The Abstract

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-55

Topics:
Introduction: 0:00
Forging a career in highly regulated legal areas: 1:25
Advice to law students considering a JD-MBA: 7:20
Teaching yourself to become comfortable with uncertainty: 9:57
Leaving Remitly right before it went public to found a start-up: 15:10
Unpacking Upwardli: 18:42
Bringing your business to a start-up accelerator: 22:26
Fundraising for your start-up: 27:05
Making an effective pitch: 33:15
Growing into the CEO role: 36:16
Building Upwardli in Milwaukee, Wisconsin: 44:43
Bonus questions: 48:48
Book recommendations: 51:29
What you wish you’d known as a young lawyer: 53:02

Connect with us:
Aaron Gregory - https://www.linkedin.com/in/amgregory/
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 can C-suite leaders take on challenging political issues that affect their company? How do you pursue a path of professional growth at a company over the course of a decade? What's required for taking on wide-ranging responsibilities at the executive level?

Join Kristin Sverchek, President of Lyft, as she discusses how she joined a small start-up as their first general counsel and grew with it as it transformed into a global ride-sharing powerhouse with a multi-billion dollar IPO.

Listen as she discusses the unexpected management challenges she faced and conquered internally as her role expanded beyond legal, as well as the external challenges of taking strong stances to protect her drivers in the face of adverse political climates. She also offers advice for lawyers looking to expand beyond the legal function and shares stories about innovating in industries where regulations haven’t been updated in over a century.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-54

Topics:
Introduction: 0:00
Finding your way to Lyft: 3:51
Taking on your first GC role at Lyft: 6:23
Building a legal team at a rapidly growing start-up: 8:23
Helping lead the IPO process: 10:48
Comparing work at public and private companies: 14:39
Dealing with the challenges of executive roles: 17:20
Transitioning into the President of Business Affairs role: 21:45
Working with an executive coach during major career transitions: 26:08
Advice to lawyers who want to take on GC “plus” roles: 27:56
Defining and living your values at Lyft: 30:30
Taking on the role of President: 35:58
Departing Lyft: 38:42
Book recommendation: 45:52
What you wish you’d known as a young lawyer: 46:58

Connect with us:
Kristin Sverchek: https://www.linkedin.com/in/kristinsverchek/
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 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-53

Topics:
Introduction: 0:00
Attending law school in Washington, D.C.: 3:51
Working for a committee vs. working for a congressperson: 5:05
Questioning whether policy work requires a law degree: 7:12
Launching your own government relations firm: 10:17
Analyzing the evolving conversation around around tech in Washington: 13:15
Hiring your company’s first government relations consultant: 15:35
Joining and organizing coalitions and industry organizations: 20:58
Choosing who will represent your company in D.C.: 26:20
Avoiding common mistakes: 28:30
Envisioning the future of AI policy: 30:32
Advising companies during an election year: 34:42
Tracking the changing nature of lobbying: 36:09
Book recommendations: 38:14
Lobbying vs. government relations: 40:23
What you wish you’d known as a young lawyer: 42:47

Connect with us:
Matt Tanielian - https://www.linkedin.com/in/matttanielian/
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 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-52

Topics:
Introduction: 0:00
Becoming a top dealmaker at LiveRamp: 1:33
Moving quickly to close deals: 7:06
Offering operational solutions to small and medium businesses at Rippling: 10:08
Surviving the collapse of Silicon Valley Bank: 23:14
Collaborating with finance as a legal team: 36:21
Tips for a fast and low-fee financing deal-making process: 40:54
Favorite parts of day-to-day work: 41:54
Book recommendations: 44:22
What you wish you’d known as a young lawyer: 45:28

Connect 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-51

Topics:
Introduction: 0:00
Taking on the chief people officer role while serving as general counsel at Fetch: 2:25
The difference between CPOs and CHROs: 5:25
Encountering pushback from the executive team on HR policies: 9:01
Crafting culture within an executive team: 12:35
Establishing a comprehensive parental leave plan: 14:53
Approaching the hiring process as a CPO: 19:38
Comparing in-office policies against remote work: 24:40
Dealing with emotionally charged issues in the CPO/CHRO role: 30:57
Recommendations to GCs who want to take on multiple executive roles: 36:34
Considering the right candidate for dual GC and CPO roles: 42:39
Book recommendations: 46:37
What you wish you’d known as a young lawyer: 50:19

Connect with us:
Rachel Olchowka - https://www.linkedin.com/in/rachel-olchowka/
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 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: 12:23
Maintaining a positive attitude and setting a tone as a GC role: 18:05
Managing 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: 0:00
Moving into a tech advisor role at Gunderson Dettmer after a career start at Simpson Thacher: 2:11
Moving away from the standard legal path at Thompson Reuters: 5:38
Taking on side hustles that pull you towards tech and product: 8:43
Founding the Open Cap Table Coalition: 11:59
Rejoining Gunderson Dettmer and moving into the CIO role: 18:04
Challenging the billable hour model: 20:56
Leading and launching innovative projects: 30:06
Shifting from a legal to a technical mindset: 33:44
Discussing the influx of investment into legal tech: 37:20
Predicting the future of legal services: 41:06
Book Recommendations: 43:41
What 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: 6:01
Founding an aviation-focused law firm: 9:38
Learning to manage an executive team as a first-time GC at Skyryse: 11:47
Counseling an airline through the coronavirus pandemic: 14:57
Taking on a GC and First Officer role at Aero: 16:09
Leveraging your experience in the cockpit to lead as CEO: 23:59
Instilling confidence in investors as you transition from GC to CEO: 25:47
Inspiring teamwork in c-suite reports and hiring for your replacement GC: 30:58
Book Recommendations: 35:30
What you wish you’d known as a young lawyer: 38:49

Connect 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-46

Topics:
Introduction: 0:00
Rising to partner at Jones Day and Loeb & Loeb, two big LA-based law firms: 3:00
Transition to in-house legal (and a CEO role) at American Apparel: 9:35
Tips for building relationships with investors: 15:11
Managing CEO transitions: 18:34
Joining boards and positioning yourself as a good board member: 26:30
Becoming CEO of True Religion Jeans during a turnaround: 34:19
Sitting on the board of Sugarf ina after a bankruptcy turnaround: 37:45
Stepping into a tech CEO role at Spark Networks: 42:00
Founding Pivot >, a corporate restructuring company: 47:39
Book recommendations: 55:08
What you wish you’d known as a young lawyer: 58:10

Connect with us:
Chelsea Grayson: https://www.linkedin.com/in/chelseagrayson24/
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.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-46

Topics:
Introduction: 0:00
Deanna Papedis on adopting a strategic mindset and keeping your eye on the big picture: 1:05
Hardeep Singh on congratulating yourself when you reach a career milestone: 2:10
Vineet Shahani on dealing with career lows and leaning on your communication skills: 3:50
Nguyễn Vu on establishing strong relationships with people who can move the needle on your career: 6:09
Sagi Eliyahu on knowing when the world is ready for your idea: 8:49

Connect with us:
Deanna Papedis - https://www.linkedin.com/in/deanna-papedis/
Hardeep Singh - https://www.linkedin.com/in/hardeep-singh-863b1617/
Vineet Shahani - https://www.linkedin.com/in/vineetshahani
Nguyen Vu - https://www.linkedin.com/in/nguyentvu/  
Sagi Eliyahu - https://www.linkedin.com/in/eliyahusagi/  
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.