Livingstone started iStockphoto in 2000 as a project offering stock photos for free over the internet. In 2002, high monthly bandwidth bills prodded him to implement a payment/credit system. In 2006, Livingstone sold iStockphoto to Getty Images for $50 million, where he continued on as iStockphoto's CEO. Livingstone picked up additional roles at Getty (including SVP Consumer) but left Getty and iStockphoto in 2009.
In 2013, unhappy with the direction of iStock under Getty (and following the expiration of his non-compete agreement) Livingston founded Stocksy United, a royalty-free stock photo and video agency based in Victoria, BC.
- Rasbach, Noreen (June 3, 2009). "Hot Stock". Report on Business Magazine. The Globe and Mail. Retrieved February 16, 2020.
- Shankland, Stephen (March 23, 2009). "iStockphoto founder, CEO leaves Getty". CNET. Retrieved February 16, 2020.
- Purvis, Mifi (October 11, 2013). "Calgary's iStock founders are back in competition with Getty Images". Canadian Business. Retrieved February 16, 2020.