Exactly How I'd Build a (Fun!) $1M Wine Biz

My best friend Kendal is f*cking fantastic at three things (are you like this, too?):

1. Going—completely—with the flow.
   You could be stuck in an airport for 3 days in Cairo, Egypt, with greasy hair and lost luggage and body parts that smell more like pig parts, and she would totally just be sitting there in a great mood with her journal, doodling ideas, drinkin' an IPA, not a care in the world.
   
2. Making friends with LITERALLY ANYONE.
   Except, with her luck, she always ends up making friends with, like, the editor of Travel & Leisure. Or the CEO of an airline. Or a guy who happens to own a villa in Tuscany and gives her the keys to go stay with her friends when she feels like it. She has that kind of energy. Men, especially, are in awe of her, because she truly is 100% herself. No airs—and, she's a magnet.
   
3. And, finally, blind tasting any freakin' wine in the world and being able to nail it.
   That's because she's a big-ass wine expert, with her DipWSET Diploma in Wines (one of the most respected academic wine credentials in the world), and a Master in Champagne (yeah, that's a thing). This girl's job is literally traveling the world, picking out wines for distribution in the United States. When we met in Chile in our 20s, she got her first job working at Cono Sur, writing the labels for an English-speaking audience. My god, the fun we had.

So, we're *always* brainstorming creative business ideas together.

When I visited her in Brooklyn a few weeks ago, I couldn't help but plant the seed:

WHY DON'T YOU TEACH OTHER PEOPLE HOW TO CRUSH THESE EXAMS?

Because, I just can't help it.

When I can see a clear revenue stream, I just can't help it.

So!

Here is what I would do if I were setting this up for her (to actually make money from this venture, not let it sit there like a big, stale old leather shoe):

1. Set up one of the sexy (new!) landing pages on Kit (my affiliate link).
   
2. Give away a smart-as-hell, free guide that people studying for their Diploma in Wines actually want. Not something flimsy, like "5 Tips for Studying for the DipWSET" (doesn't feel worth exchanging your email address), but rather, something that positions you as a thought leader in your industry. For example, "The 2026 Wine Salary Insider's Guide: How Much You Can Make With Your DipWSET." Now that's something that will convert.
   
3. Now, this is important: every new subscriber that's coming in? You know they're legit leads, because who else would be subscribing to this if they *weren't* studying the DipWSET or considering a career in wine? This makes your email list approximately 42,000,000x more valuable than just collecting a bunch of randos.
   
4. As soon as they opt-in, I'm going to send them an automated email that's going to be super freakin' friendly, totally human, and that contains a very important piece of the puzzle: a poll. And, in that poll, I am going to ask them this:
   
   "Where are you in your wine journey?"
   • I'm thinking about DipWSET but haven't committed yet
   • I'm currently studying for my DipWSET
   • I recently passed my DipWSET (or other wine credential)
   • I'm already credentialed and exploring what's next
     
     Why this matters: Tells Kendal if she's selling aspiration (pre-study), confidence (mid-study), or career optimization (post-study). Completely different messaging and product angle for each.
5. Doing this really helps for another reason though: getting people to click on your email right away is going to tell Gmail (and other inboxes) that they actually want to get your emails. Which means you have less chance of ending up in spam (especially if your sending domain is new). This is critical. Do not skip.
   
6. Based on what they selected? They get tagged accordingly: Pre-Study, Mid-Study, Post-Study.
   
7. Then? Each tag gets a slightly different version of the same welcome email series, designed to speak to them exactly where they're at. Making people feel like you GET THEM? Really important in sales. (And, you can set this up once and make it run forever, so you can make every new subscriber feel this way.)
   
8. And then, the simplest way she could start cashflowing? Send each person into a sales sequence of emails that offers them a private invite to consult with her. Link it up to a scheduling tool like Savvy Cal (my affiliate link). And, done. ✅ Bookings coming in on autopilot. (Without you having to spam your whole list every week. Alas, the power of personalized offers using email automation. 💃
   
9. Of course, this could be more sophisticated, depending on the offer. Maybe she's running live cohorts that happen every quarter (and thus her offer would be to get in at a discounted early bird rate and join the next one happening X date). Or maybe she's selling a series of WAY more fun-to-read study guides, solving the problem of the whole "DipWSET is laborious to read." Whichever product she's selling, she can cater her pitch, depending on who she's talking to (which she knows from that initial poll).
   
10. And then? Her only job is to get people to see her lead magnet: The 2026 Wine Salary Insider's Guide: How Much You Can Make With Your DipWSET. But now, the job is easy: she's got an asset people are going to *want*. So, she sets up Buffer to automatically post about the guide every week on LinkedIn, between her other posts. (They have a "recurring post" feature that not many tools have. This ensures you're actively promoting your lead magnet without having to remember to do it all the time—and keep yourself as the bottleneck in yo' business!)
    
11. And, of course, she could always run ads to it, too, because it's a legitimate enough lead magnet that people are going to want to download it—so long as she is targeting people who are following the WSET page, for example.
    
12. Then? She magically grows her email list (the most important thing you can have). And with it, she grows a real business asset. In the future, she could pivot to any number of other offers around wine—retreats? Her own wine label? Other courses? Her own certificate? Or, hell, she could take on sponsors. Or, she could even at some point sell the business to a company that wants the benefit of the good will & reputation she's built.
    

This is just the tip of the iceberg ice wine.

And the best part?

It's actually dead simple to set up.

*Everyone* needs to be giving themselves the gift of a system like this, and a business asset like this. Because when it comes to creating your own wealth?

Email is the key.

And on July 1st? WE START, BABY. 👏🎬

I'm so happy to have you for The Summer Vacation Email Challenge!

The idea? Set it up once, and enjoy the rest of your summer. ☀️ 🍉⛱️🕶️

This is how we build systems that give us back our time.

This is how we create wealth.

This is how we make things that give us life (and not just take).

Inside, I'll show you how to set this up for yourself, step-by-step. You don't have to grind it out during the challenge in July, if you don't want to: the system will be there for you, anytime you want to log in and follow it.

It's built to be repeatable.

It's built to be a tool.

Let's use the technology we have, to make our lives better.

And then, like Kendal?

All you have to do...is go with the flow.

P.S. See you in your inbox with your log-in credentials the morning of July 1st! 🥇