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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 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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Episode 163: Friday Look Back - Should You Buy a Rental Property Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: When is the good time to buy a rental property? No matter what field you're in, real estate and its passive income capability and tax advantages are absolutely unmatched. Rea…
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Invest Smarter Podcast Episode 162: Tips On Managing Your General Contractors Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: The challenges that real estate investors and even homeowners face when dealing with general contractors Tips on how to make sure you can manage your general contractor better in…
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Episode 161: Friday Look Back - Taking a Wrecking Ball to Realtor Fees in America Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The issue about the landmark case involving NAR. Will it lead to lower housing prices? Competition will enter the market and a new business model will come i…
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Invest Smarter Podcast Episode 160: Don't Fall For Bad Advice Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Business advice that's out their on the internet that are just wrong. Thinking with your heart and not with your brain, your setting yourself up for failure Think with your brain and use logic S…
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Episode 159: Friday Look Back - Keep it Simple Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Focusing on one thing and keeping it simple The easiest to do is to create one goal for yourself as an investor Having to define your criteria for your goal Not falling for the trap of complex…
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Invest Smarter Podcast Episode 158: Flashback Episode: Invest Smarter Utilizing 1031 Exchanges with Justin Kiehne Host: Simon Castillo Guest: Justin Kiehne Producer: April Munson Simon Castillo is joined by Justin Kiehne to discuss: Coming to the realization that there are different pathways to growing financial stability aside from exchanging time…
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Invest Smarter Podcast Episode 157: Friday Look Back - Should You Hire a Property Manager? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Three reasons why it's important to have a property management company The property management company will handle a lot of day-to-day task on your …
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Invest Smarter Podcast Episode 156: Choosing the Best Real Estate Investing Strategy for You Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: The best way to start investing in real estate. How to personally determine the best path is on investing in real estate. What should you invest in. Young professi…
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Invest Smarter Podcast Episode 155: Friday Look Back - Short Term Rental or Long Term Rentals? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Advantages and disadvantages of short term rentals What is it that you’re looking to do? With short term rentals, you’re competing in the world …
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Invest Smarter Podcast Episode 154: Anatomy of a Deal Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: What are the economics of a property? What is the anatomy of a deal? A blueprint for things that you should consider when looking at deals We have open investment opportunities. Want to learn more? Chec…
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Invest Smarter Podcast Episode 153: Friday Look Back - 5 Mistakes to Avoid When Renovating A Property Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: 5 common mistakes people make when making renovations to a property Keep up with quotes and invoices throughout renovation project Code c…
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Invest Smarter Podcast Episode 152: The Path to Scaling Your Real Estate Business Host: Simon Castillo Guest: Chris Lento Simon Castillo is joined by Chris Lento to discuss: When are you comfortable leaving your day job? The path to scaling your business You are going to have to learn how to raise capital Partnering with others is key The rates wil…
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Invest Smarter Podcast Episode 151: 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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Invest Smarter Podcast Episode 150: Beyond Borders: Jonathan Wei’s Path to Real Estate Syndication Host: Simon Castillo Guests: Jonathan Wei Simon Castillo is joined by Jonathan Wei to 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 …
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Invest Smarter Podcast Episode 149: Friday Look Back - Want to Get Started in Real Estate? Do This First! Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: How do you get started in real estate? Begin to educate yourself Position yourself to be around other investors Your network is your …
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Invest Smarter Podcast Episode 148: 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 opportunities. Want to learn mo…
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Invest Smarter Podcast Episode 147: Friday Look Back - What's Better: 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 way to get started investing in real estate? What can you do with $250,000? You may not be great at every single step in cl…
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Invest Smarter Podcast Episode 146: 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 Yo…
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Invest Smarter Podcast Episode 145: Friday Look Back - One Thing You Can Do Today To Start Raising Capital Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back as he reflects on: What is your track record? What kind of operations experience do you have? Partnerships are win-win opportunities if structured correctly We…
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Invest Smarter Podcast Episode 144: Having Compassion When Evicting Tenants Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Top tips for executing your business plan as investors The importance of treating tenants with respect What does the eviction process look like? In many states, text messages are t…
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Invest Smarter Podcast Episode 143: Friday Look Back - Deducting Real Estate Losses as a Private Investor Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Lookback as he reflects on: You cannot take passive losses unless you have passive income to offset it How depreciation losses can benefit you as an investor We have open…
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Invest Smarter Podcast Episode 142: Getting Started Raising Capital Host: Simon Castillo Producer: April Fischer Join our host Simon Castillo as he reflects on: Why is raising capital important? Start with your friends and family What made it hard to raise capital in 2023? Building your brand so that you audience begins to know, like, and trust you…
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Invest Smarter Podcast Episode 141: Friday Look Back: Master the Skill of Investing Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Lookback as he reflects on: Investing as a skill Repeatable success strategy Business plans and business models Double down on what is working What do you specialize in We have open investment…
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Invest Smarter Podcast Episode 4: Taking Action and Failing Forward Host: Simon Castillo Guest: Jeffrey Donis Simon Castillo is joined by Jeffrey Donis to discuss: Living your dream Overcoming analysis paralysis Wholesaling in real estate Taking action and failing forward Jeffrey Donnis is a real estate investor and syndicator. Jeffrey and his two …
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Invest Smarter Podcast Episode 139: Friday Look Back: Listener Mailbag: Real Estate Due Diligence Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Lookback as he reflects on: Is an opportunity really as great as it seems? Real Estate Due Diligence We have open investment opportunities. Want to learn more? Check out www.sast…
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