Amid post-YC crisis, I feel the desperate need to document my life so I can reflect on it from a bird eye view. In particular, between the first moment I got exposed to silicon valley startup and when I got into YC.
A Glimpse into the Silicon Valley Startup Culture (Sep, 2024)
I withdrew from Berkely in December, 2023, and I have worked in crypto until September 2024. I was ready to wrap up my gap year and calm my mind for school next spring. But when I looked at the calendar, there was 4 months left until the spring semester.
I didn't want to waste the months, and I wanted to try something new so I started mass applying to jobs on LinkedIn. One of the jobs was a founding engineer position at Skylow, a pre-seed startup backed by MiraclePlus.
They got back to me almost immediately. I was impressed by their response time and actually got thrilled because I sensed a hyper-fast environment for rapid growth. I jumped head straight into it without much thought.
The first few months were quite fruitful. I got to learn tech stack and software engineer skills that I never had an excuse to learn at school. Full stack, web dev, mobile dev, micro-services, system design, database, sprints, project management, etc. all in actions, not just theory. I also learned that it's actually not that difficult to start a startup. There was so much I learned that I even postponed going back to school.
True for almost everything in this universe, there is always deminishing return. For Skylow, I felt that my growth is capped by the trajectory of the company. So in mid February, I quitted and defaulted to re-enroll in school next Fall.
Starting My Own Thing (Feb, 2025)
Now again, there were 6 months before school actually starts in August. So I started hacking around.
Right around that time I got addicted to scrolling on Twitter. One of the communities that I was most involved in were the indie hackers. They were building in public on Twitter and making good money living like a digital nomad, I wanted to do the same. I wanted to make good side money while I'm studying at school. So I was like, okay I want to indie hack, and I think I need to build in public, why don't I indie hack something that allows me to build in public effortlessly.
I told my sister Kaylie about this. She promised me she could find me funding to work on this. The only requirement is I would need to tell a compelling vision. I was not confident that I was a great storyteller, but I thought I could just find someone to do that job for me.
I had a candidate in mind - Sky. But the thing is I hadn't talked to Sky for a bit more than a year now. I didn't know what he has been up to, I didn't know what he had on his plate, I had basically no information on his life. I needed to gather more intel and get a feeling before even convincing him to join. I needed to vibe him out first. One call over the air is not gonna make it, so I flew to San Diego to visit him in person.
I asked a mutual friend, Sky's freshman roommate, to hang out and invite Sky along to create an occasion for me to converse deeply with Sky. Soon after we met, I got the feeling that Sky was coasting after his presidency at UCSD and had not much on his plate. So I brought up this idea nonchalantly to him. To my surprise, he eagerly volunteered to help, like a moth to a flame.
That was the starting arc of Imagine AI. It was not an intentional career choice, and most certainly not something I expected to pursue for long.
After securing a "co-founder", I flew back to the bay.
Securing Funding (Mar, 2025)
So now I have a team of two, me and Sky. Next is funding.
As planned, my sister took care of the funding part by introducing us to a bunch of her rich friends that were also doing angel investing on the side. We scraped together a prototype that barely worked while having completely 0 customer interest. But we bluffed our way and got a 30K check from the founders of Mindworks Capital, whom I knew from a separate project back in freshman year and also UCSD alums. We leveraged that to get another 30K from another angel introduced by Kaylie.
Now we have 60K! 60K was a sizable number for us at that time. Like come on it's 6 months of salary for a 120K job pre-tax, and we got that in less than a week.
Figuring It Out (Early Apr, 2025)
With 0 idea of how to actually start a startup, we did what most people would normally do, building something naively based on what we thought people would like.
We talked with a bunch of people, primarily referred to us by Kaylie. We would hop on a call with them, tell them what we are going to make, and ask them "would you use it?" Out of kindness, their response was usually something along the line of "yes definitely!".
We were hyped because we got so many "positive signals" from the friends. We went back to building and resurfaced in two weeks with a Twitter automation tool that does a bunch of things mediocrely with AI slop and doesn't really solve a single specific problem.
We brought the product back to the people we talked with earlier, trying to sell them for $20. That's the moment we realized none of them actually want it. They would tell us something nice like "maybe I will use it if you add this one particular feature". I knew they were just bullshitting me.
We had some money in the bank but we were completely lost in what to do, especially when my effort in the past few weeks got us nowhere.
It was demoralizing.
Pivotal YC Office Hours (Late Apr, 2025)
One afternoon, an email popped up in my @berkeley.edu email about YC partner visiting campus for office hours.
Usually my introverted self would just let the email go unseen. I would make up an excuse in my head that it wouldn't be "that" useful anyways with just 10 minutes, likely a complete waste of time.
But still, I screenshotted the email to Sky, "hey should I go?"
"Yes you should definitely sign up".
While uncomfortable, my ego wasn't goint to let Sky down. Days after, I got an email and a calendar invite. Now it's real, I'm meeting a YC partner in person. I was already picturing how I would pitch my idea so perfectly and bluff my way to impress him like what we did to Mindworks.
I showed up to the office hours in Eshleman Hall 5 minutes before our appointment.
The YC partner, Gustaf, was still talking to another student.
I waited in the hallway, walking back and forth thinking, "ah these berkeley students are so intense, this YC partner must have been impressed hence overran the meeting for so long to talk further, I am definitely cooked compared to that student's performance".
After 15 minutes or so, Gustaf walked that student out and greeted me in.
I sat down, rambled for 5 minutes, reciting exactly what I rehearsed in my brain for at least a dozen times.
"Okay, so who are your users?", Gustaf asked.
"Just, anyone that could be posting on Twitter...?", I didn't quite get his question.
"So, like influencers? Business owners? Engineers?", he followed up.
"I mean, yea, all of them right? Just anyone that has a need to post on Twitter I guess...?", I was still confused about the intention of the question.
The conversation went back and forth a few times. He tried extremely hard to understand our ICP while I was trying to guess the perfect answer he's looking for.
I think he eventually realized that I had completely no idea what I was doing, so he drew me a path:
- watch his video "How to talk to users";
- then charge 20 people $500 each to reach $10K MRR to prove that it's a valid problem;
- at the same time explore pivoting to LinkedIn instead of Twitter (he believes the B2B space has more money).
I walked out of the room feeling completely bummed out, "ah I fucked this up". But on the other hand, I gave myself a goal, "as long as I can charge 20 people $500, I can come back to impress him and get into YC!"
Retrospectively, I was actually giving a false hope to myself. I did believe I could impress him if I pulled it off, but I was definitely not convinced that was enough to get me into YC. But whatever, let's impress him first and we will figure out the rest.
Marching Towards YC as our North Star (May, 2025)
On top of the office hours with Gustaf, one of my freshman friends, Saarth, just got into YC around that time, so I got competitive and thought to myself "if Saarth can make it, why can't I?"
Suddenly, getting into YC became our north star goal.
I moved to San Diego and rented an Airbnb studio with Sky. We learned the YC framework, we talked to users, we consulted ChatGPT o3 every single day. We eventually narrowed down our ICP to be ghostwriting agencies instead of random people.
Learning the lesson from the painful period before Gustaf, I didn't want to waste time building software based on false positive signals anymore. I decided to start off with a clean slate by cold outbound to people on LinkedIn, proposing to custom build them a solution if they could put down a deposit ($99 refundable). We were selling our pedigree and a promise rather then selling an actual product. That got us our first group of design partners.
Integrating into the SF Startup Scene (Jun, 2025)
Fast forward to Sky graduating from UCSD. We had a handful of agencies we were working with now (8 if I remember correctly), and we were ready to move to the Bay.
We settled in Emeryville when one of my friends back in the Skylow era subleased his place to us. We also applied to a bunch of accelerators, one of them being Founders Inc. They got back to us immediately. The email was inviting us to apply for their Off Season program instead, a 6 weeks non-equity taking incubation program, and visit them on their open house (which happens to be right after my wisdom tooth surgery).
During open house, we sat down with Ruslan, one of the investment team members. He asked us a bunch of questions about what we were doing, why we were doing what we were doing, etc. The typical incubator questions.
At the end of it, he asked if we had any questions. I responded with my puffy cheek, "my question is how do we get into your program", with determination in my eyes, signaling I would do whatever it takes to get what I want. He shrugged it off with a generic answer and told us to wait for an email.
The extremely short email came in that evening, "ur in. love you guys' hustle." I don't know what exactly made him say yes, but I believe my show of determination at the end definitely skewed his decision towards yes.
We went through 6 weeks, had our first incubator experience. It was a fast paced environment with weekly check-in and occasional speaker events ending with a demo day on Aug 1.
I'm not going to go into the details of the program, but here are twos things that helped us in particular:
- we could name drop Founders Inc. to build credibility in the SF startup community;
- we became expert in making viral videos and growth hacking.
Final Touch for YC Application (Aug, 2025)
After Off Season demo day, the next chapter was naturally the YC Fall batch - the north star that we have been optimizing for.
To maximize our chance of getting into YC, we did some extra prep work, one of which is hitting up YC alums, turning them into our customers, and getting referrals from them. Alex from Prism AI (YC X25) was the first one that I converted from LinkedIn outbound. Punn from Conduit (YC W24) was the second one that I already knew from freshman year at UCSD blockchain club where we worked together closely.
Of course the most important thing was still the customer momentum we accumulated prior to the application. Oh yes, and I kept sending updates to Gustaf's email documenting our progress in customers and revenue, albeit receiving no response at all.
YC Interview (Mid Aug, 2025)
We received the interview invitation 2 days after submitting our application. We did the usual mock interview prep and showed up to the interview in person in their SF office.
David and Eric were our interviewers. They asked the canonical questions that we have rehearsed the answers for already not less than a dozen times. The interview went well and David emailed us for send over the customers list next morning for due diligence.
But when we sent over the customers list, we realized we did not do the revenue math accurately. We reported $4K as our MRR on the application but our customers list only added up to $3.3K. That rang David's BS alarm and he became skeptical. I could sense that our application was going to fall through if we don't solve this immediately.
I reached out to Kaylie. Her advice was, "don't bother the few hundred dollars, just close another deal, momentum will solve all the problems". So we did and went out to close a $3K MRR contract (we asked for a warm intro from a rich friend).
David's attitude turned 180 immediately and stopped all the scrunity. Yet, he scheduled a repeat interview for us with Pete and Diana to restart the whole interviewing process. To this day I still don't understand why a repeat interview, but I suspect David just thought Pete is a better fit as a partner to our company (Pete specializes in B2B enterprise sales).
We redid the interview, completely bombed it this time (at least in my opinion) because I did not sleep at all the night before to push a new feature. We finished the zoom call in despair. I went straight to bed. No email response for two days straight.
After three days of radio silence, we received an email for a follow up meeting the week after.
We got in, Pete told us over the meeting.
So how did we get in?
Soon after the batch started, we interrogated Pete why he let us in. Turns out during the three days of radio silence, he was doing a bunch of due diligence and the stuff he hears back got him the conviction.
Remember the emails I have been sending to Gustaf with no response? Pete consulted Gustaf and Gustaf reverted with I seem like a "smart kid". Seems like Gustaf has been reading my emails after all, just didn't want to respond. Pete also consulted Punn's experience as a customer, whom of course also reverted with good notes.
Let me quote Pete's answer verbatim, "you guys seem to have great hustles and Gustaf said you are really smart".
Special Thanks
Special thanks to the day ones Chan Bae and Kaylie Lee.