Five Years In: Lessons Learned Leading Purple Cork

Celebrating five years of tastings with the best customers I would wish for

Five years ago, I wrote a blog post called “Reflecting on Purple Cork: 8 Months In.” I had just taken the leap into the world of entrepreneurship, heart full of excitement (and maybe a little rosé-fueled adrenaline). Purple Cork was a baby startup with big dreams. Today, we’re five years in—and while our wine tastings are as crisp and impactful as ever, the company has matured quite a bit.

This time around, I wanted to share some of the lessons that have stayed with me—and the ones I had to learn the hard way. If the early days were about saying “yes” to everything, these days we’re about clarity, focus, and pouring joy into the work every single day.

It’s All About the People

If there’s one thing I know now, it’s that business is people. Our clients, our partners, our team—they’re the secret sauce. I’ve been lucky to work with some truly incredible people over the years, and I’ve learned that when you prioritize people—really invest in them—the results follow. Culture isn’t something you write in a handbook; it’s something you feel when your team rallies for each other at midnight before a big event. It’s in the laughter that fills our Zoom tastings, and the way clients return year after year, trusting us to deliver joy in a glass, and refer us to their peers.

Say No (But Nicely)

In the early days, my instinct was to say “yes” to everything.
“Can you do an event for 400 people on five days’ notice with a custom cocktail and a comedian?” Yes!
“Can you fly across the country to hand-deliver a bottle?” Yes!

We were fueled by hustle.

But five years in, I’ve learned that experience is what gives you the confidence to say no—or better yet, to say, “Here’s what will actually work better.” Clients don’t just come to us for logistics; they come to us for our expertise. We know what creates magic, what feels clunky, what wines actually help clients close deals. Saying no isn’t closing a door—it’s guiding someone toward a better one.

Know What You’re Good At (And Own It)

There’s a general store near Harvard with a sandwich counter that locals love. One day, an employee suggested expanding the menu—maybe add eggs, do omelets, offer breakfast. But the owner pushed back with something simple and wise: “We’re a sandwich shop. People come here for sandwiches, not omelets.”

That line stuck with me. It’s a great reminder of how powerful it is to know what you’re best at—and why people keep coming back.

At Purple Cork, we’ve learned to embrace our lane. We’re not trying to be a gifting service, a wine club, or an event planning company that dabbles in everything. We’re experts at crafting thoughtful, high-touch tasting experiences that bring people together—virtually or in person. That’s what we do. That’s why people come to us. And every time we try to do “more,” we ask ourselves if it serves that core experience. If it doesn’t? No eggs.

My Role Has Changed. A Lot.

In year one as a founder, you basically do it all. Now my days are spent very differently.

My biggest responsibility is sales: growing the business and keeping the team energized. That means staying close to the ground—understanding what’s working, what’s not, what our clients are craving—but without micromanaging. It’s a balance between leading and letting go. I like to think of it like a winemaker checking on the barrels: close enough to know how things are aging, but trusting the process.

Listen: Your Clients Will Tell You What They Want

Some of our best offerings started with a client saying, “Could we try this?” And instead of thinking, “That’s not what we do,” we said, “Tell us more.” Listening has become one of our greatest competitive advantages.

When you have great clients—and we do!!—they’ll push you to innovate in ways you might never have imagined. Blind tastings, hybrid tastings (“Choose Your Pour”), celebrity appearances—it all started with a simple conversation. Sometimes the best ideas aren’t on your whiteboard. They’re in your inbox or on a client catch-up call.

And Finally: Have Fun

It’s okay to have fun at work! We all need more fun in our lives.

Work is hard. Startups are even harder. But we’re in the business of joy. If we’re not enjoying ourselves, our clients will feel it. So we celebrate the wins. We laugh. We toast each other often. Fun isn’t a perk. It’s the culture.

Five years ago, I ended my first blog post with:
“It’s been a whirlwind, and we’re just getting started.”

That’s still true. The only difference? Now we have 60 months of memories, thousands of events completed, and people all around the world who’ve laughed and learned with us, glass in hand.

To everyone who’s been part of this journey—thank you. You’re the reason we keep going.

Here’s to the next chapter!

See you soon,

Kelly