Digital Social Hour
The Pillow Guy: Came to America With $300. Built a 9-Figure Company. This Is His Story. | DSH #1689
16 Dec 2025
Chapter 1: How did Oleg Lee start his journey in America with only $300?
Yeah, I don't think I'll send my kids to public school. Why do you think that's the move?
Honestly, school is not my thing. I dropped school when I didn't make it to middle school. Wow. 7th grade, that was my last grade. Wow. So school is definitely not my thing. I can't even write. You know, I can speak in three languages. I can read in three languages. You can't write English? I can't. I mean, I can write, but like you don't want me to do that.
Okay, guys, we got someone on I've known for probably seven or eight years now.
Chapter 2: What challenges did Oleg face while working construction in the U.S.?
He sent me my first custom pillows. We got some here on the desk right now, too.
It's been a while.
The first ones you sent were Jersey Champs ones.
Jersey Champs, yeah. My first company.
I still have your jersey that you made for me. Oh, sick. Full circle, man. It's good to see you, though, man. How you been? Likewise. Been good. How about you? You been busy with the pillow stuff?
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Chapter 3: How did Oleg build a unique product category with custom pillows?
Busy, busy. It's a busy time now. Back to school is a pretty busy season for us. Yeah. What are your biggest clients now? Because you work with so many celebrities and all sorts of companies.
You know... Celebrities are not the biggest clients. The direct-to-consumer is the biggest business. But we do work with a lot of celebrities. I don't even know, a lot of brands as well. I mean, Kardashians, every party, they do the order from us. All the kids' parties, all their celebrations, like birthday, they always order from us. We don't work directly with them. We're like an event planner.
Chapter 4: What role do celebrities play in Oleg's business strategy?
But yeah, they've been our customer for a long time.
Impressive, man. Yeah, Eminem, DJ Khaled, Paris Hilton, the list goes on and on. Is that sort of like a marketing vehicle for you, just partnering with celebrities?
Just for the brand awareness and product awareness, yes. Yeah.
I mean, it's good quality, man. Like, you can't really get this. You can't just walk in a store and get this, right? That's why I'm the pillow guy, man.
I'm the only one who made this pillow, you know?
The first time I found you was through Logan Paul. Yeah. You were on his YouTube, right?
Yeah, I made pillows for him a while ago.
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Chapter 5: How does running marathons contribute to Oleg's leadership skills?
His dog, his podcast, you name it. I worked with him for a long time.
That's how I found you, man. So well done. Yeah. You do really well with branding and marketing. And you've been doing this for, what, 10 years now?
Yeah.
Yeah, 10 years. That's impressive.
I would say about 10 years. Not a lot of businesses last that long.
Well, my brand, All About Vibe, the actual custom shaped pillow brand has been like focused five years, but I've been trying it for over 10 years.
You started in your father's garage. Yeah, my father's garage.
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Chapter 6: What parenting lessons does Oleg emphasize from his experiences?
How old was that in the U.S.?
Yes, yeah. Two car garage, just me and him. Old sewing machine, older than me. Plastic table, that's it.
Wow, that's nuts. Did you ever think you'd get this big?
No, I never thought. But I never stopped. Today we're like 20 plus thousand square feet manufacturing and doing thousands of pills a day. Holy crap.
Yeah. When you look back and think about specific moments that were like breakthroughs, do any come to mind during the business?
No, not really. It's just consistent work.
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Chapter 7: How does Oleg define 'immigrant mentality' and its impact on success?
Never getting up. There were very bad times, but just I never quit. Okay. I kept pushing, you know.
So it wasn't like a big order that came in?
No, it wasn't any big order. It was just like incremental kind of like slowly growing and...
Slow and steady. Slow and steady. Immigrant mentality, man. Hard work. I get my work ethic from my immigrant parents. Both of them are immigrants.
From where?
China and UK.
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Chapter 8: What are Oleg's future goals for his pillow business?
Nice. Yeah, but the China, oh my God, they work hard. Those Chinese people.
Well, I'm such a mix too. I'm a Russian born... Half Jewish, half Korean. Holy crap, you're Korean? Yeah. My father is Korean. I'm Oleg Lee. My last name is Lee. Oh, wow.
I would have never guessed that.
I was born in Russia, raised in Israel. I live here.
You like America the best? Yes, of course. Not close, right? No.
Also, I have three kids now. That's why I love where my kids are, you know?
Yeah. I always thought it was weird that people complained about America.
I travel Europe a lot lately. Definitely love a lot about Europe, the culture, the food and everything. But opportunities in America, you can't compare. I can see myself living in Europe, but I can't make money in Europe. Here you can. That's the biggest thing about America.
You'd be limited in Europe. You can't walk in a bank and get a $50,000 credit card.
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