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Chicago Real Estate Investing News

One Land Flip Changed Everything: Greg Dickerson’s Journey From Handyman to Real Estate Developer

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Greg Dickerson shares his 30-year journey in real estate, from handyman to successful developer and mentor. He discusses opportunities in the market, the importance of…

How Michael Most Grew From 3 to Nearly 30 Loan Officers in 18 Months

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Michael Most shares his 26-year journey in the mortgage industry, his approach to building a nationwide team, and how he leverages AI to enhance recruiting…

Flip or Rent? How New Real Estate Investors Should Choose

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Gus Gallucci shares his extensive experience in residential real estate, flipping, and midterm rentals. He discusses acquisition strategies, staging tips, and how to navigate local…

How to Build Wealth With a Mortgage | Real Estate Leverage, HELOCs & Home Equity

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Sean Herrero, a mortgage advisor, shares insights on home buying, mortgage strategies, and navigating California's real estate market. Discover how to build wealth through real…

Airbnb Arbitrage Without Buying Property: How Andrew Donham Scales Luxury Short-Term Rentals

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Andrew Donham shares his innovative approach to Airbnb arbitrage, scaling across multiple markets, and strategies for building a profitable short-term rental business in a challenging…

Construction Risk Management: Protect Your Real Estate Profits

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Randal Funchess hares his unique approach to integrating risk management, international real estate, and family life to build a diversified and resilient investment portfolio. Discover…

Why the Cheapest Real Estate Loan Can Cost You More | Shaun Ashkenazy on Private Lending

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Shaun Ashkenazy, founder of Lendyx and Onyx Funding, shares insights on private lending, deal structuring, and market opportunities. Discover how his boutique approach combines personalized…

Shipping Container Homes: How One Builder Cuts Build Time by 30%

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Daniel Wagler shares his journey from luxury home building to innovative Core 10 steel container homes, highlighting the benefits, challenges, and future opportunities in modular…

How This Real Estate Agent Made $52K on His First House Flip

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Gerardo Hernandez shares his journey from real estate agent to successful property flipper and coach, highlighting strategies for scaling, managing teams, and navigating market shifts.

How Real Estate Investors Can Use Tax Incentives & Community Funding | Devon Fraser

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Devon shares his 27-year journey in the title industry and his expertise in CRA funding, opportunity zones, and community redevelopment. He emphasizes education, relationship-building, persistence,…

Real Estate Tokenization Explained: How Blockchain Is Changing Property Investing

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Dan Thompson shares his extensive experience in real estate, tokenization, and innovative investment strategies, offering valuable insights for investors and entrepreneurs alike.

Multifamily Investing in 2026: Distressed Deals, Refinancing & Buying Opportunitie

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Jeremy and Reine from Ironhold discuss their vertically integrated real estate business, which includes asset management, development, a multifamily fund, and a nonprofit arm. They…

How Canadian Real Estate Investors Should Structure Mortgages,HELOCs & Cash Flow

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Rakhee Dhingra, CEO and broker of record of Mortgage Savvy, shares insights on Canadian real estate investing, mortgage strategies, and how to build wealth through…

Starting a Real Estate Business? Build These 3 Systems First

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Ebony Vick shares her journey into real estate, from being unexpectedly forced to move while in real estate school to purchasing her first home. She…

How to Build a Real Estate Buyers List Before You Find Deals | Bryson Rose

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Bryson Rose shares his journey from working in various jobs to becoming a successful real estate investor and connector. He discusses his strategies for land…

Is the Multifamily Market Bottom In? Southern California Apartment Investing Outlook for 2026

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Dean Zander, a seasoned multifamily broker in Southern California, shares insights on current market trends, investment strategies, and the impact of market conditions on multifamily…

Real Estate Marketing Strategy: Build Client Relationships & Close More Deals

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Andrew Saksa, VP of Strategic Channels at Essential Engine, shares how branded magazines help real estate professionals, financial advisors, investors, and small business owners strengthen…

Why Luxury Real Estate Development Can Create Bigger Profits at Similar Volume | Maximilian Vollmer

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Max shares his inspiring journey from starting with just seventy-six dollars to building a multi-million dollar real estate development business in Florida. He discusses market…

How BINS APP Is Disrupting Construction Logistics | John Zaloum

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John Zaloum shares his journey from real estate investing to building innovative tech solutions for construction site management. Discover how his hands-on industry experience fuels…

Credit Scores Aren’t Enough: How Landlords Should Really Screen Tenants

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Michelle Martinez shares insights into her tenant and employment screening business, discussing how technology, market shifts, and strategic growth shape her company's success. Discover practical…
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