Pop Quiz, Monday with Gautam Gupta

The single piece of advice I can give is to manage your emotions and stress to avoid the roller coaster ride of startups. Entrepreneurs need to be prepared for an emotional roller coaster with twists, turns, emotionally charged highs, and terrifying lows.

The Pop Quiz, Monday is a fun little exam that we love to give to savvy business owners. The examination is not a surprise after all since the interviewee already knew about the questions in advance. However, we can always pretend and have fun with the scenario of a young entrepreneur sitting in class nervously biting on their pencil. They are ready to take a pop quiz on a chapter that they were supposed to read the night before. Instead, they played Metroid all night on their SNES (Oops, this was me in high school). The real purpose of the pop quiz is that this is a fun way to introduce business tips from real-world experiences that you can not learn in a classroom. We want to thank our entrepreneur for being a good sport and volunteering their time to answer a few questions to help our community grow from their knowledge.

I want to introduce you to our guest today who will be taking our Pop Quiz Monday.

Can you please tell everyone your name?
Gautam Gupta

Gautam Gupta

What is your job role?

Tell us about your company?
NatureBox is a multi-channel brand that creates healthy and delicious snacks. We have over 100 unique snack products at any time and have launched over 400 products since inception. We use consumer data to drive all our product development and merchandising.

What do you love most about your job?
Every startup has its ups and downs, but if you’re passionate about the product, I think it helps weather much of the typical roller coaster ride. I started NatureBox, in part, because of my childhood struggle with obesity. I grew up very overweight and ate a lot of junk food. Learning about nutrition helped me to lose 70 pounds in six months and keep the weight off ever since. This passion for healthy food and nutrition is what makes NatureBox so personal to me. I love the chance we have to create products that change consumer behavior around snacking. In the end, I hope we can make snacking a bit healthier and fun.

What motivates you to get up every day and go to work?
I’ve always enjoyed working – even in my last job as a venture capital investor, I was excited to get to the office each day to meet with brilliant entrepreneurs who aim to change the world. As someone who loves to learn, those conversations motivated me to work hard. Today, the opportunity to learn how to build and scale a company keeps me motivated – even during bad times, because every setback is also an opportunity to learn.

How do you have fun at work (team building, pranks, etc..)?
Just getting communication and culture right are so hard that I’ll choose to talk about a few of the things we did over the years to try to reinforce a culture of transparency, optimism, and learning.

Wins – after talking to our staff a few years ago, we found that we were really bad at celebrating the small and big wins as a company. We glossed over the things that were going well and focused on how to solve the problems. This created a lack of optimism and celebration that we wanted in the culture. One of our employees came up with an amazing idea he called “Weekly Wins” where every Friday, employees could gather to share one win or learning from the week with the rest of the company. These short 10-15 minute stand-up’s were filled with laughter and applause, creating awesome energy to close the week.

Office Hours – We wanted to create an atmosphere of transparency but were finding it difficult to get employees to ask the questions on their mind. After some attempts at anonymous Q&A, we decided to provide more opportunities for folks to talk via smaller groups. As such, we created an office hours program where employees could come to discuss questions on their mind with another senior executive or me. We would also frame specific topics for these office hours to solicit more engagement on certain issues. This was a very low ‘cost’ initiative that creates greater transparency and learning about our business.

What advice would you give to someone who is starting in your industry?
The single piece of advice I can give is to manage your emotions and stress to avoid the roller coaster ride of startups. Entrepreneurs need to be prepared for an emotional roller coaster with twists, turns, emotionally charged highs, and terrifying lows. The most important lesson I’ve learned is not to let the ups and downs of the business affect you. I know this is easier said than done, but keep in mind that you are in it for the long haul. I like to tell friends – without sounding pessimistic – no matter how good something seems. It’s never that good. Similarly, no matter how bad something seems, it’s never that bad. Get off the roller coaster, keep your head down and build.

Thank you for taking our pop quiz today. You get an A+ for effort. You can learn more about our interviewee and their business by visiting them on the web:




Author: Ricky Singh, MBA

Editor of The Startup Growth.

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