Drew Haney is back on the show, and this time Jessey and Drew dig into a question every land operator faces: where should the money for your deals come from? Drew went from flipping around 300 deals himself to funding over a thousand, so he has seen what works (and what keeps people up at night) from both sides of the table.

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.

No agenda, three friends, and an honest read on where the land market actually sits right now. Drew, Seth, and Stride CRM co-founder Mike Balcom get into why roughly half the investors who piled in during COVID have already quit, which strategies still produce deals when volume slows, and what separates the operators who survive a downturn from the ones who fold. Drew pulls from the ~850 land deals Rooster Capital has funded to make the case that the boring, smaller flips are the ones quietly producing the strongest returns.

Drew sits down with Abi to walk through the failure mode that wiped out a previous land business — the $40K/month debt service that left no margin when deal flow slowed. The pivot to Rooster Capital's JV-funding model came directly out of that lesson: capital flexes with deal volume instead of crushing the operator when the market turns.

Drew on Ep #156: why the unsexy operational stuff (clean title, fast diligence, tight comms) is the actual moat in land flipping, and why most operators chase the wrong shiny things.

Drew sits down with Seth to demystify land funding — risks, structure, what makes a good operator-funder fit, and why he's seen the JV model outperform hard-money paths for raw land specifically.

Military to millionaire through land flipping — Drew's path from Army veteran to seven-figure land operator and now funder. Mindset, mistakes, and what most veterans get wrong about civilian entrepreneurship.

Drew with Kendall on the land funding vs operating decision tree — when to flip your own deals, when to fund someone else's, and the brutal honest math behind both paths.

Buying land in uncertain markets — how Drew thinks about pricing, holds, and the operator profile that survives a soft market. Practical underwriting in turbulence.

Drew on building the Milk & Honey land investor community — why peer accountability beats coursework, the kind of operators who actually compound, and what he looks for in funding partners.

How Drew built and exited his land operating business, and why he chose to redeploy that energy into funding instead of staying on the operating side. The real economics behind both sides of the transaction.

The entrepreneurial attitude — Drew on how military service shapes the operator mindset, the discipline required to actually finish deals, and what veterans bring to land that civilians often miss.

Unlocking the hidden potential of vacant land — why most real estate investors overlook the asset class, the margin profile, and what to look for in a first deal.

Drew and Jaren on the Land Mavericks playbook — how a peer community of land operators outperforms solo coursework, and what they'd tell their younger selves.

How Drew built a seven-figure land business in 8–10 hours per week, with no automation. Workflow, focus, and the bullshit-free version of how land actually compounds.

Drew's transformation from day trader to seven-figure real estate powerhouse on Brent's flagship show. The wholesaling-to-land pivot, the operator economics, the call discipline that makes deals happen.

Drew's first appearance with Joe — his story from active duty Army into vacant land investing, the early mistakes, and the framework that turned the corner.