Greetings from San Francisco.

And welcome back to The Stratosphere. Today, we have two stories on the intersection of Silicon Valley and Washington. Mentioned in today’s email: Pete Buttigieg; Eric Holder; “Wine Cave” owner Kathyrn Hall; possible Pelosi successors Christine Pelosi and Scott Wiener; Blake Masters; Chris Buskirk; and Paul Singer.

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The Speaker’s inevitable departure will create a Pelosi-sized hole in the Democratic Party’s fundraising machine. After all, an enormous obligation of the House leadership role is the ability to coax Democratic donors into parting with veritable mountains of cash. And Pelosi, a centimillionaire herself who grew up in a political family, is perhaps the most gifted high-dollar fundraiser and ego-stroker in politics today. Last April, she raked in $4.4 million in a single week—the largest ever individual donor event for the Democratic Congressional Campaign Committee. Her successors though would be wise to read beyond the headline figures and pre-baked narratives about her “powerhouse” operation to understand exactly how she does it. And the best glimpse of that is in Napa...