Weekend Briefing No. 364

Welcome to the weekend.

As we’re closing out January—the 13th month of 2020—I’m looking forward to February. Here’s my February playlist for your listening enjoyment.

I don’t talk about my law firm that much here, but I’m excited about something I want to share with you. I’ve been working hard behind the scenes on improving our General Counsel service. It’s an innovative approach to legal for early and growth stage companies. For a flat monthly fee, we provide ongoing legal services for you. We’ve had this product for five years, but based on a bunch of research are revamping it and releasing it to the public soon. I wanted to give you a sneak peek before launching to the public.

If you’re a startup and are interested in checking out the new and improved General Counsel, click here to schedule a 15-minute call with me.

If you’re a Venture Capital and interested in understanding if it may be a good fit for your portfolio companies, click here to schedule a 15-minute call with me.   

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Prime Numbers

$795.8 billion—Tesla’s market cap is $795.8 billion. The next closest competitor in the automotive industry is Toyota at $207.5 billion.

$11 million—A rocket-powered car that was designed (and failed) to break the land speed record—763 miles per hour—is up for sale for $11 million.

100—The Pennsylvania Department of Transportation studied nine years of data around 22 new roundabouts that replaced more conventional intersections, and found that installing traffic circles reduced fatalities by 100 percent, serious injuries by 77 percent and minor injuries by 57 percent.


I love Calendly—the cloud based scheduling product. I’m a Calendly fanboy. (This is not a sponsored link. But hey, if you work at Calendly, reach out and we can make something happen.) Other than maybe email and the iPhone, it’s the single product that has created the most value in my life. By allowing me to own my time, I’ve become much more productive at work and much more present outside of work. What a game changer. I don’t just love the product, but I also love the company itself. Instead of going the typical Silicon Valley venture-backed route, it has charted its own course. Here are three reasons I love the company: 1) Calendly is profitable. Crazy idea, I know! Last year, the company made about $70 million annually in subscription revenues from its SaaS-based business model. Calendly is already profitable, and it has been for years. More recently, it has seen a boost, specifically in the last 12 months, as new Calendly users have emerged as a result of the pandemic. Currently, some 10 million of us are using Calendly for all of this on a monthly basis, with that number growing 1,180 percent last year. Business users from companies like Twilio, Zoom and the United States Chess Federation (USCF) are now joined by teachers, contractors, entrepreneurs and freelancers, the company says. 2) Calendly is based in Atlanta, an increasingly notable city for technology startups and other companies, but more often than not short on being credited for its heft in that department (SalesLoft, Amex-acquired Kabbage, OneTrust, Bakkt and Mailchimp not too far away). 3) Calendly has delayed VC money until after profitability. This week, they announced an investment of $350 million from OpenView Venture Partners and Iconiq. The funding round values the startup at more than $3 billion. Not bad for a company that before now had raised just $550,000, including the life savings of the founder and CEO, Tope Awotona, to initially get it off the ground. TechCrunch (12 minutes)

Startup Pricing

Pricing is often an afterthought for startups. Here are some frameworks, tactics and hidden truths Founders need to know about pricing—and how, when done correctly, it can dramatically accelerate growth. 1) If you don’t put pricing as part of your product-market fit validation, you’re just hearing what you want to hear. So it’s really about achieving product-market-pricing fit. 2) If your customer is not willing to pay, ask the most important question, “Why?” You’ll often hear so many insights on how you can design your products in such a way that you’ll maximize your chances of commercial success. 3) After you pitch a product, talk about the value. Ask someone, “What do you think is an acceptable price for this innovation?” Of course, people love to lowball. They love to negotiate with themselves. They will give you an answer. Clock it, then ask them, “What do you think is an expensive price for this innovation?” And then follow that up with, “What do you think is a prohibitively expensive price for this?” NFX (42 minutes)


I’m psyched that our client Co:census has been accepted to Techstars. Co:census focuses on getting deep community insights through public engagement and makes gathering and analyzing qualitative data easy and inclusive with multilingual text surveys and artificial intelligence (AI)-driven reports. The 2021 Techstars Social Impact Accelerator is working with and investing exclusively in companies tackling social injustice and systemic racism. Co:census, led by Tiasia Obrien, was selected from hundreds of applications across the country. The company takes innovative approaches to create scalable impact across the social injustice and inequality landscape. It’s great for Tiasia, and under-represented founder, and her team to finally get the recognition they deserve. I know they’ll come out of Techstars with an improved product and momentum for their next round of funding. Techstars (4 minutes)

Computational Propaganda

Since 2016, the team at the Oxford Internet Institute has monitored the rapid global proliferation of social media manipulation campaigns, which we define as the use of digital tools to influence online public behavior. In the past four years, social media manipulation has evolved from a niche concern to a global threat to democracy and human rights. Their latest report found that organized social media manipulation campaigns are now common across the world—identified in 81 countries in 2020, up from 70 countries in 2019. They focus on the use of “cyber troops”—teams from the government, the military or political parties that are committed to manipulating public opinion on social media. Cyber troops regularly conduct what we call “computational propaganda” campaigns. Computational propaganda involves the use of programmed bots or humans to spread purposefully misleading information across the internet, often on an industrial scale. To do this, computational propagandists make use of an extensive toolkit of disinformation tools. Political bots amplify hate speech and create the impression of trending political messages on Twitter and Facebook. The illegal harvesting of data helps propagandists target messaging at specific, often vulnerable individuals and groups. Troll armies, meanwhile, are regularly deployed to suppresses political activism and the freedom of the press. In addition to the cyber troops, research found state actors working with private computational propaganda companies in 48 countries in 2020, up from 21 identified between 2017 and 2018, and only nine such instances between 2016 and 2017. Since 2007, almost $60 million has been spent globally on contracts with these firms. The Conversation (14 minutes)

Peak Bay Area

Where are tech companies going to go once the pandemic subsides as vaccines reach more and more Americans? There’s a bunch of talk about Silicon Valley decamping to Austin and Miami. But there’s a more obvious answer. Pre-pandemic, the Bay Area was still the leading choice for our founders in terms of where to start a company. There were many other cities that were distant seconds or thirds, including New York and Seattle. Post-pandemic is a different story. More than 40 percent of founders say that the best place to start a company will be in the cloud. Expect to see decentralized or remote companies displace companies based in the Bay Area over time. As somebody who spends a lot of time incorporating early-stage companies, I’d say this aligns with my experience. Initialized Capital (7 minutes)

Missing Weak Ties

Understandably, much of the energy directed toward the problems of pandemic social life has been spent on keeping people tied to their families and closest friends. These other relationships have withered largely unremarked on after the places that hosted them closed. The pandemic has evaporated entire categories of friendship—weak ties—and by doing so, depleted the joys that make up a human life—and buoy human health. Weak ties are the people you see infrequently and near strangers with whom you share some familiarity. They’re the people on the periphery of your life—the guy who’s always at the gym at the same time as you, the barista who starts making your usual order while you’re still at the back of the line, the co-worker from another department with whom you make small talk on the elevator. They’re also people you might have never directly met, but you share something important in common—you go to the same concerts, or live in the same neighborhood and frequent the same local businesses. You might not consider all of your weak ties friends, at least in the common use of the word, but they’re often people with whom you’re friendly. The Atlantic (12 minutes)

The Cost of Light

Before modern lighting, we used to go to sleep when night arrived, waking briefly for an hour or two deep into the night before retiring again until the morning. Today, darkness poses no constraint: One can finish work in the evening and cook dinner, but still have hours more to read, study or watch television. But light was not always so easy to procure. It is, in fact, astounding how little effort an hour’s worth of light costs us. This fascinating interactive piece of journalism allows you to explore how much effort has been historically required acquire light. Pudding (21 minutes)


Exactly What to Say by Phil M. Jones. Often the decision between a customer choosing you over someone like you is your ability to know exactly what to say, when to say it and how to make it count. Phil M. Jones has trained more than 2 million people across five continents and over 50 countries in the lost art of spoken communication. In Exactly What to Say, he delivers the tactics you need to get more of what you want. Amazon

Most Read Last Week

Outdoors—This satirical article from a fictional architect is both hilarious and searing—pointing out the bizarre world we love in right now.

Two Worlds—A hard thing to wrap your head around in economics is the idea that two opposite things can be true at once.

Books in 2020—This is every book I read in 2020 rated and ranked.

About the Weekend Briefing

A Saturday morning briefing on innovation & society by Kyle Westaway—Managing Partner of Westaway and author of Profit & Purpose. Photo by Angel Santos.

Should We Work Together?

This newsletter is my passion project. I hope it helps you gain deeper insight and equips you to create meaningful impact in the world. Many readers have asked about how we can work together. In case you’re interested, I run a law firm for startups. We try to keep things simple by offering transparent flat fees. We structure our engagements in two ways: (1) Per-project flat fee engagements—No billable hour means no surprise legal bills. (2) General Counsel—A simple monthly fee for all your day-to-day legal needs. It’s like getting a subscription to your own general counsel. If you’re interested, let’s jump on a call to see if you’re a good fit for the firm. Click here to schedule a call.

Weekend Wisdom

We can easily forgive a child who is afraid of the dark; the real tragedy of life is when men are afraid of the light. Plato

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