In this episode of the Freedom to Start Fresh podcast, host Kunal chats with Ty Whitney, founder of Whitney Commercial Insurance Advisors, to explore the journey from lawn-mowing teenager to one of Florida’s most trusted commercial insurance agents. With nearly four decades of experience, Ty’s story blends entrepreneurial spirit, surfing wisdom, and battle-tested risk strategy — making for a powerful lesson in protecting businesses the right way.
From Lawn Service to Legacy
Ty’s business acumen revealed itself early. At just 10 years old, he and a friend launched a lawn service in Lighthouse Point, Florida, doing everything from mowing yards to waxing boats. By 17, he was employing surfer friends, operating seven days a week, and saving enough money to start college with a full bank account. His stepfather, a CPA, was stunned by Ty’s self-made financial foundation — so much so that he made him file taxes immediately.
Riding Waves and Reading Risk
Ty’s passion for surfing took him across Florida’s coastline, from Hillsboro Beach to sharky swells in New Smyrna. He recalls navigating treacherous surf breaks — and dodging literal sharks — as formative lessons that now shape how he helps clients navigate risk in business.
“Surfing changes constantly, and so does business. Every company is unique, just like every wave,” Ty explains.
Insurance with Insight: Why Most Policies Miss the Mark
Today, Ty specializes exclusively in commercial insurance, and his firm is known for meticulous, diagnostic reviews of business policies. He frequently encounters cases where companies unknowingly operate without coverage for their core services, especially when policies are purchased online or through generalist agents.
Case in point: A structural engineering firm hired for condo milestone reports unknowingly had a policy that excluded structural engineering — a critical and costly gap. Ty’s team corrected it and safeguarded the business, but the mistake could’ve been catastrophic.
A Philosophy Built on Partnership
Ty isn’t just selling policies — he’s building long-term relationships. His team customizes protection for evolving risks, including:
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Cyber liability (including ransomware, data breaches, media misuse)
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Employment practices liability (e.g., wrongful termination, harassment)
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Subcontractor risk transfer for construction businesses
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Adaptable coverage as clients grow or pivot operations
One story stands out: When Ty’s agency suffered a 13-day data lockdown from a third-party system breach, his cyber liability coverage kicked in immediately, covering legal, recovery, and IT costs. “It was the longest 13 days of my life — and we were the lucky ones. We had the right coverage,” he says.
Avoiding Common Mistakes
Ty offers clear advice to business owners:
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Don’t buy insurance in five clicks. Engage with your agent. Ask questions. Read your policy.
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Don’t underinsure cyber risk. A $2,000 premium could save a $20M business.
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Update policies when your operations change. Growing your business? Your coverage needs to grow too.
Quickfire FAQ from Ty Whitney
Why do my premiums keep rising?
Growth, payroll increases, and claim history all raise risk — and price.
How long do claims affect my premiums?
Up to 5 years. Claims evolve, and insurers monitor them over time.
Do I need cyber liability if I don’t take credit cards?
Yes. Cyber crime, extortion, media liability, and business interruption can hit any business.
How much liability coverage should I carry?
Start with $1M; $5M is often ideal depending on your exposure and budget.
What’s a common mistake business owners make?
Not knowing what’s in their policy — or not bothering to ask.
Connect with Ty Whitney
📍 Location: South Florida (serving businesses statewide)
📞 Phone: 954-448-9711
📧 Email: ty@tybcadvisors.com
🌐 Website: www.tybcadvisors.com
