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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 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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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 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 an…
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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 Netw…
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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 pr…
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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.…
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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…
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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 rea…
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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 p…
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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? Ch…
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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 buy…
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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 lo…
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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…
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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 Scal…
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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 develop…
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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 …
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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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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 …
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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.sastexascap…
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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…
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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 underst…
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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 righ…
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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 awar…
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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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