Daily Inspiration: Meet Rachel Pineapple

Today we’d like to introduce you to Rachel Pineapple.

Hi Rachel, thanks for joining us today. We’d love for you to start by introducing yourself.
I started out training to be a counselor. I have the Master’s degree in Education in Counseling to prove it. But somewhere along the way, I realized what I loved most wasn’t the counseling, it was the connection and the people. Marketing found me from there, building the story around a brand and getting people to care about it, and I never looked back.

So I pivoted. Hard.

With over a decade of experience across the wine and spirits industry, I’ve held brand marketing roles for companies including Ciroc and DeLeón, and worked agency side for others such as Lobos 1707 Tequila, Pronghorn, and Bisquit & Dubouché, helping build brand strategy and cultural relevance from both inside the room and outside looking in. That dual perspective, in house and agency, now shapes how I approach my own ventures as a founding member and business owner.

Eventually, working on other people’s brands stopped being enough. I wanted to build my own. That’s how I became a founding member of IBest Wines, joining Ingrid Best and a group of standout women to launch the brand from the ground up. I hold equity in the company and also run day to day as Brand Manager, so my fingerprints are on nearly every part of it.

The entrepreneurial itch didn’t stop there. With my partner, Brandon, I created Lyrical Tug of War, a competitive card game that turns singing battles into a party staple, now sold on Amazon. And as if wine and card games weren’t enough range, we also opened Best Damn Chicken, a Chicago style chicken and fish restaurant in Chatsworth that wears its confidence right in the name.

Ask me what ties a counseling degree to wine, card games, and fried chicken, and I’ll tell you it’s never really been about the industry. It’s about the people. Building real connections is the skill that’s carried me through every new venture, and it’s the one thing that hasn’t changed since day one.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
If it was a smooth road, would it even be a story worth telling? Nothing easy is worth it. So no, none of this has been smooth.

With the wine, we started from the first building block. You strap up your boots and get to it. IBest Wines has been around for just shy of three years, and we’re already showing up in places most brands don’t see in ten. That’s not luck, that’s grind.

With Lyrical Tug of War, the obstacle has a name: tariffs. Sales on Amazon have been strong, genuinely exciting. But tariffs on goods coming from China sent our COGs up exponentially. Great sales don’t mean much if your cost of goods is eating the win.

And the restaurant? Whoo, chile. Opening Best Damn Chicken in a timely manner was a feat. The permitting process alone is grueling, every department, every requirement, all the little details nobody warns you about that turn out to matter 1000%.

Here’s what I’ll leave you with: read your leases and contracts to the T. Know what you’re entitled to. And do not let anyone try to get over on you.

Appreciate you sharing that. What else should we know about what you do?
Ask anyone at IBest Wines what I do, and they’ll tell you: I’m the glue. I’m technically a founding member, but as Brand Manager, that’s basically my day to day, I’ve got my hands in everything, marketing, ops, whatever needs to get done.

What we’ve built in under three years still doesn’t feel real some days. We’re in 17-plus Costco locations across Southern California. We’re in Total Wine & More across eight states. Our distribution runs through New York, New Jersey, California, Florida, Ohio, Massachusetts, Virginia, Maryland, DC, Georgia, and Texas, plus two countries in Africa, and we just locked in Illinois, which means more to me than people probably realize, since that’s where I’m from. On top of that, we ship direct to 49 states through our website.

Then there are the moments that still catch me off guard. We’re served at the Hollywood Bowl. We’re poured in American Airlines First Class International and the LAX Flagship Lounge. We’re in museums, attached to cultural art shows, and most recently, we landed in Usher’s green room and on his VIP risers for the R&B tour. And there are some ridiculously big things happening for us toward the end of September going into the end of the year, more on that soon.

The restaurant side is teaching me something different. You can post the same thing on Instagram a hundred times, and people still won’t connect the dots unless you spell it out, “I own this.” I get messages constantly, people telling me I “have to come check out” a place I post literally every day. I just laugh, because it taught me that visibility and ownership aren’t the same thing, you have to say it plainly.

We’ve had people like Kendrick Perkins, Kevin Garnett, Lou Williams, Lil Rel Howery, Kel Mitchell, Rolando Boyce, and Chief Keef come through, and that’s genuinely exciting. But if I’m honest, the real MVPs are the regulars, the ones who show up and order on a random Tuesday because they actually love the place. We’re closing in on one year, and it’s because of them, plain and simple.

Risk taking is a topic that people have widely differing views on – we’d love to hear your thoughts.
Am I a risk taker? I don’t really think of it that way. I just don’t believe in waiting for the “right time,” because the right time is a myth.

Here’s what betting on myself actually looked like, in real time, between October 2023 and September 2025. That’s when IBest Wines was launched. A year later, in October 2024, we launched Lyrical Tug of War. In the middle of all of that, I was carrying a high risk pregnancy.

I’d had 17 fibroids. Fifteen were removed in December 2022, but two stayed behind. Fibroids feed on hormones, and pregnancy floods your body with them, so those last two grew fast, positioned on both sides, crowding the space my baby needed to move. That’s what “high risk” actually meant for me. It’s more common than people realize, especially for Black women, we’re diagnosed with fibroids at nearly three times the rate of white women, and by 35, more than half of us have them. It’s just rarely talked about.

My son was born in March 2025. By June, we’d started renovations on Best Damn Chicken. By September, we officially opened.

Two brand launches, a high risk pregnancy, a newborn, and a restaurant build, all inside two years, with almost no gap between any of it. I didn’t wait for the right time because I don’t believe it exists. I say yes first and figure out the how later. That’s the only kind of risk I know how to take.

Contact Info:

• Website: www.bestdamnchicken.com, www.ibestwines.com, www.lyricaltugofwar.com
• Instagram: @thepineapplepapi, @thebestdamnchicken @ibestwines, @lyricaltugofwar

Image Credits
Jorge Meza : Main image, image in pink, image with 3 ladies and bottles