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Boring Land Deals Are Winning (Podcast Ep# 171)

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Author

Jessey Kwong

Pebble Co-Founder

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Boring Land Deals Are Winning (Podcast Ep# 171)

Podcast

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


Connect with Drew Haney:
Rooster Capital: https://roostercapital.land
Email: drew@roostercapital.land

See Pebble in action.

Book a 30-minute demo and we'll show you exactly how it works for your team.

The land acquisition CRM built for teams that mail consistently, track performance and close deals. Everything your team needs in one place.

By subscribing you agree to with our Privacy Policy and provide consent to receive updates from our company.

© 2026 Pebble REI Inc. All rights reserved.

See Pebble in action.

Book a 30-minute demo and we'll show you exactly how it works for your team.

The land acquisition CRM built for teams that mail consistently, track performance and close deals. Everything your team needs in one place.

By subscribing you agree to with our Privacy Policy and provide consent to receive updates from our company.

© 2026 Pebble REI Inc. All rights reserved.

See Pebble in action.

Book a 30-minute demo and we'll show you exactly how it works for your team.

The land acquisition CRM built for teams that mail consistently, track performance and close deals. Everything your team needs in one place.

By subscribing you agree to with our Privacy Policy and provide consent to receive updates from our company.

© 2026 Pebble REI Inc. All rights reserved.

See Pebble in action.
Book a 30-minute demo and we'll show you exactly how it works for your team.

The land acquisition CRM built for teams that mail consistently, track performance and close deals. Everything your team needs in one place.

By subscribing you agree to with our Privacy Policy and provide consent to receive updates from our company.

© 2026 Pebble REI Inc. All rights reserved.