In this episode of the 256 Investor Podcast, local insurance expert Will Wright joins JD for a deep discussion on insurance claims, how it really works and how to be in control and get the best of your policies. Will Wright is the founder of The Will Wright Agency in Decatur, Alabama. With over three decades of experience in property, casualty, and life insurance, Will breaks down the real truths behind homeowners and rental property coverage — from how to file a claim that actually gets paid to understanding how insurance cycles impact your bottom line.

Topics Covered with Timestamps

00:01:06 | Meet Will Wright

Will shares his 30-year journey from life insurance agent to independent agency owner.

00:02:27 | The Truth About Insurance Cycles
Why rates rise and fall every 5 years — and how savvy investors can take advantage.

00:03:37 | When “We’ll Never Cancel You” Isn’t True
Will exposes major carriers that drop customers despite promises of lifetime coverage.

00:05:09 | Agents Who Care vs. Agents Who Don’t
How to spot a good insurance agent — and why your agent’s involvement can make or break a claim.

00:07:55 | The Hidden Risk of Filing a Claim
How filing without proof can raise your rates even when you’re denied.

00:08:13 | What Makes a Valid Roof Claim
Will explains how roofers and adjusters evaluate hail damage and why proper documentation matters.

00:10:18 | Tornado & Catastrophic Losses Explained
How “cat loss” events affect adjusters, agents, and your payout potential.

00:11:55 | Managing Properties from Out of State
Essential steps for investors who rely on property managers to file claims correctly.

00:14:20 | Deductible-Coverage Policies
A new insurance product that covers up to $25,000 of your deductible for tornado losses.

00:15:19 | How to Appeal a Denied Claim
The step-by-step process to re-open a claim and increase your odds of success.

00:18:19 | When Not to File a Claim
Why using insurance for “maintenance” causes premiums to skyrocket — and what to do instead.

00:20:19 | Common Water Damage Claims
Burst lines, leaking hoses, and other hidden risks that lead to expensive water losses.

00:23:01 | Slow Leaks vs. Sudden Losses
How insurance defines “sudden and accidental” — and why slow leaks are almost always denied.

00:24:00 | The Mold Myth
Why most mold claims are denied and how minimal coverage really works.

00:27:03 | Investor Insurance Strategy
Will shares practical advice for investors — higher deductibles, fewer riders, smarter cash flow.

00:29:22 | Multifamily Coverage Challenges
Why insuring 5+ unit properties is difficult and costly in today’s market.

00:31:17 | Metal Roofs & Cosmetic Damage Clauses
The fine print that can leave you uncovered after hail damage.

00:32:34 | Final Advice for Investors
Budget for maintenance, use insurance wisely, and “buy low, sell high.”

00:33:00 | Contact The Will Wright Agency
Will shares how investors can reach his office in Decatur, Alabama.