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PODCAST

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.

business investing

All Episodes

47:13

ISP 361: Ground Up Development in Brooklyn, NY with...

Invest Smarter Podcast ·

2026/04/21

Invest Smarter Podcast Episode 361: Ground Up Development in Brooklyn, NY with Aaron Yassin Host: Simon Castillo Guest: Aaron Yassin Simon Castillo is joined by Aaron Yassin to discuss: Combining a passion for art and real estate: It’s not just the aesthetics of a building, it’s everything about the building In all investments, there are risks Reliance on market conditions and other external factorsBest use value for buildings that have already been built De...

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46:30

ISP 360: Own Your Time and Make a Lasting Impact In...

Invest Smarter Podcast ·

2026/04/14

Invest Smarter Podcast Episode 360: Own Your Time and Make a Lasting Impact In Your Work with Marcus Arredondo Host: Simon Castillo Guest: Marcus Arredondo Simon Castillo is joined by Marcus Arredondo to discuss: Owning your time The value of making an impact in your work “We’re not real estate investors, we’re problem solvers.” How do you properly vet a property manager? The ups and downs of pivoting in your real estate business We have open...

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45:55

ISP 359: Building Wealth with a Marine Mindset

Invest Smarter Podcast ·

2026/04/07

Invest Smarter Podcast Episode 359: Building Wealth with a Marine Mindset Host: Simon Castillo Guest: Shelon ‘Hutch’ Hutchinson Simon Castillo is joined by Shelon ‘Hutch’ Hutchinson to discuss: Where and how to start as a real estate investorOwnership is a long term pathway to prosperitySetting a goal and taking action, is often a missing piece with real estate investors Military experiences and skills that are useful for real estate investors Real estate...

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46:14

ISP 358: Diversify Using New Real Estate Classes with...

Invest Smarter Podcast ·

2026/03/31

Invest Smarter Podcast Episode 358: Diversify Using New Real Estate Classes with Jonathan Cattani Host: Simon Castillo Guest: Jonathan Cattani Simon Castillo is joined by Jonny Cattani to discuss: RaiseMasters Mastermind This is where true wealth is made and preserved How to communicate with investors and give them a sense of security to trust you with their capital What is the draw for an investor to invest with you? What is the capital raising envi...

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18:41

ISP 357: Friday Look Back - What Every Passive...

Invest Smarter Podcast ·

2026/03/27

Invest Smarter Podcast Episode 357: Friday Look Back - What Every Passive Investor Should Do Before Investing in a Real Estate Syndication Host: Simon Castillo Producer: April Munson Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: Ask for references from other investors As a passive investor, you should understand what the strategy is Review the syndication’s offering documents to understand what the risks are involved with th...

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9:42

ISP 356: Friday Look Back - Do You Have a Real Estate...

Invest Smarter Podcast ·

2026/03/20

Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: Do you have a real estate investor’s mindset? Having clarity that you can’t always control your circumstances, but you can control how you respond to those circumstancesLimiting beliefs are powerful hurdles that we all have to overcomeThink of yourself as an entrepreneur rather than an investor Be clear on your focus, your goals, and your ‘why’ We have open investme...

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46:31

ISP 355: Finding a Niche in Self Storage

Invest Smarter Podcast ·

2026/03/17

Episode 355: Finding a Niche in Self Storage Host: Simon Castillo Guest: Russell Nersesov Join our host Simon Castillo and Russell Nersesov as they discuss: It takes a village to work on a multifamily project Is there a huge difference between the financials, economics, and returns that investors see in self storage compared to multifamily? How to recognize a good investment deal? We have open investment opportunities. Want to learn more? Check out www.sastexascapit...

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13:50

ISP 354: Friday Look Back - Understanding Syndication...

Invest Smarter Podcast ·

2026/03/13

Episode 354: Friday Look Back - Understanding Syndication Structures Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: We have short term investment opportunities open to you right now! Understanding syndications and their structures You need to know where to start before you know if an investment is a good fit for you Components that you need to review when evaluating a real estate syndication dealSplit between li...

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47:13

ISP 353: Scaling Rapidly with Commercial Real Estate...

Invest Smarter Podcast ·

2026/03/10

Episode 353: Scaling Rapidly with Commercial Real Estate Featuring Carlos Salguero Host: Simon Castillo Guest: Carlos Salguero Join our host Simon Castillo and Carlos Salguero as they discuss: What is the best vehicle to invest my money? Attracting talent is an essential part of scaling a business to any significant size The value of building the right team in your business The importance of tenant treatment If people don’t know you, they can’t do business with...

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13:16

ISP 352: Friday Look Back - Capital Preservation is...

Invest Smarter Podcast ·

2026/03/06

Episode 352: Friday Look Back - Capital Preservation is the #1 Metric to Look For Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: What does capital preservation mean? The importance of focusing on capital preservationOur number 1 priority - we focus on how to not lose money 5 pillars that make up our capital preservation strategy We have open investment opportunities. Want to learn more? Check out www.saste...

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41:57

ISP 351: 4000 Units as a Full-Time CPA

Invest Smarter Podcast ·

2026/03/03

Episode 351: 4000 Units as a Full-Time CPA Host: Simon Castillo Guest: Scott Jacobson Join our host Simon Castillo and Scott Jacobson as they discuss: “Your W2 won’t build wealth for you, the way that real estate can.” Have a good firm grasp of the fundamentals of investing Grow your education and grow your teamIntegrity in real estate - your word is your bond 1035 Exchange We have open investment opportunities. Want to learn more? Check out www.sastexasc...

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15:18

ISP 350: Friday Look Back - Mailbag: Pro’s and Cons...

Invest Smarter Podcast ·

2026/02/27

Episode 350: Friday Look Back - Mailbag: Pro’s and Cons of Subject To Deals Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: What is a Subject To deal? Why would anyone sell a property ‘Subject To’? What are the risks to the seller and the buyer in a Subject To deal? What is the seller’s outlook in the next few years? How can you present solutions to a problem to the seller? Understanding a ‘Due On...

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41:56

ISP 348: Building Wealth With Customizable Funds...

Invest Smarter Podcast ·

2026/02/24

Episode 348: Building Wealth With Customizable Funds Featuring Jeff Greenberg Host: Simon Castillo Guest: Jeff Greenberg Join our host Simon Castillo and Brian Bradley as they discuss: Running a business alongside the right team Opportunities present themselves often when people are not looking - be ready to jump when it presents itselfJeff Greenberg discusses his funds Protecting investor capital We have open investment opportunities. Want to learn more? Check out ...

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15:18

ISP 348: Friday Look Back - Mailbag: Pro’s and Cons...

Invest Smarter Podcast ·

2026/02/20

Episode 348: Friday Look Back - Mailbag: Pro’s and Cons of Subject To Deals Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: What is a Subject To deal? Why would anyone sell a property ‘Subject To’? What are the risks to the seller and the buyer in a Subject To deal? What is the seller’s outlook in the next few years? How can you present solutions to a problem to the seller? Understa...

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46:41

ISP 347: Key Metrics & Red Flags to Look for in...

Invest Smarter Podcast ·

2026/02/17

Episode 347: Key Metrics & Red Flags to Look for in Multifamily Investment Host: Simon Castillo Guest: Ruben Dominguez Join our host Simon Castillo and Ruben Dominguez as they discuss: You need to be able to build a team Right now is the time to buy Key metrics to look for in a deal Who is your sponsor and how is their track record? What are your exit costs and exit timeline? We have open investment opportunities. Want to learn more? Check out www.sast...

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13:54

ISP 346: Friday Look Back - Fix & Flips vs Passive...

Invest Smarter Podcast ·

2026/02/13

Episode 346: 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 vs. passive real estate investing Understanding market dynamics We ...

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44:48

ISP 345: Protecting Your Wealth with Asset Protection...

Invest Smarter Podcast ·

2026/02/10

Episode 345: Protecting Your Wealth with Asset Protection Layers Host: Simon Castillo Guest: Brian Bradley Join our host Simon Castillo and Brian Bradley as they discuss: How to protect your wealth What are non-exempt exposed assets? LLCs & asset protectionECCC - Effectiveness, Control, Cost, Compliance What is a Hybrid Trust and how does it protect assets? Understanding what an Asset Protection Trust is and how it works Fraud and tax avoidance We...

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18:20

ISP 344: Friday Look Back - Pivoting to Short Term...

Invest Smarter Podcast ·

2026/02/07

Episode 344: Friday Look Back - Pivoting to Short Term Lending Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: New Investment Opportunity! What are the benefits for you as an investor to allocate your capital into this growing development business? Working on our 31st project in San Antonio, Texas We have open investment opportunities. Want to learn more? Check out www.sastexascapital.comDownload ...

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45:48

ISP 343: Building a Single Family Property Business

Invest Smarter Podcast ·

2026/02/03

Episode 343: Building a Single Family Property Business Host: Simon Castillo Guest: Bill Lockhart Join our host Simon Castillo and Sam Bates 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 the right partners and the right people on your team We have open inves...

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16:00

ISP 342: Friday Look Back - 3 Reasons Real Estate...

Invest Smarter Podcast ·

2026/01/30

Episode 342: Friday Look Back - 3 Reasons Real Estate Outperforms Stocks Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: “Why invest in real estate when you can invest in the stock market?” Tax benefits written into the Tax Code Investing in real estate allows you to have more control over your investment Understand what forced depreciation is and how it works We have open investment opportun...

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361 results

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