Chi-Chao Chang is a widely respected tech executive who formerly worked for Yahoo, then had a 24-hour stint at Clinkle. Vimeo/Trustee Last December, employees at stealth payment startup Clinkle had two consecutive all-hands meetings. The first was to announce a big new hire, Clinkle's VP of engineering Chi-Chao Chang. The second was to announce his sudden resignation.

Clinkle first made headlines last summer when its 22-year-old founder, Lucas Duplan, announced a $25 million seed round of financing from top tech investors. It was called the largest early-stage round of financing ever raised in Silicon Valley.

Since then, the product has suffered major setbacks, employees have been laid off, and a lot of Clinkle's executive team has turned over. Its VP of engineering, director of customer service, VP of design, VP of operations, and chief operating officer have departed.

The first of those departures was Chi-Chao Chang. He was employed by the startup for exactly 24 hours, then he quit.

His resignation came as a shock to everyone, including Clinkle's CEO Lucas Duplan and former COO Barry McCarthy, who had carefully vetted Chang. He came highly recommended from credible people in Silicon Valley, such as Carol Bartz, a former CEO of Yahoo. Chang was a former executive at Yahoo and xAD.

What made Chang quit so suddenly?

A Clinkle insider close to Chang explained why he might have left.

According to this person, Chang decided to join Clinkle just after Thanksgiving. But when he accepted the offer, he wasn’t confident about the decision. Clinkle was a secretive company, and it wouldn’t divulge the true state of its product — or, more important, the plan for the company’s turnaround — to an outsider. The only way Chang could truly find out if he could help Clinkle was to join it.

He went into his first day of work determined to collect more information about the company’s product, road map, and management team for further due diligence. By the end of the week, he’d know whether he should stay at Clinkle or move on.

On his first day, Chang picked up a discouraging piece of information. The company was planning another round of layoffs. It had only been two months since the last cut, and many of the people who were going to be fired were hardworking employees who had proven their dedication to Clinkle’s mission.

Counterintuitively, the company wanted to go on a hiring spree after the layoffs, bulking up its engineering and executive teams, which would be costly. Chang, the insider says, couldn’t help wonder why a seed-stage startup wanted to fire hardworking employees and bloat the company with expensive higher-ups rather than focus on getting the product launched.

In addition to learning about the layoffs, Chang found the product and its marketing strategy in poorer shape than he anticipated. One person who saw his face during a walk-through of the product said he appeared “dumbstruck.”

But the insider says the product didn’t scare Chang away. If Duplan oversold it during the interview, he was just being overzealous like most startup founders are. Plus, hard work wouldn’t have scared Chang. He knew he was hired to get the app ready for launch.

A faulty app was something Chang could more or less fix. But disagreeing with the company’s management team about the direction of the company was harder to get past.

Chang left his first day of work feeling uneasy. He called Duplan that evening to share his reservations. The conversation lasted well into the night. The next morning, Chang told Duplan he wouldn’t be coming back to the office. He left a long list of recommendations about how to launch Clinkle, then they parted ways amicably.



Of course, the only person who really knows why Chang left is Chang.

When reached for comment, Chang declined to elaborate, saying, “Lucas is one of the most impressive people I have ever met. I believe he will lead Clinkle to a successful outcome and I wish them the best.”

To read the full story of Clinkle, check out: A SILICON VALLEY DISASTER: A 21-Year-Old Stanford Kid Got $30 Million, Then Everything Blew Up >>