Politico thinks it caught novice political candidate Caitlyn Jenner in a “gaffe” when she tweeted her disgust with San Francisco DA Chesa Boudin’s decision to release a repeat domestic abuser who went on to murder a 7-month old baby. Boudin’s handling of the case has drawn the outrage of local domestic violence victims’ advocates and attracted international news.

So what did Jenner do wrong? Her “gaffe” was supposedly that she revealed ignorance of how local DA’s come to power when she wrote “Gavin’s District Attorneys are releasing dangerous criminals back on our streets. Enough is enough.”

Jenner quickly clarified in…

Should Big Tech be allowed to cancel the First Amendment?

Yesterday I was interviewed on the Ricochet Podcast to discuss the deplatforming of Trump and Parler and more generally the status of our free speech rights in the era of Big Tech monopolies. What follows is a transcript with minor edits for length and clarity.

Please note:

  • I recognize that in a crisis, emergency measures are warranted, especially to prevent violence, which happened when Trump supporters stormed the Capitol in a unique outrage to our democracy.
  • I’m talking here about decisions to permanently ban or deplatform individuals and/or businesses with no ability to appeal. …

Chesa Boudin’s Decarceration Disaster

Her name was Hanako Abe. Raised in Fukushima, Japan, she lived through the devastating 2011 tsunami and subsequent nuclear disaster and emigrated to America to attend university. After graduation in 2018, she settled in San Francisco and worked in commercial real estate. She posted a smiling selfie on Instagram Thursday, announcing her excitement for a new year she would not live to see. Shortly after 4 PM Thursday, she was struck and killed by a hit-and-run driver while walking in the SOMA district of San Francisco, just 27 years old. Another woman, Elizabeth Platt, 60, was killed alongside Abe.


The First Amendment Provides a Path to Peace for Social Media

Once again, the CEOs of Twitter, Facebook, and Google found themselves in the hot seat on Capitol Hill last week, grilled by the Senate Commerce Committee. As I predicted in my last post “RIP Section 230,” Twitter and Facebook’s ham-handed censorship of the NY Post has cemented a bipartisan consensus that these tech behemoths are too large and powerful, pose a threat to democracy and free speech, and need to be reined in for the good of America. …

How Rudy’s Hard Drive Could Crash the Open Internet

The internet freedom we have long enjoyed owes a tremendous debt to Section 230 of the Communications Decency Act, a 1996 law which greatly aided the development of the Internet by enabling user-generated content. Suddenly, this visionary provision is gravely imperiled by a tragedy of errors committed by all three of the major actors in the Hunter Biden hard drive story — the New York Post, the social media companies Twitter and Facebook, and conservative legislators who want to take action against them.

The Post erred first by publishing a story

You think you need a COO. What you really need is an operating philosophy.

Let’s face it: most startups are a shitshow. Perhaps the most pervasive problem afflicting venture-backed startups, once they achieve a basic level of product-market fit, is managing the organizational chaos that results from rapid growth. Almost by definition, this is a chronic challenge of Series A-C stage startups since the rapid expansion of the team to chase a new market opportunity is the purpose of that venture funding in the first place. During this time, the growing pains of the startup will reach such a crescendo that the founders and board will cry out as one, “we need a COO!”

Today Craft Ventures is excited to announce that we are leading the $35 million Series A in ClickUp, and I will be joining the board. This is one of our largest Series A investments to date, which reflects our confidence in the team and product.

ClickUp is a team collaboration platform offering tools like task management, docs, wikis, chat, and integrations with dozens of popular tools. Collaboration is a crowded space, with lots of startups competing for users and mindshare, so what made ClickUp stand out? A few unique characteristics that we’ve never seen before in a Series A startup.

Lessons on building startups during a downturn

Harry Stebbings was kind enough to have me on his podcast The Twenty Minute VC. That episode dropped today and you can listen to it here:

Here are some of the topics we talked about:

1) Building startups in the time of COVID

On creating startups during an economic crisis:

Innovation doesn’t stop during a downturn. My own experience was that the two unicorn companies I was involved in creating were primarily built during downturns. PayPal started in 1999, but it was really built in the wake of the dot com crash in 2000–2001. We IPO’d in 2002. Similarly Yammer started in the wake of the 2008–2009 economic crash. So my experience with downturns has…

Photo Credit: clutchpoints.com

ESPN’s new series The Last Dance is an extraordinary behind-the-scenes look at Michael Jordan’s sixth and final championship run in 1998. Through flashbacks it also tells the story of Jordan’s career and the Chicago Bulls’ dynasty that dominated the NBA in the 1990s. It is full of lessons not just for basketball fans but for anyone who wants to build something great. Here are the lessons that should resonate with founders:

1. Expect to be under-estimated.

Jordan was cut from his high school varsity team as a sophomore. But instead of quitting, he used his frustration as fuel to get better. Later, after winning a…

How Startups Should Think About Capital Efficiency

As the economic crisis deepens, capital efficiency becomes a more pressing issue for startups. Not only is it necessary to maximize runway, it also plays a larger role in how investors evaluate companies. While growth is always prized during good times or bad, investors increasingly scrutinize burn and margins during downturns. Startups whose burn is too high relative to their growth will find it hard to fundraise. Founders should be prepared for this shift in emphasis. This post provides a framework for how to think about capital efficiency.

How to Measure Capital Efficiency

Two simple ways to measure capital efficiency…

David Sacks

General Partner and Co-Founder of Craft Ventures. Previously: Founder/CEO of Yammer. Original COO of PayPal.

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