He / she swooped in midmorning.

There was a pink blur and then a splash.

And then, I realized a Roseate Spoonbill had landed 15 feet from our deck (we were at the fishing camp) and I LOST MY MIND.

But quietly, because, duh, pretty bird nearby.

I took photos and videos and just enjoyed the mess out of the 3 or so minutes it graced us with its presence.

I’d never seen one in person.

Somehow I’d had a framed Audubon print of this specific bird and had moved it in and out of 5 houses without actually having seen one IRL.

The moment was special.

Even if he (she?)—I don’t know how to tell bird genders very well, it doesn’t stick— was hanging out near an old Dr. Pepper can that had been tossed in the lake so all my pictures read like “look how we’re ruining nature” PSAs.

I sent a few pics and videos to my mom, dad, and brothers. My dad is a bird watcher of sorts (is there a certification for that?) and he also LOST HIS MIND.

“Wow! Those are really rare. I’ve only seen one my entire life.”


Modern day family connection.

I could feel his joy (and jealousy) clear through the text.


One of my brothers, Rich, chimed in:

“They’re not rare. We see them all the time.”

Thanks, Rich.

Thanks for ruining the moment.

Thanks for being so committed to reality that you crushed our father’s excitement.

I’m not mad.

My dad isn’t either (are you Dad?).

But we’ve all been there, right?

Super excited about a thing for our own reasons—because we bring our own context to any given experience—and then someone says, “You’re silly to feel that way.”

How does this tie in to newslettering and content marketing?

Content can create amazing experiences, but it can also be a bubble burster.

You’ll want to be careful how you do both.

When you create experiences for your audience, they won’t be in a vacuum.

Share content you know they’ll love in this specific part of their journey.

“Saw this, thought of you.”

Help them make connections.

Earn their trust with truthful content.

When you’re bubble bursting, educate as you disappoint.

“XYZ is broken. Here’s how to fix it.”

It’s painful, but the message sticks.

And, after they mourn the thing they thought was amazing, they’ll remember it was you who helped them understand why it isn’t.

In either situation, craft your content with a strong goal in mind.


“Why would I create this moment?”

“What am I trying to teach?”


“How can I teach it in a way that respects the audience learning it?”

This is where you get to decide how arrogant your point of view should be.

My vote is to be and stay humble. I know sometimes experience leads to really strong opinions. It’s ultimately your choice how you deliver that opinion.

In other words, try to respect your target audience’s personal build up to the moment a very pink bird lands near them before you step in to teach them something.

Ashley Guttuso  

Newsletter Tips

Growth Strategy Round Up

These 3 newsletters are all actively growing and are sharing what’s working. Check out their stories and growth strategies here:

1. NOLA Business Insider

The NOLA Business Insider (3,200+ subscribers as of the end of July) is a daily email newsletter featuring the New Orleans business community’s challenges and opportunities. In this RJI article, Sydney Lewis reports on how they reached 1,000 subscribers on June 7…the same day they launched.

Their growth strategies included:

  • Audience research
  • Platform promotion
  • Paid marketing
  • Newsletter cross-promotion
  • Community connections
  • Analyzing effectiveness
  • And pivoting when they hit plateaus

Pay attention to their willingness to pivot:

“Our ability to pivot when we noticed the sign up numbers trailing off helped us get back on track towards our goal of reaching 10,000 sign ups within three months.”

2. Not Boring

In 2019, Packy McCormick started the Not Boring newsletter sharing business strategy, pop culture links, and commentary. He now has over 145K subscribers and is the #1 business newsletter on Substack. Arthur Takeda details his journey and growth strategies, including the way he:

  • Avoided a paywall by creating a sponsor deck and pushed it to potential sponsors
  • Shared failures, successes, and insights publicly and regularly
  • Created an investment memo and fund called “Not Boring Capital”
  • Launched a podcast
  • And other stuff, too

Key takeaway:

“His approach to writing is what I believe any content creator in any medium should work towards 1. Keep the audience’s trust; 2. Keep them engaged; 3. Put your best stuff out there”

3. Future Party

In this episode of Simon Owen’s podcast, The Business of Content, Simon interviews Boye Fajinmi, creator of The Future Party. It’s a witty business, entertainment, and pop-culture newsletter. Fajinmi started out hosting parties in 2012 and over the years turned that into a mega media company with 150K subscribers.

In the podcast, they discuss shifting from parties and events to becoming a media company; transitioning from a weekly newsletter to a daily newsletter; how they’re working to create, curate, and provide content for their niche; and the growth strategies they employ, including:

  • Leveraging events to bring in quality users (attendees become subscribers)
  • Organic growth within the entertainment industry
  • Creating a referral program
  • Remaining open to collaborations
  • And utilizing traditional, native advertising

I appreciated this truth bomb:

“Media is telling stories on different mediums… it doesn’t take a rocket science to see all the possible places we can tell stories on, but it does take a businessman to see that we can’t do all of those things at once. Right now we are focused on internal excellence.”



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Like this newsletter?

Let me know. Reply, email me at Ashley[at], or find me on LinkedIn to hit me with some feedback. I’d love to know what you think.

Happy content marketing (and newslettering),

Ashley Guttuso