There's no other way to put it... in the last month I executed the two silliest marketing projects of my career. They both were for no particular reason; I can't tell you that either was particularly strategic.

But here we are.

It all got me thinking a lot about the importance of having fun at work—and fun with your marketing.

Let's take 'em one-by-one.

Imagine Outseta

The video below is just completely silly—I made it for no particular reason other than I thought it was fun. I wrote the lyrics to the song on a whim, then hired a vocalist ($80) and video editor ($80) to apply some polish.

Looking back now, all I can really say about this project is that for $160 I got a very evergreen asset that presents Outseta's brand in a fun way. I can't say that this will do much for us, other than communicate to potential customers that we don't take ourselves to seriously and inject some life into our brand.

Hubspot, Stripe Engaged in Secret Arms Race with Mysterious Start-up

This project is much more interesting to analyze—I published a post on Outseta's blog entitled Hubspot, Stripe Engaged in Secret Arms Race with Mysterious Start-up. I shared this post on Twitter and it very clearly struck a chord with a lot of people—and especially other marketers.

I've never had a single post result in more highly credible people follow me (including the CEO of a billion dollar company!) and I've rarely gotten the type of praise you see below from other people whose opinions I respect a lot.

I'm the first to tell you that seeing my work acknowledged this way feels good; but it's also interesting because I've put so much more effort and experience into other more educational and earnest posts that haven't gotten a fraction of the reaction.

Why?

As a bit of backstory, both Hubspot and Stripe made major feature announcements in the same week—both to a huge amount of fanfare. And the truth is a lot of what they released is stuff Outseta has offered for a long time. Now I definitely understand that when you're a company of the size of Hubspot or Stripe, releasing any new feature is a much bigger undertaking than it is at Outseta. But I still saw an opportunity; I just wanted to poke a bit of fun at these industry giants, while also drawing attention to Outseta is a fun way. And there's a certainly a bit of self-deprecation here, too.

The idea for this post actually came to me in the middle of the night—I couldn't get it out of my head. By the time I woke up I had decided it was too risky, then I completely talked myself into it over the course of breakfast. I cleared my schedule and wrote and then posted this in about two hours.

Of those two hours, about 90 minutes was spent editing the post for word choice. I wanted this to read like a mock press release and I definitely wanted to poke some fun, but I wanted it to be crystal clear to the reader that this was meant to be lighthearted and nothing but silliness.

I think I got the tone mostly right by the reactions (there were a few haters in the comments, but I suspect they didn't read most of the post) and the post is packed with inside jokes that only people within the tech industry would get—I think that helped it land, too.

One thing that's kind of interesting is I'm fairly certain this post made its way to the folks at Hubspot, but being a publicly traded company they can't really share or comment on an article that describes their company as being in turmoil.

Nonetheless, I think the reaction here shows that people have an appetite for marketing to be more fun and entertaining. Additionally, people seemed to applaud that I took something of a creative risk.

It's hard to measure the impact of such projects, but I certainly view them as an investment in our brand. I generally think we all take work a bit too seriously, and I want Outseta's brand to be known as fun. Beyond that, the number of likes is about as "viral" as I ever get with the small audience that I have—bit the number of bookmarks is even more telling.

When someone bookmarks a post, it's a great indication that you really struck a chord and it's a post they want to return to—it's also a good indication that this post will get a high number of backlinks that will help Outseta with SEO. This ratio of bookmarks to likes is not something I see too often.

Having executed on both of these, I feel ready prioritize more fun in our marketing and more apt to fully step into taking creative risks—and I think that's worth a lot. It's also not lost on my that I have the freedom to do such thinks without oversight being the founder of Outseta.

I think there's a real learning here for people managing others, too. It's your job as a leader to give your team the space to take creative liberties; there's a lot to be said for empowering your team to take risks and step as fully as possible into their abilities as possible without the shackles of what might be perceived as "appropriate."

More fun, please.