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
Charles Rotblut – Realize When You’re Lucky and Walk Away
Arjun Murti – You’ve Got to Get Out of the Battle At Some Point
ISMS 25: Larry Swedroe – Admit Your Mistakes and Don’t Listen to Fake Experts
Steven Wilkinson – Your Success Is 100% Dependent on You
Shawn O'Malley – Geopolitics Can Take Your Investment to Zero
Peter Saddington – I Got Fired From My Own Company
Neville Medhora – Hot Stock Tips Are Generally Unreliable
Jack Farley – Don’t Play in Markets You Don’t Know
Carter Malloy – Valuation Is Not a Reason to Invest
ISMS 24: Larry Swedroe – Confusing Skill and Luck Can Stop You From Investing Wisely
Gisela Hausmann – Encourage and Appreciate Your Employees’ Creativity
Connor Steinbrook – Do Due Diligence Before Visiting a Real Estate Property
Zachary Resnick – Invest in People Not Just Ideas
Chris Mamula – Take Responsibility for Your Financial Situation
Michael Howell – Liquidity Is the Main Driver of Asset Markets
Brady Slack – What to Look For in a Coach or Mentor
Richard Lawrence – Avoid the Stock That’s the Hype of the Day
Vineer Bhansali – You Create Real Value by Being Different
Brenden Kumarasamy – Follow the Data, Not Your Emotions
Julian Klymochko – Arbitrage Trades Don’t Always Turn Out to Be Risk-free
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