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Jody Glidden dropped out of computer science after one year, joined a startup as employee #5, and sold his first company for $1 million at 19—a deal he now calls one of his biggest mistakes because he "didn't know anything about multiples." The five-time exited founder reveals how growing up in a fishing village programmed him to clash with every acquirer's vision, why getting acquired by the same company twice still couldn't teach him to execute someone else's decisions, and the brutal math showing why going deep in a vertical beats going broad every time. This is the raw playbook from someone who built IntroHive to a $500 million valuation serving 93 countries, now runs 25 people doing what used to take 150, and has generated 100-200x angel returns—exposing why commodity SaaS is dead and what separates founders who exit from founders who get disrupted.
➡️ Show Links
LinkedIn: https://linkedin.com/in/jodyglidden
➡️ Timestamps
00:00 He Didn't Just See Data—He Saw Relationships
01:41 Born at the Right Time: The Malcolm Gladwell Outlier Reality
03:22 "It's Hard for Me to Execute Other People's Decisions"
04:01 One Year of Computer Science Then Quit—Employee #5
04:43 $1 Million Exit at 19: "Never Should Have Sold"
06:45 Pitching the LMS They Rejected—Then Becoming Their Competitor
07:35 Same Buyer, Second Acquisition: $10 Million (Still Too Early)
10:02 The BlackBerry Relay Idea: One Year Building, Zero Market
12:40 Chalk Media: Ephemeral Content Before Snapchat Existed
14:29 Raising in September 2008 (The Worst Timing Possible)
15:35 Reporting to Jim Balsilie: Learning From a Childhood Hero
16:26 Big Four Discovery: 500K Employees Who Don't Know Who Knows Who
17:52 PWC: 100 Seats to 93 Countries to $500M Valuation
18:34 The Private Equity Firm That Didn't Go Well
21:32 Going Deep in a Vertical: The Strategy That's Never Failed
22:46 25 People Now vs. 150 Before: The Vibe Coding Shift
24:13 Commodity Software Extinction: The 8090 Problem
32:39 "I've Never Had an Idea Turn Out Exactly How I Expected"
33:35 Two Equal Founders = Tiebreaker Problem (The Speak Story)
35:54 Only Invest Where You Can Move the Needle
37:40 Irrational Confidence + Thirst for Learning
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