If you’re a female real estate investor who feels stuck after your first few deals, this episode is your wake‑up call. This week we're joined by Jesse Dillon, who went from a salon owner to owning 50 rental units in just a few years. Together, we break down why so many women stall out between deals 3–5, why more books and podcasts aren’t your problem, and how trying to do it all alone quietly kills your momentum.

You’ll hear real stories from women inside the WIIRE community who:

• Went from terrified of private money to raising $1.8M in 30 days
• Funded their first flip and BRRRR using private and hard money
• Locked up a competitive 7‑figure deal in an expensive market by learning to move fast

We dive into imposter syndrome, fear of failing publicly, and the identity shift from “I’m trying to invest” to “I am a real estate investor and CEO.”

Tune into Jessie's other WIIRE episodes:

• Episode 22
• Episode 149
• Episode 197

If you’ve been learning nonstop but not taking action, this episode shows why community, accountability, and high‑level rooms are the missing piece for women in real estate.

Resources:

• Simplify how you manage your rentals with TurboTenant
• Get in touch with Envy Investment Group
• Connect with Jessie over on Instagram
• Make sure your name is on the list to secure your spot in The WIIRE Community
• Leave us a review on Apple Podcasts
• Leave us a review on Spotify
• Join our private Facebook Community
• Connect with us on Instagram

This week, we are having an honest and heartfelt conversation about the sacrifices that come with building a life through real estate investing. We reflect on our individual financial journeys and the lifestyle changes we made early on—living below our means, rethinking spending habits, and strengthening our personal financial foundations before taking on larger investments. We share what it looked like during our DIY era, the risks we embraced as entrepreneurs, and the lessons we learned by building something from the ground up. While those seasons required hard choices, they also clarified our values and helped us align our lives with what truly mattered.

We also talk about the rewards that come from those sacrifices and how intentional living has allowed us to create both financial freedom and personal fulfillment. We discuss the motivation that comes from milestones like receiving a first rent payment, the importance of community and surrounding ourselves with like-minded women, and why sacrifice doesn’t have to mean a joyless life. Travel, self-care, and finding joy in small moments remain priorities for us, even as we continue to grow. Ultimately, this episode is a reminder that it’s okay to quit, pivot, and try again—and that with patience, alignment, and support, real estate investing can lead to a life that feels purposeful, balanced, and deeply rewarding.

Resources:

• Simplify how you manage your rentals with TurboTenant
• Get in touch with Envy Investment Group
• Grab our property management checklist
• Make sure your name is on the list to secure your spot in The WIIRE Community
• Leave us a review on Apple Podcasts
• Leave us a review on Spotify
• Join our private Facebook Community
• Connect with us on Instagram

In this episode, we sit down for a year-end audit of our real estate portfolios and have an honest conversation about what’s working, what’s creating stress, and where we need to make changes. We talk about why prioritizing our bookkeeping and truly understanding our numbers is essential to making confident decisions, and how identifying our most stressful properties often reveals deeper issues tied to systems, tenant management, or profitability. By breaking things down property by property, we’re able to evaluate not just financial returns, but also the return on our time and energy.

We also share personal experiences around tenant screening, managing properties more efficiently, and experimenting with different management strategies to find what best supports our goals and lifestyles. Throughout the conversation, we emphasize the importance of regularly reassessing our portfolios, setting clear investment goals for the future, and leaning into community for support, perspective, and shared strategies. This episode is a reminder that successful real estate investing isn’t just about growth—it’s about building a portfolio that feels aligned, sustainable, and empowering.

Resources:

• Simplify how you manage your rentals with TurboTenant
• Get in touch with Envy Investment Group
• Grab your free Property Management Checklist
• Download our free SOP Template
• Make sure your name is on the list to secure your spot in The WIIRE Community
• Leave us a review on Apple Podcasts
• Leave us a review on Spotify
• Join our private Facebook Community
• Connect with us on Instagram

In this episode, real estate CPA Katie Ripp joins us to reveal crucial tax strategies for female real estate investors. Katie debunks persistent myths—like the need for an LLC for more deductions—and explains why understanding depreciation is vital to avoid costly mistakes. She breaks down how to qualify for Real Estate Professional (REP) status and leverage it to offset income, details the “short-term rental loophole” for maximizing Airbnb tax benefits, and simplifies the 1031 exchange for deferring capital gains taxes.

Whether you’re overwhelmed by taxes or seeking proactive strategies, Katie offers clear, practical advice to stay organized and optimize your wealth. Listeners will also learn about the ongoing support and resources available through the WIIRE Community’s quarterly CPA calls, designed specifically for real estate investors. If you’re ready to master the tax game and grow your portfolio with confidence, this episode gives you the knowledge and encouragement you need.

Resources:

• Simplify how you manage your rentals with TurboTenant
• Get in touch with Envy Investment Group
• Connect with Katie
• Make sure your name is on the list to secure your spot in The WIIRE Community
• Leave us a review on Apple Podcasts
• Leave us a review on Spotify
• Join our private Facebook Community
• Connect with us on Instagram

Struggling to rent out your property despite your best efforts? You’re not alone, and this episode is your essential guide to overcoming stubborn vacancies. Drawing on real stories and expert strategies from the women-focused WIIRE Community, we break down practical steps to get your property moving fast:

• Diagnose rental issues and know when to pivot strategies
• Attract and keep tenants with creative incentives, ethical landlording, and effective listing audits
• Learn why compassion and professionalism deliver returns—and stronger communities
• Decide when to convert, upgrade, or even sell your property
• Understand the importance of financial reserves and ongoing support

We share personal experiences and those of female investors to explore how a collaborative approach fosters wealth and enhances neighborhoods. Additionally, access our free property management checklist and discover why you should join the WIIRE Community for valuable ideas, resources, and genuine support. Tune in and turn your challenges into new opportunities with the collective power of women in real estate.

Resources:

• Simplify how you manage your rentals with TurboTenant
• Get in touch with Envy Investment Group
• Grab our property management checklist
• Make sure your name is on the list to secure your spot in The WIIRE Community
• Leave us a review on Apple Podcasts
• Leave us a review on Spotify
• Join our private Facebook Community
• Connect with us on Instagram

In this episode, we demystify tax season for female real estate investors, proving it doesn’t have to be stressful or last-minute. Drawing on our personal experiences, we share practical systems for year-round organization, from mastering 1099 and W-9 requirements to distinguishing between capital expenditures (CapEx) and repairs for smarter tax benefits.

We also highlight the value of digital bookkeeping tools, such as QuickBooks, and discuss the advantages of hiring a real estate-specific bookkeeper. Additionally, we detail the importance of preparing quarterly estimated tax payments to avoid penalties. The conversation covers setting up digital filing systems for receipts and closing statements, maintaining a Properties Quick Guide, and diligent record-keeping for those pursuing Real Estate Professional Status (REPS).

You will learn actionable steps to streamline processes, maximize deductions, and work effectively with CPAs. Packed with community resources and honest advice, this episode provides empowering strategies to help you face tax time with confidence and focus on building your real estate success.

Resources:

• Simplify how you manage your rentals with TurboTenant
• Get in touch with Envy Investment Group
• Get the deets on working with the WIIRE Bookkeeper
• Make sure your name is on the list to secure your spot in The WIIRE Community
• Leave us a review on Apple Podcasts
• Leave us a review on Spotify
• Join our private Facebook Community
• Connect with us on Instagram

In this episode, we explore a five-step turnover system designed to help female real estate investors streamline rental transitions, making them smooth, fast, and profitable. Drawing from personal experience and expert insights, we explain how effective documentation—from appliance details to paint colors—streamlines turnovers and cuts costs. We emphasize clear tenant communication regarding lease terms, notices, and fees, and highlight the value of systems such as pre-move-out walkthroughs, timely advertising, and professional cleaning.

You'll hear real-life anecdotes, tips for automating communication and delegating tasks, and learn the power of using checklists and SOP templates to stay organized—even as a solo manager. Grab our free property management checklist and get your name on the list to be the first to know when doors open to the WIIRE Community! This episode offers practical advice and encouragement to help you minimize vacancies, maximize cash flow, and confidently grow your rental business.

Resources:

• Simplify how you manage your rentals with TurboTenant
• Get in touch with Envy Investment Group
• Grab our freebie for self-managing your rentals
• Make sure your name is on the list to secure your spot in The WIIRE Community
• Leave us a review on Apple Podcasts
• Leave us a review on Spotify
• Join our private Facebook Community
• Connect with us on Instagram

In this episode, we open up about the creative strategies we've discovered as female real estate investors to secure capital when traditional funding feels out of reach. We share our experiences with tapping into equity, refinancing, and leveraging our networks, along with creative financing options like seller financing and partnerships. Throughout our journey, we've learned the importance of community, due diligence, and strategic planning.

We've found that accessing our own equity through refinancing or HELOCs and building strong networks has been key to uncovering creative financing options. Understanding return on equity (ROE) has helped us evaluate property performance, and partnerships have provided us with capital, though they require careful due diligence.

Raising private money and exploring creative financing methods like seller financing have been game-changers for us, bridging funding gaps when needed. We've realized that community support is invaluable for sharing resources and advice, and regularly reviewing our portfolio's equity is crucial for strategic planning. These approaches have empowered us to make informed decisions and grow our investments with confidence.

Resources:

• Grab your seat for our webinar on November 17th
• Check out Episode 197
• Simplify how you manage your rentals with TurboTenant
• Get in touch with Envy Investment Group
• Make sure your name is on the list to secure your spot in The WIIRE Community
• Leave us a review on Apple Podcasts
• Leave us a review on Spotify
• Join our private Facebook Community
• Connect with us on Instagram