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Real Life Investing With Jason & Rachel Wagner

Real Life Investing With Jason & Rachel Wagner

Hosted by Jason & Rachel Wagner

BusinessEntrepreneurship
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Episodes

75

Latest episode

Jun 2026

Language

EN-US

About the show

“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.

Listen to episodes

60 recent
June 11, 20261 hr 13 min

75. From Hospital Pressure to Thriving at One: Our Son’s First Year Unvaccinated

Send us Fan MailAfter a year-long hiatus raising their third child and stepping into homeschooling, Jason and Rachel Wagner are back with a raw, honest update on their unvaccinated son Wes.In this episode, they share what the first year of life has looked like for their completely unvaccinated son — including tracking every sick day, zero fevers, and how his health has compared to their vaccinated daughters. Jason and Rachel walk through their decision-making process for each vaccine on the standard schedule, the real risks they weighed, and why they ultimately chose to decline them all. They also open up about the pressure they faced in the hospital, the role of faith in their choices, and what it means to truly understand risk versus reward as parents.Whether you’re a parent questioning the childhood vaccine schedule, curious about natural immunity, or simply want to hear a candid, faith-informed conversation about real-life health decisions, this episode offers transparent insights without judgment. Tune in for an encouraging discussion on trusting God’s design, supporting a child’s immune system, and making informed choices that align with your values.Listen now and let us know what you think in the comments!

March 25, 20261 hr 16 min

74. There Is No Rushing Grief: A Story of 2nd Trimester Pregnancy Loss With Kayla Heiar

Send us Fan MailIn 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.

September 23, 202551 min

73. The Unforgettable Impact of Charlie Kirk

Send us Fan MailCharlie 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.

September 19, 202548 min

72. Navigating Our First Eviction: A 10-Month Landlord Nightmare

Send us Fan MailOur 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 propertiesIf 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.

August 14, 20252 hr 22 min

71. How Private Lending, AI, & Midterm Rentals Create Freedom With Jennie Berger and Tristan Lora

Send us Fan MailIn this captivating episode of Real Life Investing, Jason and Rachel Wagner sit down with powerhouse duo Jennie Berger and Tristan Lora for a conversation that blends real estate savvy, entrepreneurial resilience, lifestyle design, and some truly unforgettable stories.Jennie shares her inspiring journey from high-stakes condo development and house flipping to building a thriving private lending business. She opens up about lessons learned from challenging projects, the art of calculated risk-taking, and how she structures deals to protect her capital—plus the surprising role her self-directed Roth IRA plays in her lending portfolio. Tristan jumps in with insights from his high-energy career in live events and race car street production, showing how creativity, adaptability, and AI tools fuel his work.Beyond business, the episode explores their shared commitment to health, plant-based living, and intentional lifestyle choices. The conversation flows into midterm rental strategies, navigating tenant relationships, and the balance between financial returns and personal freedom. Along the way, listeners are treated to hilarious and heartfelt anecdotes—ghost stories, “slow-play” romance, and even the science of hugs—that reveal the warmth and authenticity behind their success.Whether you’re a real estate investor, entrepreneur, or someone seeking inspiration to design a healthier, more intentional life, this episode delivers a rare mix of actionable advice, personal wisdom, and pure entertainment.IG: @Propertypeoplellc

July 14, 20251 hr 13 min

70. Unlocking VA Loan Secrets with Dubois Toy

Send us Fan MailWhen veteran Dubois Toy received a check for $2,600 at his closing table after buying a $369,000 property, he knew he'd stumbled onto something extraordinary. With just $400 out-of-pocket, he'd unlocked the hidden potential of the VA loan that most veterans never discover.As a former ethical hacker, Toy brought his methodical approach to finding loopholes to the world of real estate investing. "I read 2,000 pages of the VA lenders handbook," he reveals, explaining how this deep dive uncovered game-changing strategies most loan officers don't even know about. The most shocking revelation? Only 35% of veterans ever use their VA loan benefits, leaving billions in potential wealth-building opportunities untapped.The conversation explodes with practical insights about maximizing veteran benefits—from getting property tax exemptions through disability ratings to the little-known technique of partnering multiple veterans together to purchase buildings far beyond the standard 4-unit limit. Toy breaks down how creative financing allowed him to acquire multiple properties with zero down payment and explains how veterans can stack tax advantages through strategic house hacking.Beyond real estate strategies, Toy shares powerful resources for veterans struggling with housing, offers book recommendations that transformed his mindset, and discusses the stark differences in benefits between various states. His passion for helping fellow veterans navigate what can be an overwhelming system shines throughout the episode.Whether you're a veteran looking to maximize your benefits or simply someone interested in creative real estate strategies, this conversation reveals how reading the fine print and questioning conventional wisdom can unlock extraordinary opportunities. What military benefit could you be missing out on right now?Resources:🏠 VA LOAN & HOUSE HACKINGVA Loan Program Overview (0% down, eligibility, benefits):🔗 https://www.benefits.va.gov/homeloans/VA Buyer’s Guide (PDF) – Understand the VA home loan process:🔗 https://www.benefits.va.gov/homeloans/documents/docs/VA_Buyers_Guide.pdfHouse Hacking with a VA Loan (renting by room/unit strategy):🔗 https://veteran.com/house-hacking-va-loan/VA Jumbo Loan Explanation (limits above conforming loan):🔗 https://www.veteransunited.com/valoans/va-jumbo-loans/VA Energy Efficient Mortgage (EEM) – Upgrade your property:🔗 https://www.veteransunited.com/valoans/va-energy-efficient-mortgage/VA Renovation Loan (similar to FHA 203k):🔗 https://www.veteransunited.com/valoans/va-rehab-loans/🧾 PROPERTY TAX EXEMPTIONS (CHICAGO / COOK COUNTY)Cook County Veterans Property Tax Exemption (70%+ disabled = full exemption):🔗 https://www.cookcountyassessor.com/veterans-disabilities-exemptionReturning Veterans Exemption (recently returned from active duty):🔗 https://www.cookcountyassessor.com/returning-veterans-exemptionDisabled Veterans Homestead Exemption Details (State of IL):🔗 https://www2.illinois.gov/veterans/services/Pages/property-tax-relief.aspxShoot Dubois a message on FB if you want to ask questions or get in contact!https://www.facebook.com/share/16CfS5xbFf/?mibextid=qi2OmgFor additional resources, click here.

May 24, 20251 hr 54 min

69. Standing Your Ground: Why We Declined Standard Newborn Hospital Protocols

Send us Fan MailWe recently welcomed our son Wes Michael Wagner and share our deeply personal journey through childbirth in a rapidly changing healthcare landscape, where we declined nearly all standard hospital protocols for newborns.In this episode we discuss:• Detailed look at RhoGAM shots and our decision to decline despite significant pressure from medical staff• Analyzing the risk factors of Group B Strep and antibiotics versus protecting the microbiome• How vitamin K shots are linked to jaundice and other risks according to manufacturer package inserts• Discussion of the new MAHA report that questions the American vaccination schedule• Navigating religious exemptions and standing firm on our decisions during labor• Hospital pressure tactics and how we researched each decision thoroughly• The striking observation that our newborn had the lowest risk of jaundice of our three childrenWe encourage you to research thoroughly, understand your personal risk factors, and make informed decisions that align with your beliefs. Whatever choices you make, being educated about both benefits and risks is crucial for proper informed consent.

May 5, 20251 hr 10 min

68. Berry Yo & the Heart of Arlington Heights: A Story of Grit, Frozen Yogurt, and Community with Sheila Henneman

Send us Fan MailIn this heartwarming episode of The Real Life Investing Podcast, Jason and Rachel Wagner sit down with Sheila Henneman, the beloved owner of Berry Yo Frozen Yogurt in downtown Arlington Heights, IL.Sheila shares her remarkable journey from being a stay-at-home mom to becoming a thriving entrepreneur with one of the most cherished local businesses in the community. You'll hear how she:Started a frozen yogurt business with no prior experienceSurvived the brutal impact of COVID with the help of her communityBuilt a business that hires and mentors local teensChose to not franchise, keeping Berry Yo a true community gemIs now experimenting with high-protein frozen yogurt using First Phorm productsRaised her kids with work ethic, integrity, and heart (including 75 Hard champion Paige!)Whether you're a small business owner, a parent, a dreamer, or just love a good underdog story—this episode will inspire you to follow your gut, serve your community, and persevere through anything.Connect with Berry Yo or Book an Event Visit: https://www.berry-yo.com Email: sheilahenn9@sbcglobal.net Call: 224-735-3112 Like, comment, and share this episode with someone who needs a dose of entrepreneurial inspiration! Subscribe for more real-life stories of grit, growth, and getting it done.

April 8, 20251 hr 28 min

67. The Milford Method: How To Create Meaningful Connections Where You Live with Matt and Katie Milford

Send us Fan MailWhat if the secret to building deep community in our disconnected world was hidden in plain sight? Matt and Katie Milford—known as the "connectors" of their Arlington Heights neighborhood—reveal their formula for transforming neighbors into friends and acquaintances into family.The Milfords share how their strategic decision to live near downtown, despite the higher cost, put them in proximity to like-minded, socially-oriented people. "When you rapidly surround yourselves with people who are in the same location, roughly the same age, popping out kids at the same time, and have similar interests, you naturally create friendships," Matt explains. This intentional choice creates the repeated interactions—approximately 10-30 needed to form a friendship—that happen organically when you regularly cross paths at parks, downtown areas, or while doing yard work.Their annual gatherings have become neighborhood legends. Their Fourth of July party invites over 100 people to watch the parade from their yard—complete with a refrigerator rolled into the driveway and 200 hot dogs. The Christmas party they rescued from cancellation brings 150 neighbors together during winter months when community connections typically hibernate. Their block parties transform their street into day-long celebrations ending with neighbors sharing whiskey and cigars until 2am.Beyond parties, the Milfords share their unique parenting philosophy, balancing personal growth with family time, and insights from Matt's former motorcycle garage business. They candidly discuss the challenges of building community while maintaining individual identity—something they've mastered through color-coded family schedules and designated alone time for each parent.Whether you're new to a neighborhood or looking to deepen existing connections, the Milfords offer a refreshingly simple roadmap: be visible, be curious, and be willing to initiate. In a world increasingly dominated by digital connection, they remind us of the irreplaceable value of face-to-face community.

March 13, 20251 hr 59 min

66. Unfiltered Success: Wonderful Togbey on Building A Real Estate Empire, 75 Hard, and Credit Card Mastery

Send us Fan MailIn this inspiring episode, Jason and Rachel Wagner sit down with the multifaceted Wonderful Togbey—a successful Chicago real estate investor, 75 Hard enthusiast, and master of credit card hacking. As an immigrant from Togo, West Africa, Wonderful Togbey shares his incredible journey of moving to the U.S. at 16, building a thriving real estate portfolio from scratch, and balancing a full-time job, family life, and global travel.Kicking things off with his experience tackling the grueling 75 Hard program in 2021, Wonderful reveals a surprising twist. From there, the conversation dives into his real estate adventures: starting with a house hack in Omaha, navigating tenant nightmares (think Walmart parking lot deals and stolen copper), and scaling up to a million dollar commercial property in Chicago’s Washington Park. With transparency as his superpower, Wonderful doesn’t shy away from the battle scars—flooded basements, evictions, and $200,000 budget overruns—proving real estate’s forgiving nature rewards those who persevere.Wonderful drops game-changing tips on credit card point hacking, showing how he turns everyday expenses into business-class flights to Togo and Spain using tools like Seats.aero and ChatGPT. Whether you’re a real estate newbie or a seasoned investor, this episode is packed with grit, practical wisdom, and a reminder that the sweetest rainbows follow the toughest storms.Follow Wonderful’s journey on Instagram @mrwonderfulinvests

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