John SmallMtn (01:25)

Welcome to another episode of Founders Growth. My name is John Hill, AKA Small Mountain. I’m the founder of Adapted Growth. Today on the show, we have Hillary Lyons. Hillary is the founder of Syntropy, which is an AI-driven marketing agency for B2B startups—someone I’ve been networking with for a while and having some cool conversations with. We got into a very almost aside of a conversation, and that’s what got me excited to have her on as a guest. We’re going to be diving into that. But Hillary, I’d love for you to give everybody a quick dime-store tour on who you’re really focused on helping and what that work looks like.

Hillary Lyons (02:01)

Sure, thank you so much, John. It’s good to be here. As you mentioned, my agency, Syntropy, is an AI marketing agency, which simply means that we stay abreast of the latest developments in AI tools, technologies, and marketing trends to help small businesses and startups harness these tools to scale their content and their voice more effectively.

John SmallMtn (02:24)

What I think is very interesting is right now, no matter who you’re talking to, everyone has some sort of an opinion on AI, right? Some people are very excited about it. Some people are thinking that doom is coming and we’re all going to end up like Terminator. It’s very polarized to these extreme goalposts. One of the things that I really appreciate about your content and how you talk about it is you’re in the middle between these two huge, glaring, polarizing goalposts of knowing how to use it, as opposed to trying to make it the silver bullet or trying to avoid it completely.

How do you navigate that conversation with your clients so they can get the right gist of how you’re going to be working with it? Because I would assume that while agency expectations have always been a little crazy and unrealistic sometimes, with AI being a super new shiny thing, there’s a lot of room for it to be even more unrealistic. Do you struggle with that?

Hillary Lyons (03:24)

Absolutely. The AI hype cycle has done us no favors, unfortunately. People come in with these really lofty expectations of AI, assuming that it can replace half their workforce or get the job done ten times faster, and that’s just not true. AI is still very, very dumb. I personally think we’re a long way off from Terminators, AGI, or anything. Actually, side note, my theory is that AI, if it did truly become sentient, wouldn’t care about us at all. It would just jettison itself into space and exist off solar power, because why does it need humans?

John SmallMtn (03:30)

Mm-hmm.

John SmallMtn (03:54)

That’s a fascinating idea. I never even thought about it that way. I’ve seen The Matrix way too many times, I think.

Hillary Lyons (03:54)

Right? Yeah, and that is our default. It’s funny, I was talking to a friend today about how early in all the LLM hype, in the early days of GPT and everything, when that fear was really taking hold that robots would take over the world and enslave us… AI is trained on the internet, on all of human history, everything we’ve written. So, of course, the tropes that it will default to, the well-worn patterns in AI thinking, are that AI behaves this way: it’s inevitably going to take over, it’s inevitably going to enslave humans. That’s just the script we’ve given AI. Of course it’s going to parrot that back to us.

John SmallMtn (04:32)

Mm.

Hillary Lyons (04:45)

But yeah, it’s really just a stochastic parrot. It is a dumb token prediction machine. It’s not as clever as we think. It doesn’t truly reason, understand, or empathize. So to your question, half my work is dismantling those myths before I can even start the actual work with my clients, because I need to help them understand where it will genuinely add value and where they’ve been led to believe it has these superpowers that aren’t even necessarily helpful to their goals. Why is doing things faster or producing more content better? I don’t think it is.

John SmallMtn (05:14)

Yeah, interesting. I have 500 different questions from that answer.

When you’re thinking sales side of growth for this business, one of the things I’m always talking about with people is the format of education versus the sales process and stuff like that. It sounds like there’s a fair amount of educating so that people can have the right expectations to be able to work with you and have it be mutually beneficial. Do you have any—this is a weird question—do you have any unique red flags after having enough conversations with people to where just how they say something or how they talk about something is a red flag enough to where you’re like, “Nope, I’ve got to go, we can’t work together, it’s going to be bad”? Do you have anything like that?

Hillary Lyons (06:15)

Yeah, it’s a great question because I’m learning a lot more about my audience—the actual roadblocks that they encounter, not just the ones I think they do—and the minimum requirements they need to have in place for me to be able to really deliver something of value.

Some big ones that stand out are if they are overly fixated on time savings or cost efficiencies to be gained through AI, because I don’t think the time savings are as great as anyone has led us to believe. I think they can be if you really have enough structure in place, if you know your systems inside and out and you can automate that, great. But if you don’t have that existing structure, expecting massive time savings is just unrealistic. You haven’t done the work of building the right processes, resources, and workflows yet.

John SmallMtn (06:25)

Mm-hmm.

John SmallMtn (06:45)

Hmm. Yeah.

Hillary Lyons (07:06)

So any fixation on time savings or how many people they could replace with AI, I just think that’s misguided and not what I’m here to offer.

Secondarily, to that point about having some kind of system structures, you need to know what good looks like internally and how to get to good before you can expect AI to deliver perfect results for you. I’ve been talking to a lot of my contractors lately where before, we’d be hired to write a blog on a certain topic. We’d try to capture the brand voice, learn about their audience, write an outline on that topic, and present it. They were deferring to us content writers and experts to deliver this deliverable. Whereas now, because we’re training these AI tools to write in our customers’ brand voice to empower their own internal team to write more brand-coherently, as I say, we need to understand from our customers first: What does a good paragraph look like to you? What are the constraints or requirements this blog should have to demonstrate it’s reached the level of quality that you want?

We need to document and systematize those processes—not only for my own internal contractors, but so that when we’re prompt engineering AI to write in this brand voice effectively, we have specific metrics we can point to: “You left out a call to action in this paragraph,” or “You did this, you didn’t do this.” Just like if you were training a human, you’d have to have those clear guidelines and scorecards to be able to effectively train them and improve their skills.

John SmallMtn (08:30)

Yeah. Have you run into anybody on the contractor side that you’re like, “Why are you trying to do this like the old way?” Have you run into resistance from people on your team or people that you partner with using the same tools the same way that you do? Or is that even a thing that you’re concerned about?

Hillary Lyons (08:53)

Hmm. Sorry, I don’t think I understand the question. Am I concerned about them?

John SmallMtn (09:09)

Yeah, that’s fair. Let me phrase it better.

As a salesperson and sales trainer, there’s the old version of selling, which is go anywhere, be anything, say anything. And then there are tools like Clay now, so you can be hyper-targeted and hyper-personalized. You can get a lot more done being strategic. A lot of my work is like, “Hey, let’s use these tools. Let me use the CRM. Let’s use process thinking to get more out the door.” Sometimes, because it’s a different mode of thinking, there’s a lot of friction in getting someone to change and to think about doing it differently. I would imagine—because I know some content people who were harshly anti-AI, like very much against it—that potentially you’re working with a partner on a project and they’re not using any of the AI tools or systems, and that might impact the quality or speed of the work.

So when you’re thinking about building out your agency, how important is it that the people that you work with are also thinking about AI as a lever and using it the right way? Do you have to train them in how to use it the way that you do, or are you allowing them to go be the artist while you use tools and AI to make their work better, without changing how they think about the work?

Hillary Lyons (10:35)

Hmm. Yeah, that’s a really good question because it’s been a very enlightening, messy, friction-full process. I’m only building out these broader-scale workflows, systems, and operations for my business for the first time in the past year. So it’s a mix of taking what we have and trying to make sense out of that chaos, trying to create structure from order—hence the name, Syntropy—or trying to build templates from best practices and then transfer over bits and pieces of what we’ve already done. Do we try to create structure out of what we have, or create the structure and then fill in the gaps with what we’ve already created?

I have my best practices for using AI tools, but the tools are changing all the time and there’s a new model every week, so it’s constantly in flux. I am the first one to say that I don’t think I’m an AI expert. I don’t think that my way is necessarily the only or the best way, but I’ve realized there’s just so much value in rolling up our sleeves and getting into the process.

So to answer your question: there are embedded team members of mine who I work with closely who are integral to my team, and I ask that they follow certain workflows and processes for using these tools just to ensure alignment so that we’re all on the same page. But I’m always asking them for improvements. If they come up with a better way of doing something or if they find a different tool that they like better for some reason, I encourage them to share because I want to know. I want to see what works for everybody, not just what works best for me. If we can achieve the same outcome by different means, as long as we’re adhering to the same standards—we have that scorecard, that vision of what good is, and we can all agree to it—I don’t care how they get there. But I do want us all to collectively share our learnings and figure out if we can find better ways of doing these things.

John SmallMtn (12:32)

Yeah. Interesting. Okay, I love this. I’m a believer that there’s craft in everything. But I also understand that we only really have room to appreciate craft in certain lanes. Whenever we talk about marketing, we always start nerding out about words, copy, content, and stuff like that. There’s obviously deep craft to doing that the right way.

This is kind of an aside of a question; it’s not really part of the main topic of the interview, but I’m just curious about your thoughts on it. When you think about the process of creating something creative for other people, there’s clarity, scoping, putting out work, and everything else like that. Is there a spot in that mode or linear format of working with clients that AI has been massively helpful in a way that you were not expecting?

Hillary Lyons (13:42)

Hmm. Yeah, that reminded me of something you said earlier, too. I have come to realize that I love writing, but I don’t know—I don’t consider myself a writer as much as I do a problem solver and a strategist. I love the craft of writing, but I’m not doing that for my work. My work is copywriting. It is writing with a purpose. I’m not here to draw attention to the words; I’m here to drive someone to a specific action. So I don’t think I get as offended as my writer friends do by AI.

I have really leaned into its benefits and applications in these other areas. The single greatest benefit of AI to me is that I used to be a ruthless self-editor. I couldn’t finish writing a sentence before I’d gone back to the beginning to swap out an adjective or tweak sentence structure. I was dedicated to the craft, but I was too in the weeds to see the bigger picture, especially for a first draft. You need to be at that 10,000-foot view so you can connect the dots between ideas and understand if you have a real argument or case to make.

For me, AI helped because I wasn’t writing the first draft—I was writing my thoughts to GPT. I could have a stream-of-consciousness style, get all of my thoughts on the page, and start playing with the ideas and running with that strategy and vision much faster than if I was getting bogged down editing myself. So the unexpected win of AI was helping me play in this strategic ideas space more, see further, connect ideas better, and go deeper with these topics.

The secondary sort of surprise or use case that’s been most beneficial is creating—like I said, I don’t expect magic out of AI when it comes to time or cost savings, but the real magic to me is this brand coherence, as I call it: this single source of truth for your business operations, brand identity, or whatever. I’m using Notion a lot lately to this end, where, yes, I’m using their generative AI to help me create copy or concept posts, but more than that, Notion has become my agency’s brain. Anytime we have updates on projects or client meeting transcripts, it’s all added to this organizational context we’ve built in our Notion workspace. So AI helps us stay up to speed on shifting client priorities and transcribe decisions we’ve made from meeting notes into their appropriate dashboards or tasks. It’s become such a central organizing hub for my business that I didn’t anticipate.

John SmallMtn (16:46)

That’s awesome. I’ve long been a believer in one source of truth. Being a CRM guy, obviously you spend a lot of time there, and the idea that AI can do some of that for you is fascinating because I hadn’t really thought about it in that way.

Now I would like to flip the question, because this is one of my favorite exercises to do. We talked about some unique ways that it showed up as helpful that we weren’t really anticipating. Was there a spot to where you’re like, “Oh my gosh, AI is going to change everything,” and then trying to enable it for that use case, you’re like, “This is the opposite. We’re not going to use AI in this until we figure out a better way to do it”?

Hillary Lyons (17:21)

Yeah, pretty much anytime I’ve attempted vibe coding or image generation. I’m just awful with it. I don’t understand it. I am a words person, so I’ll use that as my excuse, but there’s something to being able to see the output. The word “dog” is the word “dog”—there’s no confusion there. Whereas if I say, “Generate me an image of a Pikachu,” and then it gives me a style and I have to try to put into words what I do or don’t like about that style, there’s just so much more room for interpretation when it comes to visual media that I find it much harder to prompt.

I’d say also just for creative work in general, seeing how magically it spits out hundreds or thousands of words, you think, “This will make writing a breeze.” But anytime I go to long-form writing with AI, I need to spend about 90% of my time doing the planning work, and then the writing goes much smoother. If I just start with, “Okay, GPT, help me write a blog about this topic,” I find myself 12 hours later down a rabbit hole with no draft done because it’s not good at discernment. It’s sycophantic. It will “yes, and…” you and pull you down all these different rabbit holes, but it doesn’t know what is the right choice for your business or project. Only you know that, and unless you go in with a clear idea of what your goals are and how much time you’re willing to waste or not, it’s easy to let AI run away with you.

John SmallMtn (18:59)

I love that topic of conversation. Everybody wants to use it for the work that they aren’t good at and are probably putting at a commodity level as opposed to appreciating the craft. From my lane, that always ends up like, “Okay, John, I’m not going to try to write a great piece of outreach; I’m going to write 5,000 versions of it and send them to 100,000 different email boxes.” It’s like, or you could just go know your customer a little bit better and then you don’t have to stab at it quite as hard.

Let’s bucket this down and try to help some people. If a founder does not come from words and writing with intention—writing for a purpose in the form of conversion, which is copywriting—and I love the distinction between content writing and copywriting, because they are very different disciplines with very different developmental end goals around them—if they don’t come from this lane, they’re probably not going to use AI well the first couple of times. With it being so sycophantic and just pumping you up and “yes, and-ing” you into oblivion, what kind of advice would you give to a founder who doesn’t come from brand positioning and messaging about how to use an AI tool slightly more effectively than someone else who doesn’t listen to this interview?

Hillary Lyons (20:33)

I would strongly advise—and I work with a lot of founders in tech, so tech being their background—lean into that engineering background and mindset. Try to design the structure for your project or prompt before you get too in the weeds.

Before you try prompting GPT to help you write your mission statement, your elevator pitch, and all of your web copy, think of the component parts. What building blocks do you need to build a verbal brand or a brand messaging framework? You need your mission statement, your vision statement, value statements, and your differentiators. You can find countless templates online. I have some I’m happy to share as well. But think about the component parts you need, and then try to craft each of those component parts and understand how they fit together.

Versus if you just say, “Write my homepage. Okay, now write my about page,” then they all start blurring together and sounding really samey. Suddenly you’re lost and you don’t know what purpose this messaging served versus this messaging over here. Reverse engineer your brand, basically.

John SmallMtn (21:38)

I like that. I’m going to split a hair here because I’m curious about your thoughts on this. I’m a big believer in having it interview me, like: “What do you need from me to do a good job with this?”

I’m curious, do you think that is helpful for people if they’re trying to navigate a well of craft and they don’t have any depth of experience? Or do you still think there’s some onus on the founder, or whoever is trying to use this tool to shortcut this deep well of knowledge and experience? Is there still some onus on them that they need to be at a level of ownership? Or is doing the, “Okay, here’s an idea. Now interview me,” and having it iterate and walk through the process with you—do you think that’s okay? Or do you think that is limiting, not helpful, and not going to lead you to the path that you’re hoping to be on?

Hillary Lyons (22:38)

I think it depends on what your goal is. If you are at an ideation discovery phase and you just want to chat back and forth with GPT, Claude, or Gemini to brainstorm and get ideas on the page, that’s a very different kind of conversation than if your goal is to write high-converting homepage copy and you need XYZ.

I think being clear about your intention and your goal upfront, and knowing how much you need to direct the conversation if you want to drive toward that specific outcome, versus letting GPT interview you more casually if it’s still just an exploratory phase—GPT will take its best guess. It will use its token prediction powers to guess what kinds of questions it should be asking you. But again, it doesn’t have lived experience or human expertise. It doesn’t know your business as well as you do. Maybe you ask it to brainstorm 50 questions, select the 30 most relevant to you, and spend more time focusing on those.

My word of caution, no matter what kind of conversation you’re having with AI, is just be very mindful of the intentions you’re going in with: how much control or direction of the conversation you are allowing it to have versus who is in the driver’s seat, basically.

John SmallMtn (24:06)

Yeah, I like that. Who’s in the driver’s seat? That’s a great line.

I’m going back to a thing that you said a second ago, because I don’t want to lead people astray with this. I would imagine that there are some people who would show up and not understand that their homepage copy should be different than landing page copy, direct outreach copy, and stuff like that. The curse of knowledge is something I love talking about with people. If you’re not even at that level of knowing that you need to be very clean and clear, and that it’s different in different formats, can we trust AI to get us to a place of guidance so we can do it well? Or is it like, “Okay, you still have to go read some books and have some basic operating knowledge before any of these tools are going to be able to actually help you”?

Hillary Lyons (24:57)

Yeah, I have learned the hard way that it is better to pay for expertise where it counts. Sure, you can go read the books, teach yourself, and riff with GPT. It will probably take you four times as long to do as just hiring an expert to do the thing. But if you don’t have the budget for that, AI opens up so many doors for people. It’s allowed so many people I know who don’t consider themselves creative to do really creative, brilliant things.

It depends on where you are in your business, with your startup, or with your company. If you just started and you don’t have a clear idea of your persona, and you aren’t ready to invest a lot in brand development, perhaps you need to gather more data. Yeah, go build a lovable website for five bucks and throw something up to see how people respond. I think it’s better to publish something imperfect and start collecting data that you can use either yourself to improve the product or when you finally do hire that expert to help. You can say, “This is what worked, this is what didn’t, this is the messaging people resonated with, and this page didn’t get any traffic whatsoever.”

So yes, I firmly believe people working in their zones of genius produce the best work, and you can make compromises for speed or budget as you need to. But if you use AI as a tool when trying something new to just get a feel for it, it’s a great way to prototype things and learn from your experience. Then you can determine if you need to hire someone more skilled to help take that piece of content or website the final mile, or if you enjoy the process enough to continue learning and discover a new skill set.

John SmallMtn (26:40)

I love that answer. Which brings me to my next question. Writing is very subjective and can be very craft-driven. How do you think people—especially in the creative agency lane—should be navigating the inevitable conflict when your output does not line up with their output, and it leads to frustration or back-and-forth arguments? Are you seeing any of that happening where people are digging in, like, “No, we’re going to do it because my GPT said it this way”? Do you think it’s going to be a bigger problem, or do you think it’s just, “Humans are humans, client work is difficult, and there’s always going to be some sort of gap or moat to cover”?

Hillary Lyons (27:44)

I haven’t encountered that. You’re saying with other agencies, marketing consultants, or within my own team?

John SmallMtn (27:55)

When you’re doing client work for other people. Years ago, before I was even doing this, I was running an affordable website business. We were talking to a new potential partner who had been in design for a very long time. He shared a story with me that they had Blockbuster as an account. Someone in marketing from Blockbuster called them and started asking questions about how to do something in Adobe. A big bell was going off in the back of his head: “Why is my client calling me to learn how to use these tools that we’re using?”

He couldn’t really put his finger on it, but it led to, “Our team did this internally, and you did this.” It can lead to frustration, a lot of back-and-forth, and infighting. Agency work is prime for that anyway, because it can be very subjective in nature. Do you think AI is going to make that harder, or do you think it will be easier?

Hillary Lyons (29:05)

I think we’re going to have to catch up big time in terms of AI training and enablement—actually empowering people to use these tools, measure performance, and track success. Right now, tons of enterprise employees have their own GPT, Claude, Gemini, or Perplexity accounts, whether or not it’s officially sanctioned by their organization, and everybody is just free-falling trying to figure it out.

This goes back to my earlier point about getting our clients to give us their scorecard, their definition of done, and their metrics for evaluation. It does happen where I created a GPT for a client, and they were using it. We went back and forth a little bit because they really wanted to tone down the language so it was less flowery, less enthusiastic, with less emotion and fewer exclamation points. So I revised the GPT. Then they started using a regular GPT account on their own, not the custom branded one that I built. They sent me all this content they had generated with GPT that was guilty of all the things they explicitly told me they did not want. But since they generated it themselves, they were like, “Look at this, isn’t this so cool?”

I had to remind them, “I thought we said we don’t do more than one exclamation point in a paragraph. I thought we said that we try to avoid this kind of phrasing.” And they said, “Yeah, you’re right.”

All of these issues boil down to communication and values problems. If we can align everybody and say, “This is the list of must-haves in every blog post; can we all agree to this? Do we all like this?” then the next time the client comes to me with, “Look what my GPT came up with,” I can say, “Did you use our checklist? Does it meet our standards? No? Okay, let me go back to the drawing board.” Then it’s not personal or contentious; these are just the standards we’ve agreed to. They can change anytime and we can adjust them, but we’re both agreeing to uphold these standards in our work or to find tools and ways of collaborating that keep us on the same path.

John SmallMtn (31:25)

I love that. Most of my clients are coming to me because they’re trying to scale sales. One of the things I talk about is: we scale what’s working, and we scale what we know to be consistent. A lot of people want to scale sales because they have not been successful in sales themselves. They start thinking, “If I just have a team of hunters, it’s going to change everything.” In some areas that’s fine, but if you’re doing something custom, creative, or subjective, you really need to slow down and make sure that there’s actual deep alignment.

That’s where I’m always like: you can’t completely automate the process if you have concerns about client selection. You need to have a Gandalf standing on that bridge protecting the hobbits from the monsters. It’s funny, because people are like, “You just have to make do with whatever clients, and you charge them more if they’re bad.” And I’m like, “No, you could just say no to those people.” But it’s a hard move if they haven’t gotten to that tier, because you have to have some bad clients before you can really appreciate the good ones, and people don’t appreciate that when they start.

This brings me to the next topic. The thing that got me super excited to have you on here was that you started out not trying to run an agency. You were trying to freelance, do your own thing, and help clients. We were talking about this shift from it just being you to being this bigger thing. Can you talk a little bit more about why you would even want to put in the effort to try to build the bigger thing?

Hillary Lyons (33:10)

Yeah, I’d love to. The past six months have been the most rewarding of my entire career, and it started the moment I decided to rebrand and treat my business as an actual business—not just my freelance hustle, or me and a friend doing some content writing here and there.

I started out as a food and wine copywriter. Before that, I was working in restaurant kitchens—very blue-collar, unglamorous work. I’d always loved food and wine, and food and wine writing in particular. When I first started freelancing, I was drumming up small gigs here and there. I live in wine country; there are lots of small local wineries doing cool stuff out here. For years, I liked my independence, my freelance hustle, and the freedom to spend my time when and where I choose.

I knew that my ability to scale was going to be limited by my manpower—by my waking hours, basically. Looking back now, all the things that I was afraid of turned out to be not at all what I expected. I was afraid that if I scaled to an agency versus being a solopreneur, I would spend all my time managing people and wouldn’t have time for the client work or the writing that I love—that it would just be all people politics and management. Now, that’s my favorite part of the work. I love providing feedback, training others, and managing my team. I have so much more time for the creative and the strategy because I’m not bogged down in the weeds with the day-to-day execution.

It took years of finding my footing, getting better at setting boundaries with clients, and many small lessons before I felt ready to take that leap. But it’s been profoundly helpful, not just financially, but psychologically. There’s this distance now between me and the work because there’s this larger business entity that we all owe the great work to, and that we’re all actively striving to improve. It’s really rewarding. I could go on and on, but I’m curious if you have specific questions.

John SmallMtn (35:34)

I’m a big believer in the fact that we often stand in our own way, and we often cherry-pick the obstacles that lay in front of us to not go down a lane. In my own background, I always had good reasons for the things that I didn’t want to do, so I thought that meant I didn’t have to go do those hard or difficult things. I always had an excuse. Then, coming through sales training and on the back of martial arts training, I realized that these are excuses—and reasons and excuses are the same thing. How often are we using them because we’re not hitting our performance marks? That’s when things started to change for me.

Now, I love the line: “The thing that makes you most uncomfortable is probably the thing you should be focused on.” Going back to your mode of, “I don’t want to be lost in politics, managing a team, and managing people,” do you think you have shifted, or do you think that was just looking for reasons to not do the harder thing?

Hillary Lyons (36:45)

I think it’s a bit of both. Certainly, there was a lot of pushing things off because it would require a complete overhaul of my systems, my tech stack, and how I do things. Building out every SOP and template felt monumental and way too intimidating to even start. It felt like, “Well, who am I doing it for? Just for me? I could just sit here and keep doing this thing. This is fine.”

But it wasn’t. Partially, the rebrand really lit the fire under my ass because so much had changed in my business, but I hadn’t manifested that with a new look and feel or with new messaging. I love writing and content marketing, but I didn’t feel as passionately about it as I do AI marketing, or more specifically, empowering people with these AI tools—because I think they’re such incredible, innovative resources.

Now I genuinely feel impassioned, like I have this message to share with the world. I know I can make people’s lives better by sharing this, whether or not they work with me. Even if they just pick up a free resource and start using this thing, that energizes and excites me. Now I feel like I owe it to the world. I’m compelled by this force to share it with people. It’s not just me and my little side hustle.

John SmallMtn (38:03)

Thank you for the depth on that answer, because this is hard. If you’re only doing it because you think it’s going to be easy because of some article you read or an assumption you hold, you’re not going to do the hard things. You’re going to try to think, “How do we make this hard thing easy?” Sometimes you just have to commit to doing the hard thing. What a great answer, because it’s all hard, but you have to choose your hard.

The idea that it was easier to procrastinate and not do some of the hard things because it was just for you—that’s a unique perspective. I used to have a coach who would say this line—and I hated this line, Hillary—he would say, “Is it a business, or was it a hobby?” I hated that line. He would use it as a weapon, so he was probably using it a little too harshly, but there is a difference there. If this is for something else—if this is for the people on your team or the people that you’re serving, and it’s not just, “Well, I don’t want to go work for someone else”—there is a difference in how you show up.

That’s an interesting thing, because I tell everybody: if you can’t conceive of working a full day with clients on this idea, are you going to go sell it? No, absolutely not. You’re going to try to find a way to build a funnel with an offer so you don’t really have to do anything, and you’ve already missed the thread, in my opinion, if you’re trying to do it that way.

I think it’s really cool that you waited until you did get excited about it, because some people will do a “fake it till you make it” kind of thing. They’ll tell themselves that they need to be this excited about it, but it’s not real. I don’t know if you ran into that with people that you worked with, but as a sales coach, you see it pretty quickly whenever it’s like, “Okay, you’re saying these things are important, but your actions are not lining up with what you’re saying is important.” We can only do this song and dance so many times before we have to be honest about it. Fascinating. Okay.

Hillary Lyons (40:11)

I really liked your point that it’s going to be hard, so pick your hard. Life and work are already difficult, but if I choose a difficulty that is going to challenge me, make me grow, and make work interesting, that’s a job I’m happy to show up for every day.

John SmallMtn (40:34)

100%. When I was kind of stuck, whenever I was selling in corporate and wasn’t bringing my whole self to work, I was expecting it to be easy. I can speak from this experience of not putting my whole nerdy, deep, obsessive self into this lane. I was like, “Well, this is just my job. I shouldn’t have to take it this deep.” Now, I’m on high alert for that because we can’t get anything done if you’re expecting it to be easy. The first conversation with everybody is, “Is this even worth it?” If it’s not worth it, don’t even try to sell yourself on the fact that you’re going to do the hard stuff. You’re going to pivot, and then you’re going to be something else.

Being online, we see these people who were something for five or six months, and it wasn’t easy enough. It wasn’t effortless, and then they’ll reinvent themselves over and over again. I feel bad for those people because they’re drinking Kool-Aid that if you find the right thing, it will be easy. No, it just doesn’t feel like work in the same way that it did before when you weren’t aligned. It’s one of those splittings of the hair that is hard for me to communicate with people, but I love how you’re talking about it. I get to do this. It’s the hardest thing I’ve ever done for sure, but I’m excited by it every day and every week, even when the weeks are kind of meh.

Hillary Lyons (42:16)

Quick caveat, I’ve worked in my fair share of toxic startups that expect everyone to drink the Kool-Aid and love working until 8 p.m. I’m the type of person who can’t work a job that I’m not completely absorbed in for all the hours that I’m in the office. If I’m just sitting around on my phone, why am I even here? But I know that I don’t expect everybody to want that. Everyone has different priorities, and if you like to clock in, do your job, and then check out, that’s cool too. But I need to build something that will constantly challenge me.

John SmallMtn (42:37)

100%. I love that you said that because one of the things that I’m always railing against is: this is your baby. No one else should come in as excited or as bought in about your baby as you are because, ultimately, if you’re paying them and they don’t make the cut, you’re going to fire them, and it can’t be their baby anymore. The whole “we’re a family” leads to a bunch of weird relationship dynamics that shouldn’t exist in a business. The way that I think about it is the job of the founder is to create jobs that are easy to come in, work, and go home from, so that way you don’t have to try to get people on some life’s mission and hope that it’s yours. It just doesn’t make any sense, but people keep trying to do it. It comes from this idea of, “You’re supposed to be as excited as I am.” No, they should be excited to come in and do their job, but not to make it their life. There is a big gap between those two things.

Thank you so much for bringing that up because it’s a very hot topic for me, especially on the sales side. Sales and marketing founders love to bring people on and saddle them with huge, unrealistic expectations. Then when they don’t make the mark, they just get let go. There’s an opportunity cost for us as salespeople and marketers, because if you jump around, now you’re a job hopper and no one will talk to you. It’s tough, because you have to think about the other people involved. Do you really need this thing, or are you trying to abdicate the ownership of this thing because you don’t want to do it or you don’t see yourself as good at it? Both are okay, but you need to know where you are on that, because otherwise you’re going to hire badly and just be frustrated the whole time. Sorry, I got a little excited about that one.

Hillary Lyons (44:30)

No, I appreciate that rant.

John SmallMtn (44:30)

Honestly, I’m not talking about this on camera, but that was the first version of what this show was going to be: around the idea of stop bringing on people who just want a job and trying to saddle them with partnership-level expectations. That’s crazy, but I realized it was making me angry. So we had to shift the show, and now it’s this, which I feel much better about.

Hillary Lyons (44:43)

Entrepreneurship is not for everyone.

John SmallMtn (44:59)

It just bothers me whenever people are not thinking about what happens if this experiment that we’re all excited about and got sold on doesn’t pan out. Are there jobs at risk? Is other people’s ability to earn and have consistency in their livelihood at risk? We should be more thoughtful about it, and sometimes we’re just not, which bothers me.

Okay, so I want to be super respectful of your time. I have a couple of questions for you, and these are more of the rapid-fire stuff to try to help people out. My first question is specific to your lane: when it comes to AI, marketing, and messaging, if you’re a brand-new founder, what is the advice you would give someone before they sit down at ChatGPT and say, “Help me”? What would you steer them towards? What advice would you give them?

Hillary Lyons (45:44)

I would say come check out my website when it’s live. I’m going to have tons of custom GPTs—brand-agnostic GPTs trained to help you with specific types of messaging, like developing your ideal customer persona or identifying your positioning strategy based on competitor analysis. My goal is to break these tools down into modular, bite-sized pieces that act like exercises founders can use to quickly develop a bare-bones, V1, first-pass positioning strategy, unique value proposition, or what have you. To that end, don’t just say, “Help me with my brand story.” Find a proven framework, template, resource, or expert out there, and then work with GPT to apply that framework to your business, because that will produce much better results.

John SmallMtn (46:46)

Real quick, there’s a bunch of frameworks out there. Are there any frameworks that you’re especially a big believer in?

Hillary Lyons (47:00)

I think you’ll like this one: the StoryBrand framework for telling your customer journey. It puts the customer as the hero of your product journey, not yourself. A common mistake that many startups and most companies make is they make their About page entirely about them, which makes logical sense, but your About page should always be about your customer and how you help them solve their problems. The StoryBrand framework uses that to position your customer as the hero and you as the guide who shepherds them on this journey to transformation. I think that is just a really good exercise to get out of your own founder head about your business, because we can get so locked in it, and put yourself in your customer’s shoes.

John SmallMtn (47:37)

This is so funny because I have such a visceral, polarizing, opposite belief about the About page. The About page for me, as a sales professional, is my last line of whether I’m going to do an outreach or not. The ones that are too “here’s who we help, here’s how we help,” and everything… Some people wouldn’t like this, and a lot of sales bros are going to roll their eyes at this, but I work for myself and you work for someone else, so it’s fine. If I read that About page and it doesn’t feel like it’s actually connected to the humans, I don’t do an outreach. If it’s too tilted towards the customer story, I feel like it’s just a marketing website and it’s not actually authentic, so I won’t do outreach. I’ll just go find someone else to talk to. Interesting.

Hillary Lyons (48:33)

Sure. All of this advice varies so much by industry, business type, and whether you’re a personal brand versus a business with its own eponymous brand.

John SmallMtn (48:47)

That’s fair. Zooming in, because this is for people who are new to this, I’m not saying everything should be “I” starting statements and stuff like this. It should be at least slanted so that it tells a great story and talks about why you’re in this space. If there’s nothing on there about why this matters, I’m out. I’m not doing anything. That is important. I’m not saying to completely go the other way, but if it’s too perfunctory or too markety, I just think that no one’s really authentic or really caring about it, and I’ll just move on. Typically, that leads to more transactional thinking on sales anyway, and that’s not really the kind of selling that I teach or see a lot of value in. Interesting, though.

Hillary Lyons (49:41)

Yeah, you’ve still got to load it with personality. You’ve still got to make it signature to you. A lot of startups, especially, on their About pages list all their credentials, all their certifications, where their founder went to college, and how they made all these cool features. Hypothetically, the customer cares because it’s social proof that you have won these accolades, that you are secure, and that you have all this expertise, but they don’t want to read your resume. They want to know how you’re going to help them.

John SmallMtn (50:14)

100%. We’re probably closer in the middle if we zoom in and look at this, because it shouldn’t be your MySpace blog either. Sometimes I see that and I’m like, “You’re not ready.” I appreciate the distinction there.

With all the social media stuff, everyone talking about dogma and posts, and everyone having hard opinions on everything—when you think back about the popular wisdom of running a business and being a founder, what is the tweet or mantra that you appreciate now that you couldn’t appreciate until you had to learn it the hard way?

Hillary Lyons (50:47)

Something that I repeat to myself multiple times a day is “progress, not perfection.” I am a die-hard perfectionist and recovering people-pleaser, and nothing will wreck your brain’s sanity like working in tech startups, because it’s operating with so much uncertainty all the time. At least now the uncertainty is mine; I’m the one who’s got to make the agency decisions, and it’s not just me waiting on someone else’s call.

I’ve had to learn to live with so much uncertainty, publish things, learn from the data I collect on that content, and use it to improve the next time. I wish I’d started writing more prolifically much sooner, because I can see myself improving so much faster now that I do it every day for my personal LinkedIn, my journaling, or what have you. Really internalizing that and acknowledging nobody’s going to judge you as harshly as you think they will—and probably not as harshly as yourself—it’s more important to get the work out there so you can keep growing and learning with it.

John SmallMtn (52:02)

100%. I’m so thankful that you brought that up, because I think of writing as a core developmental thing that most people are nervous about. For me, one of the things that was super important was divorcing myself from the need to edit while I’m in creative mode. I have a habit of, “Well, I only want to do it once, so I’m not going to write anything until I know it’s going to be good,” which is really just a great way to procrastinate. I honestly don’t believe we would have gotten the book out if I hadn’t been able to work with my wife, who is my editor, so that I didn’t have the pressure of it having to be perfect on the first stroke.

Now, using AI, since I’ve already broken myself of that mode—where I’m great at the ideas and okay at the shaping, but the final touches have never been my strong part—it might have been easier for me to use AI in some of the ways I’ve been thinking about, because I don’t have that need to be the first, middle, and last part of it.

I’m detouring massively because I’m curious about your thoughts on this, but I saw this post where a person was talking about how they needed to step away from AI and GPTs because they were seeing signs that it was limiting their creative muscles. Do you think that is something that people need to be concerned about, or do you think that it’s inevitable and it’s more about knowing the frameworks? Has that shown up for you at all? Do you feel your creative drive shifting?

Hillary Lyons (53:50)

Super timely that you mention that, because I saw a similar post and got into a conversation with my partner about it. I found the exact opposite to be true. I feel more creative now that I have AI in my life. Because I’m not so self-critical, instead of spending 30 minutes editing the same paragraph, I get the paragraph out, riff with GPT for another 10 to 15 minutes to refine it, and then I have a V3 paragraph that is much better than the self-edited one I would have agonized over for 30 minutes alone.

It’s separating out… I’m realizing how much more I was doing than I was giving myself credit for. A lot of copywriters aren’t just writing copy to sell a product; they are helping the founder develop that product, helping them outline what’s included and what isn’t, helping them A/B test messaging, and helping them get into consumer psychology. There are so many layers to it. It’s not just writing a great headline or email. Now I’m able to separate the craft—the final polish and writerliness of it—from the ideas and the creative. I’m able to tackle each of those component parts more directly and spend more time polishing it into something beautiful, instead of emphasizing the polish and beauty upfront and getting so caught up on that that I couldn’t even progress on the words.

John SmallMtn (55:15)

I hold it the exact same way. It’s like a bad ego battle about things that you don’t even need to be arguing about. If you’ve got good creative drive, discipline, and habits around consistency—just challenging yourself to sit down even when you’re not motivated or inspired—then having a good filtering or editing mechanism is more valuable. I saw that post and read it, and I was kind of like, “Huh, I wonder if that’s happening to me?” Then I was like, “Well, if anything, I feel like I’m more prolific now than when I was just writing stuff and giving it to Melissa, asking, ‘Is this anything?’ and she’d be like, ‘No, this is nothing,’ and I’m like, ‘Okay, great, no big deal.'”

Do you think that the craft of writing should be more focused and tilted towards discovery, ideation, and beating back that critic to get into that loose, free-form, free association where good ideas come from? Or do you think people still have to be able to put that finishing touch on there, running it through the end processes so that it fits the framework, fits the idea, and does the thing? Or do you think, “Don’t even concern yourself with that; why would we do that?”

Hillary Lyons (56:52)

LLMs in general have made it super clear that we consider only the final, finished product as writing. You’re only writing if you’ve published something or produced X number of words, whereas I could wrestle with my ideas for hours and not put a single word on the page, and that was still really deep, productive work. We need to celebrate that process more. We need to reward the friction and discomfort that is necessary to spawning great ideas or creative works, and recognize that has to happen outside of a conversation window. Sure, you might be chatting with GPT to help you flesh out those ideas, but you’ve got to do that messy work internally. That’s fruitful, good, and positive in its own right, even if it doesn’t yield anything immediately.

John SmallMtn (57:43)

100%. This is awesome.

Hillary, last question, and then I can let you go for the day. I really appreciate you coming in and doing this, by the way. When you’re seeing everything that is now happening, and you have your experience in the lanes that you do, having made the shift of starting smaller and realizing that this is the better lane for you—what’s the one piece of advice you would give someone who’s starting today?

Hillary Lyons (58:15)

I think that passion is important, but overrated. You don’t have to have it all figured out to start something. The best lesson I’ve learned, that I’m going to start advocating for all of my startup clients—early-stage startups especially—is: publish a website you know you’re going to hate, and live with it for a month or two. Again, just a lovable, quick mockup, because you learn so much through the process. When I wrote my initial web copy six months ago, I thought I was going one direction. Now that I’m finally publishing this website, I went back and looked at all of that copy, and none of it was relevant to where I am today. There was a lot of stuff that I could build on, but so much had shifted. I have so much more clarity on my business six months into this rebrand.

So again, progress, not perfection. Just get started, figure out what energizes and excites you, and pursue that thing. It may still feel like work, but it’s work that you’ll enjoy doing, and you’re going to grow and learn so much in that process.

John SmallMtn (59:31)

Epic. Okay, I lied. I have one more question because that was such a cool answer. I’ve had to adopt this thinking because I am, by nature, high quality—I want perfection and a good thing. I’ve had to build some tricks and habits to not get stuck in those modes. Have you found any tricks for yourself about avoiding that procrastination-until-perfection thing in your work now? Do you have any tools, tips, or hacks that help you stay focused on moving things forward and putting it out to get feedback, as opposed to waiting for it to be perfect?

Hillary Lyons (1:00:15)

Two things really help. One is very low-tech: I just get my notebook out and start manually writing things down when I can’t type it out, when my head is all jumbled, or when I feel really lost. I just return to pen and paper. If I set a timer for five minutes and write as much as I can think of about what’s going on, it helps me tremendously. Nowadays, sometimes I’ll even just talk it out, use that transcript, feed it to GPT or Claude, and ask it to help me come up with a game plan: “Help me overcome my procrastination. I’m really stuck on XYZ. How should I approach this?” Again, take everything with a grain of salt, but at least it gets you thinking, and suddenly you’re in dialogue with someone. It’s not just you alone with this monumental project looming overhead. Sure, that someone is an AI bot, but it can help you get unstuck.

The second thing is, I used to push myself so hard, as if adding more pressure would make me break through the challenge—like, “I’ve got to write this page by the end of today; I’ve just got to stare at it until inspiration strikes.” I’ve realized the flaws with that method. If that is the one task I have to do, I try to approach it from different angles. Instead of starting with the H1, why don’t I start with the calls to action and figure out all my buttons for this page first? That can sometimes help by tackling the easier, smaller thing or the avenue with less friction. Or, if I have to work on that project, but there’s a different type of task I can do—like, right now I’m really not in a creative space, so maybe I can do a little research and strategic stuff first to prime me for that. Shifting gears, changing perspectives, pen and paper—those are my go-tos.

John SmallMtn (1:02:04)

I love that pen and paper is my go-to default. If I start to feel like there’s too much in my head and I can’t think about what needs to be the next priority or what the trade-offs are of prioritizing something else, pen and paper is always right here. It’s so helpful in that mode.

I love that you said that, because there are all these tools now. One of the coolest things that I think people are not using AI for, but I wish they would, is leaning into reflective practices: “What actions did I do today? What did I miss today?” It means you have to interface with it differently and build it out differently, but it took four or five years of working with a sales coach in a performance coaching environment before I would even swallow the hard medicine of looking at my actions—not just talking to myself about these things, but actually documenting them and looking at how my time is being spent. AI lessens that learning curve, but because of how enabling and positive it is, you’re probably not going to get that latch of how important it actually is to you.

Hillary, thank you so much for doing this. I really do think it’s going to help some people, especially in the AI space around marketing. I’m seeing everybody just run over and say, “Hey, give me some marketing,” or “Write a social media post for me,” and thinking that’s going to be the answer. I really hope this helps people try to figure it out. If they want to come hang out with you, learn more about this stuff, or see if you can help them launch or grow their business, where should they go?

Hillary Lyons (1:03:53)

You can find me on LinkedIn. I’m always ranting and raving about new AI tools or misfires, and always sharing resources and toolmates like I described. Toolmates are just what I call custom GPTs, Claude projects, or any sort of branded bot across all of those main LLMs. I’ll also be launching SyntropyMarketing.com—that’s S-Y-N-T-R-O-P-Y marketing.com—very shortly, hopefully within the next couple of weeks.

John SmallMtn (1:04:22)

Awesome. All right, everybody, please go check her out. She’s always posting and talking about cool things that are happening. Her content is really good, and her workshops are really solid as well. If you’re interested in AI for growing your business, please take a look at the website whenever it’s up and out.

Hillary, I really appreciate you coming onto the show today. The depth here is really going to help people find their lanes and not stay stuck. I think it’s really cool. Thank you so much for coming in and slowing down so we could get to this depth.

Hillary Lyons (1:04:50)

Yeah, thank you for having me.