The Power Of Dedication (And A Little Magic) Leverage Yourself, Your Partners, And Your Practice With Penn Jillette’s Secrets To Success

When Penn Jillette was kicked off the stage after showering late-night television show host David Letterman and his desk in cockroaches on national television in the 1980s, Penn’s first thought was of his mother. 

Leading up to the now-legendary performance, Penn called his mom to clue her in on the trick he and his partner, Teller, planned to perform for Letterman’s audience. It was a trick that was months in the making — a trick Letterman had practically asked for. After their first “Late Night” performance months earlier, Letterman encouraged the then-rising illusionist duo, known as Penn & Teller, to give him all they had next time. He wanted the audience to sympathize with him and really feel his astonishment in the misdirection.  

So, Teller proposed a now-famous idea to Penn: “We could dump half a million cockroaches on him.”

The duo spent weeks practicing their moves and finding materials that cockroaches wouldn’t cling to. They worked with researchers, familiarized themselves with the bugs, covered their arms and legs in cockroaches, and found the best species for their bit. They rehearsed tirelessly and secretly for weeks before pitching it to “Late Night” producer Robert Morton. The producer was hesitant because of Letterman’s phobia of bugs, but Letterman, who had no idea what the scheme was, persuaded Morton to let Penn & Teller do whatever they wanted. 

Penn’s mom warned her son otherwise. 

“She said, ‘You’ll never work in show business again,’” Penn remembers of their conversation. “‘You can’t drop bugs on a person at their own show!’”

But they did, and the result was a maddening reaction from Letterman and a legendary trick that fans and viewers still remember. Letterman had no clue what was going to happen and was every bit as angry as he appeared to be on television, even when the cameras stopped rolling. 

“We broke for a commercial break, and I went to shake Dave’s hand, as is customary,” Penn recalls, “and he said, ‘Get the f— away from me!’ I thought, ‘Oh, geez, Mom was right.’”  

Penn & Teller left the studio without knowing their fate. At the time, they had been performing together for less than a decade after partnering in the late ‘70s and were still climbing the ranks as household names. They hadn’t yet secured the prime spot on late-night TV, and the Letterman slot had been their stepping stone, albeit a stone they had just dumped an entire top hat of bugs onto. 

The next day, they got their answer. 

“Dave called up and said, ‘Penn, I watched the cockroach segment last night. It’s the best bit we’ve ever had on the show. You can do whatever you want on the show. Goodbye,’” Penn shares. “I still don’t think that I have the focus on what I do to overcome my fear of the unknown, but Dave was able to do that.” 

Penn may give most of the credit for the bit’s success and popularity to Letterman, but it was the ingenuity, practice, and dedication he and Teller are known for that led them to the Letterman stage and propelled their careers to the status they have today. They continue to maintain that unique and dynamic business relationship that catapulted them into success. Today, Penn & Teller claim the title as the longest-running show in Las Vegas history and continue to make us all believe in a little magic. 

Robin Robins recently sat down with Penn to discuss the value of dedication, his everlasting partnership with Teller, and the ingenuity of his “brand” in front of an audience of exclusive members of her Tennessee-based marketing company, Technology Marketing Toolkit. With Penn’s tools for success, any MSP leader or business owner can tap into their own powerful potential. All it takes is a little commitment and honesty (no magic required!). 

The Value Of A Thousand

Before he was selling out shows in Las Vegas and creating a worldwide following, Penn claims that the first person he ever met in show business was himself. He grew up in small-town Massachusetts, far-flung from the stage and tricks by sleight of hand. The thought of performing was, as Penn explains, “an impossibility.” But as a teenager, Penn saw a performance by illusionist James Randi, who proclaims his tricks are merely that: just illusions, not magic. 

Penn became obsessed with creating illusions and entertaining an audience with misdirection. He committed himself to mastering the craft through consistent practice, education, and adjustment. In the late 1970s, he was introduced to Teller — whose legal name at the time was Raymond Joseph Teller — and the duo eventually formed Penn & Teller. 

For more than 40 years, they’ve been performing around the globe, and they still like to delight fans with tricks they’ve done for almost half a century. Today, Penn & Teller perform each week in various cities. Their shows run from Saturday to Wednesday at the Rio in Las Vegas, and they hit the road on Thursdays and Fridays for multiple touring shows. However, they don’t rely on previous success to get by. Penn is continuously practicing, and he and Teller are constantly brainstorming new ideas for their act, never growing bored of it. 

“All I ever wanted was to put shows together and have people want to see them,” Penn says. “Now, I’m 64 years old, and I have that. And I want it more than I did when I was 16.” 

The only magic in the secret to their success is a powerful formula of connectivity as partners and dedication to their craft. The latter is a belief Penn adheres to diligently. 

Penn will practice, refine, and tweak his tricks thousands of times, at the very least. To him, the development of a craft isn’t something that happens overnight. You can’t pick up a deck of cards and expect to “wow” an audience with your first trick. Likewise, you can’t launch your business with the first idea you brainstorm and expect it to be the billion-dollar idea that rockets you into success. You can’t even dump a top hat full of cockroaches on Letterman’s desk without rehearsing the trick for months on end. 

“I believe there is something you get from doing something thousands of times that you can’t get any other way,” Penn says. 

Because of his skill and composure with the craft, there are times when his body goes into autopilot mode. He doesn’t know what he’s saying, but his body remembers what to do. His partner, Teller, also knows what the next move will be. Without actively engaging, Penn knows what to anticipate and how to get the end result audiences rave about. 

“I know when I’m going to touch my nose. I know when I’m going to swallow. I know when I’m going to touch my forehead. I know every breath that I’m going to take for that six minutes,” Penn says. “The very thing that you would think gets boring and gets robotic actually becomes unique and beautiful and mindful in that moment because everything is moved into autopilot.”

But the only way to find that mastery is to keep practicing. Mastering a craft boils down to dedication and perception. It’s about finding the place where you can anticipate problems and engineering your business to respond in the exact way you would expect it to when you need it to. 

To get to that automatic state takes constant practice and adjusting the techniques — possibly thousands of times — to predict the needs your clients may not even know they have. It takes repetitions, mistakes, and adjustments to push an MSP to the point of beautiful automatic success. 

The Power Of Partnership

Penn couldn’t reach autopilot in this act alone. After all, he is Penn of Penn & Teller. After years of mastering his craft, he’s a clear professional, but his career has been far better with Teller, even if it’s purely business. 

“Most partnerships, especially in show business, are romances. Those all end in a great deal of sadness because when love goes away, there’s disillusionment to that. It’s really ugly,” Penn says. “Teller and I had no clicking whatsoever, but we felt that we did better stuff together than we did separately. It was a cold business decision, and it was a love of the art and a love of the show. So, when Teller and I didn’t get along, it was no surprise. We didn’t expect to.” 

Despite how their relationship changed and conflicts arose within it, a powerful connection built on mutual respect and courtesy propelled them forward. The duo coordinates together more like business partners than best friends. They spend upward of eight hours every day performing together and quite literally put their lives in the hands of one another. 

Penn believes Teller is the “best magical mind in the world today.” Teller coordinates the visuals and picks up on the little, key actions that make their acts powerful and mysterious. In a simplified sense, Penn writes the act, Teller directs the bits, and they come together in complete partnership and understanding. 

The bond between the pair has created an air of mutual honesty and dedication to their craft that allows them to show up for one another as business partners. They do what the other expects of them, and when tensions flare up, they have learned to let the anger and frustrations hang there before moving on. 

After spending more than 40 years together traveling the globe, picking up new projects, and perfecting new acts, the duo has found a way to blend their original apathy with respect and friendship in a beautiful state of business partnership. 

“Now, after 45 years of it, it’s disingenuous to not admit to friendship,” Penn said. “When our parents have died, when we got health diagnoses, through marriage, when kids were born — when my mom died, he was the first one I talked to. But we are cordial, and we are separate.” 

It’s not the friendship that fuels success, Penn explains. It’s finding a dynamic that’s going to propel a business forward and best serve the needs of customers. Eventually, that support and friendship will fall into place, and a natural order to the relationship will form. But in order to survive and provide powerful results for clients, your business relationship has to be nurtured first. 

“But he is perfect,” Penn explains of Teller. “He’s always on time. He does what he says he’s going to do. He doesn’t make mistakes. It’s an ongoing partnership.” 

When Your ‘Brand’ Is Just You

After every performance, Penn & Teller talk with any audience members who want to meet with them or ask questions. They engage with their audiences for as long as necessary, signing items and sticking around until the final fan has taken their last photo. In fact, when the duo plays the Eventim Apollo, formerly the Hammersmith Apollo, in London, due to local ordinances and crew union regulations, their entire crew and the staff of the Eventim Apollo leave long before Penn & Teller are done signing autographs and talking to fans. The lights come down on the theater, and every employee goes home. Yet, Penn & Teller continue meeting with fans. 

It’s been called a genius marketing tactic — a ploy that brands the duo as genuine and authentic to sell tickets and get the “average Joes” to come to the show. Penn admits that while it’s flattering that people have found skill in their madness, it’s not why they do it. In reality, it’s a practice that was born out of necessity and habit. 

Other performers have tried mimicking them by opening their back doors to audiences and eager fans for a meet and greet, but after a few weeks of doing so, they often quit. Penn explains that it becomes too much for most people, and many of them dread the facade they have to continue after the show and the exhaustion that comes with it. 

Penn & Teller Just Enjoy Doing It 

“We’ve always done that over our career, and it was never done because [we said], ‘Boy, if we meet anybody personally, we’ll be more successful,’” Penn shares. “It was done because when we were carny trash, we had no place else to be.

“You can get more meta and say it’s the authenticity and the audience reactions, and therefore, they like more, and therefore, it’s better branding,” Penn continues, “but at some point, you’ve got to say it’s because you like doing it.” 

Penn has never been one to let critics’ opinions influence his thoughts or performances. Beyond the investment reports and the important feedback that has kept the show running for the past 40 years, Penn won’t read anything with his name in it. That criticism and overview is not for him. It’s not material that will benefit him; instead, it’s intended for the reader and audience. 

Together, Penn & Teller have developed their own unique style to magic. A quiet Teller is always ready with misdirection, while the fast, loud, and clever antics of Penn pull viewers’ attention to the stage. What goes on backstage and in their preparation is something only they know. 

Despite their act, what they present off of the stage has little to do with misdirection. “Branding” isn’t a word in Penn’s arsenal. It’s not an accurate explanation for the work he and Teller put into their shows and the dedication they show their excited fans. 

Yet, Penn knows there will always be something to criticize. No matter how streamlined or advanced your practices are, someone will find the weak link in the chain you have created. They will always have criticism for what you have done, and in most instances, those views are correct, according to Penn. But that’s not the feedback you should listen to. 

“If you come up to me after a show, and you say, ‘Do you want to know honestly what I thought of your show?’ My answer is, ‘I already know,’” Penn says. “If you’re in the audience, and there are 1,400 people there, you get 1/1,400 of the vote on every applause, every laugh, everything. I’ve gotten your vote. What you’re trying to do is pack the ballot box, and I will not allow that.”

The only voices that matter are the ones that directly influence the success of your business: your customers and the team you trust to help those customers. Once you block the critics, the naysayers, and those who offer you no real value, you will find the power and value of the voice, the work, and the relationships you put into the business you’re building. 

After all, perfecting your craft and listening for the applause is far more beneficial.

MSP Success Magazine is a print and digital publication dedicated to helping the CEOs and owners of managed IT services businesses build strong, profitable, growth-oriented businesses. Written and published by Robin Robins, founder of Technology Marketing Toolkit, this magazine is uniquely focused on the topics of marketing, client-acquisition, sales, profitability, leadership and personal development.



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