In this episode of Founder2Founder, Aaron Spivak sits down with Oleg Lee, a serial entrepreneur, Guinness World Record holder, father of three, and founder of All About Vibe, a custom pillow company that scaled from a garage operation to generating over $60 million in revenue. Known for turning people’s favorite moments into pillows, Oleg has created products for celebrities like Snoop Dogg, Gary Vee, and Paris Hilton, and partnered with brands like Netflix and Paramount.

Oleg breaks down the raw, behind-the-scenes reality of building a physical product business from scratch, how a Groupon deal triggered massive demand, working with family, and why he eventually stepped back from daily operations. He shares his goal of a $100 million exit, how he handles adversity and why focusing on health, values, and energy has been his ultimate growth strategy. This conversation is a must-listen for any founder scaling a team or navigating the chaos of entrepreneurship.

Chapters:
01:17 – The Dog Pillow That Sparked the Business
02:22 – From Israel to the U.S.: Oleg’s Early Work Ethic
04:05 – The First Custom Pillow: A Tribute to His Dog
05:13 – Building the Business in His Dad’s Garage
07:41 – The Groupon Deal That Created Instant Chaos
08:51 – Fulfilling 20,000 Orders With Family Support
09:59 – From Pre-Made to Fully Custom Designs
11:59 – Transitioning From Wholesale to DTC
12:49 – Working With His Dad: The Challenges and Lessons
14:07 – How Bringing His Wife Into the Business Saved Their Marriage
16:26 – Navigating Family Boundaries in Business
17:13 – Oleg’s Vision for a $100M Exit
19:02 – What He Would Do Differently: No Manufacturing
20:01 – The Problem With Business Advice From Non-Operators
21:30 – Pillows at VCon and Understanding Brand Psychology
23:36 – Creating a Safe and Empowering Culture for Employees
25:15 – Hiring a CEO and Fully Stepping Back
26:28 – Why He Hates Numbers but Still Leads
27:20 – Growing Up in Survival Mode in Beersheba
29:04 – Fixing Machines Himself and Leading by Example
30:22 – What It Took to Build a Self-Sustaining Business
31:37 – The Cost of Listening to the Wrong People
33:13 – Setting a Clear Target for the Exit
36:07 – Aaron’s Story of Selling Hush and Knowing When to Sell
40:34 – Why Oleg Doesn’t Share Product Ideas, He Just Builds
41:31 – Managing Remote Leadership and Scaling From Boca
43:37 – Projected Revenue and the Roadmap to $50M
44:15 – When Summer Outsold Christmas and Production Broke
46:31 – Advice to His 30-Year-Old Self: Prioritize Physical and Mental Health
49:56 – Why Health, Wealth, and Family Are Tattooed Into His Values
51:00 – Surrounding Yourself With the Right Energy

Guest Links:
Website: www.allaboutvibe.com
Instagram: @thatpillowguy

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