Side Hustle Pro

Nicaila Matthews Okome launched Side Hustle Pro in 2016 as the first podcast to specifically spotlight Black women entrepreneurs who scaled side projects into full-fledged businesses. Ten years and over 500 episodes later, the show has earned a 4.7-star rating from nearly 1,800 reviews and publishes new episodes weekly with no signs of slowing down. The premise is practical and specific. Okome interviews women who started businesses while holding down day jobs, then figured out when and how to make the leap to full-time entrepreneurship. Guests have included Myleik Teele, founder of curlBOX, Morgan DeBaun of Blavity, and Tiffany 'The Budgetnista' Aliche. Each conversation digs into the actual mechanics of getting started: how they funded their first product run, where they found their initial customers, what they wish they'd done differently in year one, and how they managed the transition from employee to founder. The show's strength is its specificity. Rather than broad motivational advice, Okome asks pointed questions about revenue, pricing, marketing channels, and the emotional reality of building something from nothing. A recent episode covered her own 12-week reset across health, money, and business operations, which shows the kind of behind-the-scenes honesty that separates this podcast from aspirational content that glosses over the hard parts. Side Hustle Pro is particularly valuable for anyone who wants to start a business but can't afford to quit their job first. The guests have all navigated that exact tension, and their stories provide a realistic roadmap for building something on the side before going all in.