With Saideep Gupta: “Leading is tougher than it looks”

Imagine being able to say, “hey Wing can you walk my dog and make sure the dry cleaning is picked up and schedule a meeting with the dentist for tomorrow and maybe also order a cake for dad’s birthday” — and voila — consider it done. Wing is really pushing the limits of what’s achievable and stepping into this […]

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Imagine being able to say, “hey Wing can you walk my dog and make sure the dry cleaning is picked up and schedule a meeting with the dentist for tomorrow and maybe also order a cake for dad’s birthday” — and voila — consider it done. Wing is really pushing the limits of what’s achievable and stepping into this new era of automation. Imagine what this can do for our differently abled friends, for our senior citizens, for working moms and dads, for the nurses and the doctors during this crisis, and for the millions others who need help, somebody that can just take some things off their plate. Well now — they have Wing.

As a part of our series about cutting edge technological breakthroughs, I had the pleasure of interviewingSaideep Gupta, CTO at Wing.

Saideep is a technology enthusiast, ambitious entrepreneur. and a passionate leader. As Wing’s CTO, it is his responsibility to lead the company forward with cutting edge technology and innovative solutions to add more value for Wing’s customers. Saideep and his team are at the forefront of AI revolution, always striving themselves to be better than ever before

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

Ever since I was a young kid, I have always been really fascinated with creating. I absolutely love to create and innovate, to use my technology to make the world a better place, and to find solutions that would usually be termed as crazy. Started coding when I was like 10 years old, very early trying to find simple and easy ways to learn and teach myself. I originally hail from India and grew up in a normal home with limited access to technology. I remember going to the computer store near my house and spend hours, just trying to use the internet, something that was new and emerging at the time, that nobody understood exactly, but everybody wanted to be on it. There was just this crazy drive to know it all, to click every possible link on google (trust me that list of links was shorter back then :D). My parents were amazed by this passion of mine and supported it with an unstoppable force. Their energy to push forward still drives me. And finally the day came — I woke up to see my dad standing next to a new computer. MY NEW COMPUTER. It was this huge and heavy box with wires going in and out of it and a million other things connected to it — would probably find it down the road at Silicon Valley Computer Museum :D. But yes. The computer was here and I was, unsurprisingly, jumping.

I think this one project of mine was the game changer — the sense of satisfaction was unreal. I must have been 13 or so. There was a major problem and I just had to find the solution. So problem — our water tank for the house would overflow every day as there was no way of knowing when it was full and cutting off the water pump. Can’t forget my mom’s face worried every day about how full the tank was. So I decided to do something about it. All I needed was 1 motion senser, 1 small bell, and 1 cheap arduino board (and definitely the box of a computer to write code on). Some 12 hours and 100 lines of code later — I had a solution — my mom would now get alerted by the bell ring which would get activated as soon as the water touched the motion sensor placed an inch from the mouth of the tank. Such a trivial solution to such a painpoint. By this point — I think my parents had seen me do everything from making them play the weird games I would code, or having them drive me to a hackathon 3 hours away, or even taking the computer apart and putting it back together. There was no turning back from that point on. So I think the water-tank-overflowing-sensor-ringing project is definitely at the top of my hall of fame :D.

Can you share the most interesting story that happened to you since you began your career?

Oh it’s interesting stories after interesting stories. Trust me, running a startup is a rollercoaster where you dont know whether the next move is up or down — you just go with the flow screaming with excitement and holding on :D. There’s definitely the occasional story of not knowing that we have a scheduled demo in the morning with a billion dollar fund and then spending the night putting the demo together — killing it always :D. But I think the most interesting story, for me atleast, would have to be from the early days of Wing, back at UC Irvine when Wing was just a baby. The big launch was coming up, we were in the deep end of development, working 80 hour weeks, while creating buzz around Wing. I remember in order to sustain our tech costs and marketing expenses, my co-founders and I would buy a bunch of cheap Costco pizza and sell it outside the bars down in Newport Beach — people coming out would be willing to pay upwards of 5 dollars for a slice :D. I think looking back to that and seeing how far we have come — that’s what makes it really interesting for me.

Can you tell us about the “Bleeding edge” technological breakthroughs that you are working on? How do you think that will help people?

My goal is simple — I want Wing to be able to leverage our highly advanced and skilled Hybrid Intelligence concepts powered by proprietary technology and be able to solve the toughest of problems, to allow us to be free of the boring and tedious tasks in life, and to spend time with the ones that matter most to us — our family and friends. We have gone to great lengths in order to ensure that everything we do at Wing is to enhance our customers’ lives and to add value at every step of the way. My teams are working towards further perfecting our systems thereby increasing our AI’s success rate — which could really open up the world at our fingertips. Imagine being able to say, “hey Wing can you walk my dog and make sure the dry cleaning is picked up and schedule a meeting with the dentist for tomorrow and maybe also order a cake for dad’s birthday” — and voila — consider it done. Wing is really pushing the limits of what’s achievable and stepping into this new era of automation. Imagine what this can do for our differently abled friends, for our senior citizens, for working moms and dads, for the nurses and the doctors during this crisis, and for the millions others who need help, somebody that can just take some things off their plate. Well now — they have Wing.

How do you think this might change the world?

Every tech entrepreneur likes to say that they want to change the world and that their tech will change the world. I guess at Wing, our ideology is more oriented towards maybe not so much as changing the world but rather more towards changing the way the world works. We still anticipate all the billions of things continuing to happen as is — you are still going to want to get dry cleaning and the dry cleaning shop is still going to do the dry cleaning, your cat will still need her food and the grocery store is still going to sell that food, and yes — you will still have your birthdays and anniversaries and will still visit your favorite places to celebrate — things are as is, but what we want to do is change the interactions and the processes of doing things. Rather than collecting all your dry cleaning from throughout the house, bagging it up, taking it down the stairs, stuffing it into your car, driving to the dry cleaner through a 30 minute bumper to bumper, maybe have to get gas on the way, and then arguing with the shop over rates and pickup date (oh and repeating most of this again when you have to go pick it up), why not just ask your friendly assistant 😀 “Hey Wing can you drop off the dry cleaning at the usual place and have it picked up? I need it before the end of the week”. Trust me — its that simple. And this simplicity is I think what makes it so interesting.

Keeping “Black Mirror” in mind can you see any potential drawbacks about this technology that people should think more deeply about?

Trust me, there is nothing terminatory in this technology. I think over the years, Hollywood has thrown such wild and vivid imaginary about this alter universe where AI has taken over the world, robbing us of the opportunity to see what it can do for us, the kind of wide scale benefits it can bring. I understand the concerns that all of us have, but I can assure you as a tech professional — we have designed and developed our technology from day 1 as a secure vault, investing numerous hours of engineering time to ensure safety of our customers’ identities and privacy of their data. Wing olds itself to the highest standard of security and as such we use the latest in-class technologies like Google Cloud’s Secret Manager to store user information (using banking level encryption) and Stripe enabling us to securely make purchases without exposing user payment data. Checkout our YouTube channel or even the website, we have a 10 minute long video explaining more things 😀

Was there a “tipping point” that led you to this breakthrough? Can you tell us that story?

Theres always that tipping point, that one moment when you feel it from within, like the entire universe is telling you to do it, like this is everything that you were working towards but did not know what it was — until now. We had that too. This goes back to our freshman year at UC Irvine. Karan and Martin, my two other co-founders, were roommates and I used to live across from them. We were all hanging in their dorm room this one silly night at like 2am when Martin realized that his parents were going to drop by in the morning. And the room was, for lack of a better word, trashed. Oh we were so worried. And hungry. We just wanted someone to get us some Jack in the box from across the campus. Oh, and clean the room too. We tried looking online for cleaners but no help. We even tried posting on our residential hall facebook group offering 20 dollars for cleaning help but to no avail. Oh, and still no food. This was a problem, one which we couldnt find a solution to. We even saw something interesting — our “Cleaning Help; 20 dollars” facebook post got a lot of comments — but not of people offering help but +1ing it as they wanted cleaning help as well. We began thinking — how many others wanted cleaning help, or food delivery, or a car wash, or homework help, or dry-cleaning pickup, or the tons and tons of other chores we all take on everyday. We were just a bunch of young kids with a desire to help I guess. That was where Wing was born — the tipping point of everything.

What do you need to lead this technology to widespread adoption?

That’s a very interesting question — something my team and I try to answer everyday. I would say its not a single entity or a 1-D model but rather a system of components that all work together to allow adoption. Wing works very hard to ensure the highest levels of quality service through next generation proprietary tech that has been battle tested. Wing’s business model is setup from a customer-first perspective — we rely heavily on our trusted partners (which also go through a rigorous onboarding process as well as internal rating algorithms) to render services to our customers. A hurdle that we at Wing are actively chopping away at is having qualified partnerships for our list of 100+ services in every corner of the country, and then eventually the world. As far as what can help enable adoption easy? Customer education. Most of us out there have never experienced having somebody always there to help, having someone who can take things off your plate, having an actual assistant. As a result — we are very used to doing everything by ourselves, without asking for help. But this is exactly what we eliminate through Wing. You now have this superhuman assistant with all kinds of superpowers to help you within the palm of your hand. Need groceries? check. Need to renew your car registration? check. Need to make a reservation? check. Need to cancel a reservation? check. Need your dog walked? check. I can keep going on and on. But this right here. What I am doing right now is exactly what we need for widespread adoption — for people to realize the potential we are offering at just 10 dollars a month (or 20 dollars a month for the plus plan) to have a personal assistant (which would otherwise cost thousands of dollars) to get anything done.

What have you been doing to publicize this idea? Have you been using any innovative marketing strategies?

Definitely. My marketing team is working round the clock — writing and pushing out articles on a whole list of topics to public forums as well in-house publicly-viewable blogs, increasing our social media presence on all platforms including instagram and tiktok, as well as coming up with new and innovative ideas for ad series that can be features on platforms like YouTube. I have in-house creative teams whose full-time job is to create more and more videos that allow us to educate our customers while presenting the value proposition in an entertaining way. We just created another great piece on one of our newer product offerings — Wing for Business. You can check it out on and click to play video. We are also doing alot of various different marketing campaigns including digital billboards, google ads, facebook ads, and a whole series around user testimonials and how Wing has been instrumental in helping them get through these past few months. We have also been receiving alot of media attention — Wing was just recently written about in Forbes as well as Business Insider. I just recently got published as well in TechPanda as well as StartupBeat magazine. So I would say we are definitely making a splash and seeing traction as well.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Couldnt agree more. I have always believed in the fact that my success has never been of my alone — but of all the people who have helped mold me into the leader that I am today, both personally and professionally. However, the most impactful person, or rather group, has been my family. Their support is the fuel to my fire. Their faith in my success has been nothing short of a blessing. Over the years, we have seen lots of ups and downs — trust me — running a startup is not easy :D. But they are always there to lift me back up during the lows, pumping me with the belief that success is right around the corner, and also always there to support and celebrate my wins. Their unending faith in me drives me. It always has. Oh, and it fills me with happiness when I see them actually using Wing. I built something to make their lives better :D.

How have you used your success to bring goodness to the world?

My culture we believe in goodwill, in the act of karma, and of giving. When COVID hit, Wing was one of the first tech companies to respond. We immediately launched a platform, “Wing in Crisis”, that was solely geared towards providing assistance to not only our users but to anyone visiting the platform, without any associated fees, by letting people post their needs and then our AI systems working to connect them to those goods and services. We had testimonials coming in calling us a “savior” as well as “essential”. I remember I myself was deep into the trenches. My engineering team and I spent 48 hours of nonstop development to code, test, deploy, and promote the entire product. We also geared our customer apps to offer COVID support including providing directions and information for the nearest relief center, sending supplies to your loved ones, arranging masks and other PPE items for yourself, as well as partnering with Postmates to offer fast and easy delivery of food and grocery. We also had our corporate partnership teams starting to look for more ways where we can be of support. And we found the answer. The frontline healthcare workers, the doctors and the nurses, were the ones under heavy fire and pressure during this time, risking their lives everyday to help the rest of us in need, and we wanted to help. Wing partnered with Kaiser Permanente as well as John Muir Medical Group to offer Wing absolutely free to all their staff. That was magical to see how much pain Wing could ease in these times.

What are your “5 Things I Wish Someone Told Me Before I Started” and why. (Please share a story or example for each.)

  1. I wish someone told me that “its not going to be easy” to chase your dreams, to actually become the next big thing in tech, and to achieve success. We are all so deeply invested in looking at the success that we never think about the grunt work and the long nights that go into achieving that success. There are days when you wont get to have a meal for 20 hours at a go cause of back to back meetings, when you would just lose a contract and the world seems to be crumbling down, and when it would seem as if all efforts are futile. You have to keep pushing forward and focus on the next day.
  2. I wish someone told me that “leading is tougher than it looks”. Being a leader at Wing, I have a lot of responsibilities on my shoulders, I have people who look to me for direction and mentorship, I have teams who are following a roadmap I have built, and I have stakeholders who have have entrusted their faith in me to lead the company forward. Part of being a good leader, as I have come to learn, involves not one but many functions — listening to your team’s concerns, creating an open work environment, trusting your team members that they are acting in the best interest of the company, trusting your gut as your decisions could impact the entire functioning of the company, and sometimes even acknowledging that you may not be right about something. Its fun 😀
  3. I wish someone told me that “team work makes the dream work”. At the end of the day, it is the team that has to stick together and make sure the trains keep moving forward. Running a company is not a one man show. People come together, form ideas, and that’s how you create a billion dollar company. As a founder it is important for me to make sure that the value of team work is something we set from the top down.
  4. I wish someone told me that “you have to focus on the big picture”. Running a startup and then leading it to become the next unicorn (or decacorn) is not about “I got us here” but “we got here” — that’s what matters, and something that I have learnt is that you cannot only focus on the small things. Celebrate the small wins definitely but dont make it an issue about who gets credit for that small win. That is the single most deteriorating thing to success. Everybody deserves to get their moment — if they have worked hard for something, then I make it my personal duty to make sure they get rewarded for it.
  5. And last, I wish someone told me “to never get emotionally attached to a product”. We are running a business and part of it is developing products for others, not just for yourself. Something that may fit perfectly into your world may not fit into the broader’s group’s world. And being able to accept the truth and letting go of something that you may have been working on for days — that’s I think the hardest challenge for a developer. It is never an easy call to make, but as a leader, sometimes even the toughest and critical of decisions are on me to take. Everything we do at Wing is to add more value to our customer’s lives and to make their lives easier.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

That is a really excellent question. There’s definitely something that I have been wanting to do for a while, and have even kinda undertaken in the past — I want to enable younger kids — between middle and high school — to pursue “something” in tech. There’s a specific reason i use the word “something” — its because most kids who might even be very interested in learning more about or even passionate for tech but may not know where to start or what to do. I think as young professionals and leaders of tomorrow, we have the power to have the most impact on them. I think these young adults are able to connect really easily with lets say someone like me. Late last year, in pre corona times, Wing actually organized a hackathon where we opened ourselves to all high schoolers as well as freshmen to come try their luck at winning a Wing internship. The quality of work that we see pursued by ambitious ideas was really empowering. Most of my colleagues will tell you how excited I get when a teenager applies to Wing for an internship role. One of my current interns, really brilliant guy — hes currently a high schooler, buy you will be amazed at what all he’s worked on, pushed entire projects to finish, in the past couple months.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Steve Jobs, one of the greatest of our times, somebody who I and millions others look upto, during his “Crazy Ones” speech said something that has stuck with me for years at this point. It was the tail end of his words, but the most impressionable ones — “the ones who are crazy enough to think they can change the world are the ones who do”. I dont know what it was about what he said, but it still fills me with a sense of drive. I think the reason may be that in my mind, I can picture myself as one of the “crazy ones” or as Jobs says, “the round pegs in the square holes, the ones who see things differently”. I am never the one to settle for the status quo, to accept things as is. I have always been a sucker for innovation and for bringing a change. Trust me, when we started Wing — it wasn’t all rainbows and stars (it still isnt :D) — we did meet with lots of criticism and push back — from investors, from friends, from professors, from colleagues, from incubators, from banks, even from strangers — things like “this wont work”, “can you really build this”, “why would this work”, “you will get crushed” etc etc. Earning people’s belief that what we are doing is not only going to work but actually become the next big thing was challenging, but it starts with believing in yourself. And I think those words really resonated with me. It was kind of like, “yeah you think I am crazy, wait till I change the world”. And here we are 😀

Some very well known VCs read this column. If you had 60 seconds to make a pitch to a VC, what would you say? He or she might just see this if we tag them 🙂

Imagine having a superhuman with you 24/7 to take things off your plate, to free you up of the mundane tasks, to have somebody always there that you can count on. Need groceries or food? done. Need your dog walked? done. Need someone to babysit the kids? done. Want someone to go wait in line for you at the apple store? done. You can literally get anything done with the tap of a button. We have had people ask us to book private jets, to buy homes, to get their parrot’s toenails cut, organize events, setup appointments, and anything else. Its like having thousands of specialized assistants jumbled into an app, powered by proprietary AI and technology of course. And for a fraction of the price — just 10 dollars (or 20 dollars for the plus plan) a month. If you are a wing user, you can access us through the mobile apps, through chrome extensions and the web, through slack, or even directly through text and phone. We launched February 7 on Product Hunt and were immediately crowned Number 1 globally — we had thousands of people visiting the websites and about 2500 requests flow through in the first 3 hours. Shortly after we became part of Berkeley Skydeck, one of the top accelerators in the country, and have been growing crazily ever since. We also recently just launched “Wing for Business”, a product geared towards small and medium sized businesses to help as an office assistant at only 1000 dollars a month (⅕ of what you would have to pay someone to do these chores) and have already onboarded many paying businesses. There’s so much more to talk about. Just shoot me an email or a LinkedIn message, and I would be happy and excited (trust me I get very excited talking about Wing — I am sure you can tell) about chatting further.

How can our readers follow you on social media?

Linkedin is definitely the best way. Am always down for a fun chat as well.

Thank you so much for joining us. This was very inspirational.

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