From Air Force Veteran To Oregon REALTORS President with Dr. Tony Kelly

How Jaina Anne Built 10 Rental Units And Invests In Hotels While Working A W2

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. 📲 CONNECT WITH US 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 [https://acast.com/privacy] for more information.

How Two Sisters Built A Portland Boutique From A Basement To A Brick And Mortar Store

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. 📲 CONNECT WITH US 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 [https://acast.com/privacy] for more information.

Building A Baseball YouTube Channel That Actually Makes Money While Doing Mortgages with Connor Webb

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 [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. 📲 CONNECT WITH US 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 [https://acast.com/privacy] for more information.

From Air Force Veteran To Oregon REALTORS President with Dr. Tony Kelly

Dr. Tony Kelly joins Steven Tran and Jordan Lee for a wide-ranging conversation on leadership, real estate, and what it really means to “give back” after building a successful career. Tony’s story spans Detroit → the Air Force Academy → serving as a nuclear launch officer → corporate sales/ops leadership with heavy travel → and eventually taking the leap into real estate with a business plan, a SWOT analysis, and a relentless commitment to execution. We dig into the fundamentals that helped him win early in real estate—branding before Zillow, nonstop open houses, postcards/mailers, and even advertising other agents’ listings to build perceived credibility. Tony shares how those systems-thinking habits (checklists, process discipline, time blocking) translated from the military and corporate life into a repeatable client experience and long-term business growth. That path ultimately led him to Keller Williams ownership, where he helped start KW Portland Premiere and has remained deeply invested in building people and platforms. From there, the conversation shifts to governance and advocacy: why Oregon REALTORS® leadership matters, how policy and legislation quietly shape our industry, and why protecting pillars like the 30-year mortgage and mortgage interest deduction is a constant fight—often invisible to producers focused only on transactions. Tony also explains how he got pulled into leadership at PMAR (Portland Metropolitan Association of Realtors), then into statewide roles, including serving as Oregon REALTORS® President (2025 and 2026) and participating in a major governance restructure—the biggest at the state level since the early 1980s. We also go personal: his doctorate journey (and why it’s one of the hardest grinds you can take on), becoming an adjunct professor, and his dissertation research on the “secret sauce” behind African-American women who make partner at top corporate law firms. Plus—burnout, balance, hobbies, and how a 20-year daily running streak and trail races keep him centered while he travels, leads, and still serves clients. If you’re a Realtor, team leader, broker-owner, or aspiring association leader, this episode is a masterclass in long-game thinking: build systems, invest in people, protect the industry, and find a mission bigger than production. #OregonRealtors #PMAR #RealEstateLeadership #RealEstateAdvocacy #MortgageRates #HousingPolicy #GenerationalWealth #KellerWilliams #PortlandRealEstate #OregonRealEstate #RealtorLife #RealEstateBusiness #LeadershipDevelopment #TimeBlocking #SystemsThinking #RealEstatePodcast #DiversityInRealEstate #NAR #30YearMortgage ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

From Acting To Mortgages To Building A Real Estate Content Business with Michael Hudson

Michael Hudson of Praised Media joins the REalized Gains Podcast to break down what actually works for real estate content in 2026: how to choose the right content goals (leads vs. viral vs. brand), how to define your ideal avatar, and how to create educational + lifestyle content that converts without feeling “salesy.” We talk through Michael’s path from acting in LA to commercial mortgage brokering, then building a real estate-first media company serving Seattle, Portland, Vancouver, WA (and even Arizona). We get tactical on batching shoots, filming with just a phone, building repeatable systems (scripts, research, editing workflows), and hiring for character + communication. Michael also shares his POV on SEO for YouTube (titles, descriptions, using transcripts), why he prefers running Meta ads vs. boosting posts, and how consistent DM + comment responses turn views into real conversations and clients. If you’re a realtor, lender, investor, or service pro trying to grow with content—this episode is a roadmap for creating videos that build trust, show social proof, and generate inbound leads over time. #RealEstateMarketing #ContentCreation #VideoMarketing #YouTubeSEO #InstagramReels #SocialMediaMarketing #PersonalBranding #RealtorTips #MortgageMarketing #PortlandRealEstate #VancouverWA #SeattleRealEstate #Entrepreneurship #BatchContent #ContentStrategy ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.