• WeWork alumni are founding and investing in new companies after stints at the office giant. 
  • One VC who's backed them said these entrepreneurs dream big but stay focused, drawing on lessons learned the hard way at WeWork. 
  • The former head of WeWork South Korea just started a local real-estate company to make buying and renting homes easier, and he raised a pre-seed round largely from WeWork alumni.  
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Matt Shampine and Jesse Middleton's chance meeting at a Business Insider event in 2010 was just the first in a decade-long relationship that would see plenty of twists and turns. 

Shampine would go on to invest in a software startup Middleton had founded, and when they answered a Craigslist ad for office space from a small company called WeWork in 2011, they met another entrepreneurial duo, Adam Neumann and Miguel McKelvey. 

Shampine invited Neumann to invest in Middleton's company, with a handshake agreement that Shampine would help build the tech side of WeWork and Middleton would work at a WeWork office and help think about its venture business. They'd then wear many hats inside the fledgling office company, including co-founding WeWork Labs, a platform for new companies. 

Now, post-WeWork, the pair are once again thinking entrepreneurially, with Shampine as a founder and Middleton as a venture capitalist invested in Shampine's new real estate-focused startup.

Their paths show how WeWork is spawning a new generation of global startup founders, though the story isn't as straightforward as other tech companies that have bred generations of entrepreneurs.

Tech startups typically hire engineers and salespeople early on who may then go to become angel investors, but real estate-focused WeWork needed architects and construction professionals, among other roles, Middleton said. 

And after a company's initial public offering, early employees, finally flush with cash after years of locked-up stock, often found or invest in new companies. 

But WeWork's attempt at going public blew up last year and the company is staying private for the near future. Much of early employees' stock could be locked up for months, if not longer, after the company's largest investor, SoftBank, walked away from an agreement to buy up to $3 billion of stock that had been part of an October bailout.

Investors and founder Adam Neumann sued, and the case is still winding its way through court. That lockup put at least one former employee's plans to found a company on hold, Bloomberg reported in April. 

But other former WeWorkers are diving into entrepreneurship.

Middleton, who was an angel investor pre-WeWork, joined Boston-based venture capital firm Flybridge in 2016. Before investing in Shampine's pre-seed round, he led a $5 million seed round in Teal, a career coaching startup led by Dave Fano, WeWork's former chief growth officer. Middleton also invested in Narrator.ai, a customer data analytics platform founded by former WeWork data engineer Ahmed Elsamadisi, as well as some WeWork alumni's startups operating in stealth mode. 

Middleton said that WeWork's entrepreneurial alumni, particularly early employees, share common attributes no matter their startup's business.  They home in on culture from the start, and they tend to found their companies with other former WeWorkers. And they're intensely focused on doing one thing well, because they saw how WeWork struggled with competing priorities. Now, the company is still unwinding its more extravagant purchases and noncore businesses, like a corporate jet and companies it bought along the way. 

"Adam was an amazing salesperson and taught everybody how to think 10 times bigger than they could've before," Middleton said. "Of the WeWork employees who go out and want to build things, you don't see small ideas." 

Shampine, who helped launch WeWork in Asia and then became the head of South Korea, left the company in October. In March, he started Dongnae, a South Korean residential real estate-focused platform, with Insong Kim, WeWork's former chief of staff in South Korea. Dongnae's head of design, Annie Kim, was the design director for WeWork Korea. 

Dongnae's registration day
Dongnae's cofounders register their new company at a government office
Matt Shampine
Dongnae recently raised a pre-seed funding round with angel investors that include other WeWork alumni, and Shampine said he's planning a seed round later this summer. True to its founders' roots, the startup's office is in a Seoul WeWork.

Shampine said he's aiming to continue the network-building work he did at the office giant, like putting together small dinners to bring founders together locally. 

"The ecosystem is like New York was 10 years ago," he said. 

South Korean real estate: even more difficult than New York City 

When Shampine moved to South Korea five years ago to launch WeWork in Asia, he said he found the apartment search process even more taxing and opaque than in New York City.

Unlike the US, where large brokerages like Compass have more than 12,000 agents, South Korea has hundreds of thousands of small brokerages employing a handful of people, Shampine said. Without a central listing service like Zillow or Redfin, Shampine couldn't find information to easily compare multiple apartments. 

To simplify the process, Dongnae is building out a customer relationship management tool and an internal listings platform. The company will open its first brokerage branch in August, with brokers who will work with customers from search through move-in. 

With $3.3 billion in brokers' fees from residential transactions and rentals annually, Shampine said he sees a big enough opportunity in South Korea to focus on the domestic market.

And he's still using his WeWork connections, including Middleton, to connect local entrepreneurs with the people he met across the world during his WeWork tenure. 

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