A Conversation with Jen from Hightail Hair
Updated: Sep 23
Who is Jen? The founder of Hightail Hair, a helmet-mounted solution that prevents tangles, wind damage, and helmet hair, so you're ride-ready in seconds. (That's directly from their website) She had a brutal battle with a hairbrush so she built a product that would help tens of thousands of riders.
Jen was on a break from riding her own bike and was on the back of her partner Jon's bike, hair up in a bun, and she did not even know her hair tie came out, until they got where they were going. Her hair is super fine, which means it goes into thousands of tiny knots.
They were trying to go to dinner. She stood there brushing and brushing and brushing, close to tears.
"That experience was seared in my head."
But you have to know who Jen is before you make a judgement here. Jen's first time on two wheels was a summer camp minibike, which she enjoyed more than she expected. Then Kill Bill came out, and the Japanese sport bike scene planted a little seed in her head.
When she grew up she became a naval officer and her first duty station was Japan.
She took the MSF course before she shipped out, got her license, and bought a 400cc Suzuki sport bike once she landed, specifically to chase a little of that Uma Thurman feeling for herself.
She would ride out into the Japanese countryside alone, wander around on purpose, and then find her way home by whatever landmarks she could remember on the way out. This was 2005 to 2007, GPS was not a common thing yet.
"I barely knew what I was doing. I'm just glad that I made it okay."
After Japan she moved back to the US where she met her partner Jon, a New Zealander who has ridden since he was a teenager. Which is how she ended up on the back of that bike, on that highway, with her hair coming down.
She was already hunting for a business when it happened. Jen has suffered from the entrepreneur bug since she was a kid putting together little businesses.
Then Jon said, well, why don't we try and solve this? (speaking about long hair and motorcycles)
They googled and googled, certain somebody had beaten them to it. "I guess we're gonna have to do it."
The hand sewn prototype of Hightail worked almost immediately, but it would take two years to get this to market. The product worked on the helmets they had, but it proved to be a real challenge to create a mount that would be almost universal to all helmets.
The front of the mount has to sit flush, because that is where the elastic pulls down. And Jen insisted it be removable rather than permanent, because people change their minds and people get nervous about sticking things to a helmet they paid for. Removable meant they would actually try it.
Then the sewing, which was surprisingly tricky to nail down. "Finding people who could sew to plastic."
She ran two sewers in parallel. One was a swimsuit sewer, because the material is stretchy and difficult. One was an industrial sewer. Jen physically carried prototypes back and forth between the two of them.
Two years of that.
The first landmark that told her she was going the right way was the Gas Tank program, the Motorcycle Industry Council's miniature version of Shark Tank for small businesses in the sport. She used it as a live test. The prototypes cost them over a hundred dollars each to produce. They sold them for forty.
But people bought them! So they went to manufacturing, and today the thing is patent protected and sitting in a lane nobody else opened.
When she demoed it for me, helmet on like normal, grab the hair, tuck it in. Done. And when she pulled the helmet off, the whole thing came cascading back out, which is a moment they did not design and did not expect.
"We didn't know that the magic movie moment was gonna happen."
It also keeps hair off your neck, so you get the breeze, and you are not peeling a sweaty bundle of hair off your skin at every gas stop.
That lane has turned out to be a good place to be. The distributor model never worked for them, they tried to work with RevZilla and it did not come together, so Hightail runs on a direct to consumer model. Keeping with that model has kept her relationship with the customer very authentic.
I asked whether the big consolidated players ever felt like a threat.
"I don't feel like those big players see us as threatening, I think they just haven't really paid that much attention to us, to be honest."
They have not looked closely enough to notice the math either. The industry works off a figure of ten to fifteen percent for women riders. Jen thinks it is closer to twenty five, but Hightail caters to both the rider and the passenger, so their number is likely even higher than that.
She would know. A lot of Hightails get bought by men for the person riding behind them. And it's important to note, Hightail is not just for women. Some get bought by men for themselves, because plenty of guys have long hair.
Jen is the type of person who looks at an opportunity, decides she is going to try it, and works out the map on the way. Hightail is carving its own path through the riding world.
"One of my biggest goals was to have stories to tell and a life that was adventurous. That meant I needed to keep an open mind and go where opportunities lead me. And I think I've done a pretty good job with that really huge overarching objective, to have cool stories to tell."
I asked her the same question I ask every guest, what is the ride that will stick with you forever. Jen mentioned a few, including the Great Ocean Road in Australia, the South Island of New Zealand, which she rode this past February, the Blue Ridge Parkway, practically in her backyard and a road called Huguenot Trail ten minutes from her house, where the trees arch all the way over the pavement.
Eight years in, two years building and six selling, Hightail has moved tens of thousands of units. Which means tens of thousands of people have avoided the knotty mess Jen fought before dinner. She prides herself in the fact that her customers can get off a bike and walk straight into dinner.
"It's very sweet. I'll be at events and women come up to me and say, you're Jen, thank you, I really love my Hightail."
The Takeaways
Typically I have three takeaways here that are for new riders, experienced riders and all of us, but Jen's story should speak to everyone. Simple solutions can take time to develop, don't rush it, get it right. Hightail took two years to get right, as a rider it can feel frustrating to work on something so small but the payout is always worth it.
