What if the people closest to you can’t see the vision you’re building… but you know deep down you’re right?

In this episode, Kristi and Raphael sit down with Jacqueline DiMaggio, a designer-turned-developer who’s quietly building a hospitality ecosystem in rural Wisconsin. What started as two Airbnbs with a pond and a beach turned into land acquisitions, a multi-phase farmhouse project, and a growing design and co-hosting business that locals now recognize by name.

Jacqueline shares the real story behind creating experiences guests actually feel, navigating family skepticism, partnering with her dad after decades of him swearing he’d never partner with anyone again, and learning to follow the deals that give you goosebumps instead of the ones that drain your soul.

This episode is a reminder that local development isn’t just spreadsheets. It’s intuition, it’s walkability, it’s boots on the ground, and it’s knowing when the universe is redirecting you toward something better.

What We Cover:

✅ Following the “goosebumps” instead of forcing a bad deal

✅ Why boots on the ground beats any spreadsheet

✅ How walkability and vibe shape real retail markets

✅ Building a hospitality experience where families can unplug

✅ Partnering with family even when they don’t see the vision

✅ Why real estate can be forgiving when you buy in the right areas

✅ How Jacqueline built a design and co-hosting business from her own Airbnbs

✅ Growing a team so you can work in your zone of genius

✅ Using cash flow from hospitality to fund long-term development

✅ Staying patient and focused while carrying a multi-phase land project

Bold Truth:

You can’t spreadsheet your way into vision. The people who build locally are the ones who trust their gut, walk the land, and create places that outlive the doubts around them.

🎧 Listen now to hear how Jacqueline followed the goosebumps, pushed through the doubters, and proved that the project that changes your life is usually the one you build even when no one else can see the vision.

Connect with Jacqueline:

🌐 Website: https://jpatriciadesign.com/

📲 Instagram: https://www.instagram.com/jacqueline_dimaggio/

💼 LinkedIn: https://www.linkedin.com/in/jacqueline-dimaggio-aab508315/

Listen + Subscribe:

Watch full episodes on YouTube or listen on Spotify & Apple Podcasts.

Want more from Kristi?

Hear how she’s helping locals become developers in their own communities without the gatekeeping.

🎧 Local Real Estate Developer Podcast Playlist →

👉 Ready to become a local developer in your town? Apply for the Mentorship:

https://www.localrealestatedeveloper.com/dev-mentorship

🎧 Access all platforms, the Developer Vault, and more:

https://linktr.ee/localrealestatedeveloper

🎬 Chapters

00:00 Introduction to the Local Real Estate Developer Podcast

01:44 Jacqueline's Journey into Real Estate Development

06:58 Vision for the 200-Acre Property

09:54 Community Engagement and Overcoming Challenges

17:42 Building Partnerships in a New Market

22:57 Phased Approach to Development

26:49 Bootstrapping the Project

33:20 Advice for Aspiring Developers

39:45 Future Plans and Collaborations

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