In this episode of the REalized Gains Podcast, Steven & Jordan sit down with Jaina Anne, a real estate investor based in Orange County who has built a 10-unit rental portfolio—all while maintaining a full-time W2 in public health.

Jaina shares how she got started in real estate during COVID after realizing a gap in her financial literacy. What began with a single out-of-state investment turned into scaling a portfolio of long-term rentals in the Midwest, leveraging creative financing strategies and relationships with local lenders.

We dive into how she was able to grow quickly without using large amounts of her own capital, including using commercial loan products, refinancing strategies, and building systems to manage properties remotely. She also breaks down the realities of investing in lower-cost markets—covering both the upside (cash flow, low entry price) and the downside (CapEx, market risks, and long-term appreciation).

The conversation also explores her experience investing as a limited partner in boutique hotel developments, how syndications work, and why she chose branding and relationships over purely analyzing numbers when making investment decisions.

Jaina also shares her unique approach to travel hacking, showing how real estate investors can leverage everyday expenses to generate points and take luxury trips—sometimes worth tens of thousands of dollars annually.

Finally, we discuss why she continues to keep her W2, how she balances multiple income streams, and her advice for anyone looking to get started in real estate today.

Whether you’re just getting started or looking to scale your portfolio, this episode is packed with practical strategies and a refreshing perspective on building wealth without quitting your job.

Steven Tran

📞 Call / Text: (971) 285-2002

📧 Email: steven@diverserg.com

Jordan Lee

📞 Call / Text: +1 (503) 887-3619

📧 Email: jordan@jordanleemortgage.com

#REalizedGainsPodcast #RealEstateInvesting #RentalProperties #PassiveIncome #Syndications #TravelHacking #RealEstatePodcast

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the REalized Gains Podcast, Steven & Jordan sit down with the sister duo behind Lady Mae Boutique, Sharon and Donna, to talk about how they built a retail business in Portland starting from a basement during the pandemic.

Sharon and Donna share their journey from Honolulu to Portland, their backgrounds in nonprofit work and fashion design, and how burnout from corporate roles pushed them to take a leap into entrepreneurship. What started as a small operation selling clothes out of a basement quickly evolved into pop-ups, markets, and eventually a brick-and-mortar boutique on Alberta Street.

They break down the realities of running a retail business—from signing leases and managing inventory to navigating slow seasons, inconsistent income, and the importance of community support. The conversation dives into what actually drives customer loyalty, why in-person retail still matters, and how creating a personalized shopping experience sets them apart in a world dominated by online shopping.

Sharon and Donna also share lessons on marketing, building a brand without paid ads, and why word-of-mouth and relationships have been their biggest drivers of growth. They talk candidly about the risks of entrepreneurship, working with family, and what it really takes to build something sustainable.

If you’ve ever thought about starting your own business, opening a retail store, or building a brand from scratch, this episode is packed with real-world insight you won’t want to miss.

Steven Tran

📞 Call / Text: (971) 285-2002

📧 Email: steven@diverserg.com

Jordan Lee

📞 Call / Text: +1 (503) 887-3619

📧 Email: jordan@jordanleemortgage.com

#REalizedGainsPodcast #PortlandSmallBusiness #BoutiqueOwner #WomenInBusiness #Entrepreneurship #RetailBusiness #PortlandOregon

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the REalized Gains Podcast, Steven & Jordan sit down with Connor Webb, a mortgage lender in the Portland–Vancouver market who has built a growing YouTube channel centered around baseball, content creation, and long-term brand building.

Connor shares how he got started in the mortgage industry right out of college and how his passion for sports led him to launch a YouTube channel that has grown into a real business asset. What started as baseball content evolved into a platform that generates opportunities, brand partnerships, and even mortgage clients.

We dive into how Connor approaches YouTube strategically, including how he thinks about thumbnails, titles, retention, and monetization. He breaks down the difference between evergreen vs. trending content, why consistency matters more than perfection, and how he repurposes long-form videos into short-form content across platforms.

Connor also shares behind-the-scenes insight into building a channel from scratch, getting media access with professional sports teams, and how he’s leveraged content to close real deals and grow his business.

👉 Check out Connor’s YouTube channel here:

https://www.youtube.com/thecouchgm

Whether you’re a real estate agent, lender, or entrepreneur looking to build your brand through content, this episode is packed with actionable insight you can apply immediately.

Steven Tran

📞 Call / Text: (971) 285-2002

📧 Email: steven@diverserg.com

Jordan Lee

📞 Call / Text: +1 (503) 887-3619

📧 Email: jordan@jordanleemortgage.com

#REalizedGainsPodcast #YouTubeForRealEstate #ContentCreation #BaseballYouTube #MortgageLender #PersonalBrand #RealEstateMarketing

Hosted on Acast. See acast.com/privacy for more information.