Best Simon Castillo Podcasts (2025)

1
ISP 274: Friday Look Back - How I Bought A House for $8,000 10:19

22h ago10:19

10:19

Episode 274: Friday Look Back - How I Bought A House for $8,000 Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The recent shift in investor sentiment amid ongoing economic uncertainty. How inflation and interest rate expectations are reshaping the real estate landscape. Key insights fr…

1
ISP 273: Thinking About Leaving Your W2? 8:58

4d ago8:58

8:58

Episode 273: Thinking About Leaving Your W2? Host: Simon Castillo Join our host Simon Castillo for a one-on-one episode as he reflects on: How today’s economic uncertainty is reshaping investor mindsets The hidden impacts of rising tariffs on real estate and development Why fear-based decisions can derail your investment strategy What savvy investo…

1
ISP 272: Friday Look Back - Do This to Find Your Next Deal 9:53

9d ago9:53

9:53

Episode 272: Friday Look Back - Do This to Find Your Next Deal Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The impact of economic uncertainty on real estate investment strategies. How rising tariffs are influencing investor decisions and market behavior. Shifts in buyer sentiment an…

1
ISP 271: Creating The Path To Becoming A Real Estate Syndictor 38:28

11d ago38:28

38:28

Episode 271: Creating The Path To Becoming A Real Estate Syndictor Host: Simon Castillo Guest: Jim Lee Simon Castillo is joined by Jim Lee to 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 Netw…

1
ISP 270: Friday Look Back - Fed Pauses on Rates Again; What it Means 10:33

16d ago10:33

10:33

Episode 270: Friday Look Back - Fed Pauses on Rates Again; What it Means Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The latest developments in economic uncertainty and what they mean for investors. The lingering impact of tariffs and international trade dynamics. How real estate pr…

1
ISP 269: The Mistake Beginning Investors Should Avoid 8:39

19d ago8:39

8:39

Episode 269: The Mistake Beginning Investors Should Avoid Host: Simon Castillo Join our host Simon Castillo for a one-on-one episode as he reflects on: Navigating uncertainty in today’s real estate market. How rising tariffs impact investor confidence. Key strategies to stay resilient during economic shifts. Lessons learned from past market cycles.…

1
ISP 268: Friday Look Back - 5 Ways Your Rental is Leaking Cash 11:20

23d ago11:20

11:20

Episode 268: Friday Look Back - 5 Ways Your Rental is Leaking Cash Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The five silent ways your rental property might be leaking cash — and how to fix them. What turns a once-promising asset into an “alligator property” devouring your profits…

1
ISP 267: Signs Your Contractor May Be Going Under 8:27

26d ago8:27

8:27

Episode 267: Signs Your Contractor May Be Going Under Host: Simon Castillo Join our host Simon Castillo for a one-on-one episode as he reflects on: How shifting economic tides and uncertainty are shaping investor sentiment The real impact of tariffs on global markets and local business decisions Navigating fear, risk, and opportunity in today’s rea…

1
ISP 266: Friday Look Back - Slower Is Faster in Real Estate Investing 11:28

1M ago11:28

11:28

Episode 266: Friday Look Back - Slower Is Faster in Real Estate Investing Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Why moving slower in real estate can actually lead to faster, more sustainable success How the "tortoise vs. hare" mindset applies to building long-term wealth The p…

1
ISP 265: Take Decisive Action to Overcome Analysis Paralysis 10:17

1M ago10:17

10:17

Episode 265: Take Decisive Action to Overcome Analysis Paralysis Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Understanding Analysis Paralysis The Power of Mindset The Offer as a Starting Point Strategic Pessimism Embracing Failure as Data We have open investment opportunities. Want to learn more? Ch…

1
ISP 264: Friday Look Back - Economic Uncertainty, Tariffs and Real Estate Investors 9:17

1M ago9:17

9:17

Episode 264: Friday Look Back - Economic Uncertainty, Tariffs and Real Estate Investors Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Tariffs Are Spiking Costs – Steel, lumber, and key materials are up 15–20% overnight. Delays & Vacancies Rising – Supply chain hiccups and hesitant buy…

1
ISP 263: How to Start Raising Capital 12:08

1M ago12:08

12:08

Episode 263: How to Start Raising Capital Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Discover a powerful shift in how investors approach opportunities. Learn why mindset may be the biggest obstacle to growth. Uncover the often-overlooked skill that separates average from exceptional. Explore how lo…

1
ISP 262: Friday Look Back - Fear Causes Paralysis 10:18

2M ago10:18

10:18

Episode 262: Friday Look Back - Fear Causes Paralysis Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The gap between what property sellers believe their properties are worth and what buyers can realistically pay is growing. The Federal Reserve’s ongoing increases in interest rates pose…

1
ISP 261: Building a Vertically Integrated Real Estate Business 50:51

2M ago50:51

50:51

Episode 261: Building a Vertically Integrated Real Estate Business Host: Simon Castillo Guest: Mark Updegraff Join our host Simon Castillo and Mark Updegraff as they reflect on: 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 Scal…

1
ISP 260: Five Ways You Can Find Off Market Deals 14:19

2M ago14:19

14:19

Episode 260: Five Ways You Can Find Off Market Deals Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Effective methods for uncovering off-market opportunities The Role of Networking in Real Estate Building a strong network in real estate can lead to exclusive deal opportunities. The necessity of develop…

1
83 - Kelvin Lymer in Worcestershire, England 44:39

2M ago44:39

44:39

In this new podcast episode I talked to an old friend Kelvin Lymer about many interesting hoof-care topics. We also discussed the ethics of endurance events, getting stranded in the desert, glue shoes, 3D printing, apprentices and much more. Thank you to our sponsor The Hoofcare Essentials Foundation, and their affiliated partners. You can find mor…

1
ISP 259: Friday Look Back - Unlocking The Power of Off Market Deals 13:33

2M ago13:33

13:33

Episode 259: Friday Look Back - Unlocking The Power of Off Market Deals Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: What are off market deals and how can you find them? The Importance of Seller Relationships Tailoring communications to specific demographics, like absentee owners or …

1
ISP 258: Why Are Mortgage Rates Falling? 6:54

2M ago6:54

6:54

Episode 258: Why Are Mortgage Rates Falling? Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: The direction that mortgage rates are headed. The Relationship Between Mortgage Rates and Treasury Yields Investor Sentiment Amid Economic Concerns Impact of Declining Consumer Spending Opportunities in Real Est…

1
ISP 257: Friday Look Back -What's Your Personal Investment Strategy? 10:53

3M ago10:53

10:53

Episode 257: Friday Look Back -What's Your Personal Investment Strategy? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Choosing your personal investment strategy. Your investment strategy should be customized to meet your individual needs. How can you design a strategy that works for …

1
ISP 256: Finding Hidden Multifamily Opportunities with Andrea Foley 56:08

3M ago56:08

56:08

Episode 256: Finding Hidden Multifamily Opportunities with Andrea Foley Host: Simon Castillo Guest: Andrea Foley Join our host Simon Castillo with Andrea Foley episode as they reflects on: Buying hotels and converting to multifamily Solutions for affordable housing We have open investment opportunities. Want to learn more? Check out www.sastexascap…

1
ISP 255: Friday Look Back - Mailbag: Long & Short Term Investing Strategies 10:58

3M ago10:58

10:58

Episode 255: Friday Look Back - Mailbag: Long & Short Term Investing Strategies Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The differences between buy and hold investing and buy and hold turnkey properties. The distinction between active and passive real estate investing strategies…

1
ISP 254: Proven Leasing Strategies For When Your Property Won't Rent 13:39

3M ago13:39

13:39

Episode 254: Proven Leasing Strategies For When Your Property Won't Rent Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Ensuring properties are rent-ready with great curb appeal is crucial for attracting tenants. Conducting detailed market analyses helps in setting competitive rental prices and underst…

1
ISP 253: Friday Look Back - 5 Tips For Beginning Investors 12:32

3M ago12:32

12:32

Episode 253: Friday Look Back - 5 Tips For Beginning Investors Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Having a growth mindset. Picking a strategy that fits your goals. You have to take action and learn from experience. Have a trusted coach and mentor. You have to build the righ…

1
ISP 252: Have You Considered Building Vs Buying? 12:19

3M ago12:19

12:19

Episode 252: Have You Considered Building Vs Buying? Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Is it better to buy or build property right now? There is a larger profit potential when you engage in ground-up development. You'll never know what you are going to find after buying a property. Be awar…

1
82 - Kit Miller at the International Hoof Care Summit 2024 37:59

3M ago37:59

37:59

Thank you to our sponsor The Hoofcare Essentials Foundation, and their affiliated partners. You can find more information on the HEF website www.hoofcareessentials.com Find me on Facebook & Instagram @drsimoncurtisMy website can be found drsimoncurtis.comSubscribe to my Youtube channel: youtube.com/drsimoncurtisThe Hoof of the Horse is a hoof care …

1
ISP 251: Friday Look Back - The Biggest Barrier to Getting Started: Fear! 11:30

3M ago11:30

11:30

Episode 251: Friday Look Back - The Biggest Barrier to Getting Started: Fear! Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Fear of the Unknown The journey often begins with small, manageable investments, such as buying a duplex or a single-family home. While self-learning is valuable…

1
ISP 250: Having a Coach or Mentor Alongside You 37:43

3M ago37:43

37:43

Episode 250: Having a Coach or Mentor Alongside You Host: Simon Castillo Guests: Brian Head & Chris Gordon Join our host Simon Castillo with Brian Head & Chris Gordon as they discuss on: The value of education, coaching, and having the right mindset. What makes real estate investors successful. How do you overcome the sense of being overwhelmed and…

1
ISP 249: Friday Look Back - Why Real Estate Investing? 10:34

4M ago10:34

10:34

Episode 249: Friday Look Back - Why Real Estate Investing? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Why do we invest in real estate? What is your motivation for wanting to invest in real estate? What are you investing in real estate? Real estate offers a path to financial freedom…

1
ISP 248: Investment Advice with Yonah Weiss 38:48

4M ago38:48

38:48

Episode 248: Investment Advice with Yonah Weiss Host: Simon Castillo Guest: Yonah Weiss Join our host Simon Castillo for a one on one episode as he reflects on: Abundance Mindset Cost Segregation Bonus Depreciation Passive Investing Overcoming limiting beliefs Stick with your principles We have open investment opportunities. Want to learn more? Che…

1
ISP 247: Friday Look Back - Invest Confidently! 7:32

4M ago7:32

7:32

Episode 247: Friday Look Back - Invest Confidently! Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Understanding fear is crucial for real estate investing success. Knowledge reduces fear and boosts confidence in decision-making. Smart investors manage, not eliminate, risk. Setbacks in …

1
ISP 246: Overcoming Analysis Paralysis and Taking Action 22:18

4M ago22:18

22:18

Episode 246: Overcoming Analysis Paralysis and Taking Action Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Analysis Paralysis Ready - aim aim aim aim aim – are you taking a shot? Sometimes it takes a while to gain momentum Be sure not to take advice from the wrong individuals Your business doesn’t hav…

1
ISP 245: Friday Look Back - Are You Ever Too Old To Invest In Real Estate? 10:20

4M ago10:20

10:20

Episode 245: Friday Look Back - Are You Ever Too Old To Invest In Real Estate? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Age might bring different challenges, but it also offers some unique opportunities. Discipline; focus on the manageable and low risk deals that are aligned with…

1
ISP 244: Remote Real Estate Investing Strategies with Jen & Stacy Conkey 50:24

4M ago50:24

50:24

Episode 244: Remote Real Estate Investing Strategies with Jen & Stacy Conkey Host: Simon Castillo Join our host Simon Castillo with Jen & Stacy Conkey as they discuss on: “Real Estate is that thing that I want to do.” What is a joint venture and how do you structure that project? I lost $80,000 in one single day Don’t go that fast, stay with your f…

1
81 - Garrett Ford at the International Hoof Care Summit 2024 46:09

4M ago46:09

46:09

This one is for all the gluers out there. I had a great conversation with Garrett Ford at the last IHCS, and of course like in all of my podcasts, we cover many other topics As I now head out for the 2025 Summit I look forward to having many more interesting conversations like this one.Thank you to our sponsor The Hoofcare Essentials Foundation, an…

1
ISP 243: Friday Lookback - Overcoming Imposter Syndrome 9:08

4M ago9:08

9:08

Episode 243: Friday Look Back - Overcoming Imposter Syndrome Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: What exactly is imposter syndrome? Numbers and comparison are one of the unique challenges in real estate. Embracing the discomfort and using it as fuel to grow. Instead of tryin…

1
80 - David Hallock at the International Hoof Care Summit 2024 44:21

4M ago44:21

44:21

With the IHCS 2025 approaching, I wanted to share this conversation I had with with David Hallock at the last one, to learn more about his life and work, as well as his research into the digital cushion. David also has taken almost every possible farrier exam out there, so it was interesting to hear all about that too.Thank you to our sponsor The H…

1
ISP 242: What to Know About Cash Flow As An Investor 12:33

4M ago12:33

12:33

Episode 242: What to Know About Cash Flow As An Investor Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Misconception about cash flow. How you can proactively protect your investment. How you can optimize and protect your cash flow. Maintaining cash flow and having a cash reserve are essential for a re…

1
ISP 241: Friday Look Back - Is Flipping Properties The Right Strategy For You? 10:20

5M ago10:20

10:20

Episode 241: Friday Look Back - Is Flipping Properties The Right Strategy For You? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Is flipping properties the right path for you? Flipping is most effective when several key factors are aligned. Flipping is more like running a manufacturin…

1
ISP 240: Top Real Estate Trends to Watch For in 2025 10:05

5M ago10:05

10:05

Episode 240: Top Real Estate Trends to Watch For in 2025 Host: Simon Castillo Join our host Simon Castillo for a one on one episode as he reflects on: Emerging trends for real estate investors The Federal Reserve’s approach to interest rates is tied closely to inflation indicators, and while rate cuts may occur, they will depend on the inflation tr…

1
ISP 239: Friday Look Back - Building a Vertically Integrated Real Estate Business 50:51

5M ago50:51

50:51

Episode 239: Friday Look Back - Friday Look Back - Building a Vertically Integrated Real Estate Business Host: Simon Castillo Guest: Mark Updegraff Join our host Simon Castillo with 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 master…

1
ISP 238: The Surprising Lucrative Real Estate Asset Class with Stewart Heath 44:28

5M ago44:28

44:28

Episode 238: The Surprising Lucrative Real Estate Asset Class with Stewart Heath Host: Simon Castillo Guest: Stewart Heath Join our host Simon Castillo with Caleb Johnson as they discuss: Real estate is a constant in our lives Outlook for office real estate The Debt Wall Rate cuts Multifamily Meltdown Opportunities in multifamily to come The Tennes…

1
ISP 237: Friday Look Back - Looking back at 2024, Looking Forward to 2025 13:32

5M ago13:32

13:32

Episode 237: Friday Look Back - Looking back at 2024, Looking Forward to 2025 Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Starting doesn't mean you have to know everything or that you have to have all the answers, it means committing to the journey. Taking the first step no matter h…

1
ISP 236: Friday Look Back - Strategies vs Tactics For Real Estate Investors 10:22

5M ago10:22

10:22

Episode 236: Friday Look Back - Friday Look Back - Strategies vs Tactics For Real Estate Investors Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: What it takes to understand the difference between having a strategy and a tactic. Strategy is your big-picture plan. Tactics behind the str…

1
79 - Esco Buff at the International Hoof Care Summit 2024 46:59

5M ago46:59

46:59

In this episode I sat down with Esco Buff, a farrier who is both a doctorate and a minister. We talk about radiography, his studies on fescue toxicity, passing on old knowledge to new farriers, limb length disparity, plus his work with camels, eagles, turtles and a whole host of other animals. We spoke about so many topics, there’s too much to list…

1
ISP 235: How Can The Busy W2 Professional Get Started In Real Estate? 41:57

5M ago41:57

41:57

Episode 235: How Can The Busy W2 Professional Get Started In Real Estate? Host: Simon Castillo Guest: Dan Calonge Join our host Simon Castillo with Caleb Johnson as they discuss: Multifamily is a team sport Balancing a W2 with being an investor Giving back The importance of aligning values We have open investment opportunities. Want to learn more? …

1
ISP 234: Friday Look Back - Mailbag Episode: Should You Buy A Cheap Property? 11:32

5M ago11:32

11:32

Episode 234: Friday Look Back - Mailbag Episode: Should You Buy A Cheap Property? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Knowing your market is crucial. Properties deemed “cheap” can lead to poor investment outcomes if they lack demand. Always analyze local trends. Investing in…

1
ISP 233: Overcoming Limiting Beliefs and Taking Action to Achieve Your Goals 37:08

6M ago37:08

37:08

Episode 232: Overcoming Limiting Beliefs and Taking Action to Achieve Your Goals Host: Simon Castillo Guest: Caleb Johnson Join our host Simon Castillo with Caleb Johnson as they discuss: Family Hardships House Hacking Setting goals that stretch you, but are still realistic Taking action If you’re a passive investor, be okay with walking away from …

1
ISP 232: Friday Look Back - Traits Successful Real Estate Investors Have In Common 15:31

6M ago15:31

15:31

Episode 232: Friday Look Back - Traits Successful Real Estate Investors Have In Common Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The common traits that set successful real estate investors apart from the people that dabble. Overcoming analysis paralysis is crucial; taking the firs…

1
ISP 231: From Being in Debt to Building Wealth with Tim Little 46:01

6M ago46:01

46:01

Episode 231: From Being in Debt to Building Wealth with Tim Little Host: Simon Castillo Guest: Tim Little Join our host Simon Castillo for a one on one episode as he reflects on: Tenant experiences Structuring the 1031 Exchange Tax strategies Overcoming student debt and growing financially as an investor Building up a network and reputation as an o…

1
ISP 230: Friday Look Back - Black Friday: Strategies That Can Help Grow Your Real Estate Portfolio 9:31

6M ago9:31

9:31

Episode 230: Friday Look Back - Black Friday: Strategies That Can Help Grow Your Real Estate Portfolio Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Growing a real estate portfolio requires strategic planning and goal-setting, especially at the year’s end. Utilizing 1031 exchanges can…

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