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Behind one of my most rebellious blog posts

Yo! Welcome to the next episode of The Reeder, where you get expert content strategy advice for growing your career and business every Saturday morning.

If you’re new, you can subscribe here and join the crew.

The Reeder is sponsored by Content That Converts

A lot of people are playing in the attention economy, but not enough people are winning dominating.

I didn’t have a playbook or mentor to “show me the way.” I was self-taught and had to just experiment over and over and over until I finally figured it out.

This year I combined years of experience into one guide to help you grow your career and business faster. It’s called, Content That Converts, and it reveals the exact strategies and tactics I used to:

- Create Gong’s content strategy and brand
- Drastically increase my earning potential
- Build my combined audience to over 87k
- Scale The Reeder to a 6-figure side hustle
- Lead content and thought leadership at Clari
- Book hundreds of podcasts and event speaking opps

Now they’re yours.

If you’ve been telling yourself to finally start creating content — or drastically improve your results if you’ve already committed — I can say with complete conviction that this ebook will help you.

Let me tell you about one of my favorite — and possibly most rebellious — things I ever published at Gong.

But first, the backstory:

Sometime in 2020 my boss came to me with an ask. This isn’t entirely unusual given he’s my manager and all. And this particular boss of mine was not immune to asking me for a lot of things, and often, as is his right. Suffice to say, I wasn’t surprised when he transitioned our conversation with a “Hey, quick ask for you” midway through our virtual one-on-one.

“So I was talking to Doug…”

Oof. I already didn’t like where this was heading.

Doug (not his real name) led the commercial sales team. He’s a short, stout, frowny guy, intentionally and proudly emotionless, and the type to rebuttal with “covid isn’t real!” to any poor seller whose forecasted deal ran into a budget freeze at the finish line (which he has in fact said, I’ve been told, on at least one occasion).

And it’s important to know that at this time, Gong was in real hyper-growth. 

At this time, the company was catching serious momentum and pressure to perform was mounting daily. Yet Doug’s team was consistently the top-performing and most reliable. I remember multiple quarters his commercial team even closed more business than the enterprise team. They were that good. To get in the way of that humming engine was to ask for a target on your back.

All’s to say I knew whatever task was about to land on my lap carried the weight of Doug’s clout and his willingness to use it to get any naysayers to submit to his will.

My boss continued, “And he asked me what we can do to help his team out. You know, using content or something…” 

He trailed off, seemingly hoping that I already had the answer to finish his thought. 


Then I replied, “Does he have anything specific in mind?” — knowing damn well he didn’t. 

Thinking back, I suppose I was hoping Doug wanted a certain type of lead or deliverable. For example, sellers usually love field event leads because they “actually have a chance in hell of closing this f—ing year.” 

I would have been happy with any direction, really, just to avoid the guessing game of figuring out what a sales leader, who doesn’t understand marketing, care to understand marketing, or frankly give a sh*t about marketing (unless it makes his job easier), really wanted. 

Then, I got my answer:

“Something that makes people want to buy right now.”

A smirk crept across the left side of my then boss’ face as those final words exited his mouth. 

He knew it, clear as day. It was a vague, thoughtless, and dare I say, bullsh*t, request. And my boss knew it didn’t make any sense. But this didn’t bother him, because the smirk also revealed this was now my problem to solve.


Even though his unsaid message was well received, I couldn’t resist flaring my smartassness a bit before inevitably falling into line:

“If it were as simple as telling people that they should buy from us, then we’d be selling A LOT more software. Hell, my job would be so easy I could log off at noon every day. I’d love that. But that’s not exactly how marketing works.”

His expression didn’t change.

I sighed. “I’d probably have more luck telling people why they shouldnt buy from us” I half-joked. He pretended to laugh, clearly uninterested and already thinking about the next topic on the agenda. 

Here’s what I ended up doing 

It would be easy to blame my rebellious nature, but the truth is, what followed was really based on my guiding philosophy on content marketing:

My goal is to earn attention and convert it into action

That requires breaking patterns — aka “the norm.” Adding a dash of controversy helps too.

So I decided to do the opposite of what was asked of me. 

I began writing a blog titled, 5 Reasons You Should Not Buy Gong.

A little well-timed reverse psychology. Who wouldn’t click?

Ok, what to actually say… I figured if a sales rep had a shot to motivate a sale in a live conversation, they’d love to tell prospects all the reasons they should buy.

So I decide on a listicle. I like prime numbers for listicles, so let’s say 5. That’ll do.

If you skim the article, you’ll notice what I did. I wrote out our top 5 value props, then flipped them:

You get the idea.

Why did I take this route? 

I want the reader to have a moment of self-realization, nodding their head and realizing I don’t have any of those things! And I want them! What can I do?

A tad exaggerated to make my point, but not much.

I know buyers expect to be told all the reasons they should buy.

So I flipped it. I qualified them out. Maybe you don’t need Gong. That’s unusual, and therefore, intriguing.

You’ll also notice my tone isn’t overly excited, welcoming, nor desperate. That’s key. I had to commit to the reverse sale with a hint of “take it or leave, I’m good either way.”

Risky, perhaps. But sure beats desperately begging for their business.

Final anecdote 

A few weeks after publishing the blog, my boss shared this:

He decided to target contacts in late-stage, in-flight deals with paid ads leading to the blog. 

His beloved attribution model showed that it was becoming a frequent last-touch interaction before said prospect signed a deal with us.

In other words, it worked.

Now I could say my brilliant blog was THE reason these deals were closing. And while that might feel good and feed my ego, the truth is this:

  1. It most likely nudged people who were already going to buy to sign - just maybe a little faster

  2. At best, occasionally it pushed indecisive buyer’s off the fence and into a contract with us

Honestly, it’s probably both.

I’m happy either way. Blog traffic and conversions were healthy. I did my job.

Doug was happy he got his “why you should buy now” marketing asset, and the attribution model showed a whole lotta of pipeline influenced from this marketing touch point.

And it must still be working decently — it is still on their website after all. 

What this means for you

  1. Be intentional with your desired outcomes before creating content

  2. Take bets and do the unexpected to earn attention

  3. Focus on where and how your reader will have a “moment of self realization to do the “selling” for you

This will help you create highly-engaging content and keep the Doug’s happy and off your back.

Holler at you next week with a special “stocking stuffer” edition,

PS: If you liked today’s post, you can help me grow by sharing this link with one person.

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