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Tom Montgomery
Founder at Chubbies + Loop Returns | Sharing lessons from building 9-figure businesses and 10-figure outcomes
Tom Montgomery is an experienced Founder known for his exemplary leadership in brand building, having successfully built profitable 9-figure brands and thriving communities. With a background in Management Science & Engineering from Stanford University, Tom co-founded Chubbies Shorts, a renowned direct-to-consumer brand specializing in proper-length men's shorts. Under his guidance, Chubbies Shorts achieved undisclosed but impressive revenue figures and was later acquired by Solo Brands for over 9 figures.
During his tenure at Chubbies Shorts, Tom Montgomery spearheaded various digital initiatives, including end-to-end Marketing, E-Commerce, Data & Analytics. Post-acquisition, he continued his journey with Solo Brands as the Chief Digital Officer, overseeing pivotal aspects of the brand through its IPO on the NYSE (NYSE
Tom Montgomery's expertise spans a wide range of areas, including Data & Analytics, Performance Marketing, Brand Marketing, Creative Branding, Retention, Digital Product Management, Web Development, Web Merchandising, and Experimentation. He is a firm advocate of continuous learning and values qualities like humility, empathy, connection, and mathematical precision in his professional endeavors.
Throughout his career, Tom has been affiliated with several notable organizations, serving as an Advisor at Mandrel, GoodDay Software, Kinn, and an Investor in Constructor, Rupert, Fairing, Status, Toolio, Carro, ChannelApe, and more. He was a Founding Member of Guilds by FirstMark, Co-Founder of Loop, and Chubbies Shorts, and held the position of Chief Digital Officer at Solo Brands. Tom's investment portfolio includes diverse ventures in the tech and finance sectors, showcasing his keen interest in supporting innovative startups and contributing to their growth.