My Worst Investment Ever Podcast
Business:Investing
BIO: Jerry Parker started his trading career in 1983 in the Richard Dennis Turtle Program. He started Chesapeake Capital in 1988. Chesapeake manages about $200M in private funds, mutual funds, ETFs, and managed accounts.
STORY: Jerry has had some stinker investments in real estate and gold over the years. Two things that have cost him money in his real estate investment are overpaying and not being patient. Often, Jerry would find himself buying homes by speculating and thinking that he knew what he was doing, only to realize that he didn’t.
LEARNING: Understand what you’re capable of and your limitations as well. Be afraid of situations you’re unfamiliar with and assume the worst.
“If you’re at a poker table and don’t know who the patsy is, it’s usually you.”Jerry Parker
Guest profile
Jerry Parker started his trading career in 1983 in the Richard Dennis Turtle Program. He started Chesapeake Capital in 1988. Chesapeake manages about $200M in private funds, mutual funds, ETFs, and managed accounts. All of the trading is done using a Trend Following + Nothing approach. The funds are maximally diversified and include bond, commodity and currency futures, stocks, crypto, and FX forwards. Jerry is active on Twitter and Twitter Spaces at @rjparkerjr09.
Worst investment everOver the years, Jerry has had some stinker investments in real estate and gold. Two things that have cost him money in his real estate investment are overpaying and not being patient. Often, Jerry would find himself buying homes by speculating and thinking that he knew what he was doing, only to realize that he didn’t.
Lessons learnedFind a great mentor in a field you’re passionate about, and learn from them. Also, be ready for a big break.
Jerry’s recommendationsJerry recommends finding people on Twitter and subjects you’re interested in and following them for great advice. He also recommends listening to podcasts and reading books to get information about things you can’t learn in college.
No.1 goal for the next 12 monthsJerry’s number one goal for the next 12 months is to stay disciplined, keep doing what he’s been doing, and continue improving his portfolio.
Parting words“Thank you for having me. I will go back and listen to some of your old podcasts.”Jerry Parker
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Connect with Jerry Parker
David Hay – The Importance of Range Expansion
Rex Salisbury – Quitting Can Be a Very Important Skill to Exercise
ISMS 23: Larry Swedroe – Do You Allow Yourself to Be Influenced by Your Ego and Herd Mentality?
Harvey Sawikin – Do Your Own Homework
Paul Krake – Surround Yourself With Experienced People
Noel Smith – Always Have Risk Measurements in Place
ISMS 22: Toyota vs. EV Extremists – Who Is Right?
Guillermo Cornejo – Don’t Underestimate the Value of Experience
Eugene Ng – Keep Playing the Long-Term Game of Investing
ISMS 21: CPI Collapsing Across the Globe
Nick Maggiulli – Don’t Buy Individual Stocks
ISMS 20: Larry Swedroe – Do You Extrapolate From Small Samples and Trust Your Intuition?
Larry Shumbres – Invest in What You Know and Is Regulated
Jesse Felder – Don’t Rationalize a Lousy Trade
ISMS 19: 5% March 2023 CPI Could Fall to 4% By Year-End; If Oil Doesn’t Fly
Sachi Wickramage – Target the Customer With the Problem at Scale
ISMS 18: Dave Collum – What Makes Your Investments Good or Bad
Vincent Deluard – Know the Difference Between a Trade and an Investment
Igor Yelnik – Think About Non-Market Risks
Bogumil Baranowski – Be Careful With Businesses in Secular Decline
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