testTag: leading through change

From imposter syndrome to the principles that shape how I show up

I joined Dstillery in 2017 after more than two decades in the investment community as a sell-side analyst, buy-side analyst, and portfolio manager at some of the world’s most prominent investment firms.  Over the course of that career, I followed a wide variety of industries, including ad agency holdcos, media, internet, technology and, yes, adtech.

When I made the transition to a corporate job, it was with the explicit objective of being a principal contributor to value creation by applying what I had learned as an investor.

Despite that intentional approach, I will admit I had a bad case of imposter syndrome at first.

While confident in my ability to understand the role of growth, margins, returns on capital and cash flows in value creation, there was a lot I did not know about how leaders deliver those positive outcomes.  I had studied hundreds of companies across 5 key domains:  financial, strategic, operational, culture and governance.  There are many I admired and theoretically learned from, but the truth is that I had essentially zero relevant experience.

When I was unexpectedly thrust into the CEO role after just 6 months as a CFO, I had no choice but to figure it out.  I turned to a set of principles I had developed to guide my actions over the course of my investing career.

These are not principles that tie back to financial statements or stock picking, but more of a behavioral operating system.  They are guidelines for problem-solving and decision-making, and they have been a roadmap to navigating the challenges of the transition to a job that was beyond my depth.

Even after all this time, I still am often asked what is the connective tissue between my investment career and my leadership role at Dstillery.  This framework is the answer, and I have shared it over the years with my team, my peers and my former investment colleagues.

I wrote down the first five of these principles when I launched Mojave Capital, a hedge fund seeded by Tiger Management.  Tiger’s Julian Robertson inspired the sixth.

When I joined Dstillery, I applied these principles first to my role as CFO, and then as CEO.  I applied them by default because they were what I knew, and because they comprised the person I wanted to see when I looked in the mirror.

Since Chrome introduced the feature of multiple tabs on a browser, a Google Doc with these exact principles has been always open on my computer as a reminder and reference. I have barely edited them over my nine-year tenure.

1. Process matters.  Decisions need to be made in a structured, predictable, repeatable way.  They can still be simple, but they need to be thorough and clear.  Over time, processes are meant to evolve and improve.
2. Leverage data. Use data and tools whenever available to make better decisions.  Trust the data over human biases and intuition.
3. Find your conviction. Develop conviction through a data-driven process that is tested and proven.  Conviction is not certainty; that is too high a bar.  Conviction is the confidence you need to make an informed decision with imperfect information, to trust your own judgment over the judgment of others.
4. Transparent communications. Be clear about what decision was made and how.  Emotion should be removed from communication, and good and bad news should receive equal weight and bandwidth.  Do not sweep mistakes or challenges under the rug.  They are your best feedback mechanism for continual improvement.
5. Act with urgency. Once you come to a decision with conviction, act upon it.  The world changes fast, and circumstances that inform your decision can change quickly.  A good decision unexecuted is a failure of process.
6. Grow people. Find good people and empower them.  Give talented young people more responsibility as quickly as they can handle it.  Remove people who hold you back.

Who I aspire to be

Generally speaking, what you learn to do as an investor is make and act on high-stakes decisions with imperfect, incomplete information.  To do so, you have to have a reliable process, gather as much data as you need to develop conviction in your decision, communicate the reasons for your decisions with stakeholders, and act.  Over time, you want to inspire and develop talented young people who will follow that blueprint, enhance the process and results, and help you scale.

As I found myself in the deep end of the pool, first as Dstillery’s CFO and then CEO, it dawned on me that the real reason to apply these principles to my leadership role is because they are directly relevant.  They transcend the investment process.  The core function of a corporate leader — making critical decisions through the lens of value creation — is identical to the core function of an investor.

The framework of these principles is aspirational.  I often fall short of the standards that I set for myself.  Sometimes, applying one principle may get in the way of another.  While I am gathering the data I need to find my conviction, I may delay decision-making, running afoul of my principle of urgency.  Such is life in the real world.

The lessons I learned as an investor about value creation, about myself, and about how the world works are an invaluable, reliable foundation for my role leading Dstillery.  They encode rigor, humility, intellectual honesty, curiosity, self-reflection, and collaboration.

When I look in the mirror today, I no longer see an analyst play-acting at being a CEO.  I see a confident leader with a clear, battle-tested framework, learned through a varied career for which I am deeply grateful.  I have conviction that no matter what challenges the future holds, these principles provide a foundation for decisions that will create real, lasting value.

Though it still flares up from time to time, I have largely gotten over my imposter syndrome.  I have come to believe that we all have experiences we can apply to our careers, our decisions, and our growth vectors.

As you look back over your career, think about your mentors, and take note of what you have learned.  Write it down.  Share with colleagues, loved ones, mentors.  I promise you will be dazzled, inspired and liberated by the range of learnings you can apply to your current role, or your next.

Change is scary. As a general rule, people do not like it. Change creates uncertainty, and most people’s sense of personal security is built on continuity and the expectation that tomorrow will be very much like today.

When we perceive that tomorrow is going to be very different from today, most people experience fear or anxiety. Tomorrow could be worse. I could lose my job. I might not know how to do the thing that I will now have to do. Things that I love or value might be somehow worse. Depression. Global warming. Famine! Apocalypse!!

Not everyone hates change

I have repeated the aphorism that “people hate change” many times, as if it is an undisputed and universal fact. But it is not. As with everything related to the human experience, there is a lot more nuance, and a wider range of realities.

My friend and mentor (and Dstillery director) David Bell recently shared his view with me that with regard to change, there are three types of people:

1. Past-clingers
2. Wait-and-seers
3. Let’s-goers

Past-clingers are so uncomfortable with the uncertainty created by change that they deny it, resist it, and push back against it. Their denial is a circular reference that activates the very risk that they fear, which is being left behind.

Wait-and-seers, well that is obvious. They are skeptical, but willing to be convinced.

Then there are the let’s-goers. These are the people who experience the uncertainty of change as an exciting opportunity to learn and grow.

The dust will not settle

Today, I have the privilege of moderating the following session at Velocity, an event hosted by The Athena Project in partnership with Northwestern University Medill School.

We Live in Dusty Times: How Media Agency Leaders Manage Innovation, Complexity & Fear.

Media agencies are navigating one of the most profound reinventions in their history, as AI, multimodal consumer experiences, and new forms of intelligence reshape how audiences are discovered, understood, and influenced. How are today’s agency CEOs leading through this complexity while helping clients embrace innovation without losing sight of trust, creativity, and business results? This conversation explores how leaders prepare themselves, their teams, and their clients for a future defined by extraordinary opportunity—and equally profound disruption.

It is a brilliant topic, and I am thrilled to have the opportunity to delve into it with Lisa Collings of Mindshare, Domenic Venuto of Horizon Media and Shelby Saville of Starcom.

In my preparation to moderate, I discovered the meaning behind the title “We Live in Dusty Times.” It is from this (excerpt of a) post by Shelby:

⚡ Change is the new normal.

The pace isn’t slowing. And that’s okay. I was recently asked what this industry will look like “when the dust settles.” My answer is that it won’t. We live in dusty times, my friends. For our clients and our people, leading with focus, clarity, and transparency matters more than ever, even when the path ahead isn’t clear. When I’m unsure, a mix of perspective, pragmatism, and purpose has been my superpower. And I’m never afraid to say, “I don’t know.” Because my teams and clients know we’ll figure it out, together.

Are you a past-clinger?

It is unnerving to realize that we have little choice but to lean into change without a clear idea of where it will lead us, and that we cannot simply wait for the dust to settle.

It led me to an introspection exercise.

Open your mind, look in the mirror, and ask yourself whether you are a past-clinger, a wait-and-seer, or a let’s-goer. Answer honestly, and ask yourself why. And finally, ask yourself whether that is who you want to be.

Me? I am somewhere between a wait-and-seer and a let’s-goer.

I have a deep respect and even envy for the let’s-goers. They are the ones who are going to do exciting things and have tons of fun. Some may become trillionaires.

But a 20+ year career as an investor imbued me with healthy respect for risk that slows me down a step relative to the let’s-goers. In any decision, I seek conviction before I act. Conviction is the governor between waiting to see how things will unfold and diving in.

Rooting for the let’s goers

The profound value of David’s insight is not the categorization of people. It is that companies thrive when they empower and unleash the let’s-goers. Remove organizational obstacles. Give them permission to pursue opportunities. Reward their initiative, and celebrate their achievement.

The idea is that the more visibility and influence the let’s-goers have, the more past-clingers will be inspired to become wait-and-seers, and wait-and-seers to become let’s-goers. The more people we can move across the continuum, the faster we will go as a company.

I love this model for acceleration, because it does not impose the unrealistic standard that we are all going to be let’s-goers. Instead, it allows the let’s-goers to bring the rest of us along, and to be agents of acceleration.

Growth comes from change. Change is constant. So we all can and should be constantly growing. Whichever category we find ourselves in, we all ought to be rooting for the let’s-goers.