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Real Life Investing With Jason & Rachel Wagner

Real Life Investing With Jason & Rachel Wagner

Written by: Jason & Rachel Wagner
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About this listen

“Real Life Investing” with Jason and Rachel Wagner is a multifaceted podcast that blends insights from real estate, entrepreneurship, family life, and political discussions. Known for their candid and engaging style, the Wagner’s explore how their conservative values shape their approach to both business and life. They often discuss their personal journeys in real estate, offering practical tips on topics like how to buy a house or investment property while navigating a challenging housing market.

In addition to real estate, the show frequently delves into entrepreneurial lessons, highlighting the importance of mindset, perseverance, and staying focused on long-term goals. They are open about the challenges they’ve faced and provide valuable advice for anyone looking to head into entrepreneurship or seek the best version of themselves.

Dinner table conversations are central to the podcast. The Wagner’s discuss their experiences balancing various topics that families face, while often featuring guests who share similar journeys. Political conversations are explored from a conservative perspective, particularly when they touch on how these beliefs influence their business decisions and personal growth.

With a blend of relatable stories and expert advice, “Real Life Investing” is a show that appeals to a wide audience, from aspiring entrepreneurs and real estate investors, to those seeking inspiration in their personal lives.

© 2026 Real Life Investing With Jason & Rachel Wagner
Economics Leadership Management & Leadership Personal Finance
Episodes
  • 74. There Is No Rushing Grief: A Story of 2nd Trimester Pregnancy Loss With Kayla Heiar
    Mar 25 2026

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    In this episode, Rachel sits down with our close friend Kayla Heiar as she bravely shares the story of losing her baby girl, Skye Marie, at 15 weeks. Kayla walks us through her pregnancy journey—from early ultrasounds and hopeful milestones to the devastating appointment where no heartbeat was found. She opens up about the shock and disbelief that followed, the need to seek confirmation before making next steps, and the emotional weight of choosing a D&E. Kayla also shares what the postpartum reality of miscarriage looked like for her, including the physical recovery, hormonal shifts, bleeding, body changes, and even the unexpected experience of her milk coming in.

    Throughout the conversation, we talk about the many ways grief shows up in everyday life—through reminders like keepsakes, travel plans, and the challenge of imagining the future after loss. Kayla shares how she and her family chose to name and honor their daughter, Skye Marie, through burial and personal pieces of remembrance. She also reflects on how loss affects spouses differently and what it means to continue parenting their living children while carrying the grief of the one they lost. With honesty and faith, Kayla discusses the tension of holding both gratitude and grief at the same time, learning to allow moments of joy without guilt, and the deep human desire for answers in the midst of unanswered questions. This episode is a tender and real look at pregnancy loss, the postpartum experience that often goes unspoken, and the hope and support that can help carry families through the waves of grief.

    Our hope is listeners going through a similar journey will find comfort in knowing they aren't alone.

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    1 hr and 16 mins
  • 73. The Unforgettable Impact of Charlie Kirk
    Sep 23 2025

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    Charlie Kirk's life was cut tragically short at just 31 years old, but his impact on American politics and conservative thought will endure for generations. We're still processing the shock of his assassination, which has rippled through communities worldwide and revealed deep fractures in our political landscape.

    Few figures have accomplished what Kirk did in such a short time. Founding Turning Point USA as a teenager without a college degree, he built a movement that gave voice to young conservatives on campuses across America. His approach was unique – engaging in difficult conversations with political opponents while maintaining a kind, open demeanor that invited dialogue rather than division. This combination of principled conviction and conversational tone made him remarkably effective and beloved by millions.

    What's been most striking in the aftermath is the range of reactions. While many mourned deeply – including people who never met him but felt connected through his content – others responded with indifference or even celebration. This troubling dichotomy points to a deeper crisis in our political discourse. The digital age has compounded these issues, with graphic footage spreading rapidly online and context-stripped quotes fueling misrepresentations of Kirk's actual statements.

    As we reflect on this tragedy, we're left with important questions: How do we protect ourselves from the psychological impacts of witnessing violence through our screens? Can we disagree with someone's politics while still acknowledging their humanity? And how do we begin healing a political culture that has become so venomous?

    Perhaps the most powerful moment came at Kirk's memorial service when his wife Erica forgave his assassin – a testament to the faith-centered values he espoused. As we move forward, the most fitting tribute to Charlie Kirk might be restoring the kind of respectful dialogue he advocated for, where disagreement doesn't devolve into dehumanization, and political violence is universally condemned.

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    52 mins
  • 72. Navigating Our First Eviction: A 10-Month Landlord Nightmare
    Sep 19 2025

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    Our first eviction experience turned into a year-long saga of legal hurdles, thousands in lost revenue, and unexpected emotional challenges. We navigate the complex process of evicting non-paying tenants from our commercial property in Chicago while balancing business decisions with human impact.

    • Notice requirements for tenant termination in Chicago (120 days for tenants who've lived there over 3 years)
    • Impact of problem tenants on other units and building conditions
    • Timeline from notice to actual eviction spanning nearly 12 months
    • Legal procedures including court dates, default judgments, and sheriff scheduling
    • Importance of not accepting rent after termination notice
    • Financial impact: over $10,000 in losses from legal fees and missed rent
    • Emotional reality of eviction day with six sheriff officers and social workers
    • Cash-for-keys as a potentially better alternative to formal eviction
    • Location matters - eviction laws vary significantly between different states and counties
    • Single-unit rentals carry higher risk compared to multi-unit properties

    If you're considering real estate investing, understand that evictions are sometimes unavoidable but should be your last resort. The financial and emotional cost makes cash-for-keys deals worth considering before entering the lengthy court process.


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    48 mins
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