Haley Joel Osment and a cold snap are the latest disruption to Silicon Valley’s ecosystem

At this point, the failure of the Pied Piper team to achieve long-term success is as much ingrained into Silicon Valley as Charlie Brown’s inability to ever kick the football Lucy Van Pelt holds up for him. Showrunner Alec Berg admitted as much in those exact terms a Vanity Fair interview, pointing out that in the real world Pied Piper would be able to sell its tech in a heartbeat, the team would become millionaires, and then the show would have no further reason to exist. Consequently, the prospect of real success has to be regularly placed within reach for Richard and his team, and then taken away at the last minute.

This process can be a frustrating one for both characters and viewers, but one of the reasons Silicon Valley is largely able to get away with it is that they have an entertaining variety of Lucys to yank the football away. Be it the endless resources of corporate giants, mercurial investors and executives, and the team’s own short-sightedness and egotism, it’s rare that Richard and company wind up failing the same way twice. “The Keenan Vortex” proves the well isn’t dry, introducing not one but two new complications to Pied Piper success and putting them in a position where they’ll need to rise from ashes both metaphorical and literal.

The first of those complications is a cold snap sweeping through California. Making the weather itself turn on the cast is an excellent comedic move, underlining how sheltered this part of the world can be and how something as trivial as cold weather can throw the entire thing into chaos. On the micro level it’s forcing the team to wear more layers of clothing in the house—Erlich refusing to turn on the heat—and on the macro it’s throwing the state’s residents into such a panic that insurance claims at FGI are up. This traps Pied Piper in a vicious dilemma, pushing their storage capacity and resultant server bills past their ability to pay.

Enter Keenan Feldspar, who’s become the industry’s latest golden boy after developing a supposedly revolutionary VR platform. Introduced back in “Customer Service” as Erlich’s golden ticket to join Bream-Hall, Keenan offers a similar lifeline to Richard as a second data storage client. Haley Joel Osment brings a new kind of energy to Silicon Valley, seemingly free of the bravado and ruthlessness that’s characterized other angel investors. (“I was getting bummed so I turned my phone off and went kite-surfing in Fiji” is how he explains his delay in signing a deal.) He’s happy to be here, happy to hang out with some new friends, and happy to show off his tech without any sort of encumbrance. It’s a nice break from the normal intensity, and Osment does a great job keeping his chillness chill.

It’s an attitude that pays dividends when introduced to the Pied Piper team. Dinesh and Gilfoyle are so excited to finally associate with a winner that they wind up staying at Keenan’s house for three days—both wearing his “rad” pajamas by the end of it, in a sequence that’s one of the best understated visual gags in the run of the series. They’re so comfortable in fact that they start talking shop with Keenan, working to mesh the algorithm with the VR tech and make the demo even smoother. Albeit in the creepiest fashion, given leering at women who can’t react is currently the main selling point:

Dinesh: “I walked right up to the barmaid, and I just looked at her! For a really long time. This technology could change the world.”

Gilfoyle: “The possibilities of your consequence-free world are darkly promising.”

The partnership is so exciting to Keenan he offers to acquire their company, and with that deal comes one of the main reasons for Pied Piper’s failure: more often than not, they do it to themselves. At various turns Richard has proven himself too idealistic, too short-sighted, or too petty to make the deals that would guarantee him long-term success. The latter is on full display next to Keenan’s easygoing attitude and obvious success, the perfect combination to set off “envious little crone” tendencies in someone who’s never had any luck with either. Spiteful Richard has become an increasingly prevalent flavor of Richard, and that spite is a natural reaction as he interacts with a technical wunderkind on his level for the first time in the series.

No wonder he’d buck against making the deal or try to sabotage it by upping the ante to an unreasonable level, only it looks like he’s swimming against the current. As he did in “The Uptick,” Erlich makes a Hail Mary deal that will put Pied Piper back on the road to success, once again playing VCs off each other to get the full payout and make himself the company’s COO in the process. Pair that with Keenan providing Richard with praise and partnership, and a deal is finally able to materialize. Here comes a tantalizing glimpse of success as the boys go full Entourage in the palapa, popping champagne over each other and briefly living in a world not designed to grind their dreams into a pulp.

What’s the latest method of dream-grinding? Well, it turns out that Pied Piper isn’t the only company that’s being adversely affected by the weather, as a frozen parking lot led to a catastrophic disaster at a Hooli facility and the next iteration of the box is delayed. It’s been a while since we’ve spent time with Jack Barker and Hooli, and once again Stephen Tobolowsky is perfectly situated to deliver the highest levels of executive bullshit, between his pun-filled presentation and his awestruck reaction at Gavin’s previous monotone deliveries. (Hoover’s own beaming reaction to those YouTube videos indicates the flames of loyalty haven’t been extinguished just yet.) Jack needs a win, Keenan needs a payday, and both of them come together in the announcement of Hooli’s entry into the VR field at Hooli-Con.

The move makes the latest deal—and Richard’s decision to back out of the deal behind his team’s back—all for nothing. A new ticking clock is established with five days to pay server costs before the data is pulled, ending their deal with FGI and essentially killing their new Internet in its hypothetical crib. Erlich’s palapa goes from the Hacker Hostel’s VIP corner booth where deals are made to a burnt husk, its owner left silently sitting amidst the ruins. On Silicon Valley things have to get bad before they get worse, and “The Keenan Vortex” proves that while things may suck for the team, at least they have the decency to suck in interesting ways.

Stray observations:

• Big thanks to Vikram Murthi for covering for me last week! Always good to get his take on things.
• This week’s closing track: “Freeze Me,” Death From Above 1979.
• Our own Esther Zuckerman spoke to Osment about playing Keenan, and it’s worth a read for his observations on the character’s seeming obliviousness and tonsorial choices.
• Best comedic beat this week: Zach Woods going over nautical metaphors, or Stephen Tobolowsky running through box puns?
• It was almost startling to see Erlich swearing in excitement after hearing about his key-man clause, given how many times he’s sworn in rage with the Jian-Yang albatross around his neck.
• Jack’s redecorated Gavin’s office with his own flourishes, including a large wood engraving of the Conjoined Triangles of Success, various horse sculptures, and the stand-up bass liquor cabinet I still covet.
• Jared’s reveal in the beige sweater made me go back and see if it was a match to Monica’s bearer-of-bad-news outfit. It wasn’t, but for a moment I got excited about the possibility that Jared and Monica have been sleeping together all season and the show has simply never bothered to mention this.
• Colin Powell will also be attending Hooli-Con, and gerts
• Dinesh, on selling a second client their hypothetical services: “That’s like getting a new credit card to pay off the old one.” Jared: “And as CFO, I should tell you we’ve already done that seven times.”
• “Wow, you really threw up a lot! And like immediately.”
• “Everything he touches turns to gold, and you are… different… than that.”
• “I had a feeling of mad! Then I had lunch, and after that I was a little tired, but mostly I felt pretty okay.”
• Richard: “We’re pirates, and our ship is sinking, and Keenan is Hawaii.” Monica: “This is what you guys talk about all day?”
• “If you need to kick another hole in the door, we understand.”