How Proud Zebra Started: From Singapore to Canada

TL;DR: We're Delwin and Jimmy, the two people behind Proud Zebra, a queer-owned Canadian brand designing LGBTQ+ pride pins and accessories for 35+ identities. We met in the Singapore army, moved to Canada in 2021 with four suitcases and a cargo container of enamel pins, and built this business from our apartment. We've shipped to 5,000+ customers worldwide, work with 60+ wholesale accounts including HarperCollins and TJX, and have donated over $10,000 to LGBTQ+ organizations. This is the long version of how we got here.

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How Did We Meet? Behind a Tank in the Singapore Army

We met behind a Bionix, an armoured vehicle in the Singapore army. We were both commanders in Armour. Exchanged numbers for work reasons and didn't think much of it. Connected on social media. Five years went by without much communication.

At the time, I (Delwin) had a girlfriend. I hadn't truly accepted myself yet.

Then we both ended up single in New York at the same time. I reached out to ask for his itinerary, but really, I just wanted to flirt. We never actually met up in New York, but we texted so much I had to apologize to the friend I was travelling with. Meanwhile I'm sending selfies of me licking a strawberry in my hotel room trying to get a reaction, and getting absolutely nothing back.

I literally ghosted him because I thought he wasn't interested. He followed up and I told him I didn't feel like he was into me. Turns out he was. He just showed it by researching a Yayoi Kusama exhibition and sending me the link. That was Jimmy saying he cared. We went to see it on our third date back in Singapore.

Back in Singapore, I picked him up at Bishan MRT for our first date. He was waiting along the side of the road. Freshly dyed black hair, because I'd casually mentioned I liked black hair. Didn't say a word about it. That's the thing about Jimmy.

100% Actions. 0% Words of Affirmation.

His love language isn't words. Quality time and acts of service. Mine is physical touch and words of affirmation. Yeah, you can imagine how challenging that first year was.

Six Dates and a Toy Story Card

Our first dates were great. Building an actual relationship after that? Brutal.

I spent an entire year asking Jimmy to just hug me for five minutes. His idea of affection was researching an art exhibition and sending a link. Mine was designing a Toy Story card in Photoshop with our selfies from every date.

We'd been on exactly six dates. I was doing army reservist, that two-week in-camp training every Singaporean guy has to do as part of their conscript army commitment. I booked out on Saturday with one mission.

Rushed home. Opened Photoshop. Designed the card. Toy Story themed because I knew Jimmy loved Toy Story. Put our selfies from every date on it. Drove to a local print shop to get it printed because I didn't own a printer. Hid it behind the passenger seat of my parents' car.

That night we drove to Bishan Park. We were playing Mobile Legends in the back seat. My hands were shaking so badly I couldn't even play the game properly. After the match, I suggested we play a game where we each give compliments back and forth. Then I asked him to check behind the seat. He found the card. He opened it. Read it in shock and awe. I asked him to be my boyfriend.

He said yes. That was 2017.

Some things start with a printed card and shaky hands. And then they become your whole life.

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Why I Quit the Career I Trained My Whole Life For

I left Singapore at 10, grew up in Canada from 10 to 20, then moved back to Singapore for mandatory two-year army conscription, university, and work.

And everyone laughed at me.

I didn't speak Singlish. I barely spoke Chinese. I sounded Canadian, which was apparently unacceptable to everyone I met in Singapore. Full-on bullying over the way I talked, in the country I was born in.

Weekends in army were the worst. Everyone else would book out and hang with their friends. I had nobody. My family was abroad, my girlfriend in Canada ended the relationship due to long distance, and I had zero friends. I recall crying on some weekends because I felt so lonely and miserable.

Not Singaporean enough in Singapore, not Canadian enough in Canada, not out enough to be fully myself.

It took four or five years to actually feel like I fit in. And it only really clicked after I met Jimmy and started hanging out with his friends. I'm inquisitive by nature so I'd constantly ask people around me what things meant, no matter how much sarcasm and side-eye I got. Jimmy and his friends taught me how to belong.

I did a master's in architecture on a scholarship. They paid for university, and I had to work at the firm for three years after. I lasted two. The nights went till 1-2am on the bad ones, and 7-8pm on a good day. I'd show up the next morning in a daze. Weekends were just recovery. Sleeping for hours, dreading Monday. I was literally having nightmares about work. My brain wouldn't shut off.

I started calling in sick because I just couldn't do it mentally. I needed days where I didn't have to perform being okay.

One night in a hotel room in Vietnam, I was drinking liquor and building a presentation due in six hours. My colleague was right beside me doing the same thing.

That was the night I knew I was done.

I quit and paid off the remaining bond with money I didn't really have. I wanted to do something on my own. I wanted to push my own boundaries. And I really wanted to learn.

How I Designed 200+ Pride Pins Before Selling a Single One

When I started Proud Zebra, I genuinely thought the hard part was designing. I have a master's in architecture. I know Illustrator, Photoshop, the whole Adobe suite. So I went all in.

I designed the entire Proud Cubes collection. Nine designs per identity, inspired by my love for geometric and architectural forms. Over 30 identities. That's 200+ pin designs before I'd even written a single listing. My ADHD brain was in full hyperfixation mode and I needed to get this right.

Nobody found them. I had zero knowledge of marketing. I didn't know what SEO was when I started. I messed up our Etsy listings so badly it's genuinely easier to start a brand new shop than fix it.

But I kept adding identities. Aromantic. Demigirl. Demiboy. Aroace. When you've spent your life being a version of something nobody acknowledged, you don't leave anyone out. If an identity exists, we do our best to represent it.

Here's the lesson that actually changed how I think about everything: marketing isn't optional. Marketing IS the business. You can have the best product in the world, but if nobody knows it exists, it doesn't matter. Your story is your brand. How you tell it is what makes people actually care. That lesson hit so hard it literally changed my career path. I now work full-time in marketing, and Proud Zebra taught me the story matters more than the product.

The very first pins I designed were charity pins. Not meant to make money. Home for Everyone (inspired by AKT, a UK charity supporting LGBTQ+ youth homelessness), Two Spirit Feather Dancers, and the SG Rainbow Scorecard lapel pin. Charity at the core from day one.

At first the plan was to donate a portion of profits. But we noticed that wasn't really enough. This business is for the community. That's why we decided 100% of net proceeds from our charity pins go directly to the related charity. We've now donated over $10,000 to LGBTQ+ organizations.

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How We Decided to Move Countries Over Six Drinks

Holland Village, Singapore. A random weekday night, way too many drinks. This was still early dating, maybe date four or five. I recall really wanting to kiss him after because we were tipsy, but I chickened out and it didn't happen.

We got onto the topic of the future. Where we saw ourselves. Where we wanted to end up. I talked about how I'd always planned to move back to Canada. How Singapore never really felt like home after spending my formative years abroad.

Jimmy had already always wanted to move overseas. He'd tried applying for jobs abroad multiple times but it wasn't easy. So once again, our stars seemed aligned and a glimpse of our futures looked brighter together.

Six hours we sat there. We talked about past relationships, jobs, immigration, timelines, what we'd pack, whether we'd miss Singapore. Neither of us was drunk enough to call it crazy. We just knew.

We gave ourselves five years. It took us four. Because we were realistic about what it would take. Save up. Finish our commitments in Singapore. Plan the logistics. But the decision was made that night. Everything forward was just execution.

We talked about getting married, having children, and even a cute little puppy. But we knew none of that could happen in a country that still denies LGBTQ+ couples the right to marry. So in December 2021, we left behind friends and family and moved our entire lives to Canada.

Two guys, six drinks in, a conversation that changed our whole lives.

How I 3D-Modelled Our Entire Life Into a Shipping Container

When we decided to move, we packed like we were never coming back. Because that was the plan.

We rented an 8x8x10ft cargo cube. I measured every single box. Because I have a master's in architecture and can't stop 3D modelling things, I built a digital model of the cube and placed every box inside it like Tetris. I even cleared a section of my parents' living room that matched the cube's exact footprint. When the real cube arrived, we packed it exactly like the model. Every inch used. Not a single gap.

$4,000, stuffed with our clothes, Jimmy's LEGO, and a few hundred enamel pins for a business we barely knew how to run.

The delivery guy said he'd never seen anyone pack a shipping cube that tightly before.

We Crossed the Canadian Border on Foot in Winter

December 2021. We flew from Singapore to Seattle with a layover in Hong Kong. Twenty-five-plus hours of travel. Four suitcases between us. Two each, 23 kilos, stuffed with everything we'd need to start over.

From Seattle we took a bus to the border. Then we got off and walked. Up the slope toward the US-Canada crossing in the dark and cold. We thought how stupid we were to start our lives abroad by torturing ourselves.

It was Jimmy's first time in Canada.

We cleared US customs, then Canadian customs, and came out the other side to one of my closest high school friends waiting in a car park with the heat running. The relief of finally arriving, I can't even describe it. We were just so happy to be here. Little did we know that was just the beginning of our immigrant struggles.

No apartment. No jobs. A cargo container somewhere on the Pacific with the rest of our lives in it. You're probably wondering, two guys in their mid-twenties affording this? We're far from rich. Middle class at best. We were taking a huge financial risk with what little we'd saved. I had to pull my investment money. Jimmy had savings from working two more years than me. I felt like I couldn't breathe at times because of how anxious and stressed I was. But we were also never more determined in our lives.

We stayed in an Airbnb for a few days, then a friend's parents' basement over Christmas. Saw four or five apartments. Too small, too old, too expensive. Then we walked into a one-bedroom plus den in Port Coquitlam and we both just knew. Put in an offer on the spot. Approved the same day. Sat in the car outside just looking at each other and smiling.

That apartment became home for the next four years. It's where Proud Zebra became a real business.

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He Told Me He Couldn't Do This Anymore

Six months in, Jimmy broke down mid-argument in our 700-square-foot Port Coquitlam apartment. We were going back and forth about what to reorder. The usual stuff that sounds small but never is when you run a business with your partner.

Then it stopped being about inventory.

He told me how he was feeling, which was rare. He missed his friends, his family, Singapore food. He felt like he had nobody here except me. He couldn't find a job. The business wasn't making enough to really live on. And working on it together every day was slowly destroying us.

We moved to the bedroom. I held him and we both cried. I cried a lot that night too. Because he was right about all of it.

I've moved so many times in my life, so being far from people I loved was something I'd already been used to. Jimmy had never done it. Everyone he'd ever known was 16 hours away by plane. And I'd been so obsessed with building the business that I couldn't see how much he was drowning.

That night we agreed: the relationship comes before the business. Always.

We drew lines on how much we were allowed to work. Ensured quality time for each other and at least one weekday just to relax. Proud Zebra suddenly felt more sustainable when I finally opened my eyes and looked at it like a marathon rather than a sprint. He was right again. Success cannot be rushed.

How I Convinced Jimmy to Help Run Proud Zebra

For the first two years of Proud Zebra, Jimmy wanted nothing to do with it.

He said it straight from day one: "I'm supportive, but I don't want any part of the actual work." He was working full-time in marketing in Singapore, earning good money, and he cherished the line between work hours and life hours. Proud Zebra was my thing. Not his.

And as much as I tried to respect that, it was also hard to understand why he wasn't willing to help. I saw this as an investment in our future, not just mine.

Then we moved to Canada. Everything shifted. Jimmy struggled to find a marketing job here. Different market, different network, no local references. Months went by. He was getting frustrated. I was watching him sit with nothing to do while I was drowning trying to run the business alone.

So I asked him. Just help Proud Zebra in the meantime. Until something permanent comes through.

He agreed on one condition: he'd only touch sales, marketing, and logistics. No design. No customer service. No picking the fonts on a product listing. The stuff he's actually good at and enjoys.

And honestly, it was the best decision. From then on, Proud Zebra just kept growing. But it took years to figure out how to work together without destroying the relationship in the process.

Our Apartment Turned Into a Pharmacy and We Stopped Having Friends Over

When we first moved into our place, it felt like a home. We hosted hot pot nights. Korean BBQ. Friends would come over and we'd cook and hang out and it felt like we were building a real life here.

Then the business started growing.

First it was one shelf. Then two. Then six metal shelving units lined with bright yellow bins I'd bought because I thought they'd look cheerful. They did not look cheerful. It ended up looking like a pharmacy.

Our dining table became a permanent packing station. The kitchen fit one person at a time. Every time a new shipment arrived it looked like a bomb went off in the living room. By year two, 80% of the apartment was inventory. Every time we took photos, people would ask why we were in a storeroom. We stopped inviting people over because the place always looked like a permanent disaster. It felt claustrophobic, like the walls were literally closing in.

Nobody tells you this part when you start a business from home. The part where your home stops being a home and becomes a storage unit that you also sleep in.

I knew inventory management was hard. I used to work at an architectural warehouse. But I never understood how it impacted everything from logistics to bookkeeping to analytics to reorders. It's just so challenging when you're running it from your living room.

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How a Neurodivergent and a Neurotypical Run a Business Together

I have ADHD. Jimmy is neurotypical. We run a business together from our apartment.

It should be a disaster. Most days it's actually why it works.

New thing, unfamiliar, needs figuring out from scratch? My brain lights up. Building the website, teaching myself bookkeeping, finding suppliers in China, learning new software for any reason. If it's never been done before, I'll hyperfocus until it's done. A lot of my hyperfixations have been beneficial to the business. Photography. Video editing. Marketing. I fell so deep into marketing that it became my full-time career.

Repetitive stuff that needs consistency? Jimmy. He'll put pins on backing cards for hours, pack orders, count stock, file receipts. No complaints. No wandering off. Just execution. I physically cannot do the same task repeatedly without losing my mind. Jimmy has zero interest in learning new systems. After five years, we know who picks up what based on what it requires.

He plans every pride market, every business trip, every booth setup, every travel route between cities. He applies for all the different pride markets. If we make it through summer without imploding, it's because Jimmy planned our way through it.

For two straight years, every argument ended the same way: "Fine. Do it your way." That was Jimmy. Because in his head, this was MY business and he was just helping me run it. Every time he gave me an idea (and he works in marketing, so his ideas were usually good), I'd question it. Not because I didn't trust him. Because that's how my brain works. I need to understand the WHY before I do anything. But Jimmy can't always explain the WHY. He just knows. And when I'd push him with questions, he'd hear it as me looking down on him. Which I wasn't.

Here's a painful example: I wanted custom backing cards printed for every single pin design. Over 100 designs. Jimmy said just do one generic card. I said no, wholesale orders need to look professional with design-specific cards. We printed them all. Thousands of cards. We still have most of them sitting in bins. Because when you have that many designs, and half of them are niche identities like demiboy, you're not exactly flying through those backing cards. He was right. I should've printed them as needed. I had to learn that the expensive way.

We've never once considered breaking up over this business. But we've seriously considered shutting it down to save the relationship. More times than we care to admit.

Without Jimmy, Proud Zebra would not still be here. That's the honest truth.

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The Moment That Keeps Us Going

We've seriously talked about quitting this business. More times than we'll admit. Like sat-down-on-a-walk, should-we-just-stop conversations.

The late nights. The apartment that turned into a warehouse. The fights. One summer, we did 13 pride markets. Almost every weekend. I looked in the mirror, absolutely burnt and exhausted, and thought to myself "Is this really worth my health?" Granted, it was our own fault for signing up for 13 markets that summer. We'd sacrifice our weekends, start Monday more tired than we were on Friday. Being in the tent all day in the heat. It's as much as it is enjoyable, it is tiring.

The challenges are constantly evolving. One day it's logistics, the next day it's marketing, the next day it's bookkeeping. I do my bookkeeping once a year and I'm getting better at it, but it's not easy staying organized and disciplined.

But on the hard days, we come back to one moment.

Chilliwack Pride Market on a Sunday afternoon. A mom walks up with her daughter. Kid's maybe 13, 14. Quiet. Looking at all the pins. Not saying much.

Then she picks one up, turns to her mom, and says "I want the lesbian one."

That's how her mom found out. Over a $15 pin. At our booth. Her mom emailed us about it a week later.

This isn't rare. We receive emails from customers who share their coming out stories. Parents email us. Even grandparents have emailed us about their grandchildren coming out. It's the most touching thing, and it's what really keeps us going.

And we hear this at almost every pride market, especially for identities like aroace, demiboy, and demigirl, the ones most brands skip:

"Oh my god, IT'S ME. You guys actually have this one."

On the hard days, and there are a lot of them, we come back to these moments. Every single time. This is why we keep going.

"I bought a family set of pride pins for Christmas in support of our trans son and couldn't resist this bag charm. All products have beautiful, vibrant colours and are of excellent quality. My son's reaction as we all dove into the collection was more than worth it. Thank you for helping make our world a prouder one."
- Donna H.

"I came out as trans to my friends and family on National Coming Out Day this year. As a celebration I got myself the three pack of Transbian Cube Pins. They are wonderful and every bit as amazing as I had hoped they would be."
- Kayri

"I absolutely LOVE my community ally pride pin. I wear it PROUDLY on my work ID badge, and it starts conversations when people ask 'what does your pin mean?' I love telling people why being an ally is important and what 'community' means to me, and this pin helps me do that!"
- Lynn A.

Find Your Identity Pin

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What Are Pride Markets Like? 4,800km Across BC in One Summer

Every summer we pack up the car and drive to pride festivals across British Columbia: Kelowna, Victoria, Kamloops, Sunshine Coast, Chilliwack, Vancouver. We love the Sunshine Coast. A lot of these locations surprise us.

Setting up involves figuring out where our booth space is going to be. Near the food trucks or near the stage. Sometimes I get overstimulated if it's near the stage because it's too noisy, but it's also better for visibility.

We've made friends with vendors beside us. Met other pride merch owners like Dustin from Rebellious Unicorn. Gone to drag shows because of the business. We've taken hundreds of photos of customers at markets, and we're so thankful for everyone willing to let us photograph them, because that's what helps us build trust.

We designed our PZ shirts using the Proud Cubes patterns, and at every market people ask to buy them. We've thought about selling shirts, but the inventory would be insane. Enough sizes, enough identities. It just doesn't feel worth it when we already have stock taking over the apartment.

Last summer we drove 4,800km to 9 pride markets. Our packing lists. Our forgetting things. The routine of breaking down, driving, and setting up the next morning. It's exhausting and it's the best part of the year.

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What We've Built So Far

We started with three charity pin designs. Today we design LGBTQ+ pride enamel pins, proud cubes, pronoun pins, bag charms, drawstring bags, twilly scarves, croc charms, shoelaces, stickers, and greeting cards, all available in 35+ pride identities.

We chose products that are small, easy to ship, and easy to get to people across the world, because we want to engage a global audience. We've shipped to countries all over the world from our website and Etsy, and yes, there are so many challenges that come with that, including international taxes and customs. But every time you deal with a new problem, you level up.

5,000+ customers worldwide. 60+ wholesale accounts across North America, including HarperCollins, TJX, and Come As You Are. We're in over 400 stores across Canada through TJX alone. Every product designed by us. Every order packed by us. Still running this whole thing from home, after our full-time day jobs.

Because Jimmy and I both have full-time jobs. We work on Proud Zebra after working hours, and that's exhausting. We use most of our energy during the day. But we still do it and we're still dedicated to our community.

"I was looking for pins for me and my coworkers that also support human rights and aren't just an international company trying to make money off of the LGBTQ+ community. Having an amazing style for pins was just a bonus."
- Casey H.

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Why Is It Called Proud Zebra?

We didn't pick a zebra because it looked cool. We picked it for three words: community, freedom, and identity.

Community. Zebras are herd animals. They look out for each other. They recognize each other's stripes and can literally tell one another apart from a distance. A species that's survived millions of years because they stick together.

Freedom. Zebras can't be domesticated. People have tried. For centuries. Zebras refuse. They stay wild. Nothing about them fits into a box someone else built. That's the kind of freedom we believe in: the freedom to love and be your most authentic self.

Identity. Every zebra's stripes are unique. Not one pattern matches another. Like a fingerprint. That's why we design for 35+ pride identities instead of just slapping a rainbow on everything.

Those three words shaped everything: why our charity pins exist, why we design for identities most brands skip, and why we show up at pride festivals across BC every summer.

Not a unicorn. A zebra. That felt more honest.

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What's Next for Proud Zebra

We've been running this business for six years. We've made so many mistakes. We still have products that are tough to sell. We've tried outsourcing on Fiverr, engaged virtual assistants. None of it really worked for a business this cyclical. We're a two-person team with full-time jobs. We're limited on time.

But we're still here. Still adding identities. Still packing orders from our apartment. Still showing up at pride markets every summer.

If your identity is one of the 35+ we carry, we made it for you.

Shop by Identity

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Questions About Our Story

How did Proud Zebra start?

I (Delwin) founded Proud Zebra in 2020 in Singapore. After leaving a career in architecture, I designed over 200 LGBTQ+ pride pin designs across 30+ identities before writing a single listing. We launched on Etsy and Shopify, and moved operations to Canada in December 2021 when Jimmy and I relocated to British Columbia.

Who are the founders of Proud Zebra?

We're Delwin Tan (he/him) and Jimmy Cheang (he/him), a queer couple who met in the Singapore army. Delwin handles design and creative direction, while Jimmy manages sales, marketing, and logistics. We run the business from our home in the Lower Mainland of British Columbia, Canada.

Why is it called Proud Zebra?

We picked the zebra for three traits that reflect LGBTQ+ values: community (zebras are herd animals that recognize each other's stripes), freedom (zebras can't be domesticated), and identity (every zebra's stripe pattern is unique, like a fingerprint). Those three words guide every product and business decision we make.

Where can I buy Proud Zebra products?

You can find us at proudzebra.com, on Etsy, at pride festivals across BC during summer (June through August), and through our 60+ wholesale retailers across North America including HarperCollins, TJX, and Come As You Are.

How many pride identities does Proud Zebra carry?

We design products for 35+ pride identities, including bisexual, lesbian, transgender, non-binary, asexual, aromantic, demigirl, demiboy, genderfluid, aroace, Two-Spirit, and many more. We do our best to represent identities most brands overlook.

Does Proud Zebra donate to charity?

Yes! We've donated over $10,000 to LGBTQ+ organizations to date. We have six charity pin designs where 100% of net proceeds go directly to the related charity. Recipients include organizations supporting LGBTQ+ youth homelessness, community health, and refugee services.

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Related Reading

• The Complete Guide to LGBTQ+ Pride Flags
• Our LGBTQ+ Charity Awareness Pins
• Explore the Proud Cubes Collection
• Subtle, Cute & Unique Pride Pins to Express Your Identity

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Written by Delwin Tan, co-founder of Proud Zebra. Delwin and Jimmy design LGBTQ+ pride accessories for 35+ identities and run the business from their home in British Columbia.
Published May 2026. Last updated May 2026.
Proud Zebra is a queer-owned Canadian small business. We've donated over $10,000 to LGBTQ+ organizations to date. See where your support goes.