Simon Castillo
Invest Smarter Podcast
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.
Author
Simon Castillo
Category
Podcast website
Latest episode
Jul 7, 2026
Where to listen?
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Episodes
ISP 272: Friday Look Back - Do This to Find Your Next Deal 16.05.2025 9:53
Episode 272: Friday Look Back - Do This to Find Your Next Deal Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The impact of economic uncertainty on real estate investment strategies. How rising tariffs are influencing investor decisions and market behavior. Shifts in buyer sentiment and what they mean for property values. Key takeaw...
ISP 271: Creating The Path To Becoming A Real Estate Syndictor 14.05.2025 38:28
Episode 271: Creating The Path To Becoming A Real Estate Syndictor Host: Simon Castillo Guest: Jim Lee Simon Castillo is joined by Jim Lee to discuss: Building a real estate portfolio What is multifamily syndication and why should people invest in it? Achieving your dreams through multifamily investments Investing in yourself through education Networking is key to success in the real estate...
ISP 270: Friday Look Back - Fed Pauses on Rates Again; What it Means 09.05.2025 10:33
Episode 270: Friday Look Back - Fed Pauses on Rates Again; What it Means Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The latest developments in economic uncertainty and what they mean for investors. The lingering impact of tariffs and international trade dynamics. How real estate professionals are adapting to shifting market sign...
ISP 269: The Mistake Beginning Investors Should Avoid 07.05.2025 8:39
Episode 269: The Mistake Beginning Investors Should Avoid Host: Simon Castillo Join our host Simon Castillo for a one-on-one episode as he reflects on: Navigating uncertainty in today’s real estate market. How rising tariffs impact investor confidence. Key strategies to stay resilient during economic shifts. Lessons learned from past market cycles. We have open investment opportunities. Want to l...
ISP 268: Friday Look Back - 5 Ways Your Rental is Leaking Cash 02.05.2025 11:20
Episode 268: Friday Look Back - 5 Ways Your Rental is Leaking Cash Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The five silent ways your rental property might be leaking cash — and how to fix them. What turns a once-promising asset into an “alligator property” devouring your profits. Real-world lessons from the week’s challenges...
ISP 267: Signs Your Contractor May Be Going Under 29.04.2025 8:27
Episode 267: Signs Your Contractor May Be Going Under Host: Simon Castillo Join our host Simon Castillo for a one-on-one episode as he reflects on: How shifting economic tides and uncertainty are shaping investor sentiment The real impact of tariffs on global markets and local business decisions Navigating fear, risk, and opportunity in today’s real estate landscape Why staying adaptable is more...
ISP 266: Friday Look Back - Slower Is Faster in Real Estate Investing 25.04.2025 11:28
Episode 266: Friday Look Back - Slower Is Faster 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: Why moving slower in real estate can actually lead to faster, more sustainable success How the "tortoise vs. hare" mindset applies to building long-term wealth The power of compounding through steady por...
ISP 265: Take Decisive Action to Overcome Analysis Paralysis 22.04.2025 10:17
Episode 265: Take Decisive Action to Overcome Analysis Paralysis Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Understanding Analysis Paralysis The Power of Mindset The Offer as a Starting Point Strategic Pessimism Embracing Failure as Data We have open investment opportunities. Want to learn more? Check out www.sastexascapital.com Download our F...
ISP 264: Friday Look Back - Economic Uncertainty, Tariffs and Real Estate Investors 18.04.2025 9:17
Episode 264: Friday Look Back - Economic Uncertainty, Tariffs and Real Estate Investors Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Tariffs Are Spiking Costs – Steel, lumber, and key materials are up 15–20% overnight. Delays & Vacancies Rising – Supply chain hiccups and hesitant buyers are slowing the market. Smart Investors...
ISP 263: How to Start Raising Capital 15.04.2025 12:08
Episode 263: How to Start Raising Capital Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Discover a powerful shift in how investors approach opportunities. Learn why mindset may be the biggest obstacle to growth. Uncover the often-overlooked skill that separates average from exceptional. Explore how long-term success is built on more than just num...
ISP 262: Friday Look Back - Fear Causes Paralysis 04.04.2025 10:18
Episode 262: Friday Look Back - Fear Causes Paralysis Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The gap between what property sellers believe their properties are worth and what buyers can realistically pay is growing. The Federal Reserve’s ongoing increases in interest rates pose challenges for multifamily investors. Current e...
ISP 261: Building a Vertically Integrated Real Estate Business 01.04.2025 50:51
Episode 261: Building a Vertically Integrated Real Estate Business Host: Simon Castillo Guest: Mark Updegraff Join our host Simon Castillo and Mark Updegraff as they reflect on: How to know when to pivot in your career Building a business Finding people that you resonate with and asking questions Joining a mastermind and expanding your network Scaling your growing real estate business Gross...
ISP 260: Five Ways You Can Find Off Market Deals 25.03.2025 14:19
Episode 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 developing a multi-faceted approach when searching fo...
ISP 259: Friday Look Back - Unlocking The Power of Off Market Deals 21.03.2025 13:33
Episode 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 pre-foreclosure properties, enhances the likelih...
ISP 258: Why Are Mortgage Rates Falling? 18.03.2025 6:54
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 Estate for Investors We have open investment oppo...
ISP 257: Friday Look Back -What's Your Personal Investment Strategy? 07.03.2025 10:53
Episode 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 you? What are your actual goals for investi...
ISP 256: Finding Hidden Multifamily Opportunities with Andrea Foley 06.03.2025 56:08
Episode 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.sastexascapital.com Download our FREE E-Book - Multifa...
ISP 255: Friday Look Back - Mailbag: Long & Short Term Investing Strategies 28.02.2025 10:58
Episode 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. The importance of aligning investment stra...
ISP 254: Proven Leasing Strategies For When Your Property Won't Rent 25.02.2025 13:39
Episode 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 understanding local trends. Tailoring marketing...
ISP 253: Friday Look Back - 5 Tips For Beginning Investors 21.02.2025 12:32
Episode 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 right team. We have open investment opportunities. W...
ISP 252: Have You Considered Building Vs Buying? 18.02.2025 12:19
Episode 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 aware, research, and understand what the mark...
ISP 251: Friday Look Back - The Biggest Barrier to Getting Started: Fear! 14.02.2025 11:30
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, having a mentor can significantly accelerate t...
ISP 250: Having a Coach or Mentor Alongside You 11.02.2025 37:43
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 finding focus as a real estate investo...
ISP 249: Friday Look Back - Why Real Estate Investing? 07.02.2025 10:34
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. Time, not money, is the true currency of life....
ISP 248: Investment Advice with Yonah Weiss 05.02.2025 38:48
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? Check out www.sastexascapital.com Download...
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