I Made a Bet with My Son & Taught Him a Lesson

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The Story

I had a friendly bet with my soon-to-be-a-teenager son Keoni today. I’ll paint the scenario so that you can play along too…

It’s the day before another school year begins and my wife April asks me if Keoni had gotten his haircut yet.

He did not.

So, I called our favorite haircut place to ask what the wait times were.

After I hung up, I called Keoni down and said, “Hey bud, OVER or UNDER on wait times for a haircut today?”

That’s code for “do you want to play a game where you guess ABOVE or BELOW a certain number I give you?”

He said, “Sure! What’s at stake?”

“A cheesesteak.” I replied.

“Yes!” he said with a smirk. “What’s the number?”

“2 hours. Over or under?”

After a curiously long pause Keoni finally replied, “Under. It’s got to be under.”

What do you think? Over or under?

Well, let me just say that the cheesesteak I ate tasted extra good, mostly because it was free.

The total wait time for a haircut today: 3 hours and 5 minutes. OVER, by a longshot.

As we sat there eating our cheesesteaks, I took the opportunity to do what I normally do in these types of situations: teach my son a lesson in how people think and behave.

Most people wait until the last minute to do and decide most things, just like how we (and the rest of the neighborhood) waited until the last day before school began to finally get a haircut.

Without a deadline and without something at stake, there will likely be no action or decision made.

For my son, the context was related to goal-setting, homework, creating self-imposed deadlines, using a calendar, getting ahead and generally just being prepared for having to step it up in the 7th grade this year.

For you, the creator and entrepreneur, the context is this:

Chart of Teachable sales showing daily sales with a seven day sale at the end. Daily sales spike at the end of the campaign, with the highest daily sales on the last day.

This is a graph showing the revenue from a recent 7-day course sale in our company. Can you see when most of the sales came in?

Here’s the breakdown, income report style:

Here’s another example from a recent 3-day sale we just ran, too:

A chart showing daily sales over three days. The highest sales came on day three.

The breakdown:

This last minute pattern holds true for every single sale that we’ve done, and the more we highlight the deadline to decide the more sales we see right before the deadline.

Every. Single. Time.

Plain and simple: unless there’s a reason for a buyer to make a decision now…they won’t.

Here are three key takeaways from all of this:

  1. Legitimate, authentic marketing is about helping people make a decision, one way or another. More specifically, it’s about helping people make the right decision for them.

    It shouldn’t be about trickery or over-promising, but being honest and upfront about what’s being offered, the transformation that’s on the other end, and giving them a reason to make a decision now. Even if they pass on your offer, that’s a good thing – that means they made a decision.
  2. During a sales window, you must highlight (and repeat highlighting) when a decision needs to be made and what’s at stake. We may send up to 3 emails on the final day of our sales window to warm audiences, and each email converts progressively more.

    None of this will work unless you truly believe and know that your product or service actually helps people. Without that, selling will feel icky to you and to your audience. But, when you come from a place of service, the pressure you offer to make a decision shifts from “sales pressure”, to “service pressure” – the idea that you’re encouraging a decision because that’s the only way to begin and best serve your people.

Your Call to Action

If you’re stuck selling a product or service with little to no movement, insert a flash sale into the calendar within the next month. Provide a small window (i.e. 3-5 days) to take advantage of an offer that will go away, whether it be a bonus or even a discount. You could align this with a season or event (like a “Back-to-School Special”, if that makes sense for your brand), or just because.

If you don’t have a product or service yet, think about a reason to push a decision to join your email list. Perhaps there’s a special training you could offer, or even a limited-time lead magnet that relates to your audience that goes away or gets removed after a certain point. It can always come back later, but having the deadline will increase your conversions like crazy.


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  • Pat Flynn

    Hi, I’m Pat, founder of SPI and host of the Smart Passive Income Podcast. Let’s continue the conversation over in our communities.

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