The One Question Post That Boosts Engagement Fast

Actionable and centered on the Weekly Challenge—clear, practical value.

Author

Javier García
August 25, 2025 • Estimated Reading Time: 6 minutes

In partnership with

Introduction

Welcome to another exciting week!

Table of Contents

Sponsored Section

Unmanaged AI = Unmanaged Risk. Shadow IT Could Be Spreading in Your Org

You wouldn’t allow unmanaged devices on your network, so why allow unmanaged AI into your meetings?

Shadow IT is becoming one of the biggest blind spots in cybersecurity.

Employees are adopting AI notetakers without oversight, creating ungoverned data trails that can include confidential conversations and sensitive IP.

Don't wait until it's too late.

This Shadow IT prevention guide from Fellow.ai gives Security and IT leaders a playbook to prevent shadow AI, reduce data exposure, and enforce safe AI adoption, without slowing down innovation.

It includes a checklist, policy templates, and internal comms examples you can use today.

Best Ad of the Week

American Eagle – “Sydney Sweeney Has Great Jeans”

American Eagle’s latest ad featuring Sydney Sweeney surprised everyone. The play on words—“jeans” vs. “genes”—quickly sparked controversy over implications tied to racial stereotypes and eugenics. The backlash ignited critical discussions about beauty standards, representation, and marketing ethics. Still, the campaign generated staggering visibility—billions of impressions, significant stock gains, and comparisons to “meme stock” dynamics. This polarizing mix of attention and risk raises vital questions about the true value of shock advertising.

Key Marketing Lessons

  • Attention ≠ Approval
    Even when campaigns go viral, brands must weigh whether the attention aligns with values and long-term brand loyalty. Shock value may grab eyeballs, but it can also alienate core audiences.

  • Controversy is a double-edged sword
    The ad delivered massive exposure—including a stock uptick and pop-culture discourse—but also raised concerns about tone-deafness and insensitivity. Winning in the short term doesn't guarantee lasting goodwill.

  • Context and nuance matter
    In a time of heightened awareness around representation and cultural messaging, everything is amplified. Ads must be informed by diverse perspectives before launch to avoid misinterpretation.

  • Crisis readiness is essential
    Backlash is often swift and unforgiving. Brands should have agile communication strategies in place, even if they're pursuing edgy or culturally disruptive campaigns.

    American Eagle – “Sydney Sweeney Has Great Jeans”

Sponsored Section

Learn from this investor’s $100m mistake

In 2010, a Grammy-winning artist passed on investing $200K in an emerging real estate disruptor. That stake could be worth $100+ million today.

One year later, another real estate disruptor, Zillow, went public. This time, everyday investors had regrets, missing pre-IPO gains.

Now, a new real estate innovator, Pacaso – founded by a former Zillow exec – is disrupting a $1.3T market. And unlike the others, you can invest in Pacaso as a private company.

Pacaso’s co-ownership model has generated $1B+ in luxury home sales and service fees, earned $110M+ in gross profits to date, and received backing from the same VCs behind Uber, Venmo, and eBay. They even reserved the Nasdaq ticker PCSO.

Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.

Weekly Tip

Embrace White Space

Crowded layouts overwhelm readers. White space guides attention and makes your message easier to digest.

• Break text into short paragraphs
• Leave breathing room around images and CTAs
• Avoid cramming too many elements into one frame

A cleaner design feels more professional and keeps the focus where it matters most—on your message.

Weekly Challenge

Engagement Question Post

Create one dedicated post designed only to spark conversation:

• Write a caption that asks your audience for their opinion, experience, or preference
• Keep the question open but specific (e.g. “What’s the one tool you couldn’t run your business without?”)
• Respond to every answer to keep the thread alive
• Track how many new comments and profile visits come from it

Conversation-driven posts often outperform purely informational ones.

Submissions + Feedback

Hope you enjoyed today’s post, if you know someone who may be interested, feel free to send it to them.

Also, if you want me to cover any specific subject on the next issue or share some feedback, feel free to reply to this email.

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