A marketer's guide to AI without the BS

How to make sure your content never has the “AI smell” and you’re getting maximum leverage from LLMs in your marketing

The following is a conversation with Jesse Boland, 17-year Silicon Valley startup marketer (ex-GoFundMe, ex-Ironclad, now Hiline), former firefighter (who broke his back on a fire which caused him to hang up the uniform and become a marketer).

How is GTM strategy changing with AI?

The proliferation of terrible content is staggering (now it’s just AI generated rather than offshored). The amount of people telling you how to do stuff with no actual boots on the ground experience is wild. The barrier to entry in any market is really as low as it ever has been. The low end of the content game is like a pie eating contest where the prize is more pie.

Back in the day you could just create a BS piece of content that you’d lightly researched (i.e. mostly stream of consciousness) and compiled from stuff you’d found on the web, and just be slightly better than the rest and expect to rank. Throw some ad budget on top of that, you’re good to go. Do that at scale and you’d have had a pipeline juggernaut. 

Shit was a lot easier, and if you had talented hard working folks around you, you’d crush.

But…not anymore! The environment is scarcer and more competitive across the board.

And yet, it still works to use (great) content to go to market.

AI is like Mario’s super star power-up, now the bottleneck is really your ability to influence your organization and tangential folks around your business, to extract the information you need from SMEs in the business, to sit down on calls with clients, to listen and extract understanding from client calls and compile that data into workable, flexible repos that you can then mine for gold.

Tell me more about SEO specifically.

There are aspects of my profession—like SEO—that are definitely changing. I wouldn’t say it’s being decimated, but there’s a lot of fear, uncertainty, and doubt. SEO has been a key focus for every business I’ve been in, but it may not exist the way it has for the last 20 years.

Google is potentially becoming its own AI-driven search engine, sourcing all the information we give it, and giving us little credit. They’re trying to roll back some changes to give more recognition to small, independent publishers, which was the original appeal of Google 20 years ago. Back then, even if you weren’t a talented writer, you could still eke out a living online by writing about niche topics. 

You could dominate certain industries as a self-publisher and do very well. That’s what drew me to the internet—I’ve always loved writing and communicating, and Google gave me a way to make a career out of it. 

But things are changing, and who knows what it’ll look like in 3 years? It certainly won’t be like it was 10 years ago. I’m just trying to stay ahead, keep up with new developments, and make sure I’m in control rather than letting younger, smarter people outmaneuver me.

What about your own personal process?

My approach has always been more intent-based than keyword-based. Keywords help understand intent, and I don’t think that’s going to change. Google’s algorithms are still focused on delivering what people want as quickly and accurately as possible. That hasn’t changed, so we need to stay ahead of the curve and deliver what people want.

While AI is delivering a lot of that information, this is still a people-to-people business. Despite the machines translating and delivering content quickly, there’s still a human element involved.

Do you think there’s a threshold for how much AI content people will tolerate?

I certainly hope so. I think it’s still fairly easy to spot AI-generated content. There’s been a lot of bad content promoted by Google in the past, content that was outsourced and barely readable. 

AI has actually improved some of that by using logic to put ideas together coherently, passing through the filters we all have. But yeah, I’m hoping AI-created video doesn’t become a thing because I still value the unique creative ideas that people have.

What AI models do you use?

I use both ChatGPT and increasingly more Claude. I like Claude’s project model because it keeps things organized. I can use it to train what I call “small language models” individually. Claude’s model is great—you can train it on someone’s voice or a specific structure for a page. 

I use it, test it, edit it, feed it back to Claude, and it usually comes up with a better version. It’s an iterative process, but everything still goes through the human filter before it gets published. I add my own experience and perspective. 

I’m not just relying on the machine to tell everyone what to think. It helps me test and expand ideas or refine them when needed, but I’m still the one doing the thinking.

For the future of AI, are you bullish, skeptical, or somewhere in the middle?

I don’t fully know where I stand right now. When I use it, I’m blown away by the advancements over the last five years. It’s changed the way we all work in ways we might not even fully realize. But I’m also scared of a future where everything is AI-driven because I still really value human thought.

So, I guess I’m somewhere in the middle. I’m a bit agnostic about where it’s all heading. AI makes me better at what I do, but at what point do I become redundant as the operator?

That reminds me of something I’ve been thinking about—AI-generated content that’s obviously AI. It’s almost like it “smells” bad. People can tell, and they just mentally note that it’s AI content. Do you think that kind of thing erodes credibility, especially in marketing where brand and reputation are key?

I think it does, especially if we start relying too much on algorithms to communicate our ideas. It can turn into a race to the bottom where you have derivative content passing for something credible. If non-experts start talking about expert topics, we all get lost. 

That’s why we need to lean into our expertise and experience as humans. AI can help, but it’s still our job to add creativity and personal insight to what we produce.

It’s clear you have a distinct style and voice—there’s a certain pithiness to it, for lack of a better word. It’s uniquely yours. But some people don’t have that natural inclination toward writing or communication. What happens to them in an AI-driven world?

That’s a great question. I think with AI, it’s a lot of “garbage in, garbage out.” My natural way of communicating doesn’t always translate well with AI. I often find myself disagreeing with how it tries to mimic my voice, and I end up heavily refining it to align with the way I want to tell the story.

To your point though, I think AI will eventually get better at picking up on the nuances of how we communicate. It may start incorporating those subtleties into its output. I hope I’ll always have a unique style, but who knows where this is all headed? It’s both exciting and scary.

The more I use AI, the more I find myself avoiding it for the things I’m truly passionate about. For example, with this newsletter, I don’t use AI at all to write it. When I’m passionate, it’s easy to write 2,000 words in my own voice without even realizing it. I wouldn’t want AI to touch that. But then, I’ll paste the whole article into Claude and ask it to generate 15 headline variations focused on a specific angle, and it nails it. Knowing when to bring AI in is a huge unlock, and knowing when not to is just as important. A lot of people are struggling with that right now.

I agree. If you bring AI in too early, before you’ve fleshed out your ideas, it can derail the whole project. I’ve had to scrap entire projects and start over because of that. I’ve found success using AI to adapt content for others, like founders or executives. I’ll write something from my perspective, then train the AI on video clips or transcripts of the person talking. That way, it mirrors their voice more accurately. But yeah, if you pull it in too early, you can end up cutting your own legs out from under you.

I’ve been in that scenario a couple of times in the last year and a half—getting so excited about using the tools that I realize, “This isn’t it.” Then, I end up starting over, completely redoing everything from scratch.

Yeah, you just nuke the entire ChatGPT history and start fresh.

I’d love to hear your thoughts on the good, bad, and ugly of AI in your organization. What’s your long-term plan with AI?

Well, being in venture over the last 10 years, I’ve seen boom and bust cycles, culminating in early 2022 with what I refer to as “SaaS-ageddon.” That boom cycle led to an overload of tech and unrealistic valuations, and now for many resources are tighter. 

We’ll need to stay ahead of AI and use it to punch above our weight since we can’t rely on the resources we had before. Internally, we refer to AI as “the assistant” or “the robot,” and it provides low-cost help. ChatGPT Premium is only $20 a month, and with several tools for less than $100 a month, we get an incredible ROI. Over the next few years, I expect to keep using it and encourage my team to do the same.

AI lets you hold more ideas in your head at once because you can delegate some of that thinking to the models. You can input your notes, random thoughts, and let the model parse them and put them in the right place. It’s exciting and scary at the same time. 

We’ll see where it goes in the next few years. For example, in the accounting space, AI is going to revolutionize bookkeeping and accounting in the next five years. Our company needs to stay ahead of that curve and use the technology as a massive tool. If you’re not staying on the bleeding edge, you will fall behind.

What’s your biggest win to date?

Biggest win. Personally, finding a balance between job satisfaction and life. I have a 15 month old daughter, and I’m also in my 40s. I’m unwilling to deal with drama at work, I don’t work with assholes, that’s my hard line that I’ve come to later in life.

Professionally, there was always the $37 million dollar Hurricane Harvey Relief fundraiser that JJ Watt started because YouCaring.com outranked GoFundMe for the keyword “free online fundraising.” Or crushing our pipeline targets 9 quarters in a row at Ironclad. All these things were fun and good feathers in my cap. 

What are your goals for the next quarter? Next year?

Blow my targets out of the water at Hiline. Build it into an iconic business. Launch a killer new brand here, which will be the 3rd one I’ve launched in the last 2 years.

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