Ole is a co-founder of StepMap. Before that he co-founded Pageflakes, which was acquired by LiveUniverse in April 2008. In 1998 he was part of the Alando team, the German auction site, which was acquired by eBay in mid 1999. Ole subsequently helped eBay Germany develop the German and UK market. After that, he held marketing and business development positions for several other Internet companies including Jamba, which he co-founded, Dooyoo and MyBet. He also worked as a consultant for German media giant Bertelsmann.

Ole holds a Bachelor of Commerce with a double major in E-Commerce and Management. He also holds a Master of Business Administration with a specialization in E-Business from Griffith University, Brisbane, Australia.