“The hardest problem in investing is not finding great companies. Shopify was never hard to identify as great. The hard part is that the market usually knows it too. And you usually have to pay a price that leaves no room for error.”
The Investor's Podcast (We Study Billionaires) - The Investor’s Podcast Network · October 2026
Closing an episode on why the hosts passed on Shopify, whose shares have since roughly doubled. O'Malley concedes their caution has looked wrong for a year and a half, but they would still rather wait for a fair price than pay for perfection.
Transcript
…intrinsic value dramatically in the last year, but shares are trading at $160 per share at the time of recording. At some point, I'm hoping we'll get a big enough sell-off so we can gobble up a bunch of shares. And if it gets close to $100, I would definitely be open to opening a tracking position.
…AI and agents will have on e-commerce in general and in the long run. And I don't know. Month, Meadow and Shopify are the big AI losers. And then the next month, they are the big winners of AI. So I'm pretty confident we will have the chance to buy them at significantly better prices in the future.
All right. Well, let's bring it home. If you take nothing else from today, I hope you'll remember this, listeners, that the hardest problem in investing is not finding great companies. Shopify was never hard to identify as great. The hard part is that the market usually knows it too. And you usually have to pay a price that leaves no room for error. And so over some periods, the error never comes and the price keeps working. But our job is just to keep showing up and staying honest and be ready for those days when Mr. Market finally has a bad reaction to something that the company has done. And to close things out, today's quote comes from the great Howard Marks, who wrote, Being too far ahead of your time is indistinguishable from being…
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