It’s hard to believe, but finals week is already here! Amidst papers, late nights, and coffee runs, we’ve been engaged with an incredible female founder in the tech space – you might even say we’re hooked. Meet Prerna Gupta, CEO & Founder of HOOKED, a digital storytelling platform reaching 100 million Gen Z viewers worldwide and #1 on the app store charts. We’re so excited to share her incredible story with you!
Sophia Naqvi, Membership Engagement Chair 2020-2021
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PRERNA GUPTA OF HOOKED
“The most important thing is to dive in. If you want to be a founder and you have an idea, just go for it.”
- PRERNA GUPTA
Prerna Gupta is a female founder who has launched entertainment apps reaching over a billion people. She is currently Founder & CEO of Hooked, a storytelling platform reaching 100 million Gen Z viewers worldwide. Hooked has been the #1 app on the App Store and Google Play in 25 countries and has won numerous design awards for its innovative chat fiction format. You can read more about what led Prerna to found a storytelling startup in this article she wrote for Vogue.
Hooked investors include Sound Ventures (Ashton Kutcher), The Chernin Group, WME/Endeavor, MACRO (Charles King), Steph Curry, Kevin Durant, LeBron James, Mariah Carey, Jamie Foxx, Joe Montana, Anjula Acharia, Aasif Mandvi, Cyan Banister, Eric Ries, Cowboy Ventures, Founders Fund, SV Angel and Greylock, among many others.
Prerna has been named one of the Most Influential Women in Tech by Fast Company, and her writing has been featured in New York Times, Vogue, Forbes and TechCrunch, among others. Prerna graduated Phi Beta Kappa from Stanford University.
You’ve published an article in Vogue about your experience living as a nomad for a year. How did this experience impact the creation and development of Hooked?
Hooked wouldn't exist if I hadn't taken that year off and traveled. I’d just sold my previous startup, which was also in the mobile app space. It used artificial intelligence to help people make music on their phones. We’d had some success, reaching millions of users, and then sold our company to one of our competitors. At this new company, my husband Parag Chordia and I became executives. We’d spent a couple of years there when we started to feel ourselves stagnating. For us, everything we do lies at the intersection of technology and art. Creativity is so important for us in our careers and in our lives. We felt that our creative souls were slowly dying.
Parag and I decided to leave Silicon Valley, donate all of our things, and go traveling for a year. Soon, I started writing a book, a sci-fi fantasy trilogy set in Silicon Valley in the future. It's a novel for young adults. As we were traveling, I started to think about what's happening in the world of fiction. When you travel and meet new people, they always ask you, “What do you do?” I’d say, “I'm writing a novel.” And people would react, well, that's cute, but what's the point? “Teens don't read anymore.” I’ve heard that several times. It made me realize that there is an opportunity to rethink storytelling for teens on the mobile phone. That was what gave me the inspiration to start Hooked.
The apps you’ve created have hit #1 on the Apple store charts and have, in total, over a billion users. Could you tell us a little bit more about the product development process for your apps?
I like to think of it as a science experiment. We always start with a hypothesis. For example, with the case of Hooked, people say that reading is dying and teens don't read anymore. An obvious explanation is that social media is way more interesting than reading. But our belief was that stories are fundamental to the human experience. Especially when you're a teenager, interacting with stories is how you connect with other people from different walks of life. Through that, you learn more about yourself. We thought that reading doesn't need to be boring, but the format of the novel doesn't make sense on the mobile phone. Our hypothesis was, if we can create a new type of reading format that feels native on the mobile phone, we can make reading engaging for teens.
Then, we had to test this hypothesis and figure out how to create this format. We started by testing different formats for reading. For each test, we would spend a few days developing a barebones app. One of the things we tried first was image-driven ideas: stories that were told primarily through images, with few words. We created a mobile-optimized website and released ads on Instagram, driving a few thousand people to it. Then, we looked at the data to get a sense of what's resonating with the users and what's not. By analyzing the data, we’d make modifications, test the modified version, and get slightly better results each time. Through this process of iteration, we eventually came up with the idea of telling stories through chat conversations. That was our light bulb moment where everything clicked and things started to take off. So our process for going from idea to product-market fit is like a science experiment where you build a hypothesis, create tests, gather data, and iterate based on that data until you get something that works.
Hooked has an incredible repertoire of high-profile investors, including Stephen Curry, Founders Fund, and Cowboy Ventures. As a woman of color founder, how did you navigate the fundraising process and the challenges that came with it?
Fundraising has been really, really challenging for me my entire career. I have been an entrepreneur for over 16 years since I graduated from college, and it's something that has taken me a long time to figure out. When I first started, fundraising was nearly impossible. I mean, to be a short brown woman going into these pitch meetings, especially when it was all white men 16 years ago. In these meetings, they're so used to founders looking and sounding a certain way that even little things, like my soft voice, added another layer of difficulty.
This is my third startup, but with my first one, I barely raised any money. We were always just scraping by as we could never raise enough money fast enough. By my second startup, things got a little bit easier. I figured out how to tell a story that resonates with investors and how to use my differences to my advantage. For example, since my second startup was a music creation app, I would open the pitch with a music demo where I sang into our app, to show how the app worked. That demo always caught people's attention. I turned my soft voice, which doesn’t project well when talking but is great for singing, from a disadvantage into an advantage! We raised more money for my second startup than we did for my first one, but it was still less than $500 thousand dollars in both equity and grant financing. Ultimately, the startup was successful, and we had a good exit.
By my third startup, things got much easier. I had relationships with investors who’d had a good outcome with me before, and so they were willing to make a bet on me. They introduced me to other people, and things took off from there. Fundraising is very difficult when you're different. But my advice is to stick with it. Don't let rejection get you down and use your differences as your strength.
What are the best ways, in your opinion, for college-age women interested in technology and entrepreneurship to pursue such interests?
The most important thing is to dive in. If you want to be a founder and you have an idea, just go for it. Don't worry if it's not perfect, or if you don't have a co-founder, or if you don't have funding yet, just break it down into small problems and start solving one problem at a time. Just dive right in. If you don't have an idea yet, join a startup. You will learn so much when you're on the ground. The smaller the team and the earlier stage the startup is, the more you'll learn. The best possible way to learn about tech and entrepreneurship is by doing it so just start out. Don't wait. Immerse yourself right now.
What skills do you think are vital to running a successful startup, particularly in the technology industry?
I think there are four key skills. Number one is a data-driven mindset. One of the best ways to understand this idea is by reading a book titled The Lean Startup by Eric Ries, one of our investors. The basic idea is to use data to make your decisions. You test things: test early, test often, and use an analytical frame of mind to decide which turns to take in your startup.
Number two is curiosity. As a founder, you're always learning. I think the key to being successful is to learn new things, improve yourself, and grow your business. Look at the founders that we consider to be the greatest of the great, the Jeff Bezos and Elon Musks of the world. Think about how even at that level, at that stage of their careers, they're always innovating and creating, going after crazy ideas that the rest of the world thinks are impossible. That's because they're incredibly curious and always want to learn, so I think that curiosity is key.
The third key skill is sales. Ultimately, as a founder, you’re a salesperson. This is something that didn't come naturally to me, but you can learn over time. You are always selling to prospective customers, investors, job candidates who you want to recruit, to the media. You're always selling, so sales is an important skill.
Number four is perseverance. This might be the most important skill for a founder. You are going to get knocked down every single day. You will face rejection constantly. You will face obstacles. You will face failures. And the thing that separates the people who succeed from the people who don't is the ability to persevere through all of those failures to make their vision a reality.
What advice would you give your 20-year-old self?
This is going to sound counterintuitive coming from a business person, but my one piece of advice is this: the only thing that matters is love. When you're creating a startup, you're taking on an incredible amount of risk with your career, with your finances. And odds are you're going to fail. That's just the reality. I've experienced a lot of failure in my career. Regardless of whether the outcome is what you predicted or not, the journey will be valuable and fulfilling only if you do it for the right reasons. To me, this means going through all of that while living a life of love and prioritizing good relationships. It doesn't just mean finding a partner; this mindset is also about the way you interact with your co-founders, the people you hire, your investors, and all the people you interact with.
If you let love be your guiding principle, everything that you do during your journey will help you improve and live a better life. You will impact other people in a positive way. To me, the greatest thing I have accomplished during this time is the teams I’ve built, the people I’ve worked with, and the special experiences we’ve shared together. To me, this has been a journey of love. It's important to remember that most founders have the same start and the same outcome. However, if you've been nasty to people your entire journey, I think that's a failure, regardless of your startup’s outcome. If you've been loving towards other people, even when you end up with the same amount of money in the bank, you are much, much wealthier.
First quick take: What are your top three favorite books?
This is a tough question for me to answer because I have so many! My number one favorite book of all time is The Lord of the Rings by J.R.R. Tolkien. I think it is the greatest book ever written. It’s a canonical story of the fight of love against the desire for power. Number two is Crime and Punishment by Fyodor Dostoyevsky, which is an important book for everyone to read, especially in these times of political upheaval. Sometimes, it seems that there is a tension between the forces of good and the forces of evil. To me, Crime and Punishment shows that there is good and evil in all of us, and it is important for us to understand that. My third favorite book is a narrative non-fiction by Jon Krakauer, titled Into Thin Air. It's a story about a disaster that happened on Everest in the 1990s. It's an amazing story of survival. I find it really inspiring because it shows what humans are capable of when we push ourselves to the limit.
Second quick take: Aside from Hooked and the other apps that you've created, what three iPhone apps do you use and appreciate the most?
I use Slack all the time, it's completely revolutionized work. I have been doing startups my entire career and this switch from email to Slack has been massive in terms of productivity. I'm a huge fan of WhatsApp too, but I use it more for my personal life. It plays a big role in my day-to-day life since I had a baby two years ago so I share all the little pictures and videos that we take with the rest of my family there. WhatsApp is amazing for helping to keep everyone in touch, especially during the COVID-19 pandemic, when we can't see each other. The third app is Good Eggs, which is a local grocery delivery that started in the Bay Area. Now, they cover other cities too, and they give me access to fresh produce, local bread, and other products that help my family stay healthy.
Third quick take: What is your favorite place that you visited during your year as a nomad and why?
It was Costa Rica. We started in Costa Rica, then traveled to many other places around the world, and came back to Costa Rica in the end. We ended up spending about five months total out of the year and a half there. There's just something special about that country. Their motto is, “Pura Vida”, which means pure life, and the people embody it. It's amazing how happy people are there. It's truly a paradise. A magical place.
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