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created: June 2024
A while ago, I stumbled across a Peter Thiel quote that stuck with me: "You should learn from success, not failure." In Silicon Valley, this borders on heresy and contradicts the celebrated "fail fast" mantra. We encourage experimentation and wear our failed ventures like merit badges.
My first reaction was mixed. Having accumulated my share of failures, I'd always comforted myself with the notion that these setbacks somehow made me wiser. Was this just elaborate psychological coping? Was I rationalizing wasted time?
Consider this: for something as complex as a startup, there might be 1,000 ways to fail but perhaps only 10 paths to success. When we fail, we merely eliminate one approach from an almost infinite set of wrong strategies. When we succeed, however, we discover a working blueprint. Like Paul Atreides seeing thousands of possible futures but only one narrow path to victory, that successful pattern contains exponentially more valuable information.
Take fundraising. Unless your name is on the transformers paper, raising money means talking to multiple firms and collecting numerous "nos" before getting a yes. This is why you're supposed to schedule your second-choice firms first—to gather the inevitable rejections and feedback. While the concerns raised during these meetings help address gaps in your presentation, addressing them offers no guarantee of success. Often, feedback is just a polite way of saying "we don't believe in you." The genuine breakthrough comes with securing that first term sheet. We then replicated that approach with slight improvements and landed another one. By the third, the pattern becomes clear—you can see all the variables that contributed to success.
This principle extends other aspects of life and business. When conducting dozens of sales calls for my startup, I made countless rookie mistakes. While failures helped tighten my process, the real progress came after signing our first major client. I then replicated that process with improvements, targeted similar companies, looked for familiar buy signals, and repeated the success. Failures still occurred, but founder-led sales was no longer a nightmare. Eventually, I could determine an opportunity's potential within the first five minutes.
There's also an overlooked psychological aspect to this thesis. When we fail, our brains work overtime protecting our egos. "Investors aren't smart." "The client was never serious." "Timing was off." We become unreliable narrators of our own failures. Success, however, creates psychological safety for brutal honesty. My team's most valuable post-mortems follow wins, not losses. After failures, conversations drift toward speculation and often lead to erroneous conclusions. After success, people can objectively dissect both their strengths and weaknesses, creating actionable insights.
What makes failure particularly challenging as a learning tool is its complexity. Most businesses don't fail for a single reason—they fail for multiple, intertwined reasons. When your startup doesn't make it, you might blame team dynamics, only to realize in your next venture that market fit was equally problematic. Then in your third attempt, you discover that product strategy was also fundamentally flawed. It's like trying to solve a puzzle where you can only see one piece at a time.
If you're determined to learn from failure, you need to approach it with paranoia and overcompensation. Instead of fixing just the most obvious issue, you must meticulously catalog every potential weakness and address them all with exponentially more effort. This means not just upgrading your team, but also pressure-testing your market assumptions, scrutinizing your product strategy, and examining every other variable with 10x more rigor.
So now when something works—even something small—I study it carefully. What exactly worked? Why? How can I replicate and scale it? Those answers have helped me build unique knowledge. While failures are immensely important and build character, I've learned that the best way to deal with them is to forget about them and move on.