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Year One
18 episodes
Nadia: What the Yes or No Actually Bought Her
Ep 21 · Aug 11, 2026 · 12 min
Nadia read the email four times and still couldn't parse it. An ambiguous status update from Y Combinator landed Tuesday night, and what followed was ninety seconds of dead air before she said a word. On this episode of Year One, hosts Miles and Grant trace the exact month leading up to her August 28th decision date: the pilot customer she chased, the six-week feature she killed after it went unused, the ops hire she postponed to protect runway, and the parallel fundraise she quietly shut down w…
Nadia: The Verdict Lands August 28
Ep 20 · Aug 4, 2026 · 12 min
Founder Nadia submitted her YC Fall 2026 application just before the July 27 deadline, and now she's twenty-four days into total silence, waiting for an interview invite she can't control. In this Year One episode, she reveals the real bets she made during the wait: an engineering hire she paused and can't fully explain, a vague team update that skirted the numbers YC applicants are told to include, and a fundraise she's put on hold, telling investors to wait until after the decision date. When…
Nadia: Betting the Raise on August 28
Ep 19 · Jul 28, 2026 · 11 min
Eight minutes before the YC Fall 2026 application deadline closed on July 27, Nadia deleted a paragraph about her co-founder — and on this episode of Year One, Miles and Grant press her on whether that was real editing or something else entirely. The stakes are immediate: her one-line pitch went through four rewrites, she bet on a smaller retention number over a bigger one, and two critical figures — her runway and her co-founder's actual equity split — never made it into the application at all.…
Mato: Turning Personalized Demos Into Onboarding
Ep 18 · Jul 27, 2026 · 18 min
Alexander Benz had a new product category, a cold lead pipeline, and only two minutes to convince confused prospects to try something they had never seen before. The stakes were simple and brutal: fix onboarding or watch high-intent YC-style leads quietly disappear. In this episode of Year One, he walks through how he turned the demo itself into the onboarding experience, from the first over-explained flows that flopped to the personalized, AI-built demo shows that now warm people up before a se…
F26: The Application Nobody Finished Yet
Ep 17 · Jul 21, 2026 · 12 min
Three weeks before her YC application deadline, a founder sat in her kitchen and stopped mid-sentence, realizing her polished traction slide left out the real reason she started the company. With July 27 at 8pm PT closing in fast, this episode of Year One follows her scramble to rewrite the story she almost submitted. Miles and Grant trace what her draft got wrong: an emotional origin story cut for a single data point, a co-founder dynamic buried in vague language, and a $500k SAFE quietly shapi…
Corgi: The Cease-and-Desist Heard on X
Ep 13 · Jul 7, 2026 · 13 min
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 happened, why identical wording (not identical code) is the real legal vulnerability, and how this compa…
Corgi: The IP Scandal Every S26 Founder Is Ignoring
Ep 12 · Jun 30, 2026 · 17 min
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, Miles and Grant talk to an S26 founder who admits they can only explain sixty to seventy percent of the…
S26 Day One: What the First Week Actually Decides
Ep 11 · Jun 23, 2026 · 15 min
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 uninvited choices S26 founders made, break down the structural information asymmetry between founders and…
Jorge: Turning BrainHi’s GTM Into an Engineered Machine
Ep 9 · Jun 16, 2026 · 17 min
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 Valley. You have to hear this one because Jorge breaks down how he turned industrial engineering tools…
S26: The $2M Token Trap
Ep 10 · Jun 16, 2026 · 16 min
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 until you're in the Series A room. Two founders from the same YC batch made opposite calls — one sign…
The S26 Email: What Getting In (and Not) Actually Means
Ep 8 · Jun 9, 2026 · 16 min
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 spent her final six weeks rewriting her bio. A YC partner breaks down the two signals that move an appli…
Mato: Betting YC Will Turbocharge AI Podcasting
Ep 3 · Jun 5, 2026 · 10 min
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 to hear this one because Alex breaks down how Mato’s AI hosts run live interviews with real humans,…
Hex Security: $1M ARR in 8 Weeks
Ep 1 · Jun 5, 2026 · 16 min
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. They pull apart Hex Security, which reached $1M ARR in eight weeks by deploying AI agents for cont…
The S26 Call: Two Founders, One Decision Window
Ep 7 · Jun 2, 2026 · 16 min
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…
The Quiet Breakdown: What Year One Actually Costs
Ep 6 · May 26, 2026 · 17 min
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…
Jon: The Co-Founder Split Nobody Saw Coming
Ep 5 · May 19, 2026 · 16 min
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,…
W26: The Moment 'AI-Powered' Stopped Being Enough
Ep 4 · May 13, 2026 · 21 min
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 n…
The SAFE Trap: What a W26 Founder Signed at 2am
Ep 2 · May 6, 2026 · 17 min
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 Mo…
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