The IBJ Podcast with Mason King

Immigration law firm swells from one-man band to 137 employees, thousands of cases

In 2009, a freshly graduated Jason Flora opened a law firm in a tiny office on the west side of Indianapolis near Hispanic-run car lots, Honduran restaurants and Guatemalan grocery stores. In its early days, the firm was a one-man shop, with Flora, who speaks Spanish fluently, working 60 hours or more a week and often driving back and forth between Chicago’s immigration court and his office. Last month, Flora Legal Group ranked No. 3 on IBJ’s list of the region’s fastest-growing companies based on its two-year growth, which ballooned 250%. It now has 23 attorneys among its nearly 140 full-time employees, who handle thousands of cases per year. And yet the firm’s mission is essentially the same as it was in 2009: to protect the rights of immigrants and provide the legal services they need — particularly in immigration cases — to make their lives better and more prosperous. In this week’s edition of the IBJ Podcast, Flora expounds on the evolution of his firm. As he explains it, one of the reasons he started his career as a street lawyer was due to the lack of interest from recruiters in established law firms. And he delves into how he learned he could be more valuable by pursuing more growth for the firm than he could by spending all of his time practicing law.

Indy-based tech exec on joining global firm, being remote-only leader

Darin Brown is an executive for a global software testing firm with hundreds of employees and a roster of some 80,000 freelancers. But to do his job, he doesn’t have to leave his home in Westfield, Indiana. The firm, known as Testlio, is one of an increasing number of companies that don’t have physical home bases and instead let employees work entirely remotely. Brown recently had the same arrangement when he worked for Zoom, the company virtually synonymous with remote work. In 2022, Zoom acquired a startup that Brown co-founded in central Indiana which led to him being named Zoom’s head of product for productivity applications. He left Zoom earlier this year to be Testlio’s chief product and technology officer. Brown boasts a distinguished career in the Indianapolis area tech community as a project manager and developer. The list of companies includes ChaCha Search, ExactTarget, Salesforce and then Angie’s List, where he was chief technology officer. There he found a problem that he was inspired to solve by co-founding the startup Docket, which then led him to Zoom. In this week’s podcast, Brown discusses his new position with Testlio, his tenure with Zoom and how he made the transition at mid-career from supervising team members in the office to being an online-only leader.

Indy Pride chair talks festival changes, political backdrop and financial challenges

In this week’s edition of the IBJ Podcast, Indy Pride Inc. board Chair Alex Richardson previews the June 13 parade on Massachusetts Avenue and a revamped festival footprint spanning Military Park and White River State Park as the nonprofit marches forward under new leadership. Richardson, a DePauw University faculty member who became board chair in December, discusses the January hire of Executive Director Jennifer Carruthers, who previously led Capital City Pride in Des Moines. Richardson also addresses the financial pressures facing Indy Pride, including a $210,000 budget shortfall in 2024 tied in part to reduced corporate sponsorship, and explains how new individual giving programs and small-business outreach aim to close that gap. This year’s events will include a Saturday night concert featuring headliners Todrick Hall, Brooke Eden and Crystal Waters, in addition to a New York City ballroom showcase rooted in the Harlem ballroom scene of the early 1970s. Richardson also responds to Gov. Mike Braun's proclamation of June as "Nuclear Family Month.”

Pete the Planner on why Americans feel broke at $150,000 a year

Hitting six figures in household income is a powerful milestone. You are situated comfortably in the middle class, which in the U.S. is currently defined as making $56,000 to $168,000 per year. If we want to zoom in on Indiana, the parameters for the middle class are $48,000 to $144,000 per year. We all know that the cost of living is rising faster and higher than anyone wants, but doesn’t it seem like you should be able to make it work on six figures per year? Over the last couple of years, a national conversation has been brewing online about why some people who make as much as $150,000 per year feel like they’re barely getting by. And consumer sentiment just last week hit its lowest point in at least 50 years.   Pete the Planner isn’t here to judge. His computations show how easy it can be for the finances for a $150,000 household to go off the rails. One unexpected blow to your budget for housing, transportation, child care or essentials like food can make it feel like the ceiling is caving in. At the same time, we need to consider whether the expenses we believe are necessary are actually the result in our culture of normalizing overconsumption. Pete is our guest this week to explain the math behind the financial struggles for $150,000 households and provide some guidance – with a dose of straight talk – about reducing expenses.

After firm’s $50M sale, co-founder was done with startups. Then AI pulled him back in.

Santiago Jaramillo has been the subject of – or at least mentioned in – 44 articles in the Indianapolis Business Journal, including several columns he wrote about entrepreneurism. The stories largely appeared between 2013 and 2021, while he was building, running and exiting two Indianapolis-area tech companies. After the second firm, known as Emplify, was acquired for $50 million in 2021, Jaramillo had a severe case of burnout. He went on an extended sabbatical, planning to forego any future forays into founding startups.   Then ChatGPT dropped. Suddenly entrepreneurs and executives had widespread access to artificial intelligence tools, and Jaramillo quickly saw their potential for transforming businesses and the workflows of their employees. The pull eventually proved too great. Jaramillo co-founded a firm named Pragmatico to help companies make the leap into AI in a way that sticks. In this week’s podcast, Jaramillo takes us on his entrepreneurial journey, which began in Colombia, South America, where he narrowly avoided a kidnapping. His career took turns through Florida, Indiana and Australia before settling back in the Hoosier state. Jaramillo also discusses why he decided to get back in the game, the reasons why many firms have trouble adopting AI and why the technology shouldn’t be set loose without human judgement as a guide.