Episode 7: From Data to Deals — How “Jack & Jill” Built a Land Empire from the Back of a Boat with Jack Butala & Jill DeWit

What if you could flip land from anywhere in the world — even from the back of a boat? In this episode, Lance talks with Jack and Jill, the powerhouse couple behind Land Academy, who’ve completed over 16,000 land transactions and built a thriving community of data-driven investors. They share how they turned recession setbacks into opportunity, what makes land the simplest and most overlooked niche in real estate, and why their business model thrives on partnerships, precision, and a little bit of humor.

Episode 7: From Data to Deals — How “Jack & Jill” Built a Land Empire from the Back of a Boat

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Guest Speakers: Jack Butala & Jill DeWit, Co-Founders of Land Academy

What if you could flip land from anywhere in the world — even from the back of a boat?

In this episode, Lance talks with Jack and Jill, the powerhouse couple behind Land Academy, who’ve completed over 16,000 land transactions and built a thriving community of data-driven investors.

They share how they turned recession setbacks into opportunity, what makes land the simplest and most overlooked niche in real estate, and why their business model thrives on partnerships, precision, and a little bit of humor.

Key Takeaways:

  • Why land investing beats traditional real estate: No tenants, no toilets, no repairs — and it’s all data-driven.
  • The “Red-Yellow-Green” test: Jack’s analytical system for picking profitable markets.
  • How they built DealCompete.com: a complete tool to automate deal analysis, marketing, and funding.
  • The power of partnerships: How Land Academy members fund and flip deals together.
  • Mindset + systems: What separates successful investors from the ones who quit too
  • soon.
  • Couples in business: How to divide lanes, stay sane, and scale together (with laughter and lessons).

Episode Timestamps

  • 00:30 – Welcome to The Potentializer Podcast and today’s niche: the power of land investing.
  • 02:00 – Meet Jack & Jill: how one $8K deal turned into 16,000+ transactions.
  • 05:00 – From the 2008 crash to creating Land Academy and a community of investors.
  • 07:00 – Why land is the simplest, most overlooked asset — and how you can run it “from the back of a boat.”
  • 09:30 – Data over feelings: sending priced mailers and using analytics to pick markets.
  • 12:30 – The “Red-Yellow-Green” test — Jack’s formula for knowing where to buy.
  • 15:00 – Typical deal numbers: buy at 20 % of retail, sell at 50–75 %, and move in weeks.
  • 18:00 – Funding partnerships: how Land Academy members find deals and get financed.
  • 22:00 – Couples in business: dividing lanes, trusting strengths, and keeping it fun.
  • 26:30 – Mindset & motivation: what really separates successful investors.
  • 30:00 – Resources, community, and why Jack & Jill say they’ll never truly retire.

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