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Life, Values & Legacy: Our Chat with Dasha McHale of Tampa, FL

We’re looking forward to introducing you to Dasha McHale. Check out our conversation below.

Dasha, a huge thanks to you for investing the time to share your wisdom with those who are seeking it. We think it’s so important for us to share stories with our neighbors, friends and community because knowledge multiples when we share with each other. Let’s jump in: What do the first 90 minutes of your day look like?
The first 90 minutes of my day? Oh, it’s my sacred time. I’m hoping to be a part of the 5 AM club one day, but for now I’m up by 6 AM, start with kiddo cuddles that could melt steel, sweat through a workout, then hit the shower. Finally, I crown it all with a cup of coffee so good it’s practically a religious experience.
Same routine every day—and I wouldn’t change a thing. It’s my launch sequence for success!

Can you briefly introduce yourself and share what makes you or your brand unique?
Hi there! I’m Dasha McHale—the face, the brain, and the glass-holder behind My Wine Diary on YouTube and founder of The Unwined Group. I’m a WSET-certified wine specialist, educator, and content creator with a mission: to make wine less intimidating and a lot more fun for everyone.

For over five years, I’ve been pouring (pun fully intended) my heart into teaching communities about wine—whether it’s through engaging YouTube videos, lively virtual and in-person tastings, or partnering with brands that want a fresh, knowledgeable voice in the wine world.

What sets me apart? I blend wine with a little bit of everything: a decade-long career in sales, a yoga mat (I’m an RYT500 instructor), a passport full of travel stamps, and a kiddo who reminds me daily to keep things joyful. I bring all those layers into my work to connect with people in real, relatable ways—because wine shouldn’t be scary, it should be sipped and savored with a smile.

Amazing, so let’s take a moment to go back in time. What’s a moment that really shaped how you see the world?
One moment that truly shaped how I see the world happened during an incredible honeymoon trip through Peru with my husband. We had just made it through the Sacred Valley to Machu Picchu—a little tired, heart full—and I found myself sitting in quiet awe, overlooking those ancient ruins with my partner next to me. The stillness of that moment, high above the clouds, shifted something in me.

Later in Lima, wandering through vibrant markets and chatting with locals over pisco sours (a type of brandy distilled from grapes!), I began to feel a deep sense of clarity: everything I had ever dreamed of doing—teaching, creating, connecting, traveling—wasn’t some far-off fantasy. It was possible. It was already beginning.

Since that moment, I started to understand the power of alignment—of doing what lights you up and sharing it with others. It was my first real glimpse into ikigai: the sweet spot where passion, purpose, and service meet.

Since then, I’ve carried that lesson with me—into motherhood, into building My Wine Diary and The Unwined Group.
If you can dream it, you can absolutely do it! The key is trusting the process, staying grounded in your truth, and never underestimating the magic of saying yes to yourself.

What did suffering teach you that success never could?
Suffering taught me presence-deep, raw presence-that success never could.

In moments of struggle, whether it was rebuilding myself after personal setbacks, navigating motherhood without a manual, or launching a business with nothing but vision and grit, I learned to sit with discomfort instead of rushing past it. Success often comes with momentum, but suffering whispers the truths you only hear in stillness.

It taught me resilience. It reminded me that vulnerability is not weakness; it’s wisdom. That not every day will sparkle, but every single one carries a lesson if you’re willing to look. Through yoga, travel, and wine-yes, even wine!-I found rituals that helped me alchemize pain into purpose.

Suffering cracked me open in the best way. It taught me humility and how to honor the journey, not just the destination. Success may be the reward, but suffering was the teacher! And for that, I’m very grateful.

Next, maybe we can discuss some of your foundational philosophies and views? What are the biggest lies your industry tells itself?
Oh, where do I begin? One of the biggest lies the wine industry tells itself is that complexity equals credibility. There’s this long-standing myth that wine has to be exclusive, snobby, or overly academic to be respected-and that if you don’t speak in tasting notes that sound like poetry, you’re somehow not “serious” about wine.

Another big one? That consumers need to be educated to enjoy wine. Truth is, people are already experts in what they like-they just need someone to help them feel confident saying it out loud. That’s where I come in. My mission has always been to demystify wine, not dumb it down-to bring approachability and realness into a wine world that can sometimes feel like it’s unfriendly.

Also…can we stop pretending rosé is only for summer and women? That’s another lie I’d love to see corked for good!

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. What do you understand deeply that most people don’t?
What I understand deeply-through both experience and a lot of inner work-is the concept of antifragility. It’s more than just bouncing back from challenges. It’s about growing because of them. In business, in motherhood, in yoga, in wine-I’ve learned that the things that challenge us, shake us, or even break us a little are often the exact things that strengthen us if we allow them to.

Most people aim for resilience-they want to “get through it” and go back to how things were. But I’ve found that the real magic happens when you lean into discomfort and let it reshape you into something stronger, sharper, and more aligned.

It’s not about being fearless. It’s about welcoming the chaos with curiosity, knowing that every difficult situation carries an opportunity-if you’re paying attention. That understanding guides how I show up in my work and my life: with flexibility and a trust in the process.

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Image Credits
Courtney Semler

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