100 books like Tricky Business

By Dave Barry,

Here are 100 books that Tricky Business fans have personally recommended if you like Tricky Business. Shepherd is a community of 11,000+ authors and super readers sharing their favorite books with the world.

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Book cover of Tourist Season

Susie Black Author Of Death by Jelly Beans

From my list on funny men whose stories take place in Florida.

Why am I passionate about this?

I am Susie Black. Before I became an award-winning, humorous, cozy mystery author, I had a successful career as a ladies’ swimwear sales exec. As you can imagine, I spent a lot of time in Florida. I interacted with progressive, traditional, and conservative buyers and sellers from large cities to small towns all over the Sunshine State. My experiences gave me a unique perspective on the social mores and hierarchy of Florida’s diverse, multi-layered, and complicated society. 

Susie's book list on funny men whose stories take place in Florida

Susie Black Why did Susie love this book?

As someone who has lived for several decades in a resort area that relies exclusively on tourists to survive, it was no shock that I was all over Carl Hiaasen’s book like white is to rice. I loved how biting humor could shine a light on the dark side of tourism and the impact it had on the locals.

Hiaasen’s debut book is a fast-paced masterpiece that focuses on protecting the Sunshine State from greedy, corrupt characters. I found myself in the unique role of rooting for Eco-terrorists, trying to scare builders away from further developing South Florida by murdering tourists and snowbirds. 

By Carl Hiaasen,

Why should I read it?

3 authors picked Tourist Season as one of their favorite books, and they share why you should read it.

What is this book about?

Take a trip to exotic South Florida with this dark, funny book that established Carl Hiaasen as one of the top mystery writers in the game.

The first sign of trouble is a Shriner's fez washed up on a Miami beach. The next is a suitcase containing the almost-legless body of the local chamber of commerce president found floating in a canal...

The locals are desperate to keep the murders under wraps and the tourist money flowing. But it will take a reporter-turned–private eye to make sense of a caper that mixes football players, politicians, and one very hungry crocodile…


Book cover of Orange Crush

Susie Black Author Of Death by Jelly Beans

From my list on funny men whose stories take place in Florida.

Why am I passionate about this?

I am Susie Black. Before I became an award-winning, humorous, cozy mystery author, I had a successful career as a ladies’ swimwear sales exec. As you can imagine, I spent a lot of time in Florida. I interacted with progressive, traditional, and conservative buyers and sellers from large cities to small towns all over the Sunshine State. My experiences gave me a unique perspective on the social mores and hierarchy of Florida’s diverse, multi-layered, and complicated society. 

Susie's book list on funny men whose stories take place in Florida

Susie Black Why did Susie love this book?

Since I was ten, my parents insisted I watch every major party-political convention. So, it was no surprise that now as an adult political junkie, I devoured every page of this book. I loved the what-ifs the book translated to in today’s political picture.

I marveled at how author Dorsey deftly took the unquestioning tool of the powerful special interests incumbent Florida Governor and transformed him into a candidate with a conscience three weeks before the next election. I gave a standing ovation to Dorsey, who used zippy dialog and a fast-paced plot to hysterically make mincemeat of the hypocritical, holier-than-thou morals of an alley cat displayed by state party officials. 

By Tim Dorsey,

Why should I read it?

1 author picked Orange Crush as one of their favorite books, and they share why you should read it.

What is this book about?

If you like your humour dark and twisty, then you'll love Tim Dorsey's outrageous Serge Storms series of crime novels. The Republicans' "golden boy" and a loyal, unquestioning tool of the powerful special interests handsome, unthreatening, Florida governor-by-default Marlon Conrad seems a virtual shoo-in for re-election. That is, until he undergoes a radical personality shift during a bloody military action in the Balkans. Now it's just three weeks before the election and Marlon is suddenly talking about "issues" and "reform" as he crosses the length and breadth of his home state with an amnesiac speechwriter and a chief of staff…


Book cover of Florida Straits

Susie Black Author Of Death by Jelly Beans

From my list on funny men whose stories take place in Florida.

Why am I passionate about this?

I am Susie Black. Before I became an award-winning, humorous, cozy mystery author, I had a successful career as a ladies’ swimwear sales exec. As you can imagine, I spent a lot of time in Florida. I interacted with progressive, traditional, and conservative buyers and sellers from large cities to small towns all over the Sunshine State. My experiences gave me a unique perspective on the social mores and hierarchy of Florida’s diverse, multi-layered, and complicated society. 

Susie's book list on funny men whose stories take place in Florida

Susie Black Why did Susie love this book?

I’ve always marched to the beat of my own drum, so naturally, a fish-out-of-water coming-of-age laugh-out-loud comedy replete with a zany cast, spot-on dialog, and an unlikely hero had me from page one.

People go to Key West for different reasons…magnificent sunsets, key lime pie, to commune with the ghost of Hemingway…The unlikely hero of this cleverly plotted book went to Key West to become a gangster. I led the cheers and gave him a zillion attaboys for standing up for himself and not allowing anyone to rain on his parade. 

By Laurence Shames,

Why should I read it?

1 author picked Florida Straits as one of their favorite books, and they share why you should read it.

What is this book about?

"People go to Key West for lots of different reasons. Joey Goldman went there to become a gangster..." So begins this classic Key West caper, the hilarious and touching book that launched a much-loved series and introduced the world to Bert the Shirt and his chihuahua Don Giovanni, two of the most unforgettable characters in contemporary fiction. Joey, the illegitimate son of a major NY mafioso, decides to break away from a decidedly unpromising future in the old neighborhood of Queens. But will the old neighborhood and the Family let him go in peace? Not if knucklehead half-brother Gino has…


Secret St. Augustine: A Guide to the Weird, Wonderful, and Obscure

By Elizabeth Randall, William Randall,

Book cover of Secret St. Augustine: A Guide to the Weird, Wonderful, and Obscure

Elizabeth Randall Author Of Fire is the Test of Gold

New book alert!

Why am I passionate about this?

Author Reader Baker Teacher Matriarch Adventurer

Elizabeth's 3 favorite reads in 2023

What is my book about?

Tourists and local residents of St. Augustine will enjoy reading about the secret wonders of their ancient city that are right under their noses. Of course, that includes a few stray corpses and ghosts!

Secret St. Augustine: A Guide to the Weird, Wonderful, and Obscure

By Elizabeth Randall, William Randall,

What is this book about?

It is no wonder the ancient city of St. Augustine is steeped in secrets. St. Johns, the oldest continuously occupied county in America celebrated its 450th birthday on September 4, 2015. More like a European enclave than an urban landscape, it is a place of cannon fire, street parties, historical reenactments, concerts, and more. From admiring replicas of fine art at Ripley’s Believe or Not, to hunting haunts in restaurants and museums, to eating ice cream from a recipe originated by World War II bombardiers, St. Augustine has it all from beaches, gourmet dining, festivals, and attractions. A young and…


Book cover of Deep Water

Susie Black Author Of Death by Jelly Beans

From my list on funny men whose stories take place in Florida.

Why am I passionate about this?

I am Susie Black. Before I became an award-winning, humorous, cozy mystery author, I had a successful career as a ladies’ swimwear sales exec. As you can imagine, I spent a lot of time in Florida. I interacted with progressive, traditional, and conservative buyers and sellers from large cities to small towns all over the Sunshine State. My experiences gave me a unique perspective on the social mores and hierarchy of Florida’s diverse, multi-layered, and complicated society. 

Susie's book list on funny men whose stories take place in Florida

Susie Black Why did Susie love this book?

Maybe it’s because, as a woman who worked in a historically male-dominated industry, I always root for the underdog—be it a newbie with the chutzpah to say no to a pushy buyer or a small town fighting off a huge conglomerate. Give me a character who is a caricature of an amusement park scion, dialog dripping with sarcasm, and a zany plot that spits in the eye of corporate America.

I led the applause as S. V. Date gleefully poked fun at the greediness of big business while indicting a state government that, for a price, was more than happy to go along for the ride.

By S.V. Date,

Why should I read it?

1 author picked Deep Water as one of their favorite books, and they share why you should read it.

What is this book about?

A witty satire of planned communities introduces readers to Serenity, Florida--the lifelong dream of amusement park scion Waldo Whipple--a town on the verge of a very public nervous breakdown. 10,000 first printing.


Book cover of Fast Company: How Six Master Gamblers Defy the Odds - and Always Win

Arnold Snyder Author Of Radical Blackjack

From my list on those contemplating gambling as a profession.

Why am I passionate about this?

I was a mailman when I became obsessed with card counting at blackjack. Not having enough money to play at a pro level, I decided to sell a mathematical formula I’d devised for evaluating games and systems. I offered it for sale through gambling newsletters at $100. I immediately had big sales because no one had ever seen a method for estimating card counters’ win rates. I got letters from college math professors asking me how I’d come up with the math. So, I started my own blackjack newsletter where I published my discoveries. I was inducted into the Blackjack Hall of Fame in 2002 and soon had big investors funding my play.

Arnold's book list on those contemplating gambling as a profession

Arnold Snyder Why did Arnold love this book?

Really fun true stories about six gambling legends. Titanic Thompson never entered an official PGA event, yet made more money playing golf than most of the top pros in his era, often by beating the famous pros at their own game. Minnesota Fats never won a major pool tournament, but made so much money traveling from city to city to hustle the local pool sharks he became a legend in the Midwest pool halls. Johnny Moss cut his gambling teeth in illegal poker games in Texas and Oklahoma, then went on to win the first two World Series of Poker championships in 1970 and 1971, winning nine WSOP bracelets in total, his last one in 1988 at the age of 81, making him the oldest WSOP bracelet winner ever.

By Jon Bradshaw,

Why should I read it?

1 author picked Fast Company as one of their favorite books, and they share why you should read it.

What is this book about?

In this classic book, Jon Bradshaw singled out from the world of full-time gamblers six men who consistently win - the men who year after year, deal after deal and proposition after proposition come away with their pockets filled and their sense of infallibility intact.

Bradshaw follows three legendary poker players - Johnny Moss, Pug Pearson, and Titanic Thompson; tennis player Bobby Riggs; pool player Minnesota Fats and backgammon player Tim Holland. His evocation of ambience and his dramatic description of the games themselves are fascinating but Bradshaw also deftly probes their minds and hearts as he attempts to define…


Book cover of Fortune's Formula: The Untold Story of the Scientific Betting System That Beat the Casinos and Wall Street

Barbara Rockefeller Author Of Technical Analysis For Dummies

From my list on for traders using technical analysis.

Why am I passionate about this?

Economics isn't really a good starting point for financial market analysis for the simple reason that its models are wildly inaccurate. As behaviorial economists like Daniel Kahneman have been showing, irrationality and the inability to measure risk properly are a very big component of the investment and trading decisions. But statistical risk management is also sloppy when applied to human behavior because people are not objects that reliably behave the same way under similar circumstances. So when you read an economist about markets or an engineer about risk management, you're missing a lot of the story. In the end, technical analysis is fascinating because how and why humans behave is an enduring mystery.

Barbara's book list on for traders using technical analysis

Barbara Rockefeller Why did Barbara love this book?

The subtitle is The Untold Story of the Scientific Betting System that Beat the Casinos and Wall Street. This book is an easy-to-read narrative of the intersection of the grimy underbelly of betting--with high-minded math. It reminds you that trading is not conducted in a clean little bubble. Technical analysis can give you an edge, but trading is still engaging in battle with opposing forces; strategy and tactics can count as much as building an elegant technical system. 

Your opponent on the trading battlefield will try to trick you, like a general in real warfare. He may keep selling and selling after you have bought, triggering a sell signal in your trading system. He is hunting for your sell signal. The mechanical response is to sell—your system says sell, and you should follow your system. To exit a position when the market goes against you is named a stop,…

By William Poundstone,

Why should I read it?

1 author picked Fortune's Formula as one of their favorite books, and they share why you should read it.

What is this book about?

In 1956, two Bell Labs scientists discovered the scientific formula for getting rich. One was mathematician Claude Shannon, neurotic father of our digital age, whose genius is ranked with Einstein's. The other was John L. Kelly Jr., a Texas-born, gun-toting physicist. Together they applied the science of information theory—the basis of computers and the Internet—to the problem of making as much money as possible, as fast as possible.

Shannon and MIT mathematician Edward O. Thorp took the "Kelly formula" to Las Vegas. It worked. They realized that there was even more money to be made in the stock market. Thorp…


Book cover of Lay the Favorite: A Story About Gamblers

Cara Bertoia Author Of Casino Queen

From my list on true stories set in the casino industry.

Why am I passionate about this?

Growing up in a strait-laced Southern family, I was always fascinated with casinos. In my twenties on a summer hiatus from teaching in North Carolina, I drove to California and became a dealer at Caesars in Lake Tahoe. My mother highly disapproved of my working in a casino, "a place so bad it has 'sin' in the middle." Eventually, I returned east to take a hi-tech job in Boston. I also began working on my MFA in writing at Emerson. My characters were breathed into life from my years in the gambling industry. You learn a lot about the human personality when you watch thousands of people from behind the felt of a blackjack table.

Cara's book list on true stories set in the casino industry

Cara Bertoia Why did Cara love this book?

How does a girl go from working in a Thai restaurant to running a sports gambling operation in Costa Rica? All roads lead through Las Vegas, where Beth meets Dink a math genius. Sports bettors love to hang out in casinos it’s like a contact high. He hires her and she trains in the Vegas casinos. She not only becomes enthralled with the eccentric Dink and the colorful cast of characters that surround him but she shares their stories with you. It was the early days of Internet gambling, a free for all or so they thought. It is great to view the industry through the observant eyes of Beth whose colorful descriptions bring the characters to life. 

By Beth Raymer,

Why should I read it?

1 author picked Lay the Favorite as one of their favorite books, and they share why you should read it.

What is this book about?

“Beth Raymer’s crackling, hilarious memoir ricochets through the gambling underworld in Las Vegas, and is peopled with all manner of lovable wack-jobs, none of whom is quite as wacky—or lovable—as Raymer herself.”—Marie Claire
 
Beth Raymer waited tables at a dive in Las Vegas until a customer sent her to see Dink, of Dink Inc., one of the town’s biggest professional sports gamblers. Dink needed a right-hand man—someone who would show up on time, who had a head for numbers, and who didn’t steal. Beth got the job.
 
Lay the Favorite is the story of Beth’s years in the high-stakes, high-anxiety…


Book cover of No Limit: The Rise and Fall of Bob Stupak and Las Vegas' Stratosphere Tower

Mark Bollman Author Of Basic Gambling Mathematics: The Numbers Behind the Neon

From my list on people who challenged Las Vegas.

Why am I passionate about this?

I’ve been playing card games since childhood, and have had a parallel interest in the mathematics behind the games for nearly as long. While I didn’t visit Las Vegas in person until 2000, the stories of how that city was built around the gaming industry quickly came to fascinate me. Digging into the details of the people who have made that city what it is and have come to make their way in the desert has been a fascinating sidelight that has enhanced my recent work writing books on gambling mathematics.

Mark's book list on people who challenged Las Vegas

Mark Bollman Why did Mark love this book?

No list of Las Vegas entrepreneurs is complete without Bob Stupak, the marketing mastermind who successfully sold many tourists on a visit to Vegas World, a small casino at the far northern end of the Las Vegas Strip. 

The self-described maverick challenged the more established Las Vegas casinos throughout his career, culminating in the building of the Stratosphere Tower which now anchors the Las Vegas skyline. His story mingling success and failure is skillfully told here by a titan of Nevada journalism.

By John L. Smith,

Why should I read it?

1 author picked No Limit as one of their favorite books, and they share why you should read it.

What is this book about?

Of all the modern Las Vegas casino operators, none had more flair than Bob Stupak. The self-proclaimed "Polish Maverick" rose from humble origins as the son of a Pittsburgh boss gambler to head one of the largest privately owned casinos in Las Vegas, the infamous Vegas World. Stupak parlayed a small slot joint into a $100 million-a-year gambling operation by manipulating the local and national media with outrageous stunts and promotions. His headline-grabbing handiwork is now the stuff of Las Vegas legend.

Remember Vegas World's VIP Vacation? Stupak's cleverly worded advertisements flooded millions of mailboxes around the country and appeared…


Book cover of Comp City: A Guide to Free Casino Vacations

Arnold Snyder Author Of Radical Blackjack

From my list on those contemplating gambling as a profession.

Why am I passionate about this?

I was a mailman when I became obsessed with card counting at blackjack. Not having enough money to play at a pro level, I decided to sell a mathematical formula I’d devised for evaluating games and systems. I offered it for sale through gambling newsletters at $100. I immediately had big sales because no one had ever seen a method for estimating card counters’ win rates. I got letters from college math professors asking me how I’d come up with the math. So, I started my own blackjack newsletter where I published my discoveries. I was inducted into the Blackjack Hall of Fame in 2002 and soon had big investors funding my play.

Arnold's book list on those contemplating gambling as a profession

Arnold Snyder Why did Arnold love this book?

The author, a former casino executive, exposes the industry’s “comp system,” through which casinos give away more than a billion dollars in “complimentaries” every year, as an enticement to get people to gamble. Although the book appears to be aimed at amateur gamblers looking for casino freebies (room, food, booze, show tickets, etc.), the information in this book has been devoured by professional gamblers at the highest levels because it reveals the inner workings of how players are evaluated and rated, with tips on how to look like you’re betting more than you are, how to look like you’re losing when you’re winning, and basically how to look dumb when you’re smart. I personally made a lot of money from the information in this book.

By Max Rubin,

Why should I read it?

1 author picked Comp City as one of their favorite books, and they share why you should read it.

What is this book about?

Win every time you gamble? Is that possible? It is if you play for comps.

Every year, U.S. casinos give away more than a billion dollars worth of amenities to customers in return for their gambling action. These giveaways, known as “comps” (short for complimentaries), range from parking and drinks to gourmet meals and airfare. Are you getting your share? From nickel slot players to $500 a hand blackjack high rollers, Comp City has shown tens of thousands of gamblers how to get free casino vacations.

Since the first publication of Comp City, author Max Rubin has been teaching gamblers…


Book cover of Grandissimo: The First Emperor of Las Vegas: How Jay Sarno Won a Casino Empire, Lost It, and Inspired Modern Las Vegas

Mark Bollman Author Of Basic Gambling Mathematics: The Numbers Behind the Neon

From my list on people who challenged Las Vegas.

Why am I passionate about this?

I’ve been playing card games since childhood, and have had a parallel interest in the mathematics behind the games for nearly as long. While I didn’t visit Las Vegas in person until 2000, the stories of how that city was built around the gaming industry quickly came to fascinate me. Digging into the details of the people who have made that city what it is and have come to make their way in the desert has been a fascinating sidelight that has enhanced my recent work writing books on gambling mathematics.

Mark's book list on people who challenged Las Vegas

Mark Bollman Why did Mark love this book?

Grandissimo is a biography of Jay Sarno, the entrepreneur who built Caesars Palace and Circus Circus on the Las Vegas Strip and then lost his empire. 

It is fascinating to see read about how Caesars Palace started with humble beginnings before rising to its current prominent place of the Strip. The book’s title is taken from Sarno’s last great obsession: a new Las Vegas mega-resort that was never built, and the story of how that project never happened is just as interesting as the tales of how the other casino resorts succeeded.

By David G Schwartz,

Why should I read it?

1 author picked Grandissimo as one of their favorite books, and they share why you should read it.

What is this book about?

Jay Sarno built two path-breaking Las Vegas casinos, Caesars Palace (1966) and Circus Circus (1968), and planned but did not build a third, the Grandissimo, which would have started the mega-resort era a decade before Steve Wynn built The Mirage. As mobsters and accountants battled for the soul of the last American frontier town, Las Vegas had endless possibilities—if you didn’t mind high stakes and stiff odds. Sarno invented the modern Las Vegas casino, but he was part of a dying breed—a back-pocket entrepreneur who’d parlayed a jones for action and a few Teamster loans into a life as a…


5 book lists we think you will like!

Interested in gambling, maritime, and Florida?

Gambling 41 books
Maritime 24 books
Florida 139 books