Advertise on podcast: Real Life Investing With Jason & Rachel Wagner

Send us Fan Mail What does it actually take to walk away from a six-figure W-2 and bet on real estate full-time? We talk with Arthur Barkan, a former pharma professional with a chemistry background who turns hustle, relationships, and a repeatable value-add process into rapid multifamily growth and a portfolio that’s pushing toward 80 units. Along the way, we unpack how a simple personal brand can make you memorable and why being “reachable” matters as much as being credible.  We get tactical on the investing side: buying 2- to 6-unit properties, underwriting with quick rules of thumb, and creating forced appreciation through light renovations and rent increases. Arthur also shares operator-level details that don’t show up in most highlight reels, like charging back water costs to change tenant behavior, using property management software to streamline rent collection, and hiring the right ops and maintenance help once the unit count starts to stretch your time.  Arthur then compares his first hand eviction experiences with Lake County versus Cook County timelines, explains how process service and documentation work in practice, and breaks down when “cash for keys” can be the cheapest, fastest business decision. We also touch on refinancing, lender expectations, cost segregation for tax strategy, and the constant tension between building cash flow now versus maximizing long-term net worth.  If you’re serious about multifamily real estate investing, value-add apartments, and the BRRRR mindset, listen through and take notes. Subscribe, share this with an investor friend, and leave us a review with the biggest move you want to make next. Instagram: @arthur_barkan 224-433-4553

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

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.

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

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.

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

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!

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.

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.

Send us Fan Mail 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.

Send us Fan Mail In 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

Send us Fan Mail When 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 HACKING VA 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.pdf House 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-exemption Returning Veterans Exemption (recently returned from active duty): 🔗 https://www.cookcountyassessor.com/returning-veterans-exemption Disabled Veterans Homestead Exemption Details (State of IL): 🔗 https://www2.illinois.gov/veterans/services/Pages/property-tax-relief.aspx Shoot Dubois a message on FB if you want to ask questions or get in contact! https://www.facebook.com/share/16CfS5xbFf/?mibextid=qi2Omg For additional resources, click here.

Send us Fan Mail We 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 children We 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.

Send us Fan Mail In 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: [email protected]  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.

Send us Fan Mail What 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.