Newcomer Podcast
Coming to You From a Soon To Be Chesa-Free San Francisco (w/Jonathan Weber)

Coming to You From a Soon To Be Chesa-Free San Francisco (w/Jonathan Weber)

Notes from my reporting trip in San Francisco and a conversation with San Francisco Standard editor Jonathan Weber
Stephen Lam/San Francisco Chronicle via Getty Images

I moved from San Francisco to New York, in February 2019, back before it was cool to turn tail on the tech mecca. Truth be told, I’ll always have a special place in my heart for San Francisco, but my girlfriend beckoned from Brooklyn.

I’m writing this from my flight back to New York after over a week in SF. I spent much of it in an Airbnb next to Mr. Pickle’s on Van Ness Avenue and then a few days crashing at a fellow tech reporter’s apartment in the Outer Richmond. I ate Mission Chinese and La Taqueria, drank at Brass Tacks and The Monk’s Kettle, and made it up to Calistoga for a picturesque vineyard wedding.

But did I spend any time working for you, dear reader?

Yes, not to worry. I spent my days shuttling from South Park to the Presidio, catching up with venture capitalists, founders, tech media insiders, and senior tech executives. And I spent my nights getting drunk with them, eager for looser lips.

Here are my key immediate takeaways:

  • One source told me that even Insight Partners — which announced a $20 billion fund in February — has decided to seriously slow down big late stage private investments. Until recently, Insight looked like one of the last holdouts when it came to doing late stage deals even as the market unraveled. But now, like pretty much everyone else, it’s mostly focused on its existing portfolio.

  • VC advice on the downturn — even Sequoia Capital’s presentation to founders — has felt too much like content marketing. For some startup CEOs it can feel a bit like you’re the goody two-shoes, “A” student in the classroom, when the teacher reprimands everyone. You think the rebuke applies to you, but really the message is meant for the troublemakers. But it’s the most diligent among us that take these admonitions personally. Founders need advice specific to their company.

  • There’s a sense that there have been many software engineers who have been overpromoted in the bull cycle and that this downturn could force some coders to reset their expectations about their appropriate rank and pay.

  • I spent much of my time asking sources what the overarching, thematic story of the downturn would be. One venture capitalist gave me my favorite answer: He argued that we’d look back on this downturn as a story of the perfect storm between retail and professional investor excesses. On the retail side, we saw the rise of Robinhood and Coinbase, and r/wallstreetbets trades on Kodak and GameStop. On the professional side, we saw firms like SoftBank and Tiger go so, so long without enough diligence to back it up.

  • If I had to name a couple companies/firms that I think are most likely to represent this downturn, right now I’d name Instacart, Coinbase, Robinhood, GoPuff, Bird, Tesla, Tiger, and SoftBank. Though, right now, I think increasingly crypto is looking like it will be the category most associated with this cycle’s excesses.

  • There’s been a lot of envy in traditional startup world of people who went over to the the crypto dark side. Now there’s all sorts of schadenfreude going on as crypto prices plummet. Some VCs are starting to admit (mostly in private) that they never really believed in crypto. Still, there’s so much money. Just as I was leaving the city, Coinbase announced that it was brutally laying off 18% of its staff, locking them out of their emails before they even had time to say goodbye.

  • We’re overdue for a reckoning over who screwed over credulous investors with implausible SPAC deals. ~cough~ Chamath ~ cough ~ At least, Brad Gerstner’s Altimeter led the PIPE on its own terrible Grab SPAC deal.

  • Andreessen Horowitz still remains, probably, the biggest nemesis of many firms in Silicon Valley. Sure, Tiger blew up the startup world. But what Tiger did was so unlike anything venture capital firms were doing, so there’s less professional jealousy. There are whispers that things aren’t as copacetic internally at a16z as might appear from their highly choreographed public communications. It would seem that part of the explanation for the explosion of funds at the firm has been the explosion of egos. Instead of resolving interpersonal conflicts on the consumer fund, let’s just create a gaming fund. In that light, it’s pretty amazing that the firm couldn’t figure out a way to keep Katie Haun.

  • Consumer investing across the board seems challenged. What’s going on over at Popshop, Lunchclub, Cameo, and Clubhouse just to name a few? I guess investors simply wishing consumer investing into being without a strong new thesis wasn’t exactly an omen for the sector’s inevitable success. (I will say that Whatnot and BeReal remain two consumer plays that I’m still following.) What will it mean for this generation of consumer investors? Benchmark’s next generation consumer investor, Sarah Tavel, seems to have made her best investment in business-to-business company Chainalysis, last valued at $8.6 billion.

  • Speaking of Benchmark, the firm deserves some credit for holding firm on its strategy as other venture firms’ fund sizes got crazy. Sure, Benchmark probably could have made way more money if it topped up its own investments — but then it might be taking the heat that Benchmark favorite Altimeter is getting right now over its overexuberance. There’s money and reputation to manage. Benchmark has always made enough money to value its reputation. (That’s something Travis Kalanick, Adam Neumann, Nirav Tolia, etc. surely gripe about.)

  • Last year’s hype around venture capital firms indefinitely holding onto private companies long after they go public is looking like pure bubble thinking. Sequoia’s timing on its all-in-one, hold indefinitely “The Sequoia Capital Fund” looks a little more like one of the excesses from the bull market. But limited partners seem too afraid to do anything to unwind the strategy shift that seems designed to enrich the firm’s general partners. (Reach out to me if you have off-the-record intel on this.)

  • Investors are dramatically slowing the pace of their investments. These funds are going to last years longer than they would have in bull times. Multi-stage investors seem more inclined to double-down on their existing portfolio companies than to make new bets. Bridge rounds are on everyone’s lips. Still, I heard from investors who had made secret Series B and C investments in companies this year. It’s a good time to make a bet on a company that got away for a hype-y Series A round.

  • Startup founders think prospective employees want assurances that their company is really worth what the company says it is. Good private unicorns are in a bit of a bind. Prospective employees are now automatically giving their equity offers a mental haircut based on the market downturn. So good companies have an incentive to reaffirm their valuations with funding rounds during the downturn — even if it otherwise might be smarter to keep their valuations artificially low so as to maintain room to grow should conditions worsen. (I wish employees would get better at assessing companies based on fundamentals, rather than the last tick fundraising round. Employees are basically begging founders to maximize for valuation, which then minimizes employee upside.)

  • Some small-to-medium sized companies are shopping themselves to their rival startups but it’s not always clear why the competitor would want to buy. Why take on additional burn and headcount when all you might end up getting is leads on some new customers? Sure, you might do some venture capital firm a favor, but what’s that really worth?

  • There are some cracks in up-start media world. The most obvious tremor is at BuzzFeed where the stock has sunk 54% in a month. Reporters have been leaving in droves. Meanwhile, The Information lost one of its top editorsMartin Peers. He’s long been a central figure over there. The Information’s up-and-coming venture capital reporter Berber Jin departed to the Wall Street Journal, as did Sarah Krouse who will be covering Netflix for the Journal. Stephen Nellis returned to Reuters. Meanwhile spirits seem strong at my former employer, Bloomberg. The ascendance of the player-coach editor seems to have people upbeat. Sarah Frier is leading big tech coverage and Lucas Shaw (who has been a guest on Dead Cat) is running the show on Hollywood coverage. And somehow Bloomberg just lured back a former star reporter who had left to join the startup ranks: Alex Barinka — who left Bloomberg as a deals reporter to help launch Imran Khan’s Verishop before going over to Stitch Fix — is joining Frier’s team as a social media reporter based in LA.

  • Next week I’m in Toronto for Collision where I’ll be interviewing Uncork Capital’s Andy McLoughlin, Real Ventures’ Janet Bannister, and Left Lane Capital’s Vinny Pujji on a panel Wednesday called “Survival of the leanest: The importance of being capital efficient.” Then, less than an hour later I’ll interview General Catalyst’s Hemant Taneja about responsible innovation. On Thursday, I’ll ask “Has the tech bubble burst... again?!” in a panel with FirstMark’s Matt Turck, Lux’s Deena Shakir, and Neo Financial’s Andrew Chau. Expect the most interesting tidbits in this newsletter late next week.

Talking about Chesa Boudin on Dead Cat

My first meeting in San Francisco started with a tour of The San Francisco Standard, the Michael Moritz-funded local news enterprise. My old editor Jonathan Weber — once the editor of tech media dot-com icon The Industry Standard — is the editor-in-chief over at the SF Standard.

Weber, Dead Cat co-host Tom Dotan, and I met up for a nice dinner at The Morris in the Mission. After spending the evening discussing San Francisco District Attorney Chesa Boudin’s recall, Tom and I convinced Weber to come on the Dead Cat podcast and talk about the Standard and San Francisco politics.

Tom thinks I’m going to get eviscerated by San Franciscans for my politics. This is something we’ve never seen before: a New Yorker opining on San Francisco local affairs. I did my best to offend conservatives and liberals alike, maligning the police while rooting for tech’s ascendant influence on San Francisco politics.

Weber makes the case for objective, follow-the-reporting local news and outlines the real issues underpinning the recall. He explains how money is simultaneously to blame and not to blame for Boudin’s recall. And he defends the Standard against its critics for its influential story on Boudin’s refusal to make drug arrests. We interrogate what Boudin’s defeat means for the future of progressive politics and the city of San Francisco.

Give it a listen.

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Read the automated transcript.

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Newcomer Podcast
A podcast about Silicon Valley, hosted by newsletter writer and independent journalist Eric Newcomer. Listen in for interviews with the dealmakers and builders who matter. Subscribe to for summaries of the episodes plus tech industry news, scoops, and analysis.