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James writes under the handle JimmyThePencil on Medium, a nod to his accounting background and a pencil thin mustache from his college days. His posts cover leadership, entrepreneurship, family life, and reflections from over a decade inside VaynerX, written in his own direct voice.
Don't Delegate, Facilitate
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Don't Delegate, Facilitate

James explains the difference between delegating and facilitating, describing how he helps move forward 800 plus employees across VaynerX's offices rather than managing a small team of direct reports.

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James Orsini
And For My Next Act
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And For My Next Act

Written on his 11th anniversary at VaynerMedia, James reflects on the single word he chose to describe himself on his first day and how that word still defines his approach to work today.

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James Orsini
My Internship Changed My Life
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My Internship Changed My Life

Reflecting on welcoming a new class of interns at VaynerMedia, James looks back on his own internship more than thirty years earlier at what is now KPMG and how it shaped his career.

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James Orsini
A Look Back on vYve from Inside the Hive
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A Look Back on vYve from Inside the Hive

James reflects on being appointed President of Startup Operations for VaynerX in 2024, his fourth title and fifth role under Gary Vaynerchuk, and the research process that led to creating vYve.

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James Orsini
Create Your Own Job, Don't Send a Resume
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Create Your Own Job, Don't Send a Resume

Written after Travis Kalanick's exit from Uber, James shares his philosophy on building your own opportunity rather than waiting to be hired into one.

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James Orsini
Hey Sasha, It's 5, Time to Move On
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Hey Sasha, It's 5, Time to Move On

Reflecting on five years leading The Sasha Group, James traces its growth from under 10 million in revenue and 30 people to over 20 million and 110 employees, and welcomes Marcus Krzastek as his successor.

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James Orsini
Networking for Success
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Networking for Success

An early piece from James on how genuine relationship building, not transactional networking, has shaped the opportunities throughout his career.

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James Orsini
Sasha 2021, Tag You're It
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Sasha 2021, Tag You're It

A year in review piece looking back on 2021 for The Sasha Group, introducing the tagline Sasha the Heart of VaynerX as revenue climbed to 15.5 million and headcount to 75 people.

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James Orsini
Some Quiet Time at the Jersey Shore
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Some Quiet Time at the Jersey Shore

A personal piece on why James treats annual family vacations as a fixed cost rather than a luxury, written after a trip celebrating 35 years of marriage to his wife JoAnn.

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James Orsini
Sasha 2020, A Dream Without a Plan Is Nothing More Than a Wish
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Sasha 2020, A Dream Without a Plan Is Nothing More Than a Wish

James introduces the Eisenhower Matrix as the decision making framework The Sasha Group used to prioritize its second year of growth, developed by hand on paper and refined with Gary Vaynerchuk.

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James Orsini
Sasha, And the Last Shall Be First
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Sasha, And the Last Shall Be First

Written as The Sasha Group first launched, James describes the feeling of being given a shot at something meaningful and lays out the firm's mission to serve businesses with 1 to 100 million in revenue.

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James Orsini
The Entrepreneur Health Check
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The Entrepreneur Health Check

Coming off two multi-day vYve gatherings with nearly two dozen entrepreneurs and founders from around the world, James shares what he observed about the health and mindset of today's business leaders.

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James Orsini
My Observations From Inside the Boardroom
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My Observations From Inside the Boardroom

Reflecting on the Business Roundtable's move to redefine corporate mission around Stakeholder CEOs, James shares lessons from his time in public company, higher education, and private boardrooms.

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James Orsini
Why So Much Greed
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Why So Much Greed

A reflective piece on greed in modern business, tracing James's own memory of the 1987 film Wall Street and how that era's lessons still apply today.

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James Orsini
Small Business Wants and Needs
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Small Business Wants and Needs

Drawing on 7 years working closely with founders and small business leaders alongside Gary Vaynerchuk, James breaks down what entrepreneurs actually need versus what they think they want.

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James Orsini
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