5 Entrepreneurial Lessons From Fantasy Life by Matthew Berry

In Fantasy Life, Matthew Berry spells out his journey from Hollywood screenwriter to fantasy sports mogul. What can the Talented Mr. Roto teach us about modern entrepreneurship?

Here are 5 thoughtful lessons from the book.

Fantasy Life by Matthew Berry

Before he became known as the “Talented Mr. Roto,” fantasy sports guru to millions, Matthew Berry started out as a screenwriter for Hollywood.

Berry and his writing partner were among the dozens of writing teams to pitch Paul Hogan directly on ideas for the third installment of the Crocodile Dundee movie franchise. Their approach was simple: “There’s lots of craziness here [in Hollywood], you’ll wander around and react to stuff. I mean, come on, it’s Crocodile Dundee. We’ll make it funny.”

They didn’t expect much. But what happened next shocked them.

And there was a long pause as he looked at us. And then he said, in that unmistakable accent. “Ah, you guys are the only ones who get me. You’re hired.”


It turned out that most of the other writers had pitched outrageous scenarios for Hogan and the Crocodile Dundee character, like Crocodile Dundee in Space, forgetting what made the character work in his first two movies.

Even still, Berry and his co-writer were hesitant to accept the gig. Was Crocodile Dundee in Los Angeles really the type of movie they wanted to write?

Berry’s agent coaxed them into taking the job: “You’ve never written a movie before. They will pay you to write one, and if it’s good, you can use it as a sample. And guess what they want to pay you?”

It was a life-changing amount of money. “If you’re gonna sell out, kids, sell out big,” Berry writes.

The movie turned out so-so. By Berry’s own admission, it’s “very, very vanilla.” But mediocre movies have never stopped anyone in Hollywood before. If a forgettable film was the extent of the damage to the writing duo’s careers, Berry might still be writing screenplays today. But that wasn’t the problem:

The issue was writing credit. When we signed on to do the film, it was with the understanding that we would share writing credit with Paul. That was fine with us. And that’s how we submitted it to the Writers Guild. But then Paul Hogan—that would be star, executive producer, in-every-single-frame-of-the-movie Paul Hogan, announced that he also needed solo writing credit and wanted our names taken off the script entirely.

While they were not entirely proud of the film, Berry and his partner would face significant financial drawbacks if their names were removed from the script, including any future residual income from the film. “The whole reason we wrote the damn thing was money,” Berry writes.

Hogan and the writing partners went through a lengthy arbitration process, including multiple appeals, with Berry and his partner winning at every level. Meanwhile, Hogan claimed in media appearances and interviews that the duo were receiving writing credit they didn’t deserve.

The whole thing was humiliating and horrible, and I hated almost every moment of it. Suffice it to say, I am not a fan of Paul Hogan, the human being. That movie bought me a nice big house in Los Angeles. But it was a painful, hurtful experience, and it taught me a very powerful lesson: doing something you don’t care about kills you inside. And a lot of money won’t change that.

The Crocodile Dundee 3 story is just one of the many fascinating vignettes from Fantasy Life: The Outrageous, Uplifting, and Heartbreaking World of Fantasy Sports From the Guy Who’s Lived It by Matthew Berry.

It might seem odd to feature the memoir of a fantasy sports writer on Agile Lifestyle, but Matthew Berry’s journey from a screenwriter to a website columnist to a full-blown fantasy sports entrepreneur is an instructive one for lifestyle agilists, even those who don’t care at all about sports.

(Let alone fantasy ones.)

Matthew Berry: Fantasy Sports Entrepreneur

Matthew Berry Fantasy Life - Book Cover

Cover image via Barnes & Noble. Used under fair use.

In 2003, Berry was having dinner with an Internet entrepreneur-friend who was mulling over the potential acquisition of a new website. The site had made $60 million in profit the previous year, and the seller was asking for $60 million for the whole thing.

It was a great price.

The catch?

It was an adult website. Specifically, the site was one of those “age verification” sites that, at the time, solved the two biggest problems that porn sites had: proving someone was of legal age to view the content and credit card chargebacks.

Anyway, this company had come up with a simple and ingenious solution. They went to all the adult websites and said, hey, we’ll handle that hassle for you, charge a decent fee to customers (like $30 a month), take a slice off the top, and send you the rest. And they did this for a lot of websites. So, for $30, a customer actually got access to tons of different adult websites. For the websites, it solved a major headache and got more customers to their site than they might have drawn otherwise. Plus, under the group business plan, they were making money even if a customer didn’t come to their specific website.

The age verification site didn’t have to hire models or produce content. It simply acted as a pay gate for the content of others—in this case, adult websites.

It basically ran itself. It was (and remains) a brilliant business model. And it occurred to me … what other business has a hard-core, passionate fan base willing to spend money on premium content?

I called it RotoPass.com

Berry ported the paygate model he learned about from his friend to the dozens of fantasy sports websites in the market.

At first, Berry didn’t think the fantasy sports site would be his full-time gig. “I didn’t want to give up show business, especially when it seemed like things were finally moving in the right direction, but I saw an opportunity in the fantasy sports business space. … I could continue my movie-writing career, and I’d make some nice side money in fantasy.”

At the same time as RotoPass was getting off the ground, Berry was writing a weekly column for a leading fantasy sports site, Rotoworld, as the “Talented Mr. Roto.” Berry was paid $100 a week.

As the dot-com bubble burst, the site owners came up with a plan: cut costs by paying writers less (surprise surprise).

Would Berry take $25 a week to do the same column, plus the radio shows, trade shows, and public appearances he was already doing?

Berry said, “Wait, after writing for you for four and a half years, you want to cut my pay 300 percent?”

To which Rotoworld replied, “Well, when you say it that way it sounds bad.”

If you had any lingering doubts whether Matthew Berry is a good example of an entrepreneur story, check out the following passage, so typical of the entrepreneurial personality:

Throughout my life I have tended to react very poorly when I think I’m being treated unfairly. I am a very black-and-white kind of guy, and for whatever reason, fairness is a huge issue with me. The majority of problem I’ve had with authority figures, from childhood to twenty minutes before I wrote this, stem from something happening to me that I deem to be unjust or unfair.

So it’s pretty surprising that I didn’t just scream at the guy for 10 minutes, burn the bridge, and never speak to him again. It’s not that $25 or $100 made that much of a difference in my life. I obviously did this job for the joy of it, not the money. But it was the principle. I had done really good, high-quality work for them, built an audience, promoted them on radio, never missed a deadline, and now this?

He told Rotoworld he’d think about it.

In the meanwhile, he hatched a plan to keep his readers, who he knew were as loyal to him as they were to Rotoworld.

He started a Yahoo interest group and began to collect emails, like any good Internet entrepreneur. He began to field offers from competing fantasy sites. “But before I decided what website I would start working for, the Yahoo group exploded. I had over 6,000 members in two weeks and a very active message board, which in those days in the fantasy sports universe was a really good number.”

His bosses at Rotoworld eventually found out and fired Berry. But the Yahoo group was growing. “It quickly developed into a fantasy sports community, and its fast growth led me to think, Hey, instead of joining another site, why don’t I just start my own?”

Berry started TalentedMrRoto.com and launched a quick and cheap website. “I didn’t care if the site was any good, I just needed some sort of content. My grand plan was that the TMR site, as it came to be known, would be one huge advertisement for RotoPass.”

How to Turn a One-Time Appearance Into a Weekly Gig

Fox Sports Radio by that time had been hosting Berry’s fantasy musings on a regular basis. They initially offered Berry a call-in segment, but he insisted that the studio was close and that he was able to come in person.

Of course, the studio wasn’t all that close and his excuse about the audio quality of in-person vs. on-the-phone masked his real purpose:

I didn’t care about the clarity of the audio. I wanted it to be as good a segment as it could be, of course, but more important, I wanted to meet them. Once I met them, I wasn’t just some voice at the end of a phone. Now I’m a guy they’ve shaken hands with. BS-ed with before and after the segment. Now I have a relationship with these guys, as opposed to being some faceless email saying, “Hey, how about next week?”

The first segments went well, the guys were all nice, and I was invited back for the following week. And the week after. Steve eventually asked me to do two segments, which eventually turned into doing an hour and then guest hosting over the holidays to all the way to (after lots of meetings and proposals to the Fox Sports Radio bosses) a job in 2004 and 2005, when I became the official Fox Sports Radio fantasy “expert,” doing hits on the air throughout the week and doing fantasy updates every hour on NFL Sundays.

The lesson in all this? “Talk to people. Face-to-face. Whenever possible.”

Why You Don’t Get Second Chances in Hollywood

Later in the book, Berry relates the sage advice of one of his screenwriting mentors, a highly successful sitcom writer:

He explained that there was no conspiracy to keep good people out. “When we open a script, we want it to be great. We are rooting for it. But most times it isn’t. So we pass. And because we get so many submissions, we have limited time. So if I see another script from someone I’ve already read and passed on, I’m not reading a second one. Life’s too short.”

He continued with me. “Look, you’ll get your shot. Everyone who’s persistent enough always does. But when you get your shot, make sure you’re ready. Because you only get one.”

5 Clutch Takeaways From Fantasy Life by Matthew Berry

1. Doing it only for the money kills you inside.

Berry’s experience on Croc 3 is instructive. Few of us are offered big Hollywood money to sell out, yet many of us do it anyway, thinking we can keep our integrity while doing something we hate. In Fantasy Life, Matthew Berry bursts that delusion. “If you’re gonna sell out, kids, sell out big,” he said, and he was still miserable in the end. What are you saying about your self-worth when you sell out for peanuts?

2. Cultivate your own audience.

Matthew Berry’s fantasy audience was interested in him—his viewpoint, his story, his life—more than they were interested in the site he was writing for, Rotoworld. When he broke away from Rotoworld, his fans followed him. How many of us are providing reams of content for other people’s platforms? Facebook, Twitter, YouTube, commenting on other people’s blogs, etc. Make sure your audience knows where to find you independently of any third-party platform (that’s why I recommend everyone start a website even if you’re a newbie).

3. Cross-pollinate business models and ideas.

Following the advice to tinker outside one’s own field, Berry combined aspects of his friend’s business model and his own interest in fantasy sports to create RotoPass, a product that continues to sell to this day.

4. Talk face-to-face whenever possible.

The Agile Manifesto says face-to-face interactions are best and Berry would agree. By ingratiating himself with the Fox Sports team in person, they were more likely to give him more work and keep him in mind for future projects.

5. You may only get one shot, so make sure you’re ready when it counts.

Whether you’re toiling in a “pick me” industry like Hollywood or legacy book publishing or pitching a prospective client or business partner, first impressions can become last impressions if you aren’t careful.

Top Photo Credit: bibendum84 via Compfight cc

Opt In Image
How Much Time Would You Save With the Right Tools?
Get the 'App Guide' for Download NOW

In this free guide, I reveal the top 7 apps that make my career and personal life run smoothly. Hint: 5 of the apps I use every day are totally free! Sign up to receive blog updates, exclusive content, and the resource guide FREE!