Karn Saroya is the CEO and cofounder of Cover, which was in the YC Winter 2016 batch.Cover is a nationally licensed insurance brokerage. You can use their app to take a picture of property you want to insure and they’ll connect you with their insurance partners so that you can get the best price and coverage.You can find Karn on Twitter at @karnsaroya.The YC podcast is hosted by Craig Cannon.***Topics00:36 - Karn’s intro01:01 - Using computer vision to identify and catalogue property2:28 - How Karn ended up starting Cover3:48 - Being a maker vs. an advisor5:58 - Stylekick, Karn’s previous startup9:28 - Joining Shopify10:08 - How the idea for Cover happened11:58 - The capital-light way to start an insurance business16:28 - Underwriting17:58 - Lead generation20:18 - Product development21:28 - Buying Cover.com for $750k24:53 - Being engaged to a cofounder28:43 - Managing two offices and cultures30:58 - Being an international founder in YC31:58 - Advice to people in the current batch of YC

Caterina Fake hosts the podcast Should This Exist? which is about how technology is impacting our humanity. It launches today on iTunes. She also cofounded Flickr, Hunch, and Findery and is an investor at Yes VC.Kat Manalac is a partner at YC.You can find Caterina on Twitter at @Caterina and Kat at @KatManalac.The YC podcast is hosted by Craig Cannon.***Topics00:32 - Caterina's new podcast, Should This Exist?2:32 - Is there a process for considering if something should exist?4:02 - Who should be part of these conversations?5:17 - Wait But Why and the Human Colossus7:22 - Episode 1 of Should This Exist?10:17 - Having conversations before things exist11:42 - How might employees think about their role in whether or not something should exist?14:32 - Caterina reflecting on her creations and if they should exist19:02 - Considering whether things should exist as investors23:32 - Cofounder charter - What you will and won't do26:03 - Questioning the VC model27:22 - Working on Wall St, feeling herself change, and quitting31:22 - Caterina as a student34:02 - Peculiarity and entrepreneurship35:22 - "Don't fight to win prizes that aren't worth winning"38:32 - What was once fringe is now mainstream40:52 - Kat looking up to Lea Salonga42:42 - Evgeny asks - How did she get her first 100 paying users?49:27 - How does she advise founders to find investors?54:47 - What questions should founders ask themselves while making something?

Ryan Hoover is the founder of Product Hunt which was in the Summer 2014 YC batch and was acquired by AngelList. He also invests in startups through his Weekend Fund.Dalton Caldwell is a Partner at YC where he runs admissions.Ryan is on Twitter at @rrhoover and Dalton is at @daltonc.The YC podcast is hosted by Craig Cannon.***Topics00:27 - Ryan's intro00:52 - Dalton's intro1:27 - Forming Product Hunt and applying to YC5:17 - Product Hunt's growth rate when they applied to YC6:27 - Raising money for the right reasons9:42 - Maker communities11:27 - Why raise money for Product Hunt?13:12 - Having buzz during the batch18:12 - Brex changing their idea during YC20:17 - Pivoting into something you know well21:32 - In retrospect, how would Ryan have advised himself around monetization?28:27 - Trying to build out other verticals34:27 - Don't act like you have infinite runway35:57 - Creating urgency and developing products within AngelList40:17 - Tips to launch on Product Hunt45:07 - What Dalton looks for in applications46:57 - Giving people the opportunity to start48:47- What motivated Ryan to leave his job before Product Hunt

Jake Klamka founded Insight. Insight provides intensive 7 week professional training fellowships in fields such as data science and data engineering. Insight was in the YC Winter 2011 batch.Kevin Hale is a Visiting Partner at YC. Before YC Kevin was the cofounder of Wufoo, which was funded by YC in 2006 and acquired by SurveyMonkey in 2011.You can find Jake on Twitter at @jakeklamka and Kevin at @ilikevests.The YC podcast is hosted by Craig Cannon.***Topics00:37 - Kevin's intro01:07 - Jake's intro1:42 - Applying to YC with one product then changing it4:07 - How Insight started4:57 - Jake's first students and initial coursework8:37 - Finding out what companies want from data scientists10:37 - Picking the first class of students12:07 - Common pitfalls for people transitioning into data science15:07 - Types of data science roles17:22 - What data scientists should look out for in companies18:17 - Chuck Grimmett asks - When do you know you need to bring in seasoned data scientists?20:37 - How Insight has scaled and changed22:37 - What happens in the program23:57 - Examples of a good project for a data science resume26:27 - Will more data scientists be founders in the future?28:37 - Teaching product29:37 - Cleaning data32:07 - Tools for tracking data32:57 - Track what are you trying to optimize35:57 - Churn and conversion39:37 - Is there an ideal background for a data scientist?41:37 - Which startups recruit well at Insight?43:37 - Contracting46:17 - Fields Jake is excited about

Avni Patel Thompson founded Poppy, which helped parents book the best caregivers. They went through the YC Winter 2016 batch and recently shut down. Avni asked to come on the podcast to talk about what the process of shutting down was like.Kat Manalac is a partner at YC.You can find Avni on Twitter at @APatelThompson and Kat at @KatManalac.The YC podcast is hosted by Craig Cannon - @CraigCannon.***Topics00:35 - Kat’s intro01:15 - Avni’s intro2:15 - When did it become clear that scaling Poppy wasn’t working?5:50 - Experiments Avni tried with Poppy9:55 - The last six months of runway13:25 - Choosing to shut Poppy down17:25 - Pivot or shut down?20:10 - Who did Avni have these hard conversations with?24:35 - Communicating with investors during the process of shutting down31:20 - How does Avni feel since shutting down Poppy?38:30 - Tying self-worth to your accomplishments and how it feels after shutting down39:30 - “This is what trying looks like.”44:00 - The effects of having raised money46:00 - Starting to think about what’s next49:00 - Struggling with unstructured nothing49:45 - Kindness

Samantha Bradshaw is a researcher at the Computational Propaganda Project and a doctoral candidate at the Oxford Internet Institute. She’s been tracking the phenomenon of political manipulation through social media.You can find Samantha on Twitter at @sbradshaww.The YC podcast is hosted by Craig Cannon.***Topics:53 - What is a bot?2:53 - When computational propaganda began3:53 - Changes in bot tactics since 20165:53 - Using bots for content creation7:28 - WhatsApp and the upcoming Indian election9:23 - Trends in computational propaganda10:53 - How bots integrate into platforms13:23 - Responsibilities of platforms to remove fake accounts14:53 - The role of governments in media manipulation18:18 - Fake news and selecting news that aligns with your beliefs19:53 - Are platforms getting better or worse?21:33 - Samantha's personal internet habits23:03 - Sentiment around tracking in the UK vs the US24:23 - The Mueller report and US midterms29:18 - Canadian elections30:18 - 2020 US elections30:53 - Deepfakes31:48 - Optimistic thoughts for the future33:08 - How to help against computational propaganda

Cindy Mi is the founder and CEO of VIPKID. VIPKID is a 1-on-1 teaching platform where children in China learn english from North American teachers.Qi Lu is the CEO of YC China and Head of YC Research.***Topics00:23 - Qi's intro00:38 - Cindy's intro1:38 - Moving to a new province as a teenager4:38 - Being an educator and an entrepreneur 8:23 - Starting VIPKid in a hyper-competitive market14:53 - Metrics for measuring product market fit21:43 - How did she find the business model?26:53 - What things did she try that didn't work?30:38 - Strategy for product expansion33:03 - Content expansion for Mandarin learning34:53 - Building global companies41:23 - Creating a global culture44:13 - The future of education48:08 - How should engineers and product managers think about edtech?51:33 - Thoughts on AI54:33 - Advice for entrepreneurs

Vinod Khosla is the founder of Khosla Ventures, a firm focused on assisting entrepreneurs to build impactful new energy and technology companies. Previously he was the founding CEO of Sun Microsystems, where he pioneered open systems and commercial RISC processors.How to Build the Future is hosted by Sam Altman.***Topics00:30 - Vinod’s intro01:20 - A zero-million-dollar company vs a zero-billion-dollar company4:20 - What percentage of investors in Silicon Valley are good long-term company builders?4:50 - Who has earned the right to advise an entrepreneur?6:50 - Which risk to take when7:20 - Helpful board members8:15 - Who to trust for what advice11:00 - First principles thinking and rate of change13:00 - Evaluating a candidate in an interview14:15 - How much should a founder have planned and how ambitious should a founder be?16:30 - Recruiting great people19:00 - Building a phenomenal early team20:20 - Being generous with early employee equity27:00 - Gene pool engineering27:18 - The art, science, and labor of recruiting28:20 - How founders should think about investors31:00 - Doers vs pontificators32:00 - What does Vinod want to do in the next ten years?32:10 - Reinventing Societal Infrastructure with Technology

Frank Lantz is a game designer and Director of the NYU Game Center. He cofounded Area/Code Games and most recently released a game called Universal Paperclips in which you’re an AI that makes paperclips.Frank’s on Twitter @flantz and his site is franklantz.net.The YC podcast is hosted by Craig Cannon.***Topics00:27 - "Games are the aesthetic form of thinking and doing"6:57 - VR skepticism9:42 - Universal Paperclips14:27 - Explaining games to non-gamers20:12 - Competitive gaming22:57 - Building life lessons into games31:42 - Teaching game design36:17 - Inspiration, hard work, and taste39:17 - Darker sides of gaming culture43:07 - The indie game market45:27 - Unexpected trends in gaming49:17 - Benedict Fritz asks - Frank you seem much more interested in chess, go, poker, and other games with a long history than most game designers. Where do you think this comes from?52:12 - Esports55:37 - Inventing sports57:27 - Pokemon Go1:00:32 - Difficulty in predicting successes in entertainment1:03:17 - Frank's game recommendations1:05:47 - @fakebalenciaga asks - Why Tonto?

Reham Fagiri and Kalam Dennis are the founders of AptDeco, where you can buy and sell used furniture. They were in the YC Winter 2014 batch and you can find them at AptDeco.com.The YC podcast is hosted by Craig Cannon.***Topics0:21 - What is AptDeco?1:06 - Why did Reham and Kalam start it?2:51 - Were they considering other ideas?5:06 - How did they prepare to start AptDeco after business school/the corporate world?6:21 - Getting over the fear of starting9:21 - Communicating that they're starting something to friends and family14:21 - Starting a startup after business school17:21 - Helpful learnings from a more traditional business education27:21 - Early models of AptDeco vs today31:51 - AptDeco's customers34:06 - Brands and customer acquisition38:46 - Learning how to do delivery42:06 - Deciding not to warehouse furniture43:51 - Ideas that didn't work and some that worked on the second attempt48:21 - Analytics50:51 - Being a NYC company in YC52:11 - How to make the most of YC