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We break down why Chicago’s housing is so expensive. Despite record taxes, the city is at an all-time high in debt. What would it take to attract capital, build more homes, and lower prices? We share data on schools, zoning, conversions, and policy incentives that could restart growth.

• highest taxes paired with large deficits and lender uncertainty
• CTU costs and poor literacy and math outcomes are driving distrust
• capital flight, bank redlining, and private equity debt costs
• stalled office-to-residential conversions and rigid mandates
• aldermanic control and downzoning that choke density and raise prices
• case study on 4330 N California and infeasible set-asides
• renters versus owners, community stability, and wealth
• Northwest Ordinance fees lower legacy owners’ equity
• a practical plan to incentivize office return and revive transit, retail
• three levers for a city: taxes, cuts, or growth, and why growth wins

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We tour Michael Jordan’s mansion, unpack why mega-mergers won’t fix real estate, and map the content-first play agents can actually control. Then we get tactical on assistants, TCs, first-time buyer math, and the real way to refi without resetting the clock against yourself.

• Jordan’s house as a case study in brand, nostalgia, and usability
• Compass/Anywhere stakes vs ownership, licenses, and antitrust exposure
• Listings as content and the shift to walled marketplaces
• Personal branding over brokerage identity for long-term leverage
• Listing-heavy strategy, new agent hurdles, and ethical content borrowing
• Consistency, planning, and buying back time with TCs and assistants
• Team coverage, scaling without burnout, and better client speed
• Travel, family seasons, and how life cadence shapes business
• 2026 outlook on rates, inventory, and suburban vs urban demand
• High-rise headwinds, HOA math, and first-time buyer scenarios
• Refinance realities: principal vs payment, when it truly makes sense

You definitely could subscribe on any of the platforms that you have on your phone, or always you can watch on YouTube

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Navigating the competitive housing market requires strategic mortgage preparation and understanding winning tactics to secure your dream home.

• Going through underwriting before making offers gives you a crucial competitive advantage
• Waiving mortgage contingency is often necessary to compete with cash offers
• Strong buyer consultations upfront prepare clients for the competitive market reality
• Showing higher down payments on offers (even if you later reduce it) strengthens your position
• Local lenders who call listing agents personally give buyers a significant edge over big banks
• Multiple offer situations require speed and decisiveness, not waiting for open houses
• Property values in the Midwest are rising four times the national average
• Waiting for interest rates to drop is often a losing strategy as home prices continue to rise
• Time-limited offers can help avoid bidding wars by forcing sellers to decide before open houses
• Having well-defined non-negotiables helps agents and lenders maintain their reputation

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Chicago families are challenging the conventional wisdom that having children means moving to the suburbs, finding that city neighborhoods offer unique advantages for family life and child development.

• City children develop greater independence, street smarts, and social skills compared to their suburban counterparts
• Neighborhood parks function as community hubs, creating interconnected social networks across different areas of the city
• Chicago has more green space than any other American city, providing ample outdoor opportunities
• Multiple school options exist within city limits, both public and private
• The real estate market currently has approximately three offers per single-family home
• What matters most in winning offers isn't simply price but offering a seamless, stress-free transaction
• When shopping for a home, prioritize neighborhood trajectory and location over "shiny" new construction
• A property's future value depends more on its location and neighborhood dynamics than on its current amenities
• Working with experienced agents who understand neighborhood trends provides crucial market insights
• Chicago prices are appreciating at four times the national average due to limited inventory

Don't assume you need to leave the city when you have kids—give city living a chance and you might find you don't want to leave at all.

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Maggie shares her journey from corporate life in marketing to becoming a successful real estate agent, highlighting how relationship-building and immersion in the craft creates sustainable success rather than chasing quick transactions.

• Left corporate job in marketing and graphic design after feeling creatively stifled
• Started at eXp but quickly realized the need for proper mentorship and training
• Learned the business by covering inspections, showings, and open houses for other agents
• Built client base primarily through open houses - doing up to four every weekend
• Finds deeper satisfaction in relationship-based business versus transactional models
• Values boutique brokerage environment where collaboration trumps competition
• Emphasizes the importance of being present at inspections to build knowledge and credibility
• Plans to focus on organization, consistent client outreach, and social media presence
• Believes in investing in learning over chasing higher commission splits as a new agent
• Started with buyers through open houses, now transitioning to more listing business as clients return

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We started running our own numbers on what happens to people after they join Jameson Sotheby's. The average agent achieves more than 100% increase in production during their first year with us—a remarkable statistic that reflects our commitment to providing the right environment, tools, and support for success.

• From carpet cleaning to real estate development—Chris Feurer's entrepreneurial journey led to acquiring Jameson in 2008
• The timing couldn't have been worse—purchasing a brokerage right before the Lehman Brothers collapse required daily survival mode
• Taking the Sotheby's International Realty brand in 2011 marked a turning point that opened doors to luxury opportunities
• COVID-19 became a catalyst for reimagining the entire business model with a focus on what agents truly need
• The shift to fewer, larger office "hubs" with emphasis on hospitality, marketing, and concierge services
• Creating a culture of collaboration and relationships through meaningful events and gatherings
• Building a direct-to-consumer presence through social media has become essential as the industry evolves
• Chicago remains undervalued compared to other major cities despite leading the nation in price appreciation
• Low inventory (1.3 months of supply) and limited new construction are driving significant market pressure
• Maintaining fiduciary responsibility in an era of industry upheaval remains their guiding principle

We believed that if we maintain our values and fiduciary responsibility at the highest level, no matter what happens in the industry, we'll continue to thrive. That's what drives us forward.

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Tony Angelos shares his journey from finance to real estate during the pandemic, detailing how he leveraged social media to build a thriving business despite challenging circumstances. We explore how accountability is the foundation for success in self-directed companies like real estate.

• Accountability is the #1 factor in determining success—taking responsibility for both wins and failures
• Hyperlocal focus can dramatically increase business success, as demonstrated by Jason quadrupling his business after focusing on just four neighborhoods
• Social media has become an essential lead generation tool, with Tony looking to generate over $250,000 in 2025
• Print marketing is still effective when used strategically and consistently
• Understanding a client's timeline and motivation is crucial to providing value and closing deals
• School districts significantly impact property values, making knowledge of local education options a valuable asset
• Consistency in executing 5 key money-making activities is more important than constantly seeking new strategies
• Authenticity in social media presence ensures clients know exactly who they're working with before the first meeting

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A journey through personal grief shapes our lens in real estate, reminding us of the impact life has on our work. We discuss the nuances of today’s seller's market, the emotional connection to clients, and the essential lessons derived from loss.

• Exploring how grief informs personal and professional growth
• The influence of a seller's market on buyer strategies
• Crucial mindset shifts & the "five P's"
• Impactful reflections on loss and its effect on relationships
• Emphasizing the importance of compassion in client interactions
• Navigating market demands through educated strategies
• The necessity of prioritizing family time over work obligations
• Real estate strategies addressing the current competitive landscape

Check out our entire episode to gain insights into both navigating the market and life’s challenges with grace!