In this episode of Legal Late Night, we’re descending into the madness of the 2026 NCAA tournament before diving deep into the tech stack with Daniel Steinberg, the CEO of Lawbrokr. From predicting a 1-in-9.2 quintillion bracket to plugging the leaks in your law firm’s intake funnel, we’re exploring what happens when data meets human connection.
As we roll into the Final Four of 2026, Jared is brutally honest: he’s a total douchebag. His favorite college team is Duke, he likes the Patriots, and he has zero regrets about selling his NCAA tournament tickets to see the Celtics win their 18th banner. But there is something about March Madness that captures the soul.
Between the “First Four” play-ins and the winner-take-all single-game advancement, the tournament is a masterclass in randomness. So, Jared looks back at the most impactful Final Fours ever—like 1966, where Texas Western (now UTEP) destroyed Jim Crow-style recruiting forever by winning with an all-black starting five, or 1979, where the Magic Johnson vs. Larry Bird showdown literally saved the NBA from irrelevance.
After geeking out over his signed Larry Bird jersey, Jared sat down with Daniel Steinberg, the founder and CEO of Lawbrokr (that’s Lawbroker without the “E”—don’t make Jared say “Law Broke” again). Daniel cut his teeth in the Clio app ecosystem, managing over 250 partners before deciding to launch his own venture.
Launching a legal tech startup isn’t all ramen noodles and sleepless nights (though Daniel does have a newborn, so the sleep part is debatable). It’s about flexibility. Lawbrokr started as a consumer marketplace, but Daniel quickly realized the unit economics were broken. Instead of fighting Google for expensive “divorce lawyer” keywords, he pivoted. He took the core pre-screening technology and turned it into a B2B powerhouse that helps law firms operationalize their own traffic.
Daniel’s core thesis is simple: Your law firm likely has a leaky funnel. You might be killing it with 10,000 web visitors a month, but if they aren’t converting through your forms or chat, you’re just paying for “brand awareness” that doesn’t pay the bills.
In a segment inspired by the fine gentlemen of Prestige Worldwide, we subjected Daniel to a game of “Boats and Hoes.” The rules were simple: Jared reads the name of a real historical boat and a real historical “hoe” (socialite/mistress/adventurer), and Daniel had to guess which was which.
Proving that an accounting background makes you excellent at reading people, Daniel went an astounding 5-of-6. He correctly identified the Mary Rose (King Henry VIII’s warship) and the Vasa (the Swedish ship that sank minutes into its maiden voyage). He also managed to navigate the scandals of Madam DuBarry and Messolina without breaking a sweat. If predicting a bracket is a 1-in-9.2 quintillion shot, Daniel’s trivia performance was the statistical equivalent of a slam dunk.
Ready to stop losing leads and start converting traffic? Visit Lawbrokr today. Be sure to visit Legal Broadcasting Company often for our latest podcasts. If your law firm needs a “perfect reset,” contact Red Cave Law Firm Consulting.
Because volume is a vanity metric. If you increase your conversion rate by even 5%, you are generating more cases from the traffic you already have without spending an extra dime on Google Ads.
No. Lawbrokr is a digital intake and marketing solution. It is designed to live inside your existing workflow and feed high-quality data into your CRM (like Lawmatics) or Practice Management software (like Clio).
Primarily for onboarding and internal data transparency. It helps customers implement tools faster and provides “agents” that help firm owners understand the inner workings of their own marketing data.
