Understanding the Personalities of Visionary and Legacy Founders

Why do certain founders seem to thrive in the dynamic world of mode-shifting while others struggle? The answer often lies in the core personality traits (the psychological DNA, if you will) that help form and shape how these founders think, decide, and lead.

In Part 3 of the Founder Mode Series, we explored the critical importance of being modal-aware, emphasizing how founders who intentionally shift between modes can significantly enhance their effectiveness. We delved into the specific modes founders navigate — like Visionary, Coach, Warrior, and Magician — and underscored why knowing when and how to engage each mode is a superpower. But understanding and mastering modes is just one piece of the puzzle.

In this part of the Founder Mode series, we turn our focus to the personalities behind the 13 essential modes for founders, which I introduced last week. We’ll look at four frameworks that can help us understand how different psychological traits align with the demands of Founder Mode: TypeCoach, The Big Five (OCEAN), Enneagram, and Kolbe.

These tools offer insights into the Visionary and Legacy founder archetypes, helping us understand why certain traits make some founders more naturally suited to thrive in this environment. Keep in mind that what we’re presenting in terms of personalities this week is a starting point — a “straw man” — as there is still a tremendous amount of research to be done to fully grasp the raw nature of founders. Our goal is to lay the foundation for deeper exploration into how personality — the founder's "psychological DNA" — informs founder behavior, especially in the context of shifting modes. We’ll start with TypeCoach. 

TypeCoach

TypeCoach uses a mix of two models of personality, including the Jung/Myers model popularized by the Myers-Briggs Type Indicator® and the four temperaments framework (Rational, Idealist, Artisan, and Guardian — I like to refer to these as Thinkers, Feelers, Doers, and Guardians, respectively) developed by David Keirsey. From an efficacy perspective, I think TypeCoach is much more powerful than either of those other two frameworks because it brings a practical application, answering the “so what” question people usually have with the traditional approach.

TypeCoach and Visionary Founders

Visionary founders tend to be from the Conceptualizers/Rational temperament, which is a combination of Intuition (N) and Thinking (T). This group is naturally driven toward future thinking and strategic analysis while also having an innate desire to innovate, improve, and ultimately make a lasting positive mark on the world around them. If they can leave things better than they found them in a long-term manner, they’re immensely satisfied.

Given their problem-solving abilities and long-term thinking, they excel in Magician Mode and Visionary Mode, where they can innovate and design complex systems. While there’s a mix between Judging (J) and Perceiving (P) types among Visionary founders, there are likely more Intuitive/Judging types in this category, since the Judging preference enables them to execute their vision with precision and discipline. The exception would be areas where the playfulness and adaptability of the Perceiving types are assets.

Examples: Reed Hastings (Netflix), Steve Jobs (Apple), Elon Musk (Tesla, SpaceX)

TypeCoach and Legacy Founders 

Legacy founders typically fall into the Traditional/Guardian temperament category, which is a combination of Sensing (S) and Judging (J). Traditionalists are responsible, structured, and focused on maintaining stability, which makes them natural fits for Caretaker Mode and Builder Mode. They focus on creating sustainable systems and processes that protect their company’s long-term interests. While there’s a mix of Thinkers (T) and Feelers (F) in this group, business tends to attract more Thinkers than Feelers, with the exception being in certain industries where relationships are central to the business.

Examples: Warren Buffett (Berkshire Hathaway), Howard Schultz (Starbucks), Ray Kroc (McDonald’s)

The Enneagram

The Enneagram divides personalities into nine core types. Visionary and Legacy founders often align with Type 3 (Achievers) and Type 8 (Challengers).

The Enneagram and Visionary Founders

Type 3 Achievers are driven by success and are highly adaptable. They are goal-oriented and thrive on challenges. This allows them to excel in Visionary Mode and Magician Mode, where they can pivot quickly to pursue opportunities and overcome obstacles.

Examples: Oprah Winfrey (OWN Network), Jeff Bezos (Amazon), Sara Blakely (Spanx)

The Enneagram and Legacy Founders

Type 8 Challengers are natural leaders, assertive, and focused on controlling their environment. Legacy founders, who often embody this type, excel in Builder Mode and Caretaker Mode, where their drive to create lasting impact helps them protect and grow the company over time.

Examples: Jack Dorsey (Twitter, Square), Larry Ellison (Oracle), Andrew Carnegie (US Steel)

The Big Five (OCEAN)

The Big Five (OCEAN) model — Openness, Conscientiousness, Extroversion, Agreeableness, and Neuroticism — provides a granular understanding of founder personalities.

The Big Five and Visionary Founders

Visionary founders score high in Openness and Conscientiousness. Their openness drives them to explore new ideas and push boundaries, allowing them to thrive in Visionary Mode and Magician Mode, and their conscientiousness ensures they can execute those ideas effectively. Interestingly, many Visionary founders are also low in agreeableness, meaning they’re more willing to challenge the status quo and engage in difficult conversations — an essential trait in Warrior Mode when tough decisions need to be made.

Examples: Steve Jobs (Apple), Elon Musk (Tesla, SpaceX), Jeff Bezos (Amazon)

The Big Five and Legacy Founders

Legacy founders score high in Conscientiousness and Extroversion. Their conscientiousness enables them to build solid, long-term systems, making them natural fits for Builder Mode and Caretaker Mode. Their extroversion helps them lead teams and manage external relationships, making them effective in Politician Mode as they advocate for the company’s long-term vision.

Examples: Bill Gates (Microsoft), Howard Schultz (Starbucks), Richard Branson (Virgin Group)

The Kolbe A Index

The Kolbe A Index assesses instinctive strengths across four dimensions: Fact Finder, Follow Thru, Quick Start, and Implementor.

Kolbe and Visionary Founders

Visionary founders score high in Quick Start and Fact Finder. They’re adept at taking quick action on new ideas, and their fact-finding instinct helps them gather the necessary information before making decisions. They are strong in Visionary Mode and Magician Mode, where fast, intuitive decision-making is essential.

Examples: Reed Hastings (Netflix), Elon Musk (Tesla, SpaceX), Travis Kalanick (Uber)

Kolbe and Legacy Founders

Legacy founders score high in Follow Thru and Fact Finder. They excel in Builder Mode and Caretaker Mode, thanks to their strong follow-through. They are methodical, ensuring systems and processes are in place for long-term success, and their fact-finding ensures these decisions are data-driven and well-considered.

Examples: Warren Buffett (Berkshire Hathaway), Phil Knight (Nike), Henry Ford (Ford Motor Company)

Truly Understanding Founders

While these frameworks offer valuable insights into the personalities of Visionary and Legacy founders, it’s important to remember that we’re only scratching the surface. There’s still a tremendous amount of research to be done to fully understand the complex personalities of founders and how we operate in different modes. That’s why I called this a “straw man” — it’s a starting point for deeper exploration into the raw nature of Founder Mode.

By examining the personalities of Visionary and Legacy founders through these lenses, we can better understand how we navigate different modes.

But here’s the thing: Not all founders are in startups. Many of us operate within larger companies, using these same traits to innovate, lead, and drive change from the inside. This Founder’s Mindset can be found at every level of an organization, not just in those businesses us founders start ourselves.

Up Next…

In the next part of the Founder Mode series, we’ll explore how founders show up within large organizations and how individuals who have the Founder's Mindset can have just as much impact working inside a company as those who start one from scratch.

If you want to stay tuned, I encourage you to sign up to receive email updates with each new installment of the Founder Mode Series. I’d also love you to share this with others who are grappling with “Founder Mode,” whether they’re a founder or working with one. I want this series to spark discussions and debates — after all, that’s how we learn and grow. As someone who knows he’s “guilty” of Founder Mode, I’m genuinely excited to explore these ideas with any and everyone who’s interested in this topic.

So… I’m adding this link to my Google Docs draft of this series. I’d love to get your feedback and read stories from those who have experienced the good, the bad, or the ugly of working with one or more founders in Founder Mode. Who knows — maybe this will turn into a book that includes lots of great stories about founders around the world.

Read the rest of the Founder Mode Series:

• Part 1: What Is Founder Mode, Really?
• Part 2: Tapping into the Founder's Mindset
• Part 3: 13 Essential Modes for Founders