The Invest Smarter is a podcast dedicated to providing insights on how to build wealth and create passive income streams through real estate investing, business and entrepreneurship so that you too can become a smarter investor. Released weekly on Tuesdays and Fridays, The Invest Smarter Podcast is hosted by Simon Castillo. The show will feature commentary and interviews with real estate experts who share their experiences on their journey to financial freedom.
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Helping results-driven individuals make results-driven financial decisions in order to build and preserve lasting wealth so you can spend more time doing what you love, and stress less about money. All content within the podcast is for informational purposes only and should not be relied upon for investment decision-making.
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ISP 260: Five Ways You Can Find Off Market Deals
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14:19Episode 260: Five Ways You Can Find Off Market Deals Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Effective methods for uncovering off-market opportunities The Role of Networking in Real Estate Building a strong network in real estate can lead to exclusive deal opportunities. The necessity of develop…
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ISP 259: Friday Look Back - Unlocking The Power of Off Market Deals
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13:33Episode 259: Friday Look Back - Unlocking The Power of Off Market Deals Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: What are off market deals and how can you find them? The Importance of Seller Relationships Tailoring communications to specific demographics, like absentee owners or …
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Episode 258: Why Are Mortgage Rates Falling? Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: The direction that mortgage rates are headed. The Relationship Between Mortgage Rates and Treasury Yields Investor Sentiment Amid Economic Concerns Impact of Declining Consumer Spending Opportunities in Real Est…
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ISP 257: Friday Look Back -What's Your Personal Investment Strategy?
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10:53Episode 257: Friday Look Back -What's Your Personal Investment Strategy? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Choosing your personal investment strategy. Your investment strategy should be customized to meet your individual needs. How can you design a strategy that works for …
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ISP 256: Finding Hidden Multifamily Opportunities with Andrea Foley
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56:08Episode 256: Finding Hidden Multifamily Opportunities with Andrea Foley Host: Simon Castillo Guest: Andrea Foley Join our host Simon Castillo with Andrea Foley episode as they reflects on: Buying hotels and converting to multifamily Solutions for affordable housing We have open investment opportunities. Want to learn more? Check out www.sastexascap…
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ISP 255: Friday Look Back - Mailbag: Long & Short Term Investing Strategies
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10:58Episode 255: Friday Look Back - Mailbag: Long & Short Term Investing Strategies Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The differences between buy and hold investing and buy and hold turnkey properties. The distinction between active and passive real estate investing strategies…
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ISP 254: Proven Leasing Strategies For When Your Property Won't Rent
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13:39Episode 254: Proven Leasing Strategies For When Your Property Won't Rent Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Ensuring properties are rent-ready with great curb appeal is crucial for attracting tenants. Conducting detailed market analyses helps in setting competitive rental prices and underst…
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ISP 253: Friday Look Back - 5 Tips For Beginning Investors
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12:32Episode 253: Friday Look Back - 5 Tips For Beginning Investors Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Having a growth mindset. Picking a strategy that fits your goals. You have to take action and learn from experience. Have a trusted coach and mentor. You have to build the righ…
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ISP 252: Have You Considered Building Vs Buying?
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12:19Episode 252: Have You Considered Building Vs Buying? Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Is it better to buy or build property right now? There is a larger profit potential when you engage in ground-up development. You'll never know what you are going to find after buying a property. Be awar…
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ISP 251: Friday Look Back - The Biggest Barrier to Getting Started: Fear!
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11:30Episode 251: Friday Look Back - The Biggest Barrier to Getting Started: Fear! Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Fear of the Unknown The journey often begins with small, manageable investments, such as buying a duplex or a single-family home. While self-learning is valuable…
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ISP 250: Having a Coach or Mentor Alongside You
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37:43Episode 250: Having a Coach or Mentor Alongside You Host: Simon Castillo Guests: Brian Head & Chris Gordon Join our host Simon Castillo with Brian Head & Chris Gordon as they discuss on: The value of education, coaching, and having the right mindset. What makes real estate investors successful. How do you overcome the sense of being overwhelmed and…
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ISP 249: Friday Look Back - Why Real Estate Investing?
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10:34Episode 249: Friday Look Back - Why Real Estate Investing? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Why do we invest in real estate? What is your motivation for wanting to invest in real estate? What are you investing in real estate? Real estate offers a path to financial freedom…
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ISP 248: Investment Advice with Yonah Weiss
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38:48Episode 248: Investment Advice with Yonah Weiss Host: Simon Castillo Guest: Yonah Weiss Join our host Simon Castillo for a one on one episode as he reflects on: Abundance Mindset Cost Segregation Bonus Depreciation Passive Investing Overcoming limiting beliefs Stick with your principles We have open investment opportunities. Want to learn more? Che…
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ISP 247: Friday Look Back - Invest Confidently!
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7:32Episode 247: Friday Look Back - Invest Confidently! Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Understanding fear is crucial for real estate investing success. Knowledge reduces fear and boosts confidence in decision-making. Smart investors manage, not eliminate, risk. Setbacks in …
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ISP 246: Overcoming Analysis Paralysis and Taking Action
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22:18Episode 246: Overcoming Analysis Paralysis and Taking Action Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Analysis Paralysis Ready - aim aim aim aim aim – are you taking a shot? Sometimes it takes a while to gain momentum Be sure not to take advice from the wrong individuals Your business doesn’t hav…
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ISP 245: Friday Look Back - Are You Ever Too Old To Invest In Real Estate?
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10:20Episode 245: Friday Look Back - Are You Ever Too Old To Invest In Real Estate? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Age might bring different challenges, but it also offers some unique opportunities. Discipline; focus on the manageable and low risk deals that are aligned with…
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ISP 244: Remote Real Estate Investing Strategies with Jen & Stacy Conkey
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50:24Episode 244: Remote Real Estate Investing Strategies with Jen & Stacy Conkey Host: Simon Castillo Join our host Simon Castillo with Jen & Stacy Conkey as they discuss on: “Real Estate is that thing that I want to do.” What is a joint venture and how do you structure that project? I lost $80,000 in one single day Don’t go that fast, stay with your f…
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ISP 243: Friday Lookback - Overcoming Imposter Syndrome
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9:08Episode 243: Friday Look Back - Overcoming Imposter Syndrome Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: What exactly is imposter syndrome? Numbers and comparison are one of the unique challenges in real estate. Embracing the discomfort and using it as fuel to grow. Instead of tryin…
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ISP 242: What to Know About Cash Flow As An Investor
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12:33Episode 242: What to Know About Cash Flow As An Investor Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Misconception about cash flow. How you can proactively protect your investment. How you can optimize and protect your cash flow. Maintaining cash flow and having a cash reserve are essential for a re…
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ISP 241: Friday Look Back - Is Flipping Properties The Right Strategy For You?
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10:20Episode 241: Friday Look Back - Is Flipping Properties The Right Strategy For You? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Is flipping properties the right path for you? Flipping is most effective when several key factors are aligned. Flipping is more like running a manufacturin…
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ISP 240: Top Real Estate Trends to Watch For in 2025
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10:05Episode 240: Top Real Estate Trends to Watch For in 2025 Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Emerging trends for real estate investors The Federal Reserve’s approach to interest rates is tied closely to inflation indicators, and while rate cuts may occur, they will depend on the inflation tr…
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ISP 239: Friday Look Back - Building a Vertically Integrated Real Estate Business
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50:51Episode 239: Friday Look Back - Friday Look Back - Building a Vertically Integrated Real Estate Business Host: Simon Castillo Guest: Mark Updegraff Join our host Simon Castillo with Mark Updegraff as they discuss: How to know when to pivot in your career Building a business Finding people that you resonate with and asking questions Joining a master…
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ISP 238: The Surprising Lucrative Real Estate Asset Class with Stewart Heath
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44:28Episode 238: The Surprising Lucrative Real Estate Asset Class with Stewart Heath Host: Simon Castillo Guest: Stewart Heath Join our host Simon Castillo with Caleb Johnson as they discuss: Real estate is a constant in our lives Outlook for office real estate The Debt Wall Rate cuts Multifamily Meltdown Opportunities in multifamily to come The Tennes…
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ISP 237: Friday Look Back - Looking back at 2024, Looking Forward to 2025
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13:32Episode 237: Friday Look Back - Looking back at 2024, Looking Forward to 2025 Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Starting doesn't mean you have to know everything or that you have to have all the answers, it means committing to the journey. Taking the first step no matter h…
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ISP 236: Friday Look Back - Strategies vs Tactics For Real Estate Investors
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10:22Episode 236: Friday Look Back - Friday Look Back - Strategies vs Tactics For Real Estate Investors Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: What it takes to understand the difference between having a strategy and a tactic. Strategy is your big-picture plan. Tactics behind the str…
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ISP 235: How Can The Busy W2 Professional Get Started In Real Estate?
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41:57Episode 235: How Can The Busy W2 Professional Get Started In Real Estate? Host: Simon Castillo Guest: Dan Calonge Join our host Simon Castillo with Caleb Johnson as they discuss: Multifamily is a team sport Balancing a W2 with being an investor Giving back The importance of aligning values We have open investment opportunities. Want to learn more? …
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ISP 234: Friday Look Back - Mailbag Episode: Should You Buy A Cheap Property?
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11:32Episode 234: Friday Look Back - Mailbag Episode: Should You Buy A Cheap Property? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Knowing your market is crucial. Properties deemed “cheap” can lead to poor investment outcomes if they lack demand. Always analyze local trends. Investing in…
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ISP 233: Overcoming Limiting Beliefs and Taking Action to Achieve Your Goals
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37:08Episode 232: Overcoming Limiting Beliefs and Taking Action to Achieve Your Goals Host: Simon Castillo Guest: Caleb Johnson Join our host Simon Castillo with Caleb Johnson as they discuss: Family Hardships House Hacking Setting goals that stretch you, but are still realistic Taking action If you’re a passive investor, be okay with walking away from …
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ISP 232: Friday Look Back - Traits Successful Real Estate Investors Have In Common
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15:31Episode 232: Friday Look Back - Traits Successful Real Estate Investors Have In Common Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The common traits that set successful real estate investors apart from the people that dabble. Overcoming analysis paralysis is crucial; taking the firs…
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ISP 231: From Being in Debt to Building Wealth with Tim Little
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46:01Episode 231: From Being in Debt to Building Wealth with Tim Little Host: Simon Castillo Guest: Tim Little Join our host Simon Castillo for a one on one episode as he reflects on: Tenant experiences Structuring the 1031 Exchange Tax strategies Overcoming student debt and growing financially as an investor Building up a network and reputation as an o…
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ISP 230: Friday Look Back - Black Friday: Strategies That Can Help Grow Your Real Estate Portfolio
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9:31Episode 230: Friday Look Back - Black Friday: Strategies That Can Help Grow Your Real Estate Portfolio Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Growing a real estate portfolio requires strategic planning and goal-setting, especially at the year’s end. Utilizing 1031 exchanges can…
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ISP 229: Beyond Borders: Jonathan Wei's Path to Real Estate Syndication
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36:06Episode 229: Beyond Borders: Jonathan Wei's Path to Real Estate Syndication Host: Simon Castillo Guests: Jonathan Wei Join our host Simon Castillo with Jonathan Wei as they discuss: Life is so much more than making money What is life and why am I here? Mindset and spirituality Could you have made it without a mentor? Self storage deals We have open…
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ISP 228: Friday Look Back - The Compounding Effects of Small Wins In Real Estate Investing
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12:14Episode 228: Friday Look Back - The Compounding Effects of Small Wins In Real Estate Investing Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Small wins, while seemingly insignificant, compound over time, leading to greater motivation and confidence. The Importance of Actionable Goals …
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ISP 227: Having a Coach or Mentor Alongside You
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37:43Episode 227: Having a Coach or Mentor Alongside You Host: Simon Castillo Guests: Brian Head & Chris Gordon Join our host Simon Castillo with Brian Head & Chris Gordon as they discuss on: The value of education, coaching, and having the right mindset. What makes real estate investors successful. How do you overcome the sense of being overwhelmed and…
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ISP 226: Friday Look Back - Fix & Flips vs Passive Real Estate Investing: Which Is Right For You?
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11:28Episode 226: Friday Look Back - Fix & Flips vs Passive Real Estate Investing: Which Is Right For You? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Regardless of which investment strategy you choose, the bottom line is - you have to take action Time commitment and how actively involve…
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ISP 225: Finding a Niche in Self Storage
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46:33Episode 225: Finding a Niche in Self Storage Host: Simon Castillo Guest: Russell Nersesov Join our host Simon Castillo with Russell Nersesov as they discuss on: It takes a village to work on a multifamily project Is there a huge difference between the financials, economics, and returns that investors see in self storage compared to multifamily? How…
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ISP 224: Friday Look Back - How Will Trump Influence Your Investments?
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9:10Episode 224: Friday Look Back - How Will Trump Influence Your Investments? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The potential tax benefits for real estate investors under Trump’s new term. Fewer regulatory hurdles and faster approval times for permits and zoning changes could…
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ISP 223: How Can The Busy W2 Professional Get Started In Real Estate?
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40:29Episode 223: How Can The Busy W2 Professional Get Started In Real Estate? Host: Simon Castillo Guest: Dan Calonge Join our host Simon Castillo with Dan Calonge as they discuss on: Multifamily is a team sport Balancing a W2 with being an investor Giving back The importance of aligning values We have open investment opportunities. Want to learn more?…
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ISP 222: Friday Look Back - 3 Reasons Real Estate Outperforms Stocks
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12:42Invest Smarter Podcast Episode 222: Friday Look Back - 3 Reasons Real Estate Outperforms Stocks Host: Simon Castillo Producer: April Munson Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: “Why invest in real estate when you can invest in the stock market?” Tax benefits written into the Tax Code Investing in real…
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ISP 221: The Power of Having One Rental Property
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12:28Episode 221: The Power of Having One Rental Property Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Proven strategies,tactics, and the right mindset to build highly profitable and successful real estate investing. The power of building wealth even if you just own one rental property. Real estate is an …
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ISP 220: Friday Look Back - Are You Making Things Happen?
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11:28Episode 220: Friday Look Back - Are You Making Things Happen? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The Keys to shifting from a defensive to an offensive way in life. It comes down to taking control, making sacrifices, focusing on what's important, and pushing through the hard…
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ISP 219: Understanding What Renovations You Need To Make
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12:49Episode 219: Understanding What Renovations You Need To Make Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: How to determine the necessary repairs for an investment property? Hire professionals who have more expertise than you in areas where you lack expertise. Remember to ask plenty of questions. The …
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ISP 218: Friday Look Back - Mailbag Episode: I Want to Start Flipping Properties
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9:42Episode 218: Friday Look Back - Mailbag Episode: I Want to Start Flipping Properties Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Proven strategies, tactics, and the right mindset are essential for building a highly profitable and successful real estate investing business. Real estat…
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ISP 217: Friday Look Back - Momentum: How Do You Create It & How Do You Sustain It?
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10:26Episode 217: Friday Lookback - Momentum: How Do You Create It & How Do You Sustain It? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: How can you find momentum? What does it feel like to have momentum? We have open investment opportunities. Want to learn more? Check out www.sastexascap…
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ISP 216: Finding Your Focus: Real Estate Investing For Beginners
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12:28Episode 216: Finding Your Focus: Real Estate Investing For Beginners Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Exploring your focus. Three questions to ask yourself; Do you need real estate as a job or as an investment?, Do you want to be an active or passive investor?, and Where are you on your w…
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ISP 215: Friday Lookback - Don't Fall For These Misconceptions About Falling Interest Rates For Real
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9:36Episode 215: Friday Lookback - Don't Fall For These Misconceptions About Falling Interest Rates For Real Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Mortgage Payment Misconception Falling interest rates often reflect economic slowdown rather than growth, which can be detrimental for…
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ISP 214: Building Wealth With Boring Properties
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11:50Episode 214: Building Wealth With Boring Properties Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Boring properties can build wealth. Substantial down payments (20-40%) ensure cash flow. With properties appreciating, investors can refinance or pull equity when interest rates drop, allowing for further…
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ISP 213: Friday Lookback - Avoiding Roofing Scammers
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9:11Episode 213: Friday Lookback - Avoiding Roofing Scammers Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The dangerous issue of roof repair scams that often target homeowners and real estate investors, especially after severe weather events. How scammers operate—offering free inspection…
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ISP 212: Flashback Episode - Building Wealth With Customizable Funds Featuring Jeff Greenberg
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41:56Invest Smarter Podcast Episode 212: Flashback Episode - Building Wealth With Customizable Funds Featuring Jeff Greenberg Host: Simon Castillo Guest: Jeff Greenberg Producer: April Munson Simon Castillo is joined by Jeff Greenberg to discuss: Running a business alongside the right team Opportunities present themselves often when people are not looki…
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ISP 211: Friday Lookback - What The Fed Did and Didn't Say About The Rate Cut
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9:47Episode 211: Friday Lookback - What The Fed Did and Didn't Say About The Rate Cut Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The Fed’s interest rate cut is a proactive measure aimed at stabilizing the economy. While it may not immediately lower borrowing costs for real estate inves…
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