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Why is Delegating So Hard? with Valerie Riley and Jennifer Loren

Companies don't scale unless we take the time to delegate. We also know that teams don't grow unless give them the opportunity to take on challenging projects.

But even when we know delegating leads to productivity and developing employees, it's often hard to do because it requires us to trust others. Trust doesn't come naturally to everyone. It's also hard to build trust when you are already overloaded and overwhelmed.

To help us understand why delegating is so hard, we invited Valerie Riley, CEO of LifeSquire, an assistant resource company, offering job placements, outsourced personal & virtual assistants as well as assistant training. Join us as we talk to Valerie about how we can get better at trusting others and ourselves as we grow our companies and learn to let go of control. Special thanks to VEST Member Jennifer Loren, Executive Director of the Cherokee Film Office for moderating this session.

Available on Spotify, Apple and Google Podcast.

Full Transcribe Below

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About Valerie

Valerie Riley was raised in the San Francisco Bay area before moving to Dallas,

TX on a whim. While in Dallas, she took a position as a Personal Assistant.

During her seven years with her employer, she gained the skills that would later

shape her own company. When the position ended, Riley decided to launch her

own business using the skills she had perfected and position she had come to

love, but with an eye to be a disruptor in the field.

She moved to Oklahoma City, OK in 2009, opened what was then called The

Riley Group, and after bringing on three clients in her new home city, hired her

first employee. In 2014 at the urging of her business mentor, Riley began the

process to franchise the concept. After rebranding the company to be called

LifeSquire (and way too many conference calls with consultants and lawyers), the

company was franchised in June 2015. LifeSquire is the largest personal

assistant company in the US and the first to market a personal assistant


Valerie Riley is passionate about her dogs, her vacuum, empowering caretakers,

and new ideas. In that order

Connect with Valerie:

About Jennifer Loren

Jennifer Loren is an Emmy-award winning filmmaker and the director of Cherokee Nation Film Office. Evolving from an investigative reporter and producer to a documentarian and host, she has been in the television and film industries since 2001. Jennifer started her career in television news where she moved around the country as an anchor, producer and investigative reporter, ultimately landing at home in Tulsa, Oklahoma. In 2014, she joined Cherokee Nation Businesses where she co-created the highly acclaimed documentary-style show Osiyo, Voices of the Cherokee People. Jennifer is the executive producer, host and show-runner of the docuseries, which is often called OsiyoTV. She also produces and directs many of the short documentaries in the show. A proud citizen of the Cherokee Nation, Jennifer is humbled and thrilled to share her tribe’s stories with the world.

In 2019, Jennifer helped to create and roll out the Cherokee Nation Film Office and now serves as its director. A first-of-its kind endeavor by a tribal nation, the mission of the Cherokee Nation Film Office is to increase the presence of Native Americans in every level of the film and television industries, while creating opportunities for economic development and jobs in the Cherokee Nation. Also in 2019, she was named a Woman of the Year, Pinnacle Award winner by the Tulsa Mayor’s Commission on the Status of Women and the Tulsa YWCA.

Jennifer has been nominated for more than 30 Emmy awards and has been awarded ten of those; nine as Executive Producer and Host of Osiyo, Voices of the Cherokee People and one for investigative news coverage in 2012. Jennifer has won several AVA Digital Gold and Telly Awards, also for her work on OsiyoTV, and the show has been the recipient of several other awards, including the Association for Women in Communications’ 2016 and 2017 Clarion Awards. During her time in news, Jennifer won several awards for investigative reporting, including a Society of Environmental Journalists’ award and the prestigious Oklahoma Society of Professional Journalists’ First Amendment Award. While all of the accolades are validating, Jennifer says the most rewarding part of her job is working with and learning from citizens of the Cherokee Nation.

Jennifer’s favorite job of all is as a wife and mother. She has two daughters who keep her busy with after school activities and Jennifer volunteers with their PTA and school foundations, and serves on multiple other Boards in the Tulsa and Oklahoma communities.Jennifer is a graduate of the Gaylord College of Journalism at the University of Oklahoma and an active member of the Native American Journalists Association and Society of Environmental Journalists.

Connect with Jennifer:


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