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
Jeroen Blokland – Know the Actual Business Outlook Before Investing
ISMS 8: Larry Swedroe – Are You Overconfident in Your Skills?
Brian Feroldi – Be Careful When Trading Options
Matt LeBris – Prepare for the Downs During the Uptime
Pim van Vliet – Just Because It’s Cheap Doesn’t Mean You Have to Buy It
ISMS 7: Financials, Cons. Disc., and Utilities Sectors Look Most Interesting
Logan Nathan – Your Supplier Is an Extension of Your Business, Not an Outsider
Louis-Vincent Gave – Your Success Comes Down to Portfolio Sizing
Adam Rosen – Build to Sell From the Start
ISMS 6: UK Looks Most Interesting Among the Top 5 Stock Markets
Terri Spath – Always Know When to Buy and When to Fold
Brett Martin – Fix Your Partnership or Quit It
Damon Pistulka – Be Careful of Concentration Risk
ISMS 5: How Rising Rates and Oil Prices Are Contributing to 6.4% Inflation in the US
Pia Singh – Mistakes Are Inevitable, So Be Prepared
Raghav Kapoor – Be on High Alert When You’re Doing Well
ISMS 4: Bond Yields Are Showing the Fed Has Won Its Battle Against Inflation
Praveen Kumar Rajbhar – Don’t Fall in Love with Your Own Ideas
Larry Swedroe – Beware of Idiosyncratic Risks
ISMS 3: Will the US Have a Recession or a Soft Landing?
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