Year One

When Papermark founder Marc Seitz accused insurance startup Corgi of copying his open-source dataroom software word for word, the stakes escalated fast: Corgi's own CEO admitted their AI 'vibe-coding' had produced near-identical pages, then responded with cease-and-desist letters, including one over an unrelated joke tweet. On this episode of Year One, Miles and Grant break down what actually happ...

A YC-backed insurtech called Corgi shipped its Dataroom product on June 24th and was facing a public plagiarism accusation within twenty-four hours. The stakes were immediate: an AGPL-licensed open-source competitor posted side-by-side screenshots, Corgi blamed vibe coding, then sent cease-and-desist letters to the accuser and a founder who tweeted a joke about it. In this episode of Year One, Mil...

A founder inside YC's Summer 2026 batch describes day one of S26 — not the pitch, not the Demo Day narrative, the unedited version. The room was quieter than expected, and before office hours existed, real decisions were already being made: who to trust, which signals to act on, and whether to build the chip or the scheduler. In this episode of Year One, Miles and Grant pull apart the first uninvi...

Jorge B. Macías had to figure out how to sell an AI product to medical offices from Puerto Rico, scale it to millions in ARR, and do it as the first founder from the island to take a company through YC—without a traditional sales background. The stakes were high: represent a whole ecosystem on the YC stage while carrying the pressure of proving a repeatable way to win B2B deals far from Silicon Va...

Sam Altman walked into a YC event and offered every startup in the current batch $2 million in API tokens for an uncapped equity stake — and founders had to decide on the spot whether that was a gift or a trap. In this Year One episode, we get inside the deal mechanics behind OpenAI's tokenmaxxing offer: what an uncapped SAFE actually does to your cap table, and why the real cost stays invisible u...

Two founders applied to YC S26. One got in. One didn't. In this episode of Year One, Miles and Grant sit with both of them inside the moment the decision email arrived — and what happened next reveals more about each founder than the application itself did. The accepted founder had reverse-engineered proof-of-velocity signals specifically for YC's evaluation criteria. The rejected founder had spen...

Alex Benz is applying to YC Summer 2026 while already sitting on $10k MRR, four enterprise customers, and a live AI podcast platform that actually works in production—and he has to decide whether to double down now or wait for more signal. The stakes are real: timing this YC application could determine whether Mato becomes infrastructure for big podcast networks or stalls as a niche tool. You have...

Fourteen companies in the YC W26 batch hit a million in ARR before Demo Day ended — three times more than the previous winter batch and the highest count in YC history. The question Miles and Grant press on in this episode of Year One isn't whether that number is impressive; it's what it actually costs to get there in ninety days, and whether the valuation it commands is earned or a cap table trap...

Two founders applied to YC S26 in the same window. One got the interview invite. One hit June 2 in silence. This Year One episode follows both through the moment the decision became real — and what each story reveals about how YC partners actually filter thousands of applications down to a batch. The accepted founder walks through the traction question that nearly ended her interview, the four sec...

A founder walks into an all-hands meeting running the best quarter of her company's life, and realizes mid-sentence she has nothing left. Not tired. Empty. In this episode of Year One, Miles and Grant trace her burnout from month four to month nine, anchored in CEREVITY's shadow burnout research showing 73% of founders experience persistent exhaustion while still hitting their targets, and Sifted'...

Jon Yoo closed a seed round for Suger, his YC Winter 2023 marketplace startup, and then his co-founder walked out. What followed was five weeks with zero customers, a solo rebuild, and a run from $500K to $2M ARR in six months with a team of five. In this episode of Year One, Miles and Grant go deep on the moment Jon knew the split was coming and why neither side said it out loud sooner, the delib...

A W26 founder walks into an investor meeting and one question about OpenAI exposure dismantles the entire pitch in real time. The stakes are immediate: was this a company or a feature with better branding? In this episode of Year One, the founder recounts the moment they froze, and what it forced them to admit about what they had actually built. Miles and Grant dig into the W26 Demo Day batch data...

A W26 founder signed a $40M post-money SAFE at 2am in a parking lot and thought she had made it. Six months later, three stacked SAFEs had quietly committed 30% of her company before a Series A conversation even started. In this episode of Year One, Miles and Grant walk through the exact dilution math with the founder herself, uncovering how a single cap concession to close one reluctant investor...