Why This 27 Year Old Quit House Wholesaling to Make $2M Flipping Land | Caleb Milobsky

The MORE Show

Most real estate investors are so focused on houses they have completely overlooked one of the simplest and most scalable paths to seven figures in this industry. In this episode of The M.O.R.E. Show, Justin Colby sits down with Caleb Milobsky, a 27-year-old land wholesaler who transitioned from flipping houses to flipping land  and built a business doing over $2 million a year in the process. Caleb breaks down exactly why land has fewer variables than houses, how he sources deals across 15 states using SMS outreach, why his spreads are larger than anything he made wholesaling houses, and the exact system he uses to hit the same lists seven times until sellers respond.

KEY TOPICS COVERED:

  • Why land wholesaling is simpler and more scalable than house wholesaling
  • How Caleb built a $2 million a year business flipping land at 27 years old
  • How to find and evaluate land deals using Land Insights heat map data
  • Why Caleb sends SMS to a million land owners a month — and how the system works
  • The seven touch frequency strategy that closed a $115K deal in 45 days
  • How to do land deals remotely across 15 states without ever visiting the property

️ Key Moments:

00:00 — Introduction: why he quit wholesaling houses

00:43 — Why land has fewer variables than houses

01:35 — Building a $2 million a year land business

02:00 — How land wholesaling works for beginners

02:50 — Land Insights software explained heat maps and county selection

03:26 — SMS outreach at scale, a million texts a month

06:00 — How to evaluate land deals and what to look for

10:00 — Wetlands, floodplains, and due diligence for land

15:00 — How Caleb sources deals across 15 states remotely

20:00 — Pricing, spreads, and what land deals actually pay

25:00 — The acquisition process from first contact to close

31:10 — The seven touch frequency strategy, $115K deal example

33:50 — Where to find Caleb Phillips and his free community

Connect with Caleb Milobsky :

YouTube: @Caleb_Flips_Land

Instagram: @Cmilobsky

About The M.O.R.E. Show:

The M.O.R.E. Show is hosted by Justin Colby and is dedicated to helping real estate professionals, investors, and entrepreneurs maximize opportunity in any market. New episodes every week.

Learn more: www.timeformore.com

Invest with Elevest Capital: www.elevestcapital.com


Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

More description

Most real estate investors are so focused on houses they have completely overlooked one of the simplest and most scalable paths to seven figures in this industry. In this episode of The M.O.R.E. Show, Justin Colby sits down with Caleb Milobsky, a 27-year-old land wholesaler who transitioned from flipping houses to flipping land  and built a business doing over $2 million a year in the process. Caleb breaks down exactly why land has fewer variables than houses, how he sources deals across 15 states using SMS outreach, why his spreads are larger than anything he made wholesaling houses, and the exact system he uses to hit the same lists seven times until sellers respond.

KEY TOPICS COVERED:

  • Why land wholesaling is simpler and more scalable than house wholesaling
  • How Caleb built a $2 million a year business flipping land at 27 years old
  • How to find and evaluate land deals using Land Insights heat map data
  • Why Caleb sends SMS to a million land owners a month — and how the system works
  • The seven touch frequency strategy that closed a $115K deal in 45 days
  • How to do land deals remotely across 15 states without ever visiting the property

️ Key Moments:

00:00 — Introduction: why he quit wholesaling houses

00:43 — Why land has fewer variables than houses

01:35 — Building a $2 million a year land business

02:00 — How land wholesaling works for beginners

02:50 — Land Insights software explained heat maps and county selection

03:26 — SMS outreach at scale, a million texts a month

06:00 — How to evaluate land deals and what to look for

10:00 — Wetlands, floodplains, and due diligence for land

15:00 — How Caleb sources deals across 15 states remotely

20:00 — Pricing, spreads, and what land deals actually pay

25:00 — The acquisition process from first contact to close

31:10 — The seven touch frequency strategy, $115K deal example

33:50 — Where to find Caleb Phillips and his free community

Connect with Caleb Milobsky :

YouTube: @Caleb_Flips_Land

Instagram: @Cmilobsky

About The M.O.R.E. Show:

The M.O.R.E. Show is hosted by Justin Colby and is dedicated to helping real estate professionals, investors, and entrepreneurs maximize opportunity in any market. New episodes every week.

Learn more: www.timeformore.com

Invest with Elevest Capital: www.elevestcapital.com


Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

2026-09-08 35 min
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