Jack Boland
Jack Boland is the founder of Wompy Bikes, a San Francisco-based company that creates custom bike bags and accessories. Starting from a passion for cycling, Jack built a brand that combines function with style, serving riders who value quality gear for their rides.
Jack Boland's Bio
Jack Boland is the founder of Wompy Bikes, a San Francisco-based company that makes custom bike bags and accessories built to order. Using software Jack developed in-house, customers upload a photo of their bike and design a frame bag to match its exact shape and their personal style, printed on 100% recycled fabric.
Jack grew up mountain biking at Wompatuck State Park in Massachusetts, where the park's local nickname "Wompy" gave the company its name. He attended Stanford University from 2019 to 2022, then moved to Fort Collins, Colorado, when his partner went back to school. Living car-free in Colorado, Jack started commuting, climbing, and hauling groceries entirely by bike, and during his first winter there he realized cycling was not only possible, it was the best part of his day.
An obsession with making things drove him to design and build multiple iterations of bike bags for carrying his belongings, and those early prototypes became the seed of Wompy. The philosophy that emerged was simple: make it easier and more fun to ride, and more people might realize they do not need a car. Jack launched Wompy Bags in June 2024 and developed the in-house design software alongside the product itself.
Wompy Bikes now produces every bag to order with custom fabric printing for each customer. In 2025 Jack joined the HIBT Advice Line with Marcia Kilgore to work through optimizing his sales funnel.
Career Timeline
2019 — Enrolled at Stanford University
Began studies at Stanford University in California.
2022 — Graduated Stanford University
Completed degree at Stanford University.
2022 — Moved to Fort Collins, Colorado
Relocated to Fort Collins, CO when partner returned to school; began living car-free.
2024 — Designed first Wompy bike bag prototypes at Wompy Bags
Built multiple iterations of bike bags; Wompy philosophy took shape.
2024 — Founded Wompy Bags at Wompy Bikes
Officially launched in San Francisco with custom-fit bags and in-house design software.
2025 — Featured on HIBT Advice Line with Marcia Kilgore
Appeared on HIBT Advice Line (episode 821) with Marcia Kilgore for founder coaching.
Episodes
Advice Line with Marcia Kilgore of Beauty Pie (June 2025)
In this Advice Line episode, serial entrepreneur Marcia Kilgore, founder of Beauty Pie, guides three early-stage founders through pressing business challenges. Victor Garcia of Sol Dias Ice Cream weighs expanding retail versus wholesale. Lydia Welsh of Clerstory struggles with fear of rejection in marketing her skincare line. Jack Boland of Wompy Bikes aims to optimize his custom bike bag sales funnel. Marcia offers a masterclass in practical founder coaching with advice on testing with ads, simplifying choices, and creating flagship experiences.
Advice Line with Marcia Kilgore of Beauty Pie
Marcia Kilgore joins the Advice Line to guide three early-stage founders through growth challenges. Victor in Fort Worth weighs brick-and-mortar expansion against retail distribution for his Mexican sweets brand. Lydia in Seattle seeks to scale her small-batch botanical skincare line while overcoming fear of failure. Jack in San Francisco wants to maintain customer excitement throughout his custom bike bag brand's purchasing process. Kilgore draws on her experience building Beauty Pie, Bliss, and Soap & Glory to offer candid advice on scaling, risk, and staying true to your brand.
