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 347: Key Metrics & Red Flags to Look for in Multifamily Investment 17.02.2026 46:41
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 13:54
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 44:48
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 18:20
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 45:48
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 16:00
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 22:11
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 36:07
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 14:22
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 42:12
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 16:51
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 39:52
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 22:16
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 43:25
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 37:08
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 18:30
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 45:22
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 8:36
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 35:28
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 7:07
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 38:28
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 11:27
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 50:51
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 10:18
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 44:25
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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