Randy Smith
Randy Smith is a South Florida entrepreneur, husband, father, grandfather, sailor, investor, and philanthropist.
WHO IS RANDY SMITH?
Randall “Randy” Smith is the founder and former President of Heritage Carpet & Tile, Inc., a leading flooring and interior finish contractor based in Florida. Originally from Northern California, Randy relocated to Florida in 1983 to launch the company. Over the next 35 years, he grew Heritage into a statewide enterprise before selling to private equity in 2019. He continued as President through the transition and ultimately sold the roll-up to Lowe’s in 2025, after which he retired.
Today, Randy is an active investor and developer in both commercial and residential real estate. He also serves as fundraising chair for Warrior Sailing, a nonprofit supporting veterans through maritime training and community.
Randy splits his time between Delray Beach, Florida, Park City, Utah, and his sailing yacht SV Happy Together, which he’s sailing around the world with his wife Lennie. Together for 28 years, Randy and Lennie have three children, four grandchildren, and a shared passion for travel, adventure, and giving back.
His hobbies include sailing, scuba diving, skiing, riding dirt bikes, playing guitar, and staying engaged in American politics—with a focus on promoting good governance for future generations.
Heritage Carpet & Tile, Inc.
Randy and his family built Heritage into a statewide leader in product supply and installation for new construction homes. At its peak, the company employed over 1,200 team members across four locations and served all major homebuilders in Florida.
Retirement Day 2024
Image Studios ®
Image Studios is a high-end salon suite concept that empowers beauty professionals to become entrepreneurs. Randy, Lennie, and their adult children are developing Image Studios locations throughout Florida and Georgia.
Warrior Sailing
Warrior Sailing provides maritime education and outreach for wounded, ill, and injured service members and veterans. Since 2017, Randy and Lennie have been substantial donors and chairs of the national fundraising committee. They actively participate in events and training camps across the country.
Sailing is the platform through which Warrior Sailing reconnects veterans with camaraderie, purpose, and physical and mental wellness.
Sailing SV Happy Together
Randy’s love for sailing began in 1975, racing on San Francisco Bay with his father. After relocating to Florida in 1983, the family enjoyed powerboating across South Florida, the Keys, and the Bahamas.
In 2012, Randy and Lennie returned to sailing and have since cruised over 50,000 nautical miles aboard three different yachts. Their voyages have spanned the Bahamas, Caribbean, Colombia, Panama (with three Panama Canal transits), and the West Coast from San Francisco to Panama.
In 2023, they took delivery of their new custom-built carbon fiber catamaran in Cape Town, South Africa, and are now circumnavigating the globe.
Sailing SV Happy Together Youtube
In 2015, Randy began documenting their sailing adventures on YouTube. What started as a way to keep in touch with friends and family quickly grew into a hit sailing channel.
SV Happy Together became a top 20 sailing channel on YouTube, with over 30,000 subscribers and millions of views. The channel was never monetized; instead, it helped raise awareness and funds for Warrior Sailing.
Consulting & Real Estate
Randy regularly appears on podcasts to share insights on business, investing, tax strategies, and wealth accumulation. He speaks at conferences and mentors entrepreneurs, helping others achieve business success and financial independence.
He also creates investment opportunities through real estate syndications for individuals seeking to diversify their portfolios with renowned sponsors including MFP Capital.
MFP Capital is a boutique real estate investment firm headquartered in Ponte Vedra Beach, Florida. We invest in high-quality, yield-generating multifamily and opportunistic, mission-critical net leased assets.
Founded by Peter Von Der Ahe and Tyler Edwards, MFP is built on over 35 years of combined industry expertise, honed through our leadership team’s involvement in over $6 billion in real estate transactions. We excel at identifying and acquiring undervalued assets in growing overlooked markets, transforming them into stable, income-producing properties with long-term appreciation potential.
Independence Place Multi Family Apartments Hinesville GA
Independence Place Multi Family Apartments Hinesville GA
Canlak corporate HQ NNN investment Minneapolis
Randy’s investment advice shorts
Tiger 21
Randy is a senior member of the Palm Beach Chapter of Tiger 21, a global peer network for high-net-worth entrepreneurs focused on investment strategies, wealth preservation, and legacy planning after business exits.
No Labels
Randy joined No Labels in 2020, a nonpartisan organization focused on bipartisan solutions to the nation’s biggest challenges. Formed over a decade ago, No Labels includes 56 members of Congress and 8 Senators united around pragmatic policymaking.
With his business goals achieved, Randy saw an opportunity to help improve government and leave a better future for his children and grandchildren.
Podcasts
Randy has been invited as a guest on podcasts related to business and financial advice, investing, tax strategy, and wealth accumulation. In addition, Randy speaks at conferences and mentors entrepreneurs. He is passionate about donating his time to help people achieve their business and financial goals.
Connect with me