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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

16:51

isp 337: Friday Look Back - How to NOT Lose Money in...

Invest Smarter Podcast ·

2026/01/09

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 todayReal Estate is a ‘get wealthy slow game’ The powerful impact of joining a community We have open i...

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39:52

ISP 336: From RV Parks to Multifamily: Passively...

Invest Smarter Podcast ·

2026/01/07

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 healthy business partnerships Surrounding yourself with like m...

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22:16

ISP 335: Friday Look Back - 5 Principles You Need to...

Invest Smarter Podcast ·

2026/01/02

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 relationshipsEstablish a strong track record for managing investment capitalAlign investor principles with project timeline We have open investment opportunities. W...

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43:25

ISP 334: Persevering in Real Estate as a Vietnamese...

Invest Smarter Podcast ·

2025/12/30

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. Want to learn more? Check out www.sastexascapital.comDownload our FREE E...

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37:08

ISP 333: Overcoming Limiting Beliefs and Taking...

Invest Smarter Podcast ·

2025/12/23

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.sastexascapital.comDownload our FREE E-Book - Multifamily Millions - www.sast...

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18:30

ISP 332: Friday Look Back - Questions Investors Need...

Invest Smarter Podcast ·

2025/12/19

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 moneyBeing properly capitalizedUnderstanding who the property manager is and understanding who the asset manager is We have open investm...

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45:22

ISP 331: How to Grow Your Social Media Brand

Invest Smarter Podcast ·

2025/12/16

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 businessImposter 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 female in the real estate industry The connection b...

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8:36

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

Invest Smarter Podcast ·

2025/12/12

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 open investment opportunities. Want to learn more? Check out ...

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35:28

ISP 329: From Japan to Corporate America to Building...

Invest Smarter Podcast ·

2025/12/09

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 StorageDiversificationWe have open investment opportunities. Want to learn more? Check out www.sastexascapital.comDownload our FREE E-Book - Multifamily Millions...

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7:07

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

Invest Smarter Podcast ·

2025/12/05

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 collaborativeHow can you lift others up? Bring others with you on your journey to...

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38:28

ISP 327: Creating The Path To Becoming A Real Estate...

Invest Smarter Podcast ·

2025/12/02

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 real estate industry The value of mentorship and masterminds...

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11:27

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

Invest Smarter Podcast ·

2025/11/28

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 grow your network Grow your network, grow your education&nbs...

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50:51

ISP 325: Building a Vertically Integrated Real Estate...

Invest Smarter Podcast ·

2025/11/25

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 careerBuilding a business Finding people that you resonate with and asking questions Joining a mastermind and expanding your networkScaling your growing real estate business Gross Rent Multipliers Shifts in the housing industry Learning how to regain...

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10:18

ISP 324: Friday Look Back - Fear Causes Paralysis

Invest Smarter Podcast ·

2025/11/21

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 have open investment opportunities. Want to learn more? Check out www...

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44:25

ISP 323: Powerhouse Couple Overcoming Adversity &...

Invest Smarter Podcast ·

2025/11/18

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 together within a mastermind groupWe have open investment opportunit...

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11:03

ISP 322: Friday Look Back - What Ted Lasso Can Teach...

Invest Smarter Podcast ·

2025/11/14

Episode 322: Friday Look Back - What Ted Lasso Can Teach Us About Real Estate Investing Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: 7 Real Estate Lessons from watching Ted LassoWe have open investment opportunities. Want to learn more? Check out www.sastexascapital.comDownload our FREE E-Book - Multifamily Millions - www.sastexascapital.com On the second wednesday of every month, we have the Wealth and ...

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56:08

ISP 321:Finding Hidden Multifamily Opportunities with...

Invest Smarter Podcast ·

2025/11/11

Episode 321: Finding Hidden Multifamily Opportunities with Andrea Foley Host: Simon Castillo Guest: Andrea Foley Join our host Simon Castillo and Andrea Foley as they discuss: Buying hotels and converting to multifamily Solutions for affordable housing We have open investment opportunities. Want to learn more? Check out www.sastexascapital.comDownload our FREE E-Book - Multifamily Millions - www.sastexascapital.com On the second wednesday of eve...

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11:03

ISP 320: Friday Look Back - What Ted Lasso Can Teach...

Invest Smarter Podcast ·

2025/11/07

Episode 320: Friday Look Back - What Ted Lasso Can Teach Us About Real Estate Investing Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: 7 Real Estate Lessons from watching Ted LassoWe have investment opportunities open and available NOW! www.sastexascapital.com - Sign up for our newsletter to be notified when we have investment opportunities available Download our FREE report on why multifamily investing mak...

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47:52

ISP 318: Owning Your Future By Taking Your Skills and...

Invest Smarter Podcast ·

2025/11/04

Episode 318: Owning Your Future By Taking Your Skills and Knowledge To The Next Level with Adam Carswell Host: Simon Castillo Guest: Adam Carswell Join our host Simon Castillo and Adam Carswell as they discuss: Raisemasters; Raising Capital misconception - “If you find a great deal, the money will follow.” Do you agree? The value of expanding your network through education; Building your business infrastructure; Leveraging your network with social media;&nbs...

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13:20

ISP 318: Friday Look Back - 4 Tips to Create...

Invest Smarter Podcast ·

2025/10/31

Episode 313: Friday Look Back - 4 Tips to Create Disciplined Habits That Lead to Sustaining the Best Version Of Yourself Host: Simon Castillo Join our host Simon Castillo as he reflects: The power of building wealth through real estate and how to achieve financial freedom via multi-family investing. Tips on real estate investing, entrepreneurship, business, and even mindset. Four ways to become more disciplined and create habits for a better version of yourself: c...

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337 results

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