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REalized Gains Podcast: Daily Summaries Delivered
by Jordan Lee
Realized Gains Podcast is where real estate, investing, and wealth-building strategies come together with real-world experience. Hosted by Portland real estate professionals Steven Tran and Jordan Lee, the show features conversations with investors, industry leaders, and entrepreneurs who are actively building wealth through real estate — from first deals to large portfolios. Whether you’re a new investor trying to get started, a homeowner looking to make smarter financial decisions, or an experienced operator scaling your portfolio, this podcast breaks down the strategies, numbers, mistakes, and mindset behind successful investing. Expect practical insights, honest lessons learned, and actionable advice you can apply immediately. Steven brings an investor-first perspective as an Oregon real estate broker, entrepreneur, and property owner across Oregon and Washington. Jordan adds the financing lens as a mortgage lender licensed in 11 states and an active investor, helping listeners understand how to leverage lending, structure deals, and access capital effectively. If you want to build long-term wealth through real estate — and avoid costly mistakes along the way — you’re in the right place.
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- 3 days ago53 min
Building Wealth Through Cottage Clusters, ADUs & Infill Development | Dustin Miller
What if the backyard of an ordinary Portland home could become your next real estate development opportunity?On this episode of the REalized Gains Podcast, Steven Tran and Jordan Lee sit down with Dustin Miller, a Portland-based real estate investor, builder, and developer who has built his business around finding hidden value in existing properties.Dustin's journey started with a fascination for land development, a real estate license, and a $15,000 wholesale deal that convinced him to quit his job and pursue real estate full-time.After some expensive lessons flipping houses and dealing with contractors, Dustin earned his general contractor license and began building homes himself.Today, he's developing cottage clusters, ADUs, and infill housing throughout Portland, using middle housing land divisions to turn underutilized lots into multiple properties.In this episode, we discuss:🏡 From Wholesaling to Development: How Dustin landed his first $15K deal and transitioned into building new construction.🏗️ Learning Construction the Hard Way: Losing money on contractors, getting his GC license, and learning to manage projects.🏘️ Portland Cottage Clusters & Middle Housing: How zoning changes created new opportunities to build multiple homes on existing residential lots.💰 The Economics of Infill Development: Dustin walks through a project where he purchased a property for approximately $550K, planned four additional homes, and aimed to sell the original house for around $500K.🔨 Finding Hidden Value in Older Homes: Basement conversions, dormers, ADUs, and remodeling strategies that increase usable square footage.📋 Permits, Utilities & Development Costs: What investors need to understand about setbacks, infrastructure, land divisions, and working with Portland's permitting process.🚤 Floating Homes, Marinas & Ebb and Ember: Dustin shares how he expanded beyond traditional housing into floating rentals, marina ownership, and a floating sauna business.🤝 Getting Started in Real Estate Development: Why finding good deals, building relationships, and partnering with experienced developers can open doors for newer investors.Whether you're a real estate investor looking to expand into development, a homeowner curious about building on your property, or an agent wanting to better understand Portland's middle housing opportunities, this episode is packed with practical lessons.Connect with Dustin Miller:Instagram: @dustinvests_Email: dustin@luminent.usConnect with REalized Gains Podcast:Hosted by Steven Tran & Jordan Lee🏡 Steven Tran | Oregon & Washington REALTOR®📱 Call/Text: (971) 285-2002📧 Email: steven@diverserg.com🌐 Website: https://steventranrealestate.com📺 YouTube: https://youtube.com/@steventran_pdxrealtorIf you enjoyed this episode, subscribe to REalized Gains Podcast, hit the like button, and share it with someone interested in real estate investing or development.Drop a comment below: Would you consider developing your own property or building a cottage cluster in Portland?#RealizedGainsPodcast #PortlandRealEstate #RealEstateDevelopment #CottageClusters #RealEstateInvesting Hosted on Acast. See acast.com/privacy for more information.
- Aug 19, 202651 min
50% of Her Real Estate Business Comes From Agent Referrals with Megan Jumago-Simpson
Megan Jumago-Simpson, Principal Broker of Sonder NW at Keller Williams Realty Professionals, joins the REalized Gains Podcast to talk about what it actually takes to build a sustainable, referral-driven real estate business.Megan grew up in the Portland area and was exposed to real estate early through her father, who spent roughly 25 years in the industry. But real estate wasn’t always the plan. After college, Megan lived in China, taught English in Wuhan, spent several years in Shanghai working in events, PR, restaurants and nightlife, and eventually returned home to Portland looking for her next career.What started as helping with her dad’s real estate business eventually turned into building a business of her own.In this episode, Megan talks about the advantages and challenges of becoming a second-generation real estate agent, learning to build an identity separate from her father’s business, and eventually becoming a high-producing solo agent selling roughly 40–50 homes per year.One of the biggest drivers of that growth? Relationships with other real estate agents.Today, Megan estimates that roughly 50% of Sonder NW’s business comes from agent referrals. She breaks down how attending conferences like Keller Williams Family Reunion, building genuine relationships with agents around the country, staying active in referral networks, following up consistently, and delivering a high level of service helped turn those relationships into a major source of business.We also get into the less glamorous side of growth: burnout.After years of being constantly available to clients, Megan reached the point where normal requests to show homes started feeling exhausting. That became a signal that the business needed to change. She shares her experience going from solo agent to building a team, experimenting with leverage, establishing boundaries with clients, and creating systems that allow agents to serve people at a high level without becoming completely dependent on their phones.Megan also explains why she believes your database may be one of the most important assets in your real estate business. After helping more than 500 families, she’s now working through years of contacts and transaction history to create a cleaner, more structured CRM that can support better automation, follow-up and client communication.We also discuss:• Why relationships can outperform traditional lead generation• How Megan built a nationwide real estate referral network• Why follower count doesn’t necessarily equal production• Impressions vs. actual conversions on social media• How personal content helps people build relationships with you• Building systems before scaling a real estate team• Creating boundaries without sacrificing client service• Using AI and automation inside a real estate business• Why clean CRM data becomes more valuable as your business grows• Building community through events and nonprofit work• What Megan looks for when recruiting agents• Why motivation and problem-solving matter more than almost anything else• House hacking with duplexes, triplexes and fourplexes• Using VA, FHA and low-down-payment financing to start investing• Investing for cash flow vs. appreciation• Why property management should be part of your investment analysis• What Megan would tell a brand-new real estate agent todayMegan’s advice for new agents is simple but difficult: organize your database from day one, know exactly where your relationships came from, find a strategy you’re willing to execute consistently, and understand that building a referral-based business takes years—not weeks.You don’t necessarily need millions of views or tens of thousands of followers. You need the right people to know who you are, trust you, and remember you when somebody needs help.Guest: Megan Jumago-SimpsonPrincipal Broker, Sonder NWKeller Williams Realty ProfessionalsWebsite: https://sondernw.comInstagram: https://instagram.com/sonder_nw Hosted on Acast. See acast.com/privacy for more information.
- Jul 8, 20261h 13m
How Alex & Lisa Mont-Ros Built And Sold A Real Estate Business And Pivoted To AI
In this episode of the REalized Gains Podcast, Steven & Jordan sit down with Alex & Lisa Mont-Ros to break down how they built, scaled, and successfully exited a real estate service business—and how they’ve now pivoted into helping professionals leverage AI in their businesses.Lisa shares her journey from bartending to becoming a top-performing real estate agent, eventually identifying a major gap in the industry: the lack of high-quality transaction coordination services. Instead of settling for what was available, they built their own solution—focused on high-level service, communication, and operational efficiency.Alex brings a different perspective, having gone through the 2008 market crash where he lost everything and had to rebuild from scratch. That experience, combined with his time in corporate tech working with enterprise clients, helped shape the operational mindset that allowed their business to scale effectively.Together, they grew their transaction coordination company to over 30 employees, focusing not just on service—but on helping agents actually understand how to run a real business. Their approach went beyond paperwork, emphasizing systems, processes, and scalability—something many agents struggle with.They also break down:What it takes to build a business with the intention of sellingHow valuations and multiples work for service-based companiesWhy most agents fail to operationalize their businessThe biggest mistakes people make when outsourcing too earlyAfter successfully exiting their company, Alex & Lisa transitioned into the AI space, where they now train and consult businesses on how to actually implement AI—not just use it for surface-level tasks.We dive deep into:How AI can automate real estate workflowsWhy most people are using AI wrongHow to think about AI as a “team member,” not just a toolPractical ways to start using AI in your business todayIf you’re a real estate agent, entrepreneur, or business owner looking to scale—or trying to understand how AI is going to impact your industry—this episode is a must-watch.📲 Connect With UsSteven Tran📞 Call / Text: (971) 285-2002📧 Email: steven@diverserg.comJordan Lee📞 Call / Text: +1 (503) 887-3619📧 Email: jordan@jordanleemortgage.com#REalizedGainsPodcast #RealEstateBusiness #Entrepreneurship #AIinRealEstate #BusinessGrowth #ScalingABusiness #RealEstateAgents Hosted on Acast. See acast.com/privacy for more information.
- Jun 17, 202644 min
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 UsSteven Tran📞 Call / Text: (971) 285-2002📧 Email: steven@diverserg.comJordan 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.
- May 27, 20261h 2m
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 UsSteven Tran📞 Call / Text: (971) 285-2002📧 Email: steven@diverserg.comJordan 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.
- May 6, 202648 min
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/thecouchgmWhether 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 UsSteven Tran📞 Call / Text: (971) 285-2002📧 Email: steven@diverserg.comJordan 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.
- Apr 15, 20261h 19m
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 for more information.
- Mar 25, 202652 min
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 for more information.
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About REalized Gains Podcast
Realized Gains Podcast is where real estate, investing, and wealth-building strategies come together with real-world experience. Hosted by Portland real estate professionals Steven Tran and Jordan Lee, the show features conversations with investors, industry leaders, and entrepreneurs who are actively building wealth through real estate — from first deals to large portfolios. Whether you’re a new investor trying to get started, a homeowner looking to make smarter financial decisions, or an experienced operator scaling your portfolio, this podcast breaks down the strategies, numbers, mistakes, and mindset behind successful investing. Expect practical insights, honest lessons learned, and actionable advice you can apply immediately. Steven brings an investor-first perspective as an Oregon real estate broker, entrepreneur, and property owner across Oregon and Washington. Jordan adds the financing lens as a mortgage lender licensed in 11 states and an active investor, helping listeners understand how to leverage lending, structure deals, and access capital effectively. If you want to build long-term wealth through real estate — and avoid costly mistakes along the way — you’re in the right place.
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