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Invest Smarter Podcast

Simon Castillo

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The Invest Smarter is a podcast dedicated to providing insights on how to build wealth and create passive income streams through apartment investing 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 interviews with real estate experts who share their experiences on their journey to financial freedom.
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Invest Smarter

David DeWitt

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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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show series
 
Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Invest 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Episode 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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Invest 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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Episode 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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Episode 210: Taking Massive Action To Achieve Your Goals Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: The importance of taking action, taking calculated risks, and building relationships to help you achieve your goals as a real estate investor. Stepping outside of one’s comfort zone fosters personal …
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Episode 209: Friday Lookback - Housing Inventory Is Up, Buyer's Have More Choices Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The U.S. housing market is shifting towards a balanced state, with neither buyers nor sellers having the upper hand. Increased inventory levels provide buyer…
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Invest Smarter Podcast Episode 208: Flashback Episode - Protecting Your Wealth with Asset Protection Layers Host: Simon Castillo Guest: Brian Bradley Producer: April Munson Simon Castillo is joined by Brian Bradley to discuss: How to protect your wealth What are non-exempt exposed assets? LLCs & asset protection ECCC - Effectiveness, Control, Cost,…
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Episode 207: Friday Lookback - Mailbag Episode: Tips On Turning Apartment Units For New Tenants Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The time to turn an apartment depends on the required work. Underestimating costs can lead to financial strain when unexpected repairs arise. A…
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Episode 173: Flashback Episode - Why Social Media is Crucial for Real Estate Entrepreneurs (and How to Leverage It) Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Tactical tips on how to effectively use social media and why it's important as a real estate investor. Social media in a nutshell is a great…
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Episode 205: Friday Lookback - The Fed's Pivot On Interest Rates Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The Federal Reserve has acknowledged a cooling labor market, which may lead to a reduction in interest rates. Recent increases in unemployment, while historically low, indica…
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Invest Smarter Podcast Episode 204:Flashback Episode - Persevering in Real Estate as a Vietnamese American with Elsa Nguyen Host: Simon Castillo Guest: Elsa Nguyen Simon Castillo is joined by Elsa Nguyen to discuss: The entrepreneurial journey as an immigrant Challenges on the journey of success as an immigrant Real estate is a team sport The value…
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Episode 203: Friday Lookback - What The New NAR Rules Mean for Homebuyers Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The NAR settlement aims to address commission sharing practices that inflate costs and restrict competition. New rules require buyers to sign representation agreemen…
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Invest Smarter Podcast Episode 202: Flashback Episode - Actionable Steps To Start Building Wealth Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Start building generational wealth in 2024 Have your financial house in order Get clear on your spending Create new habits We have open investment opportuniti…
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