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 347: Key Metrics & Red Flags to Look for in Multifamily Investment 17.02.2026

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 ope...

ISP 346: Friday Look Back - Fix & Flips vs Passive Real Estate Investing: Which Is Right For You? 13.02.2026

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 v...

ISP 345: Protecting Your Wealth with Asset Protection Layers 10.02.2026

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 protection ECCC - Effectiveness, Control, Cost, Compliance  What is a Hybrid Trust and how does it protect assets?  Understanding what an Asset Pr...

ISP 344: Friday Look Back - Pivoting to Short Term Lending 07.02.2026

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 opportuni...

ISP 343: Building a Single Family Property Business 03.02.2026

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 ri...

ISP 342: Friday Look Back - 3 Reasons Real Estate Outperforms Stocks 30.01.2026

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 de...

ISP 341: Friday Look Back - Mailbag: 4 Things To Look For in Every Deal 23.01.2026

Episode 341: Friday Look Back - Mailbag: 4 Things To Look For in Every Deal  Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as 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 at the return structure We have open in...

ISP 340: How to Overcome Challenges and Setbacks as a Real Estate Investor 20.01.2026

Episode 340: How to Overcome Challenges and Setbacks as a Real Estate Investor  Host: Simon Castillo  Guest: Sam Bates Join our host Simon Castillo and Sam Bates as they 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 your career?  Managing the current f...

ISP 339: Friday Look Back - Why Spending $20,000 on a Coaching Program is Worth It 16.01.2026

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 joining a paid program  Having access to a network of people who will elevate your level of thinking  At the end...

ISP 338: Real Estate Investing Using a Fund with Brian Head 13.01.2026

Episode 338: Real Estate Investing Using a Fund with Brian Head Host: Simon Castillo  Guest: Brian Head Join our host Simon Castillo and Brian Head as they 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 people for money?  Diversification in y...

ISP 337: Friday Look Back - How to NOT Lose Money in Real Estate 09.01.2026

Episode 337: Friday Look Back - How to NOT Lose Money in Real Estate Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as 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 investors today Real Estate is a ‘get wealthy...

ISP 336: From RV Parks to Multifamily: Passively Investing in Real Estate Syndications 07.01.2026

Episode 336: From RV Parks to Multifamily: Passively Investing in Real Estate Syndications Host: Simon Castillo  Guest: Nick Boivin Join our host Simon Castillo and Elsa Nguyen as they discuss: Having control over your investment  Understanding what a syndication is  Accounting for ongoing expenses of having a rental property  Investing in self storage  Investing in an RV park  The importance of h...

ISP 335: Friday Look Back - 5 Principles You Need to Raise Private Capital 02.01.2026

Episode 332: Friday Look Back - 5 Principles You Need to Raise Private Capital Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  Raising Capital is a skill  What needs to be present in order for you to raise capital? Work on establishing genuine relationships Establish a strong track record for managing investment capital Align investo...

ISP 334: Persevering in Real Estate as a Vietnamese American with Elsa Nguyen 30.12.2025

Episode 334: Persevering in Real Estate as a Vietnamese American with Elsa Nguyen Host: Simon Castillo  Guest: Elsa Nguyen Join our host Simon Castillo and Elsa Nguyen as they discuss: The entrepreneurial journey as an immigrant  Challenges on the journey of success as an immigrant  Real estate is a team sport  The value and impact of growing your network  We have open investment opportunities. Wa...

ISP 333: Overcoming Limiting Beliefs and Taking Action to Achieve Your Goals 23.12.2025

Invest Smarter Podcast  Episode 333: Overcoming Limiting Beliefs and Taking Action to Achieve Your Goals Host: Simon Castillo  Guest: Caleb Johnson Join our host Simon Castillo and Caleb Johnson as they discuss: Family Hardships  House Hacking  Setting goals that stretch you, but are still realistic  Taking action  We have open investment opportunities. Want to learn more? Check out www.sastexasca...

ISP 332: Friday Look Back - Questions Investors Need To Be Asking 19.12.2025

Episode 332: Friday Look Back - Questions Investors Need To Be Asking Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  Another bank failure in the news  Interest rates are being raised  Number one rule of private equity in raising capital: Never lose the investors money Being properly capitalized Understanding who the property manager...

ISP 331: How to Grow Your Social Media Brand 16.12.2025

Invest Smarter Podcast  Episode 331: How to Grow Your Social Media Brand  Host: Simon Castillo  Guest: Lauren Kempf  Simon Castillo is joined by Lauren Kempf to discuss:  Overcoming the fear of starting your real estate business Imposter Syndrome  The impact of utilizing social media as a real estate investor  The value of community growth  Overcoming age, lack of real estate education and being a...

ISP 330: Friday Look Back - Doubt is the Killer of Dreams 12.12.2025

Episode 330: Friday Look Back - Doubt is the Killer of Dreams  Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  Check out last week’s episode: How Do You Define Success? What are the doubts, insecurities, and fears that keep you from being successful or pursuing success?  There are 3 main causes of doubt  Authentic Confidence  We have...

ISP 329: From Japan to Corporate America to Building a Real Estate Portfolio 09.12.2025

Episode 329: From Japan to Corporate America to Building a Real Estate Portfolio  Host: Simon Castillo  Guest: Yukiko Nakayama Join our host Simon Castillo and Yukiko Nakayama as they discuss: Transitioning to real estate from a corporate career  Overcoming barriers  Hard Money Lender  Investing in Self Storage Diversification We have open investment opportunities. Want to learn more? Check out ww...

ISP 328: Friday Look Back - How Do You Define Success? 05.12.2025

Episode 293: Friday Look Back - How Do You Define Success?  Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on:  Going after your dreams and impacting others along the way  Making a difference to the world around you (community, family, friends)  Success can be selfish  Changing your mindset from competitive to collaborative How can you l...

ISP 327: Creating The Path To Becoming A Real Estate Syndictor 02.12.2025

Episode 327: Creating The Path To Becoming A Real Estate Syndictor Host: Simon Castillo  Guest: Jim Lee  Join our host Simon Castillo and Jim Lee 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 re...

ISP 326: Friday Look Back - Live From the Wealth & Whisky 28.11.2025

Episode 326: Friday Look Back - Live From the Wealth & Whisky Host: Simon Castillo  Guest: Alex Weiche Join our host Simon Castillo and Alex Weiche for a Friday Look Back episode as they reflect on:  Entering the apartment syndication world  Passive investing in a fluctuating market  The effect of growing interest rates  Challenges in real estate  Breaking barriers when taking the steps to gro...

ISP 325: Building a Vertically Integrated Real Estate Business 25.11.2025

Episode 325: Building a Vertically Integrated Real Estate Business Host: Simon Castillo  Guest: Mark Updegraff Join our host Simon Castillo and Mark Updegraff as they discuss: How to know when to pivot in your career Building a business  Finding people that you resonate with and asking questions  Joining a mastermind and expanding your network Scaling your growing real estate business  Gross Rent...

ISP 324: Friday Look Back - Fear Causes Paralysis 21.11.2025

Invest Smarter Podcast  Episode 324: Friday Look Back - Fear Causes Paralysis  Host: Simon Castillo  Join our host Simon Castillo for a one on one Friday Look Back where he reflects on:  Discover the current disconnect in multi-family real estate property values due to rising interest rates. Understand why fear causes investor paralysis and the importance of continually seeking opportunities.   We...

ISP 323: Powerhouse Couple Overcoming Adversity & Building a Real Estate Portfolio 18.11.2025

Episode 323: Powerhouse Couple Overcoming Adversity & Building a Real Estate Portfolio Host: Simon Castillo  Guest: Jacqueline Landry & Melvin Landry Join our host Simon Castillo with Jacqueline Landry & Melvin Landry  as they discuss: Personal journey of entrepreneurship  Education and proximity are key  The value of alignment and mindset  The strength, energy, and love of learning to...

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