The documentary Show Her The Money, directed by Ky Dickens and produced by Catherine Gray, aims to bring awareness to the gender funding gap in the world of venture capital and entrepreneurship, and inspire change. Through personal stories and powerful testimonies, the film explores the challenges women face in securing funding for their startups and offers hope for a more equitable future.

Trailer for the documentary Show Her The Money.

A Journey into Gender Disparity

Show Her The Money addresses the deeply frustrating reality that only a small percentage of venture capital funding goes to female-led startups. This issue reflects broader systemic biases in the investment landscape. The film seeks to start a crucial conversation about these challenges and potential solutions.

Ky Dickens, an award-winning filmmaker known for works like “#TimeToCare” and “Zero Weeks,” directs the documentary. Catherine Gray, the executive producer, is also the founder of She Angel Investors and co-founder of the non-profit She Angels Foundation. Her passion for supporting women in business is palpable throughout the film and its promotion.

Cast members of Show Her the Money

Making products women need

The film features a cast of successful women entrepreneurs and investors. Among them is Jasmine Jones. Jones is the founder and CEO of Myya, an online direct-to-consumer, insurance-billable post-mastectomy intimates brand.

Jones created Myya in response to her grandmother’s experience with breast cancer, aiming to provide well-fitting post-mastectomy bras. The company offers virtual fittings and can bill insurance directly for its products. Jones’ journey exemplifies the challenges and triumphs highlighted in the documentary. In April 2022, Cherry Blossom Intimates, which incubated Myya, secured a $2.25 million pre-seed round. This made Jones one of the few Black women to raise over $1 million in venture funding, bucking the funding disparities trend addressed in the film.

Ky Dickens (left) with Catherine Gray.

The faces behind the film

Marcia Dawood, an angel investor and associate producer of the film, offers valuable insights into the investment landscape. As a member of the SEC Small Business Capital Formation Advisory Committee and Chair Emeritus of the Angel Capital Association, Dawood underscores the film’s mission: “This is more than just a film — it’s a movement to change how much funding goes to women, people of color, and any underrepresented founder striving to make a meaningful impact in the world.” Wendy Ryan, CEO of Kadabra and a featured cast member, brings her expertise in leadership and organizational development to the film. She explains: “I saw the film’s potential to raise awareness about these disparities and motivate people to take action. This issue affects everyone, because who gets funded determines the kinds of products and services we all end up using and benefiting from.”

Challenges and solutions

One of the most critical challenges for startups is crossing the “valley of death” — the difficult early phase between initial funding and achieving sustainable growth. This stage is especially challenging for female founders. Ryan points out: “Even when female-led companies secure early funding, like in the seed stage or Series A, they often struggle more than their male counterparts to secure additional funding in later rounds, such as Series B or C.”

Dawood emphasizes the importance of engaging investors early in the process: “I understand that entrepreneurs often hesitate to do this. They might think, ‘I know my product is going to be great, so I’ll wait until it’s perfect before showing it to anyone.’ But, in my opinion, that’s the wrong approach. It’s crucial to engage potential investors along the way, allowing them to witness your progress and get to know you.”

Sharon Gless in Show Her the Money

Both Dawood and Ryan acknowledge that barriers to entry persist, particularly psychological ones. Ryan elaborates: “I think that’s a significant part of the issue. Women often feel they need to be overqualified to apply for a job or promotion, and I believe that mindset carries over into areas like angel investing. Many women think, ‘I can’t be an angel investor because I don’t know enough about it,’ or ‘I need to take more classes before I feel qualified to make such decisions.’ Others might question, ‘Who am I to put my family’s money at risk in this way?’”

Pocket Sun of SoGal Ventures

Impact and reception

Show Her The Money has been screened in over 50 cities worldwide. Dawood shares: “We’ll continue screenings through the fall, and by October, we expect to be in well over 50 cities. The film is truly becoming global.”

The documentary has sparked important conversations about venture capital and startup funding. Dawood notes: “Many people are surprised to learn about the realities of venture capital. A lot of them don’t even fully understand what venture capital is, or how to secure startup funding, or what it takes to get a company off the ground.” A call for change As Show Her the Money continues its screenings, its goal is not just to highlight disparities but to inspire meaningful action. By exposing the persistent funding gap for women entrepreneurs and presenting potential solutions, the documentary aims to be a catalyst for real change in the investment landscape.

Dawood emphasizes: “The film is meant to bring together different ideas and start crucial conversations about these issues.”