The Hardest and Most Important Change You Can Make as a CEO

Tears rolled down my face. I walked down Sandhill Road next to the famous venture capitalist who only days earlier had handed me a generous term sheet. Now, I was telling her my life was falling apart and explaining why she’d likely want to pull the term sheet and work with someone else. My voice quivered as I tried to explain what had happened.

A VC Meeting Ruined?

I was on a coaching call this week with an incredibly talented and accomplished founder/CEO. She was frustrated because she’d met the day before with a well-known venture capitalist who’d told her “Your business is really interesting, but I feel like I’m having a hard time getting a real read on you. You're very polished, but I don’t feel like I’m getting the real you here.” She read this as a pass and a failure on her part, and I disagreed.

Having been through hundreds of VC meetings in the last 7 years, and remembering back to the first time I met with many of these famous Silicon Valley investors for the first time, I know first-hand how soul-crushing any negative feedback can be. This feedback felt especially personal, this founder was feeling it acutely still, a day later, on our coaching call.

She felt she’d ruined the meeting. I assured her she hadn’t.
On the contrary, I assured her, what was happening I believed was that this investor saw something in her. And he wanted to see more.  He wanted to see beyond the perfect answers, the command of the business and the industry, the honed pitch…he wanted to see her.

My own masked dropped out of necessity

During my first several years as a venture-backed CEO, I found myself wearing my own mask. Each day, as I entered the office, I can remember thinking that I needed to steel myself for the task at hand. I believed I needed to be the one with all the answers. I needed to be the confident, unshakable leader. A stalwart for the team when things were hard.

This was not my first time in such a role. In my family, growing up, that was my place. My dad was a big-hearted man but addicted to alcohol and prone to emotional hurricanes. My mom and sister often looked to me to be the stable, unflappable one during my father’s frequent rages. I took on the role of being the stable one in the family. The glue that held the little tribe together on the worst days.

This ability to stay cool, collected, and confident in the midst of turmoil became a superpower for me. And it served me extremely well. On sports teams, I was the leader who could rally the group after a painful loss or a coach’s outburst. Later in life, as we were getting the company off the ground, cofounders and early employees turned to me when they felt overwhelmed by the confusion and uncertainty of early startup life.

But soon thereafter, I hit a wall where I could wear the mask no more.
The wall came in January of 2014. We were preparing the company for our Series A. The business, which had previously been known as Instacanvas, had totally flatlined in the last year. We’d seen early success with our ‘print your Instagram photos on wall canvases’ business. But the business had grown to ~ $1M in revenue then flatlined. We’d raised a couple million in financing but were quickly running out of cash. As of January, we had less than 90 days of cash in the bank.

It was a Sunday night. My birthday. I’d been in bed all weekend with the stomach flu. You can’t make this shit up.

My (now ex) wife asked if I could make it out of bed for a short walk. I replied, “I’m not up for a party.” She said it wasn’t for a party, that we needed to talk.
She proceeded on the walk to tell me that our second son, four weeks old at the time, wasn’t mine. That she’d had an affair.

I couldn’t think. I couldn’t talk. I needed to get out, away, someplace else. Someplace safe. I called my best friend and co-founder Todd. Freaking him the fuck out, I simply said, “Something very bad has happened to me. Can you come pick me up?” He later told me he was convinced I had cancer.

I didn’t know how to move forward. I knew I needed to figure my life out. Was I going to leave my wife? Could I make it as a single-parent to my then 18-month old son?

I knew I needed to go raise money or the company would be defunct, but how was I going to get on a fucking airplane?

I emailed the 10 investors I was scheduled to meet that week and told them I had  contract the stomach flu and would need to push back a week (sorry for the white lie folks!)  Next, I wrestled with what to tell my 10-person team.

The decision that came next changed the course of my life as a leader. And the results changed my understanding of leadership entirely.
I told my team the truth.

I called an all-hands meeting. I told them, openly, with tears rolling down my face, the full truth of what was going on in my life. I shared the feelings I was experiencing. The fear I was holding. The questions I was sitting with. And I promised I would do my best to press through the fundraising and keep the company solvent.

Fast-forward two months, and I found myself faced with the challenge of having a similarly honest conversation with our prospective lead investor.  I’d flown up from LA to meet with her at her Sandhill Road office. Our corporate attorney had instructed me I had a fiduciary and moral duty to disclose my emerging divorce to our prospective lead investor.

“I need to share something quite difficult with you,” I said. “There’s something going on in my personal life that may impact your decision to invest in Twenty20.”
I went on to explain the details of the painful events that had recently unfolded in my family life.

Nothing like getting personal real fast.

Her response astounded me. Instantly human and comforting, she told me how sorry she was that I was going through something so difficult. She thanked me for being so open with her about what was going on. And she assured me she had no intention of cancelling our term sheet. That if anything my willingness to be so open made her want to work with me more. I was amazed. And filled with gratitude.

My team responded similarly. They rallied behind me with support, comfort, and grace. A significant shift occurred in my relationship with the team that would play out continuously in the coming years and very much lay the foundation for our culture. Ultimately, ‘We talk about the hard things’ was enshrined in our company values and was probably the most oft quoted of our half-dozen values. We quoted it because we lived it out so frequently.  I realize in hindsight that it started that winter.

They way my team and board responded to my openness changed me.

With the help of my coach, I began to see with increasingly clarity the opportunity at hand. The opportunity to invite my investors, board members, and advisors into true partnership. Beginning with allowing them to really know me. Matt the person, not simply Matt the CEO. To allow myself to drop the mask.

True partnership requires abandoning the pretense. The facade that one has it all together and figured out. That was tremendously hard for me as a first-time CEO, but as shared above profoundly necessary. For me, there was no other way forward. And that constraint was a profound gift to me.

Back to the present day coaching call.

Fast-forward several years to this week’s coaching call, and I found myself face-to-face with another first-time founder facing a similar challenge and opportunity.
As we reached the mid-point of our session, this brilliant, compelling founder paused. I could see a revelation breaking across her face. Registering as equal parts fear and curiosity. She proceed to ask the profound question at the heart of this difficult transition:

“If I put down the mask, who am I without it?”

Many of us hard-charging, straight-A, perfectionist types make our way through life well into our 20’s or 30’s without being forced to face this difficult question. The world allows us to bypass the self examination because our way of coping is so dangerously functional.

But every great leader reaches a point in the journey where the way that got her this far is not the way that can carry her a single step further.

For this client, perfectionism had played it’s role, and played it well, but the end of the road seemed to be drawing near. The mask of the one who ‘has it all together’ and ‘gets it all right’ that had served her so well was becoming an impediment to her ability to show up the way she desires, the way she must.

There’s no choice left but to step forward into her true self.

It’s the answer to that question, ‘Who am I without the mask’ that provides the bedrock for real leadership. A leader who can answer that question with confidence, and moreover who knows something about her own worth, value, and lovability aside from her achievements or performance, is a dangerous fucking leader.

A leader who knows who she is, who knows of her value, apart from achievement, possesses the hope of learning the greatest possible skill of any leader: the ability to get off the ride.

Most founders, CEO’s and leaders have their emotions and sense of well-being dictated to them by the ups and downs of the organization. And that’s no way to lead.

A leaders who’s own emotions are victim to the winds of the day is unable to hold space for her employees or to resource the team with stability and clarity when things get hard. But a leader who has made her peace with who she is apart from the business, who knows her loveliness apart from her performance, this leader holds the potential to resource her people with the things they need most in the hardest days of startup life.

And when she shares that self-knowledge openly with the people she leads, and invites those people into the honest details of her own journey of leadership, she becomes a gravitational force.

I have no doubt the founder on the other end of the coaching call will find her own answer to this life-defining question. And I’m incredibly fortunate to bear witness.

This work of self-discovery cannot be done alone. On my own journey, I would have been lost along the way many times without the assistance of my own wonderful coaches, my longtime therapist, and the countless friends and fellow-founders who provided counsel and company. To those who have accompanied me, I’m so grateful. To those of you who are facing your own awakening to these questions, I’d love to share a coffee and talk about the journey together. These transitions have become the heart of my life’s work.

Wherever you are in this moment, wishing you peace in your own journey today.

-Matt