Headlines, Headlines, Headlines

When it comes to copywriting in advertising, the most important thing you can do is improve the headline.

The same goes for video; if the first 3 seconds are boring, people have moved on.

Legendary advertising David Ogilvy has said, “If you haven’t done some selling in your headline, you’ve wasted 80% of your effort.“

Here’s how I focus on perfecting the headline (when I’m not incredibly time-poor and rush it).

• Start with a Number (signal time + value fast)
  Use a clear number to show how quick and digestible the content is (e.g., “3 steps,” “5 frameworks,” “7 mistakes”) so the reader instantly thinks: high value, low time cost.
  

• Make the “What” painfully clear (clarity > cleverness)
  Say exactly what you’re giving the reader (templates, habits, strategies, frameworks). If they can’t understand the topic in one second, they will scroll.
  

• Name or imply the “Who” (call out the audience)
  Either directly state the target reader (e.g., “for founders,” “for case managers,” “for marketers”) or make it obvious who it’s for so the right people instantly see themselves in the headline.
  

• Include the “Why” (the payoff or consequence)
  Tell them why they should care:

  • Positive: what they gain (attention, growth, results)

  • Negative: what they avoid (failure, wasted time, lost opportunities)
    

• “Twist the knife” (stack outcomes to increase urgency)
  Add multiple desirable gains or painful consequences in the headline to deepen relevance (e.g., “get more clicks, more trust, and more conversions” instead of just one benefit).

Every time I deviate from this structure or experiment with something else, I regret it.

Distracterations

You wouldn't believe how many businesses die getting distracted.

You're especially vulnerable when you're new, and any revenue seems better than none. It’s actually one of the dark secrets of the venture capital industry.

VCs put so much pressure on startups to grow that many commit what would otherwise be an unforced error.

I've been tempted a bunch of times to build Gravy (fundraising for nonprofits).

"If you can do this for us, this is what it could be worth to you"

On three occasions now, we've turned down opportunities worth $100k+.

We've even turned down what would have supposedly netted us $500k a year.

That might seem a little crazy, but it's not really.

See, when opportunities like this come along, it's easy to let yourself see that money already sitting in your bank account.

But, like most times in life, when something is too good to be true, it is in business as well.

In my experience, there are two reasons why these opportunities are not what they seem.

First, there's the tyre-kickers.

They talk a big game, but when it comes to doing, they disappear. You can waste weeks doing all sorts of things for them, only to be ghosted.

But they're easy to avoid. Just ask them to do something.

"Can you send me a written proposal?" or "Sign this letter of intent" Anything along those lines works. You'd be surprised how little amount of action it takes to get rid of talkers.

Second, they come with costs.

Often, outsized opportunities require you to do something different, and it's easy to underestimate the cost of different.

But a sense check with AI can now give it to you straight in minutes.

I've found that after digging into the details, the extra revenue is often achieved at much lower margins than business as usual.

Not to mention the havoc this distraction can wreak on your good revenue from business-as-usual.

I've fallen for both these traps more times than I'd care to admit. And it sucks when it happens. It makes you feel like you've been wronged.

But really, I've just been naive, and it’s completely avoidable. The grass isn't always greener on the other side.

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Have a great weekend!