He left Jamaica, took a job he didn’t want, battled depression, and nearly missed the purpose that would shape his life. Andre shares the story behind the faith, resilience, and leadership that carried him from survival to ministry - and why the hardest seasons can become the most meaningful ones.

Born and raised in Jamaica, Andre grew up in a church-centered home where faith was woven into everyday life, but so was hardship. He talks candidly about childhood without running water or steady electricity, the grind of helping care for animals before school, and how those early years built the work ethic and creativity he still relies on today.

Andre also tells the unexpected love story that connected him to the United States, the Crossing Church, and eventually Quincy. What starts as a ministry story quickly becomes something deeper: a raw look at culture shock, the pressure of adapting to a new world, and the difficult 11-month season that left him questioning whether he had made a mistake.

You’ll discover:

How a thick Jamaican accent turned Andre into the “crazy Jamaican” on stage, and forced him to become a stronger communicator

Why his post-internship billing job became one of the darkest stretches of his life

What depression, grief, and homesickness taught him about trust, calling, and resilience

How mentoring, delegation, and leadership changed his approach to ministry

Why he believes the real work is not performance, but investing in the next generation

Andre shares what it looks like to lead youth and children with purpose, especially when students are battling addiction, pornography, identity issues, and broken family support far earlier than most adults realize. He explains why baptism moments matter so deeply, why the church must raise up young leaders now, and how one faithful conversation can ripple through a family, a friend group, and an entire future.

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Quincy landlords are about to feel the ripple effects of a policy change, and Clayton Roll explains why the real fix may be the opposite of what everyone expects. If you care about housing, property rights, or what happens when government policy meets real-world ownership, this conversation will grab you fast.

Clayton shares the path that took him from St. Louis house hacks to small-town real estate, and then into building Rolling Operations after getting fed up with terrible dumpster service, hidden costs, and slow response times. What starts as a story about rehab projects turns into a bigger lesson about customer experience, entrepreneurship, and how one frustrating industry became an opportunity.You'll discover:

Tim Holloway and Jackie Weisenburger push the conversation into the tension every city faces: how do you stop slumlords without punishing the people who are actually reinvesting in housing? Clayton makes the case that bad properties should be targeted directly, while good landlords should be incentivized to improve homes, keep rents lower, and keep older neighborhoods alive.

This episode gets into the economics behind rentals, property taxes, depreciation, code enforcement, and the unintended consequences that often hit tenants, landlords, and taxpayers all at once. It is a practical, local conversation with broader implications for any community trying to balance affordability with accountability.Essential listening if you want a grounded take on housing policy, small business, and what it really takes to keep old homes, and local neighborhoods, from falling apart.

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When leadership feels lonely, marketing feels expensive, and life starts moving too fast, Heather Risenhoover has a different answer: slow down, build real community, and make space for people to actually belong.

The Quincy native shares how she turned a career in retail operations into a leadership journey that now includes running Target, launching a local coffee concept, and building a business rooted in faith, connection, and purpose.Heather opens up about coming home to Quincy, raising a blended family, and what it took to move from a 16-year-old mall employee to senior retail leader across seven states and 11 stores. She also reveals how a LinkedIn connection helped bring her back to Quincy to open the local Target, and why she saw an opportunity to create something smaller, warmer, and more human with The Mercantile.

In this episode, you’ll discover:

Heather also talks candidly about the emotional weight of leadership, the value of accountability partners, and the need to step away from the constant pressure of social media and negative news.If you’ve ever felt overwhelmed by the pace of modern life, pressured by social media, or curious about what it takes to build a business with soul, this conversation will hit home.

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Cancer, divorce, job loss, and the pressure to keep moving nearly flattened Jake. What came out the other side is a radically different way of living - slower, calmer, and far harder to shake. Jake sits down with Tim Holloway to share the moment his life split into a “first life” and a “second life,” and why surviving stage 4 lymphoma forced him to rethink identity, boundaries, and what actually matters when the noise gets loud. If you’ve been running on stress, saying yes to everything, or tying your worth to work and output, this conversation hits where it hurts - and where it can heal.You’ll hear:

Tim and Jake also get into the deeper side of manhood, self-awareness, and the cost of living in constant reaction mode. Jake opens up about the relationships he had to reevaluate, the pressure he once put on the people around him, and the surprising lesson he’s now passing to his son: authenticity lasts longer than hustle.Jake shares the role of faith, the power of patience, and why he now measures a good day by whether he can breathe, stay grounded, and show up well for the people he loves. It’s a conversation about survival, but more than that, it’s about learning how to live after everything you thought defined you is gone. Essential listening if you need a reset, are navigating a hard season, or want a grounded reminder that peace is not weakness - it’s strength.

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Roof age, claim history, and home maintenance are quietly making or breaking insurance policies right now - and most homeowners do not realize it until they get denied, canceled, or stuck with a much higher premium. Tracy Kiefer, the "insurance lady" at O'Brien Insurance, breaks down what insurers are actually looking for and why a house that seems fine on the surface can become uninsurable fast.

Tracy shares how a career that started in her dad's office grew into decades of independent insurance work across Quincy and the Tri-State area, from hand-calculating quotes out of books to navigating today's tougher underwriting rules. She explains why roofs, siding, electrical boxes, HVAC age, and even a missing shingle can trigger major problems when a property is inspected.You'll discover why multiple homeowner claims in a five-year window can wreck your options, why "just turning in a claim" can backfire later, and how insurers separate real losses from maintenance issues.

Jackie Weisenburger brings the real estate perspective, showing how these insurance headaches are already affecting home sales, appraisals, and closings. Tim Holloway keeps the conversation moving with questions every homeowner, buyer, and seller should be asking before it's too late.Tracy also pulls back the curtain on Illinois' license plate insurance monitoring system, including how a completely unexpected suspension can happen even when you think everything is in order.

That alone makes this episode essential listening if you drive in Illinois, own property, or have ever assumed your insurance company will catch everything for you.Then the conversation turns personal. Tracy opens up about her cancer journey, the faith and prayer that carried her through, and the mindset that helped her stay grounded through one of the hardest seasons of her life. It is a story about resilience, community, and the practical wisdom that comes from surviving both business challenges and personal ones.If you own a home, are buying one, work in real estate, or simply want to avoid expensive surprises, this episode gives you the kind of advice that can save you money, stress, and a whole lot of trouble later.

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A flood, a financial crash, a death, and a move that changed everything - Paige Mitts turns survival into a blueprint for building a life on purpose. If you have ever been forced to reinvent yourself, this conversation will hit hard.Tim Holloway and co-host Jackie Weisenburger sit down with Paige for a story that starts with an Air Force childhood shaped by Vietnam, family sacrifice, and constant movement, then follows her through 40 jobs, a career in financial services, and the kind of loss that strips identity down to the studs. Paige shares how losing a partner, navigating the 2008 crash, and surviving a house flood in Quincy pushed her to rethink control, calling, and what it actually means to be at peace.

You'll discover:

Paige also opens up about caregiving for her parents, the emotional cost of crisis after crisis, and why Quincy became home in a way nowhere else ever had. From the rhythm of the road to the reality of staying put, this episode connects the dots between reinvention, resilience, and finding a mission that actually fits your life.And then there’s the book. Paige introduces her Neurosparkle Manifesto, a project rooted in her own gestalt way of processing the world and inspired by the birds, bay, and people of Quincy. It’s a conversation about language, identity, neurodivergence, and the power of telling the truth in a way only you can tell it.Essential listening if you’re rebuilding after loss, questioning your path, or trying to turn lived experience into something bigger than survival.

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A cross-country move, a sight-unseen house, and a kitchen so filthy it nearly stopped everything - this episode is a brutally honest look at what it takes to start over and build a life with real roots. If you’ve ever wondered whether the "laptop life" is freedom or just organized chaos, this conversation will hit home.Tim Holloway tells the full story of how he and his wife packed up their family, drove across the country, and arrived at a house they had only seen on FaceTime - only to find roach damage, hidden problems, and a closing day they could not back out of. What follows is part survival story, part renovation journey, and part reflection on the cost and payoff of choosing an unconventional life.

You’ll discover:

Tim also opens up about the emotional side of building a life on the move - from leaving behind a supportive community in Texas to finally putting down roots in Quincy, and from living in rural quiet to planning trips across England and Europe. Along the way, he and his wife reflect on what it means to raise kids while working remotely, staying present for sports and events, and making a "laptop life" actually work.This episode is especially compelling for anyone craving more freedom, families considering a move, or listeners who want the real story behind remote work and unconventional living. It’s funny, honest, and surprisingly inspiring - a reminder that building the life you want usually starts with risk, a little chaos, and the courage to keep going.Perfect for listeners who love real-life stories about relocation, home renovation, family, and the freedom to work from anywhere.

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A Match.com connection turns into a fast-moving love story, a move across the country, and the kind of hard reset that forces two people to build everything from scratch.

If you’ve ever wondered how a relationship, a family, and a business can survive when life blows up all at once, this one’s for you.

Tim Holloway and Jamie trace the real story behind their relationship—from the awkward first messages and the “poo or get off the pot” date pressure to the Lake Arrowhead walk that changed everything.

What starts as a funny, romantic rewind quickly becomes something deeper as they talk honestly about timing, trust, blended families, and the split-second decisions that shape a life.

You’ll hear how:

Tim and Jamie also open up about the ripple effects of starting over in Sandpoint and Coeur d’Alene, why they left California, how C*vid reshaped their family plans, and why Quincy eventually became the next destination on the map.

It’s a story about love, regret, resilience, and the strange way a crisis can become the beginning of something bigger.

Essential listening for anyone who loves real relationship stories, entrepreneurial pivots, or the behind-the-scenes moments that never make it into the highlight reel.

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She left a hard marriage, rebuilt her confidence, and met her next chapter through a dating app message she almost swiped away.

This is the story of Jamie Holloway—a teen mom turned self-reinvention machine—and the moment everything started to change.

Growing up in small-town Washington State, Jamie was surrounded by boredom, conservative expectations, and a culture where sex was taboo—but consequences were everywhere.

She shares what it was really like becoming a mother at 16, raising two kids by 20, and trying to survive an adulthood she was never ready for.

You’ll hear how childhood abuse shaped her self-worth, why she stayed too long in a marriage that looked fine from the outside, and how working alongside Wes Chapman pulled her into a completely different world.

Along the way, she found herself in rooms with names like Dr. Drew, Randy Jackson, Maggie Q, and other influential voices—all while quietly rebuilding the person she thought she had lost.

We break down:

Then comes the part that sounds almost too perfect to be true: the Match.com message that changed everything.

This episode is for anyone who has ever wondered if they missed their chance to become who they were meant to be.

Jamie’s story is proof that confidence can be rebuilt, identities can be rewritten, and a brand-new life can begin with one brave decision.

Perfect for listeners who love raw transformation stories, unfiltered family history, and the kind of episode that becomes more honest the deeper it goes.

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John Bertoni’s journey to becoming a home inspector was anything but predictable.

After high school, John worked in telecommunications construction, traveling across Michigan, Texas, and Florida. He later joined the Army, where he trained as a helicopter turbine engine mechanic. Military life was challenging, but it developed the discipline, resilience, and mechanical knowledge that would serve him throughout his life.

After leaving the Army, John worked for a custom home builder in Wisconsin. That experience gave him a deeper understanding of residential construction and eventually opened the door to home inspection.

When John moved to Quincy, Illinois, he worked at the Illinois Veterans Home while holding several additional jobs to provide for his family. In 2006, he took another courageous step and launched his own home inspection business.

Home inspection became the perfect combination of John’s interests. He enjoys understanding how homes are built, solving problems, and helping people make informed decisions. Because buying a home can be stressful, John approaches every inspection with patience and empathy. His reports do more than identify defects—they help homeowners understand their property, its systems, and its future maintenance needs.

John’s success did not come without a cost. At one point, he was completing hundreds of inspections each year and working long hours. Eventually, he realized his work-life balance needed to change. With the support of his wife, Sherry, he chose to focus fully on his business while building a life that better reflected his priorities.

John also speaks openly about grief and the heartbreaking loss of his daughter, Amy. He shares the pain of not knowing everything she was experiencing and the long process of learning how to carry that loss. Prayer, time in nature, meaningful memories, and honest conversations with trusted people have all played a role in his healing.

His advice to anyone walking through grief is simple: Do not bottle it up. Talk to someone. Sharing your pain is not a sign of weakness. It creates space for support, connection, and healing.

In this episode, John shares:

John’s story reminds us that success is not measured only by income, accomplishments, or how much work we can carry. It is also found in faith, resilience, meaningful relationships, serving others, and finding the courage to keep moving forward—even after life changes forever.

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