Part I: Founders need squads

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 IPart IIPart IIIPart IVPart VPart VI.

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How Founders Become Learning Animals

Silicon Valley has long exalted a singular classic founder story that supposedly spells success. It goes something like this: “This founder grew up taking apart computers and taught himself to code as a kid. They attended an Ivy League university, dropped out midway, started a company in their garage, and became a unicorn sensation in the following years.”

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THAT founder narrative. You know.

These narratives, while accurate for a handful of individuals, create niche stereotypes about Silicon Valley founders and gloss over the hard work of intentional self-development and growth required to evolve from a startup founder to a leader in a large organization.

Successful founders are made, not born, and their self-development journeys are fascinating paths, rarely chronicled.

Silicon Valley often talks about “learning animals” — founders who can seemingly learn anything. Below are six common themes of founders who are learning animals.

While I was a student at Stanford’s Graduate School of Education I set out to unearth the key mental shifts and developments founders go through as they grow into world-class leaders, as they become learning animals. I interviewed nearly 45 founders, VCs, and executive coaches. Here’s the six most common themes they told me:

  1. Founders need squads
  2. Asking questions is a skill
  3. Self-Awareness must become a routine
  4. Navigate advice overload with frameworks & conviction
  5. Scale yourself in phased mindset shifts
  6. Breaking the “Vulnerability <> Confidence Tradeofff” Myth

I’ll be rolling these six key insights in separate posts. Below are founders’ stories, the battle tested tales of how they learned to meet the challenge of running their scaling company, all while steering the company and employees to accomplish the mission.

To the founders — I’m so honored you shared your innermost thoughts with me and are allowing me to share them with the broader community. Thank you again a million times over. Enjoy!


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1. Founders are Made not Born — Founder Squads

Being a founder can be a lonely job. Founder squads are groups of peer founders that almost all founders rely on as a key self-development resource.

Again and again in our interviews, founders told me that having a peer group was their most valuable learning resource. More valuable than mentors, books/articles/podcasts, executive coaches, VCs (imagine that!), parents or spouses.

There were many questions founders simply couldn’t ask their board members. Sometimes, because asking a board member felt risky. Other times, because the board members simply wouldn’t know. Knowledge expires quickly, so even VCs that were founders 10 years ago may not be able to help with a new challenge, like working from home. There’s no playbook for founders on self improvement, so founders need to rely on each other to “see around the corner.”

In academia, we would call these peer groups a community of practice for founders who engaged in collective learning. Founders described with great specificity how they got the most out of their peer groups by ensuring they had different groups based on 1) relative stage (how far ahead of me are the rest of the founders in this group) and 2) domain (how they utilized each group). More seasoned founders carefully constructed their founder squads.

When developing their squads, founders like to include others who are a bit ahead of them:

“I credit my growth first and foremost to a community of other founders who were 12 to 24 months ahead of me. People who are the same peer level as you don’t work — this is just the blind leading the blind.”

Kelly Peeler, Founder of NextGenVest

Founders determine how far another founder is ahead of them based on revenue, capital raised, and team size:

“Talking to other founders or people who have been one step ahead of you / seen around the corner has helped me the most. Normally whatever stage we’re at and one step ahead of those. I measure who is one step ahead by the 3 metrics that matter: revenue, money raised, and team size. Doesn’t matter if they’re in my industry or not.”

Rachel Carlson, Co-founder & CEO of Guild Education

A founders’ go-to person can be based on specific types of problems they’re trying to solve:

“I categorize who I go to for what. For scaling and growing / operating a tech business — I talk to one group. On EQ — I have a coach that I speak with every week, who helps me make different decisions and manage my own psyche. For personal leadership, inspiring my team, I have another group I turn to. On domain expertise, I speak to ….”

Ryan Williams, Founder & CEO of Cadre

And it’s not just one squad….

“I have a diverse portfolio of learning resources — there is so much going on that you need a lot of resources for a lot of problems.”

Kristen Jones, Co-founder & CEO of Mented Cosmetics

Sometimes they talk about the big, course-altering decisions…

“I talk to them less about tactical challenges, and more about feelings I am working through, issues I am stressed about, and the biggest decisions I am thinking through.”

Chris Bennett, Founder & CEO of Wonderschool

And sometimes they’re chatting tactical, smaller decisions:

“With first time founders who are also in the pit — I talk with them about 1) more immediate tactical problems — what did they do last week that I need to do — for example setting up a bank account or 2) how are we going to survive mentally or emotionally.”

Devin Lennon, Founder & CEO of Death Doula Devin

Generally they seemed to prefer hearing tactical stories:

“The most impactful way to give advice is to share your own experiences with a similar or related situation. Share the story behind the advice instead of the actual advice. More often than not simply telling someone what they should do is woefully ineffective.”

Alexander Muse, Sumo Ventures

Founders, coaches, and VCs alike acknowledged that having more tangible examples of founder success are most helpful:

“Studying Michael Jordan or Mark Zuckerberg is not helpful. Studying someone who is one step ahead of you as a founder is really helpful. We overly study the lives of really exceptional people. You should get someone 12–18 months ahead because a founder’s knowledge becomes irrelevant really quickly.”

Enhao Li, Co-Founder of Female Founder School

As discussed above, even a founder’s investors or advisors have operational experience, it still helps to have a founder squad:

“I learn the most from peer founders. I went into this thinking our investors and advisors would be who we leaned on the most, and they’re helpful for many things, but they don’t tend to help with questions like “how do I build culture on my team” whereas a founder will say ‘when I went from a team of 2 to 6 this is how I thought about culture’. I have a group of investors who are all prior founders so theoretically I should be able to turn to them more for founder questions but I don’t because recency matters and relationship matters. The relationship with other peer founders is stronger because we’re going to the same events, speaking on the same panels, etc. Recency and familiarity. I see founders who are in the idea stage who are reticent to reach out to other founders because they think someone will steal their idea. That won’t work in the execution phase.”

Kristen Jones, Co-founder & CEO of Mented Cosmetics

Founders also described how paying it forward helped entrench their own learning:

“It’s like tennis — you should play with people who are better 30% of the time, worse than you 30% of the time, and the same level as you 30% of the time. If you play with people better than you all the time you lose your confidence. You play with people worse than you so you know how to ‘close out matches.’ It cements learning and instills confidence around winning.”

Sarah Hoffman, Co-founder & CEO of MakerWine

Sarah’s tennis insight resonated with me because in educational academia, learning by teaching is viewed as one the most effective learning methods because of the “testing effect” — recalling what you’ve learned helps cement it.

As a venture capitalist, I now look for founders who’ve surrounded themselves with a strong peer group of founders and who take the time to give back to earlier stage entrepreneurs. Often with my earliest stage portfolio companies, it’s one of the first areas I encourage them spend more time strengthening.

Founders, I see you with your squads. I’m so glad you have them and love the intentionality with which you surround yourself with the people you need to thrive.

I’d love to hear any more insights you’ve gained about how to form the most effective founder squads or other things that have helped you become the leader you are today. Reach out anytime at

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