Bennett "Jolly" Fisher, Founder of Jolly Gear, on Triple Crowning and the Evolution of His Signature Shirts

In today's episode of Backpacker Radio presented by The Trek, we’re joined by Bennett “Jolly” Fisher, the founder and visionary behind Jolly Gear. We learn all about Jolly's entry into backpacking, including his first thru-hike at just 18 years old alongside his dad, hiking 300 miles of the PCT on a broken ankle, and some hilariously embarrassing Jabba stories from their recent hike on the CDT. We, of course, dive deep into his apparel company, Jolly Gear, and how he's flipped the thru-hiking fashion world on its head with his unique sun hoodie button-downs. We chat about the biggest challenges associated with running an apparel business, how a misunderstanding lead to his early signature design, how he manages the business while backpacking, his process for sourcing new designs, and much more.

We close the show with the triple crown of cringeworthy things, a discussion of what should be free but isn’t, an impromptu drop-in from Jabba, and an AT conditions update courtesy of Quadzilla.

Gossamer Gear: Use code “SNUGGLEBUG” for 20% off shelters at gossamergear.com. 

LMNT: Get a free sample pack with any order at drinklmnt.com/trek.

Trailbrush: Use code “TREK20” for 20% off trailbrush.com. 

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Interview with Bennett “Jolly” Fisher

• Jolly Gear Website
• Jolly Gear Instagram

Time stamps & Questions

00:02:50 - Reminders: Help us make Jabba shave his beard, support us on Patreon for exclusive bonus content, join us in Denver on December 7th and apply to be a 2025 blogger!

00:08:00 - Introducing Jolly

00:12:38 - We Love Love: Tell us your engagement story

00:16:05 - What was your entry into backpacking?

00:21:20 - Did you consider quitting early on in the AT hike?

00:23:00 - What was your social experience like on the AT?

00:24:15 - How’d you get your trail name?

00:27:00 - Has your dad hiked again since the AT?

00:28:30 - How did your parents support you starting out on the PCT?

00:30:15 - At what point did you get into shirt research?

00:33:00 - How far did you get on the PCT in 2017?

00:34:00 - Why’d you get off the trail in 2017?

00:39:10 - Tell us about your foot injury in 2021

00:45:42 - Are you still adjusting your footwear?

00:50:13 - At what point did you first want to design a hiking shirt?

00:53:00 - Discussion about the Outdoor Product Development program

00:56:14 - Did your first shirt have your signature design?

01:01:12 - Do you get good feedback about having women’s sizes?

01:02:00 - Was there anything functionally different between your prototype and what was on the market?

01:05:09 - How did the style evolve?

01:11:00 - Are all the shirts the same UPF?

01:12:23 - What material is the shirt?

01:15:23 - Have you ever thought about making shorts?

01:19:40 - What’s your day to day like?

01:21:40 - Do you have a vision for where you want the brand to be in 5 years?

01:24:54 - Are you planning to ever use the snap buttons?

01:27:00 - Discussion about pursuing a denim shirt

01:29:50 - How do you decide on future patterns?

01:30:54 - What’s the biggest challenge of your job?

01:32:43 - Have you seen other brands imitating some of your patterns?

01:34:50 - What’s the best Jabba story you have?

01:44:40 - Kumo Question: What is the one thing you wish you were better at?

01:47:13 - What’s next for you?

Segments

Trek Propaganda: 

• Trek for Trevor: Get 20% off a pair of microspikes before you hike through the San Jacinto Mountains on the PCT. 
• Jack “Quadzilla” Jones: On-the-Ground Hurricane Helene Status Update and 2025 Predictions by Kelly Floro

QOTD:  What should be free but isn’t?

Triple Crown of cringy things

Mail Bag

5 Star Review

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