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Ep 75: Must-Read Books for Legal Professionals in 2025 | Bonus Episode
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What are the top books that every legal leader needs to read to succeed in the new year?
At the close of each episode, Tyler asks our guests what book they would recommend to our audience, and we’re kicking off 2025 with this year’s list of must-read books that you need to check out. Listen to hear titles that these CEOs, start-up founders, and GCs can’t live without.
Read detailed summary: https://www.spotdraft.com/podcast/episode-75
Topics:
Introduction: 0:00
Joe Green, Chief Innovation Officer Gunderson Dettmer, recommends Leading Professionals: Power, Politics, and Prima Donnas by Laura Empson: 0:42
Rachel Olchowka, General Counsel & Chief People Officer at Fetch recommends Powerful: Building a Culture of Freedom and Responsibility by Patty McCord: 1:34
Dan Haley, General Counsel at Guild Education recommends Helping Your Business Win by Gene Kim, Kevin Behr, George Spafford: 2:39
Chelsea Grayson, Managing Partner at Pivot, recommends Quench Your Own Thirst: Business Lessons Learned Over a Beer or Two by Jim Koch: 5:51
Aaron Gregory, CEO of Upwardly, recommends The Right It: Why So Many Ideas Fail and How to Make Sure Yours Succeed by Alberto Savoia: 7:38
Jasmine Singh, General Counsel at Ironclad, recommends The Practice of Groundedness: A Transformative Path to Success That Feeds--Not Crushes--Your Soul by Brad Stulberg: 10:03
Sean West, Co-Founder of Hence Technologies, recommends The Coming Wave: Technology, Power, and the Twenty-first Century's Greatest Dilemma by Michael Bhaskar and Mustafa Suleyman: 12:56
Jules Polonetsky, CEO of Future of Privacy, recommends: Privacy Is Hard and Seven Other Myths by JH Hoepman: 14:17
Heath Tarbert, Chief Legal Officer at Circle, recommends The Enchiridion of Epictetus: 14:57
Matt Tanielian, Co-Founder of Franklin Square Group, recommends How to Talk Dirty and Influence People: An Autobiography by Lenny Bruce: 16:21
Connect with us:
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
SpotDraft - https://www.linkedin.com/company/spotdraft
SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.
Visit https://www.spotdraft.com to learn more.
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Transcript
Introduction and Format Explanation
00:00:00
Speaker
As you all know by now, I love to read, and I'm always looking for book recommendations. So at the end of every episode of the abstract, I ask my guests to recommend a book, or two, or three.
00:00:12
Speaker
These could be about legal or privacy, could be a business book, but it doesn't have to be. Could be something totally unrelated to their day-to-day. Fantasy or historical fiction, you name it, I want to hear about it. So today, for this special bonus episode of The Abstract, we're recapping some of my favorite recommendations from guests throughout 2024.
Book Recommendations from Various Fields
00:00:42
Speaker
Let's start today with some books that focus on leadership. The first recommendation comes from Joe Green, Chief Innovation Officer at Gundersen Detmer. I actually just finished writing another book chapter yeah about you know kind of big law business strategy and and management where I read thousands of pages and multiple books, you know, kind of on that topic. And one of my favorites from that is from a a professor named Laura Empson in the UK, she wrote a book called Leading Professionals, Power, Politics and Primadonnas. It's quite excellent. It's given me a lot of food for thought. And, you know, I highly recommend that one to anybody who's, ah you know, kind of in in the in the law firm world and wanting a better understanding of you know kind of what makes what makes law firms tick and why they work the way that they do, and and some of the benefits of that partnership model. Next, we'll hear from former Fetch General Counsel and Chief People Officer Rachel Ochoka with her choice from a former Netflix Chief Talent Officer.
00:01:45
Speaker
As a person really focused on people and culture and building that in a business, Patty McCord was Netflix's CHRO. Netflix has this amazing culture. Their culture deck is available publicly. And Patty McCord wrote a book called Powerful, Building a Culture of Freedom and Responsibility that is unequivocally the best book I have ever read about culture. It's not too tactical. It's not too focused on The KPI is the metrics, the operational rigor. Everything is more about creating an environment where folks are able to do their best work, be creative, be free, because they feel trusted. So Powerful is absolutely one of my favorite books. We ran a leadership development cohort-based course, essentially, for folks on the cusp of leadership. And we gave copies of that book out at the end of a couple of the cohorts. It is a really exceptional book, and it's short and an easy read.
Business and IT Insights
00:02:39
Speaker
Let's hear what Dan Haley, the Zen General Counsel at Guild Education, has to share about supercharging your business outcomes. my head of inossak asked me to read a book called the phoenix project which is it's a novel But it's also um the genesis of what in the tech community is called the DevOps revolution. It's a way of doing product development within a technology company, a framework and a set of methodologies.
00:03:11
Speaker
that is now tremendously widespread. And it yeah it's Genesis in this novel called the Phoenix Project about an automotive parts manufacturer manufacturer and how they transition from legacy IT t to a new way of doing things that revolution or revolution their business. And that sounds so uninteresting. and when she And she laid that out for me. I was like, uh-huh, yeah, i'll I'll definitely put it on the list. oh And then i was I was riding my bike and listening to a podcast and my my data stream got fussy or something went wrong with Apple Podcasts or something and it stopped working and I stopped and I was aggravated. And I just, I looked in Audible audiobooks and I looked up the Phoenix Project and I was like, I i should give this at least a few minutes and i'll I'll listen to it on, you know, two times speed and whatever.
00:04:02
Speaker
I started listening to this thing, and um you know four days later, I finished it, having listened to it at every opportunity. um It's funny. i mean it's like it's not a particularly like The characters are very cardboard. They're corporate stereotypes. A tight-ass chief compliance officer who gets in the way of everything and then has an evolution, and you've got the demanding CEO who just doesn't understand what the IT t folks do and it's cardboard. But for anyone who's worked in the bowels of a tech company, there's so many things that resonate. And I just kept having moments of Oh, I didn't understand that or
00:04:42
Speaker
minor things, like, oh, that's what that acronym means. Or, you know, that's what that terminology, that's, you know, when you do that to me all the time, and I just let it flex right through my head. And so I've now, for the first time in my career, committed the sin of saying to my whole team, I'm going to require you to read this book, and we're going to have a conversation about it next month. um It drives me crazy when like people do that. Like, I love this book, and now you must read it. I'm requiring it.
00:05:09
Speaker
Yeah, that's annoying. And I'm doing it because it gave me insight into, tremendous insight into how a very crucial portion of our business and frankly any modern business works.
00:05:24
Speaker
that if you haven't been inside of it, you don't understand it. And understanding it will help me be a better GC for my business and will help my team give better advice, be better collaborators, be more proactive. um and I've got a high degree of confidence around the notion that people will, if not thank me, at least the people that wasn't raised to their time. yeah um So yeah, long long answer to a short question, Tyler.
Unconventional Business Wisdom
00:05:52
Speaker
There are some business lessons you can only learn through the experiences of great business leaders who are sharing their own hard-earned stories. Take a page from Chelsea Grayson, former CEO at American Apparel and True Religion.
00:06:09
Speaker
So actually, I'm terrible at remembering the names of books, but I can tell you that. So Jim Cook, okay, actually, I'm looking at my bookshelf and I can tell you what the name of it is. So Jim Cook wrote a book called, Quench Your Own Thirst. Jim Cook is actually one of my colleagues on the Beyond Meat Board. He was the founder and CEO of Boston Brewing Company, which is the Sam Adams Company. ah huh If you're a beer drinker, you know. a Great beer, yeah.
00:06:38
Speaker
was popular. I mean, they basically almost created the micro brewing industry in in America and they like actual good tasting beer to them like American made good tasting beer here and realized that even the beer that the Germans were importing here wasn't great. Cause you have to actually go to Germany to get good German beers. So I actually sent to Sam Adams. So Jim cook wrote this book called punch your own thirst, which I read once I was appointed or once I was nominated to the board. Cause I just, I don't know. I wanted to have something to talk to him about. Have a second to know him a little bit. and It was actually a great book. It was, he's really um irreverent, you know, in the way that he provides friends. He's kind of a,
00:07:18
Speaker
you know, sort of a, um, kind of a cat. I don't know how else to say it, you know, but like kind of gritty anecdotes to tell, which is sort of shocking. What I thought I was reading and I sort of thought it was going to be a stodgy business advice book and it wasn't at all. So it was a really fun read, really quick read. You know, you can read it over a weekend on a plane. Like you said, does your business idea have what it takes to be the next big thing?
Startup Strategies and Problem Solving
00:07:42
Speaker
Check out this fascinating book recommended by upwardly founder, Aaron Gregory.
00:07:48
Speaker
For those who are interested in startups, the right it, which is about like, how do you figure out, like you come in, you come into the world with like a problem statement about like, I think the world, like this is a problem. And you said, I saw it from like the founding story, like here's the problem statement, but the solution is actually probably something that is not in your head because you have a idea what the solution should be. And then you go and take it into the world and they're like, actually that doesn't resonate with me at all.
00:08:14
Speaker
And you don't want to build products like that, right? And so the right it is about how you get to a solution to a problem that people actually want and will pay for quickly with limited resources. And so I recommend that to anyone who's in startup world, because I think that's the mentality you have to have to get to to figure out that zero to one journey is all about. Predotyping and prototyping your way into product market fit before you go and build the month. the big monster optimize machine you know
00:08:47
Speaker
Hey there, legal teams! Big news! Spotdraft's fall release is here, and it's our biggest update yet. With over 15 new features, it's packed with tools to make contracting faster and simpler for you.
00:09:00
Speaker
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00:09:29
Speaker
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00:09:57
Speaker
Now let's get back to the podcast.
Inspiration Beyond Material Success
00:10:03
Speaker
Chief legal officer Jasmine Singh knows how challenging it can be to make a big career transition. She took a break from being a litigator to become a spin instructor before returning to the world of law. Here's a book she recommends to help people with their own career journeys.
00:10:24
Speaker
There's this book called A Practice of Groundedness. um And there was like some some title about like the transformative path to success that doesn't crush your soul or so something like that, but it sounds so lofty. I read that book for the first time when I was feeling a little stuck and when I was sort of like, ah you know i I don't know what to do and I don't know how to get unstuck or I don't know how to get to the next level. um But I actually revisit the book often when I find myself in in spirals around What does success mean? What does it mean to be successful? And what does it mean to be on this sort of like hamster wheel of success? And you know, I'm actually like, I'm i'm reflecting in what I said earlier about like, oh, I care too much about success. I'm like mortified that I said that because ah for me, it's success is actually not wanting for more. Whether you're
00:11:15
Speaker
a lawyer or a spin instructor or whatever. right like The most successful people to me are those that are satisfied with their life right as it is and how how it is. and Sometimes I come back to this book and I need to remind myself that like constantly wanting for something different So, constantly wanting for something more erodes my sense of happiness. And you know, there are lots of studies that say this is true for other people, but i I won't be too prescriptive and say that's true for everyone, but I know it's true for myself. yeah And this book is a really good reminder for me. And I have, you know, it's tabbed and highlighted in places where I go back and read it. And it reminds me like,
00:11:55
Speaker
I, to be more present in what I am and to be satisfied in living a really fun journey and not constantly trying to exceed succeed and get to the next level and get to the next thing and, you know, check off that box. That's going to give me a sense of accomplishment, and you know, the serotonin that comes along with like, Oh, check this off now. I'm done. Oh, check this off. Right. Like I very intentionally not trying to live that life because.
00:12:23
Speaker
I think it really can take away from current state happiness and it can really undermine the joy that can come in like the most regular things, right? like The beauty of the world, like waking up every day and seeing the most incredible flowers on my walk to my son in school. like I don't ever want to lose sight of the fact that like I am very happy and lucky to have a life where I get to do that. um And this book in particular is a nice reminder of how to live a life that allows for that.
Technology, AI, and Society
00:12:56
Speaker
Let's turn now to books about how technology is influencing the world around us. Many of us are concerned about topics like AI or privacy and data protection. Here are a couple of recommendations about the world that tech is building around us right now, starting with one from Hence Technologies co-founder Sean West.
00:13:19
Speaker
The Coming Wave by Mustafa Solomon, who's now yeah um head of AI at Microsoft, was one of the founders of DeepMind. It's just a phenomenal book. If you want to very quickly get spun up on the societal ramifications of everything that everyone in the AI and tech world is talking about, that book is inspirational. It's very good. I mean, you and I, we see each other at like millions of legal tech conferences a year. yeah I think what people need more of is just that kind of societal window into like What does this all mean? Because we're all furiously trying to increase our productivity using amazing tools like hens or spot draft or whatever. But like all of these tools actually are existing in a bigger ecosystem of rules and laws and they're affecting rules and laws. And I think that that book was part of the inspiration for me to write mine because I read it and I thought like we need to go much deeper on the politics of this and yeah think about it um and connect it into the legal sector and understand the implications as well.
00:14:17
Speaker
There aren't many people out there who understand the intricacies of privacy better than Jules Polonetsky. Here's what the Future of Privacy Forum CEO says you need to read about this important topic.
00:14:31
Speaker
um the best privacy by design book is one by a presser named yak he Oh, the beginning is the last name, but a Dutch academic, um and it's it's called something like, seven you know, privacy is hard and and seven myths. And it really walks you through a number of scenarios and sort of analyzes um what went wrong and what you could do about it.
00:14:54
Speaker
um That's ah another book that I really um appreciate.
Philosophy and Practical Guidance
00:14:58
Speaker
Heath Tarbert, Chief Legal Officer at Circle, may have one of the more intriguing recommendations in the history of the podcast in ancient Greek philosophical text from the second century. Let's hear a little more.
00:15:12
Speaker
If I could take one book to a desert island, what would it be? I would say some of the best books are the old books. And one book I'd recommend, and I'm not sure how many people have read it because it's somewhat obscure, is called The Incoridian by Epitetus.
00:15:29
Speaker
ah You're probably like, what the hell is that? Well, Epitetus was a great stoic philosopher. And many people have heard of the Meditations of Marcus Aurelius. Have you heard of that one? Right. and So that's on reading lists. That's people and that is a great book.
00:15:44
Speaker
But Marcus Aurelius actually learned from Epitetus. So he read Epitetus first, and the Incoridian is a small book, and I think it's probably the best synthesis of Stoic philosophy, and it is a um it's called the Incoridian, which translates into handbook, or ready at hand.
00:16:02
Speaker
So it's like you could take one book and have it ready at hand to navigate life. It would be this. And so the version that I would recommend, there's a new one out by Princeton University Press, and it's called How to Be Free. And it is a translation of Epitetus in Caridian. So I would recommend that book.
Entertainment and Free Speech Insights
00:16:22
Speaker
Now, let's end this episode with a fun one. No legal or business acumen to share here, just the observations and stories of a controversial and groundbreaking comedy legend recommended by Franklin Square Group co-founder Matt Tennelian.
00:16:43
Speaker
The book that I just finished is the autobiography of ah Lenny Bruce. It's called How to Talk Dirty and Influence People. I just thought it was sort of like the most lobbyist thing i could I could possibly do. It is also an excellent law book. Lenny Bruce was arrested a lot.
00:17:02
Speaker
um And as a First Amendment ah sort of, it's not exactly a legal treatise, but but it is incredibly entertaining and to hear him describe his arrests for for all sorts of lewd activities that he participated in, um at least at the time. Today they would seem like, you know, mild close to illegal.
00:17:28
Speaker
um was was quite the interesting law books. So for all the lawyers listening, I'd recommend go go read Lenny Bruce's auto autobiography. It is quite entertaining and a good legal read. That's all for now. Thanks so much for tuning in. Happy New Year and check back each week for more great book recommendations with each new episode of The Abstract.