Simon Castillo

Invest Smarter Podcast

Business EN ↓ 372 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. 

Author

Simon Castillo

Category

Business

Latest episode

Jul 7, 2026

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Episodes

ISP 297: Friday Look Back - The Best Way To Get Started, Is To Get Educated 15.08.2025

Episode 297: Friday Look Back - The Best Way To Get Started, Is To Get Educated Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  Understanding what a real estate investment trust is.  Investing in real estate without owning property   Earning passive income through dividends  We have open investment opportunities. Want to learn more?...

ISP 296: True Wealth Is Made During A Recession 12.08.2025

Episode 296: True Wealth Is Made During A Recession  Host: Simon Castillo  Guest: Max Gonzales Join our host Simon Castillo and Max Gonzales  as they discuss: Multifamily is a team sport  Should I wait to invest?  Buy low, sell high  It wasn’t a real estate crash, it was a liquidity crisis The more assets you have, the more playing cards that you have  It’s never easy doing deals  What is: Retrade...

ISP 295: Friday Look Back - Understanding What A Real Estate Investment Trust Is (REIT) 08.08.2025

Episode 295: Friday Look Back - Understanding What A Real Estate Investment Trust Is (REIT) Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  Understanding what a real estate investment trust is.  Investing in real estate without owning property   Earning passive income through dividends  We have open investment opportunities. Want to...

ISP 294: Key Benefits Of Running A Multifamily Business 05.08.2025

Episode 294: Key Benefits Of Running A Multifamily Business  Host: Simon Castillo  Guest: Michael Piehler Join our host Simon Castillo and Michael Piehler  as they discuss: Difference between working in the stock market and working in real estate Key benefits of running a multifamily business  This thing called passive income’  There is such a thing as ‘good debt’ We have open investment opportuni...

ISP 293: Friday Look Back - How The Wealthy Use Debt To Become Wealthier 01.08.2025

Episode 293: Friday Look Back - How The Wealthy Use Debt To Become Wealthier Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  Black Friday  Differences between good debt and bad debt  Isn’t debt risky?  Using debt the right way can lead to compounding assets  Always invest in yourself We have open investment opportunities. Want to lea...

ISP 292: Do You Want To Be A Real Estate Investor Or Do You Want To Start A Real Estate Investing Company? 29.07.2025

Episode 292: Do You Want To Be A Real Estate Investor Or Do You Want To Start A Real Estate Investing Company? Host: Simon Castillo  Guest: Brian Alfaro  Join our host Simon Castillo and  Brian Alfaro  as they discuss: The reality of starting in residential real estate Property Rehabilitation  Transitioning from single family to multifamily  Get your mindset right (Cheesy? But necessary.) We have...

ISP 291: Friday Lookback - Once You Become An Active Syndicator - You’re Signing Up For A Very Different Life 25.07.2025

Episode 291: Friday Lookback - Once You Become An Active Syndicator - You’re Signing Up For A Very Different Life Host: Simon Castillo  Guest: Saket Jain Join our host Simon Castillo and Saket Jain for as the discuss: You don’t have to leave your W2 job to build generational wealth Should everyone become an investor?  Once you become an active syndicator, you’re signing up for a very different lif...

ISP 290: There Couldn’t Be A Better Time To Be An Entrepreneur 22.07.2025

Episode 290: There Couldn’t Be A Better Time To Be An Entrepreneur Host: Simon Castillo  Guest: Nir Wittenberg  Join our host Simon Castillo and Nir Wittenberg  as they discuss: Achieving a passive income lifestylethey Positioning yourself to be focused on the returns; part of real estate  The value of utilizing systems  Celebrate all of your ‘wins’ We have open investment opportunities. Want to l...

ISP 289: Friday Look Back - THIS Is How You Build A Bulletproof Mindset 18.07.2025

Episode 289: Friday Look Back - THIS Is How You Build A Bulletproof Mindset  Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  Fear is a big part of mindset  How do you build a bulletproof mindset How do you protect and build confidence We have open investment opportunities. Want to learn more? Check out www.sastexascapital.com Downloa...

ISP 288: The Power Of Tax Benefits In Real Estate Investing 15.07.2025

Episode 288: The Power Of Tax Benefits In Real Estate Investing  Host: Simon Castillo  Guest: K Trevor Thompson Join our host Simon Castillo and K Trevor Thompson as they discuss: The power of networking  How to monitor your investments and what to do when a deal isn’t advertised well  The power of tax benefits in real estate investing   The Compound Effect  We have open investment opportunities....

ISP 287: Educate Yourself and Take Action 11.07.2025

Episode 287: Educate Yourself and Take Action Host: Simon Castillo  Guest: Matt Hansen Join our host Simon Castillo and Matt Hansen to discuss: Leaving corporate America and entering real estate  Difference between investing in multifamily vs single family  The importance of vetting your sponsor  Being a General Partner is not for everyone  The difference between 506(b) and 506(c) We have open inv...

ISP 286: Real Estate Is The Best Vehicle For Taking Financial Control Of Your Life 08.07.2025

Episode 286: Real Estate Is The Best Vehicle For Taking Financial Control Of Your Life Host: Simon Castillo  Guest: John Pearl Join our host Simon Castillo and John Pearl as they 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 have open investment op...

ISP 285: Wealthy Doctor Secrets with TJ Visiodei 04.07.2025

Episode 285:  Wealthy Doctor Secrets with TJ Visiodei  Host: Simon Castillo  Guest: TJ Visiodei Join our host Simon Castillo and TJ Visiodei to discuss: :   The difference between being rich and wealthy Attracting the right people for the right deals We have open investment opportunities.  Want to learn more? Check out www.sastexascapital.com Download our FREE E-Book - Multifamily Millions - www.s...

ISP 284: Friday Look Back - 2 Skills YOU NEED On Your Journey To Building Wealth 27.06.2025

Episode 284: Friday Look Back - 2 Skills YOU NEED On Your Journey To Building Wealth  Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  Current deals at SAS Texas Capital Hurricane Ian  The infinite value of building your skills and acquiring your education  The significance of investing in yourself  We have open investment opportuniti...

ISP 283: Start With The End In Mind 25.06.2025

Episode 283: Start With The End In Mind  Host: Simon Castillo  Guest: Sandhya Seshadri Join our host Simon Castillo and Sandhya Seshadri to discuss: :   Achieving the role of Lead Sponsor in a deal  Being an active / passive investor  The value of investing in relationships  Agency debt coming back in a huge way  Individuals who invest based on emotion  If it’s a good time to sell - SELL  Finding...

ISP 282: Friday Lookback - How To Get Started In Real Estate Investing With Enough Capital To Match Your Budget 20.06.2025

Episode 282: Friday Lookback - How To Get Started In Real Estate Investing With Enough Capital To Match Your Budget Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  Due Diligence  How to get started in real estate investing  Hos can I get started in real estate and the stock market? 95% will never think about owning an additional prop...

ISP 281: Taking Action and Failing Forward 17.06.2025

Episode 281: Taking Action and Failing Forward  Host: Simon Castillo  Guest: Jeffrey Donis Join our host Simon Castillo and Jeffrey Donis to discuss:   Living your dream  Overcoming analysis paralysis  Wholesaling in real estate Taking action and failing forward We have open investment opportunities. Want to learn more? Check out www.sastexascapital.com Download our FREE E-Book - Multifamily Milli...

ISP 280: Friday Look Back - Fix & Flips vs Passive Real Estate Investing: Which Is Right For You? 13.06.2025

Episode 280: 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 involved you need to be between fix & flips...

ISP 279: Building a Single Family Property Business 10.06.2025

Episode 279: Building a Single Family Property Business Host: Simon Castillo  Guest: Bill Lockhart Join our host Simon Castillo with Bill Lockhart  as they discuss:  Wins and losses as a real estate investor  We’re more than just investors - we’re problem solvers  Subject 2 deals  The importance of having a clear title to a property  Real Estate is a team sport - it takes a team, it’s about having...

ISP 278: Friday Look Back - A Day in the Life of A Real Estate Investor 06.06.2025

Episode 278: Friday Look Back - A Day in the Life of A Real Estate Investor Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  The defensive improvement the Spurs showed during their recent games. Key performances from rising stars like Victor Wembanyama. The team’s growth and maturity as the season progresses. Fan reactions and what to...

ISP 277: How Do You Value Money? 03.06.2025

Episode 277:  How Do You Value Money? Host: Simon Castillo  Join our host Simon Castillo with Jim Lee to as they discuss:  How interest rate volatility is shaping investor sentiment in today’s market, The growing uncertainty around tariffs and their ripple effects across industries, Why real estate investors are reassessing risk in light of global economic shifts, And actionable strategies to stay...

ISP 276: Friday Look Back - Lawsuit Risk & How to Protect Yourself 30.05.2025

Episode 276: Friday Look Back - Lawsuit Risk & How to Protect Yourself Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  The hidden legal risks that can derail even the most well-run real estate ventures. Real-life lawsuits that reveal how one misstep can cost investors millions. Practical strategies to protect your assets through...

ISP 275: Creating The Path To Becoming A Real Estate Syndictor 27.05.2025

Episode 275:  Creating The Path To Becoming A Real Estate Syndictor Host: Simon Castillo  Join our host Simon Castillo with Jim Lee to as they 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  Networking is key to success in the real estate...

ISP 274: Friday Look Back - How I Bought A House for $8,000 23.05.2025

Episode 274: Friday Look Back - How I Bought A House for $8,000 Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  The recent shift in investor sentiment amid ongoing economic uncertainty. How inflation and interest rate expectations are reshaping the real estate landscape. Key insights from this week’s market movements and their broade...

ISP 273: Thinking About Leaving Your W2? 20.05.2025

Episode 273: Thinking About Leaving Your W2? Host: Simon Castillo  Join our host Simon Castillo for a one-on-one episode as he reflects on: How today’s economic uncertainty is reshaping investor mindsets The hidden impacts of rising tariffs on real estate and development Why fear-based decisions can derail your investment strategy What savvy investors are doing differently in a shifting market We...

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