Where Are They Now: Diddo’s Rishi Nair & Pamela Chen

Founded by Rishi Nair (NYU Stern), Pamela Chen (NYU Stern), and Ryan Sullivan, Diddo competed in the Tech Venture Competition of the 2022-23 NYU Entrepreneurs Challenge, making it to the Final Pitch-Off. The venture’s API seamlessly blends the online streaming and shopping experience, allowing users to quickly and easily find and buy clothes and accessories worn by their favorite characters and personalities.

It’s been a whirlwind of a year for the venture and its founders, filled with growth for their product, team, customer base, and funding, with the team recently securing $2.8 million in backing. Between their meetings, accelerator programs, and speaking opportunities, the team found time to stop by the Berkley Center. We were incredibly fortunate to sit down with Rishi and Pamela to hear about their entrepreneurial journeys since finishing the NYU Entrepreneurs Challenge!

Q: Can you tell us a bit about Diddo? What does your venture do? What is your origin story?

RISHI: What we’re trying to do here is remove the friction between consumers and the culture that they see on screen. We want to make any video into a point of sale. Our API seeks to do what Stripe was able to do for static commerce, but for the video and social commerce world. For our origin story, we actually started this to solve a problem for Ryan and my mother’s reality TV shows. Reality TV is massive for both of our moms. And when Selling Sunset came out about a year ago, they were calling us pretty much every day asking where Chrishell got her dress or someone got their shoes. And at some point, we’re like, okay, this needs to be a thing for you guys. We have this strong feeling that culture comes from what we see on screen. We’re seeing that with Instagram influencers and social media day, but even before that, everyone wanted to be James Bond. That was a big thesis behind the idea.

Q: How did you find out about the NYU Entrepreneurs Challenge?

RISHI: Professor Franklin’s been a mentor of mine since my first venture into entrepreneurship, and she’s been a great support system. When we were telling her about the early ideas of what we’re building here, she brought up the NYU Entrepreneurship Challenge. Professor Franklin is actually how Pamela and I met; we were both in her virtual Startup Lab during COVID. 

PAMELA: Speaking to that, you know how the tone of a class can sometimes change the way you think about a topic? Professor Franklin’s class left a very positive connotation on entrepreneurship and the possibilities and the process of becoming an entrepreneur. That resonated with both of us enough to bring us to where we are now.

Q: Building off that, what motivated each of you to become an entrepreneur?

PAMELA: I think I always knew I wanted to be an entrepreneur. Growing up, my whole family feels like it’s a line of entrepreneurs: my grandfather, my dad, all my aunts, everyone. So it was kind of driven into me when I was younger. My first foray into any sort of career was when I was a sophomore in high school, and I just kind of wanted to get real-world experience. This was back in 2014 or 2015, and my first internship was at a blockchain startup, working out of a random apartment building with classic whiteboards all over the place. I just fell in love with the lifestyle and the possibility of planning and innovating for the future.

RISHI: My parents immigrated here; both were engineers, and they instilled in me the belief that if you want something done, you can put in the work and make it happen yourself. Living in the Bay Area, you see people who want a specific thing, so they’ll just build it themselves, and then they find that other people also want that as a product. Growing up in that environment was really great. My first foray into entrepreneurship was actually in third grade. I created a fun little comic book about a chicken and just started selling them on the playground for a quarter. Much later, I spent some time working at eBay, and I learned a lot, but the main thing I learned was that I cannot work at a big company. Working in a large pre-built system is not for me.

Q: Pamela, what's been your experience navigating the entrepreneurial ecosystem as a female founder?

PAMELA: Being a female founder is definitely a bit daunting; it’s clear that you’re the minority. But I think my co-founders and I have created a very healthy dynamic. It was a bit of a leap of faith in the beginning; we started the company without ever really meeting in person. But I think it really helps just feeling like I belong in the co-founding group. I feel very believed in and respected in my decisions. We went through a really, really great accelerator last summer called Neo, and it was great being surrounded by so many strong female founders. It helps to have examples to look up to and people who can relate to what you’re going through.

Q: Beyond being a female founder, you are also the CTO for Diddo; how has it been coming into the role of a technical lead?

PAMELA: Building on the last question, I think having a good support system is a huge part of being a technical lead, and I’ve found that with other female CTOs that I’m friends with. I think for any technical person there is this element of imposter syndrome that you have to deal with. You have those moments where you feel like “I don’t know enough.” Part of it is just personality, but it also was like I had just thrown myself into the deep end. A lot of strong technical leaders are older males. As a young female, I think it’s just about establishing that sense of credibility and that sense that you can be a leader. It’s just something you build over time, and it has to come from within, but it also comes from people around you.

Q: What were Diddo's major milestones before the Entrepreneurs Challenge?

RISHI: We were a pretty young company before the NYU Entrepreneurs Challenge and only incorporated in March 2023, which was the tail end of the Challenge! Our big milestones at that point were mostly around testing out the concept. We launched as a Google Chrome extension and timed the release to coincide with the first season of The Kardashians. We saw some really promising numbers that gave us confidence in the idea.

Q: How did the experience in the Challenge help Diddo with moving forward?

RISHI: I think one of the biggest things here is that our company is really media-focused, and one of the biggest things in media is connections. We were so lucky to get paired with Rob Sussman as one of our advisors through the NYU Entrepreneurs Challenge. Rob has a really strong network and understanding of the media ecosystem, having founded and sold both Sundance and Epix. He’s helped us so much with our journey, and he’s actually transitioned to be a full-time hire at the company, serving as Diddos’s COO.

Q: Do you think your time in the Challenge helped your personal growth as founders?

RISHI: 100%. I think there was a lot of personal growth from just being able to talk to the other founders and entrepreneurs in the Challenge and getting to grow closer as a team, especially with Pam. Ryan and I met in our freshman year of college, but before the Challenge, we hadn’t met Pam in person yet. Having the resources to continue to develop the venture also helped to build a company culture. We were able to walk away with a belief in Diddo but in each other as well.

PAMELA: Just having the chance to be part of the Challenge and NYU networks has been a huge help. I remember when we were first testing out our computer vision strategies and features that we wanted to build, we reached out to computer vision professors, and for the need validation on the market media, we reached out to media connections here. Professor Franklin has also been so supportive; the fact that she was so excited about our idea and what we had made so far was hugely validating for us.

Q: How do you think starting in a remote-only environment impacted your approach to the company's development?

RISHI: It helped that we met when we were on the other side of the world from each other. We had been able to do it as part of school, and now we were doing it in a professional setting. It also forced us to get on the same page about exactly how we were starting and what we needed to do to make it work. We’re working to build a generational company, and it’s really, really cool to see.

PAMELA: For me, the distance helps a bit with our separation of responsibilities. It would be hard for me to have my primary engineer and me in completely separate time zones, but Rishi and I are working on different parts of the company. We’re able to collaborate remotely and focus on what we need to do. The culture at our company also helps; we have similar interests, and there’s no real tension, so it works. Meeting at NYU also helped us create a strong ecosystem for staying connected.

RISHI: I also think communication is a huge part of it. A big thing for all three of us, just personally, is how we want our relationships to be, and its hyper communicative, and that translated well to our office environment.

PAMELA: Yeah, absolutely. In every co-founding team, you need to be able to test how you can resolve disagreements and conflict. I know Rishi will tell me like it is, and I’ll tell him like it is, and we both know it won’t be personal and our third co-founder, Ryan, helps balance us out.

Q: It's been a busy year for Diddo since the NYU Entrepreneurs Challenge. Are there any major milestones you're most proud of?

RISHI: There’s been a lot! Starting from the top, I think Pam’s done an absolutely incredible job at building out her technical infrastructure and architecture and starting to lead the way in terms of creating the culture for our technical hires to follow. She has led the company in an unreal way, and I’m super proud of her for that. For the company in general, it’s been huge to continue to bring on someone as storied as Rob Sussman. I kicked off 2024 by speaking in Davos while we also were securing two large customers. We were super, super excited about finishing up our round of raising and being able to go back to being heads down and scaling. It’s been a whirlwind, and I couldn’t be more proud of the team.

PAMELA: In every company, you need a CEO who has a strong vision, keeps the morale and energy up, and keeps everything moving in the focused direction, and Rishi is nothing if not focused. We are also VC-backed, so our pre-seed and seed rounds have been a huge lift on Rishi. But our team can go into these things feeling extremely confident because of him, and of course, him speaking at the World Economic Forum, I mean, that’s huge!

Q: What's the one thing you would tell a founder who's working to take venture from idea to an actual operational startup?

PAMELA: As a technical founder, this is actually quite a relevant question! For any technical leader who wants to take their idea from something conceptual to fully operational, you need to be organizationally minded. In a way, you have to be able to see into the future. My role at the company is about creating and designing the infrastructure and being able to remember all the key details of it. I have to be able to be flexible with it and change it as the roadmap shifts depending on the partners, the clients, and the product vision. You need to be clear in your mind, make sure to document everything, and realize that’s your responsibility because if you don’t do it, no one else will.

RISHI: Echoing what Pam said, you have to take what you put into practice and put it on paper. There’s always going to be an excuse not to; there’s always going to be another study that you need to do before you run something. It’s never going to be perfect. Startup ideas are a dime a dozen; execution is everything.

Q: What one piece of advice did you receive that has had the most impact on your entrepreneurial journey?

PAMELA: I don’t think it’s advice, but way back in high school I heard that the average entrepreneur fails seven times before succeeding. That gave me a positive outlook on failure because I’m like, okay, great, if I fail, then I’m one failure closer to succeeding. So whenever we’ve been in a rough moment where we’ve hit a roadblock, or someone says this is not going to work, I have the mentality like, great, like this is one of those potential failures. Now I’m one step closer. It’s a mindset shift, where while failure should be avoided, you don’t have to fear it.

RISHI: When I was growing up, my basketball coach said, “Control what you can control.” There’s so much that can go out of your control with a startup, but you have to focus on what’s internal, what you’re building, what your team’s doing, and block out the noise. There’s so much noise, especially with what we’re building. It’s not a new idea; shopping for what you see on TV existed before the Internet. QVC is a great example of a first iteration of what we’re trying to do, but how we’re going about it is different. As you can imagine, there are a ton of different people saying that people have tried this. There’s so many notes, there’s so much noise. It is incredibly important to block out the noise and control what you can control and turn it internal and have that camaraderie with the team and that belief in ourselves.

Q: Do you have any advice for aspiring entrepreneurs?

PAMELA: I’m biased because this is my dream job, but it’s exactly what you think it’s going to be, but also nothing like you think it’s going to be. It will be a lot of work. It will challenge you in ways that you haven’t been challenged before because all the initial validation will have to come from yourself. Your startup becomes your baby, and your co-founders become your co-parents. So, you have to really manage those relationships and learn how to be self-motivated. But it can also be incredibly rewarding, and I wouldn’t trade it for anything in the world. So I’d say enjoy it, and good luck!

RISHI: Team and personal relationships are some of the biggest things you should think about. We’ve seen a couple of companies that we thought were absolutely incredible that have crumbled because their team dynamics were not thought through and strong enough. I had mentors in the past who were CEOs as well, and their biggest advice was to work with people who are objectively smarter than you, and I’ve been lucky enough to find two people who show me that every single day. I think we got lucky having three co-founders that work really well together.

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