From a Rainy Weekend to 25 Tropical Crime Adventures: My Conversation with Author Chip Bell

Some stories begin with a carefully mapped-out plan.

Others begin with a rainy weekend, a Jimmy Buffett song, a trial attorney with an idea, and the bold assumption that writing a book should only take a couple of days.

That second version is much more fun.

I recently had the chance to sit down with Charles “Chip” Bell, author of the Jake Sullivan series and the man behind our August Fun in Key West Book Club pick, Come Monday.

And let me tell you, this conversation wandered through all the best neighborhoods.

We talked about Key West bars, Jimmy Buffett, tropical crime, courtroom storytelling, Trop Rock music, movie dreams, beer, rum, pierogies, pepperoni rolls, and how one book somehow turned into 25.

Basically, it was part author interview, part island escape, and part regional food dispute.

Exactly my kind of conversation.

It All Started with Jimmy Buffett

Before Chip wrote Come Monday, before Jake Sullivan had a name, and long before there were 25 books in the series, there was a trip to the British Virgin Islands.

Chip was sitting near the Soggy Dollar Bar on Jost Van Dyke when he spotted someone down the beach.

He told his friend Mike, “That’s Jimmy Buffett.”

Mike disagreed.

Chip went to investigate.

It was Jimmy Buffett.

Honestly, this already sounds like the beginning of a good book.

Chip eventually had the chance to say hello and told Buffett how much he enjoyed not only the music, but the stories inside the songs.

Buffett’s response stayed with him:

Stories come from living.

That idea followed Chip home.

Then, on a cold and rainy weekend in 2010, he decided to write a book.

He called it Come Monday, partly because he planned to begin the story on Friday and wrap it up by Monday.

Which is optimistic in a way I deeply respect.

I have opened a document on Friday and still been adjusting the font on Monday.

Meet Jake Sullivan

Chip knew the world of law, so Jake Sullivan began as an attorney.

But Chip did not want to write a traditional courtroom drama.

Jake may have had a legal background, but the story quickly became about something bigger: justice, loyalty, danger, and the kinds of situations that do not stay neatly inside a courtroom.

Jake’s best friend, Mike, was inspired by Chip’s real-life best friend, also named Mike.

The banter between the two characters came directly from the way Chip and Mike talk to each other in real life.

And apparently, real-life Mike finishes every book with the same review:

“I could have been funnier.”

That is friendship.

Not praise. Not criticism. Just a standing request for better material.

Chip’s usual response is essentially, be happy you made it into the book.

Fair.

From One Book to 25

When Chip wrote Come Monday, he did not know whether there would be a second book.

Then readers liked it.

He liked writing it.

And the idea grew.

Chip realized he could turn Jake Sullivan’s story into a series and connect the books through Jimmy Buffett song titles.

That decision gave the series a shared rhythm without making every book dependent on the one before it.

Each adventure could stand on its own, but they still felt like part of the same tropical universe.

Over time, Jake changed.

Mike changed.

Their families changed.

The stakes became higher.

The stories expanded beyond Key West into the Caribbean, international crime, cartels, political trouble, legends, mysteries, and destinations that gave Chip new territory to explore.

But Key West remained home base.

And honestly, where else would you base a tropical crime series?

Key West already comes with smugglers, eccentrics, old grudges, questionable decisions, colorful bars, complicated history, and enough stories to keep a writer busy for several lifetimes.

Justice and the Law Are Not Always the Same Thing

One of the most interesting parts of our conversation was Chip’s approach to justice.

Jake Sullivan understands the law, but he also understands that the law and justice do not always arrive at the same destination.

Chip explained that Jake and Mike became more concerned with doing what was right than simply following the cleanest legal path.

That does not mean they became comic-book heroes.

Jake does not suddenly put on a cape, leap over a palm tree, and solve international crime before happy hour.

Chip wanted the characters to stay human.

They make decisions based on loyalty, experience, and their belief that people who are being harmed deserve someone willing to stand up for them.

As the series continues, their work evolves.

They become investigators and troubleshooters, operating in situations where the rules may be clear on paper but much murkier in real life.

That tension gives the series some weight beneath the tropical setting.

Yes, there are bars, boats, islands, and danger.

But there are also questions about what people owe one another and how far someone should go to make things right.

Key West Is More Than a Backdrop

Chip did not simply place the books in Key West because palm trees look nice on a cover.

The places matter.

The Chart Room became especially important to him.

So did Schooner Wharf.

These were not just locations he researched from a distance. They were places where he met people, listened to stories, built friendships, and experienced the kind of Key West hospitality that stays with you.

Chip talked about meeting people in the Chart Room who welcomed him, shared stories, and became part of his Key West experience.

Some of those people are now gone, but pieces of the conversations and situations they shared found their way into his books.

Not their names.

Not their exact lives.

But the spirit of the stories.

That is one of the things I love about Key West.

You can walk into a bar planning to stay for one drink and leave three hours later with a new friend, a story about 1978, a rumor involving a boat, and no clear idea how the conversation started.

The island is generous that way.

How Chip Writes His Books

Chip does not sit at a computer and type his books.

He dictates them.

He has spent decades dictating legal work, so speaking the story feels natural to him.

He talks through the scenes, his secretary types them, and then he edits and revises.

That process gives the dialogue a spoken quality, which makes perfect sense when you hear him explain it.

He can hear the rhythm.

He can feel where the excitement rises.

He knows how the characters would actually speak.

And because his real-life friendship with Mike inspired so much of the Jake and Mike relationship, the conversations already have a natural back-and-forth built into them.

This also means Chip has written 25 books by talking them out loud.

Meanwhile, some of us have spent 20 minutes trying to rename a Google Doc.

Research, Legends, and the Perfect Hook

Chip does a tremendous amount of research before he writes.

He looks at maps.

He checks streets.

He studies local legends.

He investigates history.

He makes sure that if a street is one-way, his character is going the right way.

That detail made me happy.

There is always someone reading who knows the exact street, the exact building, and the exact angle of the stop sign.

Key West readers do not play around.

Chip often begins with a destination or a piece of local history that catches his attention.

Then he searches for the hook.

A legend.

A strange person.

A historical mystery.

A forgotten event.

Once he finds that thread, the story begins to take shape.

One example was Montserrat, where his research led him into a story involving the American Revolution, politics, and a Frenchman whose history gave him exactly what he needed for the book Volcano.

Another was his standalone novel Full Moon, Blood Moon, which grew from his discovery of a possible family connection to Sherm McMaster, a real figure from the Tombstone era whose death remains something of a mystery.

That mystery led Chip into deeper research, and then the year 1888 started to reveal more and more connections.

This is how writers get into trouble.

You look up one name.

Three hours later, you have 14 browser tabs open, a historical weather chart, a cemetery map, and a new book.

The Books Grew Into Music

The Jake Sullivan series did not stay confined to books.

Chip connected with Trop Rock musicians including Donnie Brewer, Eric Stone, and John McDonald.

That led to songs inspired by the series and eventually a full concept album called Everything’s Jake.

The title has its own strange historical backstory involving Prohibition-era alcohol and a substance nicknamed “Jake.”

Which is exactly the kind of unexpected rabbit hole this conversation kept finding.

Chip freely admitted that he cannot carry a tune.

His daughters apparently encourage him not to test that theory in public.

But that did not stop him from becoming part of the creative process.

He contributed ideas, storylines, and some lyrics, while the musicians turned Jake Sullivan’s world into music.

I spent time listening to the songs before the interview, and they do exactly what the books are meant to do.

They transport you.

Suddenly you are somewhere warmer, the beer is colder, the barstool is open, and there is probably a boat nearby that belongs to someone with a complicated past.

There Was Beer

At one point, the Jake Sullivan universe also included a Caribbean lager.

Chip connected with a brewery near Pittsburgh that had built its brand around a Caribbean feel.

Together, they created the Jake Sullivan Caribbean Lager.

It became one of the brewery’s most popular beers while it was available.

The brewery itself sounded amazing, with sand incorporated into the flooring and a full tropical atmosphere.

Naturally, this gave me ideas for our tiki bar at home.

My son is a contractor.

I am sure he will be thrilled when I casually mention pouring sand across the basement floor and covering it in clear epoxy.

Nothing says relaxing family conversation like, “I saw this in a brewery and now I have a project for you.”

There Was Almost Rum

A Jake Sullivan rum was also considered.

A few bottles were even created.

Then everyone encountered the maze of alcohol regulations.

And the rum adventure came to a halt.

Alcohol laws can turn a fun tropical idea into a filing cabinet wearing a necktie.

The licensing, production, distribution, state rules, and interstate rules became more complicated than Chip wanted to manage.

So the rum remained more of a limited curiosity than a full product.

Probably wise.

But I still enjoy knowing that somewhere in the story of Jake Sullivan, there was a moment when someone held up a bottle and said, “We made rum.”

Hollywood Came Calling. Sort Of.

Chip also has a movie script and a television pilot connected to the series.

He has pursued agents, producers, platforms, and opportunities.

He has received the familiar collection of polite rejections that comes with trying to enter the entertainment industry.

He talked honestly about how difficult the process is and how much competition exists.

Anyone can now write a book, publish it, create a script, and send it into the world.

That creates opportunity.

It also creates one very crowded world.

Still, Chip has his dream casting in mind.

He once imagined Ben Affleck as Jake and Matt Damon as Mike because their real-life friendship could bring the right energy to the roles.

He also mentioned Timothy Olyphant as another possible Jake.

Honestly, I can see it.

Tall, calm, slightly dangerous, capable of delivering a line that makes you wonder whether you should laugh or leave the room.

The Most Important Debate: Pierogi or Pepperoni Roll?

Because Chip is from Western Pennsylvania and I am from West Virginia, we had to settle a major regional question.

Pierogi or pepperoni roll?

Chip chose the pierogi.

Specifically, fried pierogies with cheese, onions, and even more onions.

A respectable answer.

Wrong, obviously, but respectable.

And yes, I know pepperoni rolls come with their own debate.

Sticks or slices?

Cheese or no cheese?

That argument could probably fill an entire podcast episode.

We moved on before anyone needed legal representation.

Chip’s Key West Favorites

Toward the end of our conversation, we moved into rapid-fire Key West questions.

For breakfast, Chip chose Pepe’s.

His order is simple: eggs, sausage, hash browns, and toast.

He does not drink coffee.

His morning drink is Diet Coke.

This may be the most controversial revelation in the entire interview.

No coffee.

No tea.

No hot chocolate.

He likes drinks cold.

At the bar, he prefers beer, especially Corona with no lime.

And when I say no lime, I mean he has opinions about the lime.

Chip’s favorite Key West moments include sitting near the Chart Room, enjoying the Pier House, and listening to music at Schooner Wharf.

He likes sitting at the bar rather than at a table.

Same.

The best stories happen at the bar.

You meet people.

You overhear things.

You start talking.

You learn where someone is from, how they ended up in Key West, why they are never going back, and who they once saw riding a bicycle down Duval Street wearing something that cannot be repeated before breakfast.

Tables are fine.

Barstools have better material.

What Comes Next?

Chip is considering retirement from his law practice after nearly 50 years.

He is also looking forward to spending more time with his family and grandchildren.

As for more Jake Sullivan books, he is not making any promises.

He may get the itch again.

He may discover another historical mystery.

He may find one strange detail that refuses to leave him alone.

That is the danger of being a storyteller.

You think you are finished.

Then someone tells you about a missing grave, an old ship, a long-forgotten bartender, or a suspicious event from 1888.

And suddenly, you are writing again.

My Favorite Takeaway from the Conversation

What stayed with me most was not simply that Chip wrote 25 books.

It was how one thing kept leading to another.

A friendship led to a character.

A Jimmy Buffett song led to a title.

A rainy weekend led to a book.

A book led to a series.

The series led to music.

The music led to friendships.

The friendships led to travel, events, beer, scripts, and stories Chip never could have predicted when he began.

That is the part I keep thinking about.

We often believe we need to see the full path before we start.

But most good stories do not work that way.

You begin with the piece you have.

One idea.

One conversation.

One page.

One trip.

One rainy weekend.

Then you see where it goes.

Ready to Meet Jake Sullivan?

After hearing Chip’s story, I have a feeling you may want to spend a little more time with Jake, Mike, and the wonderfully complicated world they inhabit.

Start with Come Monday, the book that launched the entire adventure:

https://amzn.to/4z5T9Km

Already planning to settle in for all 25 tropical crime adventures?

Explore the complete Jake Sullivan series:

https://amzn.to/4fK0WEs

A quick island-sized disclosure: As an Amazon Associate, I earn from qualifying purchases. The book links above are affiliate links, which means I may earn a small commission if you make a purchase, at no additional cost to you. Your support helps keep the books open, the microphones on, and the Key West stories coming. 🌴📚

Learn More About Chip Bell

Visit Chip Bell’s website to explore his books, learn more about the Jake Sullivan series, and see what else he has been creating:

http://www.chipbellauthor.com/

Turn Up the Trop Rock

The Jake Sullivan adventures did not stop with the books. Chip’s stories also inspired music from some incredibly talented Trop Rock artists.

Give them a listen, and do not blame me if you suddenly find yourself pricing flights to Key West.

John McDonald on Spotify:
https://open.spotify.com/artist/5sG9ecAhtnZuFMcrZJK3Bc?si=ZwOeSYz6SL2LVwd3FHg0uw

Donnie Brewer on Spotify:
https://open.spotify.com/artist/4nI1bYqONqWFnHPlSL9k35?si=2quwmqoxSMapg6nyProtJg

Eric Stone on Spotify:
https://open.spotify.com/artist/09w2nmrWDRCL0wtRqoNLdM?si=zGmXUy0HRxyBTw68IfIZjA

Discover the True-Crime Side of Key West

This conversation was sponsored by the iWitness Key West True Crime Tour.

Key West may look like sunshine, cocktails, colorful houses, and postcard-perfect streets, but those same streets have witnessed real scandals, smugglers, gamblers, crimes, and characters behaving very badly.

This is not a ghost tour. These are real stories connected to real people and real places, shared as you walk through the streets where they unfolded.

Learn more or book your tour:

https://funinkeywest.com/crime