Jessica Livingston

Jessica Livingston25 posts

Jessica Livingston is a venture capitalist and author from Boston. She is a founding partner of Y Combinator. In 2007, she published Founders At Work, a collection of interviews about startup companies. She previously worked at Adams Harkness Financial Group as the company’s VP of marketing. She has a BA in English from Bucknell University. She is married to Paul Graham, and they have two children.

9 Feb, 2015

Regrets not funding Indiegogo


Livingston talks about not investing in Indiegogo:

We didn’t interview Indiegogo when they applied to YC back in 2007 or 2006. We didn’t even invite them to interview, so I guess that would be a dumb business move. In our defense, they were raising funding for indie movie projects, so it isn’t the same thing as it is now. But I really love their founder, Danae Ringelmann. I think she’s awesome. So I’m equally sad that we didn’t fund her, from a personal perspective.

9 Oct, 2014

Bloomberg interview


Graham and Livingston are interviewed together for the first time. They talk about the selection process for Y Combinator companies, how the best founder teams are genuine friends rather than people who are just working together, and why Graham stepped down. Graham on how to initiate a startup:

The best way to start is not to start. Don’t even start a startup. Start a project.

Livingston on whether the firm would consider follow-on investments in successful projects:

We never say never, but the problem is that is that there’s a signaling thing. Follow-ons would hurt the founders who are probably a great investment but that we just didn’t choose to do a follow-on with.

21 Aug, 2014

Hit on by VC


While waiting for an interview with Re/Code, Livingston is hit on by a male investor.

I’m not crazy, right? He was hitting on me? He was offering to invest in our weaker companies as a way to get me on a date, right? Did that just happen? Today, of all days. I just can’t believe it would be today.

Livingston has taken a stand against sexual harassment.

Y Combinator has a zero tolerance policy for inappropriate sexual or romantic behavior from investors toward founders. Don’t even think about doing it. I will find out.

On why she has taken her stand:

There are so many new investors coming into the Valley from New York and everywhere else, and we just wanted to lay that out there. The overt sexual harassment you read about — the men who say they don’t invest in women — I can’t force them to invest in women, but I can say you can’t sexually harass our founders. And so that’s what I did.

15 Aug, 2014

Stanford interview


Livingston gives an on-stage interview for an entrepreneurship course. She says people who aren’t naturally good negotiators can learn, but that being genuine gives investors the right message:

You really don’t want to go outside your comfort zone, you’ve got to be you…investors are funding you for you, you’re going to be CEO of this company

Entrepreneurship Through the Lens of Venture Capital: Jessica Livingston, Y Combinator

20 Apr, 2014

Women 2.0 interview


Livingston talks at the conference about whether founders need an accelerator:

What I would probably do if it were me…if you were a seasoned entrepreneur and have done 10 startups and have heaps of investor connections, maybe you don’t need an incubator

She says successful founders have still come back to Y Combinator:

[…] They know this three months is going to be super-intense and it almost forces them to be productive and get stuff done, so we still add value.

Fireside Chat: Succeeding Within and as an Incubator Jessica Livingston (Partner, Y Combinator)

28 Feb, 2014

Startup Grind 2014


Livingston is interviewed onstage about Y Combinator companies, approaching Ron Conway, and whether starting a startup has become a trend:

I think it’s steadily increased. There was definitely a spike when Social Network came out [and] Facebook went public…when we started in 2005 it was not a mainstream thing to do.

She says Y Combinator is getting applicants that are further along, and different founder demographics like older people and family teams:

There are definitely people applying to Y Combinator that are much farther along than they used to be … now it’s people doing Series A at the same time as coming to us

On how non-profits can become more efficient:

We’re hoping that the non-profits can learn that if you apply some of the techniques that the startups do like move fast, launch early, listen to your users…some of those things can make the non-profits better

Jessica Livingston (Y Combinator) at Startup Grind 2014


Conway at Startup School 2013


Livingston interviews Conway about his investments, and what he thinks is the future of social apps. Conway:

I don’t know because I’m not a founder, but I’m sure people out there [in the audience] have ideas on what is the next social app, because social apps are changing the way people communicate

Ron Conway at Startup School 2013

27 Jun, 2013

Startup Grind 2013


Livingston says being able to show revenue growth, tie-ups with larger partners, and a solid product are all ways founders can get investors’ attention. But they must have a long-term goal:

Communicate what the grand vision is down the road….that’s very important to investors

Jessica Livingston (Y Combinator) at Startup Grind Silicon Valley

2 May, 2013

New York Times feature


The newspaper profiles the firm’s Demo Day, speaking with Graham, Altman, and Livingston about the company’s strategy for picking startups to support. Graham:

Imagine an assembly line where Facebooks and Googles come along every few years. You can either pick that cookie off the assembly line or not. If you pick it off, it’s market price, which varies. But if you don’t pick it off, you’re out of the game.

2 Sep, 2011

GigaOM interview


Livinston talks to GigaOm about what qualities Y Combinator partners look for in founders who apply.

First and foremost, the cofounder relationship is extremely important… Second, have the founders built something before?… Another quality I think is important is kind of being flexible-minded, or open-minded…. I always say the most important quality in any founder is being determined, and that is probably the toughest quality to judge in a 10 minute interview.

What Y Combinator looks for in a founder


YC Founders at Work: Posterous


Livingston interviews Tan and Agarwal, founders of Posterous. Asked about how close their original version was to the current version of the site.

It’s actually pretty close. Sergei and I have always been bloggers. The two of us since high school, have always had a personal website that has our thoughts and photos…We were using all these tools. I was using Blogger and Xanga, and we were really frustrated with the tools we were using.. And they were really text based. The idea was that blogging meant having to type out a whole lot of text. Nobody wants to type out text, nobody wants to read it — it’s really boring. We wanted to share photos. Now how do you put photos on the web? Now have to use Flickr, and now I want to share videos — I have to use YouTube. And there really wasn’t a solution to get rich media onto the web…And between all of that email was the unifying protocol that made a lot of sense…The initial prototype was: I want to send an email and I want it to appear on my blog.  The first 20 lines of code written were to post from email.

YC Founders at Work: Reddit


Livingston interviews Ohanian about the early days of Reddit. Livingston asks about the “Chicken and egg” problem of building a community with no initial users:

This is one that I have no hesitation in saying, but it always stirs up a lot of controversy. Steve [Huffman] built a really simple system for admins, that is Steve and me, so that when we submitted a link also let us type in a user name. It let us easily and efficiently create lots of fake users. And we were able to browbeat a few of our friends to build up comments. But the rest of our friends and family could not be begged or bribed enough to do it really consistently. The only option we had to resort to was to fake it. But we didn’t have to do it for too long because Paul [Graham] did us a big favor  by [profiling us] us in an early essay.

It was at some point about three or four weeks into it that neither Steve or I had to submit or vote on anything, and the site just worked…We could spend the day just lurking on Reddit, that is just using it like the vast majority of people do and not actually generate content. That was huge. That was when we realized, maybe we haven’t wasted this summer and we had a legitimate community.

YC Founders at Work: Dropbox


Livingston interviews Houston, founder of Dropbox. On finding cofounder, Arash Ferdowsi:

That was definitely one of the bigger struggles getting started– having this idea and not having a co-founder. And Paul [Graham] and everybody told me over and over again that this was a necessary condition of joining Y Combinator. I was networking around and letting people know about DropBox and seeing what they though and met Kyle Vogt, a founder of Kyle had dropped out of school to join and it turned out that he and Arash were both undergrads at MIT, and both from Kansas. The same kind of cabin fever that I had being in Cambridge and watching all my friends move out to Silicon Valley I think Arash was feeling too. So, I put up the screencasts, three or four minute video, about Dropbox and Arash emailed me after that, because Kyle let him know I was looking for a co-founder. We met up at the coffee house at MIT and everything went from there.

YC Founders at Work: AirBnB


Livingston interviews Chesky and Gebbia from AirBnB:

We had a month of runway left, we had very little money in the bank, and had to figure out how to make the next rent check….There was a design conference coming to San Francisco. And here we were thinking we need to make money and we need to meet people. So we put the two together and decided why not make a little designer bed and breakfast for the design conference? We noticed all the hotels were sold out… and that was the lightbulb for us. We pulled out a coupe of Airbeds and we had the original idea: Airbed and Breakfast! We weren’t trying to start a business. We were trying to solve our own problem.

20 Apr, 2007

[email protected] interview


Livingston says she wrote Founders At Work as there was a lack of information about the early stages of a company.

I thought, the bankers and analysts at my [finance] company don’t really understand what happens at companies until they go public…the truth is, noone really knows what happens in the first few years of startups except the founders and the people who work there

She did 32 interviews over the course of two years:

I tried to collect this really interesting fund of experience for…people who are thinking of starting a startup, or want to go and work for one, or are just interested


Wozniak interview


Livingston interviews Wozniak for Founders At Work about starting Apple. His advice for people considering starting a startup:

First of all, try to have the highest of ethics and to be open and truthful about things, not hiding. If you have to hide something for company reasons, at least explain what you’re doing. Don’t mislead people. Know in your heart that you are a good person with good goals because that will carry over to your own self-confidence and your belief in your engineering abilities. Always seek excellence: make your product better than the average person would.

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