Episode #103 · June 16, 2025 · 50 min

Hale Law's Two Patricks on Turning a Last Name Into a Billboard Empire

Patrick Hale and Patrick Iyampillai explain how a former prosecutor and a former insurance investigator built a 34-person personal injury firm around the slogan Go To Hale.

Patrick Hale & Patrick Iyampillai of Hale Law

Patrick Hale started Hale Law in April 2018 after leaving a prosecutor's job, funding the launch by selling his house and taking cash-pay criminal defense cases to keep money flowing while he built a personal injury practice on the side. He brought on his now-partner, also named Patrick -- Patrick Iyampillai -- in 2019, and the two shared an office smaller than either of their current private offices, each hearing every word of the other's phone calls. The slogan that now anchors billboards across Tampa and Sarasota, Go To Hale, survived a focus group against rejected options including Go To Heaven before the firm settled on something loud, memorable and, in Hale's words, great as hell.

From Prosecutor and Private Investigator to Trial Attorneys

Iyampillai brings an unusual asset to the partnership: as a teenager he worked as a licensed private investigator for insurance companies, surveilling workers'-comp claimants suspected of fraud -- including one man who claimed a five-pound lifting restriction and was later caught popping a wheelie out of his driveway on a motorcycle. That background, he says, sharpened his instinct for which injury claims are legitimate and which aren't; the firm turns away cases it doesn't believe in, both as a moral stance and, Hale notes, a practical one, since a jury won't believe a story the attorneys themselves doubt.

The firm has grown from four people in 2019 to 34 today, including six attorneys, with plans to top 40 by year's end. Roughly three-quarters of their cases settle without a lawsuit being filed, but Hale and Iyampillai argue that willingness to actually go to trial -- which they did in a case just months before this taping, winning a defense-favored jury verdict for a client insurance adjusters initially blamed -- is what keeps settlement offers honest. They also flag a nationwide push by rideshare companies to cap attorney contingency fees at 20 percent in personal injury cases, well below Florida's standard 40 percent, arguing it's designed to make it financially unworkable for strong attorneys to take on Uber and Lyft cases at all.

Split Verdict on Roundabouts

Asked about roundabouts, the two land in different places: Iyampillai worries Sarasota is building too many of them and that even low-speed roundabout collisions can cause real injury, while Hale points to the safety data -- no more T-bone collisions -- as reason enough to keep them. Both note, half-joking, that the decorative landscaping in the center of many roundabouts is intentionally placed to block sightlines and discourage drivers from misjudging oncoming traffic, a detail they say they've picked up from Florida Department of Transportation crash-reconstruction experts used in their own cases.

They recommend attorney and SRQ Magazine co-founder Bill Sterbenski and Teen Court of Sarasota executive director Heather Todd as future guests.

What you'll take away

  • Hale Law grew from four people in 2019 to 34 today, with six attorneys, and expects to top 40 employees by year's end
  • About three-quarters of the firm's personal injury cases settle without a lawsuit being filed
  • Rideshare companies are pushing legislation to cap personal injury attorney fees at 20 percent, well below Florida's standard rates
  • Co-founder Patrick Iyampillai worked as a licensed private investigator for insurance companies as a teenager, screening workers'-comp fraud claims
  • The firm's attorneys are split on roundabouts: safer in aggregate, but concerned about the sheer number now being built in Sarasota
“The best way to get a million dollars for a case is to mess up a three million dollar case.”
, Patrick Hale & Patrick Iyampillai of Hale Law
“If we take a case, it's because we believe in it. We believe in the client.”
, Patrick Hale & Patrick Iyampillai of Hale Law

Places mentioned: Fruitville Road