I was just listening to the Bob Lefsetz Podcast episode in which Bob interviews Linda Perry. She's talking about her dad and how should be so rich today because back in the 1970s he was RIGHT SMACK IN THE MIDDLE of the computer revolution.Reminded me of me! Because back in the 90s I was RIGHT SMACK IN THE MIDDLE of the dot com boom. I have a LOT of coulda/shoulda/woulda stock market moments from that decade but I'm going to kick off this coulda/shoulda/woulda series with EBAY.
Here's the moment of truth that I remember: I was at a get together in a park in Menlo Park, CA, and talking to a friend about where to invest. I was preaching Onsale.com, while she was all about EBAY.
My logic was that Onsale's business model of buying up clearance items and reselling them was way better than EBAY's auctions for the simple reason that with Onsale, customers were buying from a business while EBAY customers were buying from whothehellknows. For awhile, I felt smug in my rightness as Onsale rocketed from around $15 (my buy price) to around $100. Did I sell? Hell no. Stupid, greedy, dumbass me.
Honestly, Onsale STILL makes sense to me but they are long out of business, while EBAY has risen from an adjusted price of about $.80 in 1998 to about $35.
Ouch.
Coulda: had money
Shoulda: 35x gain vs. bonfire of vanity as I held on to Onsale to sustain a total loss.
Woulda: Except I just did not believe that EBAY's business model would succeed, never occurred to me that a system so dependent on decentralized trust could ever succeed, still seems amazing!
Lesson learned: When you buy stock and it goes up nearly 10x in a few months, SELL.




