After graduating from Ridley, Paine attended the Ivy School of Business at Western, and since then has been an entrepreneur, executive, and recently, 'angel investor', of rapid-growth, consumer-facing e-businesses. Paine was a co-founder in 1987 of Lavalife, and was CEO between 1997 and 2001. Now based in London, UK, he had been most recently focused on aggressively expanding Lavalife into European and Asian markets, and growing Lavalife's longstanding Australian businesses, which he founded in 1995. In 2000, Nick angel-invested in and ultimately performed the SVP, Marketing and Business Development role for OpenCola, a pioneering, 'Napster-era', peer-to-peer Internet "content community" concept operating in Toronto and San Francisco during the peak of the Internet bubble. Currently, he plays a financial and advisory role in several other early-stage companies. He is an active member of the Young President's Organization in London, UK, is a member of the Ivey Business School European Advisory Board, and a founding member of the Sophia Business Angels in Southern France.