Podcast

By Mark Ainley

Episode 52: Saving Thousands of Dollars With the Appropriate Tax Strategy and Deductions

It’s March and taxes are top of mind! However, by only reactively focusing on taxes during this one part of the year, you are potentially leaving money on the table. Aaron Zimmerman, a Chicago investor and CPA, provides great insights into how to best work with a CPA, the i...

By Mark Ainley

Episode 51: Becoming "Brick Rich" on the Northside; Owning 74 Doors by Age 29

Would you trade salary for knowledge? John Westbrook spent time straight out of college working for one of Chicago’s largest property managers to build-up his foundational knowledge of the industry. John has since transformed this knowledge into a substantial portfolio of m...

By Mark Ainley

Episode 50: Building a Chicago Empire with Andrew Holmes

For our 50th episode we thought we’d give everyone a special treat... Andrew Holmes is one of the most well-known names in Chicago Real Estate Investing. Andrew explains his incredible journey, from his early days as a hustling agent, to how he structured his first few inve...

By Mark Ainley

Episode 49: Moving Fast and Weathering Storms with Investor and Clickinvest Co-Founder Rosario Terra...

For the past 15+ years, Rosario Terracciano has been cutting his teeth with a lot of hard learned lessons. In today’s episode, he shares some early mistakes he made about buying, working with contractors, estimating ARVs and leasing. He shares how he weathered the sub-prime...

By Mark Ainley

Episode 48: The Doctor of Motor Row - David Shifrin

For everyone working a W2 job, our guest today, David Shifrin, is a great example of how to incorporate real estate into your long-term plan without having to give up your current career. David Shifrin wanted a way to marry his professional career as a plastic surgeon to his...

By Mark Ainley

Episode 47: Building Generational Wealth Through 1031 Exchanges with Lauren Speidel

The term “1031 Exchange” is ubiquitous, but do you really know what it is or how to even engage in one? Lauren Speidel of Exeter1031 is a subject matter expert and breaks it down for you today. She’ll explain the different parties involved, what the criteria are...

By Mark Ainley

Episode 46: Why Invest in Smaller Multifamily Properties in the North and Northwest Suburbs of Cook ...

Chicagoland is an enormous market with a ton of sub markets. Anthony Citriglia of Essex Realty’s submarket covers many of the near north and near northwest suburbs and he breaks down exactly what those markets are like; how they differ from Chicago; and how they differ from...

By Mark Ainley

Episode 45: Community Investment Corporation (CIC) - Chicago’s Non for Profit Lender, with Jack Cr...

For over 35 years, Jack Crane has been providing expertise on financing the acquisition and rehabilitation of commercial real estate. The majority of those years have been spent as Sr. VP of lending at CIC where he is responsible for carrying out the mission to be a leading ...

By Mark Ainley

Episode 44: Understanding The Intricacies of Various Mortgage Products With Chris Puleo

How many ways are there to finance buying a property? Way more than I’m aware of which is why our guest Chris Puleo is here. With his robust 20+ year career, Chris has seen it all and explains a plethora of different popular products. With so much interest in househacking, ...

By Mark Ainley

Episode 43: Househacking, Scaling, and Large Multifamily Deals With one of Chicago’s Best Power Co...

Have you ever looked at your significant other and wanted to build an empire with them? That’s exactly what Nicky and RJ De Leon have been doing since the early days of their relationship. Today, they tell their story from start to current day, diving into how they had all ...