WeWork, once valued at $47 billion, emerged as a symbol of Silicon Valley ambition and excess, promising to revolutionize work through community-driven coworking spaces. Founded in 2010 by Adam Neumann and Miguel McKelvey, the company capitalized on post-2008 economic shifts, offering flexible office solutions amid a growing freelance economy. Its rapid global expansion, fueled by over $10 billion in investments from SoftBank’s Vision Fund, masked a fragile business model: WeWork was essentially a real estate subletter, signing long-term leases while offering short-term memberships, resulting in massive structural losses. The company’s culture, shaped by Neumann’s messianic vision and Rebekah Neumann’s spiritual branding, prioritized ’elevating the world’s consciousness’ over financial discipline. Red flags included Neumann’s self-dealing—leasing his own properties to WeWork, trademarking ’We’ for a $5.9 million sale, and using investor funds for a private jet—and a leadership style that dismissed employees over perceived ’bad energy.’ The 2019 IPO filing exposed these governance failures and unsustainable finances, triggering a collapse in valuation and Neumann’s ouster with a $445 million exit package. The onset of the COVID-19 pandemic devastated WeWork’s communal model, as remote work emptied its spaces, dropping occupancy from 72% to 47% by 2021. Burdened by over $2.7 billion in annual lease costs and declining revenue, WeWork filed for Chapter 11 bankruptcy in November 2023, listing liabilities between $10 billion and $50 billion. It emerged in June 2024 after eliminating $4 billion in debt, exiting or renegotiating 90% of leases, and securing $400 million in new capital. While the company survives in a leaner form, its legacy is dual-edged: it popularized flexible workspaces and influenced modern office design, yet it stands as a cautionary tale of unchecked founder power, financial opacity, and the perils of prioritizing hype over profitability. The collapse reverberated through commercial real estate, contributing to rising vacancy rates and falling rents. Meanwhile, Adam Neumann attempted a comeback by bidding to reclaim WeWork during bankruptcy and has since launched Flow, a new real estate venture, and Flowcarbon, a carbon credit tokenization platform. Rebekah Neumann is relaunching her educational initiative as ’Student of Life for Life’ (SOLFL). Ultimately, WeWork’s saga underscores the necessity of aligning visionary ambition with operational rigor, transparency, and sustainable economics—lessons now deeply embedded in the discourse around startup governance and investor due diligence.