Business-minded solutions to legal problems.
We believe that applying business principles to the delivery of legal services provides the greatest benefit to our clients. We conduct cost-benefit analysis at each step of the litigation process.
Meet the team
To view the staff profiles, click on the individual’s photo below.
Amy E. CuykendallAttorney
Stephanie WeissOffice Manager & Paralegal
Former Banker Turned Trial Lawyer
Ben has litigated lawsuits involving business partnerships and shareholder disputes, business purchase and sale related litigation, title insurance claims, civil theft, foreclosure, lender lawsuits, real estate transactions gone wrong, final judgment collection cases, employment contract litigation, slander, and commercial lease lawsuits.
Ben’s Unique Banking Background
Before becoming an attorney, Ben spent the majority of his professional career as an investment banker, mortgage banker, and professional loan buyer, purchasing mortgage loans from other banks. Ben’s prior banking career also included managing hundreds of foreclosure cases on behalf of Ocwen Financial. Ben’s unique banking background makes him an undeniable authority, well-prepared to render advice and to litigate mortgage loan issues.
During his former career as a banker, Ben conducted loan purchase due diligence on tens of billions of dollars of loan purchase transactions. He has worked for Ocwen, Lehman Brothers, Goldman Sachs, Countrywide, Wells Fargo and many other institutional lenders. More specifically, Ben conducted loan purchase due diligence, negotiated loan purchase and sale contracts, and developed loan purchase pricing models and bidding strategies. In Ben’s loan acquisitions consulting practice, he was often hired by the buyer bank to review loan files to determine if the seller bank actually followed their own lending standards. Finally, Ben has been through Countrywide’s forensic loan fraud training.
Additionally, Ben maintains a Florida real estate broker’s license and is a former Florida licensed real estate appraiser and former title agent.
Ben holds a Juris Doctor degree, with an emphasis on Mergers & Acquisitions, Corporate Bankruptcy, and Corporate Restructuring from Stetson University College of Law, as well as a Master’s of Business Administration (MBA). He also holds a Bachelor of Science (B.S.) degree in Business Management from Palm Beach Atlantic College, where he graduated Cum Laude.
Outside of the office, Ben’s interests are as well-rounded as his background. He is an avid angler, loves the outdoors, the shooting sports, weight training, and chess. He is also a former open division beach volleyball player and is rusty, but trained in ballroom dancing.
Amy E. Cuykendall
Amy graduated from Stetson University College of Law and became licensed to practice law in April 2005. She opened McRae & Metcalf’s Tampa office and clerked there until moving on to Englander & Fischer, P.A., in 2003. She was later promoted to Associate and then to Shareholder in 2008. From 2009-2012, Amy owned her own company, Core Care Patient Advocates, and is a 2010 graduate of Leadership St. Pete.
Starting in 2003, Amy completed both legal and nonlegal pro bono volunteer work at Community Action Stops Abuse (CASA), and then served nine years on the Board of Directors, including service as President from 2009-2011. She also served as Chair of the housing committee, which founded the new 100-bed shelter that opened in Summer 2015.
In 2010, Amy was awarded St. Petersburg’s Young Professional of the Year and was inducted into the Florida Association for Women Lawyers 2011 Class of Leaders in the Law. Amy Cuykendall has worked for Castle Law Group, P.A., since 2010 and became a partner in Hillard Cuykendall, P.A. when it was formed in 2014.
Amy has vast litigation experience, having conducted multiple trials and several hundred hearings in business and real estate litigations. In her spare time, she enjoys living in St.Petersburg, doing hot yoga, cooking, and spending time with family and friends and her dog, Mabel.
Office Manager and Paralegal
Outside of work, Stephanie oversees Children’s Ministry at her church. She loves working with kids and spending time with her family and friends.
lived in Florida for most of her life. She is fluent in Spanish. Her experience of nearly 20 years in customer service, along with her bi-cultural background, has made her a wonderful addition to Hillard Cuykendall, P.A.
As our file retention specialist, she appropriately closes each case to comply with legal requirements for file retention. She joined the firm in 2016.
Outside of the office, Lorena enjoys going to church, taking her three children to soccer practice, and spending time and family and friends.
Whether you need legal advice on the best way to organize your new business venture, need help drafting or reviewing business contracts or need to sue or are being sued relative to your business, your Pinellas lawyers at Hillard Cuykendall, P.A. are here to help.