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Jessica Livingston is an investor, a cofounder of Y Combinator, and the organizer of Y Combinator's Startup School. She is the author of Founders at Work: Stories of Startups' Early Days. Livingston is also a backer of OpenAI, which focuses on making artificial intelligence research available to all. In 2023, she launched the podcast The Social Radars with Carolynn Levy.
Livingston was born in 1971 in Minneapolis, Minnesota. Her mother left home that year, and Livingston spent much of her younger years with her grandparents near Boston, Massachusetts, so her father could work during the week. In the fall of 1986, Livingston began attending Phillips Academy in Andover, Massachusetts. She graduated from the school in 1989. She later attended Bucknell University, where she earned a bachelor of arts degree in English.
After graduating from college, Livingston began working at Fidelity Investments as a customer service representative. She later worked for an investor relations department, an automotive consulting firm, Food & Wine magazine, and investment bank Adams Harkness. She also spent a short time working as a wedding planner.
Livingston cofounded Y Combinator with Paul Graham, Trevor Blackwell, and Robert Morris in March of 2005. Livingston and Graham, who are now married, were dating at the time of the company's founding. The two met in 2003 at a party Graham was holding at his house. Blackwell and Morris were friends and colleagues of Graham; the three had founded Viaweb, an online store hosting app, in 1995. Y Combinator awards small sums of money to large numbers of early-stage start-ups. In addition to funding, Y Combinator provides its invested start-ups with business help.
After meeting Graham, Blackwell, and Morris, Livingston found herself becoming disinterested in her investment work and enthralled by the world of start-ups. She began seeking out start-up founders to interview, later publishing their stories into a book called Founders at Work: Stories of Startups' Early Days (2007). She applied for a marketing job at a venture capital firm where she felt she'd be able to engage with start-ups. After starting work there, Graham and Livingston began discussing the difficulties of funding early-stage start-ups and ways in which she could disrupt the business of venture capital.
Eventually, the couple decided to create their own start-up investment company and invited Blackwell and Morris to join. Initially, the three men were responsible for selecting and advising start-ups while Livingston handled the rest of the work. Their target audience was programmers. The Y Combinator website was launched in March 2005 with an invitation to apply for the accelerator's first financing round, “Summer Program for Startup Founders." Y Combinator awarded participating start-ups $6,000 per founder. Its first Demonstration Day was held at the end of that summer.
In April 2016, Livingston announced she would be taking a one-year sabbatical from Y Combinator to spend time with her family and consider other projects. All Y Combinator cofounders, including Livingston, are listed as retired on the company's website as of June 2023.
Startup School is a set of free educational resources provided by Y Combinator. Startup School is designed to educate and prepare people to found a start-up company and improve their odds of receiving funding from Y Combinator.
In March 2023, Livingston started a podcast with Carolynn Levy called The Social Radars, in which they interview Silicon Valley start-up founders. Guests have included the following:
- Paul Buccheit, who created Gmail
- David Lieb, creator of Google Photos
- Tony Xu, founder of DoorDash
- Garry Tan, president and CEO of Y Combinator
- Steve Huffman, cofounder and CEO of Reddit
- Tracy Young, cofounder and CEO of PlanGrid
