Weekend Briefing No. 352

Welcome to the weekend.

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Prime Numbers

515,000—Bozeman, Montana had a population of 50,000 in 2019, and this year alone has seen the median home price increase from $432,500 to $515,000. Realtors in the area report that as much as 95 percent of their new clientele is from the Bay Area.

51—Just 51 percent of Facebook employees believe the company has a positive impact on the world. That’s down 23 percentage points from May.

33.7—Prices for plane tickets cratered in March—down 31.6 percent compared to March 2019—and have not rebounded since, with October seeing ticket prices down 33.7 percent compared to the same month of 2019.

Raising Capital During in a Pandemic

If you are an entrepreneur preparing to raise capital, what’s different during the Covid-19 pandemic? What are the keys to successfully navigating the current funding context? In order to answer those questions, I’ve interviewed entrepreneurs that have raised a cumulative $300 million this year. Their financing stages range from Seed to Series E. In addition, you’ll hear from investors who have continued to invest during the pandemic. My most recent Forbes article is a summary of their most salient advice including: (1) How to assess if it’s the right time for you to raise; (2) How to excel at your pitch over Zoom; (3) How to ensure your investor is the right match; (4) The importance of extending your runway; (5) How to communicate your COVID-19 pivot; (6) The importance of communication; and (7) Why this is an opportunity for startups. This is a longer form piece (2,422 total words) and packed with good advice. I put a lot of work into this one. I hope it will be helpful. Please share this with anybody that’s raising now. Forbes (18 minutes)

Transition Economy

Many Americans already know life and—most importantly—work is in the transitions. Workers 25 to 34, on average, leave a job after 2.8 years, 36 percent of the economy moves from gig to gig, and 40 million Americans are now unemployed due to COVID-19. The problem is our educational institutions, governmental support systems and corporate structures have not caught up to this reality. They continue to build and operate an antiquated infrastructure designed for a stable, linear, 1950s American workforce. This disconnect is keeping millions of Americans from building fulfilling and economically viable careers. It is time to reengineer some of our most deeply held professional pathways. The Hill (6 minutes)


On the heels of a historic week for our country, when does the healing begin? Join me and the team from Unfinished for “Episode 2: Democracy & Voice.” Premiering on Tuesday, November 10, at 7 p.m. ET/4 p.m. PT, this second installment of Unfinished Live will bring together Reverend William Barber, Valarie Kaur, Yo-Yo Ma, Eric Liu, Krista Tippett, Hank Willis Thomas, Kristen Soltis Anderson, Arthur Brooks and others to imagine the future of democracy. RSVP at Unfinished. (Sponsored)

Management Rules

Lambda School’s Molly Graham has six counterintuitive management rules. Here’s a quick preview of what she had to share: Rule #1: Management is not leadership. Rule #2: Don’t try to create robots. Focus on managing the what, not the how. Rule #3: Never create a second patient. Rule #4: Spend more time than you think you need to with your high performers. Rule #5: Set expectations, but know that you’re not always the one who needs to bring the clarity. Rule #6: Remember direct is kind, and have the hard conversations. First Round Review (22 minutes)

How to Lose the Underdog Spirit

(1) Stop hiring the awkward ones. (2) Chase the numbers, not the change. (3) Stop innovating. (4) Only back surefire things. (5) Stop trusting the team. (6) Make slow decisions. (7) Forget why you started. (8) Oust the founder. (9) Let success steal your hunger. (10) Stop socializing together. Do Lectures (1 minute)

Leave No Trace

In April 2017, a man started hiking in a state park just north of New York City. Six months later and 600 miles south, on July 23, 2018, two hikers stopped to rest their feet at a place called Nobles Camp. There they saw a yellow tent and a pair of boots outside. Something smelled bad, and something seemed off. They called out, then peered through the tent’s windscreen. An emaciated, lifeless body was looking up at them. They called 911. “Uh, we just found a dead body.” The man went by “Mostly Harmless.” He was friendly and said he worked in tech. After he died without ID or phone and didn’t come up in any DNA database, no one could figure out who he was. The dude seemed to have followed, to near perfection, the hiker credo of “Leave no trace.” The story pulled people in. An avid Facebook group committed to figuring out his identity soon formed. Reddit threads popped up to analyze the notes he had taken for Screeps. Amateur detectives tracked down leads and tried to match photographs in missing persons databases. A massive timeline was constructed on Websleuths.com. But thus far, this is the case that the internet can’t crack. WIRED (20 minutes)


New York Times put together a set of fun distractions for stress relief during election week. Check it out. New York Times (15 minutes)


The Amazing Adventures of Kavalier & Clay by Michael Chabon. Winner of the Pulitzer Prize, this is an epic, beloved novel of two boy geniuses dreaming up superheroes in New York’s Golden Age of comics. A young escape artist and budding magician named Joe Kavalier arrives on the doorstep of his cousin, Sammy Clay. While the long shadow of Hitler falls across Europe, America is happily in thrall to the Golden Age of comic books. In a distant corner of Brooklyn, Sammy is looking for a way to cash in on the craze. He finds the ideal partner in the aloof, artistically gifted Joe, and together they embark on an adventure that takes them deep into the heart of Manhattan and the heart of old-fashioned American ambition. From the shared fears, dreams and desires of two teenage boys, they spin comic book tales of the heroic, fascist-fighting Escapist and the beautiful, mysterious Luna Moth, otherworldly mistress of the night. Climbing from the streets of Brooklyn to the top of the Empire State Building, Joe and Sammy carve out lives, and careers, as vivid as cyan and magenta ink. Spanning continents and eras, this superb book by one of America’s finest writers remains one of the defining novels of our modern American age. Amazon

Most Read Last Week

Branding fails—The biggest branding fails since 1995.

Bento—There is a theory called Bentoism, an acronym for BEyond Near Term Orientation.

November Playlist—This is my music for November.

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 Bernard Hermant.

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

Everybody needs beauty as well as bread, places to play in and pray in, where nature may heal and give strength to body and soul.John Muir

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