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

What happens when life knocks you flat, your business burns you out, and your next move isn’t obvious?

Most people wait for clarity. Alan Underwood started building anyway.

In this episode, Kristi and Raphael sit down with Alan, a high-performance coach and real estate developer who went from owning restaurants to reshaping his entire life around purpose, discipline, and community-focused development. Alan talks openly about the years he spent chasing work that drained him, the moment he realized he needed a different path, and the slow climb into a career that finally aligned with who he wanted to become.

His story is raw and real: navigating the entitlement process without a roadmap, pushing through doubt, learning to take imperfect action, and discovering that the right mindset isn’t just helpful in development, it is the foundation.

This episode is for anyone who’s rebuilding, starting over, or grinding quietly toward a project that feels bigger than their current resources. Alan’s journey proves that you don’t need certainty to get moving. You just need the courage to bet on yourself.

What We Cover:

✅ How burnout from restaurant ownership pushed Alan to rethink everything

✅ The shift from chasing money to building a life with purpose

✅ Why action beats perfection in development and entrepreneurship

✅ Navigating the entitlement process without experience

✅ Alan’s community-first approach informed by personal challenges

✅ His commitment to service through Angel Flight West

✅ What’s next for his development journey and coaching work

✅ Alan’s advice to anyone trying to step into real estate development for the first time

Bold Truth:

You don’t rise to the level of your resources. You rise to the level of your grit and your willingness to act before you feel ready.

🎧 Listen now to hear how Alan trusted the process, navigated setbacks with grit, and found out that the project that changes your life is often the one you choose to start before you’re prepared.

Connect with Alan:

🌐 Website: https://thealanunderwood.com/

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

💼 LinkedIn: https://www.linkedin.com/in/the-alan-underwood/

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 Podcast and Guests

01:26 Alan Underwood's Background and Journey

06:46 Transitioning from Restaurants to Real Estate

09:46 Lessons from Entrepreneurship and Grit

16:37 The Shift to Real Estate Development

19:43 The 100-Unit Apartment Complex Experience

25:03 Challenges in the Entitlement Process

28:48 Navigating Utility Challenges in Development

30:34 Finding Motivation Through Adversity

34:01 The Importance of Taking Action

36:59 Overcoming Analysis Paralysis in Investing

41:08 Community-Driven Development and ADUs

45:22 The Impact of Angel Flight West

52:02 Future Aspirations and Legacy Building

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

What happens when your first big project goes sideways, the money runs tight, and every choice feels like the wrong one?Most people quit. Brett McManus didn’t.In this raw and unfiltered conversation, Kristi and Raphael sit down with Brett McManus, a local developer who learned the business the hard way by getting punched in the mouth on his very first project. Brett walks through how a simple investment turned into a full-blown development education he never asked for. Budget surprises, contractor issues, lender pressure, and the emotional toll of feeling in over your head… he lived every line of that story.But instead of running, Brett got obsessed. He found better partners, learned how to build a team, figured out how to navigate city requirements, and rebuilt his confidence one problem at a time. This episode matters because Brett’s journey is exactly what development looks like for real people building projects in their own backyard, messy, humbling, and worth it.What We Cover: ✅ How Brett stumbled into development before he even realized that’s what he was doing ✅ The moment he knew he was in trouble and couldn’t turn back ✅ What really happens when you choose the wrong contractor ✅ How lender expectations and cost overruns pushed him to rethink everything ✅ The emotional side of development that no one talks about ✅ Why the right partners, operators, and local professionals changed the trajectory of his business ✅ What Brett wishes he knew before ever touching his first project ✅ How he rebuilt trust, systems, and confidence for the deals he’s now taking onBold Truth: Real development isn’t clean or glamorous. It’s survived by the people who stay in the ring long enough to figure it out.🎧 Listen now to hear how Brett learned the hard way, stayed in the game when it got messy, and discovered that the next big win in your community is closer than you think.Connect with Brett: 📲 Instagram: https://www.instagram.com/innvestors/ 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 Real Estate Development Journey00:31 Understanding Market Fit in Hospitality#localrealestatedeveloper #realestateinvesting #womeninrealestate #mindsetmatters #communitydevelopment #realestatejourney #propertyinvestor #infilldevelopment #therealestatedeveloper #partnerships #elevateswfl

What if the biggest housing crisis of our lifetime isn’t a policy problem… but a leadership problem?

And what if the next wave of community builders won’t come from corporate boardrooms, but from people who actually care about the places they live?

In this episode, Kristi and Raphael sit down with Evan Holladay, founder of Holladay Ventures, a developer who went from a curious college student to building affordable housing communities across the country. This conversation gets real about what it takes to build locally when the odds feel stacked against you: broken systems, slow approvals, tight margins, and the weight of knowing that every delay affects real families.

Evan breaks down how he found his way into development through service work and student housing, how early mentors shaped his mindset, and why he believes affordable housing is not just a business, it's a responsibility. His story is a reminder that you don’t need to start with experience, money, or a perfect roadmap. You just need a mission big enough to keep going when everything gets hard.

What We Cover:

✅ How a college campus project sparked Evan’s passion for real estate

✅ The mentorship that shaped his path into affordable housing

✅ Why the housing crisis needs developers who actually care

✅ How Holladay Ventures evaluates deals, partnerships, and communities

✅ The real challenges of affordable housing: timelines, approvals, and razor-thin margins

✅ How setbacks shaped Evan’s leadership and long-term vision

✅ His nationwide mission to expand affordable and attainable housing

Bold Truth:

Local developers aren’t just building properties. They’re building the future of their communities and the future belongs to the ones willing to take responsibility for the people who live in them.

🎧 Listen now to hear how Evan turned a spark of curiosity into a mission-driven development career and why the next person who transforms your community might be you.

Connect with Evan:

🌐 Website: http://www.holladayventures.com/

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

💼 LinkedIn: https://www.linkedin.com/in/evanholladay/

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

01:06 Evan Holiday's Journey into Real Estate Development

04:14 The Importance of Apprenticeship in Real Estate

05:19 Transitioning to Nashville: A Strategic Move

08:19 Catalysts for Starting Holiday Ventures

13:42 First Independent Project: From House Hacking to Multifamily

18:52 Navigating Partnerships: Lessons Learned

23:31 Securing the First Affordable Housing Opportunity

24:19 Creative Solutions for Nonprofit Development

30:19 Building Community Through Affordable Housing

33:59 The Drive Behind Entrepreneurial Success

37:51 Collaborative Models for Nonprofit Partnerships

40:24 Empowering Future Developers Through Education

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

Most people wait for the perfect moment. Jeremiah Parker ran toward the fire instead.

Before he ever closed a deal, Jeremiah spent years as a career firefighter, working long shifts, responding under pressure, and learning how to stay calm when everything around him was chaos. Those skills followed him into real estate, where he started as a broker, stacked reps, and eventually stepped into development with the same mindset that kept him steady on the job: trust your training, move with purpose, and don’t freeze when things get hard.

In this episode, Kristi and Raphael sit down with Jeremiah to explore how a firefighter with no safety net became a full-time investor and developer by confronting fear, building a reliable team, and taking on projects most people would talk themselves out of. His story is raw, local, and all real life: the early struggles, the mindset shifts, the deals that forced him to grow, and the deeper reason he’s building something bigger than himself.

What We Cover:

✅ How firefighting shaped Jeremiah’s perspective, discipline, and decision-making

✅ Why he got into real estate and how becoming a broker opened doors

✅ The fear, hesitation, and mental battles behind his first investment moves

✅ How he built a trusted team and why the right people change everything

✅ The challenges of scaling from small deals to larger development projects

✅ What drives him to keep building, even when the path isn’t clear

Bold Truth: Real estate doesn’t reward the fearless. It rewards the people who feel the fear, step forward anyway, and build something their community can point to and say, that came from one of us.

🎧 Listen now to hear how Jeremiah turned fear into action and built a team and a strategy that allowed him to scale and why the next project transforming your community could be yours.

Connect with Jeremiah:

📲 Facebook: https://www.facebook.com/p/Jeremiah-Parker-Real-Estate-Broker-at-EXIT-Realty-CW-100057358813554/

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 Real Estate Development

01:32 Transitioning from W2 to Full-Time Investing

05:45 Overcoming Fear in Real Estate

11:10 The Importance of Taking Action

12:36 From Flips to New Construction

17:04 Navigating the Development Process

18:25 Building a Strong Team for Growth

21:31 Building Strong Relationships with Contractors

22:55 The Importance of Continuous Learning

23:13 Finding Motivation in Personal Goals

25:48 The Deeper Why Behind Development

26:33 Affordable Housing Initiatives

28:14 Navigating Financing and Development Challenges

29:48 Understanding Land Costs and Development Strategies

33:51 Advice for Aspiring Developers

37:48 Connecting with Jeremiah

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

Most people look at development and see something out of reach. Katie Neason looked at it and asked a different question: What if becoming a developer is less about expertise and more about identity?In this episode, Kristi and Raphael sit down with Katie for a grounded, brutally honest look at what it really takes to build where you live. From navigating infill projects and fighting “analysis paralysis” to learning to trust small first moves, Katie breaks down why local development isn’t reserved for the chosen few. It’s for anyone willing to learn the rules, build the right relationships, and take action before they feel ready.Katie shares the mindset shifts behind her Rookie Redeveloper program, how she helps everyday people see themselves as developers, and why small neighborhood projects can have the biggest long-term impact.Her story is a reminder that you don’t need to start with land, capital, or confidence. You just need to redefine who you are and take the next step in front of you.What We Cover: ✅ Why your identity matters more than your skill set ✅ How small infill lots create outsized neighborhood impact ✅ The power of removing barriers through clear guidance and community ✅ The difference between owning a property and shaping a place ✅ Why analysis paralysis stops most beginners ✅ How Katie teaches first-timers to take action, not wait for permissionBold Truth:The moment you decide to see yourself as a developer is the moment your entire path changes. Building begins with identity, not experience.🎧 Listen now to hear how Katie breaks down the barriers to getting started and why the next person shaping your community might just be you.Connect with Katie: 🌐 Website: https://www.katieneason.com/ 📲 Instagram: https://www.instagram.com/katiedevelops/ 💼 LinkedIn: https://www.linkedin.com/in/katie-neason-89b4a7a/ 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 Local Development01:42 Katie Neason's Journey into Development03:31 Navigating Challenges in Development07:40 Understanding City Planning and Zoning11:58 Building Trust with the City12:28 Financing Development Projects20:05 Adapting to Changing Banking Relationships22:26 Innovative Cottage Cluster Development29:22 Navigating Community Responsibilities30:12 The Importance of Local Climate Awareness31:21 Partnership Dynamics in Development33:34 Choosing the Right Investors35:36 Understanding Market Cycles39:15 The Value of Local Development41:08 Incremental Development Strategies42:09 Advice for Aspiring Developers49:06 Community-Driven Development Explained52:07 Current and Future Projects#localrealestatedeveloper #realestateinvesting #womeninrealestate #mindsetmatters #communitydevelopment #realestatejourney #propertyinvestor #infilldevelopment #therealestatedeveloper #partnerships #elevateswfl