WeWork’s Adam Neumann signed up for a Q&A with NYT. Here’s what we want to ask him

Here’s a walk down memory lane through WeWork’s historic flameout, in advance of the upcoming one-on-one for the New York Times DealBook Summit.

WeWork’s Adam Neumann signed up for a Q&A with NYT. Here’s what we want to ask him
Adam Neumann. [Source Image: STUART ISETT for Fortune Brainstorm TECH/Flickr]

Sometimes one has to go away in order to come back. Unless, of course, one is a former CEO who had to step down from his own high-profile startup after a disastrous IPO attempt. In that case, one should perhaps at least spend a bit more than a couple years away before coming back. The unreflected life and all that.


Such is the case with WeWork cofounder Adam Neumann, who is embarking on what looks suspiciously like a comeback tour less than three years after his company’s dramatic nosedive from a $47 billion valuation in 2019. Though WeWork finally went public in October through a special purpose acquisition company, at a more earthbound $9 billion valuation, Neumann would have seemed to be persona non grata on Wall Street and in Silicon Valley. And yet! He will apparently be participating in the New York Times DealBook Summit, an event featuring “the most influential minds in business, policy and culture.” Neumann’s portion of the two-day event is scheduled to take place on the morning of Tuesday, November 9, and will feature a one-on-one conversation on the topic of “his tumultuous quest for workplace utopia, the lessons he’s learned, and his own next act.”

As the former CEO begins his redemption arc in earnest, Fast Company has some questions for Neumann that hopefully won’t slip through the cracks during the DealBook interview.

  1. Hi Adam, great to see you again! So let’s dive right in. In 2017, you got SoftBank CEO Masayoshi Son to invest $4.4 billion in WeWork after spending 12 minutes walking around together. How much capital do you think he might have invested had it been a full 20 minutes? Have you gone on any walks, short or long, with him lately and if so what were the terms?
  2. Which of these previous descriptions of yours do you now feel most accurately describes the concept of a coworking space: a “physical social network,” a “capitalist kibbutz,” a refuge for “orphaned children,” or a way to “elevate the world’s consciousness“?
  3. WeWork was able to go public this year in part because it rationalized its cost structure. Speaking of which, what is the least amount of money a company should be hemorrhaging before it becomes acceptable for the CEO to have purchased a $60 million private jet?
  4. In 2018, you used a “community adjusted EBITDA” (earnings before interest, taxes, depreciation, and amortization) as a fiscal metric, even though it “subtracted not only interest, taxes, depreciation, and amortization, but also basic expenses like marketing, general and administrative, and development and design costs” to conceal WeWork’s true financial position. Would you describe that today as an innovative form of financial reporting, or merely a radical form of CEO self-care?
  5. Also in 2018, you reportedly expressed interest in becoming Crown Prince Mohammed bin Salman’s spiritual adviser, in order to “work everything out” after Jamal Khashoggi’s murder. So how would you have done that? And what exactly is your criteria for selecting business partners, should you launch a company in the future?
  6. Related: While you were making an infomercial about peace in the Middle East for Jared Kushner, did you at any point consider, perhaps I shouldn’t be doing this?
  7. In the winter of 2018, WeWork led a $32 million investment in a snack company that specializes in turmeric coffee creamer, started by your surfer buddy Laird Hamilton, despite the money being designated for “technology investments.” Did you make that investment because turmeric coffee creamer is the secret sauce that fueled WeWork’s other technology investments?
  8. Do you think the gripping saga of WeWork’s historic mismanagement is best suited to a documentary film, a limited series starring Jared Leto, or a separate limited series starring Cousin Greg from Succession?
  9. While we’re on the subject, assuming you’re up to date on Succession, what do you make of Logan’s decision to appoint Gerri interim CEO? Wouldn’t it have been great to have a Gerri when you were going through it at WeWork?
  10. A follow-up: How many former employees have to describe a working atmosphere as “cult-like” before the CEO becomes the subject of a true crime podcast from Wondery?
  11. In Hulu’s WeWork documentary, you yell at your employees, “never give up! Work until you drop!” Given the Great Resignation, have you reconsidered your approach to managing people? Or are startups just, you know . . .
  12. Employees were reportedly made to wear tracking bracelets at your annual three-day corporate retreats called Summer Camp. Could you adapt the system to perform contract tracing in today’s environment? And is that really a fair requirement for a company whose CEO can’t be bothered to wear shoes or socks in the office?
  13. If a CEO describes their company as a family many times, does it make that company any less of a family if thousands of laid-off employees find their stock options have fizzled out while the CEO gets a golden parachute of at least a billion dollars?
  14. Is forcing employees to attend weekly, post-5 p.m. Thank God It’s Monday parties an insult to Garfield?
  15. After starting a school called WeGrow, an apartment complex called WeLive, a gym called Rise by We, and a software platform called Powered by We, how is it even possible that you didn’t invest in a dispensary called WeWeed?
  16. Before teaming up with Ashton Kutcher to pitch NBC on a Shark Tank-style series based on WeWork’s Creator Awards, a thing that really happened, did you consider pitching the series on a special episode of Shark Tank?
  17. In 2019, word got out that you made $6 million by selling the “We” trademark back to the company. Have you ever considered licensing the name of legendary Krautrock band Neu! for a line of dolls modeled after yourself?
  18. Which of these previously stated ambitions of yours seems most likely as of 2021: being elected president of the world, living forever, or becoming humanity’s first trillionaire? Are you so pissed that Elon Musk seems to have the inside track on at least that third item?
  19. In your opinion, which is the best flavor of Juicero?
  20. Do you feel as though the point of the Icarus myth is that flying directly into the sun is awesome?