Proust Startups

Proust Goes Tech With Prerna Gupta, Founder And CEO Of Hooked

As the co-founder and CEO of Hooked, an app that brings literature to the screens of the Snapchat generation, Prerna Gupta is pursuing her dream to live a life free to work on what she pleases, but her path to get there wasn’t always so clear. After graduating from Stanford, realizing that she hated management consulting, and then quitting her next desk job at a venture capital firm, she started with her now-husband Parag Chordia. Her appreciation of life, art, and entrepreneurship propelled her into her current endeavor.

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Last week, Crunchbase News spoke to Gupta about her love of people, inability to surf, and passion for the Lord of the Rings. We enjoyed her candor and lightheartedness in our latest installment of Proust Goes Tech!

What would you otherwise be doing right now?

There’s really nothing else I’d rather be doing. I’m very fortunate to kind of spend my time doing exactly what I want.

I run my company with my husband. When we met 13 years ago we made this pact with each other that we would build our lives around each other and would find a way to make a living while also spending as much time together as we can and doing exactly what we want to do. There have been ups and downs during that journey, but we’ve always stayed committed to that.

So I’m very fortunate to be able to say that I’m doing exactly what I want to do.

What is your main fault?

My biggest weakness, as a business leader, is that I’m not a very natural networker. I think a lot of times as a business leader there’s this expectation that you’ll always be growing your network, and attending a lot of conferences and dinners and all of these things. I do it when I have to, but it’s not my favorite thing to do.

But I also believe in playing to your strengths, and, when you can, turning your weaknesses into strengths. So I think my relative advantage if I were to take that weakness and turn it into a strength is that I carve out more time to spend with a small group of people and build close relationships with them. I think the best work gets done when you’re working with a small group of people that you feel very comfortable with.

I guess you can say I’m a “product CEO.” I like to just be with my team and be focused on building product. So I’ve tried to turn that weakness into a strength.

What is the quality you most desire in a tweet?

I would say wit. People who are really good at being super clever and witty in 140 characters— or 280, I guess—that’s what Twitter is all about. I really admire people who can get an interesting point across while also being witty with their words.

What is your idea of misery?

Being alone. You know? Being without love. I think that’s misery for everyone. I mean, well, starving would be another one. But I think for most of us that have that taken care of it’s being alone. Being without love.

What do you appreciate the most in your friends?

Being themselves. I think so much of our interpersonal interactions, especially in America, are so fake. Most of us all stay at the surface level when we’re interacting with each other. I think friendship is being able to just totally let your guard down and completely be yourself. Relationships are the most rewarding when you can do that, and to me that’s what friendship is.

What skill do you wish you possessed?

Oh, there are so many! Can it be imaginary? I’m going to give you an imaginary one and a real one.

The imaginary one is definitely that I wish I could fly. My husband and I really like to hike, and there have been so many times where we’ll go on a tough hike and we get to the top, and I’m tired, but we have to go all the way back down. When we’re at the top I’m always like, “I wish I could just spread my arms and fly down to the bottom.”

There are actually people that can do that; it’s called base jumping. So it’s not exactly imaginary, but for me it’s imaginary.

The real one is that I wish I could surf. I will preface that also with the fact that I have been trying to surf for years. I’m terrible. The reality is that no matter how hard I try I’m never really going to quite master it probably.

Yeah so, if we were in the Matrix and could just upload a skill, I would upload surfing.

What is your most impactful book? 

That is also a hard one. I’m just going to go with my favorite book which is Lord of the Rings by J.R.R. Tolkien. It’s just the most iconic story about the struggle of love versus the desire for power. Although it’s obviously fantasy and an allegory, I just think we see that same struggle being played out around us again, and again and again. We see it happening right now in the government. I think as a business person and a CEO it’s really easy to let the desire for power consume you entirely. There’s so much pressure in a lot of ways to let that happen. I’m so thankful to have read that book. It’s informed so much of the way that I live my life.

What defines success for you?

Living a life of love and being able to spend my time doing something that’s meaningful to me. I think if you have love and purpose, you’re successful.

When is confidence lost for you?

I think that confidence wavers, but I don’t think it’s ever fully lost. Confidence comes from deep within. It’s about knowing yourself and not giving up in yourself. I’ve had many points throughout my life where that confidence has wavered, but it has never been lost.

You have these moments when you’re completely beaten down, though. As an entrepreneur you’re always going against the grain and people are telling you 9 times out of 10 that you’re wrong, that what you’re saying makes no sense, and that you’re crazy. So you’re always having to battle against that. Then there are these moments in your journey where something happens and it just smashes you to the ground. Those are the moments, those dark moments. If you’re thinking in terms of story telling it’s the “dark night of the soul.” All of these things that people have said to you for so long suddenly make you start saying, “Maybe they were right.” Those are the moments when confidence wavers the most.

Then you dig deep, and you ask yourself if you still believe in yourself and your mission. And then you get back up.

Which buzzword is exhausted?

I’m starting to see it too much. It’s the word “slay.” It’s awesome but it’s like in every single tweet now I think. So, yeah, let’s move on.

What virtues do others have that you don’t?

I think basically selflessness. I think I have a tendency to be a little egocentric. I really admire people whose natural tendency is to be selfless.

And I try. It’s something I’ve been working on my whole life. I try to be better about it and be more self aware. But I think it’s amazing when people are born with the tendency to be selfless and to put other people first.

What impact do you want to leave behind? 

I want to show what’s possible in life. I hope that my life is an example of the depth of love that we can experience, and the joy that we as humans are capable of creating for ourselves and for others. So everything that I do is with that goal in mind. It’s one of the reasons that my husband and I pursue opportunities in art. We believe that art is one of the universal sources of joy in people’s lives, and it’s what we use, as humans, to express the human experience and to help each other reach greater levels of consciousness. That’s what we’re trying to do, and that’s what I hope my life’s work amounts to.

What is the biggest problem tech is failing to solve?

I think the issue that’s staring us all in the face is mass hysteria. Tech has enabled mass hysteria. Now the monster is turning on itself, and the hysteria has been pointed towards tech as the creator of all of the evil in the world—which obviously isn’t true.

I think one of the books that really predicted this in a lot of ways is The Circle by Dave Eggers. It was really prescient and speaks to a lot of the things that we’re seeing post Trump. Everyone is being worked up constantly into this frenzy. They’re feeling this great anxiety like everything is terrible in the world. Then they’re looking for a scapegoat for the anxiety that they’re feeling.

Tech does a lot of great things, but tech has also enabled this. We haven’t figured out a way to help contain it, or to use that energy in a positive way as opposed to just feeding the beast.

Editorial Note: Answers edited for brevity and clarity.

Illustration Credit: Li Anne Dias

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