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How I Found a Winning Idea After 8 Pivots | Pensive, Yoon

EO15:56Added Aug 31, 2026

At 18, Yoon was diagnosed with thyroid cancer. Instead of fear, it gave him a framework: If I only had 10 years left, would I still do this?Yoon is the CEO a...

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Contributed by 刘嘉琪

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  1. Intro

  2. 00:00Right after I graduated from my high
  3. 00:01school, I went to a local hospital that
  4. 00:04said, "Oh, there's a 1 cm tumor in your
  5. 00:07thyroid." And the doctor confirmed that
  6. 00:09it's actually thyroid cancer.
  7. 00:12Hearing this unpredicted way really
  8. 00:14changed my mind of viewing things in the
  9. 00:16world. One of the core ways I make
  10. 00:19decisions right now or after that
  11. 00:21incident is if I were to die after 10
  12. 00:24years, would [music] I be doing the
  13. 00:26things that I'm doing right now? If
  14. 00:28you're putting 10 years of a timeline,
  15. 00:31you can eliminate all the other side
  16. 00:34tracks and excuses that was clouding
  17. 00:37your vision and the things you want to
  18. 00:38achieve in life. Obviously, helping AI
  19. 00:41to automate grunt work of humanity is
  20. 00:43meaningful. But at the same time, I
  21. 00:45don't think there's enough founders who
  22. 00:47are thinking to use AI to empower
  23. 00:49[music] humanity. If we cannot empower
  24. 00:52humanities with AI, we lose purpose.
  25. 00:56There's no meaning as humanity to evolve
  26. 00:59as AI gets smarter and smarter than us.
  27. 01:02I urge all the smart and young founders
  28. 01:04to go after bolder and harder problems
  29. 01:07to solve. Act on it. Be bolder than
  30. 01:10others. Make bold bets. If you act on
  31. 01:13these bold opportunities, you'll be
  32. 01:15getting surprisingly bigger returns.
  33. 01:18Hi, I'm Yun, CEO and co-founder of
  34. 01:21Pensive. Pensive is an AI learning
  35. 01:23platform help instructors to grade much
  36. 01:26faster reducing grading time from 60% to
  37. 01:2990% without losing accuracy. We recently
  38. 01:31raised $6.8 million seed round led by
  39. 01:35Mayfield fund followed by anti-fund
  40. 01:37reach capital base ventures sequoia
  41. 01:40capital and a6 scouts. We really think
  42. 01:43we can reimagine higher education to be
  43. 01:45more affordable more personalized and
  44. 01:47more accessible using AI.

  45. Born Into a Lawyer's Path, Chose a Founder's

  46. 01:59I was born in a small island in South
  47. 02:02Korea. In Korea, which university you
  48. 02:04are graduating from matters a lot in
  49. 02:06civil society success. So when I when I
  50. 02:08look back in my elementary schools and
  51. 02:10in middle school years, I would study by
  52. 02:12myself until 2:00 a.m. to really keep up
  53. 02:15and really be competitive with my peers.
  54. 02:17But then when I was turning 14, it kind
  55. 02:21of hit me. What am I getting after
  56. 02:23studying hours and hours and being
  57. 02:25stressed? And I would just read books in
  58. 02:27different subjects to really try to find
  59. 02:29an answer with this very question. Why
  60. 02:31am I studying so hard? What is it for?
  61. 02:35That's the time when I first found out
  62. 02:37about founders, people like Steve Jobs,
  63. 02:39Bill Gates who would create something
  64. 02:41new making impact globally. And I was
  65. 02:44just fascinated by their stories. I want
  66. 02:47to be like them. I want to be like those
  67. 02:49legendary founders who would make great
  68. 02:51impacts in the world. And my dad's first
  69. 02:53reaction was founders like Steve Jobs
  70. 02:56and Bill Gates. They are geniuses and
  71. 02:59you don't have the DNA. Yun, you just
  72. 03:01have to study hard, get to a good
  73. 03:03university in Korea and then just become
  74. 03:05a lawyer. Looking back, I do agree in
  75. 03:08the claim that founders are special
  76. 03:10people. But at the same time, I didn't
  77. 03:12think that I'm unccapable of becoming a
  78. 03:14founder. So other than just obeying to
  79. 03:18his words were kind of coming down, I
  80. 03:20really thought if I make this $100 as an
  81. 03:22allowances that I have saved so far in
  82. 03:24my piggy bank to $200 and bring back to
  83. 03:27my dad, he would now believe that I'm
  84. 03:29worthy of the founder. So I went to a
  85. 03:31Korean street market and then try to
  86. 03:33sell backpacks and it was freezing cold
  87. 03:36and no one wanted to buy a backpack. So
  88. 03:38I remember u I failed selling a single
  89. 03:41backpack for 2 hours. My hand was frozen
  90. 03:44like this because I was grabbing my back
  91. 03:46like this. So now I I try to uh sell in
  92. 03:48different ways and using a different
  93. 03:50strategy where what is unique to myself.
  94. 03:53Oh, it's it's my story like why am I
  95. 03:55selling these packbacks in the first
  96. 03:57place? I was mainly targeting people who
  97. 04:00seemed like who would have a son like
  98. 04:02me. So I'll reach out to them and say
  99. 04:05the thing I'm selling to you right now
  100. 04:06isn't a backpack. It's a memory. Every
  101. 04:09time you're wearing this backpack,
  102. 04:11you'll think of like myself selling
  103. 04:13these backpacks in a freezing winter in
  104. 04:15the street market even though you are
  105. 04:17down or you have some challenges like
  106. 04:19you are going throughout the day you'll
  107. 04:21be thinking of those memory and then
  108. 04:22getting some courage. So I sold my first
  109. 04:25backpack with that story. But then one
  110. 04:27thing hit me once again where is this
  111. 04:29one I wanted to do as a founder? I
  112. 04:33wanted to found a company that is
  113. 04:35longlasting creating something durable
  114. 04:37and something new. That point on I
  115. 04:41decided if I want to be a founder I need
  116. 04:43to be technical. I need to learn the
  117. 04:45hard skills so that I can build the
  118. 04:47softwares and I can build a product so
  119. 04:49that I can sell because I really wanted
  120. 04:51to start a generational global company.
  121. 04:54Coming to Berkeley I founded my first
  122. 04:56company after a month I entered to the
  123. 04:59college. That's how much I really wanted
  124. 05:00to found a company and be entrepreneur.

  125. The Mission Worth My Life

  126. 05:07Prior to the current direction of
  127. 05:08founding Pensive, I was pivoting eight
  128. 05:11times throughout the whole year and
  129. 05:13going through a lot of these processes.
  130. 05:15There was something missing. I was
  131. 05:17looking at the market. I was looking at
  132. 05:18the pain points. I was writing the
  133. 05:20hypothesis and then we were validating
  134. 05:22each hypothesis, building scalable small
  135. 05:25MVPs, talking with the users, all the
  136. 05:27necessary things that YC is telling the
  137. 05:30teams. The biggest thing that was
  138. 05:32missing was a founder market fit. Am I a
  139. 05:35founder who can actually pursue this
  140. 05:37idea for the next 10 years? If you don't
  141. 05:40have a purpose and a mission to really
  142. 05:44solve these problems, I think it's very
  143. 05:47challenging to wake up every day and be
  144. 05:49excited to solve that problem. One of
  145. 05:52the core ways I make decisions right now
  146. 05:54is I just think that I will be dying
  147. 05:57after 10 years.
  148. 06:00Right after I graduate from my high
  149. 06:02school, I got diagnosed by thyroid
  150. 06:03cancer. And even though thyroid cancer
  151. 06:06is the most curable cancer, that was a
  152. 06:08complete chaos from my family, my
  153. 06:11friends, myself, I was shocked. I never
  154. 06:15knew that I'll be diagnosed by cancer at
  155. 06:17the age of 18 when I thought I have
  156. 06:20decades of life to live, but yet I'm
  157. 06:23diagnosed with cancer. I have a
  158. 06:25possibility of dying in in the [music]
  159. 06:27next 5 years. Hearing this unpredicted
  160. 06:30way really changed my mind of viewing
  161. 06:32things in the world. If you only have 10
  162. 06:35years of your life, would you actually
  163. 06:37do that? If you're putting that into
  164. 06:39perspective [music]
  165. 06:40and you're putting that 10 years of a
  166. 06:42timeline, suddenly [music] you can
  167. 06:44eliminate all the other sid tracks and
  168. 06:48excuses [music]
  169. 06:49that was clouding your vision and the
  170. 06:51things you want to achieve in life. Oh,
  171. 06:53I want to get more credentialed. I want
  172. 06:55to get my master's degree. I want to get
  173. 06:56my PhDs and then I want to found my
  174. 06:58startup if you only have 10 years of
  175. 07:01your life. Would you actually do that?
  176. 07:03That really puts into perspective and
  177. 07:05make me ask myself what is the most
  178. 07:07important quality and how do I want to
  179. 07:09spend the next 10 years of my life in
  180. 07:12the most critical way that you can ever
  181. 07:14imagine because you simply don't have
  182. 07:15time after that 10 years. So that was a
  183. 07:19learning where in the early days when
  184. 07:20you're venturing around these idea maze
  185. 07:23what you really have to listen is
  186. 07:25obviously the market and the idea itself
  187. 07:27but at the same time do we have found
  188. 07:29the market fit
  189. 07:32I love a framework called eeky guy eeky
  190. 07:34guy is a framework where when you're
  191. 07:36choosing something to do you have to
  192. 07:38consider four different things
  193. 07:39altogether
  194. 07:40you should do a thing that you love you
  195. 07:43should do a thing that you're good at
  196. 07:45you should do a thing where the world
  197. 07:46needs and you should do a thing which
  198. 07:48you [music] can paid for. So when I
  199. 07:51think about the things I really care a
  200. 07:53lot and the world needs, there are three
  201. 07:55major problem sectors that I'm really
  202. 07:58interested. Learning and education,
  203. 08:00energy and climate change and healthcare
  204. 08:03and curing cancer. [music]
  205. 08:05Now the thing that I was good at, I
  206. 08:07thought I was particularly good at
  207. 08:09experience at learning and education.
  208. 08:11Prior to founding Pensive, I worked on a
  209. 08:14lot of machine learning models and
  210. 08:15language models and adopting them inside
  211. 08:17education at a company called grid. And
  212. 08:19working in a fast growing startup that
  213. 08:21grew 20 times, I learned a lot of how to
  214. 08:24operate an educational startup. And what
  215. 08:26are the things that I should be mindful
  216. 08:27of as well as the expertise and the
  217. 08:30domain knowledge that I was gaining as
  218. 08:32the research scientists in that field.
  219. 08:35And that's why I believe learning and
  220. 08:36education as a whole is a sector that I
  221. 08:39love, the field that I'm good at, the
  222. 08:42field that I we can be paid for, and
  223. 08:44especially now the world needs the most.

  224. Resourceful Execution Outruns the Market

  225. 08:51So investors were surprised how quickly
  226. 08:53we're executing because when they hear
  227. 08:55edtech and especially selling to
  228. 08:57colleges, they freak out. They don't
  229. 08:59want to invest. Adtech is traditionally
  230. 09:02one of the hardest sector yet venture
  231. 09:03scalable outcomes in higher red. So the
  232. 09:05execution speed of our team was the most
  233. 09:08surprising point given how slowly the
  234. 09:10sector moves.
  235. 09:13Coming to Berkeley, the first class I
  236. 09:15took was called CS61A.
  237. 09:18It had 2,000 [music]
  238. 09:19students taking the same class. So we
  239. 09:21had to get the largest auditorium in the
  240. 09:24entire campus to host the entire
  241. 09:25students. I could barely see my
  242. 09:28professor's face and professors
  243. 09:29obviously wouldn't even remember my
  244. 09:31name. It doesn't have the same resources
  245. 09:34as MIT or Stanford or Carnegie Melon. It
  246. 09:37has some unique challenges. And imagine
  247. 09:39yourself, you're an instructor. Now you
  248. 09:42are grading 1,000 students worth
  249. 09:44submissions in a single day. When you
  250. 09:46were over 500 submissions, you're just
  251. 09:48[music] mechanically circling, citing
  252. 09:51the rubrics, going to the next one just
  253. 09:531,000 times. [music]
  254. 09:54I I think that was my biggest pain point
  255. 09:56when I was a tutor at Berkeley. So
  256. 09:58that's really the point the pain point
  257. 10:00that Pensive wanted to eliminate. How
  258. 10:02can we remove these routine mechanical
  259. 10:05and repetitive grading tasks so that
  260. 10:08faculties and TAs can actually focus on
  261. 10:10giving more feedback, opening more
  262. 10:11[music] office hours, giving more group
  263. 10:13tutoring sessions. So that's where
  264. 10:15Pensive started. remember this call with
  265. 10:18a Colombia professor Tony Deer before we
  266. 10:21met him like a day before I was thinking
  267. 10:23oh why don't we just create a landing
  268. 10:24page for AI grading and show it to him
  269. 10:26and then see how he responds right so we
  270. 10:29quickly just designed the landing page
  271. 10:31in a Figma mockup we didn't even deploy
  272. 10:32the landing page as a Figma mockup and
  273. 10:35then we show that mockup to the
  274. 10:37professor [music]
  275. 10:37after showing the AI tutor the full demo
  276. 10:40of the product for 30 minutes in [music]
  277. 10:42the last five minutes we show to the
  278. 10:44professor hey by the way we have this
  279. 10:46new product and here's a landing page.
  280. 10:48It's an AI grader that makes your
  281. 10:49grading time much faster. Do you think
  282. 10:52you you want to use this kind of
  283. 10:53product? And he was actually saying
  284. 10:56actually the AI looks cool but AI is the
  285. 11:00thing that I need the most. I want to
  286. 11:02use AI right away. Can you can I try AI
  287. 11:05first? [music] And that was his
  288. 11:06reaction, right? And that was when we
  289. 11:08had this aha moment. Oh, grading as a
  290. 11:11whole is a is still a pain point of a
  291. 11:13lot of instructors across the
  292. 11:15universities and as we met more and more
  293. 11:17instructors that validation game become
  294. 11:20stronger and stronger.
  295. 11:22One of my core strength and the things I
  296. 11:25did I think I did well in the past is
  297. 11:27being resourceful. Being resourceful
  298. 11:29means understanding the resources around
  299. 11:31you and really reaching out even though
  300. 11:33it feels kind of out of stretch. I will
  301. 11:35send emails to UCLA faculties. Hey, I'm
  302. 11:38visiting UCLA campus this state. If
  303. 11:40you're interested in a [music] tool that
  304. 11:42would make your grading process much
  305. 11:43faster without losing accuracy, please
  306. 11:45book a time in my candly and I will send
  307. 11:48them a candly link. If the full day is
  308. 11:50actually booked, I would actually fly in
  309. 11:53and then meet the instructors throughout
  310. 11:54those days. If the meeting is not
  311. 11:56booked, then I would just skip the
  312. 11:58campus. So those ways I could be very
  313. 12:00efficient. I could validate the needs on
  314. 12:02specific campus and then I would fly
  315. 12:04into that campus, meet the faculties 101
  316. 12:07and form a relationship with those
  317. 12:08faculties. That's how we got the first
  318. 12:1010 colleges. Basically me flying around
  319. 12:13the entire nation, meeting these
  320. 12:15faculties in person and persuading them
  321. 12:17to use Pensive.

  322. What Truly Matters in the World of AGI

  323. 12:22Pensive's goal in 2026 is to be licensed
  324. 12:25over hundreds of universities across the
  325. 12:27nation. After that milestone of pensive,
  326. 12:31we want to go after direct to consumers,
  327. 12:33direct to students and provide and
  328. 12:35become an ideal AI native learning
  329. 12:38institutions. I [music] think in the
  330. 12:40future AI native schools will be
  331. 12:42transferring more as a socialization
  332. 12:44environment whereas most of the
  333. 12:46components of getting some knowledge and
  334. 12:48learning new things will be happen very
  335. 12:50very intimately with 101 AI tutors
  336. 12:53happening in homes and having different
  337. 12:55environments. And we think we'll be best
  338. 12:56positioned because we know how to build
  339. 13:00the best AI teaching assistant and the
  340. 13:02assistance to really aid learning in
  341. 13:04long horizon manner.
  342. 13:09The new generation they're now being
  343. 13:11raised, they'll be never have a single
  344. 13:14chance to be smarter than Chachi. From
  345. 13:17the time they're born to the time
  346. 13:18they're dying, [music] every single
  347. 13:20occasion, Chachi will be always smarter
  348. 13:22than them. That's why I'm founding
  349. 13:24Pensive. If we cannot empower humanities
  350. 13:27with AI, we lose [music] purpose.
  351. 13:30There's no meaning as humanity to evolve
  352. 13:32as AI gets smart and smarter than us.
  353. 13:35Obviously, helping AI to automate grunt
  354. 13:38work of humanity is meaningful. But at
  355. 13:40the same time, I don't think there's
  356. 13:41enough founders who are thinking to use
  357. 13:43AI to empower humanity. So I urge the
  358. 13:46young founders and smart founders to go
  359. 13:50after bolder problems that would truly
  360. 13:52empower humanity with AI.
  361. 13:57Now in this era I occasionally think
  362. 13:59what is the most important quality as us
  363. 14:01humans to learn and to survive and to
  364. 14:03really make impact in this world. The
  365. 14:06most unique skills that I think people
  366. 14:07should learn is an ability to make good
  367. 14:10decisions in uncertain environments.
  368. 14:13Things are changing and they're changing
  369. 14:14very quickly. No one knows the answer
  370. 14:17and everyone has different context. It's
  371. 14:19very hard for someone else to make a
  372. 14:21decision for you and ultimately that's
  373. 14:23not your decision. My personal life moto
  374. 14:26is that every event feels like a destiny
  375. 14:29if you know your path. As you practice
  376. 14:32making those conscious decisions in
  377. 14:34uncertain situations where you don't
  378. 14:36have a full information, [music] you are
  379. 14:38consciously making a step forward to
  380. 14:41your own path.
  381. 14:42That is a decision and that is a path
  382. 14:44that you are solely making and wholly as
  383. 14:47yourself. As these conscious choices
  384. 14:49accumulate that forms your unique path,
  385. 14:52your unique road and that road because
  386. 14:55it is accumulated by multiple and
  387. 14:58countless decisions you made as your
  388. 15:00conscious self. No one including AI can
  389. 15:02replicate yourself and [music] your path
  390. 15:05that you have walked on. That way you
  391. 15:07can truly be unique in society and
  392. 15:10ironically that is the way to create a
  393. 15:12unique path that other people also
  394. 15:15respect. So act on it. Be bolder than
  395. 15:18others. Make bold bets. If you act on
  396. 15:21these bold opportunities, you'll be
  397. 15:23getting surprisingly bigger returns.