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Passive Income Adventures

Passive Income Adventures

Written by: Emma Powell
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 Achieve success through inspiring stories and tough lessons from entrepreneurs and investors. Go behind the scenes in their business deals and passive income adventures. This is a team sport, and every success or mistake has a group of people behind it with stories to learn from. Hosted by Emma Powell of Rise Capital, a commercial real estate investing fund for accredited investors, we'll focus on a variety of passive income topics such as finding and underwriting opportunities, finding a niche, managing business partners, and the teams that make deals happen, all from the trenches!Emma Powell Economics Personal Finance
Episodes
  • 154 - Rocket Science Meets Real Estate - Brian Seidensticker

    154 - Rocket Science Meets Real Estate - Brian Seidensticker
    Jan 13 2026
    Unlocking Wealth Through Tax Sales and Real Estate Investing with Brian Seidensticker of Tax Sale ResourcesWelcome back to another episode of Passive Income Adventures! In this episode, we delve into the world of tax sales and real estate investing with Brian Seidensticker from Tax Sale Resources. Brian shares his journey from aerospace engineering to becoming an expert in the tax sales space and provides valuable insights for both newcomers and seasoned investors. Whether you're Gen X looking to retire early or Gen Z looking to start your investment journey, Brian's expertise covers it all. We also discuss the differences between tax liens and tax deeds, the importance of understanding the capital stack, and the advantages of having the right funding strategies in place. Don't miss this informative and inspiring conversation about turning challenges into opportunities and building wealth through smart investing! Connect with Brian at taxsaleresources.com for more details.Bio:Brian Seidensticker founded Tax Sale Resources (TSR), a comprehensive tax sale data system in 2010. TSR combines three critical aspects of information needed for intelligent investing: Accurate Jurisdiction Information, Upcoming Sale Specifics & Detailed Property Data. They partnered with distressed real estate buyers on 243 properties funding ~$23Million+In September of 2012, Brian partnered to create the Vision Trade Desk, extending services into asset liquidation, allowing tax lien investors to concentrate on their core business of purchasing tax liens on the primary market. In 2017 Brian partnered with software developer SDA Solutions to create Speedboat, a comprehensive workflow management system, redemptive value calculator and document storage platform. In 2020, Brian and his incredible team created Mount North Capital, a fund centered around providing capital access to distressed real estate investors.Connect with Brian:https://taxsaleresources.comConnect with Emma:https://InvestWithEmma.comhttps://Highrise.group00:00 Introduction to Passive Income Adventures00:09 Meet Brian from Tax Sale Resources00:48 Understanding the Audience02:32 Brian's Journey into Tax Sales02:57 The Epiphany and Early Challenges04:27 Discovering Tax Sales07:17 Building Tax Sale Resources10:13 Expanding into Mountain North Capital11:22 Lessons from Misfortune13:38 Finding Your Niche18:52 Current Business Model and Services23:47 Understanding Profit Share Agreements24:52 The Role of Experience in Real Estate Partnerships26:16 Debt vs. Equity: Key Considerations30:16 Exploring Tax Sales and Liens31:45 Tax Liens vs. Tax Deeds: A Detailed Comparison35:57 Opportunities and Risks in Tax Sales40:55 Future Plans and Passive Income Strategies44:52 Final Thoughts and Contact Information
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    48 mins
  • 153 - The Silent Gamble of Floating Rate Debt - Sid Shamim

    153 - The Silent Gamble of Floating Rate Debt - Sid Shamim
    Jan 6 2026
    Unlocking Multifamily Real Estate Success with Sid Shaim | Passive Income AdventuresWelcome back to another episode of Passive Income Adventures! In this episode, I sit down with Sid Shaim from Houston, Texas, founder and head of Headway Capital. Sid shares his extensive experience in multifamily real estate investing and provides insights into the current market opportunities. We discuss our initial meeting, navigating tough times in real estate, and how Sid has repositioned his strategies to thrive in the evolving market. Discover the importance of timing, the role of operations, and why Sid continues to stay passionate about real estate. Tune in to learn from Sid's journey and find out how you can achieve passive income through smart real estate investments.Bio:Before starting Headway Capital, Sid worked as a technology engineer in a Fortune 100 Oil & Gas company, developing and managing more than$100MM worth of technical projects. Sid oversees the company.Is investment strategy and asset management, ensuring projects perform to their greatest potential.Over the past 7 years, Sid has helped hundreds of clients add passive, commercial real estate to their portfolio and diversify from Wall Street.Connect with Sid:Website: https://headwaycapital.usConnect with Emma:Website: https://InvestWithEmma.comWebsite: https://Highrise.group00:00 Introduction and Guest Background01:17 Early Real Estate Ventures and Challenges02:38 Transition to Multifamily Investments03:45 Market Shifts and Strategic Adjustments10:34 Impact of Interest Rate Spikes14:57 Navigating Floating Rate Debt21:14 Introduction to Commodities Trading Background21:21 Understanding Financial Instruments in Multifamily22:31 Importance of Operations in Market Cycles23:45 Investor Education and Limited Partner Insights25:36 Navigating Market Timing and Investment Strategies29:49 The Role of Operations and Team Building34:28 Personal Insights and Career Motivation39:19 Conclusion and Contact Information
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    41 mins
  • 152 - Make Room for Many - Andy Ellwood

    152 - Make Room for Many - Andy Ellwood
    Dec 30 2025
    Unlocking Grocery Savings: The Future of Price Transparency with Andy EllwoodIn this episode of Passive Income Adventures, Emma Powell sits down with Andy Elwood, a seasoned entrepreneur and founder of Stretch. They dive into Andy's unique journey from founding multiple successful startups to creating a groundbreaking app aimed at providing grocery price transparency. Andy shares his riveting story of overcoming challenges and the inspiration behind creating Stretch—a solution to help families save money and time on their grocery shopping. Tune in to learn about the future of grocery shopping, AI integration, and how you can potentially invest in this innovative venture.Bio:Andy Ellwood is the founder and CEO of Stretch, an AI-powered grocery platform reimagining how families navigate the rising cost and complexity of feeding their households. With a career spanning consumer tech, mobility, coaching, and community-building, Andy has a track record of turning everyday problems into empowering solutions.A serial entrepreneur behind companies acquired by Facebook and Google, Andy has helped build products used by millions, launched global learning communities, and led teams dedicated to unlocking human potential. His core philosophy—Make Room For Many—shapes how he builds and leads, using technology as a bridge to expand access, clarity, and opportunity.With Stretch, Andy is tackling one of the most universal challenges Americans face: groceries. By giving families real-time visibility into prices, savings, and smarter choices, he’s building a platform designed to reduce financial stress and return power to everyday consumers.Andy is a passionate home chef, storyteller, and community catalyst. He lives in New York City with his wife, daughter, and rescue dog.Connect with Andy:Website: https://stretchformore.comCareers: https://stretchformore.com/careersConnect with Emma:Website: https://InvestWithEmma.comWebsite: https://Highrise.group00:00 Welcome and Introduction00:43 Meet Andy Elwood: Serial Entrepreneur01:24 The New App: Saving Money on Groceries04:18 Andy Elwood's Journey: From Lawn Mowing to Life Insurance06:50 From Private Jets to Startups09:22 Building and Selling Startups: Go Walla and Waze12:08 The Birth and Fall of Basket.com16:04 The Rebirth: Launching Stretch23:16 Understanding Major Expenses24:10 Grocery Shopping Strategies25:31 Introducing Stretch for More26:17 User Insights and Market Research27:34 The Future of Grocery Shopping28:32 Personal Grocery Shopping Experiences30:45 Stretch for More's Vision and Funding36:16 The Importance of Options in Wealth40:58 Final Thoughts and Future Plans
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    46 mins
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