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.
Author
Simon Castillo
Category
Podcast website
Latest episode
Jul 7, 2026
Where to listen?
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Episodes
ISP 97: Friday Look Back - The Risks Of Cutting Corners In The Due Diligence Process 11.08.2023 11:30
Invest Smarter Podcast Episode 97: Friday Look Back - The Risks Of Cutting Corners In The Due Diligence Process Host: Simon Castillo Producer: April Munson Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: You should have a process for due diligence The risks of cutting corners in the due diligence process 2 phase due diligence process You want a ‘quick no’ or...
ISP 96: Building Wealth with a Marine Mindset 08.08.2023 45:55
Invest Smarter Podcast Episode 96: Building Wealth with a Marine Mindset Host: Simon Castillo Guest: Shelon ‘Hutch’ Hutchinson Producer: April Munson Simon Castillo is joined by Shelon ‘Hutch’ Hutchinson to discuss: Where and how to start as a real estate investor Ownership is a long term pathway to prosperity Setting a goal and taking action, is often a missing piece with real estate investor...
ISP 95: Friday Look Back - What Every Passive Investor Should Do Before Investing in a Real Estate Syndication 04.08.2023 18:41
Invest Smarter Podcast Episode 95: 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’...
ISP 94: Diversify Using New Real Estate Classes with Jonathan Cattani 01.08.2023 46:14
Invest Smarter Podcast Episode 94: Diversify Using New Real Estate Classes with Jonathan Cattani Host: Simon Castillo Guest: Jonathan Cattani Producer: April Munson 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 W...
ISP 93: Friday Look Back - Do You Have a Real Estate Investor Mindset? 28.07.2023 9:42
Invest Smarter Podcast Episode 93: Friday Look Back - Do You Have a Real Estate Investor Mindset? Host: Simon Castillo Producer: April Munson 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 circumstances...
ISP 92: Finding a Niche in Self Storage 25.07.2023 46:31
Invest Smarter Podcast Episode 92: Finding a Niche in Self Storage Host: Simon Castillo Guest: Russell Nersesov Producer: April Munson Simon Castillo is joined by Russell Nersesov to 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...
ISP 91: Friday Look Back - Understanding Syndication Structures 21.07.2023 13:50
Invest Smarter Podcast Episode 91: Friday Look Back - Understanding Syndication Structures Host: Simon Castillo Producer: April Munson 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 investm...
ISP 90: Scaling Rapidly with Commercial Real Estate Featuring Carlos Salguero 18.07.2023 47:13
Invest Smarter Podcast Episode 90: Scaling Rapidly with Commercial Real Estate Featuring Carlos Salguero Host: Simon Castillo Guest: Carlos Salguero Producer: April Munson Simon Castillo is joined by Carlos Salguero to 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...
ISP 89: Friday Look Back - Capital Preservation is the #1 Metric to Look For 14.07.2023 13:16
Invest Smarter Podcast Episode 89: Friday Look Back - Capital Preservation is the #1 Metric to Look For Host: Simon Castillo Producer: April Munson 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 preservation Our number 1 priority - we focus on how to not lose money 5 pillars that m...
ISP 88: 4000 Units as a Full-Time CPA 11.07.2023 41:57
Invest Smarter Podcast Episode 88: 4000 Units as a Full-Time CPA Host: Simon Castillo Guests: Scott Jacobson Producer: April Munson Simon Castillo is joined by Scott Jacobson to 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 team Integrity in real estate - your word is your...
ISP 87: Friday Look Back - Mailbag: Pro's and Cons of Subject To Deals 07.07.2023 15:18
Invest Smarter Podcast Episode 87: Friday Look Back - Mailbag: Pro’s and Cons of Subject To Deals Host: Simon Castillo Producer: April Munson 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 out...
ISP 86: Building Wealth With Customizable Funds Featuring Jeff Greenberg 04.07.2023 41:56
Invest Smarter Podcast Episode 86: Building Wealth With Customizable Funds Featuring Jeff Greenberg Host: Simon Castillo Guest: Jeff Greenberg Producer: April Munson Simon Castillo is joined by Jeff Greenberg to discuss: Running a business alongside the right team Opportunities present themselves often when people are not looking - be ready to jump when it presents itself Jeff Greenberg discus...
ISP 85: Friday Look Back - Fix & Flips vs Passive Real Estate Investing: Which Is Right For You? 30.06.2023 13:54
Invest Smarter Podcast Episode 85: Friday Look Back - Fix & Flips vs Passive Real Estate Investing: Which Is Right For You? Host: Simon Castillo Producer: April Munson Join our host Simon Castillo for a one on one Friday Look Back where 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...
ISP 84: Key Metrics & Red Flags to Look for in Multifamily Investments 27.06.2023 46:41
Invest Smarter Podcast Episode 84: Key Metrics & Red Flags to Look for in Multifamily Investments Host: Simon Castillo Guest: Ruben Dominguez Producer: April Munson Simon Castillo is joined by Ruben Dominguez to 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...
ISP 83: Friday Look Back - Pivoting to Short Term Lending 23.06.2023 18:20
Invest Smarter Podcast Episode 83: Friday Look Back - Pivoting to Short Term Lending Host: Simon Castillo Producer: April Munson Join our host Simon Castillo for a one on one Friday Look Back where 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,...
ISP 82: Building a Single Family Property Business 20.06.2023 45:48
Invest Smarter Podcast Episode 82: Building a Single Family Property Business Host: Simon Castillo Guest: Bill Lockhart Producer: April Munson Simon Castillo is joined by Bill Lockhart to 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 -...
ISP 81: Friday Look Back - 3 Reasons Real Estate Outperforms Stocks 16.06.2023 16:00
Invest Smarter Podcast Episode 81: Friday Look Back - 3 Reasons Real Estate Outperforms Stocks Host: Simon Castillo Producer: April Munson Join our host Simon Castillo for a one on one Friday Look Back where 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 yo...
ISP 80: Protecting Your Wealth with Asset Protection Layers 13.06.2023 44:48
Invest Smarter Podcast Episode 80: Protecting Your Wealth with Asset Protection Layers Host: Simon Castillo Guest: Brian Bradley Producer: April Munson Simon Castillo is joined by Brian Bradley to discuss: How to protect your wealth What are non-exempt exposed assets? LLCs & asset protection ECCC - Effectiveness, Control, Cost, Compliance What is a Hybrid Trust and how does it protect as...
ISP 79: Friday Look Back - Mailbag: 4 Things To Look For in Every Deal 09.06.2023 22:11
Invest Smarter Podcast Episode 79: Friday Look Back - Mailbag: 4 Things To Look For in Every Deal Host: Simon Castillo Producer: April Munson Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: What should I be looking for in a deal, as a passive investor? What is the story behind the deal? Understand the fee structure Does the operator have experience? Look...
ISP 78: Real Estate Investing Using a Fund with Brian Head 06.06.2023 42:12
Invest Smarter Podcast Episode 78: Real Estate Investing Using a Fund with Brian Head Host: Simon Castillo Guest: Brian Head Producer: April Munson Simon Castillo is joined by Brian Head to discuss: The value of ‘time blocking’ Economic changes in the market Affordability leading to more individuals renting rather than purchasing homes Changes in interest rates Are you comfortable asking pe...
ISP 77: Friday Look Back - How to NOT Lose Money in Real Estate 02.06.2023 16:51
Invest Smarter Podcast Episode 77: Friday Look Back - How to NOT Lose Money in Real Estate Host: Simon Castillo Producer: April Munson Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: Nothing is 100% certain in the investing world Capitalization and speculation are what sank many investors during the financial crisis in 2008-2009 and are impacting many invest...
ISP 76: How to Overcome Challenges and Setbacks as a Real Estate Investor 30.05.2023 36:07
Invest Smarter Podcast Episode 76: How to Overcome Challenges and Setbacks as a Real Estate Investor Host: Simon Castillo Guest: Sam Bates Producer: April Munson Simon Castillo is joined by Sam Bates to discuss: Mistakes made when investing in single family Working on too many house flips at once How do you get banks and investors to put trust in you without having done a development deal in...
ISP 75: Friday Look Back - What Makes a Deal Attractive? 26.05.2023 22:57
Invest Smarter Podcast Episode 75: Friday Look Back - What Makes a Deal Attractive? Host: Simon Castillo Producer: April Munson Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: Wealth & Whiskey MeetUp - June 14th 2023 We now have a free private Facebook group! - Name of group: Wealth & Whiskey New FREE eBook coming soon! How do we know as multifamily...
ISP 74: From RV Parks to Multifamily: Passively Investing in Real Estate Syndications 23.05.2023 39:52
Invest Smarter Podcast Episode 74: From RV Parks to Multifamily: Passively Investing in Real Estate Syndications Host: Simon Castillo Guest: Nick Boivin Producer: April Munson Simon Castillo is joined by Nick Boivin to discuss: Having control over your investment Understanding what a syndication is Accounting for ongoing expenses of having a rental property Investing in self storage Investi...
ISP 73: Friday Look Back - Why Spending $20,000 on a Coaching Program is Worth It 19.05.2023 14:22
Invest Smarter Podcast Episode 73: Friday Look Back - Why Spending $20,000 on a Coaching Program is Worth It Host: Simon Castillo Producer: April Munson Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: Celebrating compliments on our December 2022 deal as it shows confidence in our ability as operators to take the property to full potential The benefits of joi...
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