Rob LaFave

Rob LaFave is a serial entrepreneur and investor. He’s spent the past 15 years building venture-backed companies at the intersection of technology, e-commerce, and finance, with a dash of culinary adventure thrown in for good measure.

As co-founder & CEO of Second, Rob is tackling one of the oldest problems in business: small companies grow faster than their operations can keep up. Second is an AI-native Chief of Staff platform that embeds directly into the workflows SMBs already use — email, SMS, ERP — and handles the operational load that would otherwise require an entire back-office team.

In his spare time, Rob dabbles in the world of scrumptious delights as a founding partner of Holey Grail Donuts, a cafe business centered on Hawaiian taro donuts. Rob also founded Foodzie, an online artisan food marketplace that earned a spot on Fast Company's Most Innovative Food Companies list before its acquisition in 2012.

Rob has been recognized as an Inc Magazine Top 30 Under 30 Entrepreneur, BusinessWeek's Best Young Tech Entrepreneur, and Food & Wine Magazine's 40 Big Food Thinkers Under 40.