Chamath Palihapitiya: The Underdog’s Mentor

Cal Chan
The Startup
Published in
4 min readFeb 24, 2021


A man trained in the art of waiting and building a strong chip lead

We are exceptionally lucky to live during a time when the world’s smartest people can share their knowledge openly and honestly. These people put themselves out there as mentors, and I consider Chamath one of the greatest mentors on Youtube.

Last week he recently appeared on my Youtube feed. I had no idea who the man was, but the video was titled “Chamath Palihapitiya: Early days of Facebook, working for a 19 year old Zuckerberg”.

I found it fascinating. Not because it was ripe with business ideas and key insights that could help my startup. What stuck with me was the stories he told about growing up, being chaperoned to his first professional job by his mentor, and feeling that for the first time he was talking to a real human being.

I’ve always been a fan of long-format conversations on YouTube. In the instance of Chamath, YouTube chronicles a number of insightful and candid interviews and lectures he’s given on a variety of topics, almost always tuned around business but never only about business. In all of his videos he speaks with clarity and passion. He’s magnetic. But he’s also very human.

Chamath Palihapitiya comes from humble beginnings. His narratives about coming from a working-class Asian immigrant family struggling to make ends meet struck a cord with me. He has an interesting story that includes a parent who reminds me of my own dad. It also includes some very interesting career development, a lot of which came to fruition at Facebook, but was deeply informed by a prior life and career at companies that were bottle-necked by clogged infrastructure and corporate politics.

This is the story of Chamath Palihapitiya that I discovered: Born in Sri Lanka, grows up in Canada and then moves to the U.S. to attend college. Despite a lack of direction, finds his way into the tech industry by way of options trading. Works at AOL as product architect on ICQ and AIM, where he develops a core competency in corporate problem solving but frequently hits structural barriers. Is offered a job and becomes an executive at Facebook through his interactions with Zuckerberg at AOL.

The first thing he does is to implement systems for growth (that end up being used by the entire company). Then he builds new products that help drive Facebook’s growth even further, primarily for their mobile expansion. Gets bored with Facebook and leaves to pursue other opportunities (like owning the Warriors, playing poker, creating investment funds, figure out his meaning for being).

That’s an impressive resume, isn’t it? But it doesn’t tell you why Chamath Palihapitiya would be a great mentor, does it? Let’s dig deeper: Chamath Palihapitiya is focused on growth. He knows that to have an impact you have to grow something big. Something really big. He also knows that getting there means changing your life and making some hard decisions along the way. That’s what he did and it worked for him, and at the core of his OS from the his humble roots in Canada.

When he arrived at Facebook he knew that its focus was on growth and that he needed systems in place so that growth could take place quickly on a global scale. So what did he do? He put systems in place that were designed to quickly grow the company as a whole (see: The Hacker Way). And because they worked well, they’re still used today and are part of the reason why Facebook has grown as fast as it has.

The other striking thing about Chamath is self-awareness. The greatest mentors are those who understand and have a perspective, and Chamath’s is one that is constantly evolving and tuning itself. You can tell he’s measuring his approach to conversations while remaining as candid as possible to win the respect of those like me who would follow him, as well as the powers that be from which he needs support for his broader ambitions. He is an incredible tactician, likely why he’s also an avid poker player, and observing how he navigates the interviews he grants offers deep insights into what being a “free-spirit” means within the confines of several billions of dollars in obligations.

TL;DR: Why do I consider Chamath a mentor worth listening to?

  1. He has an ethical set of core values. He’s not a bandwagon jumper, and he has his own view of the way the world works and should be.
  2. He’s not afraid to tell you what he thinks, and also self-aware enough to backtrack on things he believes need to be under-written for the sake of his leadership goals, and out of respect for his colleagues and employees.
  3. He has a good track record. He spent his time at creating significant value.
  4. But most importantly, he seems to have a clear and evolving point of view on what’s going on in the world right now and hearing his perspective can help inform your own point of view. This is all to say that I trust Chamath to be thinking about things that are important to me and have some interesting views on how we should approach them.

To Chamath, and to others like him, putting themselves out there for the sake of educating and informing, thank you, and more power to you!

Cal Chan is the CEO of Engaging, President of Trilogía, and Co-Founder of Vitamin Bounty and Active Wow.