About Us
John Cunningham
Born and raised in San Diego, John has always had a passion for real estate that began when he was just eight years old. Growing up in a family of entrepreneurs, he developed a keen understanding of property and business at an early age. With a relentless drive and deep-rooted connection to his hometown, he went on to pursue a degree in business with a focus on finance at the University of San Diego, where he honed his expertise in both financial strategy and market trends.
Before founding La Playa Property Management, John built a successful appraisal firm, gaining valuable insights into the true value of properties. His commitment to excellence in real estate led him to become a licensed broker and contractor, allowing him to offer a comprehensive range of services to clients. La Playa Property Management is a small, family-run business where he combines his in-depth knowledge of the industry with a personal touch, always treating every client like family.
Whether you’re looking to lease, manage, or invest, John is dedicated to providing exceptional service backed by years of experience and a passion for helping clients make the most of their real estate investments.
Tom Cunningham
In 1982, after a career in the United States Navy, Tom joined World Savings and Loan as a loan officer making loans on single-family homes in San Diego County. In 1984, World Savings opened a commercial loan organization in many of the major cities of the United States and selected Tom Cunningham to originate major loans on apartment buildings and commercial properties in San Diego. Over the next eight years, Tom was among the top three producers of commercial loans in the United States.
In the early 1990s Tom was selected to lead a workout group formed to manage increasing number of foreclosures among world savings loans. This task involved the management, rehab, and sale of foreclose properties (mostly apartment buildings). Tom was responsible for management of nearly 2000 apartment units throughout the United States.
In order to reduce the number of defaults in world savings portfolio, Tom instituted an option for selected apartment owners in default to use the rental income from their properties to rehab and re-rent any vacancies in their buildings until the properties were able to cash flow a new loan could be put on the property, which would be acceptable to both the lender and borrower. Tom’s experience in dealing with owners during his years at World Savings have proven to be invaluable.
Tom acquired his own portfolio of real estate in San Diego and other locals. Tom is excited to be part of the La Playa Property Management team and be part of a dedicated group of individuals and make a difference in our community.
La Playa Property Management Managers
Anna Amano
Alyssa Lehman
Julie Finlay
Anna was born and raised in San Diego and knows the city in and out. After working as a Legal Contract Administrator for years, Anna transitioned into property management in 2015, working at RJW Properties. Over the ten years at RJW Properties, Anna became very knowledgeable and experienced with all aspects of property management and the
Anna was born and raised in San Diego and knows the city in and out. After working as a Legal Contract Administrator for years, Anna transitioned into property management in 2015, working at RJW Properties. Over the ten years at RJW Properties, Anna became very knowledgeable and experienced with all aspects of property management and the multi-family business. Anna was the office manager, and in charge of human resources, worker’s comp insurance, training onsite managers, and all legal issues. She supervised over twenty onsite managers and oversaw seven hundred units. Anna was heavily involved in recovering unpaid rent during Covid, by working with the city and county submitting emergency rental assistance applications for the tenants. Anna has managed renovation projects on a very large scale, namely apartment buildings. It was there that Anna connected with Tom & John Cunningham and started managing all of their properties. Over the years, Anna worked with the Cunninghams on numerous projects and acquisitions.
Anna has exceptional leadership and communication skills and a proven track record of improving occupancy rates and resident retention. She has extensive knowledge of federal regulations and landlord-tenant laws and is very resourceful with her legal background.
Julie Finlay
Alyssa Lehman
Julie Finlay
Raised in San Diego, Julie's career began with 10+ years in the insurance industry, where she gained a thorough understanding of risk management, customer service, and problem-solving—all of which have proven to be invaluable skills in property management.
For over 30 years, Julie has maintained a close friendship and professional relatio
Raised in San Diego, Julie's career began with 10+ years in the insurance industry, where she gained a thorough understanding of risk management, customer service, and problem-solving—all of which have proven to be invaluable skills in property management.
For over 30 years, Julie has maintained a close friendship and professional relationship with Anna, a fellow property manager. Their shared commitment to providing exceptional service led them to work together at another property management company for several years.
Now, as part of the team at La Playa Property Management, Julie brings a unique combination of experience in insurance and property management. Currently working on obtaining her real estate license, Julie is excited to expand her expertise and continue offering top-tier service to property owners and tenants alike.
Her dedication to her craft, paired with her friendly, approachable demeanor, makes her a trusted asset to both property owners and residents in the San Diego area.
Alyssa Lehman
Alyssa Lehman
Alyssa Lehman
Originally from Ohio, Alyssa made the move to San Diego in 2020, quickly falling in love with the vibrant culture and endless opportunities that California has to offer. A tenant of La Playa Property Management for some time, Alyssa's journey with the company took a natural turn when she joined the team in late 2024.
Alyssa holds a bachel
Originally from Ohio, Alyssa made the move to San Diego in 2020, quickly falling in love with the vibrant culture and endless opportunities that California has to offer. A tenant of La Playa Property Management for some time, Alyssa's journey with the company took a natural turn when she joined the team in late 2024.
Alyssa holds a bachelor’s degree in healthcare management and brings a diverse professional background to her role. Over the years, she’s worked in various industries, excelling in event planning, vendor coordination, legal regulations, contracting, and project management. This extensive experience has equipped her with a sharp attention to detail, strong organizational skills, and a passion for creating seamless experiences for both property owners and tenants.
Alyssa is deeply involved in the San Diego community. She is a firm believer in the power of building strong, connected neighborhoods. Whether it's organizing community events, addressing tenant concerns, or ensuring properties are well-maintained, Alyssa leads with purpose and dedication. Her energetic and approachable nature makes her an invaluable asset to La Playa Property Management.