There is a cliche often associated with hyper growth startups. 

That running one is like learning how to fly a plane while you’re already up in the air. Or perhaps it's like learning to change an engine while you’re driving a car. 

There is another version of this analogy: it's like learning how to build a plane and learning how to fly it and also mastering how to change an engine mid-air, even as you’re hurtling at hundreds of kilometers per hour through the air. 

A great example of such a startup is Udaan, which in 2019 became India’s fastest unicorn within just 3 years of starting up. 

What does it take to build and scale a company in that manner? 

A few weeks ago, you heard Vaibhav Gupta – Udaan’s co-founder and CEO – answer this question in granular detail. 

Right down to how Udaan looked at the trade cycle of a small mobile accessories shopkeeper in Mysore, who got his supply from Bangalore every 15 days. 

Or the exact changes Udaan has made to their warehouses, so that they’re more efficient. 

He even broke down Udaan’s execution playbooks and what makes them reliable and repeatable. 

But…what happens when you zoom out a little?

The more high-level decisions. Which bets to take, which to let go. Which patterns to follow. What the B2B retail space in India will look like, in 10 years. And what is Udaan doing to prepare for it?

This is the episode where Vaibhav zooms out and reflects on some of these questions. 

He’s still very sharp and detail-oriented, of course. In fact, you’ll hear him say “retail is detail” with an unshakable conviction very soon, in the episode. 

But this time, you’ll notice that the larger decisions that Vaibhav makes for his organizations stems from his own strong beliefs and learnings. 

He’s an introvert, but he has learnt to discuss even his half-formed, unbaked ideas with his team. He’s driven by solving big problems, and so is Udaan. 

He’s become comfortable with being wrong, and that’s a feeling that his employees are encouraged to embrace at every stage.

We talk about all the mental models, habits and frameworks that drive Vaibhav – and the culture at Udaan. And, of course – how First Principles thinking is very crucial to all of these!

This is episode 40 of First Principles with Vaibhav Gupta—The Ken’s weekly leadership podcast.

First Principles has been named one of the best shows of 2025 on Apple Podcasts India! 

Every listen and every share is what keeps us going. We get to dive into these conversations because you show up for them. Thank you for being part of this journey with us. Check out all other episodes here.