I was once discussing with a friend –
“Let us pick a startup every week and write in public why it won’t succeed. We will be right 9 out of 10 times. Even for Series A, B, or C startups, we can still be right 7 out of 10 times. We might even gain a big following for being a naysayer.”
Sure, it feels good to be right—but does it really prove anything? Not really.
The real skill isn’t just about pointing out why things won’t work; it’s about understanding what could and betting on them. The tough job is picking 10 startups and seeing at least 2 of them succeed. If one can get 3 or 4 right, he/she is already a legend.
Here are a couple of areas that can help in the learning journey:
a) Learning from startups that defied criticism and succeeded. Many successful startups were initially dismissed for various reasons, but key assumptions changed over time, enabling their success. For instance, the rise of mobile and cloud technologies turned once “unviable” ideas into thriving businesses. The real question is—what assumptions might change in the next wave of innovation in a particular sector, and how well can you identify them?
b) Learning to evaluate founders beyond their pedigree. It’s not just about their background or ambitious vision, but about their resilience and adaptability. Do they have the right balance of grit and flexibility to push through challenges without giving up?
