Writing Attention-Grabbing Headlines

Most founders I meet are deeply attached to what they build. And they should be. That passion is what got them here. But here is what I have seen repeat itself across 37 years. Open any pitch deck. Read any website. Sit through any sales presentation. It is almost always inside-out thinking. "We are the best. We have the most features. We keep improving our product." And the sales are missing. Yet the founders keep adding more features, hoping that one more improvement will crack the market. I lived this myself while co-founding a startup. The market was not responding the way we expected. Our answer every time was to improve the product. Add a feature. Make it better. We were convinced we were building something great. And we were. But great was not enough. The turning point came when a large brand approached us, not because of our features, but because they had a real pain point that needed solving. We had the solution. That conversation opened up an entire market. The rest is history. They did not buy our product. They bought the relief from their pain. Your customer does not care about your features. They care about their problem. The moment your marketing stops talking about what you built and starts talking about what they can stop worrying about, everything changes. Three things you can do this week. Go to your website homepage and count how many times you used "we", "our", and "I." Then count how many times you spoke about your customer's pain. That ratio is your marketing report card. Rewrite one headline so it starts with their problem, not your product. And before your next post, ask yourself: Is this about me or is this about them? The brands that win are not the ones with the best product. They are the ones that make the customer feel most understood. #BrandStorytelling #FractionalCMO #MarketingStrategy #BrandBuilding #SmallBusinessMarketing #FounderMarketing #B2AI #FutureOfMarketing

A copywriting tip that's never failed me: 📝 Filter pain points through The Moment Lens.™ The majority of copy on pain points is vague: • "Fix your lack of qualified leads" • "Stop poor content performance" This word mishmash puts your prospect through mental gymnastics to visualize what this *actually* resembles in their life. And the second anything feels difficult...they peace out. Instead ask yourself: "What's the *moment* where this problem becomes unbearable?" • "Stop poor content performance" ➜ "No one reads the article you spent 13 hours on." • "Fix your lack of qualified leads" ➜ "Spending all morning prepping for a sales call only for a prospect to ghost. Again." The better you can describe your ICP's situation = more trust. (Not to mention this type of copy is waaayy more fun to write instead of robotic marketing jargon.)

The #1 website mistake advisors are making in 2025 (and how to fix it) ⤵ After coaching advisors for 30+ hours on the Advisor Marketing Made Simple podcast, I’ve spotted a common issue that’s easy to miss: 👉 If your homepage could be copied and pasted onto another advisor’s website, we have a problem. It’s vague. It’s forgettable. And it’s trying SO hard to sound professional, it forgot to sound human. Here’s how to fix it: ✍️ My 3-Part Formula For A Stellar Website Headline: 1️⃣ WHO you help Call them out by profession, identity, or life stage. IE. Teachers (profession), Asian Americans or LGBTQ+ individuals (identity), women going through divorce (life stage). 2️⃣ HOW you help What are the top 3 painful problems they are EAGER to pay you to solve? These are not the “nice to have’s”… these are the problems keeping them up at night. I like to call these your “profitable pain points.” 😉 3️⃣ WHAT do you want them to feel Infuse just enough personality to make your website headline FEEL different. Empathy, warmth, confidence — whatever fits your brand voice. (This is what separates you from firms with copy that could put you to sleep). 😴 Why all three? ➜ Clarity gets their ATTENTION. ➜ Problems make it PROFITABLE. ➜ Personality makes it YOURS. Now… here’s what that looks like when it all comes together: ✅ 👋🏻 Ideal Client: Asian American, pre-retiree. 🥴 Profitable Pain Points: They’re juggling multiple financial priorities—caring for aging parents while planning their own retirement, managing large RMDs from years of disciplined saving, and cultural expectations often mean they want to set up both their kids and extended family for success by passing down wealth. It’s a complex mix of competing needs, values, and responsibilities that deeply impact their financial planning. ↳ Headline & Subhead: As An Asian American You’ve Saved for Years—Now Let’s Make Sure It Lasts. We help Asian Americans balance retirement planning with caring for parents, minimize taxes on large savings, and create generational wealth. Let’s create a plan that honors your values and supports your family’s future. ——————— Anyone can write a headline… but this is how you write one that WORKS. Your website shouldn’t introduce you. It should rescue your ideal client from the problems they care about. 😉 PS. I’ve got lots more headlines I’ve written recently… let me know if you wanna see examples for: ⤷ The LGBTQ+ niche ⤷ Teachers ready to retire ⤷ High-net worth women navigating divorce

Why "Going Negative" Actually Works So you're scrolling through your feed. And ad after ad says "Get This!" "Get That!" "10x This!" "Finally, Do That!" It all starts to blur together... That's exactly why negative marketing can be your competitive edge. Let me explain. Negative marketing isn't about being a downer – it's about addressing real pain points your audience experiences daily. When done tastefully it's engaging, refreshing, and surprisingly effective. Why It Works: People convert when they feel understood, not when they understand. By acknowledging their frustrations, you're saying "We get it. We've been there too." This creates an instant connection that positive marketing simply can't match. Think about it, we are bombarded with strong headlines that promise way too much. Ex: "10X your results!" and "Transform your life!" Keeping it real about challenges cuts through the noise. Five Ways You Can Use Negative Messaging: 1. The Reality Check Headline: Start with a bold negative truth, then pivot to your solution. It grabs attention because it's unexpected. 2. The Common Enemy Strategy: Rally around shared frustrations – whether it's outdated industry practices, inferior solutions, or widespread misconceptions. (Remember: you're a marketer, not a politician) 3. Data-Driven Wake-Up Calls: Use surprising statistics to highlight industry problems. 4. The Honest Confession: Share your own past mistakes or limitations. Nothing builds trust faster than vulnerability. 5. The Problem Spotlight: Shine a light on issues your competitors ignore. When everyone else is playing it safe, honesty stands out. Pro Tips for Execution: - Never attack people personally (unless you enjoy lawsuits) - Always balance criticism with solutions - Use real customer comments and reviews for inspiration - Balance entertaining copy with real information - Stay genuine – people can smell fake authenticity from miles away Where to Find Your Angles: The goldmine of negative marketing ideas is hiding in plain sight. Read the comments on your ads, competitor reviews, and industry forums. Your audience is literally telling you their pain points – use them. And lastly, the goal isn't to spread negativity. It's about acknowledging real challenges and positioning your brand as the solution. When everyone else is saying "everything is awesome," being real becomes disruptive. The best part? Most brands are too scared to try this approach.

Too many headlines suck. Not because copywriters can't write – but because they forget the one question that matters. I reviewed 9 SaaS websites last week as part of a competitor audit. Almost all of them had completely interchangeable copy. You could literally copy-paste headlines from one website onto another without anyone noticing the difference. You know the kind of messaging I mean – because you've seen it too: 👉 "Streamline your restaurant management with our complete solution" 👉 "The all-in-one platform for restaurant operations" 👉 "The future of restaurant management is here" These could all be from the same website. Just change the logo. The problem isn't writing skill. It's that getting inside your buyer’s head is messy and uncomfortable – and many teams take the easy way out. They rely on generic benefits and buzzwords that sound just like everyone else, instead of answering the one question buyers care about: "What's in it for me?" This isn't exactly revolutionary. But when you nail it, everything changes. Visitors stop scrolling. They start sharing your solution internally. They share it with members of their team. Because you’re speaking to what they actually care about – solutions to the problems they’re dealing with now. Fixing boring headlines isn't complicated: 👍 Start with your customer's actual language from interviews and sales calls 👍 Ask "How does this solve a specific problem my buyer has right now?" 👍 Rewrite to connect their pain directly to your solution Here's the transformation: BEFORE: "The future of inventory control is here" AFTER: "Cut food waste in half. With AI-powered ordering and expiration alerts." Your buyers are always asking "what's in it for me?" If your headlines aren’t answering that question, they’re not doing their job. It really is that simple.

If you get this wrong nothing else matters Before you write an advertorial, you need to choose the main benefit or pain point that your entire piece will focus on. Pick the wrong one, and it doesn’t matter how good your copy is because no one will read it Some copywriters assume that if you do enough research, the right desire will magically reveal itself. But that’s not always true. Even with deep research, you’ll often come across multiple strong desires that you could lead with. So how do you narrow it down to the one that will actually make your advertorial work? Often, we'll test them in ads to a broader page or see what has worked for current or past competitors But sometimes, that’s not an option Here’s how we decide in those situations. Step 1: List Out Every Possible Core Desire Your research should already give you a list of potential desires. If you’ve been digging through customer reviews, post-purchase surveys, and competitor angles, you probably have 3-5 solid core desires you could focus on. Examples for a pillowcase • Prevents wrinkles (beauty-focused) • Keeps you cool (comfort/sleep focused) • Reduces acne (skincare-focused) Each of these are different and could completely change how your advertorial is written. Step 2: Rank Them Using Three Factors Now that you have your list, you need a clear system to determine which has the highest chance of success. Here’s the framework we use: Audience Size – How many people experience this desire? Is this a niche problem affecting only 100,000 people? Or is it a widespread problem affecting millions? The bigger the audience, the more potential customers. Intensity – How urgent or painful is the problem? Is it a minor inconvenience (2/10 intensity)? Or is it a daily struggle that affects quality of life (8/10 intensity)? The more intense the pain or desire, the more motivated someone is to buy a solution. Frequency – How often does the problem occur? Does it happen once in a lifetime (low frequency)? Or is it a daily frustration (high frequency)? The more frequently a problem occurs, the more top-of-mind it is. Step 3: Calculate and Choose the Strongest Desire Now, assign a score from 1-10 to each desire based on the three factors above. You can weigh them based on what's most important to you and then multiply them together to get a final score. Step 4: Test & Iterate If you’re still unsure, write multiple variations, each focusing on a different core desire. Run them both, track performance, and double down on the winner. -- The right core desire makes or breaks your advertorial. If you get it wrong, your copy won’t resonate no matter how well it’s written. But if you nail this step, you set yourself up for a high-converting page

Researchers ran a simple experiment. Two versions of a fundraising campaign with same photo, same story, same goal. One used the phrase “malignant tumors” in the headline, the other, a softer “illnesses.” The result? Naming the disease performed much worse. But this testing was on a crowdfunding platform with donors seeing saw multiple campaigns side-by-side. Further experiments were done to unearth the "why", which one never knows with standard A/B split tests. People were anticipating feeling distress when the disease was named and so they avoided it. Ok, so this matters if you’re writing for GoFundMe but what if you’re not? What if you’re a health charity, or a disaster relief group, or a hunger org, sending one message to one person? The lesson still holds, just not in the same way. In single-message environments like email, direct mail, social ads, or microsites, donors don’t have the easy out. There’s no carousel of emotional alternatives. But they can still disengage. They can skim, ignore, delete, toss, or scroll past. The avoidance is quieter, but just as real. And this anticipated distress goes beond just the word “cancer” in a headline. It’s the emotional burden you place on someone the moment they see your message and whether you give them a way to carry it. Naming the thing — the diagnosis, the trauma, the crisis — isn’t wrong, but it’s rarely the best first move. Especially not when it’s paired with a raw image or no narrative context. When you combine an unbuffered image with blunt, high-distress language, you’re almost daring people to shut down and many will do just that. This doesn't mean you hide the need, you just sequence it. Start with the person, not the pathology and build a narrative before you drop the weight of what’s wrong. You show rather than tell, drawing the reader in with something they can hold onto — a detail, a moment, an image that builds connection instead of shock. And when the hard part comes, and it should, you don’t leave them there, you offer a path forward because hope isn’t the opposite of need, it's the companion to it and it's the thing that lets the person stay in the story. Which one is better to you? Every morning, Mia asks if today’s the day she gets to go back to school. Her treatments have kept her home for months—but there’s a real chance that could change. OR Mia is battling stage IV neuroblastoma. She’s been undergoing aggressive chemotherapy and still faces a long road ahead. If your cause is distress-laden (and most are) you need to assume donors are regulating their emotions, consciously or not. Your job is to make that easier by framing it and making it bearable to feel.

In a world where AI recommends solutions based on detailed user prompts, it’s more important than ever to map your content to real pain points. So instead of starting with a keyword tool, we start with customer pain points. We ask: 👉 What problems are people actively trying to solve? 👉 What do they say on sales calls? 👉 What objections come up before buying? We dig through: transcripts, support emails, call notes and extract the real language people use when they’re stuck. Then, we reverse-engineer keywords from there. Not by guessing. By mapping real pain points to search queries. We avoid broad, high-level terms like: ❌ “content marketing” ❌ “inbound marketing” ❌ “SEO strategy” Instead, we look for high-intent keywords that address specific pain points, such as: ✅ “how to get leads from content marketing” ✅ “how to measure conversions from SEO” ✅ “how to write content for advanced audiences” These kind of topics are more representative of challenges our clients are trying to solve. When prospects are searching for how to solve these kind of problems, we’re the ones sharing how to solve them. They read our content, then reach out to us. Many businesses focus on high-level topics instead of focusing on the specifics of the problems their customers are trying to solve. The approach we take is what separates content that drives leads from content that only drives page views. 🔗 Want to see how to apply this strategy step by step? Read the full article — link in the comments.

Why your content isn’t working It’s not about writing more. It’s about writing better. If your content isn’t landing the way you want, here’s a step-by-step framework to refine and improve: 1/ Start with the headline Your headline is responsible for 80% of your post’s performance. Ask yourself: Is it specific? Does it create curiosity? Does it promise a clear benefit? Example: wrong: “Why LinkedIn Matters” → Too vague, no hook. right: “Why LinkedIn is costing you clients (and how to fix it)” → Specific, actionable. People won’t scroll down if your opening isn’t compelling. Use one of these: Ask a bold question: “Are your LinkedIn posts costing you money?” Share a fact: “95% of posts don’t drive results.” Create curiosity: “Most content creators make this mistake—are you?” If the first line doesn’t make them pause, they won’t keep reading. 2/ Structure your content for skimmers Most people don’t read—they skim. Make your content easy to digest: - Use short paragraphs (1-2 sentences). - Add bullets for key points. - Highlight the most critical insight. - If your post looks like an essay, simplify. 3/ Solve a problem Content that works always answers this question: what’s in it for them? Ask yourself: - Does this post solve a specific pain point for my audience? - Will this insight make their life easier or better? - Can they take action after reading this? If your post is about you, it’s time to reframe it to be about them. 4/ Nail the call-to-action The biggest mistake is ending your post with nothing. Here’s how to create CTAs that work: - Keep it simple: “What’s one thing holding you back from starting?” - Invite engagement: “Have you tried this? Let me know below.” - Offer value: “Save this post so you can apply it later.” Your audience needs a nudge—don’t leave them hanging. 5/ Iterate until it clicks Great content is a process. Here’s how to refine your next post: - Analyze past performance: what worked? what flopped? - Test new formats: lists, stories, videos—mix it up. - Experiment with hooks: try different approaches to see what resonates. Every post is data. Use it to get better. Engage with your audience The post doesn’t end when you hit publish. Reply to comments. Start conversations. Turn insights into follow-up posts. Content that drives engagement builds relationships, and that’s where results happen. Pro tip: Bookmark this framework and use it to audit your next 5 posts. Content isn’t about perfection—it’s about connection. Which step are you focusing on next? Let me know in the comments.