20. Unconventional First Time Buyers: A House Hacking Partnership With Brian and Ashley DeSimone

08/30/23 • 80 min

Real Life Investing With Jason & Rachel Wagner

Venturing away from their wedding photography business, Brian and Ashley reveal the steps, strategies, and occasional stumbling blocks they've faced in purchasing and rehabbing their first house hack investment property in Chicago. These two candidly share how they went from a thriving small business to a complete halt in income from the pandemic, as they turned to real estate to help provide them with stability. Their story is a perfect example of resilience and creativity, which is extremely admirable.
Brian and Ashley's journey is not just about real estate investing - it's also about intentional living and entrepreneurship. They share their financial freedom goals and future plans, including Ashley's transition to part-time photography/videography, and Brian becoming a full-time real estate agent with Greystone Realty. They emphasize the importance of trust, integrity, and maintaining a clear vision in maneuvering in a new industry. With a blend of friendship, business acumen, and a dash of risk-taking, Brian and Ashley's story serves as an inspiring roadmap to achieving your own entrepreneurial dreams.

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19. Gen Z Insights: Navigating High School, Politics, and The Pandemic

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High school TODAY is different than when the millennial generation was there. Joining us on the show is Rachel's sister, Maddy, who brings us up to speed on what it is like to be in school as a Gen Z entering Senior year.
Maddy was diagnosed with Celiac disease at a young age and she explains what it is like being on a strict diet most of her life. She also details her experience of attending school during the pandemic and how the effects are still being felt.
The conversation leads into how political arguments among her peers have become more prevalent, as Maddy describes the divide that has developed at this young age. We discuss her sense of the social pressures that have emerged relating to privilege, gender identities, and how teens are communicating online.
This episode is a transparent dialogue of what it is like to be a high schooler today and is promised to bring you a deeper understanding of the realities that teens are facing. By the end of the show, you'll walk away with confidence and inspiration from Maddy as she explains how she is defying her doctor's expectations to continue to pursue her passions and dreams.
Join us for our most emotional and unreserved conversation to date.

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21. Live In Renovation: Jordan Warner's Journey Into Chicago Real Estate

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Ever wondered about the thrill and challenges that come with investing in real estate through a live in renovation? This episode brings you a riveting conversation with Greystone Realty agent Jordan Warner, a man who turned a fixer-upper ranch in West Humboldt Park into an engaging journey of discovery.
This episode offers more than just a walkthrough of a renovation project. Jordan takes us into the heart of his real estate journey, shedding light on the sacrifices made and the lessons learned in the process. We delve into the significance of documenting the journey, setting tangible goals, and understanding what it takes to achieve those goals. Jordan's experiences and reflections are a valuable guide for anyone keen on navigating the real estate waters.
As we drift from Chicago to Texas, Jordan shares his unique experience of using Airbnb's in various neighborhoods, maintaining a swimming pool under the relentless Texas sun, and finally taking the plunge into full-time real estate investment. He provides an insightful look into the dynamics of the Fort Worth real estate market, the practice of renting out rooms, and his eventual return to Chicago.
The episode concludes with Jordan's thoughtful stance on gentrification, the industry's oversight in adjusting rents over time, and his ultimate aspiration of being a responsible housing provider. This episode offers a wealth of knowledge for anyone interested in real estate investing, property renovation, or simply seeking inspiration in their entrepreneurial voyage.

Real Life Investing With Jason & Rachel Wagner - 20. Unconventional First Time Buyers: A House Hacking Partnership With Brian and Ashley DeSimone

Transcript

Speaker 100:00:29.781

Welcome to the Real Life Investing Podcast with Jason and Rachel Wagner . We are husband and wife and dedicated to bring you conversations that revolve around real estate , entrepreneurship , personal development , relationships , politics and just regular conversations that come across the dinner table . We will share with you actual stories of relatable people with hopes to inspire you t