Episode 93: Why Cheeky’s Chose St. Pete: Nate Siegel on Hospitality, Oysters, and Building a Restaurant People Want to Come Back To
When Nate Siegel opened Cheeky’s in St. Petersburg, the goal was not to create another high end seafood restaurant.
He wanted a neighborhood spot.
A place where someone could stop in for oysters and a cold drink, grab a grouper sandwich, meet friends for dinner, or stay for another round without feeling like they needed a special occasion.
In Episode 93 of Talkin’ St. Pete, Ryan Bogden sits down with Nate Siegel, founder of Cheeky’s and co founder of Willa’s, to talk about building restaurants, learning hospitality in New York, the differences between Tampa and St. Pete, and what it takes to create a restaurant people actually want to return to.
Nate describes Cheeky’s as a fish and raw bar neighborhood joint.
The focus is simple: fresh seafood, oysters, cold drinks, approachable food, strong service, and an atmosphere that feels comfortable from the moment you walk in.
Why Central Avenue Made Sense
Nate grew up in Tampa, spent years in New York City, and eventually moved back to Tampa Bay.
But St. Pete had always stood out to him.
He sees Central Avenue as one of the strongest stretches of walkable local businesses in the Southeast, with restaurants, bars, galleries, shops, and neighborhoods all connected along the same corridor.
When the opportunity for Cheeky’s came up near the Grand Central District, Nate saw something he liked.
The neighborhood already had momentum, but it still had room to grow.
That is something he looks for when choosing locations.
Instead of waiting until an area is completely built out and expensive, he likes finding places where there is already a strong community but still an opportunity to become part of what is coming next.
Cheeky’s opened on Central Avenue in May, close to Historic Kenwood and surrounded by the kind of independent businesses that give St. Pete its character.
For Nate, that local neighborhood feeling is exactly what the restaurant needed.
From Dishwasher to Restaurant Owner
Nate did not start his hospitality career as an owner.
After college, he moved to New York City and worked in creative fields including design, marketing, and advertising.
Then the 2009 recession changed his direction.
After being laid off, Nate decided to pursue something he had always been interested in: restaurants.
He started as a dishwasher.
From there, he worked his way through different roles and learned from experienced hospitality operators in New York.
That experience gave him a completely different understanding of what it actually takes to run a restaurant.
The food matters, but it is only one part of the business.
There is construction, permitting, branding, insurance, hiring, training, marketing, menu development, purchasing, operations, service, and dozens of details customers never see.
And after all of that work just to open the doors, the real job starts.
You have to execute again the next day.
And the next.
That consistency became one of Nate’s biggest lessons from New York.
Every guest matters.
Every day matters.
And the little details eventually become the big details.
Why Cheeky’s Keeps the Concept Simple
One of Nate’s biggest beliefs about restaurants is that trying to do too much can actually make a business weaker.
Instead of trying to become everything for everyone, he would rather narrow the focus and become really good at a few things.
That philosophy shaped Cheeky’s.
The restaurant centers around fresh fish, oysters, seafood, drinks, and hospitality.
There are other options on the menu, including a burger and salads, but Nate does not want the restaurant constantly chasing every trend or trying to become something it is not.
The same thinking applies to the overall business.
Cheeky’s continues to adjust the small things, from menu items and seating to training and service.
But the core idea stays consistent.
Create the kind of place locals want in their own neighborhood.
Hospitality Is More Than Bringing Food to the Table
One of the strongest parts of Nate and Ryan’s conversation is the difference between service and hospitality.
Service is the transaction.
Someone orders something.
The restaurant delivers it.
The guest pays.
Hospitality is everything people feel around that transaction.
Do they feel welcome?
Do they feel comfortable?
Do they feel rushed?
Do they feel like the restaurant actually wants them there?
Nate shared a story from a dinner at Eleven Madison Park in New York that stuck with him for years.
Before he and his wife even arrived, the restaurant had apparently researched them enough to learn about Nate’s background in hospitality and make a connection to Tampa.
It was a small detail.
But it immediately made the experience feel personal.
Years later, Nate does not remember every dish they ate.
He remembers how the restaurant made them feel.
That same idea shapes how he looks at Cheeky’s.
People may not remember exactly what they spent or every ingredient on their plate.
But they will remember whether they felt taken care of.
Tampa and St. Pete Feel Completely Different
Nate now operates in both Tampa and St. Pete, and one thing has become very clear to him.
The cities may only be separated by a bridge, but the restaurant culture feels different.
St. Pete feels more casual and neighborhood driven.
People walk to restaurants.
They show up from nearby neighborhoods.
They come in from events along Central Avenue.
They spend time moving between local businesses instead of necessarily visiting one destination and immediately leaving.
That fits Cheeky’s.
Nate wants the restaurant to feel like it belongs to the neighborhood.
Not like a Tampa restaurant that simply opened a second location in St. Pete.
He wants locals to feel ownership over it.
That means earning regular customers one visit at a time.
Nate shared that it can take several visits before someone really becomes a regular, which makes those first experiences especially important.
More Great Restaurants Can Be Good for Everyone
Cheeky’s is not the only seafood restaurant in the area.
Nate is completely comfortable with that.
He mentioned nearby businesses like Trophy Fish and other local seafood and oyster concepts, describing the area almost like an emerging Oyster Row.
Instead of seeing every restaurant as direct competition, he sees strength in having more good businesses nearby.
More restaurants give people another reason to visit the neighborhood.
More visitors create more foot traffic.
More foot traffic can help everyone along Central Avenue.
That fits one of the things that has helped define St. Pete’s local business community.
Different businesses can have their own identity while still supporting the larger neighborhood around them.
What Is Next for Nate Siegel?
Cheeky’s is still relatively new, and Nate’s focus remains on strengthening what is already working.
But there are more hospitality projects ahead.
He talked about future work connected to the redevelopment of the Tahesian Inn in Tampa, which is being reimagined as a neighborhood hotel.
He is also involved in a major project near J.C. Newman Cigar Company in Ybor City.
J.C. Newman operates what Nate describes as America’s last hand rolled cigar factory still in operation, producing tens of thousands of cigars each day.
Across from the factory, an historic building is being redeveloped with hotel rooms, a restaurant, and a cigar club while keeping the history of the neighborhood at the center of the concept.
Nate also shared that he would eventually like to bring Cheeky’s to Tampa.
But there is no rush.
The goal is not simply to open more restaurants.
It is to open the right restaurant, in the right neighborhood, with the right team.
Creating a Restaurant People Want to Belong To
Cheeky’s may be built around oysters, fresh fish, seafood, and drinks, but Nate’s bigger goal is about something more human.
Belonging.
A restaurant becomes special when people stop thinking of it as somewhere they tried once and start thinking of it as their place.
Somewhere they know the staff.
Somewhere they bring friends.
Somewhere they feel comfortable stopping in without planning weeks ahead.
That is the kind of restaurant Nate wants Cheeky’s to become in St. Pete.
And in a city where local restaurants and independent businesses are such a big part of the culture, that approach fits right in.
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