Year One

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...