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Beyond Biglaw: When To Never Give Up (Or, What Lawyers Can Learn From Bill Simmons)

Columnist Gaston Kroub examines the career of Bill Simmons, the bestselling author and sports television personality, and pulls out wisdom for lawyers.

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It is hard to be a sports fan nowadays and not have an opinion about Bill Simmons, the editor-in-chief of ESPN’s Grantland.com, bestselling author, and sports television personality. I happen to enjoy his work, especially his writing and frequent podcasts with various sports and media personalities — including some of his friends, like Jacko and House, who have become “personalities” themselves (precisely because of their appearances on Simmons’s popular B.S. Report podcast). Because of his popularity, and ubiquity, Simmons has also become a polarizing figure, who has himself publicly chafed at the strictures imposed on him by his corporate overlords at ESPN. At the same time, ESPN recognizes his importance to their various franchises, and his contribution to making sportswriting on the internet a viable and lucrative alternative to the newspaper or magazine sports columns of yesteryear.

Even though he is not a lawyer, in many ways Simmons demonstrates the characteristics of many of the more successful attorneys I have encountered in my career. First, he demonstrates a “better to ask for forgiveness, rather than permission” attitude, especially when it comes to branching off into new directions. Sure, he may have started his career as a writer, but when the opportunity arose to start a podcast for example, he took it — and thrived. Likewise, when there was an opportunity to work on television as a basketball analyst, he donned the makeup — despite admitting publicly that it was difficult and unnatural role for him to be on camera. Simmons has even branched out to become a television producer, as the creator of the Emmy award-winning 30 for 30 series of sports documentaries. In short, Simmons is willing to take risks, and experiment, and doesn’t talk himself out of trying new things, unlike many lawyers I have seen who lack the self-confidence to even try a new approach. The fear of failure is that strong in our profession. But there is no doubt that many firms need partners who are willing to demonstrate a “builder mentality,” rather than a “bunker mentality” that is satisfied with the status quo.

What makes Simmons’s example relevant to lawyers is that he has done all this within the context of an organization, ESPN, just like successful rainmakers thrive within the context of their firms. For example, many rainmakers will tell you that their success came from encouraging their firms to allow them to target a new niche practice area, and that while their firm was supportive of their attempts to increase the client base, there was also the expectation that they bring in the new business without slacking off on their normal responsibilities — to bill and collect, at minimum. I am sure Simmons needed “buy-in” from ESPN before starting the 30-for-30 project, for example, and while he was obviously able to get them to take the risk and expense of funding an untested new project, I also do not doubt that he was expected to continue performing all his “normal” responsibilities at the same time. Those responsibilities did not dissuade him, just as the most successful lawyers are usually the ones most willing to add more to their already full plates in the service of growth.

Another quality that Simmons demonstrates that I have seen in rainmakers is a conversational communication style. Yes, Simmons is not a natural on television, but as a writer, his voice and unique style make his work both entertaining and rewarding to the reader. On top of his prose style, Simmons is also a willing experimenter with different frameworks for his columns, whether through one of his ever-popular “mailbags” or his various methods of ranking teams, players, or even sports movies. At bottom, Simmons knows how to relate to his readership, and conveys his written opinions and observations in a lucid but also frequently humorous way. Rainmakers similarly excel in communication, whether it be with their staff, clients, or fellow partners. Many of them do not need to “put on airs” but are instead personable, direct, and easy to engage with. There is a reason clients like interacting with them.

Perhaps more than anything, what makes Simmons interesting is the simple fact that he very nearly never became a successful writer in the first place. In a recent podcast, he told his “origin story,” and related just how close he was to quitting before he got his big break and was picked up to write for ESPN.com. In fact, he spent a year not writing at all, killing time as a bartender, before taking a chance and writing a sports column for what was then an affiliate of AOL. Even though he was not making much money doing that column, he gave it everything he had, and approached it as if he had 1 million rather than 10,000 readers. I found the story he told fascinating, and what it illustrated clearly for me was the critical importance — for people who have true career goals — to never quit in pursuing them, no matter how far away it feels that success is. Because when you are like Simmons and have a true dream, and are also prepared to outwork everyone in your path to achieve it, then success is often possible. Of course you will encounter setbacks, but quitting in the face of those setbacks would only bring a lifetime of regret and second-guessing — whether your dream is to be a writer, a lawyer, or a sheepherder.

In contrast, for those who find themselves with no dreams, or who are working as lawyers just for the sake of having something to do, the idea of quitting to pursue an alternate passion can be a good one — especially since people can discover their passions at different stages of their lives. If you are unsure about whether a career in law will satisfy your personal goals, talk to a rainmaker or lawyer whose career path you admire. Ask them their “origin story” and listen carefully for those places where they describe the sacrifices they made to get to their current position. And ask what they like best about being in their current position, especially if they start talking about all the new things they want to try as their career progresses. If hearing about the sacrifice required makes you cringe, or if the idea of branching out from “just being a partner” is not attractive, there is a decent chance that law is not your true passion. That is not to say that you can’t have a fulfilling legal career even if you approach your work as a lawyer as simply a job. But if you aspire to more, and find yourself frustrated by the slow pace of your career progress, think about Simmons (or some other person whose perseverance has paid off), and how easy it would have been for him to quit. Once you re-gird yourself for battle, think about how he has seized — or created — the opportunities afforded to him. And resolve to do the same.

Please send any comments or questions to me at gkroub@kskiplaw.com or via Twitter: @gkroub. Any topic suggestions or thoughts are most welcome. For those interested in the intersection of intellectual property litigation and investing, I have also started a new blog/newsletter/video series, “The Markman Note,” which is being hosted at Mimesis Law. Feel free to check it out and let me know of any thoughts or suggestions.

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Gaston Kroub lives in Brooklyn and is a founding partner of Kroub, Silbersher & Kolmykov PLLC, an intellectual property litigation boutique. The firm’s practice focuses on intellectual property litigation and related counseling, with a strong focus on patent matters. You can reach him at gkroub@kskiplaw.com or follow him on Twitter: @gkroub.

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