Jason Calacanis Enneagram Type 3

DJ Wayne djwayne3 Twitter Sun Jul 30 2023

Are we all not stars in our narratives, aching to make a mark? Driven by success, we mold ourselves to fit the accomplishment framework. And in this shared human experience, few exemplify the journey of The Achiever - the Enneagram type 3 - as vividly as Jason Calacanis. Let's dive into a nuanced understanding of Jason Calacanis' personality through the lens of Enneagram.

Disclaimer This analysis of Jason Calacanis’s Enneagram type is purely speculative, based on publicly available information, and may not reflect the actual personality type of Jason Calacanis.

Jason Calacanis

Jason Calacanis

TL;DR: Why Jason Calacanis is an Enneagram 3
  • A Prolific Investor and Podcaster: Jason Calacanis, as an accomplished angel investor and the influential co-host of the "All In Podcast," embodies the Type 3's drive for success. His ambitious endeavors and achievements in the tech startup scene reflect a Type 3's determination and goal-oriented nature.
  • Inner World: Aspiration and Persistence: Behind the scenes, Calacanis likely battles the typical Type 3's fear of worthlessness, which fuels his continuous quest for accomplishment. His rigorous work ethic and a commitment to self-improvement uncover a relentless pursuit of value affirmation.
  • Controversy: The Power Play: Calacanis' perceived attempt to take over the "All In Podcast" stirred minor controversy. This move mirrors Type 3's underlying fear of being unvalued or insignificant, often prompting them to secure control over their public image and spheres of influence. It invites an empathetic understanding of his endeavors as a means to assert his worth.
  • Core Motivation: Affirmation of Worth: Calacanis' constant striving for success, evident in his professional achievements and relentless moderation on the podcast, aligns with a Type 3's core motivation - the affirmation of self-worth. His career trajectory is a testament to his enduring pursuit of significance and the desire to shine as a unique individual in his field.

Jason Calacanis: An Embodiment of The Achiever?

Internationally recognized entrepreneur, angel investor, and host of the ”This Week in Startups” podcast, Jason Calacanis, has left an indelible imprint on the tech industry. But what could be the driving force behind his accomplishments? Could it be an inherent yearning to feel valuable and worthwhile, characteristic of the Enneagram Type 3 - The Achiever?

The Achiever: An Overview

Type 3s, or Achievers, are characterized by their desire for success, ambition, and competency. They embody the best in culture, often serving as role models that inspire others to more extraordinary personal achievements. However, they are also driven by their basic fear of worthlessness. Their pursuit of success is a quest for affirmation, a desire to be admired, to distinguish themselves from others, and to validate their value.

Threes may become disengaged and apathetic when stressed or disintegrated, akin to an unhealthy Nine. On the other hand, when they are growing or integrated, Threes become more cooperative and committed to others, much like healthy Sixes.

Jason Calacanis: Tracing The Achiever’s Path

In Calacanis’ journey, we can observe the hallmark qualities of a Type 3. His entrepreneurial success stories, from Weblogs Inc to Mahalo, stand testament to his ambition and competence. He is a self-proclaimed “hustler,” striving relentlessly toward his goals, embodying the Achiever’s drive for advancement.

The Charmer and The Professional

In his interpersonal relationships and public persona, Calacanis often displays the charm and diplomacy associated with Threes. He manages to create an impression, whether it’s through his assertive statements on Twitter or the charisma he displays in his podcast.

A Three with a Two-Wing, often called “The Charmer,” is known for its warmth, ambition, and people-pleasing tendencies. While a Three with a Four-Wing, termed “The Professional,” balances their dreams with a sense of individualism and introspection. Calacanis seems to oscillate between these two sides, embodying the outgoing charisma of a “Charmer” and the professional composure of a “Professional.” Nowhere is this more evident than in how he describes building his network.

Beyond The Glittering Image

While the Achiever in Calacanis is evident, it’s essential to acknowledge the challenges of this Enneagram type. Threes, in their pursuit of success, can become overly concerned with their image and disconnected from their true feelings. In some instances, Calacanis’ competitiveness and workaholism have been subjects of debate. These tendencies mirror the Achiever’s potential pitfalls, highlighting the importance of introspection and authenticity in maintaining balance.

The Journey Towards Self-Acceptance

Nevertheless, Calacanis’ journey also provides a fascinating glimpse into the Achiever’s path toward growth. As he embarks on new ventures and evolves his persona, he is inching closer to the integrated or healthy state of Type 3, marked by self-acceptance and authenticity.

How Jason’s enneagram type can be seen influencing his work

Jason’s first major triumph, co-founding Weblogs Inc., indicates the ambitious, competent nature of Type 3. The way he later leveraged his skills and insights as an angel investor, scoring wins with companies like Uber, further showcases his goal-oriented mindset and knack for achievement.

Calacanis consistently states that hard work is the key to his success, which echoes Type 3’s tendency towards workaholism. However, it’s his flexibility and determination where we truly see the Type 3 shine. When his venture, Mahalo, struggled, he didn’t give up. Instead, he transformed it into a successful YouTube video content provider, Inside.com, demonstrating Type 3’s adaptive, success-focused nature.

Furthermore, through his popular podcast, “This Week in Startups,” Calacanis exemplifies a Type 3’s charm and charisma. His ability to captivate audiences, motivate, and inspire others aligns with the natural leadership and charm commonly seen in this Enneagram type.

Jason’s impact on “The All in Podcast”

Jason Calacanis’s influence on “The All In Podcast” is a testament to his Enneagram Type 3 personality traits of ambition, adaptability, and a knack for achievement. As the moderator, he skillfully manages the ideological spectrum, facilitating dynamic discussions while maintaining harmony and camaraderie among the hosts.

His self-proclaimed title as the ‘world’s greatest moderator’ underpins his Type 3’s desire for achievement and recognition. He artfully directs the conversation, allowing each participant to express their views, demonstrating his adaptability, a key trait of Type 3.

The playful tension between Calacanis and Sacks adds a unique dynamic to the podcast, showcasing Jason’s charm and charisma, characteristic of his Enneagram type. His firm stance on his beliefs reflects his determination and persistence, while his ability to shift from serious debates to laughter underscores his flexibility.

There’s an underlying ambition within Jason that once resulted in him being jokingly accused of trying to take over the podcast, indicative of Type 3’s desire for success. Yet his respect for the team dynamic and focus on their friendship shows a healthy ability to manage this ambition, further illustrating his Type 3 traits.

Jason’s Enneagram Type 3 personality deeply informs his role and impact on “The All In Podcast,” balancing ambition, adaptability, and a drive for recognition, creating a captivating dynamic that fuels the show’s success.

How Each Enneagram Type Perceives Jason Calacanis

To provide a broader perspective, let’s examine how individuals of each Enneagram type might perceive Jason Calacanis:

  • Type 1- The Perfectionist - They may admire Jason’s ambition and success but might be critical of his occasional dominance in the “All In Podcast.” They’d wish for more balanced participation.
  • Type 2- The Helper - They could appreciate Jason’s ability to facilitate discussions on the podcast but may find his relentless drive for personal success a bit overwhelming.
  • Type 3- The Achiever - Fellow Achievers would likely look up to Jason as a role model, resonating with his pursuit of success and influence in the tech startup scene.
  • Type 4- The Individualist - They might find his emphasis on external achievement a bit shallow, yearning to explore his personal experiences and emotions deeper.
  • Type 5- The Investigator - Investigators would likely appreciate Jason’s insightful commentary on the podcast and his ability to grasp complex business concepts. However, they may crave more depth and less dominance in the conversation.
  • Type 6- The Loyalist - They would value Jason’s commitment to the podcast and his entrepreneurial pursuits but might be wary of his power moves and ambitious nature.
  • Type 7- The Enthusiast - Enthusiasts would probably admire Jason’s energetic personality and his ability to juggle multiple roles successfully - investor, podcast co-host, and entrepreneur.
  • Type 8- The Challenger - They’d likely respect Jason’s assertiveness and determination to maintain influence on the podcast, appreciating his stand for his beliefs.
  • Type 9- The Peacemaker - Peacemakers might feel uncomfortable with the tension that occasionally arises from Jason’s interactions with his co-hosts but would appreciate his efforts to steer the conversation towards constructive and engaging discourse.

The Call To Action

Now that we have made the case for Jason Calacanis being an Enneagram Type 3, has there been any shift in your opinion of him? Personalities are multi-faceted, continually evolving constructs, and our views of others should be ready to shift and give way to empathy when we realize we all have different strengths and weaknesses. What other layers of Jason were missed?

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