Season 2

With life-changing investments on the line, a new group of female entrepreneurs pitch their businesses in hopes of earning mentorship from investors Ashley Graham (Knix, Bobbie, Partake Foods) and Emma Grede (Good American, Skims, Safely). Only a select few will move forward, so the competition is fierce to determine which founders have what it takes to transform their side hustle into their main hustle and launch the next multi-million-dollar company.

The Side Hustlers meet with investors Ashley Graham and Emma Grede, hoping to prove their businesses’ potential and secure mentorship. Emma grows frustrated with one of her entrepreneur’s lack of truthfulness surrounding their business, causing her mentorship to be at risk. After analyzing the numbers, Ashley faces a tough decision when it comes to the future of working with one of her founders.

With one Hustler already eliminated from mentorship, the investors turn their focus to customer outreach, as they tighten the screws on the remaining group of founders to see who will crack under the pressure. Tensions run high as Emma demands one team to trash their business plan, while another founder stresses over telling her boss about her side hustle. After hearing from potential customers, one founder struggles to face the fact that her businesses’ branding is not tracking with the public.

With the final pitches around the corner, the Side Hustlers host a marketing event to promote their businesses and prove their potential for growth. Some founders exceed expectations while others miss the mark, creating doubts in the minds of their mentors. With stakes at an all-time high, Ashley and Emma have a surprise for one Hustler, and another must cancel their marketing event because their business is not ready for promotion.

With the final pitch days away, the Hustlers feverishly prepare for the opportunity to earn a potentially life-changing investment from Emma Grede and Ashley Graham. Some Hustlers wrestle with telling their bosses—and their families—about leaving their day jobs, while others must scramble to create a pitch from scratch featuring a brand-new slate of products. Which entrepreneurs will prove they have what it takes to propel their business forward and turn their side hustle into their main hustle?