Before It Clicked

Raj Suri built Presto after one painfully slow restaurant bill split turned into an obsession. In this episode, he breaks down how he got the idea, why he worked inside a restaurant before building, how he found his first customer, and what founders get wrong about picking markets vs products. This is a sharp episode on idea formation, validation, founder conviction, and surviving when you’re too...

Ryan Rzepecki had no hardware background and no software background. But in 2008, he saw the Paris bike share system, thought the $5,000-per-bike infrastructure cost was insane, and started building a smarter alternative — a smart lock on a bike, unlocked with your phone.What followed was a 10-year journey of product pivots, near-bankruptcy, and relentless grinding. His parents mortgaged their...

Scott Woody left Dropbox with no idea, no code, and no product. What followed was months of deliberate exploration — a LIDAR startup, a nanny company, workflow software — before a random conversation with HashiCorp unlocked the wedge that became Metronome, a billing infrastructure company that just sold to Stripe for $1 billion.In this episode, Scott breaks down the exact methodology he used to...

PostHog just raised $75M Series E at a ~$1.4B valuation—but the real story is what happened before it clicked.In this episode, PostHog co-founder James Hawkins walks through the 6 pivots that came before PostHog: why early-stage is brutally hard, how they decided what to build next, and the exact moments that told them they were finally onto something.We cover:Why 0→1 is harder than $1M→$100MThe...

Dover is one of those YC companies that looks “obviously successful” from the outside. But the real story is way messier: they hit PMF with a product called Autopilot, scaled fast, and then the 2022 hiring crash basically deleted their market overnight.In this episode of Before It Clicked, Sunny Rekhi sits down with George Carollo (cofounder of Dover) to unpack what it actually feels like to lose...

Genius is an institution on the internet—the go-to destination for anyone wanting to know what a Drake or Bad Bunny lyric actually means. But before it was a global music powerhouse with over 200 million monthly visits, it was a "passion project" being built on nights and weekends.In this episode of Before It Clicked, I sit down with Genius co-founder Tom Lehman to deconstruct the journey from a...

What does it actually look like to pivot eight times in a single year? In this episode of Before It Clicked, Sunny Rekhi sits down with Alex Danilowicz, co-founder of Magic Patterns, an AI design tool that helps product teams skip Figma and go straight to working UI.Alex shares the raw, "dark days" journey of moving from a viral iMessage analytics side project to the high-stakes environment of Y...

Dave Salvant and his co-founder Songe had no technical background, no barbershop experience, and were burning through their seed money. With only $60,000 left in the bank, they made a desperate "all-in" bet: they used 30% of their remaining cash to buy a barbershop in New York City.In this episode, Dave reveals how "becoming the customer" by operating a physical shop was the secret to building...

Vouch is now a $550M company, supporting 6,000+ high-growth companies. But they did it by rejecting the core tenets of startup wisdom.On this episode of Before It Clicked, we dive into the early, messy days of Vouch with co-founder Sam Hodges. In a world that preaches "move fast and break things," Sam reveals why his team adopted the "Fat Startup" strategy—a calculated, capital-frontloaded...

Two founders with zero healthcare experience built the first iPad-native EHR app… and found explosive PMF even though they started DrChrono before the iPad existed.In this conversation, Daniel Kivatinos (co-founder of DrChrono) walks through how an outsider team broke into one of the most regulated, slow-moving industries and still reached a nine-figure exit. We cover:1. Why Daniel and Michael...