The Abstract

Can playing cards teach you to be a better lawyer? How do you make it in Silicon Valley without the traditional big law firm experience? And how do you make the jump to public company general counsel?Join Andrew Woods, General Counsel at PubMatic, as he discusses the unique path he forged from professional poker player to legal star. From founding a think tank at Harvard focused on poker and law to breaking into tech and privacy as Director of Legal and Associate Counsel at Twitter, Andrew relies on his belief in the value of autonomy, mastery, and significance to guide him towards work that makes him happiest.Listen as Andrew discusses his love for game theory, landing a fulfilling job leading legal at a tech company, hiring lawyers based on their ambitions instead of their experience, and more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-56Topics:Introduction: 0:00Starting your career as a professional poker player: 1:33Comparing poker skills with skills required to succeed as general counsel: 6:10Taking an unorthodox path after law school: 13:02Transitioning to in-house roles in tech: 17:12Moving away from skill questions in the hiring process: 22:52Developing mastery over fields like privacy and ad tech: 29:05Breaking into privacy: 33:18Considering the future of AI governance from a privacy perspective: 36:37Making the jump to Twitter and PubMatic: 39:21Book recommendations: 54:23What you wish you’d known as a young lawyer: 57:23Connect with us:Andrew Woods - https://www.linkedin.com/in/andrewmichaelwoods/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How do you make the leap from lawyer to founder? How do you craft the perfect pitch? What does it take to fundraise effectively? And how far will your legal know-how take you when you’re accountable for every function in the business?Join Aaron Gregory, Co-founder and CEO of Upwardli, as he shares his journey from general counsel to start-up leader. Starting his career in the highly regulated telecom and fintech industries, Aaron relied on lessons he learned while earning his JD-MBA to start a company that solves the challenges of credit invisibility for more than 50 million people in the United States.Listen as Aaron discusses how he took on the challenges that all first-time founders face–like pitching to VCs, fundraising, and growing into the CEO role—and shifted his mindset from that of a risk-conscious legal leader to a business-focused operator.Read detailed summary:  https://www.spotdraft.com/podcast/episode-55Topics:Introduction: 0:00Forging a career in highly regulated legal areas: 1:25Advice to law students considering a JD-MBA: 7:20Teaching yourself to become comfortable with uncertainty: 9:57Leaving Remitly right before it went public to found a start-up: 15:10Unpacking Upwardli: 18:42Bringing your business to a start-up accelerator: 22:26Fundraising for your start-up: 27:05Making an effective pitch: 33:15Growing into the CEO role: 36:16Building Upwardli in Milwaukee, Wisconsin: 44:43Bonus questions: 48:48Book recommendations: 51:29What you wish you’d known as a young lawyer: 53:02Connect with us:Aaron Gregory - https://www.linkedin.com/in/amgregory/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

Kristin Sverchek, President of Lyft, began her journey as the company's first general counsel and navigated a remarkable path to leadership. She shares insights on managing the complexities of a rapidly growing startup and the challenges faced while transitioning into a public company. Kristin discusses how she tackled political issues to protect drivers and offers valuable advice for lawyers aspiring to expand their roles. She reflects on the importance of mentorship and embracing change in a dynamic corporate environment.

What do you need to know if you're ready to launch a government affairs strategy? How do you find the right lobbyist? And how has lobbying for tech companies changed over the last decade?Join Matt Tanielian, Co-founder of Franklin Square Group, a bipartisan government relations, as he shares key insights from his decades of experience advocating for tech companies and bridging the gap between Silicon Valley and Washington. D.C. From advising senators on foundation internet legislation like the Digital Millennium Copyright Act and the Microsoft antitrust investigation, to lobbying for Apple as it launched its first iPhone in 2008, Matt has been instrumental to tech firms as they navigate the intricacies of Capitol Hill.Listen as Matt discusses how to work with politicians and government relations consultants, the value of joining coalitions and trade associations, the future of AI policy, and much more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-53Topics:Introduction: 0:00Attending law school in Washington, D.C.: 3:51Working for a committee vs. working for a congressperson: 5:05Questioning whether policy work requires a law degree: 7:12Launching your own government relations firm: 10:17Analyzing the evolving conversation around around tech in Washington: 13:15Hiring your company’s first government relations consultant: 15:35Joining and organizing coalitions and industry organizations: 20:58Choosing who will represent your company in D.C.: 26:20Avoiding common mistakes: 28:30Envisioning the future of AI policy: 30:32Advising companies during an election year: 34:42Tracking the changing nature of lobbying: 36:09Book recommendations: 38:14Lobbying vs. government relations: 40:23What you wish you’d known as a young lawyer: 42:47Connect with us:Matt Tanielian - https://www.linkedin.com/in/matttanielian/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How do you raise nine figures in financing in twelve hours as the first Twitter-fueled bank run is happening around you and you feel the pressure of hundreds and thousands of employees depending on your ability to finish the deal so their paychecks clear?Join Vanessa Wu, GC at Rippling, as she relives the moment her company overcame the disastrous collapse of Silicon Valley Bank and pulled through some lightning-fast deals to protect the income of the clients whose paychecks depend on them. Her department’s hard work turned a catastrophe into a boon to their company’s reputation, both with product users and investors.Listen as Vanessa offers a masterclass in getting financing and deals over the finish line in record time, with tips on moving through the diligence process, keeping fees low, and why it's essential for lawyers to close as quickly as possible.Read detailed summary:  https://www.spotdraft.com/podcast/episode-52Topics: Introduction: 0:00Becoming a top dealmaker at LiveRamp: 1:33Moving quickly to close deals: 7:06Offering operational solutions to small and medium businesses at Rippling: 10:08Surviving the collapse of Silicon Valley Bank: 23:14Collaborating with finance as a legal team: 36:21Tips for a fast and low-fee financing deal-making process: 40:54Favorite parts of day-to-day work: 41:54Book recommendations: 44:22What you wish you’d known as a young lawyer: 45:28Connect with us: Vanessa Wu: https://www.linkedin.com/in/vanessa-wu-7363359/  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.

What do you need to know if you're considering taking on the people function? What's the difference between a chief people officer and a CHRO? And are GCs well-positioned to take on both of these roles simultaneously?Rachel Olchowka, Former Chief People Officer and General Counsel at Fetch and current Chief Administrative Officer at Prizm Insurance, had no hesitations when she volunteered to operate a complex, metrics-driven people function in addition to her responsibilities leading in-house legal at a fast-paced organization. Not only did she learn how to do both roles—she learned how to do them well.Listen as Rachel shares how she was able to find balance between two very different executive positions, know whether expanding into a people role is right for you, establish a game-changing comprehensive parental leave plan, craft culture within a company and executive team, and more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-51Topics:Introduction: 0:00Taking on the chief people officer role while serving as general counsel at Fetch: 2:25The difference between CPOs and CHROs: 5:25Encountering pushback from the executive team on HR policies: 9:01Crafting culture within an executive team: 12:35Establishing a comprehensive parental leave plan: 14:53Approaching the hiring process as a CPO: 19:38Comparing in-office policies against remote work: 24:40Dealing with emotionally charged issues in the CPO/CHRO role: 30:57Recommendations to GCs who want to take on multiple executive roles: 36:34Considering the right candidate for dual GC and CPO roles: 42:39Book recommendations: 46:37What you wish you’d known as a young lawyer: 50:19Connect with us:Rachel Olchowka - https://www.linkedin.com/in/rachel-olchowka/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How do you help CEOs transition out of the business? How do you project calm in a time of crisis? Can you draw on the experience of beating cancer twice as you navigate the challenges of executive leadership?  Dan Haley, General Counsel and Corporate Secretary at Guild, has led a career spanning the world of local Massachusetts politics, leading legal at companies like Sprinklr, and Athenahealth, enduring cancer treatments while holding high-stress leadership positions, and becoming known as legal’s most “zen” GC.  Listen as Dan shares how he developed his calming professional philosophy, why he wears t-shirts to work, and how he instills and nurtures a sense of confidence in his staff during trying times.  Read detailed summary:  https://www.spotdraft.com/podcast/episode-50   Topics: Introduction: 0:00 Balancing cancer treatment with a high-stress job: 9:21 Building a reputation as a zen lawyer: 12:23Maintaining a positive attitude and setting a tone as a GC role: 18:05Managing CEO transitions in a time of crisis: 23:16 Enduring a hostile takeover from Elliott Management at Athenahealth: 27:31 Facilitating the CEO transition at Athenahealth: 32:52 Facilitating the CEO transition at Guild: 37:22 Book recommendations: 46:14 What you wish you’d known as a young lawyer: 50:13  Connect with us:  Dan Haley - https://www.linkedin.com/in/danhaley1972/  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.

How is AI going to change the practice of law? How is one of the most forward looking law firms adapting? And will the billable hour go away?  Joe Green, Chief Innovation Officer at Gunderson Dettmer and Cofounder & Director of the Open Cap Table Coalition, steered a law career starting at major Wall Street firm Simpson Thacher towards the worlds of tech and product management, with stop-offs in academia and legal publishing along the way. Ultimately, he found that his legal mindset guided him in his technical work, and his understanding of business and innovation strengthened his legal abilities.  Listen as Joe discusses strategies to shift your careers towards your passion through pro bono work, stepping into board advisory roles, parsing the influx of investment into legal tech, and whether the billable hour will really go away in our lifetime.  Read detailed summary:  https://www.spotdraft.com/podcast/episode-49   Topics: Introduction: 0:00Moving into a tech advisor role at Gunderson Dettmer after a career start at Simpson Thacher: 2:11Moving away from the standard legal path at Thompson Reuters: 5:38Taking on side hustles that pull you towards tech and product: 8:43Founding the Open Cap Table Coalition: 11:59Rejoining Gunderson Dettmer and moving into the CIO role: 18:04Challenging the billable hour model: 20:56Leading and launching innovative projects: 30:06Shifting from a legal to a technical mindset: 33:44Discussing the influx of investment into legal tech: 37:20Predicting the future of legal services: 41:06Book Recommendations: 43:41What you wish you’d known as a young lawyer: 45:40 Connect with us: Joe Green - https://www.linkedin.com/in/joegreen1/  Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft   SpotDraft is a leading CLM platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How do you build a legal and business career from a passion for aviation? What is the transition like from the GC role to that of CEO? And what is it like to run an airline?  Ben Klein, CEO and First Officer at Aero, was able to combine his dedication to legal work with his lifelong love of flying. Starting off at big law firms like Davis Polk & Wardwell, he successfully transitioned into aviation law after founding his own firm, then took on GC roles at autonomous helicopter start-up Skyryse and Aero, an airline offering a private-jet-like experience.   Listen as Ben discusses instilling confidence in investors during a CEO transition, counseling his airline through the coronavirus pandemic, and leveraging his experience in the cockpit to make his company the best it can be.  Read detailed summary:  https://www.spotdraft.com/podcast/episode-48   Topics: Introduction: 0:00  Transitioning from corporate law to aviation law: 6:01Founding an aviation-focused law firm: 9:38Learning to manage an executive team as a first-time GC at Skyryse: 11:47Counseling an airline through the coronavirus pandemic: 14:57Taking on a GC and First Officer role at Aero: 16:09Leveraging your experience in the cockpit to lead as CEO: 23:59Instilling confidence in investors as you transition from GC to CEO: 25:47Inspiring teamwork in c-suite reports and hiring for your replacement GC: 30:58Book Recommendations: 35:30What you wish you’d known as a young lawyer: 38:49Connect with us: Ben Klein - https://www.linkedin.com/in/ben-klein-01b8736/  Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft  SpotDraft is a leading CLM platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How do you build trust with investors who tap you for the CEO role? How do you prepare yourself to lead companies through some of their toughest moments, including bankruptcy, and guide other companies through their transformations as a board member?Chelsea Grayson, managing partner of corporate restructuring at Pivot > and former CEO and board member of brands like American Apparel, True Religion, and Spark Networks, has steered many ships through rough waters, including post-chapter 11 turnarounds, corporate wind-downs, and firing CEOs for cause. She has transitioned from board member to operator and back again, and is currently sharing her expertise on the boards of Xponential Fitness and Beyond Meat.Listen as Chelsea discusses her legendary journey from law firm partner to GC, CEO, Board Member, and now managing partner of an all-star corporate restructuring company, and offers tips to lawyers who are looking to find a board seat.Read detailed summary:  https://www.spotdraft.com/podcast/episode-46Topics:Introduction: 0:00Rising to partner at Jones Day and Loeb & Loeb, two big LA-based law firms: 3:00Transition to in-house legal (and a CEO role) at American Apparel: 9:35Tips for building relationships with investors: 15:11Managing CEO transitions: 18:34Joining boards and positioning yourself as a good board member: 26:30Becoming CEO of True Religion Jeans during a turnaround: 34:19Sitting on the board of Sugarf ina after a bankruptcy turnaround: 37:45Stepping into a tech CEO role at Spark Networks: 42:00Founding Pivot >, a corporate restructuring company: 47:39Book recommendations: 55:08What you wish you’d known as a young lawyer: 58:10Connect with us:Chelsea Grayson: https://www.linkedin.com/in/chelseagrayson24/Tyler Finn: https://www.linkedin.com/in/tylerhfinnSpotDraft: https://www.linkedin.com/company/spotdraftSpotDraft is a leading CLM platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.