Lessons From My Youth: An East Coast Upbringing Defines a Silicon Valley Career

My kids doubled-over laughing. 

“Dad, it’s just a ferris wheel. We’re only 100 feet off the ground. Are you really that scared?” said my daughter, Sierra.

I played along with the insults and giggles to mask the very real fear that was flooding through my brain.

It was less than a month since a widely-covered Ohio State Fair accident ended in fatal tragedy. My knuckles were a shade whiter and I stared a bit closer at the rust-covered bolts supporting our chair. The fresh grease pencil markings on each support beam confirmed that the underpaid, overworked construction crew slapped this rickety contraption together just a few days prior to our ride.

We were the only occupied carriage on an early spin at the Orange Fireman’s Carnival in New Haven, Connecticut. I brought my kids here so they could experience the same summer thrills I enjoyed at this very same event over 40 years ago. My wife, Julia, and I were spending a week with our children on the East Coast for the first time in five years. We returned so our kids could visit their grandparents whose mobility is fastly deteriorating. We got lucky to discover that our visit overlapped with the local, small town carnival that has been the primary fundraiser for the Orange Volunteer Fireman’s Association for close to 90 years. What a treat for us all.

When we reached the top of the ferris wheel, the snickering subsided and we all took in the view from our lofty perch. Looking west, all we could see was an unbroken sea of vibrant green trees stretching to the horizon. In the opposite direction, we could observe the expanse of the carnival. A dozen thrill rides, a few rows of deep-fried food vendors, and the quintessential games-of-chance -- complete with carnies trying to coax a few dollars from bored parents or enthusiastic but naive kids.

Soaking in the bird's-eye view, the orchestra of joyful noises, and the smells of roasted peanuts, I was struck by how little had changed at this event in the more than four decades since I was here last.

It was as if time had stood still.

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“Dad, are you scared up here too?” my daughter Autumn joked from between airplane seats on our flight back home to Silicon Valley the next day. Before I could muster a response, she fist-bumped her two sisters and reset her earbuds as they settled in for their third Netflix feature of the day.

For the next few hours -- as we transversed the corn field ocean of the Midwest, the majestic crags of the Rockies, the wind-carved canyons of Utah, the cathedrals of the Sierra-Nevada, and finally the kaleidoscope-colored salt ponds of the San Francisco Bay -- my mind turned inward and I reflected on the fortunate course of my life.

From my youthful summers at the Orange Fireman’s Carnival to our adopted home 3,000 miles away in the San Francisco Bay Area, it was clear that though the carnival might not have changed since the 1980s, I sure had.  

My wife, Julia, and I -- high school sweethearts married in the early 1990s -- left the East Coast and pointed our old two-seater west. We didn’t stop until we hit the Pacific and the inviting embrace of California.

California has been good to us in every way, so much so that we could not fathom living anywhere else. 

Despite California being the only place I can imagine calling home, I do owe an enormous debt of gratitude to what I learned growing up in the suburbs of New Haven, Connecticut. There’s just something about a New England town -- brimming over with practical and resourceful folks -- that sets one up to thrive in the wider world.

As I think about the enormous prosperity I’ve enjoyed in California’s tech sector, I cannot help but admit that the credit really belongs to the learnings of my youth on the opposite coast. 

It’s a few of those lessons for success that I share here.

Critical and Contrarian Thinking

Today, “Sue Duffy” is my password recovery answer when asked, “Who is your favorite teacher?” But a long time ago, she was my mentor. 

Ms. Duffy co-taught with Ms. Leach a groundbreaking course at my high school in the 1980s called Critical Thinking. Two teachers and no textbook. This course, as its name implied, was designed to make us reflect, discuss, and defend positions on current issues. The only homework was to read assigned articles from Newsweek magazine, pick a side on an issue, and come to class ready to defend our position.

The Cold War. Trickle-Down Economics. AIDS. Contras. They were all fair game. 

This was not truly a debate class. Its goal, rather, was to start us down the road of being engaged citizens, thoughtful in developing our view of the world and willing to consider the perspectives of others. 

Ms. Duffy pushed and prodded me throughout that course and her supportive cajoling has done more to shape who I am today than any other relationship outside of my family.

I was thrilled to find her phone number on the Internet prior to our East Coast trip and I was able to introduce my kids to her just a few hours before that death-defying ferris wheel ride.

Despite Newsweek ceasing its paper edition in 2012, and Sue now fighting cancer, we had just as enjoyable and vigorous a discussion that Friday afternoon as we had 30 years prior.

Sue Duffy taught me to think for myself; to not follow the crowd. Assemble the facts as best you can, listen carefully to all sides of an issue, and then make a choice with conviction.

Planning and Long-Term Horizons

You split wood in the spring for fuel in the winter.

The New England seasons necessitate long-term planning. Installing snow tires when the leaves turn color. Raking leaves before the first snow falls. Checking that the engine turns over on the snow blower while taking a rest from raking those leaves. Fixing broken screen windows in the basement while a snowstorm rages relentlessly outside. Picturing the explosion of color and renewal of life that a spring garden brings when planting bulbs in the Fall. Changing the air conditioner filters after the first crocus peak up its head between melting snow.

It seemed my entire youth in New England was spent not living in the present but planning for the future. With four distinct seasons -- each with its own challenges -- there was great joy in staying ahead of the chores to ensure you did not get caught unprepared for what seasonal challenges were unavoidable ahead.

This “plan for tomorrow’” approach, honed during the seasonal battles of my New England upbringing, has served me well not only in my personal life but in my professional one as well. 

Thinking through unplanned or quickly shifting circumstances has been a mainstay of how I have worked with my employers and planned for multi-year client relationships. In the same way short and quick fixes won’t get you through a harsh New England winter, they don’t serve you well in business either.

Although the Mediterranean climate of the San Francisco Bay area doesn’t have me stacking cords of wood or nursing blisters from endless days of raking leaves, the planning habit of my youth has morphed into an essential characteristic of my business style. 

Candor and Forthrightness

I am known for being candid.

Probably no personality trait of mine is more distinctive. My accent might be now diluted, but my manner of speaking is as strong today as when I left Connecticut three decades ago.

Growing up, speaking your mind and being direct was the standard style of communication back East. It’s how you communicate with people you cared about. The toughness required to combat what Mother Nature might throw at you tends to create a thick skin that makes it hard to be offended by the words of mere mortals.

To some lifelong Californians, my approach can be mistaken for callousness and insensitivity if I am not careful. But, for every time I’ve inadvertently offended someone due to my communication style, a dozen individuals have told me they find it refreshing.

I don’t lie. I call ‘em like I see ‘em. I often speak what others are thinking but are afraid to say out loud. I listen like it matters. Because it does.

At the same time, California is teaching me to be ever-respectful and universally empathetic. It’s a hard-on-the-outside-but-soft-on-the-inside approach that I think the world needs a bit more of these days. More people need to speak up respectfully, share their ideas without fear, and live life unburdened by the opinions of others defining how one sees oneself. Civility, of course, is the essential ingredient.

I have got to tell you, being forthright is quite liberating once you give it a whirl.

Spend a few hours in a local New England tavern talking sports or politics or religion (often all three are the same thing) if you need to get your courage up. I promise the regulars will buy you a round of Yuengling, Rolling Rock or Sam Adams... even if they disagree with every damn thing you say.

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In the spirit of that candid style, let me end with this.

Despite an idyllic childhood and a debt of gratitude to the region, I don’t regret leaving the New England of my youth. Even If my kids were never able to enjoy that small town ferris wheel, the San Francisco Bay area affords them other heights and horizons to which they are being lifted.

2016 marked my 18th year lucky enough to reside in the City by the Bay and the longest time I have ever lived in the same location. I am planning on closing out my days with 50 or more years here with a little bit of luck.

As for my youth, I am not just nostalgic about my formative years in New England but properly appreciative of the trajectory it launched my life. I am forever mindful of having brought a piece of it west with me.

The lessons of my East Coast youth were foundational for my West Coast success. And for that, I am eternally thankful.

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Are you too an East Coast transplant to the San Francisco Bay area? Do these traits remind you of your upbringing or how you approach the business world?

If so, consider joining LeadGenius. We need more industrious, free-thinking, smart and hard-working folks - regardless of where you grew up.

Open positions are posted here. If you don’t see the role for you, but you think we should consider you anyway, make your case by emailing [email protected].

We look forward to hearing from you.