Episode 65: How Estate Cigars & Social Is Building Community Through Cigar Culture in St. Pete | Jonathon Waterman
For Jonathon Waterman, cigars were never just about smoking.
They were about sitting down, slowing down, talking to people, and creating the kind of conversations that might never happen anywhere else.
That idea eventually became Estate Cigars & Social, a cigar lounge Jonathon built in St. Pete with community at the center of the experience.
In Episode 65 of Talkin’ St. Pete, Ryan Bogden sits down with Jonathon to talk about his unexpected path from the music industry to entrepreneurship, the craftsmanship behind premium cigars, building a business during COVID, and why he believes St. Pete's south side has more potential than people realize.
It Started With One Cigar at 18
Jonathon's interest in cigars started after his high school graduation.
A friend brought cigars to celebrate, Jonathon tried one, and the experience immediately caught his attention.
The next day, he walked into a local cigar lounge knowing almost nothing and asked for help.
He kept going back.
Jonathon and his friends were much younger than most of the regulars, but once people realized they were genuinely interested, they started teaching them.
What began as curiosity turned into a hobby that stayed with Jonathon through every stage of his life.
But opening his own cigar lounge wasn't part of the plan yet.
Before Cigars Became a Business, There Was Music
Around the same time Jonathon discovered cigars, he was also pursuing music.
He started writing songs and performing while in college, eventually building a large social media following and recording music in Los Angeles.
One of his projects reached No. 10 on the iTunes singer songwriter chart at the time, and opportunities eventually brought him to Nashville.
He spent about six years pursuing music there.
It wasn't the glamorous version of the industry people sometimes imagine. Jonathon describes working side jobs, playing shows, traveling, and continuing to chase the opportunity while trying to make a living.
Eventually, he knew he wanted something different.
He had friends in St. Pete who were business owners, and he saw an opportunity to put himself around people who could help him understand entrepreneurship.
So he moved to St. Pete.
The Idea Came During COVID
Jonathon continued working in the music industry after moving to Florida, but cigars remained part of his life.
Then, during COVID in 2020, he was traveling with a music nonprofit as the industry experimented with drive in concerts.
During one of those trips, the thought finally became real:
What if he opened his own cigar lounge?
Jonathon had spent years visiting cigar lounges and knew what he liked and what he didn't.
More importantly, he didn't see the type of cigar lounge he imagined anywhere in St. Pete.
He had a business plan created in early 2021 and started figuring out whether the idea could actually work.
That was only the beginning.
Getting the Doors Open Took Almost Two Years
Jonathon didn't have all the money needed to open the lounge himself, so financing became one of the first major hurdles.
He eventually pursued an SBA loan and talked with several banks.
Some liked his business plan but didn't like his location.
Jonathon refused to give up on it.
He believed in the area and was willing to wait for the right lender.
Then came the buildout.
One of the biggest investments was something customers may barely notice when it is working correctly: ventilation.
Jonathon wanted a cigar lounge where people could enjoy a cigar without sitting in a room filled with lingering smoke.
He says the custom system exchanges the indoor air with outside air roughly every seven minutes.
It took months to get the system built, but the experience mattered more to him than rushing the doors open.
Why “Social” Matters Just as Much as “Cigars”
The name Estate Cigars & Social was intentional.
Jonathon wanted the lounge to feel welcoming whether someone had smoked cigars for 15 years or was trying one for the first time.
He remembers walking into cigar lounges where beginners could feel like they didn't belong.
He wanted the opposite.
If someone walks in knowing nothing about cigars, the goal is to help them find something they can enjoy without making the experience intimidating.
The lounge itself is intimate, which naturally creates conversation.
Someone can walk in alone, ask another person what they're smoking, and suddenly two strangers have something to talk about.
Different careers, backgrounds, ages, and lifestyles can all end up around the same conversation.
That community became one of Jonathon's favorite parts of the business.
There Are Hundreds of Hands Behind One Premium Cigar
Jonathon also gives Ryan a deeper look at why he considers cigars a craft.
According to Jonathon, roughly 300 sets of hands can touch a premium cigar between the seedling and the finished product.
The tobacco is planted, harvested, hung, aged, selected, and eventually rolled by hand.
Some tobacco can age for years before becoming part of a cigar.
Different tobacco origins, wrappers, aging processes, sizes, and blends can completely change the experience.
That's why Jonathon doesn't recommend that a new cigar smoker simply buy the most expensive cigar available.
They may not even recognize the difference yet.
Instead, his advice is to try different cigars, pay attention to what you enjoy, learn about the tobacco, and slowly develop your own preferences.
Why Jonathon Bet on St. Pete’s South Side
Location became one of the biggest parts of the Estate Cigars story.
When Jonathon told people where he planned to open, he often heard skepticism about St. Pete's south side.
He saw something different.
Jonathon felt the area still had an older St. Pete neighborhood feel, with local residents who wanted more restaurants, bars, and independent businesses nearby.
Instead of following everyone else to Central Avenue, he saw an opportunity to become part of an area that still had room to grow.
Estate Cigars & Social opened on 4th Street South near Booker Creek.
Jonathon hopes other entrepreneurs will start looking south too.
He believes there is room for more local restaurants, bars, and businesses to become part of those neighborhoods rather than concentrating everything in the same parts of downtown.
Can St. Pete Grow Without Pricing Out Local Businesses?
Ryan and Jonathon also get into a bigger conversation happening across St. Pete.
As development continues and commercial rents rise, what happens to the independent businesses that helped give the city its personality?
Jonathon isn't against growth.
In fact, he sees much of St. Pete's growth as a good thing.
His concern is what happens if commercial spaces eventually become too expensive for small businesses and only large companies can afford them.
For Jonathon, local businesses are a major part of what makes walking through St. Pete different from visiting a typical suburban commercial district.
The question isn't whether St. Pete should grow.
It's whether local entrepreneurs will still have a place in that growth.
Creating a Place People Want to Come Back To
Estate Cigars & Social was built around Jonathon's passion for cigars, but its success depends on something much simpler.
People.
Within its first year, Jonathon says the lounge won a Best of the Bay award, something he didn't expect so early.
Customers became regulars.
Some regulars eventually became employees.
And the social atmosphere he imagined before opening started becoming real.
For Jonathon, that's the part that matters most.
People can smoke a cigar at home.
They choose to come to a lounge because they want the experience that comes with it.
A good cigar may bring someone through the door.
The people sitting around them can be what makes them stay.
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