If you’ve noticed more done-for-you event services popping up around Tampa Bay lately, you’re not imagining it. In this episode of Palm Harbor Local, we sat down with Jenna Densler, founder of Oaks and Iris Mobile Bar and Content Theory Tampa Bay, to talk about what it really takes to start a business, stay consistent, and stand out in a world where attention is the new currency.
Oaks and Iris mobile bar Tampa Bay is a strong example of how creativity plus execution beats perfect planning every time.
Jenna’s story started simply. She had a hospitality background, a Pinterest board, and a willingness to try before she felt fully ready. The rest came from showing up, improving along the way, and leaning into her natural creativity.
Creativity Is What Separates Average from Memorable
Jenna describes her mobile bar as “almost like cooking.” It’s not just pouring drinks. It’s creating an experience.
Instead of basic cocktails, she focuses on:
• Custom drink menus tailored to the host
• Seasonal twists like maple pecan old fashioneds
• House-made syrups and elevated garnishes
• A clean, polished aesthetic that photographs beautifully
Her point is simple: people don’t hire a bartender. They hire an experience.
When it looks good, tastes good, and feels intentional, people talk about it.
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Why Failure Is a Necessary Part of Growth
One of the strongest themes in this episode was Jenna’s mindset around failure.
She doesn’t avoid it. She expects it.
When she started Oaks and Iris mobile bar Tampa Bay, the upfront investment was manageable. That allowed her to move without overthinking.
She believes people should fail — especially when the risk is reasonable. The bigger danger is quitting too early.
She sees this pattern often:
• Business owners try to do everything themselves
• Marketing becomes inconsistent
• Growth slows
• They assume marketing “doesn’t work”
The real issue isn’t marketing. It’s lack of consistency.
When you show up long enough, momentum compounds.
Word of Mouth Only Works If People Can Find You
Today, over 80 percent of Jenna’s clients come from referrals and word of mouth.
But that didn’t happen by accident.
She made sure she was visible online from the beginning. Most of her discovery happens through Google, and Instagram helps close the decision because people can see exactly what they’re booking.
That combination matters.
If someone hears about you but can’t quickly confirm you’re legit online, they hesitate.
Guest Links:
Oak & Iris Mobile Bar: https://oakandirismobile.com/
Instagram: https://www.instagram.com/oakandirismobilebarservice/
Content Theory Tampa Bay: https://www.instagram.com/content_theory_tampa_marketing/
Starting a Business Requires Identity Before Strategy
Jenna emphasized something many people skip: clarity.
Before tactics, you need:
• A defined brand vibe
• A target audience (even if it evolves)
• A visual identity
• An understanding of your competition
She originally thought weddings would be her primary market. While weddings remain strong, she discovered demand expanded into:
• Corporate events
• Grand openings
• Birthday parties
• Private residential events
The lesson? Start with direction. Adjust based on demand.
How the Mobile Bar Booking Process Works
If someone books Oaks and Iris mobile bar Tampa Bay, the process is straightforward:
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A consult call to understand the event and vibe
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A customized alcohol shopping list
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The host purchases the alcohol
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Jenna and her team handle setup, service, and cleanup
Because Oaks and Iris operates as a dry bar for hire, hosts often save money by purchasing alcohol themselves.
It’s efficient, licensed, insured, and stress-free.
The Social Media Advice Every Business Owner Needs
Jenna sees two common mistakes:
First, overusing generic promotional flyers instead of real photos.
Second, inconsistency.
Her advice is simple:
Just start.
Post your staff. Post your service in action. Show behind the scenes. Respond to reviews. Use Instagram’s built-in tools.
The worst case scenario? No one sees it.
But if you don’t post, no one sees you at all.
Local Favorite in Safety Harbor
Jenna’s go-to restaurant in Safety Harbor is Nona’s. She loves the consistency, the staff, and the atmosphere. Bonus recommendation: try the smoked wings.
It ties back to her overall philosophy — consistency builds loyalty.
Final Takeaway
Creativity helps you stand out.
Consistency keeps you growing.
And quitting too early is the fastest way to lose momentum.
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