Jessica Livingston
Born 1971 · Age 54
American investor, writer, podcaster; founding partner of seed-stage venture firm Y Combinator; author of Founders at Work; organizer of YC Startup School; advocate for female founders.
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Life & Career Timeline
Birth in Minneapolis, Minnesota
Born in Minneapolis; mother left home that year; raised largely by father and grandmother in the Boston area.
Mother leaves family; moved to Boston area
Shortly after birth, mother left home; father moved Jessica to Boston where she lived with her grandmother during the week.
Began attending Phillips Academy (Andover)
Decided to apply/attend Phillips Academy after an away soccer game; started at the boarding school in fall 1986.
Graduated Phillips Academy
Graduated from the private boarding school Phillips Academy in Andover, Massachusetts.
Began Bucknell University (BA in English)
Matriculated at Bucknell University, ultimately earning a Bachelor of Arts with a major in English (start year inferred from Phillips Academy graduation).
Graduated Bucknell University (BA, English)
Completed Bachelor of Arts at Bucknell University (graduation year inferred ~4 years after 1989 Phillips Academy graduation).
Grandmother died (day after college graduation)
Reported that her beloved grandmother died the day after her college graduation—a pivotal personal loss.
Started night-shift job at Fidelity Investments
Worked in Fidelity customer service answering investor calls on the night shift—the first post-college job she references.
Various early-career roles (investor relations, magazine, consulting, wedding planning)
Worked in investor relations in NYC, at Food & Wine magazine, at an automotive consulting firm, and briefly as a wedding planner (years approximate range mid-1990s to early 2000s).
Vice President of Marketing at Adams Harkness Financial Group
Served as VP of marketing at Adams Harkness (an investment bank); timing is pre-2003 when she met Paul Graham while working at an investment bank.
Met Paul Graham (at a party in Cambridge)
Met Paul Graham, Robert Morris and Trevor Blackwell at a party; discussions about startups and incubators began from this meeting. She was working in marketing at an investment bank at the time.
Identified and enforced YC culture ('asshole-free' rule)
Used her reputation as the 'Social Radar' to veto funding for founders she judged to be conceited or culturally harmful, shaping YC's early community and norms.
YC first summer: funded 8 startups; $6,000 per founder
In YC's first Summer Program (2005) they funded 8 startups and gave roughly $6,000 per founder (based on MIT grad student stipend), establishing the batch funding model.
Decided to run YC batches from Silicon Valley
After the first summer's success, YC committed to continue investing in batches and to run subsequent programs in Silicon Valley to claim that geographic leadership.
Co-created the batch model for accelerator funding
Helped invent the idea of funding startups in cohorts (batches) during the summer so founders could support one another and YC could scale learning as investors.
Helped create YC's founder-friendly incorporation/legal templates
Authored and organized standardized legal paperwork for YC investments so founders could avoid paying $15,000+ in legal fees to incorporate as C corporations.
Started weekly dinners / founder gatherings
Jessica and Paul hosted weekly Tuesday dinners at their Cambridge home for founders; dinners included speakers and mentorship—an early core YC ritual.
Built YC operational infrastructure (legal templates, accounts, office dinners)
Set up YC bank account, created template legal paperwork to avoid $15,000 incorporation legal fees for founders, secured speaker contacts, and converted a small Cambridge office into a gathering space.
Co-founded Y Combinator (YC) and launched website
Co-founded Y Combinator with Paul Graham, Robert Morris and Trevor Blackwell. Launched YC website in March 2005 inviting applications for the Summer Founders Program.
Hosted first Demo Day (end of summer)
Held the first Demo Day at end of Summer 2005 for about 15 investors; early YC alumni included Reddit and other founders who later built major companies.
Published 'Founders at Work: Stories of Startups' Early Days'
Released a book collecting interviews with famous startup founders, including Steve Wozniak; increased Jessica's profile as an author on startup history.
Married Paul Graham
Jessica Livingston and Paul Graham married (public congratulation post on YC news dated June 2, 2008).
Influence on YC investments (early picks such as Reddit / Dropbox era)
Early batches at YC included companies that became category-defining (Reddit in first batch; Dropbox and others in later batches); Jessica played a key role in founder selection and community-building.
Launched Female Founders Conference
Launched the Female Founders conference to inspire and encourage more women to found startups.
Leadership transition at YC; Livingston increases day-to-day involvement
When Paul Graham stepped back from his leading role and Sam Altman took over, Jessica assumed increased day-to-day responsibilities, including oversight of Startup School (approx. timing around YC leadership transition).
Summer Hackers Program / Lambda School partnership (program details)
Announced a Summer Hackers program offering 40 women $9,000 stipends to attend Lambda School's programming course; Lambda covered $12,000 tuition for participants. (Program dates indicated May 28–Sept 3; application deadline April 1; year implied in program posts.)
Advocated programs to increase female founders
Publicly championed efforts (Female Founders conference, Summer Hackers program, stipend initiatives) to broaden the pipeline of women startup founders.
Backer of OpenAI (founding backers period)
Identified as one of the financial backers of OpenAI around its founding period (OpenAI announced Dec 2015).
Relocated to the United Kingdom
Since late 2016, Jessica and her family have resided in the United Kingdom.
Oversaw/expanded Startup School responsibilities
Following leadership changes at YC, Livingston took greater responsibility for Startup School, YC's free educational program for founders (timing tied to Graham→Altman transition).
Public speaking and talks at YC conferences
Delivered multiple notable talks and essays for YC events, including the Aspiring Founders Forum and Future Founders (women) Conference—content later published on her blog.
Announced year-long sabbatical from Y Combinator
In April 2016 Jessica announced she'd take a one-year sabbatical to spend time with family and consider new projects (took sabbatical during 2016–2017).
YC milestone: portfolio ~$100 billion total value; ~1,867 startups funded
Public reporting/announcements noted Y Combinator had funded roughly 1,867 startups with a combined value exceeding $100B (figure frequently cited in the press around 2018).
Started co-hosting 'The Social Radars' podcast
Began co-hosting The Social Radars podcast alongside YC partner Carolynn Levy; interviews with prominent founders and YC alumni. Podcast activity began in 2023 (Apple Podcasts listing updated Jan 2024).
Listed as retired on Y Combinator website (cofounders retired)
As of June 2023, all Y Combinator cofounders, including Livingston, were listed as retired on the company's website.
The Social Radars listed/updated on Apple Podcasts
Podcast episodes and listing on Apple Podcasts are active (listing dated January 29, 2024).
Commencement speaker at Bucknell University
Invited to be the commencement speaker for Bucknell University's Class of 2025; published reflections and a speech on her foundersatwork site (speech available on YouTube).
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