In the offices of Black Bicycle Entertainment, there’s a wall of black-and-white photos of celebrities riding around on bicycles, with the likes of Jennifer Aniston, Albert Einstein and Kermit the Frog all racing around fun and fancy free.

“It’s a very diverse wall,” laughs Erika Olde, the company’s CEO of the inspiration behind the company’s name. “It was an ode to the Golden Age of Hollywood when the studio system was very much in play and actors would be on backlots and you were there all day and riding bicycles around and [the name] was just a novel nod to that time period because I’m very nostalgic.”

Still, nostalgia has its limits for Olde, who may specialize in old fashioned crowdpleasers, but is quietly revolutionizing who gets to make them. A proud Canadian who once saw movies as an escape to worlds away from where she grew up, Olde is now flipping the script, expanding Hollywood’s perspective with a number of high-profile, female-driven productions and contributing to diversifying opportunities to break into the industry through her work at the Ghetto Film School. This weekend alone marks a major milestone for the company, seeing Black Bicycle’s first wide release with the Hallie Shyer-Meyers comedy “Home Again,” starring Reese Witherspoon, in thousands of theaters across the U.S. while Olde will be traveling to Toronto for the premiere of “Woman Walks Ahead,” a Jessica Chastain-led drama from Susanna White. While Olde wouldn’t be a good producer if she wasn’t gifted at making tough schedules work, even she didn’t foresee such a confluence of events.

“This is my first film at TIFF, so that means a lot to me and being a ‘ShareHerJourney’ ambassador, I feel incredibly lucky,” says Olde. “Lots of us talk in the office like someone is really watching over us because this just doesn’t happen this quickly, nor does it happen all at once like this.”

Yet Olde’s been laying the groundwork for this moment for quite some time. With a father who worked in the financial services industry, an innate sense of analytics and logistics guided Olde towards marketing rather than film school, but have made her a particularly shrewd producer without the baggage of thinking there’s a certain way things should be done. Such outside the box thinking led her not to flinch when Whitney Cummings approached her with a wild idea to adapt Louann Brizeldine’s nonfiction study of female psychology “The Female Brain” into an ensemble comedy for her feature debut, and she’s steadily been optioning the kind of prestige material that Hollywood has all but abandoned such as a Tammany Hall-set drama “An Extraordinary Man” and a biopic of Planned Parenthood founder Margaret Sanger, while having the wherewithal to put three films into production in the last 18 months with just a six-person staff.

“The thing I always said to people is I am never going to be the reason why a movie that I have doesn’t get made if I can possibly help it,” says Olde, who had that put to the test last year when she organized back-to-back-to-back shoots for “Female Brain,” “Woman Walks Ahead,” “Home Again” from June to November of 2016. “I didn’t want to say, ‘Oh we can’t do this project because of another project we’re doing,’ so we made three of them because we could and they were ready to go.”

The films weren’t only of their moment as far as production goes, but feel as if they could only be made now. “Woman Walks Ahead” takes a tale about the Old West in a new direction with a portrait of Catherine Weldon (Chastain), a New York artist who became a confidant to Sitting Bull (Michael Greyeyes), while even “Home Again,” which harkens back to the pleasures of its director’s mother Nancy’s work, could be called a romantic comedy in which the chief romance comes from a freshly divorced mother of two (Reese Witherspoon) falling back in love with herself as a trio of young filmmakers crash on her couch (Jon Rudnitsky, Pico Alexander and Nat Wolff). They feel unexpected precisely because they take familiar genres and deconstruct them from an entirely new angle.

“I look for very realistic relationship dynamics, realistic topics,” says Olde. “My biggest thing about the story is [that] I think people go to the movies not only be inspired, but to learn something – at least, that’s why I want to go – and to have a situation be presented that gives us a broader perspective on something.”

Olde’s own horizons have been broadened by working alongside industry veterans on the films such as “Legends of the Fall”’s Ed Zwick and Marshall Herskovitz on “Woman Walks Ahead” and Nancy Meyers, with whom co-producing “Home Again” was a dream come true. (“They raised me cinematically,” says Olde. “The thing is when you’re in the moment, you’re not necessarily thinking that way about it, but when you reflect, ‘You’re like holy crap I’m making a movie with the woman that made “The Parent Trap,” that I watched 10,000 times as a child, and realize this is a little bit nuts.”) And she has paid it forward with her work with the Ghetto Film School, the nonprofit mentorship program with campuses in Los Angeles and New York to bring students from underserved communities into the entertainment industry.

In 2016, Olde saw an opportunity to start a speaker series for the school, drawing on her own Rolodex to encourage young women looking to get their start in filmmaking and pitched Ghetto Film School founder Joe Hall. The “Iris-In” program, as it’s come to be known, has grown so successful that it’s spread across the Ghetto Film School campuses on both coasts after starting in New York. Additionally, Olde has actively sought out ways for the program to evolve, as the Ghetto Film School has come to open the series up to all their students, regardless of gender and Black Bicycle will soon open up a mentorship program within its own walls for five female graduates to get hands-on industry experience.

“I personally feel that we have a duty to leave a lasting impact on the world, and that everybody in any industry or position can reach the level in their work where they can make things possible for others and teach others, then that’s our responsibility to the next generation,” says Olde. “When I started in the business, I had been asked often if I had been to film school and I had not, but I was quickly assured that was not [a bad thing]. Most people that I’ve spoken to that had been to film school would tell me that they learned a lot about theory and the art of making a film, but you learn very little about how the industry runs. And that was the biggest learning curve for me, coming into this business, so I thought it just makes sense that someone should have a program that allows for people actively in the business to come in and teach students about how it works.”

Being of the belief that people find the positions that are right for them, Olde sees the mentorships as a way for aspiring filmmakers to discover where their passion and skill set meet, just as it did for her. And Olde is planning to assist these students well after they’ve gone through the mentorships, placing them in internships where they’re suited to the specific demands of a given production or sales company.

For an industry that’s slow to change, Olde has done all this in a remarkably short period of time and like her movies, her own story comes with a twist, as she entered the film business without ever intending to become such an outspoken advocate for equality. In fact, she didn’t even take note that all of her most recent films have been directed by women until recently, a coincidence that occurred simply because she picked the projects that looked most promising to her.

“It really only occurred to me after I was looking at our slate and I love the fact that it was organic,” says Olde. “Sometimes one needs to let their purpose find them and I definitely will continue to support female filmmakers. It really makes a huge difference when you know you’re doing something that you love, but also doing a greater good.”

“Home Again” opens wide on September 8th and “Woman Walks Ahead” will premiere at the Toronto Film Festival on September 10th at Roy Thomson Hall at 9:30 pm.