For the last 35 years, I have worked with, advised, or mentored hundreds of people in leadership positions—from top executives at the largest global corporations in the world to founders of dozens of startups to the heads of various nonprofits.
In the context of organizational design, digital transformation, marketing, experiential design, and storytelling, I have had the good fortune to work with so many brilliant and inspiring CEOs, visionaries, and strategists whose large organizations were vibrant and exciting. Conversely, I’ve seen firsthand the insides of cultures where toxic leadership styles resulted in talent brain-drains and drudgery while billions of dollars were squandered because of cultural misalignments, innovation paralysis, and lost opportunity. I have also experienced this personally.
I have climbed my way up the hierarchies of both a large creative services company and a well-known hard goods manufacturer, and also as a leadership consultant and an agency partner charged with both consumer engagement and workforce motivation for Fortune 100 clients.
While some of this is endemic to large organizations, early-stage to midsize companies have their own unique leadership challenges as well. As an angel investor, GP and LP in various early-stage VC funds, and mentor for multiple accelerators, I’ve been an advisor to well over 150 startup founders, exposing me to a wild range of leadership styles and approaches.
All of these lessons and interactions—good and bad—were put into play as a founder or co-founder of successful agencies and consultancies, as well as a package goods company. My organizations were carefully designed around cultures of positivity, inspiration, inclusion, and performance. And my subsequent exits gave me the space and time to philanthropically co-direct a nonprofit organization deeply aligned with my values and, prior to that, serve as a chief advisor to another equally aligned and renowned nonprofit. And finally, I am a co-founder of a thriving global community for social entrepreneurs.
All of this is to say I have become a keen and astute observer of what works and does not work in leadership. I have seen the good, the bad, and the very ugly in organizations of all sizes. I myself have had extraordinary and rewarding partnerships, and I have had toxic ones that debilitated and depleted me.
Suffice it to say, like all of us, I continue to learn important lessons throughout my career. Yet through all of this, the most rewarding thing I have experienced is my own joy in advising and being a confidant to incredible leaders who go on to do great things for themselves, their organizations, and society writ large. And sometimes those great things are merely persevering through and surviving difficult times—or finding balance and flow while in a complex job inside a complex company inside a complex world.
