Before It Clicked

Sunny Rekhi

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Where do great business ideas come from? "Before It Clicked" takes you inside the minds of successful business owners to find out. Join us as we interview entrepreneurs about their "aha!" moment, the origins of their innovative ideas, and the journey of building their products from scratch. Gain insights and inspiration for your own entrepreneurial path.

٤ فبراير

6 Pivots to $1.4b: PostHog Origin Story (and How They'd Do It In 2026)

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→$100M The pivot framework they used to stop thrashing Why selling to developers changed everything The launch + distribution tactics that worked How the “MVP bar” changes in an AI world James also shares what PostHog is building next—and how it could turn product analytics into actual code changes. Chapters: 00:00 Intro05:41 The 4.5-year preparation before quitting13:16 Why traditional validation is dangerous territory17:45 Targeting developers: the bluntest stakeholders26:58 The NFL child analogy: when to pivot vs. persist28:14 Why the engineer retention tool failed32:37 Improving the process: why your website is the sales team36:03 The idea maze of territory management tools44:25 Building in 2026: the magic bar for new products47:54 How to use competition as a validation shortcut56:14 The PostHog aha moment: inverting the meeting01:02:18 The Hacker News pre-mortem launch strategy01:10:34 The pivot from open source to 90% cloud revenue01:16:53 Future: code editors that build products for you

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٢٨ يناير

From $15M to $1.8M and Back: How Dover Found PMF Twice (George Carollo)

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 product-market fit, run experiments inside a ~30-person company, and claw your way back to growth. Today, Dover is a lean, profitable business doing ~ $6M in revenue, supporting ~50 recruiters on its marketplace with a ~10-person core team. What you’ll learn: - How Dover grew Autopilot from ~$1M → $3M → $6M → $15M… and what “PMF” looked like in practice - The moment the market flipped in 2022 (and why churn felt like a “light switch”) - What happens when you’ve raised $23M, hit ~85 people, and suddenly need to reinvent the company - Why Dover launched a free ATS (now used by ~1,000 companies) and a bunch of “micro-products”… and why none of it fixed the core issue - The email that sparked Dover’s second act: the Recruiter Marketplace, and the “why now” behind fractional recruiting in an AI-driven world - George’s biggest meta-lesson: we only hear the “iterate forever” stories when they work Chapters 00:00 Cold open — “This might be real… then layoffs”00:39 Intro: Dover found PMF twice03:19 Dover today: ~$6M revenue, (near) profitable, lean team05:13 2019: becoming recruiters to learn the problem07:31 “Saturated market” + the leap of faith08:48 No strong “why now” (and why that’s okay)13:49 Opportunity cost & timeboxing16:47 YC twist: Swap Space → recruiting17:42 Building Autopilot from a service19:20 PMF as a spectrum (referrals as the signal)21:34 The service→product trap: who owns outcomes?24:02 Autopilot growth: $1M → $15M24:34 2022 layoffs: losing PMF overnight29:02 The first layoff + “line in the sand”29:52 Trying to save Autopilot (self-serve, pricing experiments)30:56 Free ATS launch (and why)36:59 The “spray & pray” era (6 micro-products)38:20 The email that sparked the Marketplace42:21 Marketplace “why now”: AI leverage + spiky hiring45:10 Why agencies break (incentives + cost)47:07 Founder-led bet: team-of-one experiment (Apr→Sept)53:38 Killing Autopilot once Marketplace worked57:27 Selling the pivot internally (metrics + deck)01:03:20 Survivorship bias: “we only hear the ones that work”01:07:00 What’s next for Dover01:08:39 Hiring / recruiting partners

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٢١ يناير

How I built Genius.com with Tom Lehman

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 hard-coded 20-song website to one of the fastest-growing companies in Y Combinator history. Tom shares the tactical lessons learned from launching two failed startups (a proto-Venmo and a bedsheets business) before finding product-market fit with hip-hop exegesis. What You’ll Learn: - The "Worse is Better" Philosophy: Why releasing a "worse" version of your product to gather real-world data is more valuable than endless internal analysis. The 1 Million User Milestone: - How Genius reached massive scale and won the "search war" for lyrics before even getting into YC. Surviving 2010: - The "brutal" year of toiling in obscurity and why Tom almost quit to go back to selling bedsheets. Adversarial Growth: - Navigating the complex world of music rights and the "unethical" competition from Google that eventually led Tom to the world of crypto. The Next Chapter: - Why Tom is now building Facet, an unstoppable Ethereum layer two project. About Tom Lehman: Tom Lehman is the co-founder and former CEO of Genius (acquired by Media Lab in 2021). He is currently the co-founder of Facet, a protocol focused on decentralized computation on Ethereum. Twitter: @dumb_name_numbers Website: facet.org If you enjoyed this episode, please leave a review and subscribe to hear more origin stories from the world’s most successful founders. Chapters (00:00) Show intro(03:10) Welcome + framing the episode(04:19) Genius in hindsight — acquisition, scale, business(06:29) Life before Genius — FLIF + Bomb Sheets(10:26) When to quit vs. persevere(15:18) Origin story — “lyrics explanations” as the aha(17:45) The “Own Lyrics” thesis + why YC(30:58) Music rights overhang — publishers vs labels(39:01) Growth insight — lyrics are the “tip of the spear”(42:46) SEO + the mystery of growth(45:50) “Worse is Better” — ship → learn → iterate(49:35) Hiring & focus lessons (what he’d do differently)(52:37) Google → crypto → Facet (what he’s building now)(54:41) Beware AI-driven analysis paralysis

٥٦ من الدقائق
٧ يناير

From Pivot Hell to $1M ARR: The Magic Patterns Origin Story

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 Combinator, where they were told their initial idea was "ridiculous". We break down the specific product launches—from Chrome extensions to landing page generators—and the exact moment a "paying but non-using" customer gave them the feedback that led to Magic Patterns. In this episode, you’ll learn: The "Mom Test": Why over-interviewing users can actually slow you down. The 5 Core Tenants of Pivoting: How Alex and Teddy used a strict set of rules to stay intellectually honest. Lean Scaling: How they reached $1M ARR with just two founders before raising a Series A led by Dalton Caldwell. Side Quest Traps: Why the team initially ignored their most successful features to chase Figma plugins and email templates. Chapters: (00:00) - The feedback that birthed Magic Patterns (03:18) - What Magic Patterns looks like today (04:42) - The viral iMessage analytics origin story (11:23) - The YC acceptance call and "the pivot" (14:23) - Mirrorful: Screenshots for engineers (18:20) - Why you shouldn't take user interviews too seriously (20:53) - Dreamer: Building a landing page generator in "Pivot Hell" (23:04) - The 5 Core Tenants for finding a winning idea (26:54) - "Storybook on Steroids" and the niche market trap (32:16) - "Why aren't you using it?" The "Click" moment (43:18) - The slow burn: Launching Magic Patterns on Twitter (49:04) - From $0 to $1M ARR: Making mistakes and scaling lean (53:26) - Why a profitable company decided to raise a Series A (55:36) - Advice for founders currently in Pivot Hell

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The Barbershop Visit That Sparked a $750M Idea: The Squire Origin Story

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 Squire, now a $750M all-in-one platform for barbershops. We discuss the reality of "hand-to-hand combat" sales, paying barbers cash to stay online during outages, and the journey from a struggling idea to Y Combinator and beyond. Chapters: (00:00) - The "Make or Break" bet: Spending the last $60k (04:01) - Whiteboarding ideas at Columbia University (08:23) - Validating the idea without industry expertise (16:29) - "Uber for Barbers": Why the initial model failed (21:11) - Buying a physical barbershop to fix the software (28:40) - Surviving the fundraising struggle and Y Combinator (33:14) - How to manufacture Product-Market Fit (40:56) - The Sacramento Story: Flying cash to barbers during an outage Referenced: Squire: GetSquire.com Guest: Dave Salvant on LinkedIn Careers: careers.getsquire.com About Before It Clicked:Before It Clicked is the playbook for going from aspiring founder to business owner. Hosted by Sunny Rekhi, we explore the unpolished journey of how great ideas are born—and teach you how to replicate that discovery process for yourself. Keywords: SaaS, Vertical SaaS, Startup, Product Market Fit, Y Combinator, Venture Capital, Barbershop, Entrepreneurship, Pivot, Squire

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How to Build a $550M Company: Vouch CEO Explains Why He Ignored the "Lean Startup" Method

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 approach necessary for winning in the heavily regulated, capital-intensive insurance market. Inside the interview: The Origin Story: How a problem at Sam's previous company led to a thesis-driven effort to disrupt the $1.2 trillion insurance industry. Contrarian Strategy: Why Vouch raised a massive Series A before full launch, strategically deploying capital and hiring deep domain experts on day one to gain regulatory credibility. The "Wizard of Oz" Reality: The scrappy truth behind their early success: Sam shares the wild detail that for the first 30 policies, an engineer was manually updating database settings in real-time to "bind" the insurance. This is a must-listen for any founder tackling regulated industries like FinTech, HealthTech, or HardTech who needs a proven alternative to the lean startup playbook. Chapters: 00:00 - Intro: The "Wizard of Oz" backend 02:00 - Vouch Today: 6,000+ customers & billions in value 03:31 - Origin Story: Why insurance was the "broken" layer 06:42 - Planning Phase: Why they couldn't just "iterate" 13:56 - Unit Economics: Validating profit before writing code 18:10 - Hiring: Why Vouch hired a Chief Insurance Officer on Day 1 23:51 - The controversial decision to go Direct-to-Startup 25:46 - The "Utah Wedge": Choosing the right launch state 27:41 - The "Fat Startup" Thesis & Raising $24.5M Pre-Launch 32:14 - Business Models: MGA vs. Carrier vs. Broker 41:21 - Tech Debt: The cost of building a monolith too early 45:31 - The Innovator's Dilemma: Why legacy carriers couldn't copy them 52:43 - Launch Reality: Manually binding policies & COVID 57:05 - Navigating the 2022 downturn & SVB collapse 01:02:36 - The Pivot: Selling the underwriting arm to Hiscox 👋 CONNECT WITH US: 👉 If you enjoyed this episode, please follow the show and leave a 5-Star rating! ⭐️⭐️⭐️⭐️⭐️ Follow the Pod on X: x.com/beforeitclicked Follow Sunny Rekhi: x.com/sunnyrekhi Check out Vouch: vouch.us Resources Mentioned: Vouch: vouch.us Scale up your startup insurance: vouch.us/scale

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Building a 9-Figure Healthtech Business with Zero Industry Experience: The DrChrono Origin Story

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 Nusimow jumped into healthcare with no healthcare background 2. How they iterated with real doctors and built a product people actually loved 3. The bet on iPads before they existed 4. Lessons on intuition, fast iteration, founder psychology, and surviving years before PMF If you're a founder navigating uncertainty, doubting your idea maze, or trying to break into a legacy industry—this episode will give you the blueprint for trusting your intuition and building your way to product-market fit. Chapters: (00:00) Intro — who Daniel Kivatinos is & what DrChrono became (02:54) What DrChrono looked like at exit (thousands of doctors, millions of patients) (07:38) Daniel’s pre-DrChrono startup journey & realizing he wants his own company (20:20) Choosing healthcare without experience & ignoring strict “founder–market fit” advice (23:56) Bootstrapping with $50k in the bank and no investors (26:35) Version 1 — building a scheduling calendar doctors actually use (39:10) From scheduling to full electronic medical records & first paying customers (43:53) The empty NYC “incubator” & discovering the iPhone / iPad opportunity (47:48) One day a week on iPad — taking a controlled but non-obvious bet (55:31) iPad launch day, surprising battery life & the true product-market fit moment (57:08) Emailing Y Combinator while almost out of runway (59:23) Alexis Ohanian visits their four-startup “hub” & invites them to YC (1:06:23) Filtering customer feedback & trusting founder intuition (1:12:30) Dealing with heavily funded competitors & why speed matters more (1:18:02) Starting ⁠⁠⁠JustPaid and what he’s building now (1:24:00) Can outsiders still win today? (1:27:34) Closing advice: momentum, risk & not over-analyzing Disclosure: the acquisition price comes from EverCommerce’s public SEC disclosures, not from Daniel, who is under NDA.

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From Whiteboard to $1.5B: Airbyte's Origin Story

When Michel Tricot left his job in 2019, he didn’t have an idea yet — he just knew he wanted to start a company. Over the next year, he and his cofounder cycled through ideas: remote-controlling self-driving cars, fintech for gig workers, a healthcare data-sharing platform, and a marketing analytics product that actually had paying customers… until COVID exposed it as a “nice to have,” not a must-have. Instead of forcing mediocre product–market fit, they did the hard thing: admitted they had the right team, wrong idea, and went back to the whiteboard. From there, the team ran weekly Zoom sprints, ranking ideas by founder–market fit, team excitement, and how painful the problem sounded in real interviews. The pattern that kept resurfacing: everyone was struggling to move data reliably between tools. That insight became Airbyte — an open-source way to build and share data connectors, now used by thousands of companies and valued at around $1.5B. I’m Sunny Rekhi, host of Before It Clicked. In this episode, Michel walks me through: The dead-end ideas before Airbyte How they ran structured weekly idea sprints The moment he realized “we have the right team, wrong idea” How the open-source Airbyte thesis finally clicked Why agents are the next big consumer of data Chapters (00:00) Intro & where Airbyte is today (05:07) How Michel thinks about starting a company & idea validation (07:22) Pivot #1: remote-controlling self-driving cars (10:44) Pivot #2: fintech for gig workers (the YC idea) (16:06) Pivot #3: healthcare data-sharing & discovering “data movement” (21:22) Dexterity/DataLine: marketing analytics & the COVID “vitamin vs painkiller” moment (27:18) Realizing it’s the wrong idea & deciding to pivot again (30:40) Weekly Zoom whiteboard sprints & how they ranked ideas (40:17) Building an open-source Segment prototype → the Airbyte insight (46:50) Airbyte v1, design partners & early traction (55:25) Community explosion, fundraising & Airbyte’s future with AI agents

١ من الساعات
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12 Pivots in 5 Years to $130M: Vapi's Origin Story

Most founder stories jump straight to the win. This one doesn't. Nikhil Gupta, cofounder and CTO of Vapi, spent 5 years grinding through 12 different pivots before landing on the idea that raised at a $130M valuation. We dig into the false starts, the moments he almost gave up, the pivot that finally clicked, and the tactical decisions that separated failure from hypergrowth. You'll hear: How to know when to pivot vs. when to persistHow his ideation improved over 12 ideas What changed in the pivot that actually workedTimeline of the 5-year journey (the real one, not the polished version)This is the story before the story—no mythmaking, just the messy path to product-market fit. Chapters: (⁠00:00⁠): Cold open — “What is wrong with me?” (⁠00:19⁠): Intro — show setup & where Vapi is today (400k devs, $130M Series A, 6→45 people) (⁠02:16⁠): Meeting Jordan at Waterloo, dropping out & deciding to build a company (⁠06:13⁠): Early ideas: ETF “playlist of stocks” investing app (⁠07:54⁠): Friend CRM & betterfriend.me — first tarpit consumer idea (⁠10:33⁠): COVID learning app that got them into YC (⁠17:46⁠): Getting into YC, moving into a house & pre-batch meltdown (⁠19:30⁠): Idea framework: frequency, intensity & willingness to pay (⁠21:06⁠): Discovering the “join my next meeting” button (⁠25:21⁠): Product Hunt launch, Reddit “YC is funding button companies” & early revenue (⁠32:29⁠): Two years of experiments: Slack, focus tools & growth hacks that didn’t work (⁠42:25⁠): Auto meeting notes — listening to the computer & shipping a notes product (⁠45:27⁠): Realizing most users don’t use notes; doctors & wealth managers do (⁠47:53⁠): Shutting down a profitable product & moving to SF (⁠52:13⁠): AI therapist — Dolores Park airdrops & mental-health market worries (⁠1:00:57⁠): Turning the voice stack into an API & helping Hyperbound (⁠1:03:37⁠): March launch, virality & why OpenAI’s real-time API didn’t kill Vapi (⁠1:09:00⁠): Hiring from the community, getting to ~$4M ARR with 6 people & scaling the team (⁠1:16:30⁠): Nikhil’s closing advice

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Where do great business ideas come from? "Before It Clicked" takes you inside the minds of successful business owners to find out. Join us as we interview entrepreneurs about their "aha!" moment, the origins of their innovative ideas, and the journey of building their products from scratch. Gain insights and inspiration for your own entrepreneurial path.

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Sunny Rekhi
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٢٠٢٥ - ٢٠٢٦
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© Sunny Rekhi
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Before It Clicked

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