Founders are Made, Not Born: How Founders Become Learning Animals (Part III)

Part III: Self Awareness Must Become a Routine

This is the “Founders are Made, not Born: How Founders Become Learning Animals” series, based on my Stanford Masters of Education research about founders & learning. Part I, Part II, Part III, Part IV, Part V, Part VI.

How Founders Become Learning Animals

Self-awareness is an often-cited, universally-exalted trait that seemingly the best humans possess. Every self-help book or enlightenment journey will in one way or another tell you to start with self-awareness. We all know it’s important.

So it’s no surprise that when I interviewed nearly 45 founders about how they grew to be the leaders they are today, they (unprompted) consistently pointed to self-awareness as the most important characteristic to adopt. More so than motivation, humility, grit, growth mindset, or the willingness to be wrong.

So what’s unique about how founders practice self-awareness? For developing leaders it informs executive team construction, organizational structure, shaping culture, and perhaps most importantly, it’s a muscle in need of constant development less it becomes weak.

Founders described how self-awareness requires accepting your strengths and weaknesses:

“You don’t have to know everything — for example there are functional areas where my teammates may have greater expertise. But I always did have a good sense of my gut and ability to make a decision.”

Megan O’Connor, Founder of HiClark

And a sense of humility….

“The more I mellow in age, the more I realize I have to learn.”

Philip Rosedale, Founder of SecondLife & High Fidelity

For many founders, self-awareness helps them identify gaps in their abilities:

“Good founders quickly understand they don’t know what they don’t know and ask ‘How can I get someone to teach me as quickly as possible’.”

Kelly Peeler, Founder of NextGenVest

Some founders harness their self-awareness and systemize the collection of inputs to help them become even more self aware, identifying in a way that self-awareness is a moving target, not a static asset:

“In a desire to scale myself, I frequently reflect and try to know when I can’t do something better myself anymore. I also ask for feedback from reports constantly. Every 1v1 or review cycle when we sit down, I want to know how I’m doing.”

Meg Whitman, Founder of Quibi, CEO Ebay

Self-awareness also seemed to be the key to optimizing organizational structure:

“As a founder you’re trying to optimize for ‘who I am’ as a person — it’s not like school where you learn about how to be the best lawyer. The first step is figuring out “what is ‘me’,” what do I contribute — Peter Drucker captures this well. The second part is building on that — “what do I need to learn to be even more successful?” For me, a really hard thing to understand was figuring out what to delegate — lots of founders think “I’m good and can always learn to do something” but that hurts your team — you need to be really ruthless about what you’re good at.”

Sumorwuo Zaza, Founder of NICKL

One of my favorite insights was about how a founder’s self awareness can set the foundation for an emotionally-safe work culture:

“Self-awareness is the best resource a founder can have. It allows them to foster a culture of emotional safety so direct reports feel safe telling founders how you’re doing. As a founder you need to know what problems you have.”

Alan Chiu, Co-Founder and CEO, Enya

Alan’s words hit home because as an operational leader, I have reflected that my natural style will become my team’s culture — and that’s not always the best for the team. Self-awareness helps you realize which aspects of your style should inform the company culture and where the organization can adopt other’s cultural inputs.

I was also really intrigued by how founders created opportunities to become self-aware. As someone explained to me, being at the top of their organization, it’s easy to not receive complete feedback. Asking for feedback constantly can lower the fear some employees may have in giving candid feedback.

As a venture capitalist, I love meeting founders whose self-awareness shines through. It often shows in our first interactions when they talk about their team and any roadblocks they’ve encountered.

Founders, I’d love to hear any more insights you’ve gained about your own self-awareness and how you’ve utilized it to become the leader you are today. Reach out anytime at




Hard work is never overrated. Always curious.

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Mercedes Bent

Mercedes Bent

Hard work is never overrated. Always curious.

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