From Farm to Commercial Real Estate | Chip Chapin | Investors Therapy Session #2

Chip Chapin, a kind-looking bespectacled older man with happy eyes and a nicely-kept beard smiles earnestly into the camera in front of a wall of wooden cabinets enclosing several orderly rows of books. A headset that includes a pair of headphones and a microphone sits atop Chip Chapin's balding head as he speaks about his investing experiences to his interviewer Jordan Thibodeau using an internet video-chat service.
Chip Chapin being interviewed by Jordan Thibodeau for Investors Therapy

In the latest episode of Investors Therapy, Jordan chats with Chip Chapin, a tech employee–turned–investor, about his family’s experience with the Great Depression, selling the family farm, working with commercial real estate, and much more! Stay tuned for the second half of the interview to hear the full breadth of knowledge both men have to offer.

In this talk, you’ll learn about:

  • Chip’s family’s real estate history
  • How this history influenced his investment decisions
  • How Chip used his mistakes to make future profit
  • The complications within partnerships
  • Insight on leasing and leasing agents
  • Chip’s methodology on how to approach real estate
  • Emotional traps that held Chip back and how to mitigate them
  • And a ton of essential tips on how to become a successful investor!
Jordan Thibodeau Interviews Chip Chapin on Episode 2 of Investors Therapy

Notes from the Talk:

1:57: Chip’s Career and Investment Background

5:19: Chip’s Family’s Experience with Real Estate and The Great Depression

8:35: How to Mitigate Loss of Cash Flow Within Speculative Investments

10:51: Apartment Investment Issues and Complications

14:57: Chip’s First Investment Experience

19:22: Selling at a Loss and the Write Off Benefits 

23:00: Chip’s Shared Family Farm Experience

26:26: Managing Property with Multiple Owners 

30:54: How Partnerships Operate

32:57: The Trouble with Tenants in Common

36:36: What Triple Net Means and Examples

41:01: What is Cap Rate and Examples

44:28: Benefits and Disadvantages of a Ground Lease

47:37: Conservative vs Aggressive Ideology Toward Investment

49:35: How Chip Chose Deals

53:59: Multiple Tenants vs Single Tenant Deals

55:59: Importance of a Property Manager

59:54: How Commercial Leasing Agent and Leasing Works

1:04:35: How Chip Negotiated Leases

1:10:42: Emotional Traps: Emotional Checks and Investment Journals 

Related Links:

New Laws Affecting the CA Rental Market

Real Estate Investors Toolbox

Investors Therapy Episode #1: How to Become an Angel Investor with Yigit Ihlamur

What is the Silicon Valley Investors Club?

The Silicon Valley Investors Club (SVIC) is a community created by and for technology professionals who are interested in becoming more discerning, knowledgeable, and profitable investors. Our members are dedicated to learning how to make wise investments in real estate, stocks, bonds, startups, company acquisitions, and financial planning by discussing investment strategies and experiences. Each day, a story related to investing will be posted to the group’s Facebook page to serve as a jumping-off point for in-depth, quality discussions among like-minded investors. Make sure to join our Facebook Group.


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