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  • 🦉 Issue #39: The Future of Generative AI Marketing with Jarie Bolander

🦉 Issue #39: The Future of Generative AI Marketing with Jarie Bolander

Actionable strategies for creative professionals.

✨ Personal Update

I’m really excited about some big news to share soon. Stay tuned!

Next up is my friend, Jarie. He’s a no-nonsense, straight-shooting Gen Xer and I always enjoy our conversations.

🌟 Meet the Guest

About Jarie Bolander:

Powered by a steady dose of locally-crafted espresso, I love nothing more than to figure out how to explain complex things in clear and compelling ways. My goal is to help build a more ethical, inclusive, and resilient world by educating and inspiring the next generation of entrepreneurs -- be they 18 or 80.

📝 Overview

Here’s what we talked about:

  1. Early Realizations and Applications of AI: Jarie's initial "aha" moments with AI came from applying machine learning to logistical challenges, leading to significant insights into AI's potential to automate complex tasks. His engagement with ChatGPT further revealed AI's capacity for data analysis and synthesis, underscoring its value in business strategy and decision-making processes.

  2. Generational Perspectives on AI: The conversation reflects on the unique position of Gen X, blending technological fluency with rich life experience, allowing them to leverage AI effectively. Jarie criticizes the skepticism towards AI among some peers, emphasizing the need for a growth mindset and the importance of discerning quality work, a skill that comes with experience.

  3. AI's Impact on the Startup Ecosystem and Job Market: Jarie notes the proliferation of AI startups and its role in enhancing efficiency within the startup landscape. However, he cautions about the potential displacement of white-collar jobs by AI, highlighting the importance of adapting to and integrating AI into workflows while developing non-automatable skills.

  4. Creative and Entrepreneurial Opportunities with AI: The discussion explores AI's untapped potential in creative entrepreneurship, particularly in customer discovery and product development. Jarie suggests that AI, through synthetic data and role-playing, can significantly streamline market research, offering a more objective assessment and facilitating rapid iteration of business concepts.

  5. Future Vision of AI Integration: Looking ahead, Jarie anticipates a world where AI is deeply integrated into all aspects of work, serving as an assistant that streamlines routine tasks and empowers strategic and creative endeavors. He foresees challenges, including increased "noise" and the need for professionals to differentiate themselves. Yet, he remains optimistic about AI's capacity to enhance work and life quality, allowing for a focus on creativity and innovation.

Overall, the interview portrays a nuanced and optimistic view of AI's role in society. It highlights both the transformative potential of AI in enhancing human capability and the challenges of adapting to a rapidly changing technological landscape. Jarie's insights emphasize the importance of leveraging AI to augment human creativity and strategic thinking, rather than seeing it as a replacement for human effort.

📝 The Transcript with Analysis

The Genesis of AI Revolution: Early “Aha” Moments

Jarie recounts his journey through the early days of machine learning, highlighting his pivotal “aha” moments that signaled the potential of AI. Initially applying machine learning to logistical challenges in the medical industry, Jarie quickly recognized AI’s capability to automate complex tasks. His encounter with ChatGPT marked a significant shift, revealing its power to analyze and synthesize data efficiently. This revelation led him to embrace AI for business strategy, appreciating its ability to process information at scale and significantly cut down on manual analysis time.

J.: What was your “ah-ha” moment? When did you realize everything was about to change?

Jarie: I’ve had a couple of “aha” moments that started almost ten years ago, and that was when this stuff was called “machine learning,” not AI. Basically, it was trying to figure out how to model things and modeling physical behavior in the real world, like how things behave. Super hard. One of the very first things I tried to apply machine learning to, which again is kind of the precursor to AI, was trying to figure out when things would be picked up and dropped off from a location. We had a delivery app, for lack of a better word, at one of my companies. I was trying to figure out the best way to teach the machine to know that something’s been dropped off and picked up automatically—this was for the medical industry, for clinical samples, blood, tissue, urine, etc.

It was in its infancy, but the “aha” moment was, “Holy shit! I can buy an off-the-shelf modeler, throw stuff into it, and gets pretty close.!” I had to do custom code, but I’m like, “Oh, huh, this is kind of interesting. This is almost there.”

While I was at this company, we were at a startup accelerator called 500 Startups. There were a couple of companies that were doing machine learning as this startup thing. One of them was called MonkeyLearn, which is a great name, right? MonkeyLearn, ML. They told us, “We have all these custom models, but we’re building an engine so you can customize your own model.” Now fast forward eight years to where we are today.

The other “aha” moment was a year ago… maybe a year and a half ago when I first started playing with ChatGPT. My use case was not generative. At the time, the writing was shit—twelfth grade, freshman college level, if that. It’s not that great, but the thing that I was using it for was analyzing data. I had all these surveys, I had all these websites, and I had to synthesize the messaging across sites. It was surprisingly good at that. It was like a junior analyst. I could just throw stuff out and it would nail it. I do B2B sales, marketing, and consulting for a living, and the biggest pain in the ass is synthesizing input and competitive analysis, sifting through a bunch of data to figure out what it all means. This new junior analyst did that for me in an afternoon which would have taken me days, if not weeks, to figure out. I’m just like, holy shit, I need to learn this. And since then I’ve been building standard operating procedures that use AI to help us analyze and understand and synthesize the huge amount of data so that we can then make intelligent decisions on it. For that, it’s just been awesome. Lately, it’s been a little slow and clunky, but overall, it’s saved a lot of time.

J.: It sounds like the real leverage for you is doing what you were doing before, but at volume and a lot faster.

Jarie: Oh yeah. To me, anything that’s rules-based and that you need to synthesize, summarize, analyze, and make some conclusions on—it excels at. Creating a blog post, writing a book–it just sucks. It’s just horrible. It comes up with the same stupid tropes. But the thing that I think is what you mentioned, volume. All that analysis, all that grunt work took away from the real deep thought. So, now that I have the ability to synthesize, summarize all this data that I have to look at in a way that reduces my cognitive load, I have more time to think about what it means, because you’re on a deadline.

I’ll give you a great example. I downloaded a bunch of reports, industry reports, case studies. Am I really going to read 150 pages of case studies? No. I mean, even if I read them, I’m scanning them, right? What I’ve found is that I will scan them, I’ll put it in the bot, and I will ask the bot questions. Then I can synthesize the answers. I’d say it’s probably saved me, in some tasks, fifty to seventy percent of the time. I think the output’s much better. It’s more consistent and much better.

Bridging Generational Tech Gaps: The Gen X Perspective

Jarie discusses the unique position of Gen X in the AI landscape, emphasizing the blend of tech savviness and life experience that sets this generation apart. He argues that understanding what constitutes quality work, a byproduct of pre-AI experience, is crucial for leveraging AI tools effectively. Jarie also addresses concerns about AI’s impact on creativity, arguing that true innovation will stand out amidst the increased volume of AI-generated content. He stresses the importance of embracing change and the opportunities AI presents for enhancing personal efficiency and creativity.

J.: We’re the same age, and we’re not going to reveal what that age is… Let’s just say we grew up on neglect and hose water.

Jarie: There you go. That’s all you got to know about Gen X.

J.: We have experience prior to the creation of these AI tools. We know what questions to ask, and we know what sort of analytical summaries we want them to generate. But what if you are the junior analyst? What if you’re twenty-three, and you’re fresh out of grad school, and you haven’t manually done these kinds of things before? Is there a downside to having ChatGPT doing it for you?

Jarie: That’s a really astute question because one of the reasons why people like us are going to be wildly more successful with these things is because we know what good is. I can objectively tell you, “This is shit. This is not shit.” And that’s because I’ve got the experience of doing it manually. I’ve put the deep work in. If I’m twenty-three, twenty-four, and I’m using these tools, and I don’t know what good is, or I don’t have someone to tell me this is what good is, I don’t intuitively know I’m going to go down a rabbit hole and generate total shit.

It feels a lot like when computers first came out. You probably remember the Apple II. It didn’t really replace the manual processes, but you could tell it was heading that way. You no longer needed typist because you just typed on the computer. Same with the internet. I remember when we were building the internet. I was part of that, no joke, and it was just fascinating to see the speed at which things could go horribly wrong and then things could go horribly right if you knew what you were doing.

For example, if you’re a writer, you should write longhand just so you can physically feel what good writing is. You should copy the great works, and you should copy the great works by hand because that’s how you learn. It’s like you’re in a band and you’re playing covers. That’s how you learn to be a better band. You just got to know what good is, and that’s hard, man. It will lie to you.

J.: I don’t know if it’s a paradox, but it really is an interesting observation. I think I’m biased, but I think Gen X is perfectly positioned right now to have a mixture of a native approach to technology combined with wisdom and life experience that I think maybe some older Millennials have. I think Boomers aren’t really native tech in the way that we are. Yet, generally speaking, Gen X doesn’t seem really interested in AI right now. A lot of my friends and peers—at best they’re ambivalent and at worst they’re avoiding it. Do you have any thoughts on that? Are you seeing that in your circles?

Jarie: Not in mine, but I’m in Silicon Valley, so everyone’s a tech bro. Actually, that’s not true. My artist friends, the friends that are writers and actors and people that create art, just hate AI with a passion–it’s like visceral. “Why do we need to be more efficient?” and I’m like, what are you, a luddite? They are fearful, and it’s just not rational.

“Creativity is gone.” You could probably go all the way back to the printing press. “Oh my God! Anyone can print anything? Oh my God, this is going to be chaos.” And you’re that much of an asshole to think you’re the source of truth? It’s bullshit. Adapt and overcome.

The true artist who knows how to create is going to accelerate—up their game. Because now, mediocre people can do what you used to be able to do easily. Now you gotta rise above the noise. So, for me, the level of noise is going to go up. This is my hypothesis: The level of noise is going to go up for the true artists, the true writers, the true creators. They’re going to stand out and they’re going to know what they’re doing, and that’s what people need to learn. Yes, you need to learn how to drive the tools, and yes, you need to know about the output. You’re going to be more efficient, but you got to know what good is, and if you don’t know what good is, you’re screwed. I think the people that I know who are afraid of it don’t have the inclination, or they’re not tech people. I just love this stuff. I love any innovation. It’s literal magic to me. I’ve been that way my whole life. So for me, it’s like, how can I use this to get better?

The people who I know in the tech industry are like, “Okay, how do I use this to make me better?” The ones that are afraid of it don’t have that growth mindset. They’ve been doing the same thing for thirty-five years. “What the hell? Why do I have to learn something new?” I’ll be learning something new until I’m dead—it’s part of the gig, man.

This is just going to accelerate what I can do. I can create better things faster, and I can understand things quicker, and I can use my cognitive energy to be more creative and not less creative.

AI’s Ripple Effect Across Startups and Industry Jobs

Jarie offers insights into how AI is transforming the startup ecosystem and broader business practices. He notes the proliferation of AI startups and the critical role of AI in streamlining operations, from content creation to customer service. While highlighting the efficiency gains, Jarie also cautions about the potential job displacement in white-collar sectors. He underscores the need for businesses and individuals to adapt by integrating AI into their workflows and developing skills that AI cannot replicate.

J.: You mentioned Silicon Valley, and I know that you’ve been in the startup entrepreneurship world for a very long time. Can you give us a lay of the land on how AI is affecting startups and entrepreneurship? I’m not talking about AI startups, I mean, how is any startup starting to use these tools?

Jarie: Yeah, it’s a land grab. I don’t know how many AI companies are popping up everywhere. It’s like, just because you got AI in your name doesn’t mean you’re doing AI.

Broadly, what I see applies to all businesses because this is a disruptive thing. Startups now have a tool that can accelerate some of the mundane things that they hated to do. That’s why you see all this crappy content being created, like, “Oh, we can generate a thousand blog posts in a minute.” And you’re like, yeah, it’s all shit. It’s clickbait. It’s like what they used to do when you used to have those summary pages where you just steal headlines. It’s intellectually dishonest, but startup folks, when they’re in the early stages of their company, don’t even give a shit about marketing. They’re like, “I just got to build this thing, and how do I get anyone to look at it?”

I think it is an enhancer for small to medium businesses once they get over the hump of finding a partner that can implement it properly. That’s the biggest challenge right now. No one really has a good way to implement AI for the small to medium business so they can just use it without having to learn. That learning curve is super steep. You’re going to see more and more of that. Big, massive companies, like enterprise-level companies, they are starting to realize that there’s a lot of manual rules-based tasks that they don’t need people to do, and it’s going to affect white-collar workers more than blue-collar workers. I could see it impacting accounting, support, marketing, sales, SDR, sales development reps… I wouldn’t be an SDR now. The good ones are really good, but if you’re mediocre, you’re done. They’re just going to replace you with a robot.

You just see more efficiency in rules-based systems, and that’s going to eliminate white-collar jobs. If you want to compete: you need to know how to use it to enhance yourself, and two: you need to have skills that are not automatable. If you’re a plumber, it’s hard to make a robot do plumbing. Or carpentry.

That’s the way I think about it, and a lot of people in Silicon Valley are just looking at it as the efficiency. I can scale faster, but I think it’s slowly going to turn into “I don’t need as many people.”

Unleashing Creative Potential with AI in Entrepreneurship

Discussing the untapped potential of AI in creative and entrepreneurial endeavors, Jarie envisions a future where AI tools like ChatGPT play a pivotal role in customer discovery and product development. By generating synthetic data and role-playing customer personas, AI can significantly reduce the time and resources spent on market research. This approach not only accelerates the innovation process but also provides a more objective assessment of ideas, paving the way for more rapid iteration and validation of business concepts.

J.: It sounds like the focus right now is on systems and efficiency, which is natural. When new tech comes out, we don’t know what to do with it. That’s the first lever we use—let’s make things quicker and easier.

I have a theory I want to run by you, and I think this could make me a lot of money, or you a lot of money, or anyone a lot of money if they can pull this off. I have this theory that the real value of something like the chatbots is not in the systems processing or in the sales, but it’s in the creative entrepreneurship realm. It’s in the customer discovery and development phase.

For example, if you could go to a small to midsize startup, and you could teach them how to use a chatbot to replicate customer interviews, that could save you a tremendous amount of time and energy on development because instead of going out and interviewing a hundred people, you can have ChatGPT roleplay your archetype, and you can get eighty-five, ninety percent of what you need out of that in a fraction of the time. But I don’t see anyone there yet. I don’t see anyone pushing into that creative space. What do you think about that? Am I way off?

Jarie: No, I don’t think you’re way off. I think you’re just way ahead of the curve. One of the things when I build these corpuses for these SOWs, these processes that I try to automate as much as I can, I use synthetic data. I tell the bot, “I want you to answer these questions like you are this type of persona.”

There are people today who do synthetic data for testing software. It used to be when you were testing software, you would just take your database, you clone it, and then you put it in your development environment and test against it. The problem is that you’re copying sensitive customer data, and so that’s a big GDPR problem. That’s a huge, massive problem—privacy. There are companies that will build you synthetic databases. It will make people up and then you can test your data on it. You can make corner cases that you would normally not make. From a testing point of view, synthetic data is really powerful, and it’s mostly for hardcore developers, for entrepreneurs, for what you mentioned–creative entrepreneurs that are trying to figure out products or get market feedback.

It’s the same problem that writers have. No one wants to read our drafts. We don’t have a good source of objective critical feedback for what we do early on. You’re gonna be in a writer’s group, but are they really gonna tell you the truth? Maybe. I don’t know. That’s hard to find. So to your point about testing potential customers and messaging, think about it as a writer assistant that you say, “Here are the rules. I want you to analyze this piece. Tell me what I can do to make it better.” And it’s objective. It loves you more than your buddies.

I think you’re on to something. I mean, it’s things that are rules-based, that you can do research on, it excels at. Synthetic data is a really good application because it can generate things you’d never think of.

I’ve done this before. I was testing a corpus that I was writing, a pretty massive one. We were doing some analysis of messaging and positioning for companies, which basically means, “What am I telling the market?” You use both internal and external feedback, and ideally, you just interview a bunch of their customers and get the input, but we didn’t have any customer input because it’s hard to get customers to talk to you. So, I said, “Generate ten customer interviews that would use this product with these personas.” I don’t even think I said personas. “Answer these questions. Use that information to do the rest of this.” Genius. I literally told it, “Assume you are an expert in whatever,”and it just did it. Then, I could work on it. I think synthetic data is a big use case, and I think it’s realistic synthetic data for what you just talked about. It’s so valuable. Why not accelerate your time to get up to speed?

J.: Even in a mentorship model, if you’re a founder or you’re part of a small startup team, and let’s say you have VC backing or you’re in an incubator, and you have a mentor who’s seen a hundred or 150 startups—amazing for a human, but ChatGPT has a dataset that’s a thousand times that. If you’re using ChatGPT for product market fit, it just has a much broader data set.

I’m not saying it’s better than a live mentor, but again, even when you interview a customer, they’re not telling you the truth. You’re building a gym, and you’re say, “Hey, if I built this gym across the street from your house, would you work out five days a week?” And they’ll say, “Oh, I totally would.” You know it’s bullshit. Asking someone what they would do is pointless.

Jarie: I totally agree. I think you nailed it. There is a huge opportunity for that, and it’s because you need to iterate fast and especially in this day and age. You fall in love with the problem you’re trying to solve and then iterate until someone buys your solution. It’s unfortunate, but that’s the way life works. It’s not the “Mad Men” era anymore where you’re like, “We’re going to make a new soap!”

J.: When I started teaching entrepreneurship to high school kids ten years ago, it was Lean Startup, it was Eric Ries, it was Business Model Canvas—build your MVP. Now, you don’t even have time to build your MVP. What if you build ten MVPs and number eleven is the one that works? Well, you’ve wasted all that time building ten. So now I say, “Don’t even think about the solution yet. You gotta validate the problem.” AI can be a great way to accelerate that process.

Jarie: I’ll give you an example of a use case. I wanted to create a class for mastering story-driven B2B marketing. I have all this content. I’ve talked about storytelling and B2B marketing for a long time, and I’m trying to figure out what people want. To your point, I did exactly what you just described. I said, “Assume you’re a marketing expert. Let’s look at the landscape of marketing education, and tell me what people like, what they hate.” The AI went out and gathered the information for me. I have an intuitive sense of that because I’ve talked to entrepreneurs for years, but it was nice to validate my knowledge. Whether or not people buy the solution you build is a totally different thing, but at least now I can use AI to validate my intuition.

Forecasting AI’s Impact on Future Work and Creativity

Looking five years ahead, Jarie anticipates a landscape where AI seamlessly integrates into all facets of work, serving as a ubiquitous assistant that streamlines routine tasks and fosters strategic and creative thinking. He predicts that this AI-driven efficiency will challenge professionals to elevate their unique value propositions. Despite potential disruptions and discomfort, Jarie believes in the transformative power of AI to enhance the quality of work and life, enabling a focus on fulfilling creative pursuits and innovation.

J.: What does your life, business, writing—however you want to answer it—look like five years from now?

Jarie: Like any technology, when it gains traction, it accelerates pretty fast. It’s an “S” curve. I think we’re probably at peak hype or just entering the trough of sorrow.

I think in the next five years, there’s going to be solid use cases backed by data. It’s going to affect white-collar people the most. Your AI is going to be your junior assistant. There’s not going to be any part of your workflow that isn’t touched by AI. In fact, there’s probably not much that isn’t touched by AI now. It’s going to give you the ability to do rules-based grunt work quickly, efficiently, so that you can focus on the things it can’t do like strategy, creativity, and putting things together.

What will happen is the noise in the world is going to rise pretty significantly. You’re going to have a bunch of shit out there—thousands of web pages that AI built that are just crap. As a creative and as a white-collar worker, you’re going to have to raise your game, and you’re going to have to really solidify your value add. What can you do that the bot can’t do? That’s scary to people because, if you’re not in a growth mindset, you’ll feel like a typist about to lose their job to a computer—like in the 80s. You need to adapt and overcome. We’ve gone through these cycles forever. There has not been a time in human history where we haven’t been through a technological advancement where we all had to learn and retrain.

I think it’s going to be your assistant. It’s going to be everywhere. They’re going to figure out the privacy, they’re going to figure out the security. There’s going to be those hiccups. It is going to enhance your day-to-day working, and if you use it right, you will be able to spend more time thinking and creating original things.

My fear is that the efficiencies are not going to be passed down to the worker. Although, if you’re really good at it, like anything, you’ll get paid more.

I also think if you’re a solopreneur or a creative, and you choose to, I think you can work less. I mean, we’re both Gen X, so people can figure out how old we are, but I am looking forward to a time where I spend more time doing creative things I enjoy that are more “fulfilling,” and less time trying to make a living.

There’s going to be a lot of thrashing, and there’s going to be a lot of people who are going to be upset just like when the printing press happened, just like when the computers became big, just like the internet, just like all these other technologies that disrupted our lives. It’s tough, and you’re going to be uncomfortable, and people are going to lose their jobs, and you got to figure that shit out. It doesn’t mean you got to go learn how to code. It’s just history. This is the way it’s been for thousands of years.

✔️ Insights & Actionable Advice

Early Exploration and Adaptation to AI Technology:

Insight: Embrace early experimentation with AI to discover its potential applications in your field, much like Jarie's initial forays into using machine learning for logistical challenges. This early adoption can uncover innovative ways AI can support creative processes and business strategies.

Actionable Advice: Begin by integrating AI tools into small, manageable aspects of your projects to understand their capabilities and limitations. Use these insights to innovate in your creative work, whether it's through automating mundane tasks or enhancing your content's analysis and synthesis.

Generational Advantage in AI Integration:

Insight: Leverage the unique blend of technological savvy and life experience that Gen X and other experienced generations possess. This combination allows for a deeper understanding of quality and the strategic use of AI tools to enhance creative work.

Actionable Advice: Use your experience to critically evaluate AI-generated outputs and guide younger professionals in discerning quality work. This can be particularly valuable in roles that require a strong sense of brand voice or creative integrity, ensuring AI tools enhance rather than dilute the quality of output.

AI as a Tool for Enhancing Efficiency and Creativity:

Insight: AI's real leverage lies in its ability to process and analyze data at volume and speed, freeing up time for deep creative thought and strategy development, as Jarie experienced with ChatGPT's data synthesis capabilities.

Actionable Advice: Implement AI tools to handle data-heavy tasks such as market research, competitive analysis, and content synthesis. This will allow you more time to focus on creative strategy, concept development, and personalizing content to your audience's needs.

The Role of Synthetic Data in Creative Testing and Development:

Insight: The use of synthetic data and role-playing customer personas with AI can drastically reduce the time and resources needed for market research, as highlighted by Jarie's approach to testing business concepts and messaging.

Actionable Advice: Create synthetic datasets or use AI to simulate customer interactions and feedback on your creative projects. This approach can help refine marketing strategies, target audience analysis, and product development before investing in large-scale production or campaigns.

Continuous Learning and Adaptation in the AI Era:

Insight: The necessity of lifelong learning and adaptation is underscored by the rapid evolution of AI technology and its impact on creative professions. Jarie emphasizes the importance of staying curious and open to new tools and methodologies.

Actionable Advice: Dedicate time to learning about new AI technologies and their applications in your field. Participate in workshops, online courses, and professional networks focused on AI in creative industries. Experiment with new tools and share your learnings and creations with your community to foster a culture of innovation and adaptation.

🗺️ FREE! // Content Marketing with ChatGPT

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📣 J. Thorn Public Appearances

If you’re interested in hearing me speak, present, or pontificate on a panel, check out my speaking schedule.

Note: ”Upcoming” gigs are linked to the event site, while “Past” gigs are linked to replays, where available.


✅ Idaho Writers Conference ('24) April 11-13, 2024 - Boise, Idaho

✅ University of Delaware - The Diamond Challenge ('24) April 26-27, 2024 - Newark, Delaware

✅ Creator Economy Expo ('24) May 5-7, 2024 - Cleveland, Ohio

✅ Author Nation Live ('24) November 11-15, 2024 - Las Vegas, Nevada


✅ South by Southwest ('24), March 8-16, 2024 - Austin, Texas

✅ Author Alchemy Summit ('24) February 22-25, 2024 - Portland, Oregon

✅ Creator Economy Expo ('23), Cleveland, Ohio

✅ NFT-NYC ('23), New York, New York

✅ StokerCon (‘23) Pittsburgh, Pennsylvania

✅ Cincinnati AI for Humans (October 2023) Cincinnati, Ohio

✅ Fiction Marketing Academy Summit (October 2023) Online

✅ 20Books Vegas ('23) Las Vegas, Nevada

📰 Stay Up-To-Date on AI News

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