Jason Wagner is the Owner and Managing Broker of Greystone Realty in Chicago, where he leads a high-performing team of agents who are all active real estate investors. He is the author of The Wagner Report, an exclusive, data-driven market analysis that empowers homeowners, investors, and real estate professionals with specific neighborhood insights. His team at Greystone Realty has earned multiple Top Producer awards from the Chicago Association of Realtors, with over $100 million in total sales.
An active investor himself, Jason owns and self-manages 22 rental units on Chicago’s Northwest Side, where he has developed deep expertise in portfolio growth through partnerships and innovative low-down-payment strategies. As a former licensed general contractor, he has hands-on experience managing gut rehabs and new construction projects.
Jason began his real estate career after departing a corporate finance role at Allstate Insurance in 2016. He holds dual bachelor’s degrees in Finance and Accounting from Augustana College, giving him a strong analytical edge in spotting market trends.
Jason also co-hosts the Real Life Investing Podcast with his wife, Rachel, where they offer actionable insights on wealth-building, business, and family life. He lives in Arlington Heights with Rachel and their three children.
Fun fact: Inspired by Can’t Hurt Me by David Goggins, Jason once completed 2,380 pull-ups in 8 hours straight — a reflection of his grit and discipline.
Mantra: “If my client didn’t learn something from every meeting with me, I didn’t do my job.”
Ricel is the virtual administrative assistant who works directly to support the back office and all of the Greystone Realty brokers. She is a very detailed and passionate professional with a strong work ethic and provides Greystone Realty and all of it’s clients with tremendous value. Ricel is married and has two children, she currently lives in Cainta, Philippines.
Brian DeSimone joins Greystone Realty with the experience of owning and operating a creative small business with his fiancé, Ashley. Over the past ten years, through their company, they have traveled and hiked all over the world, capturing videos and photos of people, places, businesses, and once-in-a-lifetime events. That work is how Brian landed in real estate: he has designed, photographed, and filmed properties and agents in the industry for over seven years.
Brian’s approach is simple: lead with knowledge, humility, and kindness. Being in multiple industries, he believes in the power of work ethic combined with preparation, values integrity and treating people with respect and compassion, and trusts the solutions that creativity and open-mindedness yields. He brings the discipline of a former college athlete, the client-oriented perspective crucial to owning a small business, and the curiosity of a professional creative to be the best agent he can be.
With a real estate investor approach, Brian believes that substance, not flash, is the core of a successful client experience in the Real Estate industry.
Listen to Brian’s episode on the Real Life Investing Podcast here: https://open.spotify.com/episode/6StMU2XM4wdaj1zSEiNQfO?si=SmnnEnVPSUSRH5FuvMfxBQ
Andrew Stack has been involved with real estate in various capacities since 2008 including residential leasing, management, general contracting, and as a mortgage loan officer. Andrew comes from a consultative sales background, having been with BMW for 7 years where he learned truly listening and understanding the needs of his clients takes precedence. He decided to leave auto sales to pursue his passion for real estate. After trying out many different facets of the real estate world, it was time to go all in and make the jump as a full time broker. Bringing a wide breadth of experience to the role helps connect to his clients and see things in a different light, while focusing on providing the best possible service, professionalism, and attentiveness to detail. Andrew graduated Augustana College with a Bachelor’s degree in Business Administration with minors in Management, Marketing, and MIS. His goal is to bring an investment mindset to his clientele and address issues from unique angles to help provide value and aid in decision making. When he’s not helping clients buy or sell, he’s with his wife exploring the world, scuba diving, or snowboarding in Colorado where they lived for three years.
Former World Class Para-Triathlete, turned Fitness Coach, turned Software Engineer. While his career path may fluctuate, the long term target does not. That long term target being: “Building a portfolio of investment, cash flowing properties, in order to pursue career goals because he wants to, not because he has to.” As Levi continues to grow his own portfolio, he enjoys helping people either continue to build their own, or educate people on how to start their own! Interested in turning a 10-13%+ cap rate on Multi-Unit buildings on the North side of Chicago? Levi Kane is your guy.
Listen to Levi’s episode on the Real Life Investing Podcast here: https://open.spotify.com/episode/31lq0Qt1xYW47h9tYHsnGC?si=7quMKRGBToWq8d5MK2uKww
Jennie is the Co-Founder of Property People along with her partner Gregory Kyler. Licensed General Contractors, the house flipping duo specialize in residential redevelopment and new construction. Jennie is a wanna-be-designer with a deep passion for people, traveling, sand volleyball, yoga, and creating new plant based dishes. She grew up in Hoboken New Jersey and has the bestest 13-year old Westie named Chief.
Bringing her hospitality and management consulting experience to the negotiation table, Dannielle is a lover of all things family, Jamaican patties, and Michael Jackson. Understanding the difficulties in relocating to a new home, Dannielle approaches each interaction as an opportunity to educate and empower her clients. In pursuit of building financial freedom for herself and her family, Dannielle seeks to build a portfolio of multifamily and short-term rentals in Illinois and Florida.
Kyle got started in real estate, assisting in the management and maintenance of family rental properties. Since then, he has invested in flipping houses while simultaneously working as a Physical Education Teacher. His goal is to grow a portfolio of cash flowing rental properties and assist others to do the same. Kyle’s strong communication, organization and teaching skills gained from working in education for the past 10 years will translate to helping clients fully understand their situation from all angles and assist them in making asset based decisions.
With a passion for real estate, Stephen has established himself as a licensed realtor and home inspector, assisting clients in finding their dream homes and ensuring their investments are sound.
Bringing a wealth of knowledge to the table, Stephen also possesses valuable experience in home renovations, enabling him to envision the true potential of properties and guide clients in making informed decisions. Additionally, his expertise as a landlord equips him with a unique understanding of the market and the needs of both buyers and sellers.
Driven by a genuine desire to help others, Stephen goes above and beyond to provide exceptional service, putting his clients’ best interests first. With his friendly demeanor, professionalism, and attention to detail, he creates a seamless and rewarding real estate experience for every individual he serves.
Outside of work, Stephen enjoys spending quality time with his family, exploring the great outdoors, and embracing new bbq adventures. He strives to make a positive impact on the lives of others through his expertise and genuine care.
Kyle is a wedding photographer known for capturing honest, unscripted moments—and he brings that same calm presence and attention to detail into his work as a real estate agent. With a background rooted in storytelling and client care, Kyle is committed to guiding buyers and sellers through each step with clarity, empathy, and intention. His goal is to build a real estate portfolio for his family long term as well as serving his clients the way he serves them on their wedding day.