San Diego/Coronado – The Best Trade of My Life

I talk a lot about stocks, markets and investing, but the best trade of my life was a move.

In the summer of 2009, Ellen and I picked up a rental sign off a lawn on B. Avenue on Coronado and walked into the house and made an offer. The kids were at summer camp. We would have some explaining to do.

We had not rented our home in Phoenix, had not thought through schools,logistics, friends and family, but it just felt right.

That trade set in motion some fantastic things.

We became renters ourselves and a one car family. I walked to work. The kids learned to ride bikes and walked to school.

In 2010, despite the math of renting over owning, we bought a home. The month we bought, turned out to be a low in housing. I had to sell some Buddy Media stock in order to buy the home, because neither my dog Bagel nor I qualified anymore for a loan (that was a bad trade within the trend of the big trade :) ).

Not all trades are for money. Sometimes you just need to really change things up, even when they are going well.

What was your best trade and/or a trade you are looking to make?


  1. Dan Emmons says:

    My entire career, I’ve had one foot in software development, while I’ve had one foot in trading. My goal that I’m looking forward to, is to have both feet solidly on the trading side. I have been waiting for the right time with extreme patience. I am ready.

  2. Wlabney says:

    3 trades: Marrying the right woman, leaving a big bank/brokerage to start an RIA firm, and buying SSO in Feb 2009 (haven’t sold any yet).

      • Wlabney says:


        Thank you for your reply, and for all of the work you do. Stocktwits & Twitter have changed the investment world for the better. I share your thoughts on the RIA trend. In our east coast beach community, we are one of only two pure RIA firms in the marketplace. It is a big advantage for us. Regarding SSO, I agree there are plenty of flaws with leveraged ETFs. I have never recommended them to clients, and never invested or traded them, with the exception of buying SSO & URE in 2009. What I have found is that the performance of the SSO is far more accurate than the 3x trading indexes. Since purchasing on Feb 17, 2009, my return excluding dividends has been 291.05%. Looking at the comparable return for SPY, I do not see much slippage… at least not on a long term level, perhaps it’s more prevalent on a day-to-day basis. Still, I agree that there were better plays in hindsight… Ford, Starbucks, Whole Foods, Celgene, etc. It took courage & capital to invest in equities in general in Feb 2009. Both of which were in very short supply in the market at the time. My SSO investment I mentioned was down 25% in the first few weeks. Crazy time.

        Thanks again for everything. Love seeing the pics of Max. I have a 1.5 year old curly headed boy, and I can’t wait to get him out on the course with me!

    • THE RIA trend is the best financial trend I can think of. your costs of running the bussiness kjeep dropping and the expectations of customers so low.

  3. rosswhiting says:

    Selling my Apple Stock in late 2009 for a nice downpayment on a home in Brooklyn. Angel investment in Honest Tea back in the day, was a solid trade as well, they sold to Coke.

  4. purecharger says:

    Similar: moved to San Diego in 2009 from the Bay Area and bought a condo downtown in 2010. As a software engineer I could be making much more had I stayed but the quality of life here means I have no regrets.

  5. TheAcsMan says:

    Traded in being a Pediatric Dentist with a reasonably prominent academic career for an obscenely paying clinical career, which I then traded for early “retirement” and a life of full time active portfolio management and the creation of a subscription Trading Alert program.

  6. Hubert Dekock says:

    ‘Thanks to’ the financial crisis I took a year off. During that year, I’ve learned Android & Java programming from scratch and thanks to my Android apps ( I came to StockTwits. Thanks to stocktwits I’ve learning a lot from other investors and discovered $TSLA and bought a few thousand shares & calls below $40. Now I’m thinking about the next steps … my best trade was to take the decision to develop for Android 4 years ago when $AAPL was dominating and not so many people were looking yet at Android. Now I have 2 apps in the TOP 100 Financial Paid apps section of Google Play. My Droid earnings are reinvested into the market and multiplying at a very nice rate. I could quit my daily job if I wished but want to accumulate some more capital before taking the next big step… also I like my current job and can perfectly balance the 2 for the time being.

  7. kenberger says:

    Single life for married. That deal seemed to come at a hefty premium a year ago. But big dividends are accruing continually.

  8. kenberger says:

    Some of my favorite trades are ones that aren’t made.
    I spend plenty of time in NYC and SF, but actually live in neither.

  9. William Mougayar says:

    There’s some Netscape money from 1999 in my current house :)
    I remember that trade very well, and where I was when I sold those beautiful options. If StockTwits was around, I would have stocktweeted it.

  10. Peter Thulson says:

    Best trade so far was a tennis lesson for lunch (via buying bar stools on Craigslist), which led to a new job in retail, which then led to my first job at a startup + moving to SF. Never realized bar stools and a tennis lesson could have so much LTV :)

  11. thorgood says:

    yeah Howard,,ya can’t go wrong with real estate in Calif..I bought a house in Venice..hated California, the neighbors, the house..but hey, I made money and now so glad to be back East I could scream! Coronado is cool. enjoy!

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