An Investor’s Retirement Plan | Chip Chapin | Investors Therapy Session #2 (continued)

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 Speaking with Jordan Thibodeau about Investing and Retirement Planning

In this episode of Investors Therapy, Jordan Thibodeau and Chip Chapin finish up their discussion about investment strategies and share advice on planning for retirement. Chip also explains how (and why) he has continued to invest after retiring from the workforce.

This is the second half of our two-part interview with Chip Chapin. You can find the first part here.

In this talk, you’ll learn about:

  • Chip’s thoughts on retirement
  • Tips for managing your healthcare during retirement
  • Steps you can take leading up to retirement to make it go smoother
  • Thoughts on continuing to invest during retirement
  • Insight on passing down your assets and equity to the next generation
  • The books that most influenced Chip
Jordan Thibodeau and Chip Chapin Finish Up Their Talk from Investors Therapy Session #2

Chip Chapin’s Book Recommendations:

The Battle for Investment Survival by Gerald Loeb

How to Make Money in Stocks by Bill O’Neil

Black Swan Book by Nassim Nicholas Taleb

The Millionaire Next Door by Thomas J. Stanley, Ph.D., and William D. Danko, Ph.D.

The Bible

The Second World War by Sir Winston Churchill

The Madness of Crowds by Douglas Murray

Notes from the Talk:

1:39: What were your feelings leading up to retirement? What was going through your mind, financially?

5:25: Does real estate give you a sense of meaning in your life after retirement?

9:00: Does real estate investing keep you active and fulfilled during retirement?

10:37: What are some unexpected retirement complications that you’ve run into, particularly regarding healthcare?

15:34: If you’re planning on doing any major refinancing, then get it done before you retire.

16:15: If you’re planning on retirement, then front-load your 401k contributions for that year so that you max out your 401k before you leave the company.

17:39: Did you look for tax diversity in your holdings for retirement? (e.g. pre-tax and Roth)

18:27: What is the “mega backdoor”?

20:12: Have you ever used a self-directed IRA for any of your real estate investments?

24:12: What is your eventual exit strategy from real estate investing?

26:42: Finding meaning in the guardianship of passed-down financial assets and equity

29:40: What is one book you’ve read that has made you a better investor?

33:21: What is one belief that has made you a better thinker?

33:45: How our notion of risk impacts our lives

38:30: What is one book you’ve read that has made you a better person?

41:47: How can you avoid being swept up in the crowd?

43:43: The negative influence of financial TV

44:31: Conclusion

Related Links:

Real Estate Investors Toolbox

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

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

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