Dr. Paul Borosky, DBA, MBA
Business Consultant & Author
Why Did WeWork Fail? Motivation With No Finish Line
WeWork started with a sound idea and reached a $47 billion valuation. It filed for bankruptcy in 2023. Dr. Paul Borosky reads the story at the level of the decision, because the decision is the part you can learn from.
Last Updated: 10/28/2026 · Written by Dr. Paul Borosky, DBA, MBA
The Short Answer
Why Did WeWork Fail?
WeWork made growth the goal instead of a way to reach a goal. It chased size with no defined destination, leased long and rented short, and leaned on a flattering number to hide the losses. Bigger was the plan. Bigger is only a direction.
This is the cautionary tale in Chapter 1 of Become Your Version of Rich by Dr. Paul Borosky, DBA, MBA. It shows what motivation looks like when it has no finish line. You can fix that on paper in twenty minutes with the driver statement method. If you run a team, the planning side lives in what planning means in management. The whole cluster sits inside the Become Your Version of Rich guide.
What Happened
From a Sound Idea to Chapter 11
The business was real. The numbers got out of hand.
- 2010WeWork launches. It leases office buildings on long contracts, renovates them, and rents the space back in small, flexible pieces to freelancers and small companies.
- 2017Revenue of about $886 million, and a net loss of roughly $900 million, according to its bond offering documents.
- January 2019SoftBank invests another $2 billion at a $47 billion valuation.
- August 2019The IPO filing shows losses above $900 million in six months. Public investors do not buy the story.
- Fall 2019The IPO is shelved, Adam Neumann leaves, and a SoftBank rescue values the company at about $8 billion.
- November 2023WeWork files for Chapter 11 with about $15 billion in assets and more than $18 billion in debt.
Sources: Associated Press, WeWork files for bankruptcy in stunning downfall from its $47 billion heyday (Nov. 2023). CNBC, WeWork offers a romantic vision in its IPO filing, alongside staggering losses (Aug. 2019). Axios, Digging into WeWork’s new financial metric. Rescue valuation per Reuters via TechXplore.
Figures vary slightly by source and by what is counted. The direction does not.
The Decision Underneath
Growth Became the Destination
WeWork’s core idea was fair. Plenty of freelancers and small companies did not want a long lease of their own. Co-founder and CEO Adam Neumann was a magnetic leader who could raise money like almost no one alive. Dr. Paul gives both their due. Then the company made one fateful decision, and it is the same one Napoleon made, in a modern suit.
It bet on growth for its own sake. Get enormous, fast, and treat the size as the goal. Outside money paid for the sprint. The model made it riskier, because the company leased long and rented short. Its costs were locked in for years while its revenue could leave on short notice. Size did not fix that. It raised the stakes.
Notice what is missing. Nobody ever wrote down the sentence that finishes the thought: we will know we are done when. With no finish line, every quarter has the same answer, which is more. That is motion, not a plan. Dr. Paul calls it a missing stop line, and he returns to it throughout the book.
The Tell
When You Invent a Better Way to Measure Profit
This is the part managers can use tomorrow.
As losses mounted, WeWork leaned on a measure it invented, called Community Adjusted EBITDA. In plain terms, it counted what it earned from a building against that building’s own running costs, and left out company-wide expenses such as marketing, general and administrative costs, and development. The result looked far healthier than the net loss beneath it.
There is nothing wrong with a company tracking unit economics. The trouble comes when the friendly number replaces the standard one. When someone has to create a new way to measure profit so the losses look smaller, there was never a real finish line. There was only motion. Once the public could read the standard numbers, the story came apart in weeks.
Your Smaller Version
You Will Not Raise Billions. You Can Still Make This Mistake.
The fix is a sentence, not a spreadsheet.
Dr. Paul puts it this way in Become Your Version of Rich.
From Chapter 1 of Become Your Version of Rich
The error was never defining what enough looked like. Your version is chasing more of anything, more income, more clients, more followers, without ever writing down the actual target all that "more" is supposed to serve. Growth with no defined destination tends, sooner or later, to come apart. So write the sentence. It is the cheapest insurance you will ever buy.
That sentence works at any size. A five person company chasing more clients with no target, a sales team chasing more calls, a manager chasing a bigger headcount: each can drift the same way. Write the sentence first. Then use the enough line to decide what “more” is supposed to buy.
How This Helps a Manager
Use WeWork as a Checklist for Your Own Team
You do not control the company strategy. You do control your targets, your reports, and the questions you ask. Three places to use the lesson.
In Your Reporting
Show the standard number first
If you present an adjusted or custom metric, put the standard one next to it and explain the gap. A team that trusts your numbers will tell you bad news sooner. The method in root cause analysis only works on honest data.
In Your Targets
Give every target a finish line
A goal of “grow sales” has no end. A goal with a number, a date, and a reason does. Build them with SMART goals and tie each to the reason your company exists.
When Leadership Wants Growth
Ask what the growth is for
Ask the question politely and early: what does more buy us, and how will we know it is enough? A good answer sharpens the plan. A missing answer is your warning. Then read how to execute a plan to turn the answer into steps.
One Honest Caution
Growth Is Not the Villain
Growth is a fine goal when it serves a defined destination. WeWork is not a lesson that big is bad, or that its founders were fools. It is a lesson about one decision: treating size as the finish line. Many factors hit the company, including leases, markets, and a pandemic. This page isolates the motivation lesson, not the whole story.
Do This Tomorrow
Three Steps for This Week
- Write one sentence for your business or team: we will know this is enough when. Add a number and a date.
- Pick one metric you report. Check that the standard version is visible next to any custom one.
- In your next planning meeting, ask what the growth target is for. Write the answer down.
If the sentence is hard to write, you have found the real work. Start with how to find your why, then read why BlackBerry failed to see another company defend the past instead of reaching for a destination.
The Book
The WeWork Story Closes Chapter 1
This page covers one cautionary tale. Become Your Version of Rich places it next to people who aimed their drive well and one who did not.
- The five-step method to build your driver, with a 30-day check
- Madam C.J. Walker and Benjamin Franklin, two people who built motivation on purpose
- Napoleon, and what happens when a driver has no finish line
- The full WeWork cautionary tale and the sentence to write in response
- Daily Actions you can start tomorrow
Go Further With Dr. Paul
Check Whether Your Growth Has a Destination
Dr. Paul’s business growth plan consulting starts with the question WeWork never answered: what is the growth for? You leave with a written target, the numbers behind it, and a plan your team can run. Built on 1,000+ client engagements.
FAQ
Common Questions About WeWork’s Failure
Why did WeWork fail?
Was WeWork’s business idea a bad one?
What can a small business learn from WeWork?
Dr. Paul Borosky, DBA, MBA
Business Consultant, Author & Educator | 14+ Years | 1,000+ Clients Served
Dr. Paul Borosky, DBA, MBA is a business consultant, author, and educator, and the founder of Quality Business Plan. He helps small business owners across the United States and Canada with business planning, financial modeling, fractional CFO services, and the everyday problems of businesses that depend too much on their owners. He is the creator of Dr. Paul's Organize-Plan-Grow™ Strategy, author of numerous published books on Amazon, and publisher of over 1,000 business-focused videos on YouTube. He has taught as an adjunct college instructor and teaches in Florida public schools.
This page is for general educational purposes only. It is not investment, tax, legal, financial, or retirement advice, and it does not guarantee any particular financial result. The examples, figures, and calculations are illustrative planning tools, not recommendations. Before making significant financial decisions, consult a qualified professional.