The IBJ Podcast with Mason King

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.

IBJ’s editor on making mistakes, combatting bias, diversifying revenue

We at the Indianapolis Business Journal committed a serious error earlier this month that created significant problems for one of central Indiana’s most important not-for-profit organizations. If you listened to last week’s podcast, you have a sense of what happened. In the interest of transparency, IBJ Editor Lesley Weidenbener explained in her latest column how the error occurred and how that affected the organization. The column opens a window to the workings of the IBJ newsroom and the potential for multiple editors to miss a red flag when moving quickly to break news. For this week's episode, host Mason King recruited Weidenbener to throw open the curtains and give you an even broader look inside IBJ. In this week's episode, she addresses the error, some of the questions posed regularly about IBJ's financial health, and how its leaders maintain barriers between the newsroom, advertisers and the politics of IBJ’s owner and CEO.

Indiana Black Expo’s CEO on Circle City Classic’s gridiron shift and creating hoops invitational

Founded in 1970, Indiana Black Expo has broad brand recognition for its 10-day Summer Celebration, which highlights Black culture and elevation. But the umbrella not-for-profit organization operates 365 days a year, acting as a voice and vehicle for the social and economic advancement of Black youths and families. The other high-profile annual event hosted by IBE is the Circle City Classic, which typically features a football game between two historically black colleges or universities, along with a downtown parade and events focused on education, careers and culture. Last week, IBE announced a change at the heart of the Classic amid declining attendance, as well as the addition of a new event that would bring basketball teams from HBCUs to Indianapolis. CEO Alice Watson is our guest this week to explain in detail the economic tensions behind the switch this fall from college football programs to Indianapolis-based high school teams, including the $750,000-plus price tag IBE faced to recruit college teams and their bands this year. She also delves into the creation of an HBCU basketball invitational for 2027, which is expected to be more affordable for attracting programs. And she takes a deep dive into all of the educational programming and scholarships IBE offers throughout the year without nearly as much fanfare.

Why do some big companies fail at meaningful innovation?

Virtually every large or medium-sized company today says it’s dedicated to innovation, especially in light of the generational disruption in business created by artificial intelligence. But “innovative” is a broad and squishy term. One company’s so-called “cutting-edge development” might look to another like rearranging the deck chairs on the Titanic. Elliott Parker of Indianapolis-based startup builder Alloy Partners has seen many examples of what he calls “the illusion of innovation” – meaning corporate attempts at change that are either mostly for show or that don’t go nearly far enough to make a real impact. Indeed, Parker says, large companies often are unable to innovate their business models because they’re designed and incentivized to keep doing the thing they’re successful at doing.  For the owners, executives and managers who are truly interested in making big bets on innovation and challenging dogma within their businesses, what will work? Parker is our guest this week to talk about his book, titled “The Illusion of Innovation,” and how companies can evade the traps. He also discusses how the recent explosion in AI is altering the innovation ecosystem and how companies are built and run. Parker says he’s optimistic, although “things are going to get very, very weird very quickly.”

Final Four co-chairs debrief on Post Malone, Fan Fest, coach swag and what it all meant

Earlier this month, Indianapolis wrapped up its ninth Final Four since 1980 — a Herculean hosting gig that requires thousands of volunteers and flawless coordination between the NCAA, the city of Indianapolis, hospitality officials, transportation services, public safety workers, a bunch of colleges and an untold number of vendors. Near the top of the organizational chart were the co-chairs of the local organizing committee — Judith Thomas and Nate Feltman. The world saw the basketball action online and on TV, and many in Indianapolis experienced big attractions staged in concert with the Final Four, including a three-day music festival witnessed by tens of thousands of fans. In this edition of the podcast, Thomas and Feltman take us behind the scenes of the three-year planning process and then the week of the event as plans played out in sometimes unexpected or poignant ways. For example, Feltman became a wingman of sorts for superstar Post Malone. Thomas, who attended Indy’s first Final Four in 1980, clearly saw her career arc from that experience to the convention industry, her role as deputy mayor, CEO of the Indy Arts Council and committee co-chair. Feltman, owner and CEO of IBJ Media, also experienced a change of heart on the city's lead role in financing the 800-room Signia by Hilton hotel, now nearing completion.