Let’s be honest: most investing advice out there is complicated, expensive, and drier than yesterday’s toast. That’s where I come in. Real stories, courses that walk you through it one step at a time, and a community of investors who’ll tell you what their mistakes cost. And if you’re doing development with your spouse, learn it together. It goes a lot smoother when you both know what a draw schedule is before the lender asks.
Investors asking the same questions you are, and a few who learned the answers the hard way. Building with your spouse? Bring them. Deals go smoother when you both know the numbers.
Hi, I’m Kelsie! The investor behind Raspberry & Oak and your new friend in building wealth. I bought my first rental while still grinding away at my day job, found out that financial freedom really is built one property at a time, and got completely HOOKED. Now my rentals cover my life, and I’m here to help you build yours, too.
Let’s set the scene. I grew up on Rich Dad Poor Dad. My parents handed me the mindset early, so I always knew money was supposed to work for you instead of the other way around. Knowing that and actually doing it are two very different things, and nobody was going to build the portfolio for me.
I got obsessed with learning everything I could and surrounded myself with investors who’d already done it. Then I put in the long, unglamorous work of learning this business right here in Oregon, so that you don’t have to learn it the slow way.
Since Going Full Time…
After my 9 to 5, I kept working my 5 to 9 to grow the portfolio. Partnerships, private capital, and a whole lot of consistency stacked doors until my rental income replaced my paycheck. Crazy, right?
These days I’ve done a little of everything: single family homes, small multifamily, short term and mid term rentals, flips, ground up development, and (my personal favorite) long term rentals. What I actually love teaching is deal structure. Most deals don’t pencil the way they’re listed. Get creative with the financing, the terms, and who you partner with, and a deal that looked dead on paper starts to work. That’s the part nobody showed me early on, so it’s the part I teach.
How I Got Here
2020
Wholesaled and structured my first creative deal
2021
Bought my first development property
2024
Went to my first real estate event and meetups
Started my cottages with an infinite cash on cash return
2025
Completed and stabilized the cottages
Created $1.6M in equity on a project I started with $0
2026
Scaled with partnerships & private money
Now
Teaching others how to reach financial freedom through real estate
Still raising private capital for our next projects
Let’s Build YOUR Portfolio & Achieve Financial Freedom
Rooted in Rentals
Your guide to buying your first rental and building income that lasts.
Ready to Build Wealth and Leave That 9 to 5 Behind?
Getting started in real estate can feel overwhelming. I get it. It’s a big investment, and I was terrified at first, too. Rooted in Rentals walks you through the whole thing one step at a time, from setting goals to picking up keys, taught by an investor who’s been through the thick of it. You get lifetime access, so you can work through it at your own pace on your own schedule.
This Is for You If…
You’re ready to buy your first rental and want to skip the classic beginner mistakes.
You’re spinning your wheels. Information overload has turned into analysis paralysis and you need a way out.
You’ve read the books and binged the podcasts but still can’t figure out how to actually start.
We’ll Cover
01. Roots first: mindset & goals +
Set yourself up for success before you buy anything
Create a vision that guides your goals & strategy
Break big goals into small, consistent action steps
02. Pick your strategy +
See every option from fully passive to very active
Weigh the pros and cons of each strategy for YOUR goals
Commit to one strategy (no shiny object syndrome here)
03. Choose your market +
Identify your competitive advantage in any market
Analyze the key metrics that match your goals
Narrow down to the one market you’ll zero in on
04. Build your core 5 team +
Know the “Core 5” members every investor needs
Find quality team members in any market
Use strategic questions to vet them like a pro
05. Analyze deals like a pro +
Build your personal “buy box” that defines a good deal for you
Source the inputs you need to analyze with confidence
Make decisions based on numbers and clear criteria
06. Financing & loan lingo +
Talk to lenders with confidence
Match loan options to different kinds of projects
Understand the timeline and process of getting funded
07. Making offers +
Know the main components of a strong offer
Track the major milestones after your offer is accepted
Make your offers more competitive
08. Due diligence +
Use checklists to guide every step of the process
Run physical, financial, and legal due diligence
Navigate renegotiations when surprises come up
09. Renovations +
Vet the right contractor for your project
Create a clear scope of work
Run renovations efficiently, even from far away
10. Property management +
Decide whether to manage it yourself or hire it out
Vet a property management company
Learn the basics of finding a quality tenant
Bonus: Systems to scale +
Ready to grow? Set up the key systems & processes that build a solid foundation for your next deal and every one after that.
I share both the ups AND the downs of investing. The wins feel that much sweeter after pushing through the challenges!
Small, consistent action wins any day. We turn overwhelm into momentum by breaking big goals into the very next step.
Simple + actionable = a recipe for success. No analysis paralysis here. You get a roadmap from start to finish.
Join the Investors Who Stopped Researching and Started Buying.
You’re on the List!
Check your inbox in the next few minutes. I’ll follow up personally with everything you need to get started.
Become a Passive Partner!
Want the benefits of investing in real estate without the work?
Invest Without the Stress
Short on time? Focused on your 9 to 5? Passive partnerships may be exactly what you’re looking for. Here are the two types:
Equity Partnerships.
Like the sound of more upside? In exchange for your investment, you get part ownership. The better the property performs, the better your return!
Think of yourself like the bank. In exchange for lending, you earn a fixed interest rate. We handle the work while you collect “mailbox money.” Investing without the headaches.
Private investments can be secured a few ways, most commonly through a personal guarantee backed by the borrower’s assets, or a mortgage that ties the loan to the physical property. Documents vary by deal, amount, structure, and investor preference.
What kind of returns are typical? +
Returns vary widely deal to deal, especially in an equity position where returns move with performance. If you’re curious about current opportunities, fill out the contact form and let’s chat!
When do I get my money back? +
Lending terms typically range from under a year to a few years, depending on the project.
How much do I need to invest? +
Minimums vary by deal. Reach out and we’ll walk through what’s open right now and whether it fits your goals.
I want to raise private money for MY deals. How do I learn? +
Learning to raise private capital was the key to growing my business fast! I created a workshop that teaches the ins and outs of finding, raising, and using private money. You’ll find it in the shop.
Let’s Grab Coffee and Talk Deals.
Tell me what you are looking for and I’ll reach out personally with what is open right now.
Got It, Thank You!
I read every one of these myself. Expect to hear from me within one business day so we can find a time to talk.
Taking it a step further, here are the books, podcasts, and channels that helped me build wealth. Click a spine to pull it off the shelf!
Long-Distance Real Estate Investing
Long-Distance Real Estate InvestingDavid Greene
Book
Long-Distance Real Estate Investing
By David Greene
The first real estate book I read! If you’re living in an expensive market, or your market doesn’t work for your strategy, this book opens up the possibility of investing out of state.
Raising Private Capital
Raising Private CapitalMatt Faircloth
Book
Raising Private Capital
By Matt Faircloth
The playbook for growing beyond your own savings. If you want to scale with other people’s money (the right way), start here.
Estimating Rehab Costs
Estimating Rehab CostsJ Scott
Book
Estimating Rehab Costs
By J Scott
Renovations are where deals are made or broken. This one taught me how to walk a property and budget the work with confidence.
The House Hacking Strategy
The House Hacking StrategyCraig Curelop
Book
The House Hacking Strategy
By Craig Curelop
If your down payment fund is small, house hacking is the cheapest door into real estate. A perfect blueprint for a first deal.
BiggerPockets Podcast
BiggerPockets PodcastPodcast
Podcast
BiggerPockets Podcast
Weekly episodes
Hundreds of investor interviews at every level. I listened on every commute while saving for my first deal. It’s free mentorship in your ears.
Rich Dad Poor Dad
Rich Dad Poor DadRobert Kiyosaki
Book
Rich Dad Poor Dad
By Robert Kiyosaki
The classic mindset shift: assets in, liabilities out. Read it early; it changes how you look at every dollar.
The Millionaire Real Estate Investor
The Millionaire Real Estate InvestorGary Keller
Book
The Millionaire Real Estate Investor
By Gary Keller
Models and frameworks from hundreds of investors. When you’re ready to think bigger than one door, this is the map.
The Essentials
Whether you’re a rookie or ready to #scaleup, these will help you level up your business.
Landlord Banking
One home for your rental finances: banking, bookkeeping, and rent collection built for landlords.
