This episode features a solo session with John Casmon, where he draws on personal investing experience in markets like Chicago, Cincinnati, Louisville, and San Antonio to share a deep-dive framework for evaluating which markets to invest in, and how to spot the signs of long-term growth. From understanding economic indicators and infrastructure to aligning your personal investing style with neighborhood dynamics, this episode is packed with strategic guidance on identifying the right market — and the right moment — to make your move.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

Key Takeaways

• Start by investing in your own backyard, local familiarity and access outweigh national trends early on.

• Use "path of progress" logic to spot adjacent neighborhoods with similar fundamentals but lower prices.

• Look for population growth, industry diversification, infrastructure investment, and pro-development policies.

• Understand your own investing goals to determine what kind of markets and submarkets align with your criteria.

• Ride the coattails of developers and large employers, when they commit to a market, opportunity follows.

Topics

Why Market Selection Matters

• Why investing close to home gives you an advantage

• How John evaluated neighborhoods like North Center, Avondale, and Hermosa in Chicago

Expanding Beyond Your City

• Lessons from shifting to Cincinnati and using family ties to anchor new market exploration

• The importance of clarity on investor criteria before analyzing new areas

What Makes a Market Attractive

• Key indicators: population growth, job diversity, geographic accessibility

• Red flags: rent control, oversupply, misaligned development

Case Studies: Cincinnati, Louisville, San Antonio

• The impact of infrastructure and corridor development in Cincinnati

• How recession-resistant industries shaped John's decision to invest in Louisville

• Why San Antonio's "quiet strength" made it a strategic move

Using Public Data to Guide You

• Sites John uses: census.gov, bls.gov, datausa.io

• How to track local chambers of commerce, development plans, and funding incentives

What to Avoid or Watch Closely

• Risks of relying on government subsidies or unstable funding

• Importance of local political climate and long-term planning by municipalities

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Next Steps

• Research your backyard market before expanding elsewhere

• Align your criteria (cash flow vs. appreciation, investor type) before evaluating a market

• Track macro indicators (population, jobs) and micro conditions (local policy, neighborhood dynamics)

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