Westside Investors Network (WIN)

10 Episodes
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By: AJ and Chris Shepard

Welcome to the West Side Investors Network, WIN, your community of investing knowledge for growth. This is the Real Estate Professionals Investing Podcast. For Real Estate Professionals by Real Estate Professionals. This show is focused on the next step in your career....... investing.

165. How to Understand Commercial Sectors and Market Trajectories with Caleb David
Yesterday at 6:00 PM

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ABOUT CALEB DAVID

Caleb is the Principal of David Commercial Real Estate. Creating space for people to be seen, heard and known makes Caleb David come alive. His love for the Front Range community, partnership, and connecting with people has helped Caleb to become one of the leading brokers in the Colorado Springs market. He provides reliable expertise in office, medical, retail, industrial and land markets. As an investor and owner of commercial real estate himself, Caleb brings a unique perspective and solid advice to his local...


164. How to Protect Your Real Estate Investments with Strategic Underwriting with Sam Morris
03/26/2025

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ABOUT SAM MORRIS

 Sam is the CEO of Sunset Capital, a vertically integrated real estate investment and asset management firm based in Houston. With over 23 years of experience in real estate, he has led acquisition and disposition teams on transactions exceeding $550 million. Sam's background as a corporate banker for 18 years involved facilitating over $1B in real estate financing, equipping him with a comprehensive understanding of property lifecycle management. 

 

THIS TOPIC IN A NUTSHELL: 

Sam’s background and journey in real estate...


163. Creating Lasting Wealth: Why Asking the Right Questions Matter with Whitney Elkins-Hutten
03/19/2025

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ABOUT WHITNEY ELKINS-HUTTEN

Whitney Elkins-Hutten is the Director of Investor Education at PassiveInvesting.com, founder of Ashwealth.com, and author of the award-winning #1 bestseller Money for Tomorrow: How to Build and Protect Generational Wealth. Through her proven wealth-building framework, Whitney empowers high-earning professionals and business owners to create secure, passive income streams that support a legacy of financial freedom for generations. With over $800MM in assets—including 6,500+ residential units, 15 express car washes, and 2,200+ self-storage units—Whitney guides clients to invest strategically, helping them confidently turn a single $100,000 inve...


162. Diversifying Your Portfolio in International Markets with Anne-Michelle Wand
03/12/2025

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ABOUT  ANNE-MICHELLE WAND

International real estate expert and conscious investor.  Former single mom turned successful real estate entrepreneur who now lives in paradise on a Caribbean island in Panama debt free. Anne Michelle enjoys her life from this dream location, creating intentional investment opportunities for high earning professionals to diversify outside the USA.  

 

With over 40 years of experience in real estate investments in emerging markets including Panama, Mexico, and the USA. She currently has a company called Passive Profit Partners that makes your...


161. Breaking Misconceptions in a Competitive Market with Michael Voulgarakis
03/05/2025

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ABOUT  MICHAEL VOULGARAKIS

Michael Voulgarakis is a seasoned commercial real estate professional with over 19 years of experience in debt and equity underwriting, capital raising, and asset management. At Southgate Ventures, he has successfully acquired 26 properties, completed 18 full cycle deals in the Puget Sound region, and asset managed real estate valued at over $300M. He holds a Master's in Commercial Real Estate Finance and a Bachelor's in Business Administration, equipping him with both the academic and practical expertise to deliver results in today's market. 

 

 

TH...


160. The Truth About Private Money and Hard Money Lending in Real Estate with Jay Conner
02/26/2025

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ABOUT JAY CONNER

Jay Conner began investing in real estate in 2003. At the start of his career, he relied on his local banker and was able to put together a few deals. After years of feeling owned by the bank, he learned how to buy properties using creative financing, including subject to and using lease-options. 

 

After the market crashed in 2008, he had to abandon everything he knew about how to finance his deals. Then he heard about the world of private money. He...


159. How This Firefighter Found Success in Real Estate Investing with Dave Seymour
02/19/2025

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ABOUT DAVE SEYMOUR

Dave Seymour, a retired 16-year veteran of the Fire Service launched his Real Estate career during the last market crash, rapidly becoming one of the Countries top investors. Dave is considered a leading expert in commercial multi-family and ground-up development transactions. His success in business and Real Estate put him on the radar of A&E television network as well as multiple news organizations like CBS, ABC, CNBC,and FOX News.“FlippingBoston” aired on A & E for multiple seasons. He has helped accredited inve...


158. Land Investing 101: Spotting Great Deals and Avoiding Red Flags with Mark Podolsky
02/05/2025

ABOUT MARK PODOLSKY

Mark owns Frontier Properties, a land investment company. Mark (AKA The Land Geek) is widely considered the country’s most trusted and foremost authority on buying and selling raw, undeveloped land in the United States. 

  

Since 2001 Mark has completed over 6,000 raw land deals with an average return on investment of over 300% on cash purchases and over 1000% on land deals that he financed. Mark is the host of one of the top-rated podcasts in the Investing Category on iTunes aptly titled The Art of Passive Income Model. 

 

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157. From Closing Deals to Creating Wealth: A Broker’s Journey to Syndication with Will Matheson
01/29/2025

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ABOUT WILL MATHESON

Will Matheson is the co-founder of Matheson Capital, a real estate investment firm based in Charleston, South Carolina.  Prior to forming Matheson Capital, founders Will and Evan worked as commercial brokers for Marcus & Millichap in Raleigh, NC. In just two years, they completed over 50 investment sales transactions totaling over $200 million as a part of the region's top team.  Since the start of 2018, they have completed over 16 acquisitions, and have over $100 million of multifamily assets under management. 

 

 

 

THIS T...


156. Debunking Turnkey Investment Myths and the Truth Behind Them with Zach Lemaster
01/08/2025

ABOUT ZACH LEMASTER 

 Zach Lemaster is the founder & CEO of Rent To Retirement, the nation's leading turnkey investment company. Zach is a seasoned real estate investor and licensed broker that has accumulated a large portfolio of rental properties across multiple markets including single-family, multifamily, commercial and new construction. Zach is a licensed Optometrist who practices on a volunteer basis. 

 

Zach started investing in real estate while working as an Optometrist & Captain for the US Air Force. This eventually allowed him to retire early from his career in medicine to be a professional investor by s...