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After two startups that couldn't find product-market fit, Todd Olson became obsessed. He read Steve Blank's book and felt like it was "speaking to me personally." He promised himself he'd never prematurely scale again. Todd Olson is the founder and CEO of Pendo, a product experience platform that helps software companies understand user behavior. He started programming at 14 - packing a suit to high school every day so he could work at a bank every afternoon. For Pendo's entire first year, Todd only measured one metric: installs. Not revenue - just how many companies put Pendo's code in their product. He hit 50 installs before closing a single paying customer. His first deal came when he called a company that was screenshotting Pendo charts for their board meetings and said, "You should probably pay for this." They paid $500/month - and they're still a customer today. Stay for 27:01 to hear what happened when he raised prices 10x overnight and his sales team panicked. 🔑 KEY LESSONS 📉 Two failures drove a product-market fit obsession: Todd's first two startups never found fit. After reading "Four Steps to the Epiphany," he obsessed over validating fit at Pendo before scaling anything else. 🎯 Track installs, not revenue, to validate early demand: For Pendo's first year, Todd only measured installs - getting customers to put code in their product - reaching 50 before closing any paid deal. 🤝 Founder-led sales reveals what's missing from your product: Todd refused to hire salespeople until $500K ARR. Staying in every deal surfaced missing features like surveys that won Pendo's then-largest customer. 💰 A 10x price increase proves product-market fit is real: Todd raised Pendo's minimum from $99 to $1,000/month overnight. The sales team panicked, but closed just as many deals at the new price. 🛠️ What you refuse to build becomes your differentiator: Todd skipped track events for five years despite every competitor offering them. Auto-tracking became Pendo's key differentiator. ⏱️ TIMESTAMPS 00:00 Introduction and the Fred Smith quote 02:27 Starting as a programmer at 14 03:44 The dot-com boom and first startup 06:15 Why the first acquisition deal fell apart 07:41 Second startup and failure to find product-market fit 09:49 Reading Four Steps to the Epiphany 12:06 Living the Pendo problem at Rally Software 14:07 Validating the idea with VCs and founders 15:41 Building autotrack from day one 18:33 Saying no to sessions and track events 20:23 Getting first 50 installs and first paying customer 23:49 Founder-led sales to $500K ARR 26:35 Why he refused to hire salespeople early 27:01 The 10x price increase that transformed the business 30:54 Figuring out the ideal customer profile 33:44 Pricing strategy and the $99 to $1,000 leap 37:24 Reintroducing free and product-led growth 37:56 The hardest part of building Pendo 39:57 Lightning round 42:05 Where to find Todd and Pendo 🎧 Full Show Notes: https://saasclub.io/451 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email #SaaS #ProductMarketFit #SaaSPricing #FounderLedSales #StartupStory