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Turning Side Hustles Into Small Businesses | Forbes
Inspiring Journeys of Passion and Perseverance
Dylan Sprouse: From Garage Mead to Master Brewer
At 16, Dylan Sprouse started brewing mead in dirty buckets in his garage, driven by a teenager’s curiosity about alcohol. Though his friends hated the early batches, his father surprisingly supported him—on the condition he respected the craft. Dylan experimented relentlessly, even selling mead in college dorms. After graduating, he interned at Brooklyn’s Kings County Distillery, learning the business side of brewing. Despite skepticism from the mead community and assumptions that his venture was a “celebrity endorsement,” Dylan persisted. Today, his dry meads win gold medals, and his Brooklyn-based meadery prioritizes local New York honey and ethical beekeeping.
Key Takeaway: Authenticity and ingredient quality are non-negotiable.
Bang Bang: Self-Taught Tattoo Artist to Studio Owner
Bang Bang taught himself tattooing in his mom’s kitchen, making “a lot of mistakes on people” before a mentor taught him safety and technique. At 19, he moved to NYC but faced rejection—shops doubted his portfolio. Undeterred, he took every challenging project to build his reputation. After years in street shops, he opened his own studio, curating artists with diverse styles. Transitioning from artist to CEO meant relying on experts: “Artists only want the tools to create… I have accountants, lawyers, and managers with skills I don’t have.”
Key Takeaway: Build a strong foundation; a crumbling house can’t grow.
Anthony McGill: Breaking Barriers at the NY Philharmonic
Growing up on Chicago’s South Side, Anthony McGill chose the clarinet to emulate his flute-playing brother. An early memory slip during a youth orchestra audition taught him that passion matters more than perfection. His teacher’s advice—“Somebody is born better than you every day”—fueled his humility. After failing his first NY Philharmonic audition, he mapped a six-year plan and eventually became their first African American principal clarinet. His career pinnacle? Playing alongside Yo-Yo Ma at President Obama’s inauguration.
Key Takeaway: Focus drowns out detractors; never let others define your limits.
Rick and Raw: Building Burn Rubber, Detroit’s Sneaker Empire
Rick and Raw turned sneaker passion into profit by driving from Detroit to NYC to resell rare kicks. They bought Burn Rubber in 2005 (funded by family after banks rejected them) and leveraged relationships—like mentoring a young Big Sean—to amplify their brand. A viral stunt selling Yeezys for $1,000 (then $4,000) landed them on CNN and MSNBC. Their grassroots hustle helped reshape sneaker resale culture, paving the way for StockX and GOAT.
Key Takeaway: Community and audacity create opportunity.
Claudia Oshry: From “Girl With No Job” to Media Mogul
After getting fired from a fashion internship, Claudia Oshry launched the blog Girl With No Job, chronicling her misadventures. Instagram traction led to podcasts, comedy tours, and DJ gigs. She taught herself business logistics—“Google ‘how to file taxes’”—and trademarked via a “sketchy 1-800 lawyer.” Her strategy? Blend relatability with aspiration and pivot with trends: “When Instagram launched Stories, I embraced it instead of clinging to Snapchat.”
Key Takeaway: Master the “boring stuff” (accounting, trademarks) to scale creativity.
Amita and Ross: Flour Shop’s Exploding Cake Revolution
Amita Kasem baked cakes for coworkers while working in fashion, realizing her side hustle had more potential than her day job. With husband Ross Harrow, she launched Flour Shop in NYC, prioritizing scratch-made ingredients over pre-mixes. Their “exploding cakes” gained fame for rainbow layers and hidden confetti. Early struggles? Hiring a dishwasher after realizing bakers shouldn’t wash pans.
Key Takeaway: Invest in quality—your product speaks loudest.
Lewis Miller: Flower Flashes and Fearless Creativity
Lewis Miller’s floral career began pulling weeds at a Seattle golf club. He moved to NYC in 2000 with two suitcases, driven by work ethic over dreams of fame. After 18 years designing high-end events, he launched “Flower Flashes”—pop-up installations in trash cans or statues, using leftover blooms to surprise New Yorkers. What started as creative catharsis became viral PR.
Key Takeaway: Boredom is scarier than failure; create without overthinking.
Jake Schwartz: Disrupting Education with General Assembly
Feeling “lost and lonely” post-college, Jake Schwartz co-founded General Assembly (GA) to shorten the path from learning to employment. GA’s early days were chaotic—“Students left because the projector broke!”—so they staffed every class with support personnel. Raising venture capital was a turning point: “Once you take the money, you lose control of your story.”
Key Takeaway: Solve problems from first principles, not industry norms.
Danielle Bernstein: WeWoreWhat’s Fashion Revolution
Danielle Bernstein started WeWoreWhat as a FIT street-style blog. By blending “relatable and aspirational” content, she grew it into a multi-platform empire spanning design, tech, and investing. Hitting 1M followers was a milestone; constructive criticism from fans now fuels her decisions. Her advice? “Disrupt the industry—influencers created a whole new sector of fashion.”
Key Takeaway: Find an unsaturated niche and evolve with your audience.
WhIsBe: The Artist Behind the Gummy Bear Phenomenon
Self-taught artist WhIsBe (a college dropout) works across painting, neon, and sculpture, famously turning gummy bears into high-art collectibles. He rejects “procrastination” labels, binge-working on his own terms: “As long as I execute, how I structure time is my call.” His global reach defied early fears of irrelevance.
Key Takeaway: Fear is self-imposed; mute outside noise and trust your process.
Source: Forbes YouTube channel.
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