Simon Castillo

Invest Smarter Podcast

Business EN ↓ 388 episodes

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

Business

Latest episode

Oct 27, 2026

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Episodes

ISP 388: How to Navigate Your W2 and Grow Your Real Estate Portfolio 27.10.2026

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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