Best Simon Castillo Podcasts (2025)

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ISP 237: Friday Look Back - What Do Successful Individuals Do? 8 Strategies To Get This Right! 16:14

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1h ago16:14

16:14

Episode 237: Friday Look Back - What Do Successful Individuals Do? 8 Strategies To Get This Right! Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back where he reflects on: Learn why waking up early, reading, and exercising are non-negotiable for success. Discover how writing down your goals and finding mentors can d…

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ISP 236: If You Master Yourself, You Will Master The Market 43:35

2d ago43:35

43:35

Episode 236: If You Master Yourself, You Will Master The Market Host: Simon Castillo Guest: Jerremy Alexander Newsome Join our host Simon Castillo and Jerremy Alexander Newsome as they discuss: That was a 34 million dollar mistake Beginning the entrepreneurship journey at a young age Fail with as many people watching as possible. Fail, as big as yo…

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ISP 235: Friday Look Back - Angel Investing 101 & Could it Be Right For You? 18:01

2h ago18:01

18:01

Episode 235: Friday Look Back - Angel Investing 101 & Could it Be Right For You? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: What angel investing is and how it works. The risks vs. rewards of backing early-stage startups. How angel investing compares to real estate opportunities. Is…

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ISP 234: How Can The Busy W2 Professional Get Started In Real Estate? 41:57

33m ago41:57

41:57

Episode 234: How Can The Busy W2 Professional Get Started In Real Estate? Host: Simon Castillo Guest: Dan Calonge Join our host Simon Castillo and Dan Calonge 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? Che…

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ISP 233: Friday Look Back - Momentum: How Do You Create It & How Do You Sustain It? 13:24

4d ago13:24

13:24

Episode 233: Friday Look Back - Momentum: How Do You Create It & How Do You Sustain It? Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: How can you find momentum? What does it feel like to have momentum? We have open investment opportunities. Want to learn more? Check out www.sastexasca…

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ISP 232: Investing In Yourself Is Key 45:22

7d ago45:22

45:22

Episode 232: There Couldn’t Be A Better Time To Be An Entrepreneur Host: Simon Castillo Guest: George Salas Join our host Simon Castillo and Nir Wittenberg as the discuss: Changing mindset and beliefs Getting to the point of needing something different in life Identifying markets and properties Defining arbitrage Reflecting on the effects of the Co…

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ISP 231: Friday Look Back - Investment Strategies That WORK! 15:31

11d ago15:31

15:31

Episode 231: Friday Look Back - Investment Strategies That WORK! Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: If you focus on value, you will always benefit from growth when growth happens Value investing What is a good deal in real estate? There are 3 buckets that investing and real…

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ISP 230: Passive Real Estate Investing Is Truly Magical, The Wealth That Passive Real Estate Investing Can Create For Families Is Life Changing 45:23

24d ago45:23

45:23

Episode 230: Passive Real Estate Investing Is Truly Magical, The Wealth That Passive Real Estate Investing Can Create For Families Is Life Changing Host: Simon Castillo Guest: Angie Aki Join our host Simon Castillo and Angie Aki as the discuss: Immense growth from wholesaling in real estate Set goals and be very clear about the desired outcome of t…

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ISP 229: Friday Look Back - Why Multifamily Investing Makes Sense 15:06

18d ago15:06

15:06

Episode 229: Friday Look Back - Why Multifamily Investing Makes Sense Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: If I could give the younger version of myself one piece of advice, it would be… You have to have some capital to begin investing in real estate Education is key We have …

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ISP 298: Industrial Real Estate In Inflationary & Recessionary Times 35:51

24d ago35:51

35:51

Episode 298: Industrial Real Estate In Inflationary & Recessionary Times Host: Simon Castillo Guest: David Cruz-Palmer Join our host Simon Castillo and David Cruz-Palmer as they discuss: Triple net leases Bonus Depreciation Are we in a recession? Industrial real estate in inflationary and recessionary times We have open investment opportunities. Wa…

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ISP 297: Friday Look Back - The Best Way To Get Started, Is To Get Educated 15:53

25d ago15:53

15:53

Episode 297: Friday Look Back - The Best Way To Get Started, Is To Get Educated Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Understanding what a real estate investment trust is. Investing in real estate without owning property Earning passive income through dividends We have open in…

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84 - Mitch Taylor & Gavin Moody in Türkiye 55:30

1M ago55:30

55:30

I recorded this podcast with Mitch Taylor and Gavin Moody in Türkiye while we had a little road trip to celebrate the end of the first exams at the farrier school they worked hard together to set up with the Turkish Jockey Club. We discuss exactly how do you teach farriery to a group of men who mostly do not speak English and have never worked with…

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ISP 296: True Wealth Is Made During A Recession 44:13

1M ago44:13

44:13

Episode 296: True Wealth Is Made During A Recession Host: Simon Castillo Guest: Max Gonzales Join our host Simon Castillo and Max Gonzales as they discuss: Multifamily is a team sport Should I wait to invest? Buy low, sell high It wasn’t a real estate crash, it was a liquidity crisis The more assets you have, the more playing cards that you have It…

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ISP 295: Friday Look Back - Understanding What A Real Estate Investment Trust Is (REIT) 15:06

1M ago15:06

15:06

Episode 295: Friday Look Back - Understanding What A Real Estate Investment Trust Is (REIT) Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Understanding what a real estate investment trust is. Investing in real estate without owning property Earning passive income through dividends We …

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ISP 294: Key Benefits Of Running A Multifamily Business 41:44

2M ago41:44

41:44

Episode 294: Key Benefits Of Running A Multifamily Business Host: Simon Castillo Guest: Michael Piehler Join our host Simon Castillo and Michael Piehler as they discuss: Difference between working in the stock market and working in real estate Key benefits of running a multifamily business This thing called passive income’ There is such a thing as …

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ISP 293: Friday Look Back - How The Wealthy Use Debt To Become Wealthier 12:18

2M ago12:18

12:18

Episode 293: Friday Look Back - How The Wealthy Use Debt To Become Wealthier Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Black Friday Differences between good debt and bad debt Isn’t debt risky? Using debt the right way can lead to compounding assets Always invest in yourself We hav…

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ISP 292: Do You Want To Be A Real Estate Investor Or Do You Want To Start A Real Estate Investing Company? 41:56

2M ago41:56

41:56

Episode 292: Do You Want To Be A Real Estate Investor Or Do You Want To Start A Real Estate Investing Company? Host: Simon Castillo Guest: Brian Alfaro Join our host Simon Castillo and Brian Alfaro as they discuss: The reality of starting in residential real estate Property Rehabilitation Transitioning from single family to multifamily Get your min…

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ISO 291: Friday Lookback - Once You Become An Active Syndicator - You’re Signing Up For A Very Different Life 57:06

2M ago57:06

57:06

Episode 291: Friday Lookback - Once You Become An Active Syndicator - You’re Signing Up For A Very Different Life Host: Simon Castillo Guest: Saket Jain Join our host Simon Castillo and Saket Jain for as the discuss: You don’t have to leave your W2 job to build generational wealth Should everyone become an investor? Once you become an active syndic…

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ISP 290: There Couldn’t Be A Better Time To Be An Entrepreneur 29:45

2M ago29:45

29:45

Episode 290: There Couldn’t Be A Better Time To Be An Entrepreneur Host: Simon Castillo Guest: Nir Wittenberg Join our host Simon Castillo and Nir Wittenberg as they discuss: Achieving a passive income lifestylethey Positioning yourself to be focused on the returns; part of real estate The value of utilizing systems Celebrate all of your ‘wins’ We …

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ISP 289: Friday Look Back - THIS Is How You Build A Bulletproof Mindset 11:27

2M ago11:27

11:27

Episode 289: Friday Look Back - THIS Is How You Build A Bulletproof Mindset Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Fear is a big part of mindset How do you build a bulletproof mindset How do you protect and build confidence We have open investment opportunities. Want to learn m…

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ISP 288: The Power Of Tax Benefits In Real Estate Investing 46:42

2M ago46:42

46:42

Episode 288: The Power Of Tax Benefits In Real Estate Investing Host: Simon Castillo Guest: K Trevor Thompson Join our host Simon Castillo and K Trevor Thompson as they discuss: The power of networking How to monitor your investments and what to do when a deal isn’t advertised well The power of tax benefits in real estate investing The Compound Eff…

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ISP 287: Educate Yourself and Take Action 43:43

2M ago43:43

43:43

Episode 287: Educate Yourself and Take Action Host: Simon Castillo Guest: Matt Hansen Join our host Simon Castillo and Matt Hansen to discuss: Leaving corporate America and entering real estate Difference between investing in multifamily vs single family The importance of vetting your sponsor Being a General Partner is not for everyone The differen…

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ISP 286: Real Estate Is The Best Vehicle For Taking Financial Control Of Your Life 38:21

2M ago38:21

38:21

Episode 286: Real Estate Is The Best Vehicle For Taking Financial Control Of Your Life Host: Simon Castillo Guest: John Pearl Join our host Simon Castillo and John Pearl as they discuss: Trading time for money Freedom Investor Radio Communication is key Start storing money to invest it Stay focused on your long term goals Keep your ‘why’ in the fro…

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ISP 285: Wealthy Doctor Secrets with TJ Visiodei 39:09

3M ago39:09

39:09

Episode 285: Wealthy Doctor Secrets with TJ Visiodei Host: Simon Castillo Guest: TJ Visiodei Join our host Simon Castillo and TJ Visiodei to discuss: : The difference between being rich and wealthy Attracting the right people for the right deals We have open investment opportunities. Want to learn more? Check out www.sastexascapital.com Download ou…

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ISP 284: Friday Look Back - 2 Skills YOU NEED On Your Journey To Building Wealth 15:23

3M ago15:23

15:23

Episode 284: Friday Look Back - 2 Skills YOU NEED On Your Journey To Building Wealth Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Current deals at SAS Texas Capital Hurricane Ian The infinite value of building your skills and acquiring your education The significance of investing in …

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ISP 283: Start With The End In Mind 37:00

3M ago37:00

37:00

Episode 283: Start With The End In Mind Host: Simon Castillo Guest: Sandhya Seshadri Join our host Simon Castillo and Sandhya Seshadri to discuss: : Achieving the role of Lead Sponsor in a deal Being an active / passive investor The value of investing in relationships Agency debt coming back in a huge way Individuals who invest based on emotion If …

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ISP 282: Friday Lookback - How To Get Started In Real Estate Investing With Enough Capital To Match Your Budget 18:29

3M ago18:29

18:29

Episode 282: Friday Lookback - How To Get Started In Real Estate Investing With Enough Capital To Match Your Budget Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: Due Diligence How to get started in real estate investing Hos can I get started in real estate and the stock market? 95% wi…

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ISP 281: Taking Action and Failing Forward 38:13

3M ago38:13

38:13

Episode 281: Taking Action and Failing Forward Host: Simon Castillo Guest: Jeffrey Donis Join our host Simon Castillo and Jeffrey Donis to discuss: Living your dream Overcoming analysis paralysis Wholesaling in real estate Taking action and failing forward We have open investment opportunities. Want to learn more? Check out www.sastexascapital.com …

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ISP 280: Friday Look Back - Fix & Flips vs Passive Real Estate Investing: Which Is Right For You? 13:54

3M ago13:54

13:54

Episode 280: 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 involve…

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ISP 279: Building a Single Family Property Business 45:48

3M ago45:48

45:48

Episode 279: Building a Single Family Property Business Host: Simon Castillo Guest: Bill Lockhart Join our host Simon Castillo with Bill Lockhart 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…

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ISP 278: Friday Look Back - A Day in the Life of A Real Estate Investor 13:54

4M ago13:54

13:54

Episode 278: Friday Look Back - A Day in the Life of A Real Estate Investor Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The defensive improvement the Spurs showed during their recent games. Key performances from rising stars like Victor Wembanyama. The team’s growth and maturity as …

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ISP 277: How Do You Value Money? 10:25

4M ago10:25

10:25

Episode 277: How Do You Value Money? Host: Simon Castillo Join our host Simon Castillo with Jim Lee to as they discuss: How interest rate volatility is shaping investor sentiment in today’s market, The growing uncertainty around tariffs and their ripple effects across industries, Why real estate investors are reassessing risk in light of global eco…

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ISP 276: Friday Look Back - Lawsuit Risk & How to Protect Yourself 10:05

4M ago10:05

10:05

Episode 276: Friday Look Back - Lawsuit Risk & How to Protect Yourself Host: Simon Castillo Join our host Simon Castillo for a one on one Friday Look Back episode as he reflects on: The hidden legal risks that can derail even the most well-run real estate ventures. Real-life lawsuits that reveal how one misstep can cost investors millions. Practica…

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ISP 275: Creating The Path To Becoming A Real Estate Syndictor 38:28

4M ago38:28

38:28

Episode 275: Creating The Path To Becoming A Real Estate Syndictor Host: Simon Castillo Join our host Simon Castillo with Jim Lee to 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 Netwo…

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

4M 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…

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

4M 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…

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

4M 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…

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

4M 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…

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

4M 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…

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

5M 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.…

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

5M 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…

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

5M 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…

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

5M 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…

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

5M 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…

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Creator Ben Conley on Editing & Sound Design of Mango: Dead Serious Audio Drama 10:17

5M ago10:17

10:17

Creator Ben Conley dives deep into the editing and sound design of the action-packed audio drama “Mango: Dead Serious”. From layering immersive soundscapes to overcoming overwhelming post-production challenges, he’ll walk you through how the world of MANGO was brought to life through audio! Watch on YouTube Learn more at www.hard90productions.com I…

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

5M 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…

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ISP 263: How to Start Raising Capital 12:08

5M 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…

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

6M 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…

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

6M 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…

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Creator Ben Conley on Production & Recording of Mango: Dead Serious Audio Drama 12:43

5M ago12:43

12:43

Go behind the scenes of the action-packed audio drama “Mango: Dead Serious”! In this video, I talk about the production process on this DIY audio project from the ground up — including the recording process, working with voice actors and what challenges I faced. If you're curious about how audio dramas are made, want to learn more about indie story…