Founder Stories: Guy Goldstein’s Make-Or-Break Bet With Check

To listen to Guy Goldstein, the CEO of Check (formerly Pageonce), tell the story, you’d think he never sweats under pressure.

Six years ago, Goldstein helped found what is now Check, a mobile payment company that helps people track their finances and do payments, moving about $500m in payments a year. But, the path to get here wasn’t linear and required a big, make-or-break bet.

Check started out as a web company, but Goldstein quickly realized the company wasn’t acquiring enough users and the team needed to admit things weren’t working. Luckily for them, this was around the time of the new iPhone, so they bet the company entirely on mobile in about three months (after building Facebook apps that failed) and became one of the first apps in the App Store. At that time, they couldn’t even get funding for the mobile product, so had existing investors support them.

Goldstein relays this story with a founder’s excitement and humility, sharing lessons about how he selects investors, why it’s important to celebrate the highs in startup life, and how his team is precise about having colleagues in Palo Alto and Israel travel back and forth to make sure there are strong bonds at the company. For any company that has or will face a make or break situation, Goldstein’s story is a must-watch.

Editor’s Note: Michael Abbott is a general partner at Kleiner Perkins Caufield & Byers, previously Twitter’s VP of Engineering, and a founder himself. Mike also writes a blog called uncapitalized. You can follow him on Twitter @mabb0tt.