I’m pulling back the curtain on how we got started in real estate investing. Spoiler alert: it all began with an Airbnb in our backyard. In this minisode, I’m sharing the behind-the-scenes of our six-year journey with short-term rentals—from building our ADU to navigating Portland’s ever-evolving STR laws, managing (and outsourcing) guests, and yes... restocking way too much toilet paper.

If you’re thinking about turning your space into a short-term rental or just curious about how STRs actually work, this episode is packed with honest insights, lessons learned, and practical tips for new and seasoned hosts alike. I’m also diving into what I believe is the next wave for real estate investors—and why the Airbnb model may not be the golden ticket it once was.

Here are the top takeaways from this episode:

1. Start with the Worst-Case Scenario to Run the Numbers

Before falling in love with Airbnb income projections, ground yourself in financial reality. Ann recommends always asking: Would this property still make sense as a long-term rental?

2. Know the Rules Before You Buy (and Expect Them to Change)

Short-term rental success isn’t just about aesthetics and occupancy—it's about legality. Understanding permitting, zoning, taxes, and even HOA restrictions can make or break your investment.

3. STRs Are Seasonal, Hands-On, and Require Replenishable Inventory

Cash flow might be stronger than long-term rentals, but you’re essentially running a mini hotel. STRs require ongoing expenses, restocking, and attention to comfort and cleanliness.

4. Property Management Isn’t All or Nothing, Find a Hybrid Model

If you don’t want to be glued to your phone managing guest check-ins, consider hybrid options. Tech tools and part-time managers can help balance profitability and peace of mind.

5. Trends Change, Be Willing to Evolve

Market cycles matter. Ann reminds us to zoom out and consider new models like midterm rentals or co-living before jumping into saturated strategies.

Want to learn more about real estate investing? Hop on the waitlist for the Soulful Investor Society, a community membership for real estate investors and those who'd like to get in the game. Once on the waitlist, you'll be the first to know when the doors open AND you'll get lots of amazing freebies, including a FREE 1:1 coaching session with me, where we'll map out your plan from start to finish, so you can finally buy that investment property and scale your portfolio.

You can also find me on IG @annreedandco where I share daily musings on real estate, mindfulness, being an almost empty nester, and more.

In today’s episode, I'm talking with Julie and Jaelle — two real estate agents turned real estate investors who are combining creative financing, smart renovations, and heart to shake up the investing space. We talk about seller financing strategies, fix and flip projects, and how they’re raising the next generation of investors (yes, their teens are on the job site!). Julie and Jaelle are the founders of Women Real Estate Investors of Oregon (WREIO) — a fast-growing, women-led real estate investing community that’s helping women take action and build generational wealth.

We dive into what it really takes to become a successful real estate investor, why community over competition is more than a catchphrase, and how intentional investing can create lasting impact.

Here are the top takeaways from this episode:

1. Real Estate as a Tool for Generational Wealth

Julie and Jaelle didn’t just find their way into real estate — they aligned around a shared mission to use it for long-term impact.

This shared vision has shaped their investing strategies, their business model, and how they involve their kids in the process.

2. Renovating for Profit—and for Purpose

Fix and flip isn’t just a hustle—it’s a smart, intentional strategy when the math checks out. These two make sure it aligns with their goals before diving in.

They also factor in the time-value equation and whether a project allows for family involvement, which ties back to their bigger “why.”

3. Seller Financing as a Creative Win-Win

Julie and Jaelle are using seller financing to structure deals that benefit everyone—especially the seller’s bottom line.

By negotiating directly, they were able to avoid extra fees, lower the interest rate, and create a smoother, more personal transaction.

4. Building a Women-Centered Investing Community

WREIO (Women Real Estate Investors of Oregon) began with a dozen women and now has over 1,100. It's become a hub of empowerment and action.

Whether they’re hosting in-person meetups, launching a virtual seminar series, or celebrating wins on Facebook, Julie and Jaelle are creating a space where women collaborate—not compete.

5. Community Is the Catalyst for Action

For anyone hesitant to get started, this was their powerful message: Whether you’re a noob (yes, they went there) or a seasoned investor, the encouragement, experience, and wisdom inside this community are what move people from fear to action.

To see what WREIO is all about check out their socials here:

https://www.instagram.com/wreio.oregon/

https://www.facebook.com/groups/wreio/

You can Find Julie and Jaelle here:

https://www.instagram.com/thejaygrouprealestate/

https://thejaygroup.kw.com/?fbclid=PAZXh0bgNhZW0CMTEAAacmmgbN12unP6Vjcdd-UtKdP4o7jEyHdOgxGFxHaz3V_aHQOORrjUTbNldhzQ_aem_kqezhp3irW-vMvPIrwyyjA

Want to learn more about real estate investing? Hop on the waitlist for the Soulful Investor Society, a community membership for real estate investors and those who'd like to get in the game. Once on the waitlist, you'll be the first to know when the doors open AND you'll get lots of amazing freebies, including a FREE 1:1 coaching session with me, where we'll map out your plan from start to finish, so you can finally buy that investment property or grow your portfolio.

This episode is all about helping the next generation-our kids-start building wealth now instead of waiting until "someday."

If you’re a parent, auntie, mentor, or just someone who cares deeply about legacy, this one’s for you. We’re talking about creative ways to get young adults into their first property—even in today’s wild market. Think co-signing, first-time homebuyer programs, seller financing, and real talk about what to do (and not do) when helping your kids invest.

We also cover the not-so-obvious stuff: how to avoid turning a generous gift into a long-term headache, why it pays to model investing instead of just preaching it, and what questions to ask before saying “yes” to buying that condo near campus.

It’s fun, practical, and a little sentimental—in the best way. Let’s talk about planting the seeds of generational wealth, one door at a time. Here are the top takeaways:

1. Get Creative to Help Your Kids Enter the Real Estate Market Early

It’s no secret—homeownership feels out of reach for many young adults. But this episode reminds us that with the right tools (and mindset), parents can help their kids take the first step toward building real estate wealth.

2. Ownership Beats Renting—And It Can Start During College

Why pay rent to someone else when your kid could start building equity instead? Ann shares a case study that reimagines the college rental years as an investment opportunity.

3. Real Estate is a Long Game—Start Early for Compound Gains

Buying early isn’t just about a good deal—it’s about time in the market. Ann explains how compound appreciation and rent growth can outpace the cost of college itself.

4. Seller Financing Is an Underrated Wealth-Building Strategy

Traditional financing doesn’t work for everyone—especially entrepreneurial young adults. Seller financing could open new doors for families willing to think outside the box.

5. Help, Don’t Control: Teach, Model, and Let Them Lead

Helping your kids into homeownership works best when there’s alignment, not pressure. This episode emphasizes modeling wise investing and allowing room for their buy-in.

Want to learn more about real estate investing? Hop on the waitlist for the Soulful Investor Society, a community membership for real estate investors and those who'd like to get in the game. Once on the waitlist, you'll be the first to know when the doors open AND you'll get lots of amazing freebies, including a FREE 1:1 coaching session with me, where we'll map out your plan from start to finish, so you can finally buy that investment property an