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.
Be sure to visit the podcast's website and support the creator: investsmarterpodcast.buzzsprout.com
Author
Simon Castillo
Category
Podcast website
Latest episode
Oct 27, 2026
Where to listen?
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Episodes
ISP 388: How to Navigate Your W2 and Grow Your Real Estate Portfolio 27.10.2026 14:48
Episode 388: 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 to help streamline your workload. Time is proba...
ISP 387: The Four Quadrants of Real Estate Investing 20.10.2026 18:00
Episode 387: 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. When you sell your property, don't sell it th...
ISP 386: Single Family Versus Commercial Real Estate 13.10.2026 11:39
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 can be risky if not structured properly. Commercial Real Estate investing can be more scaleable and simple...
ISP 385: Tips On Managing Your General Contractors 06.10.2026 27:12
Invest Smarter Podcast Episode 385: 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 the future Communication is so important, a la...
ISP 384: Don't Fall For Bad Advice 30.09.2026 20:00
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 Study the market for what it is Creating a business solely because of passion and it doesn't pencil o...
ISP 383: Invest Smarter Utilizing 1031 Exchanges with Justin Kiehne 22.09.2026 49:25
Host: Simon Castillo Guest: Justin Kiehne 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 for dollars. “If you’re open to opportunities, you will find opportunities.” The differences between the 1031 exchange and Delaware Statutory Trust (DST) We have open investment opport...
ISP 382: Choosing the Best Real Estate Investing Strategy for You 15.09.2026 23:31
Invest Smarter Podcast Episode 382: 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 professionals recognize that real estate is a great way...
ISP 381: Anatomy of a Deal 08.09.2026 14:14
Invest Smarter Podcast Episode 381: 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? Check out www.sastexascapital.com Download our FRE...
ISP 380: The Path to Scaling Your Real Estate Business 01.09.2026 41:07
Invest Smarter Podcast Episode 380: The Path to Scaling Your Real Estate Business Host: Simon Castillo Guests: 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 will come down, but when? How do you get com...
ISP 379: Beyond Borders: Jonathan Wei’s Path to Real Estate Syndication 25.08.2026 38:06
Invest Smarter Podcast Episode 379: 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 We have open investment opportunities. Wa...
ISP 378: Actionable Steps To Start Building Wealth 18.08.2026 26:01
Invest Smarter Podcast Episode 378: Actionable Steps To Start Building Wealth Host: Simon Castillo Join our host Simon Castillo 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 more? Check out www.sastexascapital.com Download our FREE E-Book - Multi...
ISP 377: Overcoming Analysis Paralysis and Taking Action 11.08.2026 22:19
Invest Smarter Podcast Episode 377: Overcoming Analysis Paralysis and Taking Action Host: Simon Castillo Join our host Simon Castillo 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 have to be perfect to start - you have to take a...
ISP 376: Having Compassion When Evicting Tenants 04.08.2026 25:03
Invest Smarter Podcast Episode 376: Having Compassion When Evicting Tenants Host: Simon Castillo Join our host Simon Castillo 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 treated as legal written notice We have open investment opportunities....
ISP 375: Getting Started Raising Capital 28.07.2026 20:19
Invest Smarter Podcast Episode 142: Getting Started Raising Capital Host: Simon Castillo 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 Do you have a basic understanding of who your investors are? Consis...
ISP 374: The Surprising Lucrative Real Estate Asset Class with Stewart Heath 21.07.2026 44:28
Invest Smarter Podcast Episode 374: The Surprising Lucrative Real Estate Asset Class with Stewart Heath Host: Simon Castillo Guests: Stewart Heath Simon Castillo is joined by Stewart Heath to 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 Tennessee Valley We have open inve...
ISP 373: Multifamily Investing as a Maritime Captain with Scott Kidd 14.07.2026 37:58
Host: Simon Castillo Guests: Scott Kidd Simon Castillo is joined by Scott Kidd to discuss: Without a great team, the boat doesn’t go anywhere Finding time to manage general partners while traveling Without the investors, these opportunities wouldn’t be available We have open investment opportunities. Want to learn more? Check out www.sastexascapital.com Download our FREE E-Book - Multifamily...
ISP 372: Navigating Industrial Real Estate with Angel Gonzalez 07.07.2026 43:28
Host: Simon Castillo Guests: Angel Gonzalez Simon Castillo is joined by Angel Gonzalez to discuss: What does servant leadership mean to you? The importance of building lasting relationships Bridging single family to commercial family The future landscape of investing over the next 12 months We have open investment opportunities. Want to learn more? Check out www.sastexascapital.com Download ou...
ISP 371: Flashback Episode: Real Estate Is The Best Vehicle For Taking Financial Control Of Your Life with John Pearl 30.06.2026 38:21
Episode371: Flashback Episode: Real Estate Is The Best Vehicle For Taking Financial Control Of Your Life with John Pearl Host: Simon Castillo Guest: John Pear Simon Castillo is joined by John Pearl to discuss: Trading time for money Freedom Investor Radio Communication is key Start storing money to invest it Stay focused on your long term goals Keep your ‘why’ in the front of your mind We h...
ISP 370: Understanding Your Risk Tolerance 23.06.2026 11:31
Invest Smarter Podcast Episode 370: Understanding Your Risk Tolerance Host: Simon Castillo Producer: April Munson Join our host Simon Castillo as he reflects on: Risk Tolerance / Investor Tolerance Understanding different types of risk The appropriateness of your investment should match your goals Identify deals that align with your goals We have open investment opportunities. Want to learn...
ISP 369: Investing in the Booming Austin, TX Market with Andrew Campbell 16.06.2026 48:31
Host: Simon Castillo Guest: Andrew Campbell Simon Castillo is joined by Andrew Campbell to discuss: “Working in real estate is more about freedom than retirement” What is your process around raising capital? What challenges did you encounter raising capital? Every investor and every investment is different Andrew Campbell is a native Austinite and Managing Partner at Wildhorn. He is a real est...
ISP 368: Building Success with Industrial Flex Space 09.06.2026 45:00
Episode 368: Building Success with Industrial Flex Space Host: Simon Castillo Guest: Shannon Robnett Simon Castillo is joined by Shannon Robnett to discuss: We’re not looking at a new real estate market - we’re looking at instability People are looking for leaders Navigating change in the marketplace What you can’t find, you can usually build What does the debt structure look like for these...
ISP 367: My Real Estate Investing Journey on the Multifamily Insights Podcast 02.06.2026 42:19
Invest Smarter Podcast Episode 367: My Real Estate Investing Journey on the Multifamily Insights Podcast Host: John Casmon Guest: Simon Castillo John Casmon is joined by Simon Castillo on the Multifamily Insights Podcast to discuss: Networking opening up a whole new world to passive investing The hardest part of becoming a general partner The importance of shifting your mindset Multifamily i...
ISP 366: 3 Mistakes to Avoid as a Passive Investor 26.05.2026 24:11
Invest Smarter Podcast Episode 366: 3 Mistakes to Avoid as a Passive Investor Host: Simon Castillo Guest: Wayne Courreges III Join our host Simon Castillo as he reflects on: Three of the most common mistakes that you want to avoid as a new passive investor Accelerate your learning curve based on others success Understand who the players are on a deal The impact of networking and vetting th...
Isp 365: Get your Money out of Prison & Generate Passive Income with Chris Miles 19.05.2026 53:22
Host: Simon Castillo Guest: Chris Miles Simon Castillo is joined by Chris Miles to discuss: God gave me the ability to bless lives, why not use it “It will take a miracle for me to be able to retire.” Real Estate is a safe and proven way to grow your wealth that actually works You tend to attract people who are like you You should have ‘smart debt’ Your mortgage is an asset Chris Miles, the...
ISP 364: From the U.S. Marine Corps to Successful Real Estate Investor with Wayne Courreges III 12.05.2026 52:55
Invest Smarter Podcast Episode 364: From the U.S. Marine Corps to Successful Real Estate Investor with Wayne Courreges III Host: Simon Castillo Guest: Wayne Courreges III Simon Castillo is joined by Wayne Courreges III to discuss: Find the right sponsor / general team to invest with What is your involvement with decision making Philosophy on asset management Everything around what we do is a...
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