After years glued to a screen building income through social media, Christopher Oester hit a breaking point.He was burned out. Tired. And looking for a way to turn short term hustle into something real.So he took a leap. A big one.In this episode of the Local Real Estate Developer Podcast, Kristi and Raphael sit down with Chris to unpack what it actually looks like to jump into ground up development with no construction background, no design experience, and a whole lot on the line.From buying his first lot in a conservation district to taking on three builds at once, serving as his own general contractor, and staring down massive monthly interest payments, Chris shares the unfiltered reality of learning development in real time.This is a raw conversation about fear, financing, partnerships, mentorship, and the mental pressure that comes with building something from the ground up. It is not about getting it perfect. It is about taking responsibility, asking questions, and continuing to show up when things get uncomfortable.If you are a local investor wondering whether development is really possible for someone without experience, this episode pulls the curtain back and shows you what it actually takes.What We Cover: ✅ Transitioning from social media income to real estate development ✅ Why starting in Dallas made more sense than Miami ✅ Buying a lot in a conservation district and what that really means ✅ Acting as your own general contractor with no prior experience ✅ The financial reality of interest payments, soft costs, and lending terms ✅ How mentors and partners actually work in practice ✅ Why asking questions early can save time, money, and stress ✅ The mindset required to keep going when fear and pressure set in ✅ How development impacts community and why locals matterBold Truth:Local development is not about knowing everything before you start. It is about taking initiative, staying accountable, and being willing to learn in public while building something that outlives you.🎧 Listen now to hear how Chris took action before he felt ready, learned development in real time, and proved that the deal that changes your life is often the one you commit to before you have all the answers.Connect with Christopher: 📲 Instagram: https://www.instagram.com/itschrisdifferent/ 📲 Tiktok: www.tiktok.com/t/ZT6GjapSC/ 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🎬 Chapters00:00 Introduction to the Local Real Estate Developer Podcast00:32 Chris Different's Journey into Real Estate03:34 The Leap of Faith: Transitioning from Social Media to Development06:21 Understanding the Challenges of Development11:11 Navigating Conservation Districts and Regulations13:38 Current Construction Progress and General Contracting16:00 Financial Realities of Real Estate Development19:11 Future Plans: Selling vs. Holding Properties21:31 Finding Motivation in Adversity24:00 The Importance of Loving What You Do25:57 Embracing Failure as a Learning Tool29:16 The Value of Mentorship and Partnerships33:07 Advice for New Developers35:23 Community-Driven Development37:17 Future Projects and Aspirations#localrealestatedeveloper #realestateinvesting #womeninrealestate #mindsetmatters #communitydevelopment #realestatejourney #propertyinvestor #infilldevelopment #therealestatedeveloper #partnerships #elevateswfl

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

#localrealestatedeveloper #realestateinvesting #womeninrealestate #mindsetmatters #communitydevelopment #realestatejourney #propertyinvestor #infilldevelopment #therealestatedeveloper #partnerships #elevateswfl

If you’ve been rocking with us all year, listening, learning, sending messages, showing up every week, thank you. Truly.In this short but powerful episode, Kristi and Raphael pull back the curtain and share what this podcast is really about: not big-money developers, not corporate initiatives, but locals with grit who are stepping up to shape their cities one project at a time.It’s a thank-you, a reset, and a rally cry for the next chapter of local development.Whether you’re already building or still gathering the courage to start, this episode is a reminder: you’re part of something bigger than your zip code.What We Talk About in This Year-End Message: ✅ Why this podcast was created and who it’s REALLY for ✅ The community impact Kristi and Raphael are seeing across the country ✅ The mission for 2025 and how locals are taking development into their own hands ✅ A genuine thank-you to listeners, builders, and future developers ✅ A behind-the-scenes look at what it’s like hosting this platform every weekBold Takeaway:Local development isn’t a trend, it’s a movement. And every movement needs people willing to build where they stand.Connect with Kristi: 🌐 Website: https://kristikandel.com/ 📲 Instagram: https://www.instagram.com/kristikandel/ 💼 LinkedIn: https://www.linkedin.com/in/kristi-kandel-4b650a12/ Connect with Raphael: 🌐 Website: http://www.raphaelcollazo.com/ 📲 Instagram: https://www.instagram.com/commercial_louisville/ 💼 LinkedIn: https://www.linkedin.com/in/raphaelcollazo/ 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#localrealestatedeveloper #realestateinvesting #womeninrealestate #mindsetmatters #communitydevelopment #realestatejourney #propertyinvestor #infilldevelopment #therealestatedeveloper #partnerships #elevateswfl