Jessica Livingston

Co-founder of Y Combinator and Author of Founders at Work

THIS CHAT HAPPENED ON October 27, 2015


Jessica Livingston@foundersatwork · Cofounder, Y Combinator
Hi - I'm Jessica Livingston, cofounder of Y Combinator and author of Founders at Work. I've invested in almost a thousand early stage tech startups, so I have a pretty wide variety of information on this topic. I'm delighted to be here-- ask me anything!
Corley@corleyh · COO @ Product Hunt
Jessica, thank you for joining us today. One of your stories that resonates personally with me is the fact that you work quietly and adeptly behind the scenes. Recently the WSJ published a story about YC where your role in building the company was not acknowledged, yet Paul has called you YCs secret weapon. You've stated that this dynamic is starting to change the way you think about talking about your role, can you share more?
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@corleyh Hi Corley, I do plan to share more about this in a blog post but the short version is that being a "behind the scenes" cofounder who just focused on getting things done was a mistake. I naturally don't like attention, but I wish I hadn't given in to this so much. The biggest thing women need to start startups is more role models and had I been more publicly visible, I perhaps could have been more of one.
Corley@corleyh · COO @ Product Hunt
@foundersatwork @corleyh Thanks for your candid answer. FWIW, you are an incredible role model and mentor for many, many women. I look forward to reading your blog post.
Ryan Hoover@rrhoover · Founder, Product Hunt
Hi, Jessica! You and @pg started Y Combinator over a decade ago (!!!). As successful as its been, inevitably there are missteps. What's the biggest mistake you or YC has made?
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@rrhoover Hey Ryan!! As boring as this sounds, YC grew so organically that we didn't really have any major mistakes.
FundHer@fundher · CEO, FundHer
@foundersatwork @rrhoover Jessica, do you think it would be useful - particularly for women - if we knew more about the personal backstory of those hailed as pioneers and role models? For example, your relationship to @pg - not to judge but simply to understand and relate to one another. My hunch is many minorities might push harder, create new ways to work, succeed and even new ecosystems that support new definitions of SUCCESS if we realized the personal circumstances of those held up by the media as "role models" who made it within today's "system" - which implies and insinuates it's clearly possible/doable so if we haven't done it yet, it's "our" fault (i.e., we're failures when in fact we might be the next great innovator if we'd only known....). Often, the biggest battles many of us fight (particularly women) is in our heads. I can honestly say for years I was the biggest thing holding my back and I suspect more of us would get the hell out of our own way if we realized the standard we're comparing ourselves to isn't reality. Again, not to judge others for their personal history - simply to understand the reality of their daily lives relative to our own so those of us aspiring to be and do more don't end up feeling somehow "less than" or even giving up because we compared our reality based on giving "our all" to a false notion of what "reality" is for the role models held up as proof that success is possible (i.e., if you don't get to that level, it's on you and ultimately your fault because Sheryl, Marissa, Ariana, etc. managed to "make it.").
Edwin Espinosa@edwinespinosa09 · Angularjobs
@foundersatwork Your yoda-like "social radar" for identifying intangibles in founders has been written about many times. Have you seen recurring key characteristics in successful founders and the teams they build or perhaps in unsuccessful founders and teams? P.S. Thanks for posting on posthaven especially the Sales>Marketing
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@edwinespinosa09 Hi! Successful founders are almost invariably earnest and have a sense of mission. They are not opportunistic and in it just for the money.
Edwin Espinosa@edwinespinosa09 · Angularjobs
Thanks @foundersatwork! I've consistently heard strive for a mission that makes you hop out of bed in the AM. If anyone is interested in the Focus on Sales not Marketing article from Jessica's Posthaven check it out http://foundersatwork.posthaven....
Justin Kwong@justinckwong · Founder @ ISM (
Thanks Jessica for all that you've done to contribute to the startup community :) What are 3 things that have most surprised you about great founders who build great companies? Know you've talked about being relentlessly resourceful (determined) and getting rejected a ton as common attributes, but was wondering if there were any other surprises that you've found given all of the data points that you have. Cheers!
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@justinckwong 1) How little it matters where founders went to college 2) How critical it is to solve your own problem 3) What good people the most successful founders tend to be
Nikhil Jois@nikhiljoisr · Co-founder, Eventosaur
Hi, Jessica, Thank you for the AMA. My question is with respect to the YC invites and applications. Personally, what is that you look for first while looking at our applications? What is your take on Indian companies designed to solve Indian problems and what can they (we) gain from YC? Thanks in advance!
Varun Deshpande@varund7 · N/A
@nikhiljoisr Before Jessica answers, here's some breaking news on an Indian company that went through YC and just announced Series A ;) Good luck!
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@nikhiljoisr I look for energetic founders working on a problem that grows organically out of their lives. Indian companies working on Indian problems are great! What they can get out of YC is what any company can get out of it. Nearly all startup problems are similar regardless of what domain you are in or what country you are working from.
Bernardo Pádua@bernardops · CEO at Quero Education
Hi, Jessica, greetings from Brazil! What do you think is currently the #1 reason YC doesn’t fund more companies from other countries? How do you see YC’s portfolio regionality evolving in the mid-to-long term?
Voxiter@teamvoxiter · CEO & Cofounder, Voxiter
Hi Jessica - Kim with Voxiter here. Great to see see you doing an AMA. You folks weathered the crash in 2008 - what was that experience like for your company and your startup class? If we see another tech crash, how do you see it affecting YCombinator's model? And, selfishly; if you do another AMA, are you interested doing it on a live podcast? - we're hoping to be in your next class!
Sydney Liu@sydney_liu_sl · Co-Founder of
HI Jessica! Thanks for doing this AMA! Really awesome that you've helped democratize startup knowledge around the world. Startup School was awesome (still in touch with many people that I met there and use many of the lessons I've learned). You've told many amazing stories about founders through Founders at Work and more. The most common stories people always share is the AirBnb early days for examples of "doing things that don't scale" and focus on "early growth" and Stripe (doing "sales, not marketing"). Having met so many amazing founders, what is a founder story that you think really shows the qualities of an amazing founder that aren't talked about all the time? Thanks! Sydney
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@sydney_liu_sl I could talk about stories like this all day! Twitch is a great example of evolution and survival. The founders changed their idea dramatically several times in the course of the company. Many times they were in a situation where a pessimistic person would have thought the company was dead. They kept going and it paid off. Zenefits is an example of how powerful it can be to work on an idea that seems very unsexy. Insurance? Most people overlook unsexy ideas but Parker realized that this idea was a way in to something a lot bigger and more exciting.
Brent Summers@brentsum · Founder, Code-Free Startup
Hi Jessica, thanks for stopping by. If you were moving to SF tomorrow, what one or two steps would you take to replicate building your impressive network?
Soufian Malih@malihsoufian · Founder & product @
Hi Jessica, If you have a chance to restart the YC adventure again and can do one thing differently, what will it be? Thank you!
Hi Jessica, Any recommended reading for first time founders to get a hang of business and finance? Thanks!
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@dmurthy You don't have to know about business and finance early on. You need to know about how to build products. If you don't build a product people want, you won't have any finances anyway! If you are new to the startup world, I'd recommend watching these:
Eddie Schodowski@eddieschod
@foundersatwork What important truth do very few people agree with you on?
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@eddieschod There are a few, but these things tend to be things I'd get in trouble for if I said publicly :)
Eddie Schodowski@eddieschod
@foundersatwork @eddieschod Haha, then maybe as a follow-up: how do those types of unpopular but right insights come about? Personal experience I'm assuming?
marque jaqueson@markjackson02
@eddieschod was this question inspired by Peter Thiel? I remember this question coming up in Zero To One :D
James Kim@keembojam · Founder, Brij
@foundersatwork Hi Jessica! What is your view on part-time co-founders and how they could potentially affect a founding team? Thank you!
Pénélope Romand-Monnier@penelope_rm · Associate @Hardware Club
Hi @foundersatwork! Your book is the next on my reading list :) My question: what piece of advice you wish you had been given when you were 25yo?
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@penelope_rm Thanks Pene. I actually wrote about advice I'd give my 25-year old self a few years ago. My advice really hasn't changed:
Pénélope Romand-Monnier@penelope_rm · Associate @Hardware Club
@foundersatwork waaaah indeed it stays so accurate! totally in line with what you say in your article, I fully trust in what you wrote and I'm ready to follow your advice from now on! we'll see how it goes in a couple of years :)
Howard Haines@howardhaines
@foundersatwork What is the hardest part about what you do? Can you describe a time when you were able to help a team manage a pivot moments/decisions?
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@howardhaines The hardest part of my job is trying to figure out which companies will succeed at such an early stage. You are trying to guess not just what the founders are, but what they could grow into. Thanks so much everyone for your thoughtful and interesting questions! I have to get back to reading applications for YC's winter '16 batch. You've been a welcome distraction :)
Soliman@solimanedu · Copywriter. I really do love words.
Hello Jessica! It can be hard for some entrepreneurs to gain the necessary traction for their startups before applying to an incubator/asking for investment because most of the time, they're still beginners in the startup scene. For someone lacking the necessary tools (i.e. marketing/sales resources and expertise) to grab his/her target audiences's attention, how should he/she approach this problem? Thanks for doing the AMA!
FundHer@fundher · CEO, FundHer
Jessica, I'm curious what you'd do as a startup founder given everything you've seen, heard, said and done as a YC co-founder BUT WITHOUT the access, connections, money, advisers, etc. So you're a regular person (who happens to be a woman) with amazing wisdom enjoyed by very few people on the planet. You're a business person not a programmer but you live & breathe tech. Post-college, you spent 2 years in Finance at a Fortune 500 company. From there you spent a year in marketing at a self-funded startup which you left 2 months ago to become employee #55 a hot venture-backed startup - which was just acquired for $100 Million. None of your options vested but you got $2500 severance because you're unemployed - effective immediately. Two months later but no offers. You go back to that SaaS startup plan you drafted last year. Thanks to cloud computing, etc. you update the financials & cash flow projections now indicate you could self-fund your way to success. What would you do & why?
Danny Espinoza@abcdannye · Founder @looksyvideo
Hi @foundersatwork! What's the biggest bet YC has taken based on application/interview alone i.e. the largest delta between what the founders pitched on day 0 and what they pitched on demo day?
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@dannyjespinoza There have been a lot of startups that have changed their idea 100% between the YC interview and Demo Day. The record for idea changing is probably held by Anyperk, who changed their idea like 6 times.
Irina Jordan@irinajordan · Director of Inbound Marketing
@foundersatwork Do you follow your intuition, rely on hard data or both when making important decisions? Thanks!
Jessica Livingston@foundersatwork · Cofounder, Y Combinator
@irinajordan Mostly intuition, though data can change my mind!