Tech stack investing outperforms every index
Aaron Levie argued that simply buying stocks of the tools in Box's tech stack over 20 years would have outperformed every major index.
Snapshot · My First Million
I dropped out of college and built a $3.6B company from scratch
Explore episode
Jul 2, 2026
Where this was said
Angel Investing, Missed Bets, and Investing in Your P&L
At 20:25 · chapter starts 17:05
Shaan reads out a ChatGPT-generated version of Aaron's angel investment portfolio (Stripe, Figma, Robinhood, Airtable, Instacart, Plaid) and Aaron gently corrects it — attributing some entries to 'good embedding space clustering' rather than actual investments. The Figma story is the most revealing miss: he met Dylan Field at the seed round, liked him enormously, but couldn't visualise real-time collaborative design in the cloud. He was a 'huge Luddite on the pitch.' [1] — Shaan Puri "Shaan Puri calls it 'investing in your P&L' — just buy shares in the tools you're already paying for and couldn't switch off. Aaron Levie a…" 19:23 The conversation then opens into a broader investing framework that both Aaron and Shaan find compelling: what Shaan calls 'investing in your P&L.' The idea is simple — look at your expense line items, identify the tools you'd never switch off, and buy those stocks. Aaron confirms the thesis: Box's 20-year tech stack, if you'd just bought those companies' equity, would have outperformed every major index. SanDisk — one of Box's key hardware suppliers and a company that helped catalyse the move to cloud storage — is up approximately 3,000% in two years. The data, Aaron notes, is basically public. Engineers know what's good before anyone else does. Within 90% accuracy, paying attention to what engineers use tells you most of the investment advice you need.
Invest in Your P&L: The Tech Stack Strategy
Shaan Puri calls it 'investing in your P&L' — just buy shares in the tools you're already paying for and couldn't switch off. Aaron Levie agrees: Box's tech stack over 20 years would have outperformed every major index. SanDisk, one of Box's key suppliers, is up 3,000% in two years. The data is public. Most investors just don't leverage it.
SanDisk stock up ~3,000% in 2 years
SanDisk stock rose approximately 3,000% in the past two years, which Levie noted as a missed investment opportunity given Box's supplier relationship.
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