Boring Land Deals Are Winning (Podcast Ep#171)

After being involved in nearly 1,000 land deals, Drew Haney has enough data to start seeing some pretty clear patterns.In this episode, Jessey and Kevin sit down with Drew to talk through what the numbers are actually showing inside Rooster Capital, including which deals have produced the strongest returns, which ones tend to sit the longest, and why chasing bigger spreads is not always the better move.Drew shares why the sweet spot in their data has been smaller rural and recreational properties, why six-figure infill lots have been much harder to move, and how hold time can matter just as much as the profit on paper.They also get into seasonality, why August and September have historically been tougher months to buy, the danger of drawing conclusions from tiny marketing samples, and why operators should think beyond spreadsheets when evaluating risk, capital, and opportunity.What you’ll learn on this episode:• What nearly 1,000 land deals reveal about the best-performing buy box• Why bigger deals can create more risk, longer hold times, and more mental overhead• What Drew’s data shows about seasonality and when deals tend to perform best• Why small sample sizes can lead investors to make the wrong marketing decisions Chapters00:00 Intro02:59 Drew’s path from land flipping to Rooster Capital05:17 What the data actually says after nearly 1,000 deals07:23 Why six-figure infill lots have struggled08:04 The buy box producing the best returns13:10 Why bigger deals are not always better19:14 Risk, hold time, and mental bandwidth22:49 What the data says about seasonality25:16 Why small marketing samples can mislead you28:38 What Drew looks for in funding partners30:02 Looking beyond the spreadsheet31:48 The reality of losses across nearly 1,000 dealsConnect with Drew Haney:Rooster Capital: https://roostercapital.landEmail: [email protected] to learn more about Pebble and what we’re seeing across land investor direct mail? Hop on a call with us at www.pebblerei.com/demo