I’m always trying to think of new ways to level these pieces up. But I think the reality is that I spend a unhealthy amount of time reading tech news and many readers are happy to get a rundown of what I think matters. If you know me, then you know I feel guilty whenever I’m not breaking news or bringing exclusive access to a piece. But, truth be told, I’m always ambivalent about them. It’s a fun way to concisely hit a bunch of different topics at once. Given the slow IPO pipeline, there’s been a slowdown in cap table stories. The challenge with these pieces is that they require interesting companies to file to go public - and cooperative sources at a regulatorily-paranoid time in a company’s lifetime. An example from late last year: The Story of a Cap Table: GitLab. These are fun and instructive venture capital case studies. These pieces rely on my building up a depth of information about a particular sector before dropping it in a single post. Recent examples: Here’s What Investors Think the Treacherous Public Markets Mean for Private Startups or Good Times in The Great Revaluation. I’ve gotten my hands on another pitch deck so I should have another similar piece out in the coming days. (I added a few more slides after publishing the article by the way if you haven’t returned to it since.) Fans of that piece should also check out my article Inside 3 Crypto Funds' Investor Decks. Recently, I published a look at Tiger Global with some of the firm’s private fundraising decks. Stories about top investment firms based on their private fundraising materials. I’ve also been covering Y Combinator closely with my interview of YC President Geoff Ralston YC = Growth, What Insiders Think About YC's New Deal Terms, and Ali Partovi Wants to Beat the Old YC. And Andreessen Horowitz has been perhaps the main character of this newsletter with pieces like When Will a16z Become a Public Market Investor? I’d put my profile of Bessemer Venture Partners - The Anti-Portfolio - in this bucket. Probably my most iconic piece remains, The Unauthorized Story of Andreessen Horowitz. Sweeping, deeply-reported narratives about a venture capital firm. Think: Elad Gil Wants You To Live Longer or General Catalyst's Secret CEO or Above the Crowd. In-depth profiles of Silicon Valley main characters based on a probing interview. (On the podcast, we also talk about Elon Musk’s Twitter bid and Snap’s tumbling stock price.) But Substack is still figuring out just how many people can sustainably enter this line of work - solo creators, operating mostly without a safety net, selling media for a monthly fee. Having giant piles of cash on hand can be great for making splashy acquisitions or experimenting with new products. Two, having less cash on hand can enforce a useful kind of discipline on a company. The more Substack can rely on its own cash flow, the more easily it can chart its own future.

But giving up more equity to VCs will bring more “suggestions” from the company’s board to move in this direction. To its credit, Substack changed the default to preserve email subscriptions within 24 hours. In March, when the company introduced an app, I noted here that Substack shut off emails from your subscribed publications by default - a worrying step, I thought, toward building a centralized platform that the company could monetize more aggressively.

One, it reduces the pressure on Substack to financialize every facet of its newsletter, podcast and app ecosystem. Newton celebrated Substack’s failure to fundraise in his newsletter: Given the turbulent financial markets, Substack abandoned its fundraising effort, according to the report. Substack reportedly generated about $9 million in revenue in 2021. Unlike fellow Andreessen Horowitz portfolio company Clubhouse, which raised at a $4 billion valuation in April 2021, Substack hasn’t earned a unicorn valuation. Substack apparently isn’t raising a new round of financing, according to the New York Times. Our discussion was sparked by a news story about what’s not happening. (Paying Newcomer subscribers get access to the community, though I’ll confess that my channels are fairly dormant.) Newton and I are part of a group of writers that formed the Discord community Sidechannel together. Newton founded Platformer, a go-to destination for news and analysis about what’s happening in the technology industry - especially at social media companies. On the podcast, I reminisce about how I phoned Newton during the depths of the pandemic to tell him that I was going to leave Bloomberg to start a Substack only to learn he was about to launch one as well. This week on the Dead Cat podcast, Katie Benner, Tom Dotan, and I talk to technology Substack writer Casey Newton.

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