Learn from your mistakes
Better yet, learn from others' mistakes
People say it’s really good to learn from your mistakes. And don’t get me wrong, you definitely should. What you learn usually says more about you than you think. It is a fascinating way to really get to know someone.
But in business, what’s better, I think, is learning from other people’s mistakes. My philosophy is, I want to learn, but I want to learn what others haven’t got figured out already. I don’t want to learn what a wheel is and why it takes me further than a square; I want to learn what type of rubber makes for a great wheel in rain conditions when people thought it is all the same. F1 style.
So we are launching this new thing, and the key question came about: what can we learn from others who failed before?
But I want to go beyond the obvious questions that business school provides.
Looking at the past
We wanted to know is this venture worth pursuing. We did a case study analysis focusing on a few strategic questions:
1. Drivers of success: what actually moved the needle? What were the 2-3 things that, if you removed them, the business wouldn’t have gotten off the ground at all? Split this into: the qualitative WHY (what customer pain were they solving, and how acutely?), the quantitative proof (did the numbers ever support the thesis - TAM, unit economics, growth rate?), and the X-factor (network effects, regulatory tailwind, a single founder insight, a lucky partnership - whatever made early traction possible that wasn’t obvious).
2. Trade-offs: what did they sacrifice, and was it the right call? Every scaling decision forecloses something else. When did they choose speed over margin? Geographic breadth over depth? Enterprise over SMB? The question isn’t just what they traded. It’s whether those trade-offs were made deliberately or by default. And critically: has AI, capital efficiency, or a new distribution channel changed whether that trade-off is even necessary today?
3. Market timing and fit: were they right but early, or wrong altogether? Many ventures fail not because the idea was bad but because the enabling conditions - customer readiness, infrastructure, regulation, willingness to pay - weren’t there yet. Or they misjudged who the customer actually was. Separating “bad idea” from “bad timing” from “right idea, wrong customer” is important to get right.
4. Strategy or execution: what killed it in the end? Did they fail to see what was coming (a competitive threat, a market shift, a technology displacement) - a strategic failure? Or did they see it clearly and just couldn’t move fast enough, cheaply enough, or cohesively enough - an execution failure? The inside view (people who built it) vs. the outside view (people who funded it) often diverges here, and that gap itself is informative.
Implications for the new venture
And having answered all these questions, we then look forward to what this means for us:
1. What can you do that others couldn’t? and why now? Not just “what’s your edge” but specifically: what capability, insight, or condition exists today that wasn’t available when others tried this? The answer should be falsifiable. If you can’t name the specific unlock, you don’t have an answer yet.
2. Who is this actually for? and when are they ready? A venture can have a real problem and a real solution and still fail because the customer segment wasn’t the right one to start with, or wasn’t ready to pay, or required too much education. This is the market fit and timing question in forward-facing form: who is your Day 1 customer, what do they already believe, and what triggers their willingness to act?
3. What trade-offs are you making? and are they deliberate? Same as the analysis lens but applied to your own choices. What are you not going to do in year one that will feel like a sacrifice? The test: could your whole team articulate the trade-offs clearly? If not, you’re not making them - you’re just drifting.
4. What does success depend on? and how fragile is it? Map the critical path. Which single assumptions, if wrong, kill the thesis? Which partnerships, regulatory outcomes, or platform dependencies are outside your control? Futureproofing isn’t about predicting everything It’s about knowing which risks you’re choosing to carry and which you can hedge.
Final Word
These eight questions didn’t tell us whether to build the thing. That’s still on us.
What they did do is make sure that when we decided to go, we did not go blind. We’ve looked at the graveyard. We’ve understood not just who died, but why. And we’ve asked ourselves, honestly, whether the conditions that killed them still apply, or whether something has genuinely shifted. (in this case we think it has!)
Most ventures don’t fail for lack of ambition. They fail for lack of clarity. About who they’re for. About what they’re giving up. About what has to be true for this to work.
The questions above are a forcing function for that clarity. They don’t remove the risk. They just make sure you’re choosing your risks deliberately - and that you know the difference between a calculated bet and a hopeful guess.
We went through this exercise before committing. And we came out the other side not certain, but clear. Which is the best we can ask for.
Now we build.