Introduction: 0:00

• Introducing Chelsea Grayson, Managing Partner at Pivot > and former board member and CEO at major brands like American Apparel, True Religion, Spark Networks, and more.
• Currently serving as a board member at Beyond Meat and Xponential Fitness.
• Envisioning yourself as a “Philadelphia Lawyer” from a young age.
• Getting comfortable with reading and advocating for text as an English Literature major at UCLA.

Rising to partner at Jones Day and Loeb & Loeb, two big LA-based law firms: 3:00

• Investing in relationships and relying on mentors to guide you to options you didn’t know were available.
• Receiving guidance from a veteran lawyer who teaches you transactions after seeing beyond your self-conception as a litigator.
• Balancing agency over your own career with an understanding of power structures that extend to beyond CEOs.

Transition to in-house legal (and a CEO role) at American Apparel: 9:35

• Being recommended to an American Apparel board member to fill a GC role by a former client at CBS Corp.
• Accepting a 50% pay cut to help save an LA-based public company with more than 7,500 specialized employees working in the city.
• Firing the CEO for cause on her first day as GC.
• Combatting a hostile takeover, taking a poison pill, and building relationships with bondholders at Goldman Sachs during her first year.
• Reluctantly accepting a CEO role and figuring out the details later.

Tips for building relationships with investors: 15:11

• Demonstrating maturity and charisma so that people follow your leadership.
• Aligning with bondholders about retaining people, unifying teams, growth, and revenue.
• Considering a successor plan if the CEO needs to be replaced.

Managing CEO transitions: 18:34

• Planning out the replacement plan and keeping the current CEO looped in.
• Taking the process behind the scenes when the CEO doesn’t want to resign.
• Letting the CEO show their replacement around and make introductions for an amicable transition.
• Converting a young company’s entrepreneurial mentality into a professionalized environment.

Joining boards and positioning yourself as a good board member: 26:30

• Keeping your head in and your fingers out.
• Offering solutions when asked, being available, and always having an opinion.
• Tips for lawyers on how to join a board.

Becoming CEO of True Religion Jeans during a turnaround: 34:19

• Leading a company at the moment they come out of chapter 11.
• Converting from board member to CEO to bring a sense of consistency to a troubled company.

Sitting on the board of Sugarfina after a bankruptcy turnaround: 37:45

• Separating the board’s corporate restructuring work from the CEO’s operational mandate.
• Maintaining fiduciary obligations as a north star when winding down companies.

Stepping into a tech CEO role at Spark Networks: 42:00

• Spending five years on the board of the dating app giant.
• Needing a knowledgeable leader when the company is going private.
• Removing “interim” from your title to broadcast a sense of consistency.

Founding Pivot >, a corporate restructuring company: 47:39

• Bringing together restructuring professionals to create an advisory firm for companies wanting to manage or preempt a crisis.
• Serving on the board of Xponential Fitness and Beyond Meat.

Book recommendations: 55:08

• Quench Your Own Thirst: Business Lessons Learned Over a Beer or Two by Jim Koch
• The Messy Truth: How I Sold my Business for Millions but Almost Lost Myself by Alli Webb
• Shoe Dog by Phil Knight

What you wish you’d known as a young lawyer: 58:10

• Understanding that saying no to everything is a bad strategy.
• Leaning into the business needs of your clients.