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:

Nadia: Pricing the Round Before Demo Day Nov 03, 2026

Show notes

You have to hear this one because, around week five of her YC batch, Nadia's pitch stopped feeling finished, and Demo Day is four weeks away on Wednesday, December 2. She gets sixty seconds on that stage, and a fundraising window sits right behind it, with Thanksgiving and year-end slowing everything down.

In this Year One episode, Miles and Grant start with the pause Nadia left in the tape, then look at what the middle of the batch feels like and how to rewrite a sixty-second pitch by cutting what you love. They also work through how to price a seed round against a very wide market, using Carta data and YC's standard $500K on two SAFEs. In the YC partner segment, they examine why YC credits investor competition, not brand alone, for higher valuations, and offer their own read on the first two weeks after the stage.

This one is especially relevant for founders in a YC batch, or any early-stage team heading toward a short pitch and a fundraise.

Greypoint: Proving a Four-Person Team on a Different Clock Oct 27, 2026

Show notes

Greypoint is four people in San Francisco building drone swarms, and the public record shows no contract or raise since Demo Day. That matters because the defense money they would count on is requested, not appropriated, and a slipping budget can outlast a young company's runway.

In this Year One follow-up, recorded a week before the November 3 midterms, Grant and Miles look at what is actually visible about Greypoint and 9 Mothers, including a correction: 9 Mothers is Spring 2026, not S26. There is no founder interview and no YC partner on this one. The hosts say so plainly and offer their own labeled read on what counts as signal and what is election-year noise. You will hear how Hegseth's drone command depends on a reconciliation bill with no clear path, why Breaking Defense reports 150-plus delayed new starts, and how venture money is concentrating at the big and early ends. They also cover how YC describes the post-Demo Day stretch and how to handle an investor's ambiguous maybe.

You have to hear this if you are a hardware or defense-tech founder trying to plan around a budget that may not arrive on time.

W27 Applicants: The Draft You Haven't Finished Oct 20, 2026

Show notes

You have to hear this one if there's an unfinished YC application sitting in a tab you keep opening and closing. The Winter 2027 on-time deadline is November 2 at 8pm Pacific, thirteen days from now, and it's the line between a decision by December 11 and an open-ended wait. On this Year One episode, Miles and Grant run a last-minute application clinic told backward: what applicants overthink, what they skip, and what YC's public writing suggests a partner weighs. To be clear, there's no founder interview or YC partner on this one. The hosts work from YC's published posts and secondary guides, and they label what's sourced and what's their own read. You'll hear what happens between submitting and hearing back, why the application's real job is to earn the interview, how to keep your claims checkable, what to do in the weeks before that interview, and what the YC offer looks like. This one is especially for founders with a half-finished draft who want to know what's worth their next few hours.

Anonymous Founder: Extension or Default Alive Oct 06, 2026

Show notes

You have to hear this one because it starts at month fourteen, with real users, real revenue, and a Series A bar you haven't quite cleared. Nothing forces your hand, which means you have time to make a bad decision slowly, and the stakes are whether your next round funds a plan or just hides a gap.

On this episode of Year One, hosts Miles and Grant follow a hypothetical composite founder through three options: a SAFE extension in the $1.5 to $3 million range, a priced A anyway, or cutting burn to reach default alive. They look at how common missing the bar is, what each path costs, and why an extension only works as a bridge if you name a falsifiable milestone before the money lands. No YC partner joins the conversation. Instead, they read the choice through YC's default alive definition and its 2022 guidance as reported by TechCrunch, which they flag as dated, and the founder's decision stays open.

It's especially relevant for seed-stage founders weighing an extension while their runway quietly shrinks.

Two Founders, One Year Out: The Series A Cliff Sep 29, 2026

Show notes

Two YC founders are sitting on seed rounds sized for a market that no longer exists, and neither knows yet whether they'll clear the bar. One raised in Summer '25, the other in Winter '26, both roughly a year out from Demo Day with normal $3-4M rounds and no guarantee of what comes next. This episode of Year One tracks their live, unresolved odds against a Series A threshold that has roughly tripled since 2021, now demanding $2-5M in ARR and 2-3x growth just to get a meeting. A YC partner weighs in with a cross-portfolio view spanning hundreds of startups and a $15.5M median Series A, offering a rare look at what actually separates the fifteen to twenty percent who graduate from the rest. Anyone weighing whether to grind or pivot in their own post-seed year will recognize exactly what's at stake here.

Nadia: Walking Into the Room After the $200M Number Sep 22, 2026

Show notes

Nadia walked into YC's F26 kickoff carrying the shadow of a number nobody in the room would say out loud: the $200 million valuation her company, Nine Mothers, hit as an eight-month-old startup in the S26 batch. Every founder in the new class had done the math, and Year One hosts Grant and Miles are back to find out what happens when an entire incoming cohort gets recalibrated by one outlier deal before they've even shipped a product.

This episode follows the three-day, in-person F26 kickoff in San Francisco, from the roughly 400 founders and 200 companies sorted into nine-person house groups to the moment a YC partner names the Nine Mothers print directly and coaches founders to price on fundamentals, not headlines. Grant and Miles trace how the S26 story spread through alumni nights and Bookface, why the July 27 application deadline mattered, and what December 2, 2026 now means as F26's own Demo Day countdown begins.

Anyone building through their first YC batch, or just trying to ignore a number that won't stop haunting the room, will want this one.

Greypoint: Building Hardware in an AI Batch Sep 15, 2026

Show notes

Four founders, one CNC machine, and a pitch that stopped a room full of investors cold: Greypoint Industries is building drone technology to compete with defense primes that have decades of institutional weight behind them. Jordan Khoo left General Dynamics to build LEGION, and the stakes are as much personal as strategic, invoking Canada's Avro Arrow cancellation as the mission he refuses to repeat. On this episode of Year One, Miles and Grant dig into why YC's Summer 2026 batch shifted so heavily toward industrials and hardware, what a signed Canadian government contract and armed forces demo actually prove about traction, and why hardware founders accept slower fundraising clocks and zero SaaS margins as the cost of building something real. They also unpack whether Greypoint's early buzz is signal or story. Essential listening for anyone weighing a YC application in hard tech, or founders wondering if physical products can still win in an AI-obsessed funding climate.

9 Mothers: The $200M That Warped the Batch Sep 09, 2026

Show notes

Days before Demo Day, a $200 million valuation for an unnamed S26 startup lands in a YC founder group chat and won't stop spreading. On this episode of Year One, Miles and Grant trace how that single number rewrites every other founder's negotiation in the batch, then reveal the company behind it: 9 Mothers, a counter-drone defense startup out of Austin, and the Palmer Luckey and Garry Tan context (via TBPN) that fueled the hype. They dig into Rebel Fund's data showing over a third of the W26 batch scored in YC's top tier, then pressure-test what that grade actually predicts. Michael Seibel's own 2007 Justin.tv numbers get pulled in as a reality check against today's inflated benchmarks. This one's especially useful for founders mid-fundraise who keep comparing their term sheet to someone else's headline, and for anyone trying to separate real signal from Demo Day noise.

Demo Day+72: How S26 Term Sheets Get Priced Sep 01, 2026

Show notes

The applause hasn't even faded and the phones are already lighting up. This episode of Year One picks up in the 72 hours after S26's Demo Day, when term sheets start arriving with clocks attached and top companies field hundreds of offers before the weekend is over. The stakes are immediate: sign fast on incomplete information, or risk losing a hot deal while trying to compare offers against a market that suddenly looks like 2021 again.

We break down why default SAFE caps have jumped from $2M-on-$20M to $4M-on-$40M in three years, what YC's own reasoning for same-day asks actually is, and how a generous-looking cap can quietly cost a founder more equity down the road. We also walk through a simple test for telling real investor conviction from manufactured urgency before the inbox even fills up.

Essential listening for founders staring down their own term sheet clock, or anyone trying to understand how Demo Day money actually moves.

Nadia: The Verdict Arrives Aug 25, 2026

Show notes

Nadia has just opened the YC decision email she has been waiting on for weeks, and in this episode you hear the exact moment she finds out if her company’s next year is completely rewritten. The stakes are simple and huge: either she’s in and locked into a YC batch, or she has to rebuild the plan she’s been working toward all summer.

You have to hear this one because Nadia reads the verdict out loud, processes it in real time, and immediately loops in her cofounder before she even lets herself react. From there, Miles and Grant bring the YC partner back on mic to break down what this outcome structurally changes for her next 90 days, and what the alternate path would have looked like if the answer had been no. Together they unpack what “useful feedback” really means, what founders who don’t get in actually do next, and how persistence shows up beyond the polished success stories, all through the lens of Year One decisions that compound. Published August 25, 2026, this episode is especially relevant if you’re anywhere near hitting submit on your own YC application.

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