Windings Paths is a personal growth podcast for lawyers. My goal is to empower you to take ownership of your own winding path sharing the lessons and stories of attorneys who've made interesting turns on their journeys, and the insights I've gained walking my own. I invite you to grow with me. May you walk your own winding path well. Joseph Gerstel Connect to me on LinkedIn and say hello - I can never have too many friends in my life: https://www.linkedin.com/in/josephgerstel/ Follow me on T ...
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Ep. 26 | Michael Fertik on Building Like a Zillion Companies and on Law School
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Today I am talking to Michael Fertik. Michael Fertik is a serial entrepreneur and investor. He is the Founder and Managing Partner of Heroic Ventures, Reputation, SightGlass, b4.ai, and others. He is also the author of several books of fiction and non-fiction, including the New York Times bestseller The Reputation Economy and a frequent contributor…
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Ep. 25 | Mat Rotenberg of Dashboard Legal - Stop Lawyering Out of Your Inbox
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In this episode I talk to Mat Rotenberg. Mat is the CEO and Co-Founder of Dashboard Legal. If you're constantly searching through your emails to find documents, updating word checklists or Excel trackers, or just aren't sure which version of a document everyone is working on, Mat is here to save your life. Dashboard Legal is a project management to…
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Ep. 24 | Aliza Shatzman on Accountability in Clerkships
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In this episode I talk to Aliza Shatzman, President and Founder of the Legal Accountability Project, a nonprofit focused on ensuring that law clerks have positive clerkship experiences. Aliza got her JD from Washington University School of Law where she was an associate editor for the Journal of Law and Policy. After Law School. Aliza clerked in th…
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Ep. 23 | Greg d'Incelli - A Trial Lawyer Launches a Crypto Fund of Funds
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In this episode, I talk to Greg d'Incelli. Greg is a graduate of the University of Miami Law School and worked for a number of years as a trial lawyer trying plaintiffs’ personal injury cases before he parlayed an interest in crypto into his own crypto investing operation Scenius capital. As you'll hear more in the episode, Scenius runs a fund of f…
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Ep. 22 | Keith Lee on Learning to Market Yourself, Building an Audience, and Whether Law School Makes Financial Sense
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In this episode I talk to the wonderful Keith Lee. Keith is a graduate of Birmingham School of Law and is a principal at Sidebar Ventures. He is the founder of Associates Mind, a blog on being a better lawyer, and of a paid Slack community for lawyers called Lawyer Smack. Keith is also the author of the Last Week in Law newsletter. In this episode …
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Ep. 21 | Adam Hootnick - Leaving the Law Behind for Documentary Filmmaking
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In this episode I talk to Adam Hootnick about never using his law degree and pursuing a media and filmmaking career instead. Adam is a graduate of Harvard Law School, but never did anything with his law degree. Instead, he went to work as a production assistant for MSNBC one day before September 11th, 2001. That was a very interesting time to start…
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Ep. 20 | Jordana Confino on Wellness in Law and Leaving the Herd and Finding Your Own Way
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In this episode I talk to Jordana Confino about her career pivot into wellness in the legal space and about wellness in the legal space. Jordana is a graduate of Yale law school. She serves as the Assistant Dean of Professionalism and an adjunct professor at Fordham Law School, where she leads initiatives designed to promote student wellness, leade…
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Ep. 19 | Brian Wood on Playing Poker Instead of Going to Big Law
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In this episode I talk to Brian Wood, or more accurately, my former co-host, Aaron Shapiro talks to Brian Wood, as my audio was garbled. I’m editing a backlog of episodes and I had a mic issue for a while which we didn’t catch so there are a few episodes like this. Moral of the story is don’t record 10 episodes without listening to them. Brian is t…
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Ep. 18 | Drew Amoroso on Enjoying Your Work and Coaching for Lawyers
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Drew Amoroso is the CEO of Due Course, a coaching platform for law firms that allows lawyers to find coaches who specialize in helping busy lawyers in a variety of areas like wellbeing, leadership, business development, time management, wise mindsets, and so on. Drew and I get into the coaching craze and why it could be valuable to have someone enc…
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Ep. 17 | Doug Bouton - From Big Law to Big Ice Cream
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Doug Bouton is the CEO of Gatsby Chocolate, a low on sugar, high on taste, chocolate brand (now that’s Doug’s claim – I haven’t tasted it yet, and when I do, I’m sure it will be amazing, but if it’s not high on taste, I’ll be sure to lie about it. Nah, Doug has a good track record). He’s also the CEO of Halo Top International, a low calorie, high q…
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Ep. 16 | Michael Bloom — Financial Crisis Grad Becomes Accidental Law School Prof and then Builds Contracts Teaching Software — And is Law School Useful?
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Michael Bloom is the CEO of Praktio, a platform that helps junior lawyers at law firms learn how to draft contracts, which is used by over 50 of the AM Law 200. Michael graduated from Yale Law into the Financial Crisis and took a voluntary deferral from Sidley Austin. Rather than twiddling his thumbs, Michael found a role teaching a clinical contra…
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Ep. 15 | Raleigh Williams on on Acquiring Small Businesses, Hightailing it out of Big Law and Moving into His Mother in Law’s Basement, Leading the Life You Want, and Other Very Engaging Stuff
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This is a killer episode. I loved this conversation and I think you're going to enjoy it a lot. I'm talking to Raleigh Williams. Raleigh is the CEO of DealMaven.io, a marketplace for buying and selling small businesses. Raleigh is, of course, a former lawyer and he lasted all of nine months at Skadden before he hightailed it out of there, straight …
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Ep. 14 | Sigalle Barness on Graduating into the Financial Crisis and evolving into Chief Storyteller at Lawline
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Sometimes you get dumped into rough waters you didn’t know to expect. Sigalle Barness graduated law school right in to the middle of the Financial Crisis and let’s just say at a time that many of her fellow grads were taking work as waitresses(!) or other decidedly non-legal, non-sexy occupations, getting a traditional firm job was not so easy. Com…
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Ep. 13 | Jonathan Vaas on Heading Up Investor Relations at Adobe
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Jonathan Vaas heads up investor relations at Adobe and loves his job! In this episode we talk about the long path to his current role, how he got there from the legal side, and important lessons he’s learned along the way. Wherever you are on your winding path, come listen and learn from the twists and turns on Jonathan’s so you can walk your’s wit…
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Ep. 12 | Robert James II - On returning to his roots at Carver State Bank
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Robert James graduated from Harvard Law School with dreams of becoming governor of Georgia. Robert now runs Carver State Bank, a community bank serving underbanked communities in Georgia and one of only 19 (out of 4,500) black-owned banks in the country. Listen to the story of Rob's winding path from the law to his current position as the president…
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Ep. 11 | Jerry Ting - From Law School Startup to $100 Million Series C Raise
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Jerry Ting was a 2L when he started Evisort, a legal tech company that just raised a $100 million Series C round. Evisort is an AI-software company that helps companies manage their contracts. Jerry had the initial idea for Evisort while working in a clinic in law school and paired up with an MIT student who he was advising to start the company. Th…
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Ep. 10 | Kiwi Camara - From Small Firm to Publicly-Traded Legal Tech Company
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Kiwi Camara skipped high-school and graduated college at the ripe old-age of 16. He was 19 when he graduated Harvard Law School. This youngster formed a close friendship with his oldest classmate and shortly after graduating they formed their own commercial litigation law firm. It took them six months to land their first client, but they persisted.…
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Ep. 9 | Jared Craft - Associate to Clean Tech Entrepreneur
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Jared Craft summered at Bingham McCutchen during the financial crisis. At the beginning of the summer, Bingham told the summer class that only half of them would get offers. Yeah, that happens. Jared survived the summer purge and worked there for a bit but then soured on his law firm experience after his (gentler) firm was acquired by another firm …
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Ep. 8 | Jessica Maroney Shillito on Building a Career in Diversity and Recruiting in BigLaw
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Jessica Shillito has been in Big Law since she graduated from Harvard in 2006, but not as a lawyer. She is one of a number of lawyers who've made the hop from the legal side to a non-legal function in a law firm. After one year of practicing as a labor and employment attorney, Jessica jumped to a recruiting function and built a career as a recruiti…
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Ep. 7 | From Big Law to Big Ten: How Adam Neuman became Chief of Staff of the Big Ten Conference less than two years out of law school
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Adam Neuman is a sports fanatic. Adam is Chief of Staff and right-hand man to Kevin Warren, Commissioner of the Big Ten Conference. He’s less than four years out of law school, and get this, he nabbed this pretty cool position less than two years out of law school. How did Adam do it? Well it’s a bit of a crazy story... And you’ll just have to list…
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Ep. 6 | Samantha Coxe, CEO & Co-Founder of Flaus
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Samantha Coxe was spending multiple nights on the floor in her office at Skadden when she decided to make her entrepreneurial dreams a reality. After three and a half years as an M&A associate, Sam jumped ship to launch Flaus, a dental wellness company focused first on developing an eco-friendly electric flosser. In this episode we discuss: How Sam…
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Ep. 5 | Alex Knight: Corp. Associate to Chief Revenue Officer at Best Company
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Alex Knight always had a hunch that he would ultimately pursue something outside legal practice. So after graduating from Harvard Law School in 2018, and spending just under two years as a corporate associate at Fenwick & West out in California, Alex moved home to Utah to start working as Director of Strategic Initiatives at Best Company, where he …
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Ep. 4 | Jake Yormak: Junior Associate to Founding His Own VC firm
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Hear about how Jake Yormak went from being a junior associate at a premier New York law firm to founding his own venture capital firm, Story Ventures, with his brother If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Check out my unbelievably amazing personal g…
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Ep. 3 | Sam CC: Law School Grad to Director at Snap
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If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Check out my unbelievably amazing personal growth newsletter at ExcellentatLife.com. The critics are going mad over it so I'm sure you will as well. In the meantime, may you walk your own winding path well. Josep…
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Ep. 2 | Jim Brennan: Federal Clerk to BCG Partner
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If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Check out my unbelievably amazing personal growth newsletter at ExcellentatLife.com. The critics are going mad over it so I'm sure you will as well. In the meantime, may you walk your own winding path well. Josep…
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Ep. 1 | Jason Sherman: Biglaw Associate to Beer Startup Founder
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If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Check out my unbelievably amazing personal growth newsletter at ExcellentatLife.com. The critics are going mad over it so I'm sure you will as well. In the meantime, may you walk your own winding path well. Josep…
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