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

Right after I graduated from my high school, I went to a local hospital that said, "Oh, there's a 1 cm tumor in your thyroid." And the doctor confirmed that it's actually thyroid cancer. Hearing this unpredicted way really changed my mind of viewing things in the world. One of the core ways I make decisions right now or after that incident is if I were to die after 10 years, would I be doing the things that I'm doing right now? If you're putting 10 years of a timeline, you can eliminate all the other side tracks and excuses that was clouding your vision and the things you want to achieve in life. Obviously, helping AI to automate grunt work of humanity is meaningful. But at the same time, I don't think there's enough founders who are thinking to use AI to empower humanity. If we cannot empower humanities with AI, we lose purpose. There's no meaning as humanity to evolve as AI gets smarter and smarter than us. I urge all the smart and young founders to go after bolder and harder problems to solve. Act on it. Be bolder than others. Make bold bets. If you act on these bold opportunities, you'll be getting surprisingly bigger returns. Hi, I'm Yun, CEO and co-founder of Pensive. Pensive is an AI learning platform help instructors to grade much faster reducing grading time from 60% to 90% without losing accuracy. We recently raised $6.8 million seed round led by Mayfield fund followed by anti-fund reach capital base ventures sequoia capital and a6 scouts. We really think we can reimagine higher education to be more affordable more personalized and more accessible using AI. I was born in a small island in South Korea. In Korea, which university you are graduating from matters a lot in civil society success. So when I when I look back in my elementary schools and in middle school years, I would study by myself until 2:00 a.m. to really keep up and really be competitive with my peers. But then when I was turning 14, it kind of hit me. What am I getting after studying hours and hours and being stressed? And I would just read books in different subjects to really try to find an answer with this very question. Why am I studying so hard? What is it for? That's the time when I first found out about founders, people like Steve Jobs, Bill Gates who would create something new making impact globally. And I was just fascinated by their stories. I want to be like them. I want to be like those legendary founders who would make great impacts in the world. And my dad's first reaction was founders like Steve Jobs and Bill Gates. They are geniuses and you don't have the DNA. Yun, you just have to study hard, get to a good university in Korea and then just become a lawyer. Looking back, I do agree in the claim that founders are special people. But at the same time, I didn't think that I'm unccapable of becoming a founder. So other than just obeying to his words were kind of coming down, I really thought if I make this $100 as an allowances that I have saved so far in my piggy bank to $200 and bring back to my dad, he would now believe that I'm worthy of the founder. So I went to a Korean street market and then try to sell backpacks and it was freezing cold and no one wanted to buy a backpack. So I remember u I failed selling a single backpack for 2 hours. My hand was frozen like this because I was grabbing my back like this. So now I I try to uh sell in different ways and using a different strategy where what is unique to myself. Oh, it's it's my story like why am I selling these packbacks in the first place? I was mainly targeting people who seemed like who would have a son like me. So I'll reach out to them and say the thing I'm selling to you right now isn't a backpack. It's a memory. Every time you're wearing this backpack, you'll think of like myself selling these backpacks in a freezing winter in the street market even though you are down or you have some challenges like you are going throughout the day you'll be thinking of those memory and then getting some courage. So I sold my first backpack with that story. But then one thing hit me once again where is this one I wanted to do as a founder? I wanted to found a company that is longlasting creating something durable and something new. That point on I decided if I want to be a founder I need to be technical. I need to learn the hard skills so that I can build the softwares and I can build a product so that I can sell because I really wanted to start a generational global company. Coming to Berkeley I founded my first company after a month I entered to the college. That's how much I really wanted to found a company and be entrepreneur. Prior to the current direction of founding Pensive, I was pivoting eight times throughout the whole year and going through a lot of these processes. There was something missing. I was looking at the market. I was looking at the pain points. I was writing the hypothesis and then we were validating each hypothesis, building scalable small MVPs, talking with the users, all the necessary things that YC is telling the teams. The biggest thing that was missing was a founder market fit. Am I a founder who can actually pursue this idea for the next 10 years? If you don't have a purpose and a mission to really solve these problems, I think it's very challenging to wake up every day and be excited to solve that problem. One of the core ways I make decisions right now is I just think that I will be dying after 10 years. Right after I graduate from my high school, I got diagnosed by thyroid cancer. And even though thyroid cancer is the most curable cancer, that was a complete chaos from my family, my friends, myself, I was shocked. I never knew that I'll be diagnosed by cancer at the age of 18 when I thought I have decades of life to live, but yet I'm diagnosed with cancer. I have a possibility of dying in in the next 5 years. Hearing this unpredicted way really changed my mind of viewing things in the world. If you only have 10 years of your life, would you actually do that? If you're putting that into perspective and you're putting that 10 years of a timeline, suddenly you can eliminate all the other sid tracks and excuses that was clouding your vision and the things you want to achieve in life. Oh, I want to get more credentialed. I want to get my master's degree. I want to get my PhDs and then I want to found my startup if you only have 10 years of your life. Would you actually do that? That really puts into perspective and make me ask myself what is the most important quality and how do I want to spend the next 10 years of my life in the most critical way that you can ever imagine because you simply don't have time after that 10 years. So that was a learning where in the early days when you're venturing around these idea maze what you really have to listen is obviously the market and the idea itself but at the same time do we have found the market fit I love a framework called eeky guy eeky guy is a framework where when you're choosing something to do you have to consider four different things altogether you should do a thing that you love you should do a thing that you're good at you should do a thing where the world needs and you should do a thing which you can paid for. So when I think about the things I really care a lot and the world needs, there are three major problem sectors that I'm really interested. Learning and education, energy and climate change and healthcare and curing cancer. Now the thing that I was good at, I thought I was particularly good at experience at learning and education. Prior to founding Pensive, I worked on a lot of machine learning models and language models and adopting them inside education at a company called grid. And working in a fast growing startup that grew 20 times, I learned a lot of how to operate an educational startup. And what are the things that I should be mindful of as well as the expertise and the domain knowledge that I was gaining as the research scientists in that field. And that's why I believe learning and education as a whole is a sector that I love, the field that I'm good at, the field that I we can be paid for, and especially now the world needs the most. So investors were surprised how quickly we're executing because when they hear edtech and especially selling to colleges, they freak out. They don't want to invest. Adtech is traditionally one of the hardest sector yet venture scalable outcomes in higher red. So the execution speed of our team was the most surprising point given how slowly the sector moves. Coming to Berkeley, the first class I took was called CS61A. It had 2,000 students taking the same class. So we had to get the largest auditorium in the entire campus to host the entire students. I could barely see my professor's face and professors obviously wouldn't even remember my name. It doesn't have the same resources as MIT or Stanford or Carnegie Melon. It has some unique challenges. And imagine yourself, you're an instructor. Now you are grading 1,000 students worth submissions in a single day. When you were over 500 submissions, you're just mechanically circling, citing the rubrics, going to the next one just 1,000 times. I I think that was my biggest pain point when I was a tutor at Berkeley. So that's really the point the pain point that Pensive wanted to eliminate. How can we remove these routine mechanical and repetitive grading tasks so that faculties and TAs can actually focus on giving more feedback, opening more office hours, giving more group tutoring sessions. So that's where Pensive started. remember this call with a Colombia professor Tony Deer before we met him like a day before I was thinking oh why don't we just create a landing page for AI grading and show it to him and then see how he responds right so we quickly just designed the landing page in a Figma mockup we didn't even deploy the landing page as a Figma mockup and then we show that mockup to the professor after showing the AI tutor the full demo of the product for 30 minutes in the last five minutes we show to the professor hey by the way we have this new product and here's a landing page. It's an AI grader that makes your grading time much faster. Do you think you you want to use this kind of product? And he was actually saying actually the AI looks cool but AI is the thing that I need the most. I want to use AI right away. Can you can I try AI first? And that was his reaction, right? And that was when we had this aha moment. Oh, grading as a whole is a is still a pain point of a lot of instructors across the universities and as we met more and more instructors that validation game become stronger and stronger. One of my core strength and the things I did I think I did well in the past is being resourceful. Being resourceful means understanding the resources around you and really reaching out even though it feels kind of out of stretch. I will send emails to UCLA faculties. Hey, I'm visiting UCLA campus this state. If you're interested in a tool that would make your grading process much faster without losing accuracy, please book a time in my candly and I will send them a candly link. If the full day is actually booked, I would actually fly in and then meet the instructors throughout those days. If the meeting is not booked, then I would just skip the campus. So those ways I could be very efficient. I could validate the needs on specific campus and then I would fly into that campus, meet the faculties 101 and form a relationship with those faculties. That's how we got the first 10 colleges. Basically me flying around the entire nation, meeting these faculties in person and persuading them to use Pensive. Pensive's goal in 2026 is to be licensed over hundreds of universities across the nation. After that milestone of pensive, we want to go after direct to consumers, direct to students and provide and become an ideal AI native learning institutions. I think in the future AI native schools will be transferring more as a socialization environment whereas most of the components of getting some knowledge and learning new things will be happen very very intimately with 101 AI tutors happening in homes and having different environments. And we think we'll be best positioned because we know how to build the best AI teaching assistant and the assistance to really aid learning in long horizon manner. The new generation they're now being raised, they'll be never have a single chance to be smarter than Chachi. From the time they're born to the time they're dying, every single occasion, Chachi will be always smarter than them. That's why I'm founding Pensive. If we cannot empower humanities with AI, we lose purpose. There's no meaning as humanity to evolve as AI gets smart and smarter than us. Obviously, helping AI to automate grunt work of humanity is meaningful. But at the same time, I don't think there's enough founders who are thinking to use AI to empower humanity. So I urge the young founders and smart founders to go after bolder problems that would truly empower humanity with AI. Now in this era I occasionally think what is the most important quality as us humans to learn and to survive and to really make impact in this world. The most unique skills that I think people should learn is an ability to make good decisions in uncertain environments. Things are changing and they're changing very quickly. No one knows the answer and everyone has different context. It's very hard for someone else to make a decision for you and ultimately that's not your decision. My personal life moto is that every event feels like a destiny if you know your path. As you practice making those conscious decisions in uncertain situations where you don't have a full information, you are consciously making a step forward to your own path. That is a decision and that is a path that you are solely making and wholly as yourself. As these conscious choices accumulate that forms your unique path, your unique road and that road because it is accumulated by multiple and countless decisions you made as your conscious self. No one including AI can replicate yourself and your path that you have walked on. That way you can truly be unique in society and ironically that is the way to create a unique path that other people also respect. So act on it. Be bolder than others. Make bold bets. If you act on these bold opportunities, you'll be getting surprisingly bigger returns.

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 and co-founder of Pensive, an AI grading platform that cuts grading time by up to 90%. He raised a $6.8M seed round backed by Mayfield, Sequoia Scouts, and a16z Scouts in one of the hardest sectors for venture returns. But before the funding, there were 8 pivots, a father who said he didn't have "founder DNA," and a freezing cold street market where he couldn't sell a single backpack. This conversation is about finding mission, betting on bolder problems, and winning by executing. 00:00 Intro 01:57 Born Into a Lawyer's Path, Chose a Founder's 05:02 The Mission Worth My Life 08:48 Resourceful Execution Outruns the Market 12:18 What Truly Matters in the World of AGI ---------- Join Pensive's mission 🔗 Apply here: https://www.pensive.com/schools/careers 📧 Contact: hello@pensive.com ---------- EO stands for Entrepreneur& Opportunities. As we're looking to feature more inspiring stories of entrepreneurs all over the world, don't hesitate to contact us at partner@eoeoeo.net LinkedIn | @EO STUDIO X | @eostudi0