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Female Disruptors: Purva Gupta is shaking up the AI world with emotionally-intelligent AI

Don’t be afraid to challenge your thinking or change your mind.


Don’t be afraid to challenge your thinking or change your mind. I’ve learned from my mentors that it’s perfectly healthy — encouraged, even — to have an idea tomorrow that contradicts your idea today. The smartest people are constantly revising their understanding and reconsidering a problem they thought they’d solved. They’re open to new points of view, new information, new ideas, contradictions, and challenges to their own way of thinking. This doesn’t mean you shouldn’t have a well-formed point of view, but it means you should consider your point of view as temporary. We started by building a consumer app, which had us obsess over every single detail in every single item of clothing as we were building our technology. But we ended up changing our mind on the go-to-market when we realized that our product can create a deeper impact at the root of the industry.


I had the pleasure to interview Purva Gupta. Purva is the co-founder & CEO of Lily AI, an emotionally intelligent AI platform for commerce. Lily AI claims some of the most iconic brands and retailers in the world as customers, has raised money from A-list investors and won many awards, like the best startup at the 2017 SXSW pitch competition. Purva is an immigrant founder who has been on 6 visas in last 4 years to live her American dream, has spent 10,000+ hours asking women ‘why’ they bought the clothes they bought and is now fearlessly building a product that will give an emotional & contextual upgrade to retail.


Thank you so much for joining us! What is your “backstory”?

I started my career working with ad agency Saatchi & Saatchi, where I discovered early on that beloved brands have the ability to create an emotional connection with their customers. It’s about how they make their customer base feel. Then I worked with a mobile banking and payments startup in India that made me fall in love with the concept of creating products that change people’s lives forever. My life’s goal became to land in Silicon Valley and fall in love with that one problem I would solve, but at 26, I felt like I was running out of time to make enough dents in the world.

Eventually I found my problem to solve: to understand the shoppers’ emotional context. However, all the odds were stacked against me: First-time, female founder, non-technical, without background in retail or psychology, away from my husband (who was then on the other coast) with no savings and no visa that lets me work in the US. I was intimidated in the beginning, but imagining what the promise land would look like with my solution always gave me the strength to take another step forward. I am so glad I didn’t let any of it stop me and I went against the flow.

Today, Lily AI has built the deepest image recognition technology in commerce, which powers the first-of-its-kind emotionally-intelligent AI platform. Our solution is not just able to understand every consumer’s emotional context and cognitive attributes when they come to a storefront, but it also helps the biggest names in retail make most of their retail functions smarter by better understanding every single customer.

Why did you found your company?

Four years back, I experienced New York City and fashion in a way I’d never experienced before in India. When the excitement settled down, I became conscious of how broken the shopping experience was. It was unintelligent for sure, but it also lacked empathy. Just because I can’t find anything in the store, I leave the store thinking that there might be something wrong with my body or my preferences. Even when I find it, I end up returning a lot and adding more frustration.

I decided to study the problem thoroughly by asking other American women how they felt about the entire apparel shopping experience. Since I am a feelings person, I realized early on that I identified a massive opportunity in the current fashion-buying experience, which can easily be extended to all of retail.

Fundamentally, we are building a technology that tries to understand why people make the decisions they make and I find it incredibly exciting.

What is it about the work you’re doing that’s disruptive?

Lily AI is the leader in creating emotionally-intelligent experiences in ecommerce. The first application of Lily AI’s emotionally-intelligent technology is in personalization, with the vision of exposing the intelligence platform to the entire retail value chain.

Emotions explain the ‘why’ behind consumer buying decisions, unlocking wallet share. Retail has saturated behavioral and demographic data (i.e., what, where, when) but those that understand the emotional data (why) stand to win in a customer-first market. Starting with apparel, Lily AI decodes consumers’ emotions and self-perceptions (extracted from consumer clickstream using emotional intelligence technology) and identifies 15,000+ product features (extracted using industry-leading deep learning and image recognition technology) to match individual consumers with the right products instantly. The outcome is a significant increase in ecommerce conversion rate, CTR and keep rate. Simply put, we’re trying to understand psychographic data about every consumer to re-create their mental model, so that shopping experiences can be truly delightful & relevant to each consumer.


We all need a little help along the journey — who have been some of your mentors?

I consider myself extremely lucky on this front. I came to Silicon Valley with literally two good connections, but I’ve had the pleasure of learning from some of the most successful CEOs and COOs in the Bay Area as my mentors & investors. My weekly interactions with them let me continuously challenge the status quo and get to the next level. My journey couldn’t have been what it has been without the guidance of my mentors. I crave to be with people who can challenge my thought process and constantly push me, so I emerge with more clarity than before about the decisions I’m making. Again, I believe I’ve been super lucky in this department.

That said, one of the biggest source of guidance for me, on a daily basis, is my husband. While an entrepreneur’s journey is hard by definition, having a partner that can help you along the way mentally and emotionally is a true blessing. Every day presents itself with a new challenge, and a founder’s job is to retaliate with double the force every day. My relationship with my husband becomes my true strength on particularly stressful days, giving me the emotional confidence required to deliver in the face of uncertainty.

Lastly, I have the privilege of sharing a deep relationship with my co-founder and partner in crime. While I learn best practices on leadership from my experienced mentors and investors, I get granular feedback on execution as a leader from my co-founder, who stands by me at every step. We’ve developed a strong relationship of mentoring each other through frequent feedback loops and transparency, which has led to significant improvement in our respective leadership styles. As a result, transparency and constantly helping each other succeed are two very important pillars of Lily AI’s team culture.


How are you going to shake things up next?

By opening up the Lily AI intelligence platform for the entire retail value chain to build on top of. From personalization of the digital storefront, to the buyers making decisions every season, everyone will be able to leverage their customers’ individual ‘why.’ We aim to not just become a standard in retail, but to help the industry upgrade itself to truly understand every consumer they serve.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

  1. Until you don’t ask, the answer is certainly no. Before applying to SXSW, we felt like we may be too early to apply. But one of our investors, Nitin Pachisia, pushed us to drop that thought and just apply, even if it was in the last few hours before deadline. We won the SXSW pitch competition as the best startup in the Social & Culture category 2017. This is a very simple principle, but I feel it takes time to truly internalize it. Every now and then, I find myself overcoming a different type of mental block and believing in these words at a new level. My job is to give my best and the rest is for the universe to figure out.
  2. Don’t be afraid to challenge your thinking or change your mind. I’ve learned from my mentors that it’s perfectly healthy — encouraged, even — to have an idea tomorrow that contradicts your idea today. The smartest people are constantly revising their understanding and reconsidering a problem they thought they’d solved. They’re open to new points of view, new information, new ideas, contradictions, and challenges to their own way of thinking. This doesn’t mean you shouldn’t have a well-formed point of view, but it means you should consider your point of view as temporary. We started by building a consumer app, which had us obsess over every single detail in every single item of clothing as we were building our technology. But we ended up changing our mind on the go-to-market when we realized that our product can create a deeper impact at the root of the industry.
  3. If you’re not thinking back to who you were a year ago and grimacing, you’re not growing fast enough. True failure is when you stop trying to do something because of fear of failure. Letting ourselves make mistakes is the essence of learning, in any aspect of life. In fact, I believe failing fast is the best way to move fast. Personally, I try to channel my inherent restlessness and hurry to the finish line by looking back on how far we’ve come. I’ve comfortable grimacing on myself. I find a lot of inspiration in JFK’s moon speech: “We choose to go to the moon. We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard, because that goal will serve to organize and measure the best of our energies and skills, because that challenge is one that we are willing to accept, one we are unwilling to postpone, and one which we intend to win, and the others, too.”


What’s a book/podcast/talk that’s had a deep impact on your thinking? Share a story with us.

Billionaire investor Ray Dalio’s Principles: Life and Work. I have found SO MUCH inspiration in that book especially around decision-making. I often ask myself these questions: 1. Can you simplify this seemingly complex problem into just another one of those? Have you seen this before? 2. All decisions should focus on increasing expected value. Can you increase probability of being right? 3. Seek people with experience who can help you triangulate to truth. Who’s done this before and is more likely to be right? Who has had success here? 4. Making mistakes is ok — It’s ok to be wrong. It’s not ok not to learn from them 5. Be radically open minded — Don’t let the fears of what others think stand in your way. Seek truth and diagnose problems to their root causes. You are looking for the best answer, not the best idea you came up with.

Stanford University psychologist Carol Dweck’s book Mindset has had a deep impact on my thinking. As a 4th grader, I developed acute stammering due to an inferiority complex of moving from a small town to a big city of sophisticated people. I struggled for 8 years to overcome my mental barrier, insecurity and feeling that I’m not good enough. This book helped me as I started to condition my mind to feel more confident and started to realize the power of my own mindset to overcome my mental block.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

Satya Nadella. In the last four years since he’s been in charge, Microsoft’s market value has increased 130%+. More importantly, the company is now making products that feel more user-friendly, empathetic and collaborative. Nadella also preaches the importance of empathy and making products that work reliably, traits that deepened in him when his first child was born with brain damage and his son’s life depended on linked machines running Microsoft systems. He’s had one of the toughest jobs in the world and is a leader who is unbelievably empathetic. It would be my honor to sit with him, as one of my greatest role models.

How can our readers follow you on social media?

LinkedIn: https://www.linkedin.com/in/purvagupta/

Originally published at medium.com

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