How Did You End Up Here?

Today I turn 43. Each October in the days leading up to my birthday, I carve out time to reflect on the changes I made, what I’ve learned, and who I’ve become in the past year. This isn’t as intensive as my annual review process, but it’s something that I look forward to every fall.

This year has been different. I took a new approach that began this spring when I reread Let Your Life Speak by Parker Palmer, one of my favorite authors. I was stopped in my tracks when I read this passage:

“We arrive in this world with birthright gifts—then we spend the first half of our lives abandoning them or letting others disabuse us of them. As young people, we are surrounded by expectations that may have little to do with who we really are, expectations held by people who are not trying to discern our selfhood but to fit it into slots. In families, schools, workplaces, and religious communities, we are trained away from true self toward images of acceptability; under social pressures like racism and sexism our original shape is deformed beyond recognition; and we ourselves, driven by fear, too often betray our true self to gain the approval of others.

We are disabused of original giftedness in the first half of our lives. Then—if we are awake, aware, and able to admit our loss—we spend the second half trying to recover and reclaim the gift we once possessed.

When we lose track of our true self, how can we pick up the trail? One way is to seek clues in stories from our younger years, years when we lived closer to our birthright gifts.”

That set me on a quest to pick up the trail and rediscover my birthright gifts that were abandoned long ago and buried underneath layers of armor and personas. Thankfully, I had several old journals that became important artifacts in my quest—one from my sophomore and junior years of high school, and another from my freshman year of college. They were packed with clues. What a gift.

Over the summer, I spent several afternoons unpacking what I wrote and getting to know my former self. What surprised me most? Many of my best qualities—introspection, compassion, self-expression, exploration—were evident throughout those pages. In one of my entries, I wrote “sit back, relax, and let life unfold.” It turns out this life philosophy, which I thought had emerged for the first time when I began to study Buddhism, was deeply embedded in me! I was also surprised to read that I wanted to be a teacher and coach, and mentor young men. In many ways, those are still the things I want today. My birthright became clear—to mentor, teach, and serve others.

Once I had this realization, I began to wonder how I got stripped of my original giftedness and birthright for so long, or whether the circuitous path I took back to that birthright was simply the journey I needed to take. How did I get into business, and what excited me about that path—or was it a detour? This curiosity gnawed at me for days. I finally got out my journal and began to ask myself some important questions that would help me illuminate and reconstruct the trail I’ve been traveling for nearly twenty-five years.

Some questions I asked included:

• What was I genuinely interested in as a kid and teen?

• How’d I pick my college, major and internships?

• How did I decide on an initial career track?

• Who influenced the kind of lifestyle I wanted?

• How did I land my first job?

• Who has influenced my career decisions?

• What job changes and transitions have I experienced? What drove them?

What I learned was fascinating, and deeply illuminating.

Tracing My Path

How did I pick my college and major?

When I was applying to college I didn’t have much help. In fact, I didn’t visit any schools, and I filled my applications out by hand because we didn’t have a computer at home. I wound up choosing Springfield College, a small college in Western Massachusetts, because it was close to home and they have excellent programs in the humanities. My high school guidance counselor recommended it because many of their graduates go into helping professions such as teaching, physical therapy, athletic training, and nursing. In fact, the school’s credo—“spirit, mind, and body”—still resonates with me.

I chose to study education and healthcare management because Springfield has solid programs in these areas, and I thought I wanted to teach and coach high school sports. More specifically, I wanted to mentor teens and coach football. I loved playing sports, being part of a team, leading others, and, of course, winning. I was an A student, Vice President of my class, and active on campus as a student leader. But after three semesters, I began to feel like a big fish in a small pond and my interests started to evolve. In my Sophomore year, I became interested in business and decided to transfer to Northeastern University to pursue a new major.

Why business?

My older brother, Jon, had just graduated from Bates College and had some early career success working in finance. I saw that he was independent financially and had a high quality of life that I didn’t know was possible. In fact, he was in his mid-20s and already driving a BMW! This appealed to me because our family was living paycheck to paycheck when I was a kid. It was clear this path would be more rewarding financially than teaching or coaching high school sports. Given my success at Springfield, I believed I could succeed on this path despite knowing nothing about business. I figured I could learn it, especially at Northeastern, the leader in cooperative education, because they combine classroom instruction with real-world experience. Three years later, I had a 3.9 GPA, a year of internships under my belt, and a full-time job offer from Microsoft.

How did I land my first job?

My advisor at Northeastern encouraged me to apply to a six-month internship at Microsoft because I was one of the top students in the business school. I knew very little about technology and software. In fact, I didn’t even own a computer! The extent of my knowledge was through video games and ripping music on Napster. So I put on a good face, studied the company and the software industry, and got the gig. (I had dinner at Bill Gates’ house once during the internship—this was definitely one of the highlights!)

Six months later, I was offered a full-time role upon graduation, and accepted it on the spot. I mean, how could I turn down a job offer from the top technology company in the world? I didn’t even consider “my options” even though I was recruited by investment banks, consulting firms, and “the big five” public accounting firms. I bought into the premise that technology could help people realize their potential.

When I got to Seattle and Microsoft, I immediately felt like a fish out of water. Perhaps because I knew deep down inside that I wasn’t meant to be there. In fact, one of the recruiters once told me that I was “too rough around the edges” and wondered out loud how I got a job at the company. I shit you not. But despite the way I felt and the messages I received, I drank the Kool-Aid, put my head down, and embraced my identity as a worker in tech. This became my existence and obsession. At this point, the idea of doing anything else no longer occurred to me.

How did I become a VC?

This was an accident. I had no aspirations to become a VC. In fact, I didn’t know any VCs or much about the industry and its inner workings. I just happened to be in the right place at the right time—not once, but twice.

My first taste of the profession was a stroke of luck that started over a casual dinner conversation with my then girlfriend, now wife, Eliza. She asked me what my dream job would be, and without hesitating, I said “work in a strategy role at the NFL.” A few days later, I applied for a job at the League, made it through three rounds of interviews, but I was eventually rejected. Crushed, I thought the door to this dream had closed. But months later, my resume was unexpectedly sent to The Kraft Group, owners of the New England Patriots, by the same person at the NFL who’d first rejected me!

During my first interview, Jonathan Kraft explained the Sr. Analyst role would be responsible for evaluating a variety of opportunities including investments in startups and funds. I remember going home that day and scouring the web for information on how to evaluate a venture deal.

Back in 2007, there were few, if any, blogs on the topic, and VC Twitter didn’t exist. In other words, there was scant information and resources to help a newbie like me. But I was intoxicated by the idea of investing in startups so I hustled and faked it until I made it. I threw myself into the profession, learning the industry, meeting with founders, expanding my network, and drinking even more Kool-Aid.

Nine months after I left The Kraft Group and moved to NYC, I was at a bar in the East Village, went outside for a smoke, and was browsing Twitter to kill some time. I saw a tweet from Ben Lerer announcing Lerer Ventures was hiring a Principal. This seemed like the perfect opportunity, and a great match, so I threw my hat in the ring, and a few weeks later I got the job. Now, in what seemed like a blink of an eye, I was working for the hottest early-stage fund in NYC. If I hadn’t opened up Twitter on the fateful evening, I probably would have ended up at some random startup because there weren’t nearly as many VC firms back then.

Little did I know that I would spend nearly a decade in this profession, before deciding to become a coach.

How did I become an executive coach?

I saw Eliza, who is the Founder / CEO of The Sill, struggle with the human and emotional aspects of running an early-stage startup. I began to wonder why investors didn’t support their founders mentally and emotionally. Pretty much all the founders I worked with at Lerer Ventures would tell me they were crushing it, and I knew that couldn’t be true. Something seemed off. Then I met Jerry Colonna, the legendary CEO coach, after hearing him on a podcast in 2013. I was immediately drawn to him and captivated by his work. I began to wonder if there was an opportunity to combine investing with coaching and leadership development. I wasn’t sure, so I dove head first into coaching, enrolled in a certification program, and began to support clients. I ultimately discovered that I loved coaching more than investing because it took the part of investing that I loved—supporting founders—and eliminated the part that caused me anxiety—sourcing, picking investments, and being at odds with founders. And then I discovered that I could make a great living, support my family, and have the space to seek tremendous balance. I was sold!

What else influenced my transition(s)?

Three other events had a huge influence and impact on my transition from investor to coach. These include learning how to meditate, getting sober, and COVID. As someone who was diagnosed with ADD early in life, I struggled with sitting still and an incessant mind. Meditation allowed me to slow down, and see the content and nature of my thoughts. With enough practice, I began to question my existence and experience, including why I was stoned most of the time. That led me to sobriety, and I discovered in the rooms of AA that service is a big part of a sober life. This reinforced my decision to pursue coaching because a part deep down inside told me that VC wasn’t service as much as I wanted to believe that it was. Finally, when COVID-19 hit, my family and I moved upstate to the Catskills. It was the first time in over a decade that I left NYC for an extended period of time. No more running from meeting to meeting. No more tech events. I got a taste of a different life in nature—grounded, calm and creative—and it deeply resonated with my being. That’s what I truly wanted. My family and I eventually returned to NYC 18 month later, but I was a changed man. Shortly thereafter, I walked away from my venture fund and fully embraced myself as a coach.

How did I decide to coach startup founders and leaders?

The honest answer is inertia and expertise. I’ve spent half of my life in technology and startups. It’s what I know. I have deep domain knowledge, a massive network, and a strong reputation among founders and investors. I’m also damn good at it, and enjoy the work. Additionally, it happens to be lucrative and flexible, so I can support my family doing this. When I step back and look at the trail, coaching appears to be a natural progression and extension of the world I came from. It’s also a return to my roots, satisfying my earlier longings to coach and teach, thus completing a full 360 without even realizing it.

What I’ve Learned, What I Still Don’t Know

What if I shrugged off the decision to transfer to Northeastern? What if my brother accepted a job in publishing instead of finance? What if I had a different advisor who recommended public accounting? What if Eliza never asked me what my dream job was? What if I wasn’t on Twitter the night Ben Lerer sent that tweet? What if I didn’t hear Jerry Colonna talk about executive coaching on that podcast? What if I had just listened to myself in high school and became a teacher and a football coach?

It’s amazing what we can learn about ourselves when we step waaaay back, see our birthright gifts, identify our influences, trace the path we’ve taken, and note what we’ve learned about ourselves in that journey—are we far away from where we started, or did we find a way back? Are we grateful for the distance, or are we yearning to return?

As I reflect on this exercise, I’m reminded of Steve Jobs’ 2015 commencement speech at Stanford:

“You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever."

When I connect my dots looking backwards, I’m filled with pride and gratitude, but also some sadness. I’ve clearly been blessed with an amazing journey, but when I really zoom in, I see the path was not only serendipitous but also reactive, opportunistic, and unconscious. I also see now that I denied my true essence and original giftedness in favor of money, power and influence—all of the things society values and I thought I wanted. But deep down inside, I’ve longed to be a teacher, a coach, and a mentor. Simply put, I want to be a good, decent man who helps others succeed, and thrive.

So now that I recognize this, I’m wondering what it would look like to place a new dot on the trail. One that’s highly intentional and self-authored based on my values, birthright and original giftedness, as Parker Palmer described above. What would it look like to fully step into my power as a teacher, coach and mentor?

This thought experiment is leaving me with some big questions:

• What chapter do I want to write next?

• What would bring me and my gifts fully alive?

• What’s truly needed in the world?

• Who do I want to serve?

• What do I want to teach?

• What medium do I want to use?

• Who might I partner with to amplify this work?

Here’s what I realize as I enter my 43rd year on this giant rock spinning in the middle of an infinite universe—some questions are meant to be answered right away because there are definite and clear answers, and other questions are meant to be sat with for periods of time to see what changes and emerges. These big questions I’m asking are of the second order.

What if there’s nothing for me to do right now? What if there’s nothing to figure out? What if I just let this unfold and let it be rather than trying to make something happen as I have for most of my life? What if I trust the process will eventually reveal the next logical move that’s in alignment with who I am and who I’m meant to become? What if I just “sit back, relax, and let life unfold” as I wrote more than 25 years ago? This approach feels appropriate and friendly to me.

While I’m in no rush to place a new dot on the trail, I have plenty of ideas of what it might look like and where it might take me. Before I get ahead of myself, I plan to take it one step at a time, and when the time is right, I’ll intentionally design the path forward based on what emerges and what I learn. This much I know: I will honor my selfhood by stepping into my power as a coach, teacher, mentor, husband and father.

So as I prepare for another trip around the sun, I’m sitting with awe and wonder, appreciating the trail I’ve walked and how it has led me, somewhat unexpectedly, to the person I was born to be. It turns out, after all the twists and turns, I’m in exactly the right place.

Isn’t it amazing what can happen when we stop and ask ourselves one simple question?

So, how did you end up here?