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Leadership | How James Actually Leads

Curated byJames Orsini3 stacksUpdated Sep 2026
James's own words, writing, and interviews on what it actually takes to lead: translating a founder's vision, building trust, and owning his mistakes.

Insights on leadership, finance, and entrepreneurship from James Orsini.

Difficult Conversations in Leadership with James Orsini
theorsiniway.com
Difficult Conversations in Leadership with James Orsini

In this episode, James Orsini discusses the importance of navigating difficult conversations in leadership roles. Listeners will gain insights into effective communication strategies that can enhance their leadership skills and foster better team dynamics.

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James Orsini
VaynerX’s First Retiree Marks a New Milestone
lbbonline.com
VaynerX’s First Retiree Marks a New Milestone

James Orsini reflects on a career that took him from Wall Street to advertising, sharing lessons on people-first leadership, financial discipline, and a decade spent building operational muscle inside a fast-growing Vayner. This article highlights his journey and contributions to the company.

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James Orsini
How Finance Fuels Creative Vision in Business
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How Finance Fuels Creative Vision in Business

Discover how James Orsini uses finance to empower creativity, scale agencies, and drive growth with data and strategic leadership.

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James Orsini
And for my next act…
medium.com
And for my next act…

In this reflective piece, James Orsini shares his journey at VaynerMedia over the past 11 years, highlighting personal growth and the significance of self-identity. Through a simple yet profound anecdote involving a chalkboard, he explores the essence of what defines him professionally and personally.

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James Orsini
The Entrepreneur Health Check
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The Entrepreneur Health Check

This article discusses insights gained from multi-day meetings with entrepreneurs and founders worldwide. It highlights the importance of health checks for entrepreneurs to ensure their well-being and business success.

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James Orsini
VaynerX’s First Retiree: Celebrating a Career and a Company Milestone
vaynermedia.com
VaynerX’s First Retiree: Celebrating a Career and a Company Milestone

VaynerX first retiree James Orsini reflects on a 35+ year career and over a decade at VaynerMedia, where his people-first leadership helped scale the company into a global independent agency and marked a major VaynerX milestone.

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James Orsini

Articles, Medium posts, and guest write-ups where James is actually talking about leading, not just career history.

A Look Back on vYve from Inside the Hive
medium.com
A Look Back on vYve from Inside the Hive

In this article, James Orsini reflects on his experiences and roles at vYve, a company led by entrepreneur Gary Vaynerchuk. He shares insights from his journey and the impact of his leadership within the organization.

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James Orsini
Sasha: And the last shall be first…
medium.com
Sasha: And the last shall be first…

This article by James Orsini, President of The Sasha Group, explores the feelings of being at the back of a long line and the insights that come from such experiences. It delves into themes of patience, perseverance, and the eventual rewards of waiting one's turn.

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James Orsini
Business Leader Expertise: James Orsini on Perseverance
medium.com
Business Leader Expertise: James Orsini on Perseverance

This article features an interview with James Orsini, President of the Sasha Group, discussing the importance of perseverance in business leadership. Orsini shares insights on recognizing strengths and leveraging them for success.

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James Orsini
My Observations from Inside the Boardroom
medium.com
My Observations from Inside the Boardroom

In this article, James Orsini shares insights gained from his experiences in the boardroom, particularly in light of The Business Roundtable's recent announcement about redefining corporate missions around stakeholder interests. The piece explores the implications of this shift for CEOs and businesses alike.

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James Orsini
Hey Sasha: It’s 5… time to move on.
medium.com
Hey Sasha: It’s 5… time to move on.

This article reflects on the journey of The Sasha Group, which has been in existence for over five years. It discusses the significance of the number 5 and what it means for the future of the group.

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James Orsini
James Orsini: Building A Multi-Million Dollar Business
medium.com
James Orsini: Building A Multi-Million Dollar Business

This article explores James Orsini's journey to becoming the COO of Vaynermedia, detailing his career path from public accounting to significant roles in finance and business. It highlights the pivotal moments and decisions that contributed to his success in building a multi-million dollar enterprise.

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James Orsini

Interviews exploring leadership lessons and entrepreneurial insights from James Orsini.

#162 - James Orsini on Leadership, Innovation, VaynerX, vYve & the Future of Entrepreneurship
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#162 - James Orsini on Leadership, Innovation, VaynerX, vYve & the Future of Entrepreneurship

On this episode of The Necessary Entrepreneur, host Mark Perkins sits down with James Orsini, President of Startup Operations at VaynerX, to share insights on leadership, innovation, and entrepreneurship. The conversation covers essential topics such as scaling businesses, the role of AI, and the importance of company culture, providing valuable wisdom for founders and CEOs alike.

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James Orsini: Q&A Session
onlinegeniuses.com
James Orsini: Q&A Session

Join us for a Q&A session with James Orsini, President of The Sasha Group, on November 11th, 2021, at 10:00 AM PST (1:00 PM EST). Learn how Orsini, alongside Gary Vaynerchuk, helps small businesses achieve explosive growth.

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James Orsini: The Legend of 'Jimmy the Pencil'
thepozcast.com
James Orsini: The Legend of 'Jimmy the Pencil'

James Orsini is the President of The Sasha Group, a VaynerX company named after Gary Vaynerchuk’s father. Working alongside Gary, Orsini leads the group to help small businesses grow through innovative strategies and insights.

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James Orsini
The Cannonball Mindset Podcast with James Orsini
youtube.com
The Cannonball Mindset Podcast with James Orsini

In this episode of The Cannonball Mindset Podcast, James Orsini, COO of Vayner Media, shares insights on the importance of working for a person rather than a company. Listeners will gain valuable perspectives on leadership and personal growth from Orsini's experiences in the fast-paced world of media and entrepreneurship.

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Interview with James Orsini - COO of VaynerMedia
brittanykrystle.com
Interview with James Orsini - COO of VaynerMedia

Today James Orsini is talking about launching new divisions, operating & scaling a global digital agency & what it really takes to execute garyvee's vision.

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James Orsini