Real Life Investing With Jason & Rachel Wagner

Jason & Rachel Wagner
  • 3.9 (11)
  • Entrepreneurship
  • Updated Weekly

“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. 

  1. Aug 6 ·  Video

    80. Why The Tax Code Rewards Property Owners With CPA Ryan Bakke

    Send us Fan Mail Taxes can quietly decide whether a rental property feels like a win or a grind, and most investors never get a clear explanation of the rules that matter. We bring on CPA Ryan Bakke to translate real estate tax strategy into plain English and show how everyday W-2 earners can still benefit from rental income, deductions, and depreciation without needing to be a full-time investor. If you’ve ever heard “real estate investors don’t pay taxes” and wondered what’s actually legal, this conversation gives you the framework to spot the real levers. We dig into why rental income is treated differently than wages, including the overlooked impact of avoiding payroll taxes like Social Security and Medicare on rental profits. Ryan breaks down “paper losses” and why depreciation can reduce taxable income even when a property is appreciating. We also unpack Real Estate Professional Status, what the 750-hour and more-than-half-time tests really mean for couples, and when it could be worth having one spouse shift their work toward real estate for meaningful tax savings. From there, we get tactical on big decision points: the primary residence capital gains exclusion, the 2-out-of-5-year rule, and the three-year window that may let you rent out a former home and still sell it tax-free. We talk house hacking, how the 121 exclusion and a 1031 exchange can work in the same deal, and why 1031 timing can be risky with 45-day identification rules and negotiation pressure. Finally, Ryan explains cost segregation studies, how they accelerate depreciation, and why land value versus building value can dramatically change your tax benefits and after-tax returns. Connect with Ryan Bakke, CPA  LinkedIn: https://www.linkedin.com/in/ryanbakkecpa  Instagram: @ryanbakkecpa   X (Twitter): @RyanBakkeCPA   Facebook: Ryan Bakke CPA   TikTok: @ryanbakkecpa Community / Referral Program: SKOOL – skool.com/taxes

    80. Why The Tax Code Rewards Property Owners With CPA Ryan Bakke

  2. Jul 28 ·  Video

    79. Our First Year Of Homeschool

    Send us Fan Mail We share what surprised us most after a full year of homeschooling our oldest and why we decide to bring our second child home too. We break down Classical Conversations, our daily routine, and the deeper reasons we value faith, freedom, and protecting confidence during the early years.  • deciding to homeschool after seeing pressure and frustration build  • how homeschooling changes when a second child stays home  • balancing work from home with kids learning at the kitchen table  • why kids often choose to do school on their own  • how to pick a homeschool curriculum without getting stuck  • what Classical Conversations is and how community day works  • our two-hour homeschool schedule with songs then seat work  • handling the mom as teacher authority challenge  • rebuilding confidence after early testing and classroom stress  • socialization myths, planning friendships, and peer influence risks  • limiting screens, avoiding early tech addiction, and reducing cyberbullying exposure  • using financial freedom to build a flexible family schedule  If you found any value in the show, please share it.

    79. Our First Year Of Homeschool

  3. Jul 20 ·  Video

    78. House Hacking Mastery: Rent-by-Room Secrets with Victor So

    Send us Fan Mail Join Jason and Rachel Wagner on the Real Life Investing Podcast for an inspiring conversation with Victor So — a pharmacist turned powerhouse real estate investor & agent, content creator, and family man. From house hacking his way into multiple properties, mastering rent-by-room and midterm rentals, to using creative financing (including a zero-down partnership deal) and building a mini property management system with his cleaner/landscaper team, Victor reveals how he scaled to 11 doors while still working his W-2. He also shares the raw side of putting himself out there: a simple park video that went viral, brought hundreds of new followers, and triggered nasty threats and doxxing attempts. Plus, fitness talk (all-state volleyball roots and benching 315), balancing family life with three kids, and thoughtful insights on vaccines from a pharmacist’s perspective. This episode is full of practical strategies, mindset shifts, and encouragement to keep creating content even when the haters show up. If you’re looking for creative ways to generate cash flow, optimize properties, or build resilience as an investor, you don’t want to miss this one. 👉 Follow Victor for more Chicago-area investing and neighborhood gems: @VictorSoRealEstate Victor's Bio: Victor is a pharmacist-turned-real estate investor and agent passionate about helping clients build wealth through strategic real estate investments. Drawing from his own experience owning and managing 11 rental units, he provides practical guidance to investors at every stage of their journey. Whether you’re buying or selling traditionally or exploring creative strategies like house hacking, co-living, short-term rentals, or other investment opportunities, Victor is committed to helping you achieve your financial goals with confidence. Follow Victor on Instagram: @VictorSoRealEstate

    78. House Hacking Mastery: Rent-by-Room Secrets with Victor So

  4. Jul 13 ·  Video

    77. Buying Site Unseen, Creating Content, and Arguing Zillow Vs Compass With Grady Schmidt

    Send us Fan Mail You can do a lot with a steady W-2 paycheck if you’re willing to get a little uncomfortable. We sit down in The Nook with Grady Schmidt, a Chicago-based investor who starts with a garden-unit condo and turns it into a no-frills house hack, then scales into buying site unseen Indiana rentals while working in finance at Google. He shares the exact choices that helped him move fast, including why he used 25% down, how he picked Midwest markets like East Chicago, Michigan City, and South Bend, and what he wishes he’d understood before trusting the “clean” spreadsheet numbers. We also get into the messy parts that make you a real operator: tenant risk, property management, maintenance you can’t ignore, and how capex items like roofs can wreck your expectations if you treat them like ordinary monthly expenses. Grady walks through his first eviction, why Indiana timelines shocked us compared to Chicago, and how he kept going even when early cash flow didn’t show up the way BiggerPockets-style projections promised. Then we zoom out to bigger forces shaping real estate investing in 2025. We debate cash flow versus appreciation and why higher rates push investors to think differently about Chicago fundamentals. We also unpack the Zillow vs Compass private listings fight, why it matters to consumers, and how “gatekeeping” inventory raises real questions about fairness and access. Along the way, Grady explains how AI is changing work, why context and judgment protect your career, and how posting content (even when it’s embarrassing) can open doors. Subscribe for more real-life investing stories, share this with a friend who’s trying to buy their first property, and leave a review with your biggest takeaway. Grady Schmidt Bio: Grady is a real estate investor and full-time finance professional at Google in Chicago. After starting with a condo-hack in downtown Chicago, he’s since moved on to purchasing multifamily buildings in northern Indiana. He enjoys combining his professional experience with AI and his real estate background to build new tools for investors. Grady recently started dabbling as a (very) amateur content creator, sharing his thoughts on real estate, career development, AI, and Cincinnati Reds baseball at @gradybuysproperty on Instagram.

    77. Buying Site Unseen, Creating Content, and Arguing Zillow Vs Compass With Grady Schmidt

  5. Jul 7 ·  Video

    76. How House Hacking And Partnerships Built A Chicago Portfolio With Hart Turner

    Send us Fan Mail Hart Turner joins us to tell the full story: 15 years as an actor in LA, a hard reset on money and career, and then an 18-month sprint that turns into three Chicago multifamily properties. Along the way, we connect the dots between endurance mindset (yes, he finished the Hawaii Ironman) and the day-to-day reality of underwriting, leasing, and staying calm when the deal goes sideways.  We get specific about Chicago house hacking with 5% down, why BiggerPockets can be the gateway but local meetups create real acceleration, and what it looks like to buy in Humboldt Park when inventory is tight and interest rates are unforgiving. Hart walks through his first REO purchase and a five-month closing delay, the DSCR-funded second deal with a partner, and the midterm rental experiment that turned into an expensive lesson about seasonality and unit mix.  Then comes the curveball every investor fears: a lender decides a key partner can’t qualify after you’re already under contract. We unpack how Hart pivots to a new partner, improves the financing, and still closes on a four-unit graystone after negotiating a rare $50,000 credit in a multiple-offer situation. If you’re trying to start late, scale with partnerships, or simply avoid rookie mistakes in multifamily investing, this one is packed with real numbers and real decisions.  Hart Turner Bio:  After beginning his real estate investing journey in 2024, Hart quickly focused on small multifamily acquisitions and house hacking. In just 18 months, he has built a portfolio of three multifamily properties (all Greystones!) totaling nine units, and all located in the Humboldt Park neighborhood. He currently lives in and manages a four-unit property that serves as his second house hack. In addition to his direct ownership portfolio, Hart invests passively in larger Chicago-based apartment syndications through his self-directed IRA, giving him experience with both active and passive real estate investing. Outside of investing, Hart works as an apartment locator specializing in downtown Chicago high-rises and luxury apartment communities, helping renters navigate the city’s most competitive rental markets. When he’s not working on deals or helping clients find their next home, you can usually find him on a pickleball court working on his game. Find Hart on Instagram: @hartturner and TikTok: @hartturner

    76. How House Hacking And Partnerships Built A Chicago Portfolio With Hart Turner

  6. Jun 11 ·  Video

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

    Send us Fan Mail After 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!

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

  7. Mar 25

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

    Send us Fan Mail 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.

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

  8. 09/23/2025

    73. The Unforgettable Impact of Charlie Kirk

    Send us Fan Mail 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.

    73. The Unforgettable Impact of Charlie Kirk
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3.9
out of 5
11 Ratings

About

“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. 

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