Episode 4 of Never Stop Dreaming BIGGIE features my first guest interviews with Sara Donahue and Randi Weinstein

“It was all a dream…” but what happens when you have the right people to help make those dreams reality?

In this week’s episode of Never Stop Dreaming BIGGIE, I had the absolute joy of sitting down with two of the most important people in my entrepreneurial journey – Sara Donahue and Randi Weinstein. These aren’t just business associates or industry contacts. These are my girls, my dream team, the women who’ve been there through every wild idea, every impossible challenge, and every moment of triumph.

The Power of the Right Team

When I think about building the Charleston Wine + Food Festival from the ground up, I don’t think about the accolades or the press coverage. I think about the people. Specifically, I think about Sara and Randi, who took my biggest, craziest visions and somehow made them happen.

Sara Donahue walked into my office as an intern and confidently declared her love for Excel spreadsheets. I knew immediately she was hired! After seven years with Charleston Wine + Food Festival managing everything from talent coordination to beverage sponsorships, Sara founded Cross & Dot in 2014. Her superpower? Living and breathing the “organized chaos” of events while eliminating communication barriers between teams and partners.

Randi Weinstein joined us in year two and became my Director of Events – the person who never said “that’s impossible” when I had my wildest ideas. Now she’s created FAB (Females in Business), a groundbreaking workshop for women in the food and beverage industry that offers “total transparency and zero bullshit.”

When Dreams Meet Reality: The Fort Sumter Story

One of my favorite stories from the podcast involves what we now call one of our “pinnacle events” – dinner at Fort Sumter. Picture this: I’m looking out at Charleston Harbor during an event at Patriots Point, I see Fort Sumter in the distance, and I turn to Randi and say, “We’re going to do an event there.”

Most people would have laughed. Randi said, “Yeah.”

What followed was logistical wizardry that still amazes me. We became the first and only group ever allowed to host a private event at this National Park Service site. Everything – and I mean everything – had to be transported by boat. Five chefs cooking with no power, using only period-appropriate ingredients, with historical reenactors delivering invitations via scroll during dinner service.

It was insane. It was impossible. It was absolutely magical.

The “See If It Sucks” Tour

Another highlight from our conversation was reminiscing about our legendary road trip we dubbed the “See If It Sucks” tour. As festival organizers, we were constantly booking chefs based on recommendations and press coverage, always wondering: “But are they actually good?”

So we loaded up a car (I had dreams of an RV that didn’t materialize!) and hit the road through Nashville, Birmingham, Oxford, and Memphis. Sara, Randi, our friend Lisa Buzelli, and I ate our way across the South, ending at Memphis in May – an event so wild that Sara, our logistics expert, was genuinely concerned about the safety of the double-decker tents with disco balls and beer funnels.

The trip culminated with an incredible 12-course meal at Andrew Michael Italian Kitchen in Memphis, where the chefs had prepared an elaborate dinner for a group of celebrity chefs who canceled last minute. Their loss was definitely our gain!

Building Community Through Events

What struck me most during our conversation was how both Sara and Randi understand that events aren’t just about logistics or entertainment – they’re about building community. Whether it’s Sara’s behind-the-scenes magic that brings people together or Randi’s FAB workshop creating spaces for women to “connect, communicate, cry, and commune together,” they get it.

Events are where relationships are born, where ideas are shared, where magic happens. But that magic doesn’t happen by accident – it happens because of people like Sara and Randi who understand that every detail matters, every person matters, and every connection has the potential to change someone’s life.

The Secret to Big Dreams

Here’s what I learned from years of working with these incredible women: You cannot do big things alone. Period.

I may be the dreamer, the one with the wild ideas and the “why not?” attitude, but dreams without execution are just wishes. Sara and Randi are the execution. They’re the ones who take my “wouldn’t it be cool if…” and turn it into reality.

But here’s the thing – people like Sara and Randi are rare. They’re unicorns in a world full of people who say “that’s too hard” or “that’s never been done before.” When you find people who not only believe in your vision but have the skills to make it happen, you hold onto them tight.

Finding Your Dream Team

As I shared in the episode, Sara and Randi will always be part of my world. When I was building Like Minded Charleston, I called them. When I started The Brighter Side Society, they were involved. As I prepare to open The Holmestead Bar & Retreat, they’ll be there too.

This isn’t just loyalty – it’s smart business. When you find people who complement your strengths and shore up your weaknesses, when you find people who get excited about your dreams instead of trying to talk you out of them, that’s when magic happens.

Your Takeaway

My challenge for you this week is simple: Find your Sara and Randi.

Look for people who:

• Say “yes, let’s figure out how” instead of “no, that won’t work”
• Have skills that complement yours
• Get excited about your vision
• Aren’t afraid of hard work
• Will tell you the truth, even when it’s difficult

And when you find those people, love them, appreciate them, and make them feel valued. Let them know that this isn’t a one-person show – it’s a team effort.

Because here’s the truth: behind every person living their biggest dreams, there’s a team of people who believed in those dreams too.

What’s Next

Want to hear more from Sara and Randi? Check out Sara’s company Cross & Dot for all your event consulting needs, and if you’re a woman in the food and beverage industry, you absolutely need to attend Randi’s FAB workshop (June 8-10 in Charleston – visit thisisfab.com).

And don’t forget to subscribe to Never Stop Dreaming BIGGIE wherever you get your podcasts. We’re just getting started, and I can’t wait to share more dreamers, more stories, and more proof that with the right team, anything is possible.

Until next time, never stop dreaming BIGGIE!

Listen to the full episode on Apple Podcasts, Spotify, or wherever you get your podcasts. Connect with us on Instagram @neverstopdreamingbiggie and @angelpholmes.

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About the Host: Angel Holmes is an entrepreneur, community builder, and host of Never Stop Dreaming BIGGIE podcast. She’s the founder of The Brighter Side Society, co-founder of Like Minded Charleston, and is currently developing The Holmestead Bar & Retreat. Learn more at sipindipity.com.