Midway Business Podcast

AI Won’t Replace You… Unless You’re Doing the Wrong Work

Host Butch Zemar chats with Michael Kupchak—accountant, educator, fraud examiner, and youth sports coach—about a career path that runs from small family business to teaching at the University of Chicago. Michael shares how blending accounting with information sciences put him in the sweet spot for AI’s rise—not to replace humans, but to kill repetitive work so you can focus on the good stuff (like lunch).
He warns that in fraud, the biggest risk might be the person you trust most—kind of like whoever “manages” the office coffee fund. On generational shifts, today’s grads are more likely to question professors and expect work-life balance out of the gate.
Off the clock, Michael coaches youth sports and backs his kids’ dreams—whether engineering, SWAT team, or whatever they change their mind to next year. His advice: learn the numbers, but more importantly, learn to solve problems no one’s answered yet… because AI won’t do all your thinking for you.
For more information, please contact us at EliteBenefits.net or call 708-535-3006.
To contact Michael Kupchek IV: https://www.linkedin.com/in/mikekupchek/
 

How to Fix Your Business in Eight Days (Without Firing Everyone on Day One)

Host Butch Zemar sits down with Jamal Wolf, who went from being Circuit City’s #1 computer salesperson (back when selling a desktop was like selling a car) to running two companies—Chicago Smart Business Solutions and Chicago Smart Realty Solutions. His career detour wasn’t exactly voluntary; after corporate commission “restructuring” (aka, “we’re changing how you get paid, so you make less”) and the 2008 job market disaster, Jamal decided if people kept saying, “We’re afraid you’ll take our customers,” maybe he should—just legally, under his own logo.
Jamal walks us through his Eight-Day Plan, which starts with Day Zero—admitting you have no idea what you’re doing (kind of like most Monday morning meetings). From there, it’s about focusing on the right thing, testing it, scaling it, and making sure the instructions are so simple that anyone could follow them—because the moment you leave, someone will try to “do it their own way” and break it.
With stories ranging from turning a warehouse’s daily shipping from 60 to 1,000+ packages, to integrating AI so employees can “click less and coffee more,” Jamal proves process improvement isn’t just for massive corporations with color-coded org charts. Whether you want him to fix it and hand it back, or fix it and run it for you, Jamal’s point is clear: A solid process saves money, time, and possibly your sanity—especially when your current plan is just “hope nothing breaks this quarter.”
For more information, please contact us at EliteBenefits.net or call 708-535-3006.
To contact Jamal Wolfe on LinkedIn.

Your Data Just Got Held Hostage. Now What?

In this episode, Butch Zemar chats with tech attorney Lisa Gavin, who’s navigated everything from fintech to ransomware settlements (yes, that’s a thing). Lisa lays out what happens when a hacker locks down your data and demands crypto—hint: there’s no Liam Neeson, just consultants billing by the hour and your cyber insurer asking if you’ve “read the policy.”
She introduces tabletop drills—live-action crisis simulations where your leadership team roleplays disaster. No PowerPoints. No IT guy to save the day. Just real talk like: “What do we do if payroll gets hacked at 3 a.m.?” Spoiler: most companies have no clue. These drills help expose weak spots before a real breach does—and no, forwarding sketchy emails to your MSP doesn’t count as a plan.
If your Wi-Fi password is taped to the breakroom fridge and your incident response plan is “hope,” this episode is your wake-up call.
For more information, please contact us at EliteBenefits.net or call 708-535-3006.
 

How to Stop Paying for a Broken Healthcare System (Without Firing Your Broker… Yet)

In this episode, Butch Zemar chats with benefits vet Gary Blaum, who’s spent decades in the TPA and PBM trenches. Spoiler: PBMs were cooking the books, and Gary brought spreadsheets to the gunfight. After years of chasing down shady contracts, he found something better—Vitable—a fixed-cost primary care model that sends nurse practitioners to your employees’ homes. Yep, house calls are back, and no, it’s not 1942.
Employees love the zero copays. CFOs love the predictable costs. HR finally has a recruiting tool better than casual Fridays. With early diagnosis, real care, and a 3:1 ROI, this model doesn’t just bend the trend line—it dropkicks it.
As Gary says, “There’s no good reason not to do this.” Unless, of course, you’re emotionally attached to double-digit renewals.
For more information, please contact us at EliteBenefits.net or call 708-535-3006.

Beyond the Breaking Point: What Great Leaders Do Differently

🎙️ In this episode of the Midway Business Podcast, Butch Zemar dives into the unglamorous truth about why people give up too early — and no, it’s not just because Netflix released another season of something shiny. From childhood dreams of becoming an astronaut (thanks for nothing, Navy recruiter) to navigating the chaotic galaxy known as health insurance, Butch shares battle-tested stories about how success isn’t a straight line — it’s more like a drunken loop-de-loop through doubt, detours, and deductible spreadsheets. Spoiler alert: most people don’t fail — they just stop showing up.
 
Using Alex Ovechkin’s record-breaking goal streak as a metaphor (because who doesn’t love hockey analogies), Butch reminds us that even the greatest need assists — from line mates, life partners, and yes, even LinkedIn followers. Whether you're chasing a business goal, a personal best, or just trying to survive open enrollment season with your sanity intact, this episode is your wake-up call to stop ghosting your goals. Grab your calendar, call your therapist, and for the love of benefits, journal your action steps. Because the only thing worse than failing is hiring a broker who gives up faster than your New Year’s resolution.
 
For more information, please contact us at EliteBenefits.net or call 708-535-3006.

Dear CFO: You Analyze Everything Except the One Thing Bleeding Cash

In this episode of the Zemar Podcast, Butch Zemar takes us on a wild ride from outdated Navy aircraft to outdated employer health plans — because apparently, both refuse to die quietly. Using a broken FLIR pod as a metaphor (and no, not the kind of pod you cry in after seeing your renewal increase), Butch breaks down why starting from scratch isn't such a bad thing — whether it's rewiring aircraft or rebuilding your benefits strategy. If NASA can reprogram a space capsule with duct tape and whiteboards, your company can certainly rethink its January 2026 health plan before it's too late (yes, even in July 2025).
Bonus tip: your broker might already be on summer vacation, but that doesn’t mean your fiduciary duty is too.
He compares the health insurance renewal process to a family board game — except in this one, the rules change annually, the dice are rigged, and your CFO keeps trying to skip to the end without reading the instructions. Butch lays out the roadmap: ditch the cookie-cutter plan, start removing predictable expenses like doctor visits, challenge your broker on drug rebates, and don’t be afraid to ask “why are we still doing it this way?” If you can control office supplies and taxes, you can control your health plan. And if all else fails, channel your inner Captain Jack Sparrow, grab your sword (or spreadsheet), and charge the Kraken — because it’s time to fight back against bad renewals. 💥💼🩺
 
For more information, please contact us at EliteBenefits.net 708-535-3006

Because ‘We’ve Always Done It This Way’ Is Clearly a Financial Plan

In this episode, Butch Zemar delves headfirst into the bureaucratic complexities that hinder small and mid-sized businesses when it comes to managing employee benefits. He explores why some companies act like deer in headlights when faced with cost-saving opportunities — usually because emotions are driving the bus while logic is locked in the trunk. Butch calls out the common bottleneck culprit: the business owner.
Spoiler alert — if you're still personally reviewing dental network maps in Q3, you're probably the problem. Drawing comparisons to giants like Musk and Bezos, Butch reminds us that successful leaders make bold moves, trust data over feelings, and don’t panic just because the toothpaste is running low.
With equal parts insight and satire, Butch urges business leaders to ditch the "just survive" mentality and start playing to win. He shares real-world examples of companies that left six figures in cash savings on the table because they were too emotionally attached to outdated plans.
From letting go of tasks to trusting the math over your gut, the episode lays out a simple roadmap: stop hoarding responsibility like it's Halloween candy, delegate like a grown-up, and treat your benefits strategy like it actually impacts your bottom line — because it does. If you're tired of watching your health plan bleed cash while your CFO plays whack-a-mole with invoices, this episode is your wake-up call.
For more information, please contact us at EliteBenefits.net 708-535-3006

We Tried Nothing and We’re All Out of Ideas - But Hey, At Least HR Still Has Bagels

Let’s be honest—setting goals is easy. Achieving them? That’s where CFOs start twitching and HR hides under their desks.
In this episode, we get a masterclass in corporate reality checks. Think you're overworked? Imagine trying to hit business goals while your benefits plan is hemorrhaging money like a rookie finance intern let loose in Excel.
Butch Zemar breaks down the art of not giving up too early—unless, of course, you enjoy 54% renewal increases and the warm, fuzzy feeling of budget panic. He uses stories from his own journey—complete with dreams of becoming an astronaut and disappointing DIY projects—to prove that brute force and wishful thinking don’t belong in your benefits strategy.
Now, if your current broker is telling you “it’s just the market,” you might want to get that second opinion before your healthcare plan starts moonlighting as a financial sinkhole. Zemar shares how one company saved $400,000 by switching funding models—yes, real money, not Monopoly cash—and another that avoided a catastrophic increase by actually using strategy (shocking, we know). The takeaway? Stop throwing darts at your health insurance plan blindfolded. There’s a better way—and no, it doesn’t involve spreadsheets soaked in tears.
For more information, please contact us at EliteBenefits.net 708-535-3006

Brokers, Spreadsheets, and Other Things That Haven’t Changed Since 1997

This episode dives into the all-too-familiar boardroom ritual: reviewing the company's health plan with furrowed brows, followed by the annual shrug and “let’s just raise the deductible again.” Butch Zemar calls out this Groundhog Day behavior with a fresh prescription—less déjà vu, more innovation. Drawing inspiration from Big Hero 6 (because who says insurance can’t be animated?), he challenges businesses to think differently.
Brokers still clinging to 1990s playbooks?
CFOs allergic to change?
It's time for a reality check and possibly a cartoon intervention.
Butch Zemar walks us through a case study that would make even the most cynical auditor perk up: a company shaved nearly $300K off their health costs over six years by doing the unthinkable—collaborating with their accountant. Even when claims spiked 52%, their strategy cut it back to 22%. The message is clear: switching carriers isn’t a strategy, and hope isn’t a cost containment tool. Tune in to learn why your accountant might be the real superhero you’ve been ignoring—cape not included.
 
For more information, please contact us at EliteBenefits.net 708-535-3006

Skate Your Lane: Beer League Strategies for Boardroom Survival

In this episode, we lace up the skates, tape our sticks (badly), and take a hard-checking look at how beer league hockey can teach business professionals more than a dozen leadership seminars and a thousand "synergy" emails ever could. What starts as a midlife crisis on ice turns into a full-on MBA in grit, leverage, and learning not to chase the puck—or the next shiny business trend.
Between getting yelled at by semi-retired goalies and misplaying every position imaginable, the lessons come fast, slippery, and slightly bruised. Spoiler: brute force rarely wins—unless your KPI is “most time spent in the penalty box.” From boardrooms to breakaways, we explore how playing your position, using the right tools, and not mistaking motion for progress are key to scoring real wins. Whether you're a sales rookie, a startup founder, or just trying to survive the inbox power play, this one’s for you. Work smarter. Skate harder. And for the love of all things strategic—stay out of the crease.
 
For more information, please contact us at EliteBenefits.net 708-535-3006