Real Life Investing With Jason & Rachel Wagner

Real Life Investing With Jason & Rachel Wagner

“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.

Episodes

July 14, 2025 73 mins

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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. &quo...

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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 ant...

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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 b...
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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 l...

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In 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 glob...

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RFK Jr.'s appointment as HHS Secretary could signify a shift toward greater transparency and parental choices in public health and vaccination policies. Jason and Rachel Wagner discuss their own experiences with vaccination and the importance of informed consent, raising significant questions about the current understanding of vaccine safety and industry accountability.

• RFK Jr. confirmed as HHS Secreta...

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February 7, 2025 129 mins

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Bible sales are reaching record highs, and across America, more people are reconnecting with their faith. This makes today’s episode especially timely as we sit down with the incredible Anita Pilalis, a devoted and passionate Christian. Anita shares the powerful moment she found God and how it became her life’s mission to serve Him. 

Our conversation touches on how others can lean into their faith to help them during t...

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Today's episode, we discuss the arbitration case over earned real estate commissions we recently found ourselves in.  In a claim that was brought against brokerage, we walk through how we effectively defended our commission and ultimately prevailed as the unlikely victors.

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Join us for one of the most inspirational conversations you can hear as we sit down with Mike Bednarz.  It was just another day quoting a job for his commercial HVAC company, Bedco Mechanical, when Mike suddenly lost control of a ladder and fell 25 feet onto concrete.  Mike suffered a severe brain injury and shattered many bones from that accident.  He shares his story of how he had always lived a life of discipline, ...

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Today's episode dives into our spiritual journey back to faith.  Our conversation explores that impact of the 2024 presidential election and how it offered the evidence Jason needed to rediscover his abandoned faith. 

We hope that our story offers others an opportunity to become curious about God and encourages you to go explore. 

A truly relatable episode. 

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Tune into our take on how Donald Trump and the Republicans won the 2024 election in a landslide.

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November 5, 2024 39 mins

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We voted. For Donald Trump.  Here's why.

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Join us on the Real Life Investing Podcast for a thought provoking conversation of shifting political landscapes with our  guest, Adriana. As a Hispanic raised in a middle-class neighborhood with strong Democratic values, Adriana shares her compelling journey from a lifelong Democrat to a passionate supporter of Donald Trump and the Republican Party. This transformation highlights the power of personal experience in r...

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Jason and Rachel detail how they went from being worth more dead than alive, to surpassing $1M net worth in 5 years through real estate investing. 

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We bought a Cybertruck. We rent it out on Turo. Here’s how it’s going and here’s the story of why we decided it was a worthwhile investment. 

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Meet Leslie Collazo, a passionate advocate and dedicated community leader from the heart of Chicago. Born and raised in Illinois, Leslie is a proud daughter of Puerto Rican heritage, bringing a rich cultural perspective and a commitment to serving her community. As she embarks on her journey to become the State Representative for the 8th District, Leslie's bilingual abilities amplify her connection with diverse c...

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What if the political leanings of your college professors are shaping your worldview more than you realize? 

Today we discuss the chart Elon Musk shared that shows the dominance left leaning professors have within our colleges and universities. This chart is also supported with a 2016 study of Liberal Professors Outnumber Conservatives 12:1. 

Our discussion details personal reflections of our college...

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Catch our take on the Kamala Harris vs Fox News interview and what it says about the state of the media.  Going further, we discuss the important voting topics that the left and right are debating, while also diving into Trump Derangement Syndrome (TDS).  Rachel gives us her opinion on Trump's treatment of women, and finally we talk about the key pieces that will win the election.

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Can one thrive as a conservative in a sea of liberal ideology? Embark on a journey with us, Rachel and Jason Wagner, as we unravel our personal narratives of embracing conservative beliefs while living in the predominantly Democratic state of Illinois. We'll peel back the layers of our political evolution, shaped by our unique backgrounds—Rachel's intriguing childhood conversations with her grandfather, a De...

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Join us as we celebrate our 50th episode on the Real Life Investing Podcast. We couldn’t have reached this milestone without our listeners, our virtual assistant Ricel, and the incredible guests who shared their wisdom and experiences. This episode is a heartfelt reflection on our journey, highlighting the transformative impact of the 75 Hard program, with inspiring stories from Nicky De Leon (Ep #8), Jon and Keira Qu...

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