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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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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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Episode 201: Friday Lookback - All Indicators Point to A Rate Cut Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Significant indicators that suggest an imminent interest rate cut, which is vital for both real estate investors and home buyers. The US 10-year treasury yield dropping belo…
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Episode 200: Raising Capital As An Introvert Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Successful capital raising is not about being the loudest voice in the room but about building trust and long-term relationships. Introverts can excel in raising capital by focusing on deep relationships, priori…
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Episode 199: Friday Lookback - Mortgage Rates Are Lower; Are You Buying? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: What impact have the recent drops in mortgage rates had on the housing market? Understanding the Federal Reserve’s actions and potential rate cuts is crucial for real…
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Episode 198: 8 Rules For Using Debt in Real Estate Investing Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: What are the contrasting views of financial gurus like Dave Ramsey and Robert Kiyosaki on using debt in real estate investing? Risks and benefits of using debt in real estate investing, emphasizi…
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Episode 197: Friday Lookback - Analyzing Deals & Making Offers Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: How important is deal analysis in real estate investing? Thorough analysis includes considering property information, purchase conditions, property conditions, financing detail…
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Episode 196: How to Find Your Next Rental Property Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Financial freedom through real estate is about gaining control over one’s time, not just accumulating properties. Starting with one property at a time and building momentum is key to wealth building in rea…
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Episode 195: Friday Look Back - Interest Rate Cuts Are Coming; Are We Already In A Buyer's Market? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The potential interest rate cuts. Will lower rates be enough to offset other market factors? The Bank of Canada’s rate cuts signal a need to…
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Episode 194: Friday Lookback - Beyond Cash Flow: Don't Forget About Appreciation Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: How to challenge some of the common assumptions around real estate investing. Exploring the balance between cash flow and growth. Keep your eyes open for deve…
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Episode 193: Building Wealth: Cash Flow Vs Growth Properties Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Which property helps you build wealth faster. Why are cash-flowing rentals considered to be lower risk. Growth rentals focus on the potential for the property to appreciate in value. The key take…
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Episode 192: Friday Look Back - Housing Market Outlook for Rest of 2024 Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: If you're looking to buy right now, be prepared for competition and potentially higher prices. Stay informed and act quickly when the opportunity arises. Hold on and h…
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Episode 191: Building Momentum in Business & Investing Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: The power of momentum. How to keep momentum. Starting small can often lead to bigger successes down the road Small wins you achieve will build your confidence The key is to start somewhere and keep pus…
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Invest Smarter Podcast Episode 190: Friday Look Back - Overcoming Anxiety and Fear of Failure Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Overcoming anxiety and the fear of failure Social media heightens our sense of failure Fear of rejection How do you manage the feelings of fear? …
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Episode 189: The One Thing Passive Investors Should Look For Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Why Track record is the number one thing an investor should look for. You'll need proof of a general partnership team and their ability to deliver results consistently. Companies that have been r…
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Episode 188: Friday Look back - Redfin Data Shows Renters Staying In Place Longer Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Rental trends in the United States. Factors that are driving people to rent longer. Longer tenancy can benefit both landlords by reducing turnover costs and …
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Episode 187: Earning Investor Trust & Raising Private Capital Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Why you must raise money and how to earn your investor's trust. With private money, you're not limited by your capital. Earning investor's trust is crucial, it unlocks benefits. Trust is when mo…
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Episode 186: Friday Look back - Mailbag Edition: Tapping Into Home Equity to Buy Investment Property Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Benefits that come when borrowing against your home equity. Start investing sooner. Understand the market you are investing in. Consider b…
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Episode 185: The Terminology Behind Real Estate Syndications Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Understanding the terminologies of this concept is crucial for real estate investors to make informed decisions. Ask as many questions as you have. Syndicators are showing adaptability by diversi…
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Episode 184: Friday Look back - Fed Leaves Rates Unchanged - What It Means 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: The Fed right now is projecting one rate cut during 2024. If inflations fall more rapidly than expected, then it is possible to see additi…
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Episode 183: 8 Things to Consider When Picking an Investment Strategy Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Critical factors to weigh in pursuing real estate investment. How to analyze and make a decision on what is the best investment path for you. 8 factors to consider when picking an invest…
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Episode 182: Friday Look Back - Do You Have to be a Handyman 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: The myth of a hands-on investor A lot of people always come up with reasons why they can start investing in real estate. At the end of the day, it comes…
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Episode 181: Scaling Into Multifamily Investing Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: How to actually acquire, operate, and scale a multifamily portfolio. What is it like managing multifamily properties. Outlining a roadmap to grow a real estate portfolio. We have open investment opportunities…
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Episode 180: Friday Look back - Introduction to Multifamily Investing Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Taking the real estate investing journey to the next level and building a scalable portfolio. Diving into the world of apartment buildings. Once you build up enough equi…
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Episode 179: Real World Investing - Rejected Offers & Funding Strategies Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Lining up your finances option. Building your core real estate team. Having a good realtor is a great place to start Receiving rejected offers is part of what every investor goes thro…
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Episode 178: Friday Look Back - Advice for Beginning Real Estate Investors & Common Mistakes to Avoid Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The common mistake for real estate beginners. Diversify and invest in multiple markets whenever you can. Buying property specifically for…
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Episode 177: How to Run a Short Term Rental Business Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Why does it require a business mindset to run short-term rentals. The myth of short-term rentals. Unlocking the possibilities for short-term rentals. Treating your short-term rentals with dedication and …
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Episode 176: Friday Look Back - Understanding Preferred Returns vs Cash on Cash Returns Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Important concepts for passive investors and real estate syndication. The metrics between preferred returns and cash-on-cash returns. Preferred returns…
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Episode 175: When free isn't free: the hidden cost of free advice Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Four pillars essential for personal growth. You can always start your education for free. There's so much information for you on the internet. How you can make sure that you are truly invest…
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Episode 174: Friday Look Back - How to Properly Vet a Property Management Company Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Right question to ask as an investor when vetting a property management company. A good management company can make or break a real estate portfolio. Ask abo…
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Episode 173: 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 place to build a br…
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Episode 172: Friday Look Back - What's Best: Active or Passive Investing? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: What is the best investing approach that suits you? There is a significant execution risk in finding and underwriting good deals. Knowing exactly when is the right t…
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Episode 171: Fix & Flips 101 Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: The fix and flips model is probably one of the more accessible entry points for most aspiring investors. There are still tremendous opportunities if you have the right frameworks and place. The key to success with the fix-and-f…
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Episode 170: Friday Look Back - Vetting General Contractor Budgets Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Understanding the numbers behind what the contractor is quoting you. What is your real long-term Return on Investment (ROI) by using that particular contractor? Knowing and…
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Episode 169: How to Navigate Your W2 and Grow Your Real Estate Portfolio Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Tips to navigate your W2 and grow your portfolio. Setting aside dedicated office hours for your side hustle. Focusing on real estate-related tasks. Leveraging automation and services …
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Episode 168: Friday Look back - Unpacking the Latest Fed Interest Rate Decision Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The Fed's decision to leave interest rate unchanged. Why interest rates are so important to real estate investors. Interest rates are basically your cost of mo…
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Episode 167: Friday Look Back - Should You Raise Money from Friends and Family? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Can you raise capital from your friends and family to get your real estate business off the ground? The two types of investors. The requirements to be a credit…
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Episode 166: The Four Quadrants of Real Estate Investing Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: How will you use single-family properties to build tangible wealth? The 1% rental value ratio. If you are starting out, where should you invest? Pick a submarket within your city. Wh…
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Episode 165: Friday Look Back - Should You Pay a Buyer's Agent? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: A huge change in the real estate landscape. Should you pay or not for a buyer's agent when you're buying a home? Buyer agents provide valuable services to home buyers by helpi…
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Episode 164: Single Family Versus Commercial Real Estate Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Single family vs commercial real estate, both provide you with traditional advantages in real estate investing in terms of cash flow, equity appreciation, and leverage depth, which c…
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