Diet Starts Monday is more than just a catchy phrase; it's a fashion brand that embodies the idea of seizing the moment and acting on your ideas today, instead of postponing them. This ethos, born from a casual saying between co-founders Davin Gentry and John Geiger, has propelled the brand from its humble beginnings to a recognizable name in the streetwear scene.
The Genesis of an Idea
The brand's name, Diet Starts Monday, originated from a common expression between Davin Gentry and John Geiger, used when they found themselves indulging while traveling. This simple phrase captured the spirit of procrastination and the desire for a fresh start, which they translated into a brand that encourages immediate action and the pursuit of dreams without delay.
From Hand-Painted Clothing to Diet Starts Monday
Davin Gentry's journey to co-founding Diet Starts Monday is rooted in years of experience in the fashion and design world. Starting with hand-painting clothing in college, Gentry honed his skills in advertising and graphic design at Western KY University. He later launched a jewelry line called Premium Co. with Tyler Hundley, whom he connected with via social media, initially offering gemstone bracelets before expanding to custom-molded pendants with 14kt gold and diamond options.
As Premium Co. evolved, Gentry began incorporating essential clothing styles, focusing on fabric, fit, and price point. This venture into clothing design, combined with a desire to explore more graphic-heavy designs, eventually led to the creation of Diet Starts Monday with John Geiger in 2016. The launch took place with a private showing at the Cosmopolitan in Las Vegas during the Agenda/Liberty tradeshows, coinciding with Premium Co.'s exhibition at Liberty.
The Evolution of Retail Strategy
Diet Starts Monday initially gained recognition with a retail and restaurant space in Washington, D.C., which became a hub for creatives after its launch in May 2017. However, this space was always intended to be temporary, lasting only three months. Davin Gentry explained that maintaining the space would have required their constant presence, hindering the brand's desired growth trajectory.
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Instead of relying on traditional wholesale models, Diet Starts Monday shifted its focus to global pop-up activations. These activations take the form of stand-alone spaces or stores within larger stores, allowing the brand to engage with diverse audiences in various locations. This strategy is similar to that of other streetwear brands, such as Joseph Robinson’s Joe FreshGoods, which are opting for activations in different cities rather than traditional wholesale approaches.
In 2019, Diet Starts Monday planned around 10 pop-up events, building on previous retail experiences in Miami during Art Basel at Alchemist, in Philadelphia at Lapstone & Hammer, and in Sao Paulo, Brazil, for a collaboration with Rider. Gentry mentioned that the brand determines its pop-up locations based on e-commerce sales data and a desire to build brand awareness in new markets. The pop-up in Sao Paulo, for example, significantly boosted Brazil's ranking from the 30th to the 10th most popular market for the brand.
Online Strategy: Limited Releases and Collaborations
Diet Starts Monday mirrors its pop-up strategy with its e-commerce approach, releasing mini capsules once or twice a month on Mondays. These releases are available for only 24 hours, creating a sense of urgency and exclusivity. The quantity of each item varies, ranging from 50 to 700 pieces, depending on the item and its intended level of scarcity.
The brand has also strategically targeted a broader audience through collaborations, such as its partnership with Five Four, which offered T-shirts around $20, knits around $45, and bottoms around $55. However, Diet Starts Monday has found its niche in the "midlevel high fashion price point," balancing accessibility with the brand's desired image.
Avoiding the Pitfalls of Fast Fashion
Diet Starts Monday is focused on sustainable growth and longevity, with a clear vision to avoid the pitfalls of becoming a fleeting trend. Davin Gentry emphasized the brand's commitment to scaling into a multimillion-dollar brand that endures for a long time, rather than being acquired and fading into obscurity.
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Design Inspiration and Authenticity
Davin Gentry draws inspiration from his personal experiences and childhood memories, infusing his designs with a sense of nostalgia and authenticity. He often incorporates nods to his upbringing, such as vintage sports capsules inspired by his AAU basketball sweatsuit or bike rally t-shirts referencing his Harley-riding uncle.
The brand specializes in creating modern garments that evoke a vintage feel, reminiscent of clothing from the past. Gentry emphasizes the importance of meticulous attention to detail, ensuring that each piece feels authentic in its graphic design, wash, and overall aesthetic. This dedication to quality and authenticity sets Diet Starts Monday apart in the competitive fashion landscape.
Overcoming Challenges and Embracing Destiny
Like any entrepreneurial venture, Diet Starts Monday has faced its share of challenges. Early on, the brand encountered issues with offering quality jewelry at an affordable price, experimenting with different types of plating and coating. In clothing production, they learned a valuable lesson when an initial price quote for sewing did not include fabric, trims, labels, and finishing, resulting in unexpected costs.
Despite these challenges, Gentry maintains a positive outlook, viewing setbacks as opportunities for growth and learning. He believes in destiny and fate, trusting that a higher power is guiding the brand's path.
The "Diet Starts Monday" Podcast
Extending beyond fashion, Diet Starts Monday has cultivated a strong presence in the podcasting world. The "Diet Starts Monday" podcast features a diverse range of topics, from endurance sports and functional fitness to entrepreneurship and personal development.
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Featured Episodes and Guests
The podcast has hosted numerous notable guests, including athletes, entrepreneurs, and experts in various fields. Some of the standout episodes include:
- #105. Hangovers to High Mileage with Carmichael Caldwell III: This episode features Carmichael Caldwell III, an entrepreneur, endurance runner, and founder of AIDN, discussing his journey from partying to running, lessons from injury, and the launch of his AI-driven health company.
- #103. Is Hyrox the Future of Functional Fitness?! Ft. The All Round Athlete - Sheldon Valjalo: Roscoe interviews Sheldon Valjalo about his transition from bodybuilding to Hyrox and triathlon, offering tips and inspiration for athletes.
- #102. We run for health, peace, and sanity. Each and Everyday: This episode explores the motivations behind running, the challenges of being a solo founder, and building a brand that prioritizes function, quality, and style.
- #101. Blood, Sweat & Stories: 100 Episodes Later: The hosts reflect on the journey of building the podcast, sharing behind-the-scenes stories, trials, tribulations, and triumphs.
- #99. Jamie Riddle - Professional Triathlete: Jamie Riddle discusses his journey as an elite triathlete, his training structure, and his mindset leading up to major competitions.
- Podcaster & Hyrox Athlete - The Mindset Podcast Ft. Angus Cook: Roscoe and Angus Cook discuss the struggles of podcasting, the rise of run clubs, and the importance of community.
- Jarryd Segal: Cape Town’s Culinary King: Jarryd Segal shares his journey of building iconic eateries in Cape Town, including Jarryd's Brunch & Bistro, Ariel Modern Italian, and NV-80.
- Luca Filippi - A South African Golfing Prodigy: Luca Filippi discusses his journey from junior golf to the Sunshine Tour, sharing insights on the challenges and adjustments needed to thrive as a professional golfer.
- The Influential Power of Running | Nick Bester - Sub 2:20 Marathoner, Coach, & Founder: Nick Bester discusses distance running and coaching, while Rachel Beaton shares her experiences with Comrades training and race day moments.
- Running From Cape Town to London | A 518 Day Journey Across Two Continents - Ft. Deo Kato: Deo Kato recounts his 13,000-kilometer run from Cape Town to London, highlighting the historical significance of his journey and the challenges he faced.
- Kate Moyle - The Science of Sex | Everything About Your Sex Life Answered: Kate Moyle discusses the science behind sex and intimacy, exploring topics such as communication, pleasure gaps, and the role of education.
- Clay X - What Does Sobriety Mean To You? Addiction, Recovery, and Vulnerability: Clayton shares his journey through addiction and recovery, discussing the transformative power of attending meetings and finding purpose in sobriety.
- Small Beer | The Worlds First Dedicated Mid-Strength Beer Brewery: The founders of Small Beer discuss their mission to create flavorful mid-strength beers and the challenges of marketing a product with no direct competition.
- Chris Taylor | The Endurance Epidemic - What Is Causing This BOOM In Endurance Sport?: Chris Taylor explores the global "endurance epidemic," discussing the motivations behind pushing limits and the mental and physical barriers athletes face.
- The Power of 5 Grams with Mrs P: Psychedelic Healing & the Journey Within: This episode delves into the world of psychedelic therapy, with a guide sharing her experiences with psilocybin mushroom journeys and the potential for healing.
- Dr Priya Gopadas - Starring in Love Island, Becoming an Alpinist, and Running Ultra Marathons: Dr. Priya Gopadas discusses her experiences as an NHS doctor, Love Island contestant, and adventurer, balancing her medical career with endurance sports.
- DSM Q1 Reflection: Setbacks and Successes: The hosts reflect on the ups, downs, and curveballs of the first quarter of 2025, discussing their goals, setbacks, and small wins.
- Fueling For Performance with Certified Nutritionist - Johan Florez: Johan Florez breaks down the Fueling for Performance Hierarchy, emphasizing the importance of focusing on the basics for sustainable results.