The UpFlip Podcast · 2026-06-01 · 28 min
Oleg Lee started with a simple request: he asked his dad to print a custom-shaped pillow of his late childhood dog, Izzy. When he posted a photo of the lifelike pillow on Facebook, the internet lost its mind. Today, that single viral moment has evolved into a $20 million-a-year manufacturing empire producing 400,000 custom pillows annually. In this episode of the UpFlip Podcast, Oleg breaks down his unbelievable entrepreneurial journey - from stuffing 20,000 pillows by hand in his dad's garage while working full-time in construction, to becoming the silent manufacturer behind massive brands like Netflix, Paramount, and Chewy. Oleg shares exactly why he walked away from a massive retail deal with 2,000 Walmart stores to focus on direct-to-consumer (DTC) sales, how a $100,000 investment in a custom software tool doubled his revenue in a year, and the exact Instagram DM strategy he uses to land celebrity endorsements from David Dobrik, Paris Hilton, and Kim Kardashian. ️ What You’ll Learn in This Episode: The Groupon to Walmart Hustle : How Oleg survived 20,000 overnight orders out of a garage, and the harsh reality of retail margins that made him walk away from Walmart.
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