Sylvester grew up in Kent, Washington as part of a migration of from Seattle that exposed people of color from the city to rural communities were starved for resources and opportunities. The schools were ill-equipped to handle the influx of youth struggling to adapt. Not to be deterred, Sylvester finished high school and completed an engineering degree at the University of Washington. With engineering jobs scarce at the time, Sylvester began a career in commercial real estate valuation, earning his General Certified Appraiser license in 2007. He dabbled in politics and retained his focus on issues related to uplifting black and brown children. Sylvester helped launch a task force whose sole purpose was to pull together developers, business leaders, and stakeholders to improve access to affordable housing.
Currently, CG Real Estate has one project underway and others in the pipeline. Sylvester lives in North Seattle with his wife, Ellen, and daughter, Vivian.