Jason Calacanis's Personality as the Startup World's Achiever

Jason Calacanis

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

We are all the stars in our narratives. We are all driven to succeed, some more than others.

Jason Calacanis is one of those people who cannot stand to be anything but the epitome of success in everything he does. He wants to make a mark on the world and is willing to reinvent himself again and again to accomplish this.

Jason is an Enneagram type 3, also known as ”The Achiever.”

Jason Calacanis: An Embodiment of The Achiever?

The Many Hats of Jason

Jason is an angel investor and the host of two prominent podcasts: ”This Week in Startups” and ”All In”. He also runs a startup accelerator called “Founder University”. 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.

The Drive Behind the Success

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 likely 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 extraordinary personal achievements. However, their need to be successful is born out of a fear of worthlessness.

When they are not achieving or are very stressed, type 3s may become disengaged and lethargic. On the other hand, when they are achieving, growing, and feeling their best, Threes become more cooperative and committed to others.

Jason Calacanis: Tracing The Achiever’s Path

From Humble Beginnings to Tech Mogul

Jason’s journey is a testament to the Achiever’s relentless pursuit of success. He started as a reporter covering the “internet industry” during the dot-com boom. When the bubble burst, many would have been discouraged, but not Jason. Instead, he saw an opportunity to reinvent himself and climb the ladder of success.

Rising from the Dot-Com Ashes

After the dot-com crash, Jason worked tirelessly to establish himself as a startup founder. His first major triumph came with co-founding Weblogs Inc., a network of niche blogs. This venture caught the eye of tech mogul Mark Cuban, who invested in the company. Just two years later, in 2005, Jason sold Weblogs Inc. to AOL for a reported $25-30 million, marking his first significant exit.

The Serial Entrepreneur Emerges

But Jason didn’t stop there. He kept ”upping the ante,” as he would say. His entrepreneurial journey continued with:

1. Founding Mahalo.com, a human-powered search engine, which raised over $20 million in funding.
2. Becoming an early investor in Uber, turning a $25,000 investment into an estimated $100 million.
3. Launching the LAUNCH Accelerator, which has invested in over 300 startups.
4. Co-founding Inside.com, a network of email newsletters.

Each of these ventures showcases Jason’s goal-oriented mindset and knack for achievement, hallmarks of a Type 3 personality.

The Hustler’s Mantra

Jason is a self-proclaimed “hustler” and constantly emphasizes the importance of hard work. As Calacanis often says:

“The secret to success is to work harder than everyone else when you’re young, save your money, and then take massive risks.”

The Charmer and The Professional

Master of Social Dynamics

But Jason is not just a hard worker. He’s a master of socializing and networking. His charisma and ability to read people are quintessential Type 3 traits. The thing about 3s is that they have a superpower - their ability to read a room and interpret 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-reading ability to their advantage.

The Networking Guru

On networking, Calacanis advises:

“The key to networking is to stop networking. Be generous, help people, and make friends instead.”

This approach reflects the Achiever’s ability to adapt and excel in social situations, always with an eye towards building relationships that can lead to success.

Beyond The Glittering Image

The Challenges of an Achiever

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.

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.

Jason’s Impact on “The All In Podcast”

The World’s Greatest Moderator?

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

Balancing Competition and Friendship

The playful tension between Calacanis and David Sacks adds a unique dynamic to the podcast. Jason showcases his ability to shift from serious debates to laughter, highlighting his flexibility. Though he and Sacks don’t always agree, Jason’s loyalty to his friend demonstrates a healthy balance of ambition and relationship-building.

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? Comment below ⬇️