Winding Paths

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 to global media. He is a recipient of the TechAmerica Entrepreneur of the Year award and a WEF Technology Pioneer. He has taught at Harvard for almost a decade.We got into a lot about all this so have fun listening! 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.Joseph Gerstel

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 tool for lawyers that lets you stop working out of your inbox and start working out of a centralized dashboard where you can easily find what you need and collaborate with others in a 21st century way. Welcome to the internet era lawyers! Mat is a graduate of U of Minnesota Law School and worked for seven years in big law  before being brave enough to jump into entrepreneurship. 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.Joseph Gerstel

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 the DC Superior Court during the 2019-2020 term, an experience we discuss at length in the episode. Aliza writes and speaks regularly about judicial accountability and clerkships based on her personal experience with harassment and retaliation during and after her clerkship. She has been published in numerous forums, including the Administrative Law Review, Harvard Journal of Legislation, UCLA Journal of Gender and Law, Yale Law and Policy Review, NYU Journal of Legislation and Public Policy, Above the Law, Law 360, Slate, and a number of other publications.  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.Joseph Gerstel

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 funds of sorts in the crypto space, allowing investors to invest in one vehicle that is then spread out over a number of the best digital assets funds picked by Scenius.Enjoy! If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Connect to me on LinkedIn here and say hello Follow me on Twitter hereCheck out GetSomeClass.com for fun team activities and wellness programming.In the meantime, may you walk your own winding path well.Joseph Gerstel

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 we bash lots of things, talk about marketing and selling yourself, and have lots more fun.Enjoy! If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Connect to me on LinkedIn here and say hello Follow me on Twitter hereCheck out GetSomeClass.com for fun team activities and wellness programming.In the meantime, may you walk your own winding path well.Joseph Gerstel

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 a job in New York city.Adam is now an award-winning filmmaker based in Austin, Texas. His most recent documentary, What Carter Lost,  was named one of the year's best documentaries by Sports Illustrated. Adam has directed a number of documentaries and also does commercial film work such as projects with Serena Williams for Lincoln, Jeff Gordon for NASCAR, and US Olympians for United Airlines, and many more. Needless to say, this is a very different career path, and I hope it will inspire you to follow their own career dream.   If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Connect to me on LinkedIn here and say hello Follow me on Twitter hereCheck out GetSomeClass.com for fun team activities and wellness programming.In the meantime, may you walk your own winding path well.Joseph Gerstel

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, leadership, and professional identity formation. As part of this, Jordana teaches a course in positive lawyering, which teaches students how to harness the power of positive psychology, to reach their highest potential and build meaningful, satisfying careers in law. Jordana is also the founder of JC Coaching and Consulting, where she serves as a professional coach, speaker and advisor to law students and lawyers and helps them learn to inhabit their careers fully and have meaningful work lives. This was a thoughtful and fun conversation. I hope you enjoy it. If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Connect to me on LinkedIn here and say hello Follow me on Twitter hereCheck out GetSomeClass.com for fun team activities and wellness programming.In the meantime, may you walk your own winding path well.Joseph Gerstel

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 the CEO of PanoPick, a peer-to-peer sports betting app that's goal is not to manipulate you into losing your money and get you gambling addicted while warning you about the possibility of getting addicted, but rather to allow you to have some competitive fun betting against friends and finally figuring out who's really knows sports the best. After graduating law school in 2012, Brian went to work at…, uh, actually he went to play poker online in Montreal because it was illegal to play for cash online in the states.  Yep, rather than go the big law route, Brian's been supporting himself playing poker for the past 10 years while he figured out what to do with his lifeThis was a really fun and different conversation. Hope you enjoy. If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Connect to me on LinkedIn here and say hello Follow me on Twitter here and I'll follow you backCheck out GetSomeClass.com for fun team activities and wellness programming.In the meantime, may you walk your own winding path well.Joseph Gerstel

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 encouraging and objective in your camp.Drew graduated from UC Davis Law School in 2010 and worked at Reed Smith for five years before leaving to start his own firm doing “fitness law.” After some time doing that, he started experiencing stomach pain for many weeks and realized he wasn't doing what he wanted to do. Thus began his career in coaching and the journey that led him to founding Due Course. Drew also teaches a class called Practice Ready on being intentional about your legal career at a couple of law schools in California.Drew is going to join me in late January for a workshop on creating intention-driven routines, so if you want to join that, shoot me an email at Joseph@excellentatlife.com. I will also publicize it in the Excellent at Life newsletter, which I hope to launch next week (that's the last week in December) and which you can sign up for by emailing me as well. If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Connect to me on LinkedIn here and say hello Follow me on Twitter here and I'll follow you backCheck out GetSomeClass.com for fun team activities and wellness programming.In the meantime, may you walk your own winding path well.Joseph Gerstel

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 quality ice cream brand. Doug went to the University of Virginia for Law School and aced their famous ice cream making class. I'm kidding. There's no freaking ice cream making class at the Virginia Law School, nor in any law school in the country. Now here's the scoop folks (get it, the scoop?!) – while Doug didn't take a course in law school on ice cream making, I actually did. And no I'm not kidding this time. When I was in law school, I audited an undergrad course at Harvard called the Science of Cooking. (And you can take actually take that course on edX.) It was an unbelievable class, each week one of the best chefs in the world would visit. Now one of the classes was dedicated to, you guessed it, the science of making ice cream.  Doug graduated law school in 2010 and did corporate work at Proskauer for two years before leaving to start Halo Top ice cream with fellow lawyer Justin Woolverton out of Justin's kitchen. The two of them grew the brand to more than $300 million in sales and turned it into the #1 selling ice cream in the United States, outselling the likes of Ben & Jerry's, Haagen-Dazs, and Breyers.  (And that's before Ben & Jerry's stupid boycotting Israel decision.) Halo Top's US operations were sold in 2019, and Doug now serves as the CEO of Halo Top's international operations. In 2021, Doug founded Gatsby Chocolate, the first-ever low-calorie chocolate brand with the goal of doing to chocolate what Halo Top did to ice cream.  If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Connect to me on LinkedIn here and say hello Follow me on Twitter here and I'll follow you backCheck out GetSomeClass.com for fun team activities and wellness programming.In the meantime, may you walk your own winding path well.Joseph Gerstel

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 contracts course at U of Chicago Law School. That course turned into coauthoring a textbook on contracts and ultimately with some hops and jumps and more hops over to launching Praktio.If you're graduating law school now or worried about what's happening in the current economic environment, you might take comfort from the fact that often what we're not expecting ends up taking us down paths that prove to be fruitful and that we may not have anticipated to begin with.This week, Tuesday, December 6th at 6:00 PM, EST, Raleigh Williams from Episode 15 is going to be leading a free workshop on investing in small businesses for busy lawyers.If you want to attend or learn about future workshops like this email me at Joseph@excellentatlife.com.I'm also going to be launching a newsletter shortly called Excellent at Life: A Personal Growth Newsletter for Attorneys and Other Humans. You can sign up for it by emailing me at Joseph@excellenatlife.com or going to ExcellentAtLife.com (will be live shortly). If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Connect to me on LinkedIn here and say hello Follow me on Twitter here and I'll follow you backCheck out GetSomeClass.com for fun team activities and wellness programming.In the meantime, may you walk your own winding path well.Joseph Gerstel

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 into his mother-in-law's basement with his wife and a three-year-old kid.His dad didn't talk to him for two years after, because he was so angry — he even killed the power to an extra house he had in Utah, so Raleigh wouldn't stay there. This episode is full of so many rich nuggets and such an awesome storyline. I hope you have a real good time listening to it.Next week, Tuesday, December 6th at 6:00 PM, EST Raleigh is going to be leading a free workshop on investing in small businesses for busy lawyers.If you want to learn about future workshops like this email me at Joseph@excellentatlife.com.I'm also going to be launching a newsletter shortly called Excellent at Life: A Personal Growth Newsletter for Attorneys and Other Humans. You can sign up for it by emailing me at Joseph@excellenatlife.com or going to ExcellentAtLife.com (will be live shortly). If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Connect to me on LinkedIn here and say hello Follow me on Twitter here and I'll follow you backCheck out GetSomeClass.com for fun team activities and wellness programming.In the meantime, may you walk your own winding path well.Joseph Gerstel

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. Come listen to Sigalle's journey from contract legal work for $20 an hour with $300,000 in student debt to managing leading CLE company Lawline and to her current role as Lawline's Chief Storyteller. If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Connect to me on LinkedIn here and say hello Follow me on Twitter here and I'll follow you backCheck out GetSomeClass.com for fun team activities and wellness programming.In the meantime, may you walk your own winding path well.Joseph Gerstel

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 with a little more wisdom and experience. If you have input, criticism, or guest suggestions (including yourself) for the podcast, shoot me an email at Joseph@excellentatlife.com. Connect to me on LinkedIn here and say hello Follow me on Twitter here and I'll follow you backCheck out GetSomeClass.com for fun team activities and wellness programming.In the meantime, may you walk your own winding path well.Joseph Gerstel

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 of a bank!And don't forget to stay on your own winding path!

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.  They were joined by a couple of Jerry's law school classmates as co-founders and managed to get enough facts on the ground to go run the company full time upon graduation.In this episode we cover how Jerry used his time in law school to get Evisort rolling and how he grew the company to over 200 employees and to its latest venture round.Joseph & Aaron

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. Together they built a successful litigation firm.Realizing one of their client's was spending lots of money on discovery that could be automated, they built an automation tool for that client, then rolled it out to their other clients.A short while later they spun out DISCO as a separate legal-tech company.Last year Kiwi took DISCO public.Check out Kiwi's awesome story!Joseph & Aaron

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 and the culture changed (guess if it was for the better?).Like many other lawyers (or not), Jared now runs a company that optimizes capture of solar energy on moving platforms - boats, CitiBike charging stations, trucks etc. and also runs operations for a large content marketing company.We especially enjoyed hearing about his experience starting at a law firm during the Great Recession and how he made his way to CEO of a a clean tech company.Enjoy!Aaron & Joseph

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 recruiting and diversity leader at  leading law firms. She now serves as Associate Director of Legal Recruiting and Diversity at Simpson Thacher. Her career arc is a great example of the many non-legal opportunities that exist within Big Law. In this episode you'll hear about: Making the shift from attorney to recruiter inside a large law firm Recruiting for BigLaw in the midst of the 2008 recession The important efforts large law firms are making to improve diversity among their associates and partners This was an eye-opening and timely discussion. We hope you enjoy!Aaron & Joseph

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 listen to this episode to here the rest. Joseph Gerstel & Aaron Shapiro 

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 had a hardware product designed with no engineering background Great legal resources that can help you launch a company including Cooley Go and Y Combinator's free document resources  How Flaus pre-sold more than $300K of its electric flosser hero product on IndieGoGo Raising money from friends and family  What a SAFE is, and why it can be an attractive way to raise early capital  How Sam reflects on the risk she took leaving a high-paying job as a mid-level associate We had an awesome conversation with Sam and we hope you'll find her journey as inspiring as we do! Joseph & Aaron

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 is now Chief Revenue Officer.  In this episode we discuss:  How Alex made the move from corporate associate to Director of Strategic initiatives at Best Company The cultural and workstyle differences between legal practice at a large law firm and strategic work at a growing company How Alex thought about the risk of leaving his stable legal career  Alex's advice to law students on how to make the most of law school   Alex was a real pleasure to speak to and an awesome human being. Enjoy the convo! Joseph & Aaron 

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