We caught up with the brilliant and insightful Chris Beasley a few weeks ago and have shared our conversation below.

Hi Chris, thanks for joining us today. Alright, so we’d love to hear about how you got your first client or customer. What’s the story?

If I were an expert business person like, Forbes cover, TED Talk, wear-a-watch-just-to-check-the-time-on-my-phone level, well then I’d probably say something slick like, “It’s important to align with businesses and clients that reflect your core values.”

But the truth? I lucked into my first client because I was just trying not to get divorced on Valentine’s Day.

Here’s what happened.

It was February 14th. My calendar had a giant heart drawn on it and nothing else. I realized I had nothing planned. Not a reservation, not a flower petal, not even a sad grocery store teddy bear. Just vibes and anxiety.

So I jump on Yelp like my marriage depends on it. I scroll through a hundred places that are all either fully booked or suspiciously closed “due to plumbing issues,” which, on Valentine’s Day, just means “we hate love.” Then I find this stunning little spot I’d never seen before. I hit OpenTable like I’m disarming a bomb. Boom. Table for two. I don’t even question it. I book it. We get in the car. I’m hoping for brownie points—but I have no clue if this is actually going to impress her or just be, you know, “a place that sells food.”

We get there. The vibe is immaculate. Romantic lighting, people clinking glasses, jazz music playing like a Netflix montage about to happen. We’re halfway through dinner, things are going really well, and then suddenly, a manager walks up to our table looking concerned. My heart drops. I’m thinking, “Oh God… did I book this under the wrong name? Did I steal someone’s table? Is there a secret dress code and they’re about to bounce me for wearing Jordans?”

But no. Turns out he had the wrong table. He was coming to handle a complaint but not ours. We hadn’t said a word. In fact, I was working so hard to make sure this night was perfect, I would’ve eaten raw squid and smiled like it was steak.

But here’s where it gets cool.

We tell the manager, “Nah, we’re having an amazing time.” And we actually mean it. We start gushing about how beautiful the space is, how good the food is, how the whole night feels like a plot twist where I actually did something right. He’s relieved. Goes to deal with the actual problem table, and when he comes back, he thanks us for the positivity.

We start chatting, as one does when you’re full and suddenly confident, and we let him know we’re new to the area. He offers to show us around the venue. And man this place? Gorgeous. Like “your mom would cry at the wedding photos” level of pretty.

Somewhere in that tour, we start spitballing ideas. Not a pitch, just honest conversation. Talking about the future. Talking about art, events, community… you know, real “what if” energy. And somehow, our visions line up. We’re not forcing it. It’s not some LinkedIn networking moment. It’s just vibing with a human being.

Fast forward a year and a half later, after staying in touch, trading ideas, and slowly building trust, that venue became my very first client.

And the best part? I was already a fan. I was already a customer. I didn’t have to fake excitement. I already believed in what they were doing.

So yeah, if I was an expert business person, I’d say, “Align with clients you already believe in.”

But if I’m just being me?

I’d say: try not to mess up Valentine’s Day. Sometimes, that’s all the business plan you need.

Chris, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I’m a comedian and show producer, but honestly, I didn’t get here on purpose. I got here because life tackled me. Literally.

I was playing sports, feeling athletic, invincible, you know, like a young LeBron. Then I tore my Achilles. Thought that was bad? It got worse. Developed blood clots, which turned into a pulmonary embolism, and next thing you know I’m laid up in the hospital thinking, “Well… this sucks.”

But something shifted in that hospital bed. I had this strange moment of clarity, like a message from above cutting through all the pain. “When I get out of here, I’m doing stand-up.” I don’t know where it came from, but it felt bigger than me. So I signed up for a comedy class while still on crutches. First time on stage, I was limping, but I felt more alive than I had in years. And I’ve been hooked ever since.

As I got deeper into the comedy scene, I noticed something. Most shows weren’t exactly fancy. They were in basements, bars, or backyards. None of which scream “date night” or “bring your mom.” I started asking, “What would it take to get my mom to one of my shows?” And that’s how Grapes and Giggles was born.

I wanted to create a comedy experience that felt like a full night out. Great wine, good food, beautiful venues, and legit stand-up. Not deep in the city. Not stuck in traffic. Just real comedy in places people actually enjoy being. We started doing shows in wineries, upscale restaurants, and cool suburban spots, and people loved it. It took off.

Now we’ve got this thing where you can laugh hard, sip wine, and not feel like you’re sacrificing your standards to have a good time. I’m proud of that. I’m proud we made something where people can connect, laugh, and feel like they’re part of something special without needing to hunt for parking in downtown chaos.

At the end of the day, I just want to help people laugh again. Whether I’m on stage or producing the show, the goal’s the same. Make the night memorable. Life hit me hard, but comedy hit back. And I wouldn’t change a thing.

How’d you build such a strong reputation within your market?

I think what helped build my reputation is that I’m one of the strictest bookers in town, and that’s by design.

I’m hard on comedians, not because I don’t believe in them, but because I care about the audience and the venue. I know my shows aren’t in traditional comedy clubs. They’re in wineries, upscale restaurants, outdoor patios. Beautiful spots that weren’t built with comedy in mind. That means the show has to overcome those challenges, and the performers need to be prepared for that. I think of the show first, always.

My job is to partner with stunning venues and build something so undeniable, so enjoyable, that people have to come back. And that only happens when the talent is just as undeniable. So yes, I’m strict. I curate the lineups like a chef curates a tasting menu. Who goes first, who hosts, who closes. All of it matters. The audience shouldn’t have to sit through a single slow moment.

At the same time, I’m not just gatekeeping. I’m building a pipeline. I produce smaller gigs and give comics reps so they can grow into the kind of performers who shine on my main stage. I’m honest with them. I want them to succeed, and I give them opportunities to develop their skill set. But once they’re on the show, the bar is high, and I make that clear.

It’s also about brand clarity. Grapes and Giggles has a name that works. The branding is clean. The design is sharp. It’s not just a comedy show, it’s an experience. People come because they know they’re getting something special. Good wine, good company, and a lineup that delivers from top to bottom.

Early on, I thought I had to be at every show to make sure it ran right. I hosted, greeted guests, checked mics, did everything. But that wasn’t scalable. So I started training others, trusting the process, and now I’m proud to say the show runs without me. That’s how you know the brand is solid. It’s not about me anymore. It’s about the experience. And that’s what people come back for.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

I lean heavily on those that came before me. I didn’t reinvent the wheel—I studied it, rode it, then added my own flair. The truth is, there are so many producers, ebooks, videos, and social media gurus who have been in this space longer than I have. I found three producers I respected and just watched. Learned. Took notes. And then I started swinging for the stars.

I iterated on their ideas and tried my own things. One of the biggest turning points for me was when I asked a venue for a retainer. I remember thinking, “Who do you think you are?” Like I was the one making the demands. I was shaking when I sent the email. But I had watched so many mentors burn out because they carried all the risk. They fronted everything and got paid last.

So I tried something different. I asked for buy-in from my very first client. I made it clear: if we’re going to do this, we’re doing it as partners. And to my surprise, they said yes. No hesitation. That gave me a real runway to build something without drowning in stress from day one.

So for me, the resources that changed my thinking weren’t always books. They were people. They were lived examples. I think the key is to listen, learn, and then be bold. Take the swing. Even if your voice shakes. Because they don’t always know you’re nervous. Sometimes all they hear is confidence.

Contact Info:

• Website: https://www.grapesandgiggles.com/
• Instagram: https://www.instagram.com/grapesandgigglescomedy/

Image Credits

Dominick Chirichillo (venue owner enjoys the show)
Aivy Cordova (Performs on stage)