Business

Year One

Every billion-dollar YC company survived a brutal first year after Demo Day. Year One captures those twelve months as they happen, tracking one founder’s make-or-break decision per episode: the pivot that saved the company, the co-founder fight that almost killed it, the fundraising round that closed at 2am on a Thursday. Two hosts (one former YC founder, one startup reporter) sit down with recent batch founders while the wounds are still fresh, then bring in YC partners to dissect what went right, what went wrong, and what the founder couldn’t see from inside the fog. If you’re an aspiring founder, an early startup employee, or an investor trying to understand why 90% of startups stall while a handful become Stripe or Airbnb, this is the show that replaces hindsight polish with the version founders tell each other at 1am on Bookface.

Latest Episodes:

The S26 Call: Two Founders, One Decision Window Jun 02, 2026

Show notes

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 seconds of silence that felt terminal, and the evening phone call that changed everything. The rejected founder already had a rehearsed answer about what went wrong — twelve users, no paid revenue — and Miles and Grant examine whether that diagnosis is honest or just the version that's easier to say out loud. Grant breaks down why the written application is the real filter, not the interview, and what separates founders who can defend a number under pressure from those who can't. If you're rebuilding for W27 or trying to understand what YC partners are actually watching, this one is worth your full attention.

The Quiet Breakdown: What Year One Actually Costs May 26, 2026

Show notes

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's 2025 survey finding only 6% of founders reported zero mental health issues. A therapist who works exclusively with founders breaks down the three clinical markers that separate burnout from high-functioning stress, including the identity fusion trap that makes asking for help feel like admitting the company itself is failing. The episode also examines what YC partners actually observe when a founder starts deteriorating, and whether investors are structurally positioned to intervene, with early efforts like Felicis Ventures' 1% Founder Development Pledge and the foundermental.health clinical survey offering a partial answer. There is no clean resolution here. If you are a first-year founder who has been performing fine while feeling nothing, this one is for you.

Jon: The Co-Founder Split Nobody Saw Coming May 19, 2026

Show notes

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 deliberate customer-sequencing strategy he used to climb from early logos like Fivetran toward Snowflake, and what YC partner data actually says about co-founder breakups as a leading killer of otherwise fundable startups. They also surface a complicating detail: Suger's Series A press materials still list two co-founders, leaving the solo-founder narrative murkier than the headline suggests. The episode closes on the structural question that outlasts the people drama: can a company scale past Series A when one person is still the single point of failure? Essential listening for any founder navigating a co-founder split or building toward their first institutional round.

W26: The Moment 'AI-Powered' Stopped Being Enough May 13, 2026

Show notes

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, where 60% of companies are AI-powered and narrative alone no longer works as cover. A YC partner names the one-sentence tell that separates a real structural moat from a well-packaged story: what would the customer have to rebuild if they left? Eight months out, the founder faces a fundraise in three months that will reveal whether the pivot produced something genuinely defensible or just a cleaner deck. With Gartner projecting enterprise AI agent adoption jumping from under 5% to 40% by end of 2026, good timing can mask weak positioning, but only for so long. This episode is essential listening for any early-stage AI founder approaching their first institutional raise.

The SAFE Trap: What a W26 Founder Signed at 2am May 06, 2026

Show notes

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 triggered an MFN cascade she never modeled and never saw coming. She admits she did not know what Most Favored Nation meant when she signed YC's standard docs. A YC partner then breaks down the two fear-based SAFE cap mistakes they see again and again post-Demo Day, and why founders who treat the cap as a confidence signal end up with a Series A math problem they cannot solve. No clean resolution here — her cap table is still on the table. This episode is essential listening for any first-time founder heading into Demo Day or sitting with an unsigned term sheet right now.

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