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  • Writer's pictureCreative Return


Meet Sydney Montgomery, the CEO and Founder of Outline It.

Outline It uses AI and machine learning to assist users in creating compelling writing and crafting ideas.

Additionally, Sydney is the Executive Director and Founder of Barrier Breakers. This non-profit increases access to higher education for minority students.

“I want to use our platform to help bridge the gap in education, which means that it has to end up in the hands of students that need it.” — Sydney Montgomery [0:14:12]

Sydney shares her stories of assisting first-generation minority students with acceptance into post-secondary and law school. She explains how this experience inspired her to create Outline It.

We discuss bridging the equity gap in education and how access to education is not always based on merit. Sydney dives into the nuance of raising capital as a black woman. She also recalls her experience growing up in a military family.

“I do not think I should have to hide my ‘why’ when [investors] ask about the story behind the product.” — Sydney Montgomery [0:25:03]

Our conversation unpacks the challenges of diversity and inclusion in the workplace and society. We then explore potential solutions that businesses and individuals can install in their daily lives.

Join us as Sydney shares her expertise in utilizing technology to enhance writing and education. Her dedication to breaking down barriers for all is inspiring! Thanks for listening to this episode.


  • Background about Sydney and the vital work she is doing.

  • Find out more about Outline It and how the company is leveraging AI to help students.

  • How her academic journey inspired her to start Outline It.

  • Hear how she funded Outline It and what the company has planned for the future.

  • Sydney shares the challenges of raising capital as a Black entrepreneur.

  • We unpack the problems minority students have accessing educational technology.

  • She shares advice and insights for young entrepreneurs.

  • Her experience growing up in a military family and how it influenced her values.

  • Bridging the equity gap in education and how it relates to opportunity.

  • The lessons from her educational and entrepreneurial journey.


Please note that the information contained in this interview is not financial advice but for entertainment purposes. I am not a financial advisor and make no warranties or representations concerning the accuracy or suitability of the information contained in this interview. I recommend that any and all investment decisions be made with the advice of accredited investment advisors.


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