Creator success stories: Kyle Weeks’ wine wins

Creator success stories: Kyle Weeks’ wine wins

During our 2019 Reach Summit, we introduced three Teachable members with very different paths to success by asking them to write a letter to future independent entrepreneurs. Meet Kyle Weeks of Wine Primer below:

“So…what do you smell?”

That was the question posed to me by a Master Sommelier standing at the front of the 100-seat lecture hall. To say this man has merely “studied” wine for decades would be…kind of insulting. His commitment to his craft has made him one of only 149 Master Sommeliers in the United States.

I was being put on the spot in front of my peers, being asked to “blind taste” a white wine—that is, to identify the wine by talking through methodical, detailed observations of how the wine looks, smells, and tastes.

Trying to guess a wine is nearly impossible.


Because I learned that with specific techniques, blind tasters can actually increase their odds of success and consistently guess right.

As content creators, we, too, set out to do something nearly impossible: to communicate something “original,” something that entertains, educates, or empowers, all in a way that inspires others to follow along.

And then, some of us choose to embark on something seemingly more impossible: to make a living from our content.

Through recently publishing my first course on Teachable, I’ve come to learn that—as it is with learning to blind taste—the only way we can successfully monetize our content is to make intentional moves to improve our own odds and there are a few good ways to do it:

Leverage a system and tools

When sommeliers blind taste, they ask themselves a standard set of questions about the wine. This system allows them to spend all their mental effort on analyzing the wine instead of figuring out how to analyze it. Similarly, as a new course creator, I can spend all my mental effort on the strength of my content while Teachable handles hosting, payments, student management, and more.

Get your reps in

“But like… how do you train your palate?” my peer asked our instructor one day.

“Want to learn to identify the subtleties of a Noir? You need to go try 500 of them,” came the reply.

It wasn’t until later that I understood the wisdom in that statement. When learning any skill, it’s only through repetition that we experience growth, like a bodybuilder doing reps in the gym. As a content creator, I’ve learned I don’t often hit the target with the first piece of content I put out on a subject. Instead, I must consistently put things out there until I understand the nuances of what’s working and what’s not, until I truly understand what my audience’s needs are—and what they’d be willing to pay for.

Teach yourself through teaching others

Part of why I chose wine as the subject matter of my first Teachable course is that I wanted to go deeper in my knowledge. When we teach others, we learn. The beauty of teaching an online course is that you end up being the student—you’re forced to go deeper into your subject matter. The experience of launching a course is bound to teach you a thing or two about building an audience, running a business, or, perhaps, simply finding your own voice.

So whether it’s putting out your first Teachable course or going deeper in something you’ve already started, I encourage you to take the next leap, to change your odds of conquering that mountain that, from your current vantage point, looks impossible to climb. It’s time to go for it!

To the impossible,

Kyle Weeks

Wine Primer

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