3 Marketing Mistakes I’ve Made
Part of the appeal of Sharp Pen (and part of how I got the business off the ground in a crowded category of adtech PR agencies) is that I eat my own dog food.
Our shtick is executive evangelism: putting the founder or CEO out on first-party channels. We tell clients to build audiences through social, email, and audio rather than relying entirely on third-party gatekeepers. And I do that myself. That’s why the pitch works.
But it also means I’ve made a lot of mistakes marketing myself and my business. Those mistakes ultimately made me a better marketer, both on my own behalf and on behalf of clients.
Here are three past errors that guide me today.
1. Betting it all on one big asset
In 2023, I got it in my head that I was going to write the white paper to end all white papers.
This was very academic thinking. I’d done a PhD in literature, and I seemed to believe that if I wrote a startling manifesto, everyone would suddenly see the error of their traditional PR ways and embrace my company. Moreover, they’d spend way more money on communications Joe Zappa–style because they’d be able to grasp its transformative potential through the beauty of my prose.
Well, folks, probably seven people read the white paper, and as may come as no surprise, it did not have a transformational impact on the business.
The mistake was not necessarily the writing or the ideas. Rather it was investing an enormous amount of time, money, and energy into a single asset at a time when I had very little attention.
The vast majority of academic books (even good ones) have almost no lasting impact on the author or the field. The same is true of marketing assets. One polished, beautiful piece of content is very unlikely to change your life.
The answer in modern marketing, especially in a world where information volume is extremely high and attention spans are low, is not to bet everything on one giant splash, but to create lots of very good content consistently.
Over time, people begin associating you with a big idea. That’s how marketing actually works. Instead of one massive moment, it’s 200 little moments over the course of a year.
2. Going after the wrong audience
Early in Sharp Pen’s existence (the agency was founded five years ago), I wrote a lot about B2B marketing best practices. But I also wrote about being a freelance content writer because, at the time, that’s essentially what I was before building an agency.
This attracted a strong audience on LinkedIn because there are tons of freelancers all over the world who love to post and support each other. And honestly, it was a lovely group of people.
If you looked at my LinkedIn engagement history, you’d see this period delivered some of the best numbers of my career. At a time when my business was maybe 25% the size it is now and I was essentially a glorified freelancer, every post got at least 50 likes. Not bad for the tiny universe of B2B marketing.
Amazing, right? Wrong.
That audience was never going to buy from me. It was not aligned with my commercial or entrepreneurial aspirations. I was effectively pandering to a crowd with no economic value to my business.
The CEO equivalent of this is posting constantly about entertainment, politics, or HR. Now, you can absolutely do some of that. But if that’s all you’re doing, you’re probably not reaching the right people.
Posting about what your customers are actually interested in (some niche pocket of adtech, for example) will often produce less engagement. But if it’s the right engagement, that’s where you should go, even if the post only gets 12 likes.
If your average deal size is six or seven figures, 12 likes from the right people can be incredibly valuable. Two hundred likes from random people are worthless.
3. Betting on an unprovable idea
I tried a lot of differentiators for Sharp Pen in its early days.
“We’re smarter”
“We’re PhDs”
“We’re more strategic”
All potentially true — you’d have to ask the clients. But none of those ideas could really be proved. None were tangible or traits competitors couldn’t also claim. Also, none were particularly timely or instinctively compelling. And most importantly, none started with a critique of the industry itself.
Compare that to our positioning today: Traditional PR is dead. Throw out the 2005 marketing playbook. The era of executive evangelism has commenced.
That is a salient argument, and the growth of the business proves it.
The message is timely because it touches on where media and marketing are heading. It’s also customer-centric because it’s fundamentally about helping companies adapt to the shift from earned-media gatekeepers to first-party distribution. And lastly, it begins with a critique of the status quo.
Plus, I’m visibly practicing the playbook myself. You can see the social posts, the newsletter, the podcast, and the audience building. All of that makes the positioning stronger than what I tried before. More tangible, timely, and intuitive when buyers simply care about their own problems.
And when you combine that philosophical differentiation with a niche (i.e., adtech), you get a genuinely strong position: an adtech PR agency built around executive evangelism rather than traditional PR.
Whaddaya know? The agency really took off once we embraced that message.
3 marketing best practices
The throughline in all these mistakes is simple. Modern marketing is not about giant campaigns, vanity engagement, or abstract claims about being “better.”
It’s about consistency, audience alignment, and tangible differentiation.
Create lots of good content instead of obsessing over one masterpiece, reach the right people instead of the biggest crowd, and build your positioning around an idea that is timely, believable, and easy for the market to understand.
That’s what I learned the hard way.
