EPISODE · Jun 30, 2026 · 23 MIN
How To Find Off Market Real Estate Deals And Fund Them Smart | Dylan Koch | Part 4
from Chief Milestones · host Reshma Vadlamudi
This episode isn't about finding the perfect deal. It's about knowing which assets you're building for income - and which ones you're holding for life.In Part 4 of this conversation, Dylan Koch - wholesaler, buy-and-hold investor, and licensed agent operating across four counties in the Cincinnati market - breaks down the frameworks he uses to separate active income assets from legacy assets, how he thinks about underwriting in a market that punishes both optimism and excessive conservatism, and what he'd actually do if he were starting over with $15,000 today.This was not a theoretical conversation. It was an operational one.We cover:Why cash flow is a defensive metric - useful for covering capex and repairs, not for building wealthThe full structure of Dylan's $1.5M, 12-unit seller finance deal: $1.4M carried at 3% on a 30-year note with a 10-year balloon - and the promissory note clause that made the seller say yesWhat $15K actually buys you as a starting investor - and why the website and business cards come lastHow to use permit data, population trends, and employment growth to find neighborhoods before they moveWhy the single biggest driver of neighborhood decline and recovery is jobs - not crime stats, not aestheticsHow Dylan's entire operator network - CPA, property manager, GC contacts, private money - was built through in-person networking, not social mediaWhy staying top of mind with sellers means sending rehab photo updates to a neighbor who might sell in two yearsIf you're an investor, founder, or operator trying to build something that lasts past the next rate cycle - this conversation is worth your time.This isn't a highlight reel.It's a practical breakdown of how a real operator structures assets, reads markets, and builds relationships - under pressure, not in hindsight.Reach out: [email protected] Milestones is a video podcast featuring honest conversations with founders, parents, and investors about building real businesses, staying healthy, and raising families.New episodes release Tuesdays and Fridays.Youtube: https://www.youtube.com/@ChiefMilestonesInstagram: https://www.instagram.com/chiefmilestones/Spotify: https://open.spotify.com/show/7HLDAe7SP3GnJSTOgAQqLy?si=6e9ac82be46f413cApple Podcasts: https://podcasts.apple.com/us/podcast/chief-milestones/id1861185226
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This episode isn't about finding the perfect deal. It's about knowing which assets you're building for income - and which ones you're holding for life. In Part 4 of this conversation, Dylan Koch - wholesaler, buy-and-hold investor, and licensed agent operating across four counties in the Cincinnati market - breaks down the frameworks he uses to separate active income assets from legacy assets, how he thinks about underwriting in a market that punishes both optimism and excessive conserv...
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How To Find Off Market Real Estate Deals And Fund Them Smart | Dylan Koch | Part 4
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