The $4,000 Email I Almost Didn’t Send

Sometimes I almost wanna slap myself.

Take yesterday for example.

I nearly let a $4,000 opportunity slip away just because I was feeling a little uncomfortable about sending an email.

Here’s what happened:

A month or so ago I did a deal with a software development company that wanted to sponsor the Simple Programmer email newsletter.

(At Simple Programmer, the bulk of our revenue comes from product sales, but we get about a quarter of it from sponsors who pay to advertise to our audience.)

This sponsor did a “trial run” with us to promote a couple of lead magnets—a webinar and a “white paper”—in our newsletter.

After the ads ran I got an email from their marketing person saying how thrilled they were with the results.

Great, I thought, and made a note to follow up with them to see if I could get a long-term sponsorship agreement in place.

And then… I sat on it.

A month went by, and I did nothing.

Here I had a customer, essentially, who’d already spent a couple of grand with us…

Was ecstatic about the results they got…

Could likely afford to throw a lot more money our way…

And I hadn’t followed up.

Sound familiar?

Most businesses do this ALL THE TIME, ignoring their happiest, bestest customers.

I should know better, but hey it happens to everyone.

In hindsight I was procrastinating because I felt uncomfortable going back to them and asking for more money.

Anyway, at our weekly team meeting my business partner John asked me whether I’d followed up on this yet.

I hung my head and admitted I hadn’t—but I committed to get it done this week.

When I sat down to write the email I realized that this was actually easy.

Rather than making a vague ask of “do you want to extend your sponsorship,” I made a *specific* offer: By booking a 3-month block of newsletter sponsorships, they could save 33%.

I gave a deadline: I needed to hear back by Friday.

And I added a dash of scarcity: We have another sponsor who’s interested if they weren’t.

Within an hour I had a reply:

YES, we want to book the whole quarter, please send us an invoice.

$4,000 deal, just like that.

Wow, can’t believe I waited so long to do that.

When was the last time you contacted YOUR best customers with a specific, time-limited offer?

Chances are a few are dying to throw money at you if you’ll just give them the opportunity…

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