Rejected, Then Accepted: Our Y Combinator Application, Twice
Hundreds of cold emails with zero replies, forty customer conversations, a top-10% rejection – and what we changed to get into YC six months later.
Our first month of “doing sales” at Lingo.dev produced hundreds of cold emails and not a single reply – not one demo, not a single “no thanks,” even.
It was early 2024, in Barcelona.
We’d won a hackathon a few weeks earlier, and about twenty people were using our localization tool – some of them genuinely loved it, messaging us about the hours it saved them. But love from twenty users doesn’t pay rent.
My co-founder Veronica and I had followed Y Combinator from a distance for six years – Paul Graham’s essays, the podcasts, the “someday we should apply.” We knew we could build almost anything; we’d proven that to ourselves already. What we hadn’t proven was that anyone would buy it, and it was time to find out which we were: a company, or two builders from Eastern Europe tinkering in Spain.
Step one: learn to sell.
The Book
Everyone pointed at Founding Sales by Pete Kazanjy. Amazon Spain didn’t carry it, Amazon US wouldn’t ship it, so I complained on Twitter.
A stranger replied – Brad van Leeuwen, co-founder of Cledara, who happened to be flying to Barcelona the following week.
He bought a copy, put it in his carry-on, and seven days later handed it to me at a coworking space on La Diagonal. The whole thing started with a favor from a man I’d never met.
We tore through the book together, passing it back and forth – cold outreach, email structure, follow-up cadences – and then executed it to the letter: hundreds of personalized messages to CTOs and engineering managers, each follow-up sent exactly on schedule.
Nothing happened. Not a single demo, not even a polite “not interested” – just silence, day after day, refresh after refresh.
We assumed real founders had some secret template, so we asked a few we’d met at events to show us their actual outreach emails – the ones that had worked. They did, and the emails were... fine. More polished than ours, sure, but the structure was similar and the tone was similar. No magic anywhere.
Which meant the problem wasn’t the format – it was the content. We were writing about features, our tech, what we found impressive, with no idea what our buyers actually cared about, what words they used, what kept them up at night. We were guessing, and we were guessing wrong.
Forty Customer Conversations
So we stopped selling and started asking.
The new message went out with no company name and no demo: “We’re exploring how teams handle localization. Would you be open to a 30-minute conversation? No pitch, just trying to learn.”
And people said yes.
Over the next two months we did somewhere between forty and fifty of these conversations, each one built on the same three questions: How do you handle localization today? What’s the most frustrating part? If you had a magic wand, what would the perfect solution look like?
After about twenty conversations, a pattern started to emerge; after forty, it was a script. The same phrases kept coming up, near verbatim, from people who had never spoken to each other:
“Translation delays are killing our release cycles.”
“We waste hours on string management.”
“The handoff to translators is a mess.”
We rewrote everything – landing page, emails, pitch – in their words instead of ours, and stopped describing what the tool did in favor of naming the pain it killed.
Within a week, we booked our first real demos.
The lesson wasn’t about sales; it was about sequence. We’d been charging at step two before doing step one. We thought we had a sales problem when we actually had a research problem – and once we solved that one, the sales started happening on their own.
Our First YC Application: Rejected
Mid-2024, we submitted our first Y Combinator application, and a few weeks later the rejection email came.
Deserved, in hindsight. We’d skipped the demo video – “nobody wants to watch a terminal app,” we reasoned – and that was exactly backwards. YC routes applications to partners who know the domain, and a devtools partner isn’t bored by a terminal; they enjoy using it. We’d hidden our best evidence. On top of that, we had almost no traction: a handful of users, no revenue, no proof anyone would pay.
One detail worth knowing: YC rejections come in tiers – ours said top 10%. Not great, but not nothing.
That night we made a rule: never judge yourself on one application. We’d reapply in six months and let the delta be the verdict – real progress by then would mean we were on the right track, and no progress would mean rethinking everything.
Then we went back to work. Paying customers started arriving – not many, but real ones, credit-cards-out real. One was Cal.com, the open-source scheduling tool, and working with them set our tempo: they’d ask for a feature and we wouldn’t roadmap it – we’d build it, push it to production, update the docs, and reply in the same thread, “Done. Here’s how to use it,” sometimes within the hour. One night around 10 PM, already heading home, a message came in that our users needed something. We looked at each other, called an Uber back to the office, and shipped the feature at 1 AM.
The YC Interview Is Ten Minutes
In the fall of 2024, YC announced something we hadn’t planned for: a brand-new fall batch, their first ever, with applications open months ahead of our schedule. We applied anyway – and did everything differently this time.
We recorded the demo video. We cut the application in half and made it twice as clear – no fluff, no hedging, just the facts, and this time we had paying customers and a real story to tell. Then we messaged about a hundred YC alumni asking them to review the draft before we submitted; ninety ignored us, but the ten who answered gave notes that were surgical – unclear phrasing, claims without evidence, key facts buried below the fold.
We submitted. This time, we got an interview.
The YC interview is ten minutes – that’s it, ten minutes to convince a room of partners that you and your co-founder are worth betting on. So we booked mock interviews with alumni, five to ten calls where they played YC partner and fired questions at us like the real thing.
One of those calls I’ll never forget. The guy joined and skipped the greeting entirely: “All right, I don’t have a lot of time. What are you building?”
We gave our pitch – localization tools for developers, ship to new markets without thinking about translations.
He cut us off. “I’m going to be honest with you. I just interviewed another team with exactly the same idea. And I think this idea is bullshit.”
Then came ten straight minutes of artillery – why would anyone pay for this, isn’t this a solved problem, how do you compete with Google Translate – hard and fast, no room to breathe. My face went hot, and Veronica went rigid beside me.
Then he stopped, and his voice changed completely. “Okay, that was staged. I wanted you to feel what it’s like when someone comes at you hard. You guys actually have a solid product.”
It was the most useful thirty minutes of the entire process. When you’ve faced the hardest questions in rehearsal, the real thing loses its teeth.
On interview day we joined the call early, palms sweating, and answered direct questions with direct answers – product, traction, why us – no rambling, no filler. Ten minutes later it was over, and we sat staring at each other in that strange silence after something important ends, unable to tell if we’d nailed it or blown it.
A few days later, YC asked for another call – a technical deep dive. We got on, demoed everything, answered every question they had. And right there, on that call, they told us we were in.
Everything changed after that. But that’s another post.
What I’d Tell Anyone Applying to Y Combinator
Four things I’d tell the version of me from that first month, hundreds of emails out and nothing back:
Research before selling. Talk to fifty people about their problems before you pitch anything. When the same phrases start repeating like a chorus, that’s not noise – that’s your landing page, your emails, your pitch, in their words instead of yours.
Always include the demo. Even if it’s “just a terminal.” The reviewers who matter will get it, and the ones who don’t weren’t going to fund you anyway. YC’s own interview guide says the same thing: have a demo ready, or a demo video available.
Borrow scar tissue. Alumni will review your application and mock-interview you if you ask – and almost nobody asks. It’s an enormous advantage, and the price is one polite message.
Run everything as an experiment. Every week, ask honestly: am I closer to the goal? If the answer keeps being no, change the approach or change the goal – and be willing to see it clearly, especially when it hurts.
We thought the path to YC was a straight line through a better sales email. It wasn’t. Sometimes the way to where you’re going runs through somewhere else first.
Questions people ask us about applying to YC:
How hard is it to get into Y Combinator? YC’s own numbers put the acceptance rate at about 1% of applications – the Winter 2024 batch took 260 companies from over 27,000 applications. We got in on our second attempt: the first application was rejected (top-10% tier, no demo video, almost no traction), the second – six months later, with paying customers and a demo – got an interview and an offer.
How long is the YC interview? Ten minutes, over video call. In our case it was followed a few days later by a second, longer technical deep-dive call, and the acceptance came during that call.
Do you need revenue to apply to YC? No, but it changes your odds. We applied with a handful of users and no revenue and were rejected; we reapplied with paying customers – including Cal.com – and got in. Traction turned our claims into evidence.
Should you include a demo video in your YC application? Always – even if your product is a terminal app. Applications get routed to partners who know the domain, and a devtools partner reads a terminal demo fine. Skipping it hides your best evidence.
Does YC tell you how close you were after a rejection? Some rejection emails carry a tier – ours said “of the applications we read this batch, yours was in the top 10%”, and other founders report the same line. We used it as a baseline for the reapplication six months later. YC doesn’t give individual feedback below the interview stage.
Can you reapply to YC after being rejected? Yes, and reapplying with visible progress is a signal in your favor – in the Winter 2023 batch, 59% of accepted companies had applied more than once. We treated the delta between our two applications – users, revenue, product – as the verdict on whether we were on the right track.
Love this writeup Max and really enjoyed your writing style next to your content! Keep writing :)
love it! continue posting more newsletters, it is really good to read someone sharing honest things about the startup road