Jim McKelvey (Square) on Beating Amazon, The Innovation Stack and Fixing FDA Drug Trials

How does a scrappy startup beat Amazon when Amazon copies your product, undercuts your price and slaps its own name on it? According to Square co-founder Jim McKelvey, you don't. Except, once in a while, someone does. This week Sammi revisits one of her favorite conversations ever recorded for Social Currency: her sit-down with Jim McKelvey, the artist-turned-entrepreneur who co-founded Square (now Block) with Jack Dorsey. Jim opens with the story of how he once stripped down in a trade association's office just to get a meeting, and explains why getting someone's attention is always the real first step in any pitch. He breaks down why he intentionally designed Square's original card reader to work poorly, and how that "flaw" turned millions of small business owners into free advertisers for the brand. Then, Jim tells the almost unbelievable story of how Square survived Amazon's attempt to copy and kill its business with Amazon Register, why he studied history to understand how rare that survival really was, and how a conversation with Southwest's Herb Kelleher led him to write his book, The Innovation Stack. Jim also opens up about his years as an independent director of the Federal Reserve Bank of St. Louis, what he learned living through zero interest rates, the pandemic and the Silicon Valley Bank collapse, and how the role reshaped his politics. Plus, he explains why his media venture Invisibly failed to save journalism despite cracking the monetization problem, and details his newest venture, Fast Trials, an attempt to slash the cost of FDA drug trials so more life-saving drugs can make it to market. Follow Sammi Cohen on Instagram Subscribe to the Social Currency newsletter Read Jim McKelvey's blog and check out his book, The Innovation Stack Here's What Sammi Covers with Jim: 00:00 Jim McKelvey's Social Currency 02:03 Why Sammi Is Revisiting This Episode 05:09 The Striptease That Landed a Six-Figure Deal 08:00 Why Getting Attention Comes Before Any Pitch 11:01 Why the Square Reader Was Designed to Not Work Well 14:23 Respecting Your Audience's Attention 17:56 Why Jim Doesn't Use Social Media 19:00 The Power of the Pause 20:22 The Real Origin Story of Square 24:32 How Square Survived Amazon's Attempt to Kill It 28:04 The Commandment From Herb Kelleher That Became a Book 32:11 Why the Rules of Innovation Are Different 36:27 The Hardest Part of Doing Something New 37:28 Serving as an Independent Director of the Federal Reserve 40:22 What the Fed Taught Jim About Political Neutrality 42:19 The Allergic Response to Ideas That Don't Fit 43:22 Why Invisibly Failed to Save Journalism 47:04 The Monetization Model That Actually Worked 49:26 Jim's New Venture: Fast Trials 54:31 Advice for Building in Regulated Industries 58:08 Jim's Don't-Do List 59:48 Social Currency Corner: Tipping Culture 01:02:20 A Listener Question on the Future of Fintech Learn more about your ad choices. Visit megaphone.fm/adchoices