“It was probably the one time in the past couple of years I wasn’t searching for a business opportunity that I created the business I’m doing,” says Henry Lanham, co-founder of Wai Wear.
Henry has spent the last couple of years barely scraping by in California. After a series of bad breaks, he started renting out everything from his house to cars to brain-scanning machines and barely broke even. Burned out and needing a break, he and some friends took a life-changing trip to Thailand and ended up starting a clothing business.
Despite a rocky start that included borrowing from the bank to pay off loans from friends, Wai Wear today is by most measurements a successful ecommerce business with over $1.5 million in sales in the past year. Henry and his brand pushed the boundaries of “heteronormativity in fashion” and Wai Wear’s “look cute guarantee” helped get it where it is today.
How to Live for Free in San Francisco
After graduating with a bachelor’s degree from Brown and spending time studying in Asia, Henry moved to San Francisco hoping to make his break.
“I thought I was going to hit it big and I didn’t see any of the expenses as an issue. Two thousand dollars for a room? No problem!” laughs Henry on the phone.
He claims he spent most of his early days in California working as an account executive at a security company, enjoying himself, and attending concerts. Not particularly worried about his future career, money, or his next paycheck. However, the easy life soon began to crumble.
“I got this huge concussion and didn’t do anything about it. Just kept on partying and going to concerts,” says Henry.
But he quickly realized his untreated concussion was much more serious than he had imagined. Serious enough that he could no longer work properly.
“I just couldn’t function because of the concussion,” says Henry. “I was losing track of things during meetings. I was even having trouble doing math. I had to leave and start hustling.”
And hustle he did. He left the job and moved to save on rent. At this time, Henry boasts working as many as five different jobs while living with his girlfriend.
“For ten months I lived with my girlfriend and sublet my place to my friends,” says Henry. “I was doing car rentals, I was renting out biometric equipment, but I was sinking. Eventually, I’d angered three of my girlfriend’s roommates – because I wasn’t paying rent – and I had to get out.”
On a search for cheap rent, Henry moved to the wrong side of the tracks in the city he thought he knew well. His situation seemed to be moving steadily from bad to worse.
“I moved to ‘the Tenderloin’ neighborhood in San Francisco,” he says. “The first night I moved in I went to the corner store just to say ‘What’s up’ since they would be seeing a lot of me. The guys there said, ‘Why did you move here? This is the most dangerous corner in SF. See those guys over there? They will probably try to rob you at some point.’ So that got me worried,” says Henry.
After ten months he decided to move again, finally landing on a small piece of property he found on Craigslist. The owners let him fashion a six by nine-foot room for himself and his girlfriend and then they rented the house out to cover rent. But even this seemed barely sustainable.
“I was just treading water covering my expenses and my health,” says Henry. “I felt like all this was a wake-up call from the universe to change how I was living.”
An Escape to Thailand and a Discovery
Fortunately for Henry, he had made a couple of good friends in his time out on the West Coast. One was Tim Sae Koo, an angel investor and plant medicine advocate who had just sold his business. The other was Kelly Lazarra, a tech professional whose company was on the verge of shutting down. They got together and invited Henry to come with them on a month-long trip to Thailand.
Henry Lanham 
Kelly Lazarra
“One friend had just sold his business and one friend’s business had shut down. I was renting out neurofeedback devices. We all were in the right spot to do something else,” says Henry.
So the three friends went on their trip to Thailand. While there, they noticed a fashion trend sweeping the country.
“Everyone knows those elephant print pants that are everywhere over there,” says Henry. “We saw it and thought it was cool but a lot of the prints were pretty cheap. However, we found this artisan who’d taken these Northern Thai patterns and made his own high-quality cut that was unique and beautiful. We wanted to bring them to the US so we asked him if he would be able to supply them for us. He said that many people had asked but no one had followed through yet.”
But the three entrepreneurs were different. They had been forged in the California startup scene and knew how quickly they could scale a business if they got things right. They made a deal immediately with the supplier and got down to business, creating a website and fulfilling their first order of 200 pairs of shorts in 2019. There was just one small issue:
“None of us knew anything about ecommerce,” says Henry.
Learning Ecommerce Through the School of Hard Knocks
As newcomers in the space with no advisors, Henry and company learned everything about ecommerce the hard way. Their first website was a Squarespace template. A simple landing page asking for emails in exchange for 20 to 25 percent off orders.
“We told ourselves if we get 200 emails from a fixed budget for ads then we’d invest and buy our first 200 pairs of shorts,” says Henry. “That happened in 2019. Our first order from the supplier sold out quickly. And then we just made bigger and bigger orders, and went back to Thailand two more times to talk with suppliers.”
At this point, Tim left the business to focus on running plant medicine journeys in South America and Henry and Kelly took the reins. Then the financial issues began to set in.
“We kept having inventory issues where we’d see we were going to run out of clothing and so we’d ask our supplier, ‘Hey, can you make as much as you can next month?’ because we were losing money by not having anything in inventory,” says Henry. “That fall, we kept ordering more inventory but our product was tight, colorful shorts that people buy in the spring and the summer. As you might guess, demand fell off a cliff in the fall when the weather got cold, but we’d still been building up inventory and didn’t have money to pay our supplier.”
Suddenly their promising new company seemed on the verge of collapse.
“Because of the massive orders, we didn’t even have $500 to pay our customer service guy in Spain at that time,” says Henry. “Between Kelly and I, we didn’t have a hundred dollars in our bank accounts. We did have some crypto but the market was down at the time.”
Thinking fast, Kelly and Henry began asking friends for money. But even this looked like it was going to backfire.
“First we borrowed $10,000 from one friend and told him we’d pay back $1,000 every week because we thought we would sell a lot,” says Henry. “We got halfway through paying him back and our sales dropped off further than we expected. We had to borrow money to pay him back and it was there we realized we had to both get jobs.”
The two co-founders picked up full-time work and turned Wai Wear into a side hustle. Then they became more systematic about expenses.
Today, Wai Wear is profitable and much more stable with close to 30,000 customers and about $1.5 million in sales this year. They have even hired a creative director, Alan Prijatel, and are moving into swimwear.
“What I’m most proud of is doing something with my friends that has worked,” says Henry.
Find Your Wai
Henry and co’s company is called Wai Wear hearkening to their Thai origins. Wai is a traditional greeting in Thailand, according to Culture Trip, and it’s also used for thanking someone, apologizing to someone, or saying goodbye.
“Why is Wai hella gay?”
That’s the tagline on the Wai Wear LinkedIn page. The brand primarily targets young gay and straight men who “unapologetically wear what they like to wear.”
“We have had a really robust community of customers since the very beginning,” says Henry. “Young gay guys and young straight guys who want to stand out and challenge heteronormativity. I think we’ve done a good job of building a community, especially Kelly and Alan.”
Henry himself wears his Wai Wear frequently as do Kelly and Alan who live in San Diego and Atlanta respectively. They all get a kick out of seeing their clothing at events or out on the street.
“When we see other guys and occasionally women wearing it we get super excited. We’ll go up and say, ‘Hey, those are nice shorts! That’s my company.’ And then they think that’s really cool,” says Henry.
Henry’s lesson to other founders embarking on a similar journey to his is to make sure you like the people with whom you start your business.
“If you wouldn’t work with someone for ten minutes, don’t work with them for a lifetime.”
“I think Naval Ravikant said, ‘If you wouldn’t work with someone for ten minutes, don’t work with them for a lifetime,’” says Henry. “Which is another way of saying it’s not enough that your skillset compliments your co-founder, you have to enjoy who they are as a person and have deep trust. I think that those are wise words and I’ve been lucky enough to work with a super close friend who I trust and admire. That would be my piece of advice to everyone out there. Do the same.”
Wai Wear’s story is more than one of learning finances through the school of hard knocks. It is about friendship. Henry may not have had the greatest luck or foresight in his early years, but he took the time to make great friends. Friends who were willing to work with him, lend a hand when he needed it, and offer their expertise in areas he lacked. That seems to have made all the difference.
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