FounderForward Turns 5: Reflecting on 5 Years of Coaching Startup Leaders

Five years ago this month, I officially launched my coaching and development company, FounderForward. After the launch, I set out on a networking tour to tell everyone I knew about what I was up to and why. While a handful of folks got it, most had hesitant looks on their faces. Among the most common questions I fielded:

“Do you think startups/founders will allocate money for coaching?”

“Are startup leaders really going to have time for this?”

“Why would a founder use a coach when they have advisors and VCs?”

Having spent nearly 20 years in startups at that point — as both an operator and a VC, I had come to believe that the human side of startups was far more complex than any product or technology. And founders certainly didn’t want to discuss the messy human stuff — like imposter syndrome or co-founder fighting or the emotional toll company-building was having on them — with their investors. My work with a coach started to seep into my conversations with portfolio company founders. Slowly but surely, I began to sense that my mission was to serve founders in a different way than check-writing. I wanted to partner with them as they intentionally sought to grow themselves alongside their businesses and to show up as the best leaders they could be.

Cut to today, where thankfully coaching is quite commonplace in the startup world. Coaching is no longer a weakness or something to do but not discuss, it is a “wiseness” that leaders are embracing and, for the most part, are pretty comfortable talking about. Thank you, Jerry Colonna, Ed Batista, Bill Campbell, and other early tech/startup coaches.

As I look back over the last 5 years, they are some of the most fulfilling of my life. Growth is a core value I hold and the coaching profession allows me to live deeply aligned with this value daily. I have worked with hundreds of startup leaders through 1–1 coaching, group coaching, and leadership training and workshops. It is truly a privilege to spend my days working with leaders that are “in the arena” and doing the work to transform themselves into the best leaders (and humans) they can be. From and with these clients, I learn and grow daily.

I have dedicated time these past several weekends to reflect upon my coaching. I’ve reviewed the countless journals, notes, and binders I have accumulated over the last five years. In honor of FounderForward’s 5th birthday, I wanted to share 5 things about leadership and leadership development that I have learned to be true.

1.) Leadership starts with SELF. So many founders I speak with on an initial call are eager to scale themselves alongside their businesses by learning how to be a better leader or manager of others. They want to dive right into the “what and how” because startups move fast and they need competencies and tools NOW. Yet coaching starts with WHO, and requires slowing down and getting honest and vulnerable about how you are showing up — the ways you think, feel, and act. This can include (re)assessing values, committing to better self-care, and improving emotional intelligence, among other work. What I know for sure is that leadership is an inside game and the best leaders of others are great leaders of self.

2.) Leadership is a practice (not a position). Mastery at anything requires intention and commitment coupled with constant and steady repetition. The most high-performing leaders I work with are diligent about creating, reflecting upon, and revising their leadership and personal growth goals as well as their daily practices and routines. As part of this, they approach mental and emotional fitness with the same dedication and patience they do physical fitness.

3.) Leadership is as much about psychology as it is about business.
In the early stages of working with most of my clients, it becomes clear that they are often their own biggest obstacle (see #1 above). This is in large part due to what’s going on in their heads. Coaching can bring so much value here, as reflective inquiry helps clients see their ways of thinking — negative thought patterns, assumptions, limiting beliefs, etc. From this new awareness comes the opportunity to embrace new perspectives and ways of being and to let go of existing thoughts, feelings, and behaviors that are no longer useful.

What I have also observed is that the more work leaders do to understand their own inner-workings, the more curious and insightful they become about the thoughts, feelings, and behaviors of others. Through the lens of psychology, they hone their people and management skills, including relationship-building, collaboration, motivating and coaching employees, conflict management, and more.

4.) The less leaders NEED to be successful, the more successful they will be. Yes, this is quite the paradox. I have worked with countless founders whose identities are completely tied to their startups. When the startup is good, they are good. When the inevitable “bad” thing happens (lose an employee or customer, get a “no” from a VC) they take it very personally. I understand this and this is how I operated when I was a builder. When we embrace ourselves for all of who we are and not just what we do, we can lead (and live) from a place of trust, optimism, and courage, rather than worry and fear. This takes deep work to unlearn and surrender to but it is magic when it happens.

5.) PRESENCE is foundational to exceptional leadership. Borrowing from the definition by the great Doug Silsbee, author of Presence-based Coaching, “Presence is an inner state of awareness, in this very moment… characterized by a deep openness and connectedness where you are who you fully are and are maximally resourceful and responsive to what the circumstances require.” From Presence comes so many things — self-awareness (of mind, feelings, and body), active listening, and (co) creativity, to name just a few.

Practicing and cultivating Presence is work that will pay off exponentially across all aspects of leadership and life. Particularly in a world where extreme VUCA (Volatility, Uncertainty, Complexity, and Ambiguity) seems to be the new normal, Presence is for sure the most resourceful ground from which to navigate.

What I also know to be true is that “the work” of self-actualization is a lifelong pursuit. I truly feel so lucky to have chosen a profession that provides my own laboratory for self-cultivation, while allowing me to serve passionate entrepreneurs in pursuit of solving problems and making an impact on the world.

I have spent a good deal of time these past five years studying neuroscience and psychology. I also co-taught a class at USC called Performance Mindset for Business. Currently, I am participating in a Positive Intelligence training program and a Coaches Rising Power of Presence course. Both are already adding rich layers to my work with clients.

The next frontier for me is to focus my learning and work on improving my somatic awareness and becoming more embodied. As a coach, I want to more fully bring a feeling-awareness to my body so that I can most effectively hold the space and energy for emergent work. I am committed to the journey of becoming more deeply connected and attuned with myself, as well as with others and nature.

I would not be the coach I am today without the support of so many. Special thanks to Anna Barber, Janine Davis, and Cheri Schappert for being great friends and great coaches, my Positive Intelligence Pod Jenny Banner, Jonathan Basker, Andy Sparks and Steve Schlafman, my Coaching Circle Crew Bryan Wang, Micah Baldwin, Steve Schlafman, Mindy Zhang, Laura Guzman, and Ryan Vaughn. Last but not least, thank you to my son, Ryder, who has become my greatest teacher.