Jason Calacanis Enneagram Type 3

Sun Jul 30 2023

We are all the stars in our narratives. We are all driven to succeed, some more than others. Jason Calcanis is one of those people who cannot stand to be anything but the epitome of success in everything he does. He is aching to make a mark and is willing to mold and reinvent himself to accomplish his next goal. Jason is this way, we argue, because we think his personality type is an Enneagram type 3, also known as "The Achiever."

Disclaimer This analysis of Jason Calacanis’s Enneagram type is speculative, based on publicly available information, and may not reflect Jason Calacanis’s actual personality type. Please leave a comment at the end telling us if we hit or missed the mark.

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?

Jason is an angel investor, the host of the ”This Week in Startups” podcast. He also runs a startup accelerator called “Founder University” and hosts another podcast called the “All-In” podcast. To say Jason is busy would be an understatement. He prides himself on his hard work and encourages the founders he mentors to work just as hard.

Why does Jason feel the need to work so hard? Is it because he loves making the world a better place? Or is it because he would feel worthless if he was not successful? The answer is the latter.

The Achiever: An Overview

Type 3s, or Achievers, are characterized by their desire for success and relentless pursuit of their goals and ambitions. They embody the best of a culture, often serving as role models that inspire others to more extraordinary personal achievements. However, their need to be successful is born out of a fear of worthlessness. In another sense, they feel deep shame and are insecure that they are not worthy of love if they are unsuccessful. Somewhere in their childhood, they picked up this message, and now, every time they achieve something, it validates their value.

Threes, when they are not achieving or are very stressed, may become disengaged and lethargic and act like an unhealthy version of another personality type, the Enneagram 9. On the other hand, when they are achieving, growing, and feeling their best, Threes become more cooperative and committed to others, much like healthy Enneagram Sixes.

Jason Calacanis: Tracing The Achiever’s Path

In Jason’s journey, we can observe the hallmark qualities of a Type 3. His entrepreneurial success stories, from Weblogs Inc to Mahalo, stand testament to his never ending ambition. He is a self-proclaimed “hustler” and beats the drum of needing to work hard relentlessly.

The Charmer and The Professional

But Jason is not just a hard worker. If you watch him in interviews or a group setting, he is often the most charismatic person in the room. He is a master of socializing. He is good in front of a camera and frankly enjoys being on camera. Did we mention that he hosts two podcasts?

The thing about 3s is that they have a superpower. Hard work is not their superpower. A three’s superpower is their ability to read a room and read the emotions and body language of anyone they come in contact with. They can sense what you think and feel about them and use that highly tuned people’s reading to their advantage. With that intuition, they can become the person they would like and admire if they so choose. Naturally charismatic people do this, but 3s have finely tuned this people reading ability since they were young, and so has Jason.

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, Jason’s competitiveness and workaholism have rubbed people the wrong way. 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 started as a reporter talking about the “internet industry.”After the dot-com boom, he worked his way up to becoming a startup founder. Jason’s first major triumph was co-founding Weblogs Inc., where he got an investment from Mark Cuban and sold it two years later. He kept upping the anti and later leveraged his skills and insights as an angel investor, scoring wins with companies like Uber. Jason was on a steep incline of growth, showcasing his goal-oriented mindset and knack for achievement.

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

Jason’s impact on “The All in Podcast”

Jason’s influence on “The All In Podcast” is a testament to his Enneagram Type 3 personality traits. He is the moderator. The self-proclaimed “world’s greatest moderator.” He skillfully manages the ideological spectrum, facilitating dynamic discussions while maintaining harmony and camaraderie among the hosts.

This underscores his Type 3’s desire for achievement and recognition. He artfully directs the conversation, allowing each participant to express their views while always getting his 2 cents in.

The playful tension between Calacanis and David Sacks adds a unique dynamic to the podcast. Jason and Sacks started off on opposite sides of the political spectrum; however, the hostility has died down over time. Jason showcases his ability to shift from serious debates to laughter, highlighting his flexibility. They are both poker players and VCs. In the place of political competition now stands a friendship, and though he and Sacks don’t always agree, Jason is loyal to his friend David Sacks and has defended him on multiple occasions.

Jason was jokingly accused of trying to take over the podcast once. There needed to be more clarity on where to take the podcast. Jason wanted to do things to grow the podcast and monetize it; however, the other podcast members wanted to keep the podcast authentic. Jason ended up focusing on the friendship between the podcasters rather than the show’s success. This shows a healthy ability to manage this ambition.

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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