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
Kat Merchant – Do It Today
Laurent Lequeu – Sizing Is Crucial When Trading
David Kass – Don’t Invest in a Company Unless the CEO Owns a Large Stake
Christopher Panagiotu – Go With Your Gut, but Verify
ISMS 29: Larry Swedroe – The Shiny Apple is Poisonous and Information is Not Knowledge
ISMS 28: Stocks for the Long Run
Folarin Daniel Adeboye – Business and Friendship Can Never Mix
Dana Anspach – Loving a Product Is Different From Running a Business
ISMS 27: Larry Swedroe – Familiar Doesn’t Make It Safe and You’re Not Playing With the House’s Money
Manisha Thakor – Invest in Your Financial Health and Emotional Wealth
Richard Smith – Anything Valuable Is Hard
David Perry – Bet on the Person, Not the Idea
Tom Wall – If You Make Some Money, at Least Take Half off the Table
Rick Warner – Be Careful When Investing in Banks
Mohit Tater – You Don’t Know What You’re Getting Into Until You Are in It
Vorathep Srikuruwal – Walk That Property Before You Buy It
Phil Bak – Be Slow to Jump Onto Bandwagons
Jack Schwager – Never Stay in a Position That Violates What You Believe In
Sampark Sachdeva – Don’t Be Afraid to Take the Plunge
ISMS 26: Larry Swedroe – Are You Subject to the Endowment Effect or the Hot Streak Fallacy?
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