Bethany Krueger

Investing in Her

by Tammy Pearson and Bethany Krueger

Since 2021, Prouty Project has sponsored a film at the Twin Cities Film Fest. October 2023 was no exception. We had a wonderful evening viewing the documentary Show Her the Money with 150 clients, friends, and supporters in attendance. To top it off, we got the chance to sit down with both Catherine Gray (producer) and Ky Dickens (director and producer) to learn more about their journeys to create this incredible film.
Quick! You’ve got a pile of money at your disposal, and it can’t go into your own bank account. You have to commit it to something. What would you do? Where will these funds go?
Catherine Gray, founder of She Angel Investors, would like you to invest in women entrepreneurs, through women-led venture capital funds. In fact, her passion for closing the gap in the investment world is what inspired Gray to pursue the production of the documentary Show Her the Money.
The Prouty Team on the Red Carpet!

The Prouty Team on the Red Carpet!

The documentary follows four women entrepreneurs as they journey through the ups and downs of building their businesses in the hopes of becoming a billion-dollar company – a unicorn. In the film, these visionaries turn to female funders and angel investors to help them achieve their dreams. The audience soon learns these female funders and angel investors are trailblazers in their own right as only 22% of angel investors are women, and only 2% of venture capital goes to women entrepreneurs. According to Gray, matching up the well-resourced investor to the savvy woman-led business founder could be the start of a lucrative partnership, innovative product, and a shift in the already played out venture capital paradigm.
Despite the film having captured Best Documentary at its first three film festivals in October 2023 (Philadelphia, Twin Cities, Los Angeles), it has been a process that has taken Catherine 10 years to build, knowing interest, people, and outcomes would follow. Finding a director similarly passionate for the project in Ky Dickens proved to be a pivotal piece of the puzzle.
Ky signed on to the project as producer and director, knowing she’d have to “work now” and get paid later. When asked what the toughest part in making Show Her the Money was, Ky vulnerably shared, “My own prejudices around the world of financing. I have been impact-orientated in my pursuits and felt uncomfortable around the idea of anyone striving to make money. I realized that my issues plague women in general. We have a different relationship with money than men do. I had to figure out how to make the subjects and the topic relatable, so I could reach the multitudes of women out there who had the same prejudices around money as I did. For women founders – it’s not shameful to ask for money, and for women investors, it’s not dirty to strive for it. Not only can these new innovative products change the world, so can women reinvesting in other women. It’s powerful.”
Turns out, Catherine and Ky are living out their own version of Show Her the Money, as they embark on a 50-city nationwide tour this year, not only creating publicity for the film, but in hopes of engaging communities in discussions around women entrepreneurs and venture capitalism. Many may not realize their own ability to invest, and it is Catherine and Ky’s goal to start these conversations in hopes of helping others achieve their dreams.
Oh, and remember that large sum of money that you needed to figure out what to do with? Any ideas yet?!
Photos by Dallas Smith @ Twin Cities Film Fest 2023

A Big Thanks To…

TCFF Founder and Executive Director, Jatin Setia for introducing us to Catherine and Ky, and for putting on another fantastic film fest. For more information on the festival, check out
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Catherine Gray and Ky Dickens for sharing their great work and spending extra time with us during their time in Minneapolis. If you’d like Show Her the Money to visit your city, visit:




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