Recurring guest, Andrew Yang is back — and he’s not pulling punches. In this wide-ranging, deeply honest conversation, Jenn sits down with Yang to talk about the forces reshaping our lives right now: AI, money, power, politics, and what happens when technology moves faster than our institutions can handle. This isn’t a campaign speech or a tech hype session, it’s a real, sometimes funny, sometimes unsettling conversation about why Americans feel squeezed, why trust in institutions is collapsing, and why AI is about to upend work, wealth, and opportunity whether we’re ready or not.  Yang opens up about running for president (again), the broken two-party system, why Silicon Valley lost its moral compass, and what it actually takes to build businesses that help people instead of extracting from them. Along the way, Jenn pushes Yang on a few topics like billionaires burning money on ego projects, why universal basic income is no longer a fringe idea, and how companies like Yang’s Noble Mobile are trying (quietly) to put cash back into people’s pockets. It’s candid, emotional, occasionally profane, and one of the most unfiltered conversations we’ve had on the show. If you’ve ever wondered who’s really running the country — politicians, tech giants, or venture capital — this episode is for you.

What You’ll Learn

Episode Resources

Tell Us What You Think – Do you think AI will actually make life better — or just make a few people richer? Would you ever trust a company that claims it wants to make you less broke? Drop your thoughts, push back, or tell us where you agree (or disagree) — this is one we expect people to argue about. Support the Show – If you like what you hear, please rate and review Techishly Jenn — it helps more people find the show. Questions or comments? Email [email protected].

The IRS is using it. So are many filers. Here’s what you need to know. “I am more concerned about the IRS having really bad AI than I am about our tax software having decent AI. The IRS and AI—what could possibly go wrong?” That’s the question driving this episode of Techishly Jenn. Tax season is here, and for the first time, AI isn’t just a feature—it’s actively processing your return and the IRS system reviewing it. Algorithm vs. algorithm. And your biggest check of the year is sitting right in the middle. Host Jennifer Jolly talks with Intuit executive Mark Notarainni about how TurboTax and Credit Karma are using AI with guardrails, human review, and serious security protections. But she doesn’t stop there. She tracks down real users—like 26-year-old startup founder Musa Hakim Jr., who says AI made filing “easier, faster, clearer”—and skeptics like performer Barbara Kamara, who caught ChatGPT giving flat-out wrong tax advice. From cost basis errors that cost people thousands, to the IRS using machine learning to flag side hustles and crypto, this episode breaks down what’s hype, what’s helpful, and what could bite you if you’re not paying attention.

What You’ll Learn

Episode Resources

Tell Us What You Think…Would you trust AI to do your taxes? Have you already filed this year? Did it help — or just make things more confusing? Drop your thoughts below. Support the Show…If you like what you hear, please rate and review Techishly Jenn — it helps more people find the show. Questions or comments? Email [email protected].

Blackhawks legend, Olympic Silver medalist and NHL Hall of Famer, Jeremy Roenick joins Jim Bob Morris and Dane Neal on WGN Radio. Hear as Jeremy shares his experience and the impact of being a part of the patriotic pageantry that is the Olympic Games. Listen as Jeremy breaks down the U.S. Women’s team and how they may the best ever from America. Jeremy shares the pride and importance of Team USA on the world stage and impact on generations of girls, players and fans. Stay tuned to The Jim Bob Show with Dane on WGN Radio and the ROAR Podcast Series. Each episode brings player interviews and guests features with the Tailgreeter Tales from the Tailgates and JimBob’s WANNA Parlay picks of the week. View the video version of the FULL interview here  https://youtu.be/F8VzoTPOtIc?si=WKj-7cus-Ywn-KJa

Always WIN with the Undefeated Flavor of El Bandido Yankee, the Official Tequila of GameDay! For events, recipes and places for purchase go to www.elbandidoyankee.com 

This is a can’t-miss episode. There’s a quiet rebellion happening — in kitchens, classrooms, and bedrooms — and it’s not coming from Silicon Valley. In this powerful episode of Techishly Jenn, Jenn sits down with Jonathan Haidt and Catherine Price, co-authors of the new book The Amazing Generation, to talk about what’s really happening to kids growing up with smartphones, social media, and now AI. If The Anxious Generation helped parents understand what went wrong, The Amazing Generation is about what comes next — and why kids themselves are starting to say “enough.”  This isn’t a tech-panic episode. Jenn, Jonathan, and Catherine make it clear: technology isn’t the enemy. But addictive design, unregulated platforms, and giving kids adult-grade tech before their brains are ready? That’s where things go sideways. Together, they unpack how smartphones became “supercomputer slot machines,” why social media harms girls and the broader techno-sphere traps boys, and why AI may pose an even bigger developmental threat if we don’t slow down and get this right. Along the way, Jenn shares candid parenting moments, including the uncomfortable but essential question every parent should ask their child — and themselves. This is one of the most honest, emotional, and practical conversations we’ve had on the show — about kids, screens, guilt, hope, and how we reclaim childhood without shame or lectures.

Tell Us What You Think Have you already given your child a smartphone — and now wish you’d waited? What rules are working (or not) in your house? This episode isn’t about guilt — it’s about doing better together. Share your thoughts, questions, and hard moments with us.

Support the Show Do us a favor. If you like what you hear, please rate and review Techishly Jenn — it helps more people find the show. Send your questions and comments to [email protected]. 

There are tens of thousands of gadgets, gizmo’s and techy doo-dads at CES. But how many of them actually matter to you and me? What deserves a spot in your home and life this year and well into the future? Those are just a few of the questions Jenn and Producer Scott asked themselves and hundreds of other gadget-insiders for a solid week at the world’s most powerful tech convention in Las Vegas in early January. Jenn and Scott have more than 30-years of CES experience under their well-worn belts. In this 2026 recap episode of Techishly Jenn, the two of them break down what stood out, what surprised them, what made them laugh, and what made them both quietly whisper, “Oh… this might actually matter.” From robots that crash (and occasionally charm), to AI health mirrors that claim to know you better than your doctor, to toilets that are doing way too much, this episode cuts through the hype to focus on the tech that feels real, useful, or at least entertaining enough to talk about. They also bring back everyone’s favorite segment — Marry, Fund, Kill — because nothing says serious tech analysis like ranking gadgets based on vibes, value, and whether we’d actually sleep with them or just take ‘em out for a one-night stand.

  What You’ll Learn

Episode Resources

Which CES gadget would you marry? Which one deserves funding? And which one made you say, “Absolutely not”? Drop your hot takes, disagreements, and favorite CES finds — because half the fun of CES is arguing about it afterward.

Do us a favor. If you like what you hear, please rate and review Techishly Jenn — it helps more people find the show. Send your questions and comments to [email protected]. 

LinkedIn: Jennifer Jolly Listen on WGN, Apple Podcasts, or Spotify Newsletter: Techish by Jennifer Jolly YouTube: @TechishbyJenniferJolly TikTok: @JenniferJollyTechish Instagram: @JennJolly Twitter/X: @JenniferJolly

Bears legend and NFL Hall of Famer Devin Hester joins Jim Bob Morris and Dane Neal on WGN Radio. Hear as Devin shares what made him the all time greatest kick returner plus magic moments in the NFL and his start at University of Miami. Listen as Devin talks about the excitement around this year’s Bears team, attending the games and keys to victory for Chicago. Jim Bob asks Devin about some of the crazy things in his career and beyond as the only Madden player to have 100 speed rating in the game how Devin actually raced a Cheetah and WON! Devin Hester will be out at the Super Bowl with The Mike Ditka’s Gridiron Greats Assistance Fund, helping with former players heathcare and also hilighting 17 years with Pork Rinds. Devin gives ways fans can win a trip to the BIG Game by going to www.PorkRinds.com and for tickets and info on Gridiron Greats events and efforts go to https://www.gridirongreats.org/ Stay tuned to The Jim Bob Show with Dane on WGN Radio and the ROAR Podcast Series and for the video version of this interview with Devin Hester check out   https://www.facebook.com/share/v/189fmXYXW8

Always WIN with the Undefeated Flavor of El Bandido Yankee, the Official Tequila of GameDay! For events, recipes and places for purchase go to www.elbandidoyankee.com

Nostra-Jim-Bob-us gives us his Bears, Packers playoff preview. This rare post season meeting of the two most historic, cornerstone franchises of the NFL brings a date with destiny for the resurgent, hopeful Bears and their success starved fan base. Listen as Jim Bob sets the stage and makes the wise and always winning prediction and pick! Stay tuned to WGN Radio and The Jim Bob Show with Dane for player interviews, guest features and the tales from the Tailgreeter Tailgates…and always Jim Bob’s WANNA Parlay picks of the week. Sign up for WANNA Parlay and enter code WGN to WIN your way to GameDay!

Always WIN with the Undefeated Flavor of El Bandido Yankee, the Official Tequila of GameDay! For events, recipes and places for purchase go to www.elbandidoyankee.com

In this episode of Booze Newz, Hudson Lindenberger sits down with the founder of The Muff Liquor Company, Laura Bonner to talk about how a family tradition turned into a modern Irish spirits brand—with a few unexpected turns along the way, including backing from Russell Crowe. We get into her grandfather’s poitín, the real story behind Muff’s medicine-style bottles, and what it’s actually like building a craft spirits business today without leaning on overblown origin myths. It’s an honest conversation about heritage, hustle, and how authenticity still matters—even when Hollywood gets involved. For more information on Laura, her story and The Muff Liquor Company, go to https://themuffliquorcompany.com/. Stay tuned for new Booze Newz episodes coming up as part of the ROAR Podcast Series on WGN Radio and read Hudson Lindenberger in Forbes at https://www.forbes.com/sites/hudsonlindenberger/

In this forward-looking and deeply practical episode, host Bo Kemp sits down with Bitcoin lawyer and digital-asset expert Joe Carlasare to unpack one of the most important shifts happening in global finance today: the rise of digital currencies and the movement some are calling the Great Reset. Far from theory or hype, Joe offers a grounded view of how Bitcoin, stablecoins, and emerging digital currencies are reshaping access to capital, transaction speed, and market opportunity. Together, Bo and Joe explore the rapid expansion of digital currencies and what the “Great Reset” really means for entrepreneurs and investors, how Bitcoin and stablecoins are being used right now by innovative operators to unlock capital and accelerate business growth, why real estate developers stand to gain from faster settlement, global liquidity, and borderless transactions as well as the competitive advantages early adopters are already experiencing in deal-making, capital raising, and market access. Hear as Bo and Joe share the legal, financial, and regulatory insights every entrepreneur should understand before integrating digital currencies into their strategy, and what the future of money could look like — and how to position yourself ahead of coming shifts in the global financial system. This episode is for entrepreneurs, real estate developers, and forward-thinking leaders who want to understand where money is headed — and how to harness Bitcoin and stablecoins to build smarter, faster, and more resilient businesses. Joe’s insights reveal why digital currencies aren’t just the future — they’re a present-day competitive edge.

In this reflective and forward-looking episode, host Bo Kemp closes out the year by addressing the real reasons most people fail to achieve the goals they set — not because of lack of ambition, but because of five predictable and universal objections. Drawing from the LifeDesyn System, Bo breaks down the five barriers that quietly derail progress: time, money, fear, doubt, and partner resistance. Rather than treating these as excuses, Bo reframes them as structural problems that require intentional design, clarity, and communication. This episode serves as both a personal audit of the year behind you and a strategic planning session for the year ahead. Bo explains why time must be protected and structured, how money functions as fuel—not the objective, why fear is best managed through systems and clarity, how doubt dissolves through small, repeatable wins, and why partner conflict is often rooted in surprise and uncertainty rather than disagreement. What You’ll Learn in This Episode: Why “not having time” is a design problem, not a scheduling problem, how to think about money as a tool for execution, learning, and opportunity, the difference between fear and danger — and how structure reduces both. Learn why doubt cannot survive evidence, and how small wins compound into confidence, and how to engage partners early to build support, sustainability, and trust. This episode provides the architecture of transformation — helping you turn reflection into execution and intention into momentum. If you’re serious about closing the gap between where you are and where you want to be in the coming year, this conversation will give you the framework to move forward with clarity and purpose.