I Started 50 Businesses by 23 (and Made $10 Million!)

Jake Lewin started his first business at 13, built over 50 companies by 23, and has already had multiple exits including Lyte Leggings and Tabs Chocolate. In this episode we get into the exact growth strategy that made Tabs go viral with zero ad budget, why most of his 50 businesses failed and what the successful ones had in common, the two-year hardware grind behind his new company Dijie, and what he thinks it actually takes to build a product people can't stop talking about. Jake discusses: The Tabs Growth Playbook: How Jake pioneered the multi-account creator strategy that's now being copied everywhere, and why it only works for certain products. Reading the Market: The heuristic Jake uses every time to spot a great idea with bad execution and turn it into a business. The VC Model Applied to Creators: Why Jake thinks about influencer marketing the same way a fund thinks about bets, and why volume matters more than picking winners. What Truly Motivates Him: Why Jake doesn't think it's money, and what he thinks it actually is. Timestamps: 0:00 About Jake Lewin 1:42 How Jake made his first dollar 2:21 First $100K, first $1M, and the real Tabs revenue number 3:29 How many businesses Jake has actually started 4:27 How he finds buyers and why he doesn't recommend brokers 5:37 Why Jake doesn't want to sell Dijie 6:35 How he vets business ideas 8:56 The heuristic behind Tabs and Dijie: great idea, bad execution 11:10 What actually drives Jake to keep building 13:04 The Dunning Krueger curve for founders 14:44 The Tabs multi-account creator strategy explained 16:26 Why it works like a VC fund: you only need 1 in 100 to go viral 18:48 How to train and brief creators at scale 21:01 The incentive structure that made one creator hundreds of thousands 27:41 Viral marketing vs. a truly viral product 28:48 Growth hacks Jake actually respects: Uber, Reddit, Facebook 31:01 How Lyte Leggings grew: TikTok to Snapchat retargeting in 2020 34:36 Why being ambiguous about your product can actually convert better 36:22 What perseverance really looked like building Dijie for two years 38:02 Why hardware takes so long and what the process actually costs 41:20 Manufacturing in China: honest take on tariffs and tradeoffs 42:02 Where Jake's entrepreneurial instinct actually came from 43:55 Where to find Jake Follow Kathryn: YouTube:    / @kathrynjcross   Instagram:   / kathrynjcross   Twitter/X: https://x.com/kathrynjc7 Follow Jake: Twitter/X: https://x.com/jkelwn LinkedIn:   / lewinjake   Check out Dijie: Website: https://shop.dijie.me Instagram:   / dijie.me   Find Jake on Dijie: dijie.me/jake