How to Start a Streetwear Fashion Business Ft. Jaywalking | Ep 01 | OLS with Adhunika Singh

What does it really take to turn your name into a brand—and your brand into a movement? In this episode, I sit down with Jay, the creative force behind streetwear label Jaywalking. From being a college dropout to building one of India’s most loved fashion labels, Jay opens up about the messy middle of his journey—dropping out, starting late, and finding clarity (and courage) along the way. We talk about personal growth, business basics, and why self-belief is the real secret to success! ___ In this episode: (00:00) – COMING UP (01:21) – GUEST INTRO & JAYWALKING ORIGINS Meet the mind behind India's cult streetwear brand (03:07) – SELF-DISCOVERY & LIFE PHILOSOPHY What genre is your life right now? (04:26) – CHILDHOOD & BACKGROUND Raised in Canada, shaped by simplicity—his early years weren’t ordinary. (07:29) – EDUCATION & DROPPING OUT He dropped out of multiple schools—and doesn’t regret a thing (09:03) – RECOGNITION & FAMILY The only validation he really wanted (11:16) – GENERATIONAL PRESSURES & COURAGE The problem with Gen Z nobody talks about (12:13) – STARTING JAYWALKING AT 26 He waited. He hesitated. Then something shifted. (14:09) – FRIENDSHIPS & GROWTH If your friends aren’t growing with you, hear this (15:22) – FAMILY BUSINESS VS PERSONAL VISION Why he walked away from a ready-made empire (17:05) – BUSINESS BUILDING BASICS Forget intention. Do you have skill? (19:01) – PERSONAL STYLE & BRAND IDENTITY Don’t fake your vibe—customers can tell (20:33) – NAME, VALUE, OR WEALTH? He didn’t want to get rich—he wanted to get known (22:25) – SPIRITUALITY & INFORMATION OVERLOAD Is knowing less the real superpower? (24:10) – DEFINING WEALTH After the dream car and sea-facing apartment… then what? (25:49) – MENTAL HEALTH & SELF-AWARENESS When your mind turns against you—this is what you do (27:08) – BRAND SIGNALING & ASPIRATION What people are really buying when they buy Jaywalking (32:08) – T-SHIRT LAUNCH & SCALING How a simple T-shirt changed everything (36:18) –