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Beyond Biglaw: 3 Lessons From Uncle Tony

Daily Legal Briefing by Daily Legal Briefing
September 26, 2026
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Beyond Biglaw: 3 Lessons From Uncle Tony
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Blank Lawyer Type Sign or Shingle.In my early days as a Biglaw associate, I used to enjoy having some office background noise, particularly in the middle of the day, when things were generally least hectic. For some time, my go-to indulgence was an ESPN Radio show hosted by Tony Kornheiser, Long Island’s native sports-focused polymath, famous for his work as a Washington Post sports and style columnist, as well as for his television gigs as an analyst for Monday Night Football and as a host of ESPN’s Pardon the Interruption.

Even though his radio show provided a heavy dose of his adopted hometown Washington D.C.’s perspective when it came to sports, I enjoyed his radio presence immensely, especially his repartee with a rotating phalanx of co-hosts and frequent guests. While he was more of a Seinfield-ian observational humorist than outright comedian, the banter and good cheer on his show were a welcome respite from the grind of associate life. Especially when Tony would do what he was best at, namely, poke fun at himself as a bald, orange guy.

As with many passing pleasures, I stopped listening to Kornheiser’s radio show on a regular basis, even as I enjoyed an occasional dose (especially when traveling, as the show is excellent airplane fare) of Pardon the Interruption. Since my listening habits, as I suspect those of many others, have transitioned from live radio to podcasts, I was delighted to hear a month or so ago (while listening to an archived Bill Simmons podcast that had been on my phone for weeks where Kornheiser was the guest — welcome to the podcast era) that Kornheiser was launching a daily podcast as a replacement for his radio job.

Even though I joined the Kornheiser podcast subscriber club a month late, I did subscribe to the podcast as soon as I could, and have been hooked ever since. The length is perfect for my commute, and I enjoy the old standbys such as Old Guy Radio and the Mailbag. More than anything, however, I have a newfound respect for Kornheiser’s willingness to embrace the entrepreneurial challenge of leaving a comfortable radio position to launch his own podcast — thereby taking a chance on himself, as well as his audience’s embrace of new technology.

In some ways, I see parallels between Kornheiser’s decision and the one taken by myself and many other Biglaw refugees. Trading job security (however ephemeral in reality) and access to a deeper resource pool in exchange for the higher highs and lower lows of owning your own business is always a decision I will respect when others take it. More importantly, I think there are some solid lessons we can take from how Kornheiser has gone about his new venture that are applicable to smaller and start-up law firms. There are three that jump out, courtesy of my favorite “Uncle Tony.”

Tony Kornheiser (by Schell Brothers via Wikimedia)

Tony Kornheiser (by Schell Brothers via Wikimedia)

First, listening to his podcast reminds me how much people root for the underdog to succeed. But only when the underdog has a legitimate shot at success to begin with — whether that comes from having the right pedigree or a killer business plan is immaterial. Furthermore, the underdog has to appeal for help from others in a way that comes off as endearing, as opposed to entitled. Kornheiser, with his gift for self-effacement and self-deprecating humor, plays this riff perfectly (especially when he laments giving up his paycheck to launch the podcast). We know he is a famous personality with a built-in audience, and we know that he knows it too. But hearing his appeal for sponsors and listeners is endearing nonetheless. Part of success as a small business owner is knowing when, who, and how to ask for help at key moments. Uncle Tony shows us how to do it effectively.

Second, part of the show’s appeal is how well-connected Kornheiser is, as reflected by the quality of his guests and co-hosts. Likewise, it is nice to see that his son Michael has a role on the show, even if his job title vacillates between “in charge of marketing” to “strategic planner.” There is a strange temptation among some entrepreneurs to try and succeed without tapping into their professional or familial networks. Uncle Tony avoids that mistake, and reminds us that the people closest to us can sometimes have a lot to offer our firms. Utilizing their help does not detract from any success we achieve, and can play a strong part in making that success more likely,

Finally, and most importantly, Uncle Tony innately grasps the most critical factor to the success of a new small service business headed by a refugee from a larger enterprise. Namely, offering those services without any drop in quality from those offered while you were working in the big leagues — while at the same time making it as easy as possible for people to access and relate to you in a way they couldn’t at your prior employer. Two examples from the show are the “jingles” (where listeners submit their self-recorded music) and the “mailbag” (where the host reads and responds to emails from listeners). Uncle Tony understands that if you forge a stronger bond with your audience, while also delivering the goods in a way that meets or exceeds what they are used to, you have a head start on success, no matter how risky your plunge into self-employment may have felt at the beginning. What works for him with his audience can surely help us with our clients. So listen to Uncle Tony, and remember to please wear white.

Please feel free to send comments or questions to me at [email protected] or via Twitter: @gkroub. Any topic suggestions or thoughts are most welcome.


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 [email protected] or follow him on Twitter: @gkroub.





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