power of distributing their story effectively, because they think that that one LinkedIn post that they did, that one Facebook post was enough.

And they don't know what they don't know. So my goal with the book is to help them see how else they can distribute their content but also get over what I believe is at the root of most problems, which is fear. There is a lot of fear in the eyes of nonprofit leaders, and marketers, and creators and storytellers of a few things.

One, the fear of being judged because they're too promotional. Two, the fear that if they do promote something, that they're going to get unfollowed. Three, the fear that they're gonna share their story so often that they're actually going to realize that the story they're sharing isn't that good and they need to actually modify their story a bit. Or the fourth fear, which is that nobody is actually listening to them, and they're gonna get two likes and one's from their mom. Cool, all very valid fears. But if I can help them realize that it's on the other end of that fear where you push through it, that you're gonna see the best returns, then I will have done my job.

And I would love to have organizations, people, read this book and get through their fear so they can tell the story about things that matter, because if they do that, then the world will be better. And I don't want to get morbid on everybody, will be able to die very, very happy knowing that I was able to create something that helps people get through the fear that would have held them back, and they would have eventually had a similar fate, except they would have still had their ideas left inside instead of having them distributed.

Ronnie Richard

That's so well said. And I'm reflecting on our previous guest, Dr. Marcus Collins, who talked a lot about building culture and community. And his take on this was that nonprofits, like you just said, they have this incredible story and this incredible mission that companies dream that they could build something around this. And I think you hit on something―that it's this distribution of getting it out there that's the challenge. The story is there. Yeah.

Ross Simmonds

Right. Yeah.

Justin McCord

Yeah, I mean, this is right in line with a lot of the things that we think about, Ross, that from a distribution standpoint, the mobile device that we're all carrying around is a powerful source of multiple points of both distribution and of reception. And that's not even to mention if someone walks to their mailbox and gets a letter. Or if you encounter someone in a downtown, urban area that's doing face-to-face fundraising. Like, you've got all these different points that you can distribute your story. And too often we're trapped in either only thinking about the distribution or only thinking about the content, not marrying the two and certainly not doing it to the seamless, liquid expectations that we all carry today as individuals.

Ross Simmonds

Right, and the most fascinating part is, like, to Ronnie's point around everyone else wishing they had these stories, we oftentimes underestimate how good the story is. Like, when you are in it all the time. Like, I've sat on boards with some nonprofits that do some amazing work, and they think it's just, like, normal day-to-day because they live it day-to-day, right? They think that the work that they're doing is … everybody knows about it. No, you know about it because you work here five days a week. No one else … sure, some people know, your existing donors, they might know, but they probably don't know it as deeply as you.

So if you can get out of this idea that the stories are boring and recognize that the stories are actually life-changing and worth telling, your whole mental model around storytelling changes. Because when that happens, you become less fearful of promoting every single day for a week.

That's when, I believe, you're doing your job. When you start to see that you're unfearful, you have no challenges, you have no risk by saying, we're gonna put up something every single day. And when you do that, you're well on your way because you're going to get feedback from the community, you're gonna start to see what is resonating, you're gonna get more, you're gonna increase your sample size to be able to say, these stories are resonating, let's do more of them. And that's the key, it's the key. You want to experiment with your content, experiment with your formats, your channels and see how the community responds back.

Justin McCord

You shared earlier a couple of examples of where AI can be leveraged for efficiency and administrative tasks. And certainly, as fellow content marketers, we're all used, the three of us are very used to using LLMs at this point as an assist. Can you talk a little bit about, like, the idea of using AI on the backside of understanding what's working and not working? Like, where, how do you leverage technology to help you see insights out of the various versions of analytics that you could tap into.

Ross Simmonds

Yeah, so when we're looking at analytics today, we love AI as a secondary layer for insight. So, whether it's at the beginning of an initiative or it's post an initiative, we're leveraging AI to do an analysis faster than a human could. So, we will export data from something―like Facebook Ads Manager will export data directly from Google Analytics or Heap or whatever tools we're using to gather user data―and use a tool like ChatGPT, and we'll give it a prompt.

And the prompt, I'll talk through some of the thinking around the way that we write prompts, would be something like, pretend, hey ChatGPT, you pretend that you are a senior McKinsey analyst who has spent 10 years specializing in ads. Analyze this data, and identify for us five key insights that might be difficult for us to see with the human eye, and then it will look through the data, and it will start to look for those trends, and it will try to propose back to you what it’s found. Cool, now I have five insights. Then I’m gonna look at those insights, and I'm gonna articulate them, and think about them and apply my own first principles as a human.

Again, you don't let the AI replace you, you let it augment you. And I'm going to think, how do I apply these insights to the data and then present it back to the client? Is this a real opportunity? And then you move forward with that insight.

Or if we're at the beginning of an initiative, maybe you're going to export some of your Google analytics data or some of your historical data around your business, your growth, your traction, your engine. And you're going to say―and one thing I always try to do is I dummy the data. So I remove all identifiable info. I don't know exactly what the rules and regulations are with the chat GPT-4. I believe they can't use that data to train, but you never know. So, I don't do any of that stuff. So I've removed all that. Then I'll upload it, and I'll do the same thing, except I'll say, these are our goals, these are our priorities, this is what we want to achieve. How would you use this data to inform an approach or a recommendation? When people start using these tools, like a partner in crime, like an assistant, like a junior marketer that is attached to them, they can do so much more. And that is one place and one way that I have found it to be ridiculously useful.

Ronnie Richard

Yeah, that's a really great tip of training ChatGPT to act, like, a role, like, almost like an actor, like, pretend you're this, that works really well. Is that something that you played around with and just kind of found the right rhythm and, you know, is that something people should just kind of tinker and try stuff out?

Ross Simmonds

Yeah. So when it comes to that, we wrote a piece on Foundations blog called “Prompt Engineering.” So, if you go to Google and you type in Foundation Inc, Prompt Engineering, you'll probably find this guide. And in the guide, we talk about how different personas that you give ChatGPT results in different responses. So, if I went to ChatGPT, and I was like, I want you to write the ad copy, and I want you to pretend that you're Steve Jobs, I'm going to get a very different response than if I said, I want you to pretend you're David Ogilvy.

And those two responses will build on their tone and their understanding of the way that Steve Jobs told stories and the way that David Ogilvie would tell stories. And then that gives me a different output. This is through a lot of trial and error. We've created a ton of content on AI, and we believe that it's definitely a key part of the marketer’s toolkit.

I also will plug, say please and thank you. If this stuff ever becomes sentient, it's not coming for me. So I always say, “Thank you, ChatGPT” and, “Please, ChatGPT.” Kidding, but not kidding. But, like, those are, that's also a pro tip that I would throw out there to folks. One of the other things that's fascinating with this tech today is, like, the visual image creation. Like, you can use DALL.E, which is built into ChatGPT-4, to create graphics. You can use tools like Midjourney. Adobe has this thing called Firefly where you can have, they create visuals for you. There's a lot of cool things happening in AI that I think a lot of nonprofit marketers and leaders should be thinking about and considering for their stack.

Justin McCord

I was at an international fundraising conference in the last couple of weeks, happened to be in Toronto, and I enjoyed the eclipse from Toronto. It got cloudy just as the eclipse was coming over, which was a bummer, but even so. Sat in a room full of leaders from the nonprofit space, and we were talking about a group that we're a part of called Fundraising.AI ...

Ross Simmonds

Nice. That's cool.

Justin McCord

... which is a community of nonprofit thinkers, leaders, practitioners that are dedicated to the ethical and responsible use of AI in fundraising. And at the outset of the morning―and it was an early morning―at the outset of the morning, everyone went around the room and said, what's the one word that captures what you hear about the use of AI in nonprofit marketing and fundraising?

And while there's a range, the uncertainty is the biggest core driving emotion right now for people, that they're just uncertain. Some of that could be that they don't know where to start. Some of that could be that they're uncertain on the rules, regulations, ethics around it. Some of it could be fear because of the thoughts of job replacement or those sorts of things. And so it's a really, as you said, it's a fascinating time to be a marketer because we're at the outset of this new era that we can help shape and lean into.

Ross Simmonds

Yeah. Yeah, it is a … there's definitely a lot of uncertainty across a lot of different industries. And I think it's for good reason. Like, there's no question that with all of this comes great change, and with great change comes apprehension. And there's a lot of people who are going to be fearful.

And I think the best advice that I would advise people to do would be to view AI as something that can augment us as people and not as a replacement. View it as something that, if you can use it and you can embrace it, you're going to be able to get places faster, you're gonna be more efficient, you're gonna be more effective, and use it as a partner versus a replacement.

Justin McCord

Ross, as a multiplier―and it is a force multiplier; like, it is the biggest multiplier that we have had in a long time―we're so thankful for you spending some time with us and helping us translate some B2B ideas into the B2B, or in this case, the nonprofit-to-donor space. And the book “Create Once, Distribute Forever” is available, as Ross mentioned, at or wherever you purchase books, and can't wait to dig into it. Thanks, man, for hanging out with us today.

Ross Simmonds

Thanks for having me on, really appreciate it. And folks, if you wanna stay connected, I'm on LinkedIn, feel free to send me a connection request, but be sure to let me know where you heard me, and I'll be sure to smash that accept button. But thank you both for having me. This has been a blast, and I hope folks get a lot out of it.

RKD Group

RKD Group is North America's leading fundraising and marketing services provider to hundreds of nonprofit organizations, including hospitals, social service, disease research, animal welfare, rescue missions, and faith-based charities. RKD Group’s omnichannel approach leverages technology, advanced data science and award-winning strategic and creative leadership to accelerate net revenue growth, build long-term donor relationships and drive online and offline engagements and donations. With a growing team of professionals, RKD Group creates breakthroughs never thought possible.



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