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Most companies have executed on defensive plans to get through the COVID-19 pandemic. Playing defense is about two primary things:

  • Reduce burn and extend runway. This includes taking a microscope (and then a hatchet) to every cost line item on the income statement: lowering headcount costs through some combination of salary cuts, RIFs and furloughs; renegotiating.supplier and real estate contracts; reducing unnecessary outlays, and other similar measures. Headcount is the biggest opex line item for most companies, so that’s where most companies naturally tend to focus focus, though it’s worth emphasizing that you should never, ever lay off your A-players.


The other day, I was meeting with the CEO at a company I advise. Our goal for the meeting was to review his executive team to identify potential gaps.

The CEO pulled up the list of his C-level executives and started walking me through it. I stopped him abruptly.

“What about Kent?” I asked.

“Ah, Kent,” he said, with just the slightest hesitation. “We had to let Kent go.”

“But, but, …” I stammered. “You just hired him three months ago! He was your prized hire, the one whose hiring you trumpeted in an email to the board and advisors…


Yesterday, one of my portfolio companies died.

They haven’t formally dissolved the company yet, but that step is merely a formality. The other events foreshadowing company death are firmly in motion: employees are actively interviewing (many had offers within a week, this being Silicon Valley circa 2019), investors have already told their CPAs to write off the investment, the landlord has been informed, etc.

Two years ago, when I invested in their seed round, the company was full of promise. The two founders were strong technologists with a product bent; both had worked together at their previous employer; they had…


CEOs wear several hats — strategic, operational, financial. In One On One, Ben Horowitz makes a profound statement:

“Perhaps the CEO’s most important operational responsibility is designing and implementing the communication architecture for her company.”

My goal for this post is to dig deeper into the communication architecture that Ben refers to: why it matters in the first place, and what its constituent components are. (Ben — if you read this, would love your thoughts on whether I’m missing something!)

Why communication architecture matters

A good communication architecture enables information to flow across the company (up and down, side to side) without impediment. It…


I got this email recently from a CEO:

Hey Gokul, I want to start a biweekly newsletter to the entire co. I read your blog post on all hands. Was super helpful. Do you have any guidance or examples on how to best structure a regular written update?

In a previous post, I talked about a company’s communication architecture being the CEO’s most important operational responsibility.

Spurred by the CEO’s request and following up on the earlier post, I’d like to deep dive into a specific element of a company’s communication architecture: a weekly or fortnightly email from the CEO…


CEOs wear several hats — strategic, operational, financial. In One On One, Ben Horowitz makes a profound statement: “Perhaps the CEO’s most important operational responsibility is designing and implementing the communication architecture for her company.”

My goal for this post is to dig deeper into the communication architecture that Ben refers to: why it matters in the first place, and what its constituent components are. (Ben — if you read this, would love your thoughts on whether I’m missing something!)

Why communication architecture matters

A good communication architecture enables information to flow across the company (up and down, side to side) without impediment. It…


A common question I get from students or folks early in their career (or sometimes, even mid-career) is some variant of: “How should I choose a company to work for?”

Over the years, I’ve given this question some thought. Hindsight being 20/20, I’ve also looked back at why I decided to join Google, Facebook and Square. All three companies have been successful by almost any metric.

So what did I uncover? My assertion is that you need to evaluate a company through the dual lenses of Purpose and Leader/Purpose Fit.

  1. Purpose: Every company has a purpose, a raison d’etre, a…


“My biggest regret is that our first customer was $1M ACV*,” my friend lamented over coffee the other day. “I wish I could take it back.”

“Why? What do you mean?” I asked, perplexed. He is the CEO of a company that recently raised a Series C from great investors, is growing rapidly, has strong customer retention and a top-notch leadership team. I was — to put it mildly — taken aback.

“Ever since that first customer, our product, go-to-market, our support model have all been pulled in one direction — high-end enterprise,” he said. “Our first $1M ACV customer…


What’s the second most important metric for every company?

Let’s start by clarifying the most important metric for every company.

It is the North Star Metric (NSM), which Sean Ellis elegantly defines as the “single metric that best captures the core value that your product delivers to customers.” Facebook’s NSM is Daily Active Users (DAUs), which captures value delivered to users; Square’s NSM is Gross Processing Volume (GPV), which captures value delivered to sellers; AirBnB’s NSM is Nights Booked, which (since AirBnB is a marketplace) captures value delivered to both hosts and guests.

The North Star Metric is necessary and…


Most CEOs are an urgent breed.

Every CEO I know laments how they need to instill a stronger sense of urgency in their company around every single thing, to get things done faster.

However, there is one very important thing they should have zero urgency around.

In fact, they should try to delay it as much as possible; ideally, forever.

I’m talking about titles. Specifically, Director-level and higher (Senior Director, VP, SVP) titles.

I’m talking about building a company of several thousand people where not one person is a Director, Senior Director, VP, SVP or EVP.

I’m talking about building…

Gokul Rajaram

curious optimist. quizbowl coach. dad and husband. caviar lead @ doordash. previously square, facebook and google.

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