Jason Calacanis

Jason Calacanis

Published Feb 17, 2015

Legendary entrepreneur David Sacks replied to my blog post “My job: never underestimate anyone” with a particularly pointed tweet:

Not-so-legendary entrepreneur, but absurdly-legendary investor Shervin Pishevar dubbed the tweet “Sacks’ Law,” which I found worthy of consideration and memorialization here on the blog.

[ Click to Tweet (can edit before sending): http://ctt.ec/5QVfA ]

Let’s soak in the two parts of what he said for a moment:

  1. “If you want to bet on startups based on what they could be…”
  2. “... you gotta see founders for who they could be.”

This is particularly important for the “media” to understand, as they frequently judge founders harsher than they do their products. Now, I use the word “media” here because I’m defining two groups of people who create content: a) real journalists, and b) news-as-entertainment content creators.

Why the distinction? Because folks who are doing SCREAMING-BUT-NOT-FACTUALLY-CORRECT headlines like Pando, or TechCrunch’s pathetic process journalism, “We don’t check facts, we publish first and let the audience tell us if it’s true!” shouldn’t be counted in the same league as “journalism” in the way the slow, methodical, and boring (aka the truth!) journalists like Re/code, The Information, and the New York Times.

If Sheryl Sandberg or Sean Parker judged that college dropout who put “I’m CEO, bitch!” on his business cards and screwed all his partners as … whatever ... then we would have never seen Zuckerberg’s growing legacy -- or his better angels.

I’m not going to defend the long list of “founders with a history,” but we all know that few of us stand up to the worst moments in our younger days -- founders of startups, investors, or journalists (or those of us who are all three). Also, we all need someone to believe we can be more than we are.

Phil Jackson believed in Michael, Kobe, Shaq, and now Camelo -- all imperfect and frequently derided when the Zen Master believed in them.

Angel investing is an art, where you look at a nascent product which any sane person would find immature and unlikely to succeed, and say to yourself, “But what if it did?”

That’s the same exercise you have to do with individuals. Sure, this scrappy extrovert or introvert, from Brooklyn or Nebraska, is underwhelming or awkward, but what if his/her polish and presence caught up with the drive?

I sometimes draw this chart for young entrepreneurs (or the older ones who are in a rut). I’ll then draw entrepreneurs we all know in these five moments in time. The goal is to get to the upper right corner, where your humility is greater than your execution -- which is a hard task for successful people and/or egomaniacs. I think you all know where I’ve spent most of my career, but I can tell you I’m working on getting to that top right.

When you do get to the top right everything in life clicks: people start rooting for you, you start rooting for you, and you sleep well at night. The night terrors, the teeth grinding, and the fights just, well, go away.

Namaste, @jason

More articles by Jason Calacanis

  • Founder x Angel University Tokyo

    Nov 20, 2025

    Founder x Angel University Tokyo

    In Founder University, we help Year Zero founders build MVPs, raise money, and find their first customers. After…

  • Come work for me!

    Nov 17, 2025

    Come work for me!

    After the success of Founder University in both America and Saudi Arabia, we’re expanding to Japan! We’re hiring a…

  • 50% off JCal’s Angel University!

    Sep 28, 2025

    50% off JCal’s Angel University!

    Reminder! I’m hosting my next virtual Angel University workshop on October 7th. This is a 4-hour live workshop where I…

  • Angel University is back!

    Aug 21, 2025

    Angel University is back!

    Friends, We’re hosting the next virtual Angel University workshop on Tuesday, October 7. It’s a 4-hour live workshop…

  • Sanabil Founder University by LAUNCH

    Jul 7, 2025

    Sanabil Founder University by LAUNCH

    Friends, Three years ago, I started to make trips to “the Region.” For a decade, my friends in technology and finance…

  • Come build with us at Founder University!

    Feb 27, 2025

    Come build with us at Founder University!

    Friends, We're officially one month away from kicking off Founder University Cohort 10! We'd love to learn more about…

  • Turn your startup idea into a reality in 12 weeks

    Oct 6, 2024

    Turn your startup idea into a reality in 12 weeks

    Friends, We're officially three weeks away from kicking off Founder University Cohort 9! If you're a team of 2+ builder…

  • The LIQUIDITY Summit, Napa, June 2-5th

    May 23, 2024

    The LIQUIDITY Summit, Napa, June 2-5th

    The LIQUIDITY Summit (fka "The Angel Summit") is in two weeks in Napa: June 2-5th. ~ 130 GPs, LPs and angel investors…

  • Turn your startup idea into a reality in 12 weeks

    Apr 12, 2024

    Turn your startup idea into a reality in 12 weeks

    Friends, We’re excited to announce that applications are open for Founder.University Cohort 8.

  • The greatest moment to start a company? Right Now!

    Dec 11, 2023

    The greatest moment to start a company? Right Now!

    Why? Four reasons..

Others also viewed

Explore content categories