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In this episode of How I Got Here, Dreena welcomes Jessica Myers, an entrepreneur, real estate developer and investor, and one of the youngest black hotel owners in the hospitality industry. From dreaming of being a TV news anchor to realizing her passion for real estate, Jessica has always wanted to make an impact on as many people as she can and she’s here to tell you how she’s doing it.
Jessica speaks on how her education in journalism and participation in several work experience programs, including her roles at Fox News and The Nick Cannon Show, shaped her journey to becoming a real estate investor and hotel owner. She also breaks down what real estate wholesaling is, how it helped her break free from her corporate career, and how she co-created the Epic Collective as a platform to network and educate others on the freedom of working in real estate.
“My dad was like, “You spent so much time climbing up the corporate ladder, what if the ladder is on the wrong wall?” and that enlightenment is what started the trajectory of fulfillment, of purpose, ownership, and really connecting with my dreams.” - Jessica Myers
Stay tuned to learn how to overcome fear and failure to develop a successful track record in real estate investment and development, along with the power of working because you want to, not because you have to. Plus, Jessica shares insight into her future community development endeavors and how her hotel business has been impacted by the covid-19 pandemic.
“The more you surround yourself with people who know how to navigate tough situations, the better and more secure you feel.”- Jessica Myers
Connect with Jessica:
Visit her website: www.wholesalertohotelowner.com
Follow her on Instagram: www.instagram.com/itsjessicamyers
Connect with her on Facebook: www.facebook.com/itsJessicaMyers33
Connect with her on LinkedIn: www.linkedin.com/in/jessicatipton
Resources:
The Emma Bowen Foundation: www.emmabowenfoundation.com
International Radio and Television Society: www.irtsfoundation.org
Course: From Wholesaler to Hotel Owner: www.wholesalertohotelowner.com
Epic Collective: www.epiccollective.com
About the Host:
Dreena Whitfield has a proven ability to create tangible outcomes that helps clients exceed expectations. Her diverse career has led her to spearhead the communications and marketing efforts for leaders in the nonprofit, corporate and political sectors, as well as small businesses internationally.
With more than a decade of experience, Dreena and the WhitPR team have a proven ability to spot opportunities for our clients to grow their brand recognition in saturated markets that are in alignment with their overall objectives.
The Huffington Post listed Dreena as one of their “Top 25 African American Millennials in PR to Watch.”
Follow Dreena & WhitPR on all the socials:
@Dreenawhitpr & @whitpr
Join The WhitPR Collective: www.whitprcollective.com
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howigotherewdreenaw.substack.com
Creators and Guests
Host
Dreena Whitfield
Dreena Whitfield-Brown is the Founder and CEO of WhitPR, an integrated strategic communications agency with 15+ years serving clients in the nonprofit, corporate, and political sectors. Recognized as one of PRWeek's 40 Under 40, a PR News Top Woman in PR, and named to Inc.'s 2025 Female Founders 500 List. She created How I Got Here to have the raw, honest conversations about entrepreneurship that nobody has on the record.
What is How I Got Here with Dreena Whitfield?
How I Got Here with Dreena Whitfield goes beyond the highlight reel with Black women founders, executives, and leaders. Real conversations about the pivots, the setbacks, and the purpose behind the work. From bootstrapping a beauty brand with $500 to leading a professional sports franchise, each episode explores the moments that shaped who they became and the cost of building something meaningful.
For women navigating leadership, business ownership, career reinvention, and the cost of ambition.
New episodes biweekly on Wednesdays.
Host: Dreena Whitfield
Executive Producer, Writer & Creative Director: Keena Williams / Struxa
howigotherewdreenaw.substack.com