Happy Tuesday and welcome back to the Stratosphere, my private email focused on the money, power, and politics emanating from Silicon Valley, and the players who run it all.

In today’s email, we have three stories that may catch your attention: 1) the latest on the game of chicken between Peter Thiel and Mitch McConnell that could endanger Republicans’ chances of taking the Senate this fall; 2) details on a fundraising reception with Barack Obama that could cost a pretty penny; and 3) the latest water-cooler conversation inside Laurene Powell Jobs’s Emerson Collective.

Meanwhile, we are celebrating our first anniversary here at Puck this week—the perfect time to subscribe, if you haven’t, or to share the sign up link with a friend. I’ll be back in your inbox with more information on that later this week.

Teddy

Masters, after all, is in a vise. Mitch McConnell’s political allies believe the current polling shows he “doesn’t have a shot” of defeating Kelly in November, a person familiar with their thinking told me, which is why the the Senate Leadership Fund, McConnell’s super PAC, recently redirected $8 million in planned September ad spending to more winnable races. McConnell’s mandate, after all, is to secure a 51-seat Senate majority for the G.O.P., not to support seemingly longshot Republican candidates.

Nevertheless, Masters was brimming with confidence this weekend, and came prepared with a diplomatic answer. Ronna Romney McDaniel has been great and Rick Scott has been helpful, Masters essentially responded, according to three sources who offered their recollections of the Miami event. Then Masters brought up McConnell. I’m going to do so well over the next few months that the establishment won’t have a choice but to fund me. I don’t necessarily need the money. I could use the money. And ultimately the money will be there.

The money, of course, already was there: Standing just a few feet away from Masters was Rabois’s co-host, and old Stanford Review buddy, Peter Thiel. Just a few moments before, Thiel had introduced Masters with his own well-worn spiel—about how Democrats are the “evil party,” and Republicans are the “stupid party,” but Blake is somehow neither. He took his own shots at Kelly, a retired Navy captain and former astronaut, a profession that Thiel deemed as “basically a fancy version of a monkey” as one source recalled. Helping Blake win Arizona, Thiel argued, would be critical to elevating a new generation of Republican leadership.

Unmentioned, naturally, was the fact that Thiel himself has yet to spend a dollar on Masters in the general election after seeding his primary campaign with some $15 million. Thiel believes that should be the job of McConnell, and feels he is essentially being extorted (the recent leaks won’t help). McConnell, in turn, seems to be withholding funds with the expectation that Thiel will eventually blink—after all, in his view, Thiel created this “problem” by helping buy Masters and J.D. Vance’s nominations in the first place. Why shouldn’t he pick up the rest of the bill?

Masters also had the opportunity to spend time with McConnell in Washington last week, where the Senate minority leader hosted a fundraiser for him. (A follow-up donor event is in the offing, I am told.) The two had never spoken in person before, but, as Masters told his audience at the Rabois fundraiser, their meeting in D.C. was productive and Masters is now optimistic about McConnell’s future involvement. McConnell, after all, is a thick-skinned pragmatist who wants to retake power, and the latest polls coming out of Arizona look more promising than before for the G.O.P. “[Masters] is currently being outspent six-to-one or seven-to-one, so it’s not like Peter is going to close that gap independently,” one close Thiel ally told me. “I think there’s a good chance McConnell is going to come in in October. He’s a savvy, rational guy and he’s going to see that the polls are better there than in, say, Pennsylvania.”

In the meantime, Masters is getting some financial cover to hold him steady: I reported in Tara Palmeri’s private email on Thursday that the Masters super PAC, Saving Arizona, recently received $1.5 million from an undisclosed donor who is not Peter Thiel, enabling them and operative Chris Buskirk to put a few more ads on the air. And on Monday, $6 million more in planned independent expenditures arrived, including $1 million from the American Principles Project and a $5 million pro-Masters offensive from a super PAC affiliated with the Heritage Foundation. “You had this public disparaging match between Thiel and McConnell, and when it became clear that they were both going to pause, at least for now, that’s when we saw our opening,” Jessica Anderson, the head of the Heritage super PAC, told me. “We’re Switzerland in all of this.” All told, these recent contributions make up for the S.L.F.’s $8 million aborted Masters ad campaign. On the hard-dollar side, Masters—along with almost the entire rest of the Senate G.O.P. slate—is raising money this week from two of Thiel’s closest friends, Rabois and David Sacks, again in Miami.

All well and good, but Masters is still being heavily outspent by Kelly, and he still needs more money from Thiel, from McConnell, or from both. In the meantime, time is ticking. Over the next few weeks, McConnell’s team will have to decide whether to cancel any of their October reservation. Ann Coulter, who is close with Thiel, offered me an entirely different solution. “Trump should pay for Masters’ ad spending. What on Earth is he doing with that $100 million+?” she wrote. “Unless he wants to be a TOTAL LOSER when all his candidates flame out, what’s he waiting for?”

The Lawsons are the hosts of Barack Obama for an intimate, high-dollar event benefiting a Democratic National Committee fund on September 29 in San Francisco, I’ve learned. Ticket prices are, predictably, through the roof: from a minimum of $36,500 for a “friend” ticket to a staggering $250,000 for a “host” ticket, a price that turned heads in the Democratic finance community. The only other names on the invite alongside the Lawsons are Ron Conway and Reid Hoffman—another indication of how the husband and wife team are becoming legit Silicon Valley royalty. Suffice it to say, invitations to play host to Obama aren’t handed out willy-nilly—they are a sign of respect and credibility in fundraising circles. The Lawsons are not in the innermost circle of the 44th president, but they did score a sit-down with him a few years back as they donated somewhere between $1 million and $5 million to the Obama Foundation. Now they get the Obama treatment. (Other interesting Democratic events on the agenda in the Bay Area over the next few weeks include two functions for Raphael Warnock featuring Joe Gebbia, Tom Steyer, Jon Ossoff, Conway, and the one and only Willie Brown; and another trip by Pete Buttigieg to Silicon Valley for the D.N.C.)

It will be interesting to see who else Obama sits down with when he comes out to the Bay. Obama has been spending tons of time in, or thinking about, Silicon Valley over the last few years, staying close with local aides like David Plouffe, Jim Messina and Jason Goldman, who is sort of Obama’s whisperer to the tech community. Obama typically builds in some private meetings—on a recent trip to the Bay, for instance, he slipped into Laurene Powell Jobs’s offices and home in Palo Alto.

“Narwhal is a new kind of social discussion platform, designed from the ground up to make conversations better. The plan is to create a digital space where people feel they can come to talk openly, honestly, and empathetically, and where the powers of the Internet are harnessed to create understanding not division,” reads the website for the holding page. “It will be a place where the design, the algorithms, and the business model are all aimed in one direction: sensible, structured, productive conversations. Like a Narwhal, it may sound like something magical – but it’s actually real.” The product, according to a job posting, is being built from “near scratch.” Laurene, more than many other tech moguls, has been thinking deeply about the perils of the Internet—even spending time with Obama on that issue.

But there is another move at the Emerson water cooler that fascinates me and other eagle-eyed observers of the Silicon Valley political scene: Emerson, for the last six to twelve months, has been working with Mike Yang, the political consigliere to Ron Conway, to advise on the company’s political work, I am told by people with knowledge of the arrangement. Referring to Yang as a “hire” is a little bit of a verbal stretch—Yang, the former general counsel at Pinterest, and before that, the second public policy hire at Google, has made his mint and works for Conway for free. But it is a formal arrangement with Ron, and I am told it is a formal arrangement with Emerson, which confirmed the new advisory role to me (but stressed that he isn’t advising Laurene personally). Yang is close with many donors and is as well-connected as they come, but he has told some people that he is working for Emerson about one day a week on political projects, which ain’t nothing.

Yang got into politics during the Trump era, and has “been trying to get out entirely, but keeps getting pulled back in” in the words of one friend, paraphrasing Michael Corleone’s famous phrase. And yet it should be little surprise that he would make time for Emerson: Laurene and Ron are close friends and have collaborated on many a domestic policy and democracy project. Then again, doing so for Conway is very different than doing so for Laurene and her team: Conway, with his fondness for ALL CAPS emails—not infrequently sent to the wrong person—is a workhorse with a blunt but high-minded and ferociously effective style of getting what he wants; Powell Jobs is of a very different temperament, with greater finesse and polish, broader interests that span art, sports, and entertainment, and much less love of the media spotlight. (She was still very impressive at Code last week as she unveiled a new archive featuring never-before-seen correspondence from Steve Jobs.)

Donor-advisors matter—they execute the plays behind the scenes that make politics happen. L.P.J. is advised by her longtime chief of staff, Stacey Rubin, who went from working in the Clinton administration to advising Jobs for two decades and so, yes, knows a thing or two about politics; but as empowered as she is, Rubin has to run the entire 150-person philanthropy day-to-day. Then there is Michael Schrum, a former top Joe Biden aide, Ben Wessel, the political strategist who once served as the top aide to Tom Steyer and now oversees Emerson’s democracy work, and Krikorian, the firm’s C.T.O. and former tech chief at the D.N.C., who chips in with his thoughts on the more technical projects, too.

Powell Jobs has historically shied away from straight-up partisan giving, tending to fund advocacy organizations, movement groups and media companies that might create more holistic, societal change. I wonder how Yang, who is very well-regarded and, as a technologist, often is called upon by the industry to credibly validate or invalidate ideas to the Silicon Valley donor set, will refine that strategy. Will Powell Jobs get more political, or less?