A bootstrapper's guide to best-in-class culture

Meet the oldest person in our team. That’s my mom and she is 72!

She is a lifelong learner and always finds something interesting to do with her time. 12 years ago, she retired from her job as a school principal for a Govt. school in Agra. And moved to Bangalore right after, to be closer to us.

In our young days as a brand, she started helping out with fulfilling orders, printing labels, managing the little stock we had.

As we grew, she expanded her knowledge too. She learnt all the intricacies of an order management system, Shopify backend, and reading excel sheets. Believe it or not, she has the sharpest eye for potential fraud orders. Can’t tell if that part comes from her detailed eye or her ‘mom’ instinct - no one can escape that!

Today, she manages our entire inventory system - raw materials, finished products, coordinating with our artisan clusters. Most artisans lovingly call her “Mummy ji” :). 

Part of the learning culture we’re trying to build at Quirksmith, comes from observing her closely over the last 10 years.

A learning culture for me is a place where people never stop growing in their capacity to learn. Where they feel safe to ask questions and admit mistakes without fear or embarrassment. Where the person who asks the sharpest question in the room is valued just as much as the person who has the answer. 

Essentially, a place full of people who feel safe enough to not know things yet and interested enough to go find out. All of this with a calm nervous system!

I’ve certainly heard HR (or culture) teams and CEOs of large start ups talk about this but there was no blueprint for a business that looked like mine - and I am ambitious about creating a culture that is best-in-class. I just didn’t have a playbook that applied to small businesses. 

It took me years of building Quirksmith - bootstrapped, hiring locally in Bangalore, working with people who had never worked at a "cool startup" before, to understand that great cultures do not need a certain headcount, grand budgets, or a certain “culture” expert to change things around. It is something you build deliberately from day 1. A team of five can have a richer learning culture than a team of a hundred. 

What follows isn’t advice for large organizations with L&D budgets and HR teams (although it can apply to everyone!). It's what I've learnt, and am still learning, about building a place where people grow. In a small, bootstrapped, deeply human company that is figuring it out as it goes. I'm sharing it because I wish someone had told me earlier that this was possible for us too.

THE LEARNING CULTURE RECIPE:

Spotting a curious learner:

A curious learner isn’t necessarily someone with great academics, or a shiny resume. This one interview question tells you more about a curious learner than anything else: "What's something new you learnt recently out of pure interest? Not for your work or a certification"

What they learnt is almost irrelevant, what you're looking for is the process. How did they get into it? What kept them going? Did they go deep or just skim the surface?

Curious people go to depth. They get pulled in. They follow a thread because their curiosity doesn't let them stop.

Once you hire them, your job has just begun: to get them curious about the work they'll do. Learners want to keep learning!

From a team that executes to one that figures things out

In my early years as a founder, I made a mistake a lot of first-time founders make. I assumed that once you hire good people, they'll just figure things out. That's what had been modelled and celebrated in my corporate career: self-sufficiency, initiative, not needing to be told. So I expected the same from a young team building something from scratch.

It didn't work. Because there's a critical step between hiring curious people and having a team that genuinely figures things out on their own - and that step is figuring things out together first.

It is often tempting as a founder to come in with the answers and the solutions. And there is a time and place for that - in the early days, you have to be the one with the most conviction and many of the answers. But as you grow, and as problems grow, you can’t be the only person with answers. If you do, you become the bottleneck. Worse, you build a team that has never learnt to find the answer themselves, because they've never needed to. 

When I started spotting early signs of this, I changed something in how I showed up. I started to sit side by side with every person  - did the messy analytics, the AI prompting, asked questions (out loud) I didn’t have the answers to.

That process trains your young team to learn that figuring things out is something they can do too. 

Today, watching my team work through the uncertainty, the collective failures to finally landing on something that worked has become one of the most fulfilling parts of building Quirksmith. 

Safe space to make mistakes

In a team where mistakes are met with frustration, or questions are met with impatience, people learn to stay quiet. They pretend to understand when they don't,  hide errors until they become bigger problems, and stop asking questions because not knowing the answer makes them feel inadequate. 

Building a team that genuinely learns requires an environment where being openly curious feels safe. Don't take my word for it. Amy Edmondson, a professor at Harvard Business School, has spent decades researching what makes teams perform well. And she found that the single biggest predictor of a team that learns, innovates, and performs isn't talent, or experience, or even the quality of the idea. It's whether people feel psychologically safe. Whether they believe they can speak up, ask a question, admit they got something wrong, without being embarrassed or punished for it.

Building that safety is, I've found, almost entirely the founder's job in the early years. Culture takes its cues from the top, and what you visibly do, far more than what you say, sets the tone for everyone else.

A few things to consider, if you’ve reached this far

Admit your own mistakes out loud because when founders make their own fallibility visible, it gives everyone else permission to be fallible too. 

Ask questions you don't know the answer to. “I don't know how to read this data, let's figure it out together” does more for psychological safety than any policy or value statement ever could.

Never make someone feel small for not knowing something. The moment a team member feels embarrassed for asking a question, that question is the last one they'll ask in a group setting. Watch your reactions, even the subtle ones like a sigh, a raised eyebrow, or a slightly impatient tone. These land harder than you think.

Separate the mistake from the person. When something goes wrong, get curious about what happened before you get frustrated about who let it happen. What did we miss? What would we do differently? keeps the conversation open. How did this happen? directed at a person, closes it.

Celebrate the learning, not just the outcome. What gets celebrated gets repeated, and if only successes get celebrated, people will stop taking the risks that learning requires. 

Truth is, I'm still figuring this out. There are days at Quirksmith where I get this right, and days where I look back at a conversation and know I could have handled it better, been more patient, more curious, less certain. 

Building a learning culture is a daily practice, and some days the practice is better than others.

After 10 years of building this, I’ve come to realize that the size of your team and the depth of your pockets have very little to do with the quality of the culture you can create. What it takes is intention, consistency, and the willingness to go first.