About Us

PS27 Foundation provides educational resources to early-stage companies and startups to help them achieve sustainable growth. We deliver training and education through classroom lessons, company site visits, comprehensive mentoring, and distance learning. We are interested in working with all founders, including those who may be disabled, veterans, women, and people of color.

Advanced techniques and equipment are used to enable an environment that promotes learning and collaboration. PS27 Foundation is constantly working to form strategic partnerships with local and national organizations and the government to create jobs and improve the community.

Our Vision

To cultivate a vibrant entrepreneurial ecosystem that drives innovation and impact throughout Jacksonville and the surrounding region.

Board of Directors

Jim Stallings is an internationally recognized business leader, entrepreneur and investor who specializes in launching and scaling early stage companies in areas of technology and ecommerce. Jim is the Founder and CEO of PS27 Ventures and has been involved in starting dozens of new ventures in FinTech, HealthTech and Software as a Service.

He believes innovation should be viewed as the core offensive strategy of any company, "either disrupt or be disrupted". Jim's career spans over 30 years as IBM General Manager of several major lines of business including the company's $7B Linux software business, its intellectual property division with 39,000 patents and its $21B global hardware sales group. He started his business career as a data analyst in the Space Division at GE.  

Jim earned a Bachelor of Science degree from the US Naval Academy and served as a Captain in the US Marine Corps. He is on the Board of Directors at Fidelity National Informations Systems (FIS), and Cannae Holdings, Inc (CNNE).

Annie DeStefano is the Founder and CEO of Ann DeStefano Advisory, a consulting and advisory firm that partners with early and growth stage fintechs, banks and various financial institutions seeking to launch new products, scale partnerships or sharpen their competitive edge. Previously she was Vice President, Partnerships at FIS.

She’s held roles in engineering, product management and operations at venture-backed location intelligence company Foursquare and investment bank Goldman Sachs, as a member of the launch team for the Marcus by Goldman Sachs consumer banking platform.

In 2019, she was named an "Inspiring Fintech Female" by the NYC Fintech Women organization and in 2021, a ’40 Under 40’ recipient by her alma mater, Stevens Institute of Technology. She is active in fundraising for the National Ovarian Cancer Coalition and recently received certification as a habit coach. She served as a member of the Stevens School of Business Board of Advisors and currently sits on the University of North Florida College of Computing, Engineering, and Construction Dean’s Leadership Council.

Caleb Garrett is the Director of Development for the Coggin College of Business at the University of North Florida, where he leads philanthropic strategy and external engagement to advance the college’s mission and regional impact. He partners with alumni, donors, and business leaders to secure transformational support that strengthens the college and the local business community. Prior to his role at Coggin, Caleb led development efforts for UNF’s College of Computing, Engineering & Construction. Earlier in his career, he worked in nonprofit fundraising and served as a public school teacher.

Caleb holds a bachelor’s degree and a Master of Divinity from Palm Beach Atlantic University, as well as a Certificate in Fund Raising Management from Indiana University’s Lilly Family School of Philanthropy. He is actively engaged in the community, serving on the boards of the PS27 Foundation and the Youth Crisis Center, and on the Advisory Council for the Small Business Development Center at UNF. He was recognized as a Jacksonville Business Journal 40 Under 40 honoree in 2025 for his contributions to higher education advancement and the regional business community.

Heather Horovitz Heather combines her 12-plus years of finance and management experience with a passion for community development and outreach. She collaborates with internal teams and outside partners to meet the unique needs of distressed neighborhoods with the mission of improving access to capital for low and medium-income people, contribute to generational wealth building, and driving projects that have positive community outcomes.  

Prior to her time in the financial industry, Heather worked in the food and beverage industry as a chef. She credits her time as an Executive Chef for her ability to manage large teams under stressful conditions. After her time in the kitchen and earning two graduate degrees from Florida International University in Miami, FL, she transitioned to the financial world, working in various finance and operations roles and eventually in corporate development (M&A) and strategic planning. 

Born and raised in the Bahamas, Heather has a unique talent of connecting with people. She leverages her diverse background to engage in the community and develop financial products and programs that are affordable and approachable for all people.

In addition to her professional role, Heather has a passion for serving the community. She is a board member for the North Florida School of Special Education and serves on the Finance Committee. In 2022, Heather was appointed by Mayor Lenny Curry to the Jacksonville Housing Authority as a Commissioner. She chairs both the Acquisition and Finance committees. In this role she advocates for housing inventory and access. She is a member of the Mayors Youth At Work steering committee which works to address workforce development for Jacksonville Youth. 

Heather is a 2023 Jacksonville Business Journal 40 under 40 honoree. 

Heather has a passion for health and wellness. In her free time, she trains for long-distance triathlons and marathons. She enjoys coaching people to reach their fitness as well as professional goals and is an active mentor. She is also a youth athletics coach and enjoys helping student athletes develop technical and personal skills on the field. She is a proud swim and baseball mom.

Laurence Andrews is currently serving as the Coordinator and Business Manager for Santa Fe College’s Center for Innovation and Economic Development (CIED) – a business incubator. Prior to this he was the Program Coordinator for the Bradford County Incubator – a collaborative entrepreneurship training program between the CIED and CareerSource North Central Florida.

The goal of that program was to help local entrepreneurs turn their ideas into income. Laurence has over 20 years of experience analyzing problems and providing strategic and innovative solutions for clients and coworkers in the public and private sectors.

Laurence has an MBA with a focus on Strategy Development and Entrepreneurship from Babson College and an interdisciplinary BS in Business Administration and Music from Alliance University/Nyack College. He also holds Certificates of Completion from the University of St. Gallen Switzerland’s International Study Program (ISP) – a 10-week intensive study exchange program focusing on doing business in continental Europe, the Price-Babson Symposium for Entrepreneurship Educators – a weeklong immersive program focusing on Action-Based teaching methods for entrepreneurship educators and incubator managers, and the International Business Innovation Association (InBIA) in Entrepreneurship Center Management.

Sang Cho is currently the Co-founder, President, and CFO of Rounded, by Concealment Express a manufacturing company, and Co-founder and President of Haymaker Coffee Company both based in Jacksonville, Florida.

Beforehand, he lived in Houston for seven years working with NexTier Inc, formerly Keane Group, working directly with the COO and CFO to build the infrastructure and team to position it for IPO, which went public in 2017. Prior to Keane Group, Sang began his career with GE, progressing through the Financial Management Program and continuing on through their Global leadership program, the Corporate Audit Staff. Through his rotations, he lived and worked in Belgium, Germany, Japan, Norway, and the UK among others.

Sang is a member of the Young Presidents’ Organization (YPO), former Chair, and a Founding Board Member of Bloom Academy, a charter school in Houston, Texas, a graduate of the Leadership Jacksonville Program, a fellow of NetKAL X, and American Leadership Forum of Houston, Texas.

Sang earned a M.P.A. from the John F. Kennedy School of Government at Harvard University, a M.B.A. from the Kellogg School of Management at the Northwestern University, and a Bachelors of Business Administration at University of Miami.

Megan Hayward's entrepreneurial spirit and passion for innovation sparked her desire to transform the outdated processes of blue collar temporary staffing. Her frustration with the status quo motivated her to launch her own staffing agency at a young age, then driven by the belief that the industry was ready for a radical change, she began to create a software platform to allow for a modern approach to an antiquated industry.

Megan founded her first staffing agency at the age of 24 after being a co-founder of another. Her achievements in the industry have earned her a seat on the advisory board of the latter. She is a member of the 2023 class for Leadership Florida, 2024 Hightower Fellow, and 2024 Leadership Florida Connect class member. 

Megan's dynamic personality extends beyond her professional pursuits as she also boasts an adventurous side with a penchant for adrenaline-inducing activities including wing walking on planes. Her love for fantasy books showcases her imaginative and creative mind, indicative of her innovative approach to her work. Megan competitive spirit was the force behind her obtaining a Division I basketball scholarship at the University of North Florida, and after graduation she was on stage in fitness competitions - even landing her a spot on season 1 of Steve Austin's Broken Skull Challenge (episode 8 if you have nothing but free time).

Megan is still involved in local sports as she is the one of the owners of the Jacksonville Icemen, the Community First Igloo, the Savannah Ghost Pirates, and the Allen Americans. 

Despite her numerous accomplishments, Megan prioritizes her role as a mother to Israel and a wife to Reggie.

Robin Phelps-Raymond is Founder and CEO of Red Admiral Ventures, a business acceleration company guiding women Founders/CEOs in scaling her leadership, team and business to 8-figures. Her personal vision is Transforming Lives, Livelihoods, and Communities through Entrepreneurship.

Robin spent the first half of her career working in sales and business development for technology start-ups in Silicon Valley. Her passion for and alignment with the PS27 Foundation vision and work of helping diverse Founders achieve sustainable growth is rooted in her experience on the same journey. In Aug of 1999 she co-founded with another female a software company in Orlando. With crucial support from the ecosystem in Central Florida for early-stage entrepreneurs and from Springboard Enterprises for women entrepreneurs, they raised a total of $13.1M of Angel and VC funding in 3 rounds with increasing valuation each round and were on a path to 8-figures. After closing the company in December of 2002 she embarked on her mission to change that outcome for women and other diverse Founders and help them succeed at building their business to 8-figures.

From 2012 – 2020 she was a Director of entrepreneurship programs at University of Central Florida, including NSF I-Corps, the UCF VentureLab, MegaWatt Ventures Cleantech business competition, and GrowFL statewide program for second-stage companies. Prior, she was a Director in Denver, CO for the non-profit CTEK, an organization supporting entrepreneurs with programs, business incubators, and CTEK Angels investor group.

Robin has her Bachelor of Science in Computer Science from Pepperdine University, her Master of Science in Management from University of Denver, and her PhD (ABD) from University of Colorado Denver. She lives in Sanford, Florida with her husband, John.

Randall Thomas is a veteran talent acquisition strategist and innovation leader dedicated to scaling both people and local ecosystems. Currently serving as the Senior Resource Manager for Kavaliro, Randall brings over nine years of expertise in placing top-tier talent across IT, Engineering, and Supply Chain sectors. His strategic oversight extends to The Link, where he serves as Chief Strategy Officer, driving the vision for one of the region’s premier hubs for innovation and collaboration.

A fixture in the Jacksonville business community, Randall was recently honored as one of the Jacksonville Business Journal’s 40 Under 40. His commitment to the River City is reflected in his extensive board service, including the JAX Chamber’s Arlington Council, 100 Men Who Care, and the Think Bold Festival and Conference leadership team. He further supports the entrepreneurial landscape through advisory roles with the Jax Business Calendar and Gray Collar.

As a prominent voice in modern media, Randall is the Founder and Host of the PB & JAX Podcast, a podcast dedicated to Northeast Florida’s small business community. He also serves as the Chief Strategy Consultant for the Tech Legacies Podcast and co-hosts Frontline Visionaries, cementing his status as a thought leader in the intersection of technology and talent.

A U.S. Navy Veteran and a proud Florida State University graduate, Randall is passionate about veteran advocacy and mental health. from Austin, Texas, Randall has spent nearly two decades in Jacksonville, where he remains a tireless champion for the city's growth, innovation, and future potential.

Raj Gupta III is an entrepreneur, business strategist, and investment-focused executive whose career has centered on building scalable businesses, identifying emerging market opportunities, and developing technology-driven operating platforms. He is the Founder and Chief Executive Officer of Visionary Strategic Solutions LLC, a consulting and strategic advisory firm that partners with organizations across multiple industries to modernize operations, deploy artificial intelligence driven systems, and accelerate sustainable growth.

Raj’s entrepreneurial journey began early and has been shaped by hands on operational experience and a deep understanding of sales leadership. At the age of twenty he launched his first business selling Kirby vacuum systems door to door. The experience instilled in him a strong foundation in discipline, resilience, and relationship driven sales. He later advanced to the role of Director of Sales at a marketing firm where he built and managed high performance sales teams while developing strategic frameworks for revenue growth and market expansion.

In 2019 Raj founded Purified Leads LLC, a digital marketing and customer acquisition company focused on performance driven lead generation and data based marketing systems. The company experienced rapid growth and was successfully acquired in 2021. Following the acquisition, Raj assumed senior executive responsibilities as Vice President of Sales and Marketing, where he played a key role in scaling revenue operations and building national sales teams. Under his leadership the organization generated more than one hundred million dollars in revenue during the COVID-19 pandemic, demonstrating his ability to drive growth even in volatile economic conditions.

In addition to operating companies, Raj has developed expertise in strategic partnerships, technology commercialization, and early stage venture collaboration. Through his advisory and consulting work, he has been involved in the development of software platforms, AI driven customer service systems, billing infrastructure, and sales automation tools designed to improve operational efficiency and drive measurable performance outcomes.

Beyond his professional pursuits, Raj is deeply committed to family and community. He is the father of six children and is actively involved in mentorship and community initiatives in Jacksonville, Florida. He is a member of El Beth-El Church, where he participates in outreach and charitable programs supporting underserved families. Raj is also an active Freemason and York Rite member, organizations that emphasize leadership, philanthropy, and ethical service.

Through his entrepreneurial leadership, investment minded approach to business building, and dedication to community engagement, Raj Gupta III continues to work at the intersection of innovation, growth, and long term value creation.