Pursuit of Happiness: How Wise Owl Outfitters Became a Blockbuster Amazon Ecommerce Business

The founder of Wise Owl Outfitters, Sarah Douglass, remembers the day that she and her husband, Todd, walked out of a national outdoors retailer with all the equipment they needed for a backpacking trip – and an eye-popping receipt for $2,500. 

“That seemed like a whole lot of money to spend to enjoy nature,” she says. “And a lot of people wouldn’t be able to afford it.” That bothered her. A lot. 

To Sarah, nature was a place for restoration and rejuvenation. She felt that everyone should be able to experience that – and the price of admission to the Great Outdoors, by her calculation, should be as close as possible to free. 

“There’s scientific evidence that being out in nature makes you happier and brings you joy,” she says. “And I was like, if we can make people happier, and bring more joy by getting more people outside, then why wouldn’t we want to do that?”

I oughta… Someone should make a… It would be great if… Plenty of people have thoughts like these. But most people don’t have the ability, tenacity, or audacity to act on those ideas, much less see them through to completion. 

But Sarah Douglass, now 38, is not most people. She has a mission-driven entrepreneurial determination that drives her to outwork everyone else. She doesn’t see failure. (“I make mistakes, but I learn from them, so to me that’s not ‘failure.’”). Which is how that whopper of a bill propelled Sarah to launch and grow Wise Owl Outfitters, a multi-million–dollar Amazon ecommerce business that today sells the #1 best-selling hammock on Amazon in both the camping and patio categories, along with camping pillows, bug nets, and a whole bevy of hammock accessories. 

Sarah Douglass: the making of a self-made entrepreneur

The “Education” section of Sarah’s LinkedIn profile contains just three words: School of Life. No fancy degree, no community college, not even a GED. According to standard career advice, those are minimum requirements for professional success. Sarah Douglass didn’t get that memo. 

She grew up around Los Angeles and was pretty much done with school at age 13. Her dad owned a construction company, and by age 17, she was out on  work sites, too, overseeing teams to “make sure jobs were being done properly and on time.” 

Her family went to Hawaii once — the only “real” vacation they ever took. Other than that, it was twice-yearly trips to the Strawberry Music Festival in Camp Mather near Yosemite. Families pitched tents or strung hammocks between the pines. There was folk and bluegrass music and jam sessions going all day and night. Kids roamed the woods and spent hours swimming and crafting. The whole experience ended with a Sunday revival at Birch Lake. For her, the festival was the pinnacle of childhood happiness; for her family, it also happened to be a vacation that was pretty close to free.

Around 18, Sarah briefly decided to try her hand at school again. She became pregnant. And that was that. She started a new chapter as a single parent, working 2 or 3 jobs at a time to raise her son. Of course, it was hard.

“I am grateful for everything that has happened to me in my life,” she says. “It has made me who I am today. I have a very strong sense of personal responsibility.”

Sarah spent plenty of years working for other people. A pattern emerged. She’d learn the business until she could pretty much run the business, then she’d ask for a big raise, and walk if she didn’t get one. She walked a few times. She was good at working, liked working – it was the working “for other people” part that needed changing. Along the way, Sarah met her now-husband, Todd, who shared a similar set of values, including a desire to strike out and build a business they could call their own.

Mission: make a great hammock at a great price 

Eventually, they took an FBA (Fulfilled by Amazon) course from one of those self-appointed Amazon gurus promising an easy path to financial freedom through ecommerce. They got some 101-level basics out of it, but not much more. (“This course actually told people to stay away from hammocks as a product,” Sarah laughs now.)

But hammocks were a no-fuss piece of equipment that represented happiness to Sarah. Within a few minutes, people could be set up, relaxing, and listening to the gurgle of a stream, ocean waves, or a breeze in the trees. Hammocks were a way to get people enjoying nature fast, easy, and on the cheap.

Hammocks, as a product, also had some clear business advantages: they were relatively simple to manufacture and their compact size made them economical to ship. The fabric color and style options were endless, so they could always be on trend as customer tastes changed. Plus, Wise Owl could produce a lot of hammock accessories to eventually expand its product line.

Getting to the first Wise Owl sale for their Amazon ecommerce business took hundreds of hours of investment. Sarah and Todd ordered every hammock they could and spent a lot of time testing, tugging, swinging in, and even destroying them. “We have very high standards and that translated to our business as well,” Sarah says. “We didn’t want to sell something that we ourselves wouldn’t want to use and love.”

From the stitching thread counts to the way the seams felt on bare skin (after all, customers might be using a hammock while wearing shorts or a swimsuit), Sarah and Todd left no detail unexamined. Of the low-cost models, none passed the Sarah test. Too scratchy, too small, poorly made, too difficult to set up. She found one she did love – but it came with a nearly $100 price tag.

They had a mission for their new Amazon ecommerce business: Make the greatest hammock anyone ever owned at half the price. 

An Amazon ecommerce business success: Wise Owl Outfitters comes out swinging

When she was dreaming up the Wise Owl brand, Sarah created a script for a video ad. In her storyboards, she would proffer a Wise Owl hammock toward the camera and explain to viewers that what she was holding in her hand was not in fact a hammock at all… but happiness. Wise Owl was selling the feeling she had in childhood, what she wanted everyone to experience themselves.

In 2015, Sarah and Todd drew down their savings to place her first purchase order of 200 hammocks. The day the products arrived on her doorstep was another lesson in the challenges of building an Amazon ecommerce business. She opened the box and … the Wise Owl logo was the wrong color. Even worse, the hammocks were stuffed into long and skinny carrying sacks. “They were basically two-foot-long sausages,” she says. She pulled them all apart and paid a local seamstress to fix every logo patch and every sack.

Sarah and Todd sold their first Wise Owl Outfitter hammock in September 2015, the same month they welcomed son Lincoln to the world. They sold through the first batch within a month. “After 200 we had enough money to buy 1,000, so we bought 1000,” she says. “And then the next round it was 2,000 and we just kept going.” 

Next stop for Wise Owl? Going global

Today, Wise Owl is a booming online Amazon ecommerce business. The hammocks are nearing 40,000 ratings and maintain an impressive average of 4.8. Wise Owl has earned dual Best Seller Badges in both the camping hammocks and patio hammocks categories, while its camping pillows and hammock bug net also have Best Seller Badges. In 2021 alone, the brand sold hundreds of thousands of units in its product line. At the end of 2021, the Camping Hammock was capturing the majority of the market share for camping hammocks on Amazon. 

“We watched reviews religiously to see if there was anything wrong with our product, and we’d fix it every single time there’s a problem,” she says. “We are constantly asking, What else can we do?”

Sarah never wanted to sell Wise Owl Outfitters. Revenue was trending up and to the right. “Eventually I got to the point where I knew I had taken it as far as I could on my own,” she says. “If I wanted to get even more people out in nature and lift people up, I would need to get strategic people involved.”

Thrasio bought Wise Owl Outfitters in May 2021. It’s one of 14 Amazon ecommerce brands Thrasio owns in the outdoor category. And her dreams for the brand? “I want Wise Owl to be a brand that creates memories for the most number of people,” she says. “I would love to see it in stores, places where people can just pick it up anywhere. So I needed people like Thrasio to come in and really get that going.”

This spring, Wise Owl Outfitters hammocks will launch in the Canadian, UK, and German Amazon markets – a huge expansion for what started as a small Amazon ecommerce business. Sarah briefly took a break after selling her Amazon ecommerce business, but like many entrepreneurs, she’s not really one to… just rest.

She’s laying the groundwork for her next brand. “Totally new category,” she offers. “All I can say is that it will be a product to help women. And of course my hope is that it will bring them a lot of joy.”