WeWork

Dandy

WeWork

WeWork's model was fundamentally a real estate arbitrage play dressed up as a tech company. They signed long-term leases on buildings (often 10-15 years), spent millions renovating them, then rented desks and offices to members on month-to-month or annual contracts.

The spread between what they paid landlords and what members paid was supposed to be the profit.

The problem was the mismatch. Long-term obligations on the lease side, short-term flexibility on the revenue side.

In good times, buildings are full and the spread is healthy. In bad times — say, a global pandemic that empties offices — you're locked into paying rent on empty buildings while members cancel month-to-month.

Neumann tried to juice margins with ancillary services: WeWork Labs for startups, Powered by We for enterprise buildouts, and WeWork's own internal ventures. The company also launched WeLive (apartment living) and WeGrow (a private elementary school run by Neumann's wife).

These distractions drained cash without generating meaningful revenue.

Dandy

Vertical SaaS plus manufacturing. Dandy provides dental practices with intraoral scanners (often subsidized or free to eliminate the switching cost), cloud-based software for managing cases, and its own network of digital dental labs that manufacture the final restorations.

Dentists pay per case — each crown, bridge, veneer, or implant restoration is priced individually. The margin comes from manufacturing efficiency: digital workflows are faster, more precise, and require less manual labor than traditional hand-sculpted methods.

As volume grows, Dandy's labs get more efficient and per-unit costs drop. It's the classic razor-and-blades model — give away the scanner, make money on every restoration.

WeWork

Adam Neumann was a 6'5" Israeli former naval officer with a talent for fundraising that bordered on hypnosis. Miguel McKelvey was an architect from Oregon with hippie parents who raised him in a commune.

Together in 2010, they launched WeWork from a single building in SoHo, New York — though they actually started with a predecessor called Green Desk in 2008, which was a sustainable coworking space in Brooklyn that they sold to their landlord.

The original concept was dead simple: lease entire floors of commercial buildings at bulk rates, renovate them with trendy design — exposed brick, beer on tap, inspirational quotes on the walls — then sublease individual desks and offices at a premium. The "community" angle was the differentiator.

WeWork wasn't just selling desks. It was selling belonging, networking, the feeling of being a startup founder even if you were a freelance graphic designer working alone.

The timing was perfect. After the 2008 recession, commercial real estate was cheap and available.

The gig economy was exploding. Millennials were entering the workforce with different expectations about work environments.

And startups that couldn't afford traditional office leases needed flexible space. WeWork grew from 1 location to 5 within two years, and the waitlists were long.

Dandy

Henry Stott was a repeat entrepreneur who had previously co-founded a tech company in the UK. When he looked at the dental industry, he saw a $15 billion lab market that was shockingly analog.

Here's how it worked: a dentist jams a tray of gooey putty into your mouth, waits for it to harden, mails the physical mold to a dental lab, where a technician hand-sculpts your crown out of ceramic. Turnaround: 2 to 3 weeks.

Error rate: high. Patient experience: miserable.

The technology to do this digitally had existed for years — 3D intraoral scanners, CAD/CAM software, CNC milling machines — but nobody had stitched it into a seamless end-to-end platform for the average dental practice. Stott started Dandy in 2020 to be that platform.

Provide the scanner, build the software, run the lab — and make it so easy that any dentist can switch from analog to digital without changing how they practice.

WeWork

WeWork grew through sheer aggression funded by seemingly unlimited capital. They would enter a city, sign leases on multiple buildings simultaneously, renovate at premium cost, and absorb losses until locations filled.

The playbook was Uber-style: spend aggressively, dominate the market, worry about profitability later.

The "community" brand was powerful marketing. WeWork events, networking mixers, and the overall vibe attracted a loyal member base that became free ambassadors.

Instagram photos of beautiful WeWork interiors drove organic demand.

Enterprise was the real growth engine. By 2019, over 40% of members were from companies with 500+ employees.

Microsoft, Amazon, and Salesforce all had teams in WeWork. Enterprise clients signed longer contracts and were more predictable than freelancers, but WeWork still spent far more acquiring and building out space than it earned from these relationships.

Dandy

Land-and-expand with dental practices. Dandy gives practices the scanner for free or at heavy discount, which eliminates the biggest barrier to switching from analog.

Once a practice starts submitting digital scans, they become recurring revenue — every patient who needs a crown is a Dandy order. Sales team targets mid-size practices (3 to 10 dentists) that are high-volume but haven't invested in digital yet.

Referral programs where existing dentists recommend Dandy to colleagues. Geographic density strategy — build lab capacity in a region, then saturate practices nearby to optimize logistics and turnaround times.

Content marketing educating dentists on why digital is better, faster, and more profitable than analog workflows.

WeWork

Where to begin? The S-1 filing in August 2019 was a masterclass in red flags.

It revealed that WeWork lost $1.9 billion in 2018 on $1.8 billion in revenue — spending more than a dollar for every dollar earned. Neumann had taken $700 million off the table through stock sales and loans before the IPO.

He owned the "We" trademark personally and charged the company $5.9 million to license it. He had family members on payroll.

He flew on a private jet funded by the company.

The planned $47 billion IPO was pulled in September 2019 after investors revolted. The valuation was slashed.

Neumann was forced out and given a $1.7 billion exit package — for nearly destroying the company. SoftBank took control, cut thousands of jobs, and spent years trying to restructure.

WeWork finally went public via SPAC in 2021 at a $9 billion valuation.

Then COVID hit the commercial real estate market like a meteor. Remote work became permanent for many companies.

WeWork's occupancy plummeted. They filed for Chapter 11 bankruptcy in November 2023, listing $18.7 billion in debt.

The cautionary tale was complete.

Dandy

Dental practices are notoriously resistant to change — many dentists have used the same lab for 20 years and switching feels risky. The scanner hardware is expensive to subsidize at scale, creating a capital-intensive land grab.

Quality control across distributed manufacturing is hard — a crown that doesn't fit means a remake, an unhappy patient, and a dentist who might switch back to their old lab. Competition from established digital players like Align Technology and legacy lab companies investing in their own digital capabilities.

The dental industry is fragmented — 200,000+ practices in the US, mostly small businesses, which means enterprise-style sales don't work. Each practice is its own decision maker with its own habits.

WeWork

WeWork All Access — a membership that gives access to any WeWork location worldwide, targeting remote workers and traveling professionals. Dedicated Desks — assigned workstations in shared open-plan spaces for individuals and freelancers.

Private Offices — enclosed offices for teams, the bread-and-butter product generating most revenue. WeWork Workplace — enterprise software for managing hybrid work, office scheduling, and space utilization analytics.

On Demand — pay-by-the-day access to meeting rooms and workspace without a monthly commitment.

Dandy

Dandy Scanner — provided to dental practices, captures a full 3D digital impression of the patient's mouth in minutes. No more putty molds.

Cloud-based case management platform where dentists submit scans, approve designs, and track orders. AI-powered restoration design that generates crown and veneer designs automatically from 3D scans, reducing turnaround from weeks to days.

Digital dental lab network with automated CNC milling and 3D printing for manufacturing restorations. Shade matching technology using AI to color-match restorations to surrounding teeth.

Integration with practice management software so cases flow seamlessly from scan to delivery.

WeWork

SoftBank Vision Fund was the largest and most consequential investor, pouring over $10 billion into WeWork across multiple rounds. Masayoshi Son reportedly agreed to invest after a 12-minute meeting with Neumann.

Benchmark was an early investor. JPMorgan Chase provided debt financing.

T. Rowe Price, Fidelity, and Goldman Sachs participated in later rounds.

The company raised more money than most companies ever generate in revenue.

Dandy

Investors include Bessemer Venture Partners, IVP, DST Global, and IA Ventures. Series C in 2023 valued the company at approximately $1.8 billion.