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Hidden Gems: Meet Kelsie LPJ of Raspberry & Oak Investments

Today we’d like to introduce you to Kelsie LPJ.

Kelsie, we appreciate you taking the time to share your story with us today. Where does your story begin?
My journey into real estate development has actually been fairly traditional in a lot of ways. I grew up surrounded by real estate investing and construction, but for a long time, I lacked the confidence to believe I could take everything I’d learned and build something of my own. Looking back, I realize I was preparing for this path long before I had the confidence to pursue it.

I grew up with parents who were both teachers and real estate investors. They taught me early on how to be frugal, resourceful, and creative with money. Some of my earliest memories are of small construction sites, watching my dad build our family home with his own hands, or being part of the family’s very affordable (and conveniently available) labor force on my parents’ latest investment property. Long before I knew what the BRRRR method was, I was watching my parents buy, renovate, rent, refinance, and repeat. Real estate was simply part of our everyday life.

Despite growing up around it, I didn’t initially pursue real estate as a career. I’ve always been a creative person, which led me to earn my Bachelor of Fine Arts in Sculpture and later my Master’s in Teaching. I taught abroad in China and eventually taught art here in Oregon. I love teaching, but I’ve also always had an entrepreneurial side and a desire to create something of my own.

After becoming a mom, I started exploring real estate investing more seriously. I wanted to create financial freedom for my family while building a career that allowed me to be both an involved mother and an ambitious businesswoman. What started with investing eventually grew into a passion for creative financing, development, and finding opportunities in places other people might overlook.

Although I grew up around real estate, I didn’t enter development with a large amount of capital or a formal background in construction management. I had to learn how to put deals together, build relationships, find financing, and navigate projects that were much bigger than anything I’d done before.

One of my biggest milestones was developing a 15-unit cottage cluster in Monmouth, Oregon, with 100% financing. I secured a $2.5 million construction loan and completed the project in just 11 months. That experience made me realize that everything I’d experienced and learned throughout my life had been preparing me for that moment. Every job, every project, every challenge, and even the smallest conversations or pieces of knowledge I’d picked up along the way had quietly given me the tools I needed to succeed. Nothing was wasted. It all added up, even when I couldn’t see how those experiences would connect at the time.

Today, I’m a full-time real estate investor and developer, working on residential and commercial projects, revitalizing underutilized spaces, and creating opportunities for other small businesses and the communities around them.

I think the common thread throughout my story has always been creativity. Whether it was sculpture, teaching, investing, or developing buildings, I’ve always loved imagining what something could become and then figuring out how to make it happen.

My goal has never been to own the most properties or build the biggest portfolio. I want to create the most value, build things that positively impact the communities around me, and create a big, fulfilling life for my family.

In a lot of ways, I feel like I’m taking the lessons my parents taught me and applying them on a different scale. I’m incredibly grateful for the foundation they gave me, and I’m excited to see just how much more I can build from it. I’m still very much at the beginning of what I hope to accomplish.

We all face challenges, but looking back would you describe it as a relatively smooth road?
Absolutely not, and I don’t think I’d have learned nearly as much if it had been!

One of my biggest struggles has actually been confidence. I grew up around real estate, had a great foundation, and had accumulated so much knowledge through different experiences, but for a long time I struggled to give myself permission to step into the future I wanted for myself. I was limiting my own potential far more than I realized. It’s funny how you can have so many of the tools you need and still be the person standing in your own way.

Financing has certainly been another challenge. Real estate development is incredibly capital-intensive, and I didn’t start with millions of dollars or the ability to personally fund large projects. I had to get creative, learn how to structure deals, build relationships, and convince people to believe in projects that sometimes existed only on paper. There were plenty of people who didn’t think I’d be able to secure financing for my 15-unit development, let alone actually build it. I think that experience taught me a lot about perseverance and trusting my own abilities.

Another major challenge has been navigating entrepreneurship alongside motherhood. I’m raising three young children while building businesses and managing construction projects, and there is no magical balance where everything gets equal attention all the time. I’ve had difficult pregnancies, health challenges, and seasons where I simply couldn’t show up at the capacity I wanted to. Learning to give myself grace while still allowing myself to be ambitious has been a huge part of my growth.

And then there are the everyday realities of development. Delays, unexpected expenses, contractors, financing hurdles, permitting, and a seemingly endless list of problems that need solving. I’ve learned that being a developer doesn’t mean knowing all the answers. It means being willing to find them, make decisions, take responsibility, and keep moving forward.

I think the biggest shift for me has been realizing that confidence isn’t necessarily something you have before you do something difficult. Sometimes you have to do the difficult thing first, and the confidence comes afterward.

I still have moments of doubt, and I certainly don’t have everything figured out. But I’ve learned to trust that I’m resourceful enough to find a way through most challenges. Every obstacle has taught me something, and those lessons have become some of my most valuable assets.

I don’t necessarily think success comes from having an easier path or being more talented than the next person. I think a lot of it comes down to being willing to try, being willing to learn, and not letting the fear of getting something wrong stop you from building something wonderful.

As you know, we’re big fans of Raspberry & Oak Investments . For our readers who might not be as familiar what can you tell them about the brand?
At the heart of what I do is real estate development, but I like to think of my work as creating opportunities and finding potential in places that others might overlook.

Through my real estate investment and development businesses, I focus on residential and commercial projects, creative financing, and revitalizing underutilized properties. I especially enjoy projects that require a little imagination, whether that’s building new housing, reimagining an older commercial building, or creating spaces that help other small businesses grow.

I think what sets me apart is my approach to problem-solving. I don’t necessarily look at a property and ask what I can afford to do with it. I ask what it could become and then work backward to figure out how to make that happen. Creative financing has become a huge part of my business because I believe a lack of traditional resources doesn’t always have to mean a lack of opportunity. Sometimes it just means you need a different structure, the right relationships, and a willingness to think creatively.

My background in art and education also influences how I approach development. I’m very involved in the design and vision of my projects, and I care deeply about how spaces look, feel, and function for the people who use them. I don’t want to build something simply because the numbers work. I want the finished project to contribute something meaningful to its surroundings.

One of the projects I’m most proud of is the 15-unit cottage cluster I developed in Monmouth, Oregon. It was my first ground-up multifamily development, financed with a $2.5 million construction loan and completed in just 11 months. Beyond the financial accomplishment, I’m proud that we created new housing in a community that needed it and demonstrated that smaller-scale development can be both financially viable and thoughtfully designed.

More recently, I’ve been expanding into commercial redevelopment and community-focused spaces in downtown Salem. One project I’m particularly excited about is Shui, a coworking and business community designed to bring entrepreneurs, creatives, and small business owners together. Alongside that, I’m working to bring new life to existing commercial spaces through synergetic businesses and services. I love the idea that a real estate project can do more than improve a building. It can create a place where people connect, businesses grow, and an entire block starts to feel more alive.

What I’m most proud of, brand-wise, is that my work is becoming a reflection of what I genuinely value: creativity, resourcefulness, community, and opportunity. I’m not interested in development just for the sake of accumulating properties. I want to create spaces that people are excited to live in, work in, and visit.

I also hope that sharing my projects, including the financing, challenges, mistakes, and successes, makes real estate development feel more accessible to others. I especially love encouraging women and mothers who have big ambitions but might not yet see themselves in industries like construction and development.

Ultimately, I want people to know that my business is about more than buildings. It’s about recognizing potential, creating value, and being willing to take an idea from something that exists only in your imagination to something real that other people get to experience.

I want to be known not necessarily for how much I’ve built, but for the value I’ve created along the way.

Do you have recommendations for books, apps, blogs, etc?
I’m a big believer that the things we read, listen to, and the people we surround ourselves with shape how we see the world. I love learning, and I’m naturally curious about just about everything, so my favorite resources aren’t always directly related to business or real estate.

Some of my favorite books are *The Alchemist* by Paulo Coelho, *Fahrenheit 451* by Ray Bradbury, *Animal Farm* by George Orwell, and *Shoe Dog* by Phil Knight. They’re all very different books, but I think that’s why I love them. *The Alchemist* is a beautiful reminder to pursue the life you feel called to live, even when the path isn’t clear. *Fahrenheit 451* and *Animal Farm* challenge you to think critically, question the world around you, and recognize the importance of independent thought. And *Shoe Dog* is such a great look at the messy, uncertain, and sometimes completely chaotic reality of building something from nothing.

For podcasts, I really enjoy *Deal Junkies* and *Realized Gains*. I love hearing people talk through real deals, creative financing, investing, and the lessons they’ve learned through experience. There’s so much value in listening to how other people think and solve problems. And when I need something completely unrelated to business and just want a good laugh, *Toni and Ryan* is a favorite!

I also use ChatGPT & Claude regularly to brainstorm, organize my thoughts, research ideas, and work through problems. Between running businesses, managing development projects, and raising three kids, anything that helps me turn the million ideas in my head into something actionable is incredibly valuable.

But I think one of my greatest resources will always be other people. I genuinely believe you can learn something from almost anyone. Some of the most valuable things I’ve learned have come from seemingly insignificant conversations, random questions, or experiences that had nothing to do with what I’m doing today.

I don’t think there’s one book, podcast, or piece of advice that changes everything. I think it’s the accumulation of all those little bits of knowledge over time. You never really know when something you learned years ago will become exactly what you need to take your next big step.

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Modern gray houses beside a paved parking area with white lane markings.

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Two dark, modern houses with large windows stand beside a paved walkway under a cloudy sky.

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