In short
Episode topic: How Oleg Lee built a $20M/year e-commerce empire by selling custom, dog-shaped pillows—starting from a grief-driven prototype, validating demand via social media and Groupon, scaling through Meta ads, and later adding custom photo ordering plus wholesale/brand licensing.
Guest backgrounds
Oleg Lee (“the pillow guy”) runs the business behind custom-shaped pillows; he started as a side hustle while working construction. His father worked in a print shop and helped manufacture the first pillow in the garage.
Key claims
The “viral” origin was posting a lifelike dog-shaped pillow (Izzy). Groupon and Walmart proved demand, but low margins pushed him to DTC/B2C. A $100K mock-up generator improved conversions. Meta works via massive ad testing and shareable UGC reactions. Celebrity/brand deals came largely through direct DMs.
Notable examples
Izzy pillow origin; Groupon sold ~20,000+ pillows; Walmart vendor deal (~200 stores); DTC custom photo ordering with 360° preview; viral ad example of an 8-second “college girl” unboxing; David Dobrik world-record collaboration; Netflix/Paramount merchandising pillow supply (low-margin, growing with new shows).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Pillow Origin Story
0:00 to 0:45
Learn about the unique origin of a viral pillow business inspired by a beloved dog.
“A guy posts a photo of a pillow on the floor.”
From Loss to Business
1:01 to 2:25
Oleg shares how he transformed his grief into a thriving pillow business.
“Let's go back to your origin story, though.”
Going Viral on Social Media
2:25 to 3:10
Discussion of how Oleg's pillow gained traction online and the initial reactions.
“I want to talk about actually posting it on the internet.”
Groupon Success and Challenges
3:10 to 4:19
Oleg details the unexpected success of their Groupon campaign and the challenges faced.
“And it was like French bottle, golden retriever and all the other bits.”
Scaling Production from Garage to Walmart
4:19 to 5:35
The transition from fulfilling orders in a garage to scaling production for Walmart.
“But like you look in the number, like you understand, first of all, you're going to get this money.”
Navigating the Walmart Experience
5:35 to 7:43
Oleg discusses his experiences and challenges working with Walmart as a vendor.
“And And then we realized, okay, so we went and started offering the same pillows to everyone.”
Transitioning from Wholesale to DTC
7:43 to 8:50
The strategic shift from wholesale to direct-to-consumer sales and its implications.
“I was a carpenter, so I did a lot of woodwork.”
The Direct-to-Consumer Shift
9:30 to 12:23
Oleg explains the key characteristics of transitioning to a DTC model and its advantages.
“What were some of those key characteristics early on for you?”
Building a Lean Team for Growth
12:23 to 13:27
Insights into managing a small, efficient team while scaling a business.
“We probably went from being$5 million to$10 million in revenue within a little bit over a year.”
Marketing Strategies for Success
13:27 to 14:00
Oleg shares effective marketing strategies, particularly for Meta platforms.
“We went from 10 people to 50 people now on the warehouse.”
Show all 15 chapters
Meta Campaign Strategies
14:00 to 16:42
Learn how to effectively launch and analyze meta ad campaigns.
“So let's say we throw 150 ads in only like 10 over.”
User-Generated Content and Reactions
16:42 to 19:17
Discover the importance of user-generated content in successful ads.
“when I've like sold like B2B marketers, I always have, I'm like, oh, like B2B marketer to get like super specific.”
Celebrity Collaborations for Brand Awareness
19:17 to 21:28
Understand how to leverage celebrity partnerships for brand visibility.
“Because at the end of the day, I am the only manufacturer in the USA who makes this product.”
DMing for Partnerships and Opportunities
21:28 to 23:24
Learn the art of reaching out to celebrities and brands via DMs.
“There's a bigger company, bigger than them, who owns all their merchandising.”
The Importance of Mindset in Entrepreneurship
23:24 to 25:41
Explore how mindset affects entrepreneurial success and resilience.
“So I'm intentionally abusing myself, putting myself in the like mental, physical challenges.”
Transcript
Automatic transcript. May contain errors.0:00Oleg Lee:Picture this. A guy posts a photo of a pillow on the floor. The internet loses its mind. The pillow looked exactly like his dog. Not a picture printed on a square, but custom cut out in this exact shape of the animal. The dog's name was Izzy. She had just passed away. Oleg asked his dad to make it. Dad did. Oleg posted it and people immediately wanted to buy one. That was the entire origin of the business. Fast forward to today, 400 ,000 custom pillows a year, 20 million in revenue, half a million a month in ad spent, and he's the silent manufacturer behind Netflix Shop, Paramount, and Chewy. And he ran out of his dad's garage as a side hustle for 10 years while working construction full-time.
0:45Oleg Lee:I'm Ryan Atkinson, and you're listening to Help Flip Podcast, where we interview entrepreneurs to hear their advice, how you can start a business too. And today, I am so excited for this interview. This is such a unique topic and such a unique story. So I'm excited to welcome Oleg Lee to the podcast. Oleg, thank you so, so much for being here. Hey, Ryan, thanks for having me. Let's go back to your origin story, though. Your dad was in a print shop making generic pillows when your dog Izzy died. And you asked him to make something different. Talk to us about that pillow and like the origin story and what happened when you posted it.
1:14So yeah, I lost my childhood dog. And you know, I miss him so much. And to make it long story short, I asked my father because I saw him when I visited him at this factory, the printing shop, I see him making pillows and ask him can you make me a pillow so he made a pillow with a picture the square pillow but it was kind of cool but it was a little bit boring yeah I could hold in the dog but like it wasn't the same so I asked him can you actually cut out the whole shape of the dog and make it into a pillow so he's like yeah I think I can do it I mean shouldn't be a big deal so he made it I came back I looked at the pillow and like I almost cried I'm like oh my god this is like my dog is just sitting there I took a picture posted online and internet lost it as you said everybody's like oh my god this is so cool this is so lifelike this looks like a real dog can i get one so i'm like i guess i think we're on something there's so many requests but the problem was we're not able to offer a custom pillow because it was we didn't know how to take orders so we went and we purchased i'm jumping a little bit forward but we basically start selling we went and we found what are the top most popular breeds in the usa and we found them and we bought pictures of 10 most popular breeds and started making them to shape pillows and selling them.
2:21That's how it basically kind of started first.
2:24Oleg Lee:Oh, man, that is so cool. I want to talk about actually posting it on the internet. Where did you post it? Like, what was like that initial reaction? Again, was it people like, Oh, my gosh, I want one, I need one? Or like, where'd you post it? What was that initial reaction? Yeah, it was on my social media on my old Facebook. And then the feedback was basically, Oh, my God, this is so lifelike. It looks like a real dog. I want one. How can I get one? And it's just hundreds of comments. And we're like, what did you get? I'm like, well we made it we didn't get anywhere and actually started looking there's nobody was offering it wasn't it didn't exist and yeah that was how idea came out like we should probably make it you know and start selling it so you're printing off now the top 10 dog breeds instead of doing custom orders initially what happens then i mean you got popular dog breeds what happens then so we opened a little website we put the pillows there and then the biggest thing what happened we group on was training back then and i know if people familiar with group and it's kind of old now but we went to group on i knew someone to someone to someone and i said hey i have this cool product because i knew people want it right so i can offer you a limited quantity and the star breeds for this price they love the idea again it's a new product didn't exist they launched it we knew we're going to sell like few hundreds we sold 20 000 20 000 of this pillows I think like the fog was the top sell.
3:48I think it was 8 ,000 on F fog. And it was like French bottle, golden retriever and all the other bits. And I was like, okay, how do we make them?
3:56Oleg Lee:Oh, man. How do we make and ship? We didn't have any infrastructure. We didn't have any office. We had nothing. So me, my father in his car garage, we started making them one by one by the prints from the factory that he worked, bring them into garage and we sold them and stopped them and closed them and shipped them. my entire family was involved all the relatives everybody's stuffing by hand it was a nightmare but that's how we knew the demand is there what were you feeling at this time because i'm trying to put myself in your shoes you're like okay let me just test this out boom all of a sudden you have 20 000 orders was this life-changing moment or did you know it come it was definitely life-changing moment because it's like first of all you don't see just sales you see the money the amount of money also i don't remember how much it was it was a few hundred thousand dollars i think i think it was maybe$300 ,000 or something.
4:43I don't remember the number. But like you look in the number, like you understand, first of all, you're going to get this money. That's a lot of money right now. But the problem was, until we get this money, we have to fulfill the orders and make them. That was kind of a tough moment. And that was insane experience. We definitely didn't expect we woke up to this. And it didn't go for a day, it went for three days. So first, it was like, 8 ,000. And then like 9 ,000, then 1000. And then just shit, they keep going and keep going. It ended up, I think 22 ,000 pillows or something.
5:09Oleg Lee:Oh, my gosh, that's insane. So you guys were doing this just out of your garage, you and your dad are like doing these custom paint that picture for us. I'm curious, what does that look like? Because that has to not be easy or scalable. I wish we recorded that, you know, how we were doing it in his car garage, the entire family, like maybe 10 people standing and stuffing pillows and packing them. It was a crazy experience. It was, you know, people say it's a good problem to have, it's still a problem. So they need to figure out how to make them and ship them. It wasn't an easy thing to execute.
5:37But we got it done. And And then we realized, okay, so we went and started offering the same pillows to everyone. So I basically flew to Walmart corporate offices and I said, hey, I have this product that sold X amount in Groupon and I can make unlimited quantities, buy from me. And I ended up getting a deal. We basically were in 2000 Walmart stores nationwide. And that's where we started expanding, buying equipment, because we basically got in, we became Walmart vendor. And then they, I think four or five months later, they placed the order. And the order was like the place in order in September and you have to deliver it in like an October, they only give you one month, which was also another nightmare to execute it.
6:15Oleg Lee:Oh yeah. Interesting. So I want to ask about the Groupon Walmart timeline here. How quickly did all of this happen? Was this in the span of six months? No, no, I think it was a year later when we executed the order. We rented the little place. We got a little bit of equipment cause we realized, okay, people want this product. We went to Groupon, we did another event later on and we sold another like a few thousand. I think it was five thousand the second time. And then we start offering it to like Amazon and Overstock and all these marketplaces. And then I started chasing Walmart. I watched the Ark thing.
6:50I'm like, okay, I got to get into the stores. It was great. Walmart experience was good. Walked away from that deal to get into nationwide because the expansion required a lot of investment and it's not guaranteed I'm going to continue buying it from you. So it was risky and I made a decision not to do it anymore.
7:08Oleg Lee:At this point, are you doing it full time? I know you're also working construction gigs. So talk to me, what was your personal life like around this time from a year into it? I was still doing construction because the problem with all these marketplaces and Walmart specifically, the OPA 60, 90 days. Walmart, I think it's 180 days. So you have the orders, you have the sales, you have the cash to fulfill the orders, to buy the materials, to ship them. So I had to have the money to go work and get cash so I can pay. Because we're sitting on tons of receivables all the time. That's why I had to keep working.
7:42I didn't do a lot of work, but it looked like I would paint a house at night on the weekend or do some floor. I was a carpenter, so I did a lot of woodwork.
7:50Oleg Lee:Okay, so then talk to us about walking away from Walmart. Because it looks here like you went from 200 stores to like 2 ,000 stores, which is incredible. But why did you ultimately decide to walk away from Walmart? To be honest, the Walmart order, we probably lost money on it because the margin is small. The timeline, they give you only one month to create the order from the pickup day. The pickup day all at once. So we had like maybe 40 pallets or something of pickup. They have to be ready at one day. We didn't have a space to stock it. So we're stuffing boxes to the roof. And then when the rocks start coming in for pickups, we have to palletize them.
8:27It was a lot of work, a lot of hours. We have to hire so many people to execute it. Very small margin because it's, let's say, it costs us$5. We sell them for like$7.
8:37Oleg Lee:Oh, wow. The margin is very small. And also, we start pushing more custom to the website where the margin is insane, right? From$5 cost to$50 retail. So I'm like, I want to do more of this. I don't want to deal with Walmart or this. I don't want to deal with this anymore. So it was a transition going more B2C and moving away from all the wholesale idea. Are you ready to launch, grow and scale a business? Inside the Uplip Academy, you'll get a complete roadmap to shortcut your success with 25 plus step by step programs taught by active business owners, not gurus who share their step by step blueprints, plus ongoing live workshops, skills training, a business idea database and community to share resources and celebrate your wins.
9:21Oleg Lee:Click the link in the description below to join the Elphab Academy today and start surrounding yourself with the people and tools that can change everything for your business. Talk to me about that shift from DTC. What were some of those key characteristics early on for you? Was it going from$5 to$50? Why was DTC the no-brainer play for you? Well, DTC is much harder as far as you need to spend a lot of money on marketing. We didn't have the money to spend on marketing, but once we started getting into proper cash flow, and we could put some money into the marketing, into the ad spend, this is where we're actually able to allow the transition.
9:55Because now when you sell directly, you get paid the same day. Actually, it's next day from Shopify, right? So the money started coming in daily. The cash flow improved. Now like, okay, we don't need wholesale anymore. We don't want to sit on the receivables. It takes so many more people to execute, so much more work and so much more risk. We got screwed by some of these sellers. They didn't pay us. My Touch of Modern was one of them. We used to sell, then they went out of business and they didn't pay us I don't know how much money. It was another one. I don't remember the name. So more risk. And we basically at some point, I made a decision, transition fully to B2C and walk away from all the wholesale.
10:28Oleg Lee:So you guys are doing custom orders now. Talk to me about the equipment that your team needed for that. Was it a seamless transition to starting to do more custom work or what pivot was needed for your team? So to do the custom pillows, as far as making the product, it's the same process. Print, cut, sew, stuff, all this stuff. It doesn't change the process on the manufacturing. It's the front end. It's how to receive your photo, understand what you want, crop it, size it. So first, if you would go to our website in the beginning, you have to upload your photo place in order and trust us to do the work.
11:01And most people, they don't trust it. Like, I don't know what I'm getting. And when we realize the issue, we spend a year, probably over$100 ,000 on developing our own tool, which is the mock-up generator. For example, right now, if you go onto my website, you take a photo at the moment and you upload it it will instantly crop the person or the pad will turn into 3d spinnable pill you can see it all you know 360 that's cool so you see exactly what you're getting and our team is trained to sell the pill based on mock-ups if you compare the actual pill that you're going to receive and the mock-up you saw is going to be like 95 accurate so once we launch this tool that's changed the game completely because now the conversion increases crazy i feel like the conversion rates
11:43Oleg Lee:I don't know what they were, obviously, but would have to just absolutely skyrocket. Because I feel like it's one of those things where someone now, they get to visualize it. It's like more real than just a photo. I feel like that had to be so big for your guys' conversion rates there. That was a game changer. And we also made sure that it shows you the preview in like three seconds. Super fast. Because most custom websites, you go, you upload, it takes forever. A lot of steps. We made it simple. Drop a photo, see your pillow, place an order. That's it. Do you have like any conversion metrics off the top of your head?
12:12Oleg Lee:How it jumped? Honestly, it's not as much as... I don't remember the conversion, but business started growing. The revenue started growing crazy from that moment. So it's safe to say that$100 or$100K software probably paid off for it pretty quick. We probably went from being$5 million to$10 million in revenue within a little bit over a year. So when you guys were doing like 5 million revenue, kind of paint us the picture of like what your team looked like, like who was on the team, who was there? Because I think it's a super interesting source, a super niche market, which I just absolutely love.
12:45Oleg Lee:What did like that team look like when it was at like 5 million? Honestly, the team was pretty small. We had one guy who in our entire marketing, paid ads, email, Google, everything marketing related. We had one graphic designer in-house. we had me i mean doing a lot of marketing as well and helping with content and stuff and that's it pretty much that was very very small thing like three people but even now we're like we're only like five people team so crazy we're very small because it's like you know to scale it doesn't really require more effort we just basically spend more money on marketing and that's it so basically where we do need more hands and people it's in the manufacturing side this is where we're going.
13:27We went from 10 people to 50 people now on the warehouse.
13:31Oleg Lee:Well, let's talk about the marketing side. And if someone is listening, if they want to do a similar business, how they can grow as well. So you just said, spend more money, you make more money. That's a common business notion there. What are you guys spending money on? And what is your monthly spend on marketing tasks? Well, we spend mostly on Meta, which is Facebook and Instagram ads. We spend a little bit on TikTok. On average, we spend about half a million a month like obviously november december we spend over a million a month but i would say from half a million and 80 goes to meta spend we on any given date you go to our meta account or go to it as library we run over thousand ads every day we launch hundreds of ads every week so it that's kind of like i wouldn't say it's a secret but that's how you're supposed to do it you have to launch a lot of it so you can't just spend more money like i wish i could spend a million every eight months or two million like there's no limit to the budget as long as the return is right you know talk to us about obviously i don't think of this the total secret sauce of everything you're doing but give us some of the secret sauce of like successful like meta campaigns because i'm personally like starting to learn like meta campaigns for like a very high ticket item like oh should i do meta should i do linkedin give me some like meta tips here like what goes into a successful campaign and like how do you know something is successful in that obviously pretty simplistic.
14:51Well, it's a lot of testing. So let's say we throw 150 ads in only like 10 over. So we're going to remove the 140 in place and with another 150 ads. So like you have to really do big batches of ads to understand what's working. Then you have to analyze what's working and why it's working. But with meta, I mean, probably anyone will tell you always the random stuff does the best. Like I personally used to edit and create ads. And one point I was creating batches for Christmas. And I like I take a long minute video and I chop it into five clips. But then I had some videos that I couldn't do more than one clip out of this video.
15:27So I saved them as a solo. I was just like, Okay, I don't care about this. I just saved them in this folder, I called them solo. And one of them being our highest would probably spend 2 million on this ad.
15:37Oleg Lee:No way. Eight second ad. There's a college girl in the college room, in the door room, very bad quality. she opens the package and she cries immediately and she hugs it. We have tons of similar videos, but this one, I don't know why. It just stuck with people and it made us a lot of money. So with ads, you never know. There's some you think, okay, it's going to be great ad. Nah. You really have to be just throwing and testing, throwing and testing. But what makes successful ad is shareable ad. You know how we all send each other reels and stuff? You don't think about it. Like if you know I'm a passionate runner and like you see something about running, you immediately think, oh, Oleg, I'm going to send him this.
16:20You don't even think, it's just instant. This is how the ad's supposed to be as well. When somebody sees it, you don't want them to think of someone. You want them to exactly know who they're going to send it to. And if you can achieve it through the ad, you have a winning ad, basically.
16:34Oleg Lee:Everyone should rewind that and hear that 500K a month strategy right there. That's a great breakdown. Is there a formula though that like works for you? Like, because in my experience, when I've like sold like B2B marketers, I always have, I'm like, oh, like B2B marketer to get like super specific. And I get into like an offer, like right away. And like, we saw all right results. We should have honestly tested more, but like formula that works consistently for you. Is there one? Well, we have a lot of you juicy reactions. So like we basically encourage people. Most of our product purchase as a gift to someone.
17:03We know that we collected this data. We know it. Now, every time somebody purchase was telling, hey, we know you're gifting. make sure to record your gifting moment send it to us we'll give you 250 store credit if it's good and we have 2500 videos like that we get like five to ten videos every single day people submitting because we give a lot of credit but then one of them will win and it's amazing so for us the basically the reactions the true reaction when i'm giving you a package it's closed it's sealed you open it in front of the camera like you don't even know i'm filming you i'm just gifted i gifted you you open it pull the pillow first reaction they always hug it most people cry because it's very emotional like it's either they somebody they love or miss you know and those are the best ads you know the true ugc reactions so you have like the true ugc videos but
17:55Oleg Lee:like you have done some really cool stuff with celebrities i'm looking at your instagram here tell us about the david dobrik one that i'm seeing here on your instagram as well tell me about that We did a lot of collaboration with celebrities. It's mostly for product and brand awareness. I can't say it drove a lot of revenue, but definitely people are like, oh, I've seen this on David Dobrik. So here and there. With David Dobrik, he's local. He actually went to high school where effective is, Vernon Hills, Illinois. So that's basically where we did the world record was in front of his high school.
18:24And he lived there in the area. So we're looking to partner up with somebody big to do the world record. And we figure out, okay, David Dobrik is a great candidate because he's local. You know, he has a lot of local community. And we knew someone who knew him and we reached out. He agreed to do it. We did this together.
18:40Oleg Lee:It was fun. Good experience. It's really interesting, though, that you say like celebrities, like it's great for brand awareness, but it might not be for revenue. I'd be curious, like, what are some like thoughts on that? Because like, I would think like if you did something with David Dobrik, you'd be like, oh, my gosh, like, this is so cool. Like, I'm going to go on the landing page and like buy one. Like, what's kind of the theory behind that? Most of the celebrities pillage, you can sell them, first of all. Right? So like if I'm making pillows for Pater's Hilton, which she's a good friend and I always make pillows for her, I just send her a bunch of pillows for her Coachella party.
19:11I can't really sell her pillows. So me giving her pillows and making for her own sheets, posting and tagging, just bring awareness to the product. Because at the end of the day, I am the only manufacturer in the USA who makes this product. So if you see this product anywhere in the USA, in any party, in any place, you always come back to me. Who makes it? You started searching, you started Google and you're going to find me or my brand. So that's why I'm putting my product into places and houses and hands of every celebrity. So we made for Kim Kardashian, birthday party, her own birthday, you name it, for DGKL, like we work with a lot of celebrities, but it's never like you get a lot of attention, not real orders, but maybe the order is coming in later.
19:50It's basically the trust factor that we legit.
19:53Oleg Lee:Oh, for sure. It's a new brand. You're trying to grow it and like, can I trust these people? And then when you see, you know, all our celebrities, like, yeah, I can probably trust these people. Yeah. Well, I feel like it's just straight social proof at that point. Because when I'm thinking about like evaluating, you know, buying something that I've never bought before, if I see, you know, Paris Hilton on there, David Dobrik, someone famous, I feel like it just adds that social proof. And that probably makes your ad better, essentially. Well, we don't use any of this creative in ads, but on our website, yes, it is a social proof.
20:23It is credibility. We still kind of small brand that trying to grow. So like at some point, maybe we won't need it. Our name will be big enough and known enough. But for now, it's very, very important. And it's actually good how people should be doing it. You know, I took the strategy from Damon Jones from Shark Tank. That's how he did Fubo brand. He put his shorts and hats on all the celebrities. That's how I build credibility. You know, you can say all day your product is great. But at the end of the day, I want to see somebody I know, you know, using that product.
20:49Oleg Lee:Speaking of somebody we all know, that is Netflix, Chewy, Paramount, etc. And you are the back-end manufacturer for all of them. How did those deals come together and how those partnerships start? So this is my biggest secret sauce is my Instagram. I utilize it to the full. And that's something I learned from Gary V, by the way, Gary Vaynerchuk. He said, just DM people, DM people. And I really started doing it. So the Netflix and Paramount, it's all to DM. No way. Yes. All the celebrities, all my relationship, it's all to DMs. I worked with some of the largest brands. I just DM them, email like, I don't want to say names, but the Netflix, we don't work directly with Netflix in Paramount.
Read the full transcript
21:30There's a bigger company, bigger than them, who owns all their merchandising. And I was looking to work with the biggest name. So I reached out to them. They responded to me. Took a year of communication. We signed an agreement. And now basically, any character that exists out there, we make the pillars, basically.
21:46Oleg Lee:No way. Are you able to share what does that mean in terms of revenue for your team? so again it's a wholesale price because it's a lower margin hey i think in the first year we did a little bit over two million with them it's growing and it's significantly growing because they keep adding more new shows like stranger things the k-pop demon show if you go there's pills now the squid games so all the shows you know and the more they're going to add pills to the shows the more business we're getting but again it's a low margin but it's good for credibility again are you able to share like what goes into that dm are you just like asking to work together or like what's typically like a good DM to land in a celebrity's inbox?
22:24For celebrities, usually I will make the pill and I'll DM and say, hey, I made this for you. And usually it's our research. So like DJ Khaled, for example, it's a good example because I made pill of his, I knew how much he loves his son. I see his stories. So I'm making pill of his son. I'm like, hey, check this out. I made this for you. Now he sees something of his son. He can say, I don't want that. It's already like personal to him. It's like, oh my God, send this to me. Right. and then he followed me and sent him a bunch of more pillows. So celebrities, this is how I do. I make the product, I DM them with the product, say, hey, I just made it for you.
22:53Let me know where you want me to send it to. For companies like this, I reach out with something like, would love to be considered to be your pillow supplier because I know they don't have the product. Custom-shaped pillow supplier. Shout out to OnlyFans, you know, we start working with the de-order pillows from us. Not for creators, for the branded pillows and a lot of other big brands. We're just like, it's a simple DM. Hey, just consider me to be a supplier. I'm like, that's what we do. and once they do the research they know it's basically no one else is doing it and they'll come back to us some try to go to china and then they end up coming back to us
23:24Oleg Lee:there you go i want to ask about your mindset as well as we close down this podcast talking about your mindset you're a humongous runner you have a goal to run a marathon in every state talk to me about mindset and like the importance of that plays in your entrepreneurial story i think it's looking back now i think that's one of the most important things everything stems from your mindset and a mind is basically where your body is that's where your mind is so I'm intentionally you know I would say abusing my body so my mind is stronger because you know when you're on a marathon and it's mile 20 and you're on breaking point you're like you want to cry you want to quit but you cross the finish line you feel like so pumped and accomplished then you go to office and they come to you like oh my god oh like there's a printer that broke I'm like that's it I just suffered for four hours you tell me printer broke just buy a new one you know everything becomes so like you become like stress proof so I'm intentionally doing it because it makes me a stronger leader, better father, better husband.
24:17You know, I don't overreact on stuff. So I'm intentionally abusing myself, putting myself in the like mental, physical challenges. So when I go back to my life the next day, nothing can stress me out. And it's been working. And I ran 27 marathons, you know, and that's the reason why I keep doing it. People think, you know, I enjoy it. It's not always fun. It's not always easy,
24:40Oleg Lee:but that's exactly why I'm doing it because it's hard. Interesting. I feel like for me, mindset, it's like, it's so much when it comes to entrepreneurship, because like, as you 100 % know, like, there are the amount of times you get punched in the face as an entrepreneur, as you try to grow a brand, like every day, you can get punched in the face, essentially. But like, you can always go back to like going through hard things. I'm sure that's true to your story of like, all the marathons you've ran as well there. I think it's very important to start there. Because a lot of entrepreneurs only focus on business side and in completely neglect, they sleep, they exercise, they body, they mind.
25:11That's a key. When you get enough sleep, you wake up fresh, your body in a good place, you go for a run, you get your blood flow going, and then you do your work, it's completely different when you just sit all day on a computer and you do nothing. When I saw these changes actually helping my business and everything for me to grow, I didn't want to stop anymore. I've been on a running streak for six years. I haven't skipped a day. And there's a reason behind it because the discipline is the most important.
25:39Oleg Lee:I love it. The discipline is the most important. Last question before we get into our Fan Blitz question. What is your average marathon pace here then if you're doing 26, 27 marathons? My average marathon pace probably 320. That's good. That's pretty solid. Yeah, my fastest is 255. Between 320, 330, that's my like easy finish time. Usually if I push a little, it's like 315. I don't really push. I enjoy every race. You know, I try to explore, watch it, but you know, end of the amount when you still feel it. Well, I have enjoyed this podcast. This has been so good. Let's jump into our fan blitz questions.
26:13Oleg Lee:And listeners, if you want to join in on world-class entrepreneurs that are doing 20 million plus in revenue, email us at podcast.upflip.com. We'll get all your questions answered there. But ready for our last five questions here? Yeah, let's do it. Do you have an Izzy Hello in your house right now still? Yes, it's in my living room. I like it. What's a product you've seen and thought, I wish I made that? Never thought about it. best business advice your dad ever gave you unfortunately my dad was an entrepreneur so he learned a lot from me he was a hard working man all his life you know yeah something to learn from there as well last one if you ever had to start over tomorrow with a thousand dollars and no factory what would be your first move invest in myself i like it amazing podcast here thank you so much for joining us if someone's like oh my gosh i need to learn more about you and connect with your what's your Instagram, what's your website, drop it all for us.
27:08Yeah, you can find me anywhere that pillow guy on the TikTok, Instagram, LinkedIn, Facebook, anywhere. And my website, you can go to the pillow guy.com is going to redirect you to my actual brand, which is all about vibe.com. This is the website.
27:22Oleg Lee:Everyone, that was an amazing episode with Oleg three quick takeaways for you. If you guys are going to have meta be your main strategy, shareable ads are key make something so automatic that you're going to want to share it with a friend. Number two, if you're trying to get celebrity endorsements or celebrities to use your product, send them a DM saying, hey, I built something for you. Check it out. Get it in their hands. That's one way to do it. The number three, we ended talking about mindset. Mindset is truly everything for him. And he talked about running 26, 27 marathons is just like mind blowing to think about.
27:54Oleg Lee:Think about that. Build toughness. Entrepreneurs need to be tough. And he is one tough dude. Phenomenal episode here. If you guys enjoy this podcast, please give us a five-star rating wherever you get your podcasts. It helps us get more amazing$20 million a year CEOs onto the show. We will see you next Monday. Well, thank you so much for your time today. Great conversation. Thank you for the opportunity. Yeah. Thank you for having me.
From the publisher
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.
The $500K/Month Meta Ad Strategy: How to aggressively test batches of 150+ ads at a time, and why raw, authentic UGC (like an 8-second clip of a crying college student) outperforms highly edited marketing videos.
The "GaryVee" DM Method: Oleg’s step-by-step formula for sliding into the DMs of A-list celebrities and massive corporations to secure lucrative wholesale deals and priceless social proof.
Marathons & Mindset: Why Oleg intentionally puts himself through the physical torture of running a marathon in every state to build the mental resilience needed to handle $20M CEO problems.
Tags: E-commerce, Retail Goods, Digital marketing, Business growth, Facebook Ads, Online Business
Resources:
Grow your business today: https://links.upflip.com/the-business-startup-and-growth-blueprint-podcast
Follow Our Second Channel Here: https://next.upflip.com/spotify
Connect with Oleg: https://www.instagram.com/allaboutvibe/?hl=en




