What Funny Money: The Dane Cook Story Reminded Me About My Relationship with Money
By: Michael Mazzara
Today, I’m guest-authoring Katy’s blogpost.
This week I find myself reflecting on the documentary, Funny Money: The Dane Cook Story, which holds 98% rating on Rotten Tomatoes. The logline reads: “A gripping documentary about fame, family greed, and survival, revealing an extraordinary true story behind one of comedy’s biggest icons.”
At his peak, Dane Cook was one of the biggest comics in the world. I must admit, I was never a huge Dane Cook fan, but I was curious about his rise to stardom…how he became such a national sensation in the 90’s, 2000’s, and beyond.
I learned that Dane Cook is a self-made man, he had his eye on the prize of being a famous comedian from an early age, and he worked his tail off honing-in on how to attract an audience and find his voice in a sea of competition.
What really impressed me was how he set such a high-reaching goal for himself as a teenager. Dane wanted to become one of the biggest comedians in the world, and he was not turning back, his mind was made-up. It was going to happen. He manifested his success, literally. But it wasn’t all to line just his own pockets. Dane had a clear intention, to make enough money to help his brother and family too.
Dane came from an “upper-lower class” upbringing, as he states in the documentary. He found success working tirelessly at his craft, accomplishing his goals of being nationally known, and amassing a small fortune in the process. The big problem was that he had no grasp on what that fortune even looked like.
Although Dane did not have his eyes on his prize, he did have a clear vision for his path to stardom. One of his life-long goals was to be on Saturday Night Live and when Lorne Michaels offered him a role on the show (to replace Adam Sandler), Dane turned it down. Where almost every comedian in his shoes would have jumped at the chance to grace the stage as a regular at studio 8H, Dane did the opposite. He bet on himself.
He didn’t want to be a guy who got a sketch on SNL in the 11:50 PM timeslot…. then fizzled out a few years later. Dane had bigger aspirations, he wanted to be his own brand, have his own voice, and ultimately be in the driver’s seat of his own career. And make real money.
And that’s exactly what he did.
Dane’s half-brother, Darryl McCauley, became his business manager when Dane was still an up-and-coming comedian in Boston.
Darryl was very influential in Dane’s life, they grew-up as brothers, living under the same roof. They bonded over their sometimes difficult up-bringing with a dad who drank and would get unpredictable. Dane recalled a time when his big brother Darryl took him to see Die Hard, to escape the chaos of their home-life. It was moments like this as kids that made Dane love and trust his brother implicitly. They took care of one another, as Darryl took on the role of their father at times.
As Dane was working the comedy clubs in the early 90’s, gaining his chops, Darryl was a corrections officer at a county prison. Darryl had a wife and child and wanted to forge his own path as a provider for his family, but when Darryl was nearly brained by an inmate at work (which sent Darryl to the hospital with an open head wound), Dane stepped in as a savior, and asked Darryl to be his business manager.
Dane’s mission was to make enough money to take care of himself, and his brother’s family, to protect his brother, and to work side-by-side as a team. Dane made Darryl his power-of-attorney and directed his brother to manage all his money, bills, and taxes. Dane paid Darryl more than he was making at the prison, and Darryl gladly signed on in what would become an incredible ride to the top. Dane became famous in a matter of years, his rise in fame, success, and money was a boon to the family.
Dane focused on creating, making appearances in the media, recording comedy albums, acting in films, and selling out arenas all over the country, while Darryl managed everything else, with no oversight.
When it was time for Dane to buy his first house, it was a beautiful home in the Hollywood Hills (overlooking the Nakatomi Tower, the building from Die Hard) Dane had some questions about the affordability of his dream home. He recently hired a big-time manager in LA to help them grow the business even more, and they requested Darryl to send over the financial files from Boston. Darryl never acquiesced.
One morning Dane woke-up in a panic, he had an epiphany…. “My brother stole all of my money,” he feared. He raced to his local bank and discovered what he assumed was 12 million in savings was only one hundred thousand dollars and change remaining.
They discovered that Darryl had recently cut himself a check for three million dollars and was on the lamb. He disappeared. His best friend, closet ally, and brother essentially wiped Dane out clean.
The scariest part of Funny Money isn’t the theft. It’s that Dane never looked at his own numbers.
Over roughly four years (2004-2008), at least $12M was siphoned out of his accounts by Darryl and his wife. It wasn’t a masterminded heist, rather years of testing the waters, squirrelling away increasingly larger sums of cash, assets Darryl must have begun to believe he deserved or was owed. They discovered Darryl and his wife had bought multiple properties, expensive cars, businesses, and literally hid vacuum sealed bags of cash in every nook-and-cranny of their homes, even in frozen containers of pasta sauce.
For years, Darryl was writing himself check after check and Dane never knew his accounts were dwindling. He never asked to review any account statements, nor did he even bother to write-down his own account or routing numbers… he just trusted Darryl would watch out for him.
Twelve million dollars was gone, plus roughly six years of unpaid taxes (equaling $6 million) that Dane now owed to the IRS. It hit him like a ton of bricks.
The theft was only half the damage… their relationship would die overnight.
It made me reflect on my relationship with my big brother, Pete. I thought about how I would feel or react if my relationship with my brother turned adversarial and was effectively terminated like that. My brother has always been a guiding light to me, an inspiration, someone I’ve tried to model my life after, in many ways. He’s funny, carefree, positive, inquisitive, hardworking, a real family man, and someone I could always count on to give sage advice during whatever turmoil I’m going through. Pete possesses the most positive outlook on life than anyone I know, plus he makes the best shish kabobs.
In my younger days, I was going through a major break-up and my brother was the one who held my hand through the darkest times. He let me grieve, gave me space, while also giving me perspective on my situation. Pete gave me practical tools to help me overcome my situation. Whenever I’d see my brother, whether we were fishing on a guy’s weekend, or during a holiday, we’d fall right back into making each other laugh… he’s the person I’m my trustiest authentic self around.
Dane probably felt the same way about Darryl, and that’s exactly the problem with mixing family and business without checks and balances.
Trust is a relationship. Oversight is a system. They can work in harmony.
Dane’s mistake wasn’t loving or trusting his brother. It was treating love as a substitute for visibility. Dane never took ownership of his own success, he only dealt with the fun spending side of money, he never took the time to look at his own spending, assets, or have any insight on how it was invested. He didn’t even know how much money he actually had or if it were even generating passive income or interest through common-sense money management.
Watching the documentary, I saw Dane in a whole new light. I genuinely felt bad for him. He’s a very likeable guy, and although I never bought his comedy albums or saw him live in concert, I can see how he became the star he is… and you can visibly see the pain he felt when he discovered his most trusted confidant was robbing him blind.
Betrayal by family seems worse because the alarm bells never go off. So, checking the numbers wouldn’t have been an accusation or a litigation of his brother’s management, but it would have signaled a partnership and interest in the financial success of the business. It would have empowered Dane to understand his brand more intimately, while also keeping his brother’s desire to enrich himself in check. Darryl probably took a little to pad his coffers, but that was a slippery slope. A little at times eventually became everything.
Transparency is key to a real partnership, it protects the relationship, avoids putting a trusted source in a position to even have that much power. Power can corrupt after-all, if we let it. Checks and balances, order, and a clear communication plan only incentives us all to do better.
I’ve learned a lot about money and manifesting from my wife over the years, so I’m going to list off some practical solutions I took away from this documentary that she’d agreed with… regardless of your wealth or status… and especially in any partnership or marriage:
Look at your accounts yourself, on a regular schedule
Know what you owe, especially taxes
Have a second set of eyes (CPA or independent accountant) who doesn’t report to the person running your money
Have access to statements or have them sent to you directly, not routed through your third party
Know what “normal” looks like so the abnormal jumps out
Professionally, I'm a TV producer not a money person, but I’d never sign off on a budget I couldn’t read, so why would I treat my own life differently?
After watching this film, I found myself asking, what would I do if this business relationship pertained to me and my brother?
I don’t think I’d ever put that much responsibility in one person’s hands in the first place, but if I did, we’d set clear expectations and a communication plan that had checks-and-balances. My brother and I would treat our arrangement as a co-equal partnership, a creative / mutual endeavor with clear responsibilities, but also transparency and unification…. On all levels.
We’d have an easy conversation at the beginning: “If anything ever happened, I want us both covered. Transparency protects us.”
Our closest relationships can handle open books, and the ones that can’t are already a risk.
If you’re in a marriage, this translates to that relationship too. Katy and I have an open book policy.
Full transparency, I do let Katy handle the day-to-day bills and overall management of our finances, but we have money discussions on a quarterly basis, reviewing where we’re at with investments, debt, and savings, etc.
The documentary begins with a phone call and voice message from Darryl to Dane. Darryl says in a panicked voice, “Dane, it’s your brother…. What’s going on Dane? I was just told… the FBI is involved... What have you done? I’m so scared right now, what have you done? … Why are you doing this to me?”
We learn in the documentary that this voice message was left by Darryl weeks after he disappeared with all of Dane’s money. Weeks of him ignoring Dane’s calls. Darryl left his brother no choice but to call the authorities. Essentially destroying their brotherhood and partnership forever.
I’ve already spoiled enough about the documentary, so I’ll let you see what happens next, but overall, I was really impressed how Dane turned the worst thing to ever happen to him into a documentary with a sense of humor, introspection, and vulnerability.
I’m typically not this introspective about everything I screen, but this documentary left an indelible mark on me. Highly recommend it.
Love your family. Read your statements. To the future.
~Michael Mazzara
How to Work w/ Katy on financial transparency, click → WORK W/ KATY
Streaming on Netflix: Funny Money: The Dane Cook Story