Forging on past failure, Suneel Gupta began to ask wildly successful people about their less-successful moments—and that laid the foundation for his own career highs, not to mention his new book that helps anyone with a great idea become Backable.
Transcript
Debbie Millman:
Do you have a great idea that you think will make a lot of money? Do you need to raise some serious capital to get your idea off the ground? Well, you’ve come to the right place at the right time because my guest today is Suneel Gupta. He’s the co-founder of the healthcare company RISE, and he helped turn Groupon from a pipsqueak to a multi-billion dollar company. More to our purposes here, he’s the author of the new book Backable: The Surprising Truth Behind What Makes People Take a Chance on You. He’s here to talk about that surprising truth and about the surprising twists and turns in his own entrepreneurial story. Suneel Gupta, welcome to Design Matters.
Suneel Gupta:
Debbie, it’s so good to be here. Thank you so much for having me.
Debbie Millman:
I want to start by asking you a little bit about your mother. While this definitely an interview about you, I’d like to start by talking about her.
Suneel Gupta:
Sure.
Debbie Millman:
She’s really remarkable, are you OK with that?
Suneel Gupta:
Of course. Yeah. I love talking about mom.
Debbie Millman:
OK, so, in 1947, when your mother was 5 years old, her family was forced to move from their small village in India when the country had gained independence from Great Britain, but was divided into two countries—Pakistan and India. Your mom’s parents were well-to-do landowners who lost everything overnight when the rioting and looting broke out. They left on cargo ships in the middle of the night from Mumbai, where they were considered refugees. The family had no money, but your mom hatched a plan to get the family back on its feet. She studied hard in school, she made good grades and then, at 13 years old, the Prime Minister of India visited her city. She went to see him speak and he told the group that India needed engineers. At that moment, your mother decided to become an engineer. Something that was unheard of for women at the time.
Debbie Millman:
She went to college to study Mechanical Engineering at a college that didn’t have a women’s restroom. So like in the movie Hidden Figures, she had to bike one and a half miles just to go to the bathroom. At 19, she read a book about Henry Ford and became obsessed with assembly lines and Ford’s dream of bringing the car to the average person. She started dreaming of coming to the United States and working at Ford. She then left India in 1965 at 22 years old. She travels first to Germany, then to Stillwater, OK, where she studied engineering before getting a job at Ford in 1967. That same year, your mom’s car broke down outside Ann Arbor. So she found a telephone booth and searched the phonebook for the most common Indian name she could think of.
Debbie Millman:
The guy who answered was Subhash Gupta. They were married within a year and had two sons, your brother Sanjay and you. So my first question for you, Suneel, is this: Is it true that the word impossible was not allowed in your house in your upbringing?
Suneel Gupta:
Well, just even hearing you … it’s funny, and I grew up with this story, and just hearing you just say it, Debbie, it gets me emotional. Yeah, the word impossible was not allowed in our house. We were always sort of asked to figure it out. Whatever it is that we wanted to do, figure it out. It’s funny, I always sort of remember these stories about mom, and I have been more as of late, as she’s getting a little bit older, where I’m trying my best to spend as much time as I possibly can with her. And there are these moments that are just … I will all of a sudden think of, and one of them was, I remember in third grade I had a social studies teacher who I loved. Her name was Mrs. Canauer. I will never forget when Mrs. Canauer played some of the footage of John F. Kennedy’s inaugural speech.
Suneel Gupta:
Then, after she showed us the speech, we learned about John F. Kennedy, but one of the things she said was he didn’t necessarily write that speech himself. He had a team working with him, and I remember thinking to myself, Wow, that would be really cool to do someday. What if I got a chance to write for somebody like a John F. Kennedy. I remember racing home and telling my mom, “Hey, mom, when I grow up, that’s what I want to do. I want to write speeches.” I remember my mom looking at me and saying, like, “Why are you going to wait until you grow up? Well, just go do that now.” So, I did, I started to ride my bike to the offices of local politicians, and I would ask them if I could write speeches for them. Of course, most of the time, they would say, “look, we’d rather have you stuff envelopes or go knock on doors.”
Suneel Gupta:
Every once in a while somebody would be like, “Yeah, sure, once you put some thoughts down on paper,” and it just sort of built from there. There was a congressman passing through my hometown in Novi, MI. His name was Bart Stupak, and I knew he was going to be at a certain hotel giving a speech, and I knew he was going to be talking about healthcare. I was, I think, 16 years old at the time, and I drove my car to the hotel with this speech in hand, waited for him in the lobby. When he walked into the lobby, I cornered him and said, “Hey, I’ve got some remarks prepared for you tonight.” Completely naive about the idea that like, of course, I mean, he’s giving the speech in the next 15 minutes. He’s got his remarks. He doesn’t need my stuff. I’ll never forget the look of the person who was traveling with him as well, just looking at me, like, “Who is this kid?” Stupak, he just stares at me blankly and he says, “What’s your phone number?” I gave it to him. It’s my home number, not to sell or anything like that. A year-and-a-half later, I get a call from the White House. It’s somebody who’s part of the internship program over there. He says, Congressman Stupak recommended you a while ago; you’ve been in our files for a long time, and how would you like to come do some writing with us this summer? So, yeah, it’s weird, Debbie, but getting back to your question about the word impossible, no, just looking at her story, it was difficult to ever sort of go to her and be like, “I can’t do something.”
Suneel Gupta:
Even more than that, there was always … so she pushed back with, “OK, well, why not at this moment, because we had no idea how life is going to unfold and what’s going to come ahead.” I think that’s the refugee mindset in a lot of ways, which is this sense of impermanence but also possibility. So there’s a sense of urgency that I think comes with everything, right? Don’t take anything for granted. If you want it, then find a way to make it happen sooner rather than later.
Debbie Millman:
I’ve only had two instance over the 16 years I’ve been doing this podcast where in researching my guest, I thought, Wow, I really want to interview this guest’s mother. Actually, no, three times. Three times it’s happened. It’s happened now with Julia Turshen, and I did indeed interviewed her mother, Rochelle Udell, who was a major, major force at Conde Nast for a very long time, and really changed the field of art direction. Lucy Wainwright, whose mother is one of the Roche sisters, so absolutely wanted to do that, and hope to still someday, and now, you. I have an open invitation for your mom to come on Design Matters anytime.
Suneel Gupta:
My mom would love that, and she’s so great at telling stories. She will definitely come on this show.
Debbie Millman:
Wonderful, wonderful. Well, one of the things that you’ve said was … the most important thing that she taught you was the relationship between action and courage. I thought that was really fascinating, and I was wondering if you can share that today?
Suneel Gupta:
Yeah, because I always felt like in order for her to do what she had to do … how do you muster up the courage to do that? How do you … where do you get the resolve to say that I am living in a refugee camp, right, we are living on rations. Yet one day, I’m going to move to the United States and I’m going to become an engineer with Ford Motor Company, right, which at that time was the company of its day. Where do you get that, and where do you get the courage to sort of proceed with a plan like that? And I think that the thing that I misunderstood was that courage leads to action, right? You build up enough courage, and once you cross a certain threshold, you can act. If I unpack my mom’s story, it really is the other way around.
Suneel Gupta:
She acted, and because she acted, she built some courage along the way, and with that little bit of courage, it led to more action, which led to more courage, and it became this cycle, this engine that sort of propelled her forward. What I do today is I spend time studying extraordinary people, and what I found is very much the same pattern, which is that it didn’t really start with, “Let me go away for a while, build a bunch of courage and then act.” It was more kind of like, “Let me just act and then figure it out along the way,” which I know we hear so often, but when you see your own parent, when you see their own stories sort of unfold that way, I think it hits you in a different way.
Debbie Millman:
Suneel, you’ve written about how you grew up in an almost boringly safe suburb, never experiencing anything close to the conditions your mom did, but somehow, you and your brother both inherited her refugee mentality, something you’ve described as a strange mix of impermanence and optimism. I’m wondering if you can also share a little bit more about what that means?
Suneel Gupta:
Yeah, there can be a sense of anxiety that comes, I think, with the refugee mentality, because I think in some ways, it’s sort of this feeling that you’re going to lose everything, right? At the same time, I think the positive, which I think was a huge, huge net benefit, was the sense of, “Well, then anything is available.” It’s almost like this sense of, if you have nothing, then everything is on the table. I think in some ways that is … you mentioned in the beginning the speech that my mom heard when Jawaharlal Nehru, India’s first prime minister, was basically trying to rebuild the country, right? Trying to figure out, now, the country had gotten its independence from Britain. What do we do now? We’re very, very poor. The economy’s in the shambles. Mahatma Gandhi had just been assassinated and Nehru, always, I think, envisioned that Gandhi would be by his side, and they would sort of be figuring this out together. Now he didn’t have his partner. But I think that the thing that she talks to me about when she heard that speech was a sense of, let’s move in whatever direction we think makes sense. Nothing is anchoring us anymore, and in his case, it was, “Hey, why don’t we really invest in math and science and design and creating things and building things? Let’s go do that, right? Why not?” I think that that’s really that sense of impermanence and optimism that you never lose. She brings it into her own career and, yeah, my brother and I are … we were born and raised in suburban Michigan, the conditions were completely different than anything she had ever experienced before. Yet at the same time, when you’re raised by someone who’s been through that, you can’t help but sort of, I think, pick up a little bit of that grit.
Debbie Millman:
Despite the optimism, you’ve talked about the isolation of growing up as one of very few brown skin kids in your neighborhood, and your dad called your family “raisins inside a tub of vanilla swirl ice cream.” What was that like for you?
Suneel Gupta:
One of the decisions that my parents made that always sort of puzzled me was that there were areas of Michigan where there were lots of Indian folks, and yet my parents decided to move to a place where there were literally none. It was just us when we moved there, and I was always puzzled by that—like, why? Especially, I think, as my brother and I got picked on a lot. You’re bullied a lot for that reason for having brown skin, we would ask her, like, “What was behind that decision?” Her response was very much just, “You have to figure this out. If you think that the answer is to go be amongst people who just look like you and think like you, talk like you, that’s just not the way that life works. And either you’re going to learn that lesson right now or you’re going to learn it later on. I’d much rather be here with you as you learn that lesson.”
So it wasn’t easy all the time, but I feel like we kind of did it together as a family. We would talk about it. I think the hardest part, honestly, for me, was … when I talk to people who I think have gone through sort of being different or feeling like the outsider based on the way that they look, one of the things that I often pick up is that there tends to be an age where that doesn’t matter, and then, all of a sudden, you get to an age where all of a sudden it seems like it does. For me, that was in 1991, because in ’91 we went to war with Iraq. This was Desert Storm, and it was exhilarating for the kids in my class, especially the boys. It was an exhilarating moment because they’d never seen anything like that before, right, and all of a sudden now on television, we’re watching this war sort of unfold, short war. It happens to be that the people who we’re sort of going to war with look a lot like me. I think in some ways, people felt like it was their patriotic duty to sort of give the brown kid a hard time. That’s when it got a little bit rough.
Debbie Millman:
Yeah, how did you manage?
Suneel Gupta:
I managed a lot by, I think, learning to just kind of be by myself. I think being more comfortable with that, which I don’t necessarily look at that as a bad thing. I do look back on those experiences and feel like … I wish it would have been a little bit different for that kid, but I also know that because I was able to find, I think, some sort of grounding, some centering by myself, I think that it just served me very well. I’ve been able to come back to that place through other things that have come up. If you look at my sort of bio on LinkedIn, you’re going to see the success, but you’re not going to see all the failures, and there are many of them. It was during those moments where I think there’s a lot of value of being able to come back to yourself, and learning that at an early age was a gift.
Debbie Millman:
I love the way you look at it. It is really quite optimistic. So I see your mother’s influence there for sure. You earned a Bachelor of Science degree from the University of Michigan, and then took an IT job in downtown Detroit, and you’ve written this about the experience: “The pay was decent, but each day was the same as the last, troubleshooting issues, building spreadsheets and maintaining databases. It was simple, mind-numbing work.” Then, you go on to describe how you were waiting for someone to point in your direction and say, “that kid is a star. Let’s find a better way to make use of his talents.” But it didn’t happen, and in the sea of cubicles, you sat at your desk waiting to be discovered. I have to tell you, Suneel, I’ve often heard about people sort of waiting to be discovered. I remember somebody very close to me describing how she was waiting to be discovered because she had ballerina feet, and she was waiting to be discovered as a dancer. Why do so many people do this? Why do they hope and wait and maybe expect that they will be revealed to the world?
Suneel Gupta:
Yeah. Such a good question. When I was in graduate school, I had this marketing professor who said something that I just … I don’t know why, but it just really stuck with me. What she said was … on the first day of class, she said, “I pay attention to the exams, of course, but I also really pay attention to the way that you engage with the class. That really matters to me.” She said, “You know what, you might be brilliant but if you don’t say anything, then I won’t have any idea.” That just stuck with me, because I think it’s true. I think in a lot of ways we’re sort of waiting to be called on before we sort of speak up, and I don’t know why we expect it. I don’t know necessarily why I expected it. I think it is a very privileged position that I try not to take any more, privileged posture.
Suneel Gupta:
This idea that like somebody is going to say, “Hey, you know what, we’ve been underutilizing that person. I bet you that person is very brilliant over there.” The one thing I hear very often from the students that I work with is, “I’m not having the impact that I want to have, right?” In order to have that impact, they’re sort of waiting for somebody to say, “Hey, let’s put you in a position where you can have impact because we think you can do so much more.” So, we get stuck in that position.
Debbie Millman:
When you were in that position, you did what you described as what a lot of people do when they feel directionless: You decided to go to law school.
Suneel Gupta:
Yeah.
Debbie Millman:
No offense to any lawyers that really love practicing law, and I know a bunch. Were you at all excited about becoming a lawyer at that point, or was it one of the, “I have to be a lawyer, a doctor, an engineer,” kind of moments?
Suneel Gupta:
It definitely was a, “Let me go do something that I feel like might make my parents somewhat proud.” I kind of knew in the back of my mind that, no, I don’t think I want to practice law, because to your point, there are so many people out there, especially I met in law school, who are all about that. That’s what they wanted to do. They had a passion for that. In Hindu terms, that was their Dharma, but it wasn’t mine. So when people started to look for work, I started to look in very unconventional places, and I started to set my eyes on, could I go out to a place like Silicon Valley where people are making things, people are building things, and be a part of that?
Debbie Millman:
You also got an MBA from the Kellogg School of Management. So, in looking at your timeline, I know you did like all of your education in six years. Were you doing your MBA and getting your degree in law concurrently?
Suneel Gupta:
Yeah, yeah, so Northwestern had, at that point, recently rolled out a program where you could do an MBA and a JD in three years. So you spend your first year in law school and then your second year is predominantly at the business school, and then your third year is at the law school again. So it’s pretty condensed, but the nice thing is that you do it with a group of people. So I had 15 or so people who were doing the exact same program with me. So even though it was tougher at times, you never felt alone.
Debbie Millman:
You were sworn in by Justice Roberts to practice law in front of the United States Supreme Court. As you were finishing your degree, you received a job offer from what you’ve described as a chest-thumping corporate firm based in midtown Manhattan. The signing bonus itself was twice the salary you were earning in Detroit. You got a sinking feeling that taking that job would send you back to the same headspace you were in before you went to law school. So you turned down the offer and began cold-calling people in Silicon Valley. You just mentioned that that became interesting to you. What about the atmosphere in Silicon Valley, and the work that was happening there, was intriguing you, especially after spending those three years studying law and business administration?
Suneel Gupta:
Yeah, I think it very much was about creating something from scratch, as you’ve talked about on the show a lot, the difference between building something from zero to one versus just optimizing what’s already there. For me, there’s nothing wrong with optimizing, by the way. There are people who do that very, very well. I guess I’ve always kind of been the kind of person who’s sort of has felt like, what’s not out there right now that could be out there? And it’s just not the way that I was finding that, certainly law firms, tend to think, right? We’re working with established companies, we’re working with established clients that need to solve a very specific problem in order to make their business just a little bit better, or to de-risk it just a little bit more.
That just didn’t appeal to me as much as this idea of like, what can we build? What can we do? I had such admiration for people who wrote lines of code, who built things, who were able to do that. I was also just getting a keen awareness … iPhone had just launched right around the time that I was starting to prepare to graduate. I thought to myself, gosh, things are just getting created so quickly now. If I compare sort of what’s happening now to the way that my parents work … my parents were both engineers. They both worked for Ford Motor Company, and I remember, they would work on projects for years, like literally years, before anybody would ever take a look at their work. I still remember driving to the auto show that took place in Detroit every year.
It was like my dad would tell me, “Hey, inside that car is a part that I had been working on now for like three-and-a-half years, and today is going to be the day that we sort of unveil that.” What really fascinated me about what was happening, I think, in tech at the time, was like, people were literally developing things during a lunch break and posting their code and having it be used by the end of the day. That was intoxicating to me.
Debbie Millman:
I believe that your first Silicon Valley job was director of product development for Mozilla, the maker of Firefox—but I believe your first job out of law school was actually as a writer for MTV, for which you worked there, I think, for about a year. Is that correct?
Suneel Gupta:
Yeah. Yeah.
Debbie Millman:
Tell me how that fits in with this sort of life goal that you had at the time.
Suneel Gupta:
It’s always been a little bit weird, Debbie, and it’s always hard to sort of make sense of it myself, especially if I’m describing it to my family. They’re like, “Wait, what?” I’ve always kind of jumped back and forth between the worlds of writing, which I’ve always loved, and I spent time as a writer before I went to graduate school.
Debbie Millman:
Yeah, for the DNC, right?
Suneel Gupta:
Yeah, for the Democratic National Committee. Yeah. Then, when I was working at Mozilla, I wanted to … I still wanted to write, and MTV had this role where they were … where we’re creating something new around content focused on people with brown skin. I was kind of moonlighting that job while I was working at Mozilla. I felt like I was sort of scratching both my itches. I had the technologies, sort of more analytical side of the world during the day, and I got to do more of the sort of creative fresh type of stuff at night. The writing began in 2004; I got a job at the Democratic National Committee as a writer. One of the stories that is stuck with me, I think, in a lot of ways, is probably just the basis of what it is I tried to do each day, was that I’m sitting backstage and there’s a guy that nobody recognizes who’s about to give a speech.
Suneel Gupta:
He’s a state senator from Illinois, and Barack Obama gets up and gives that speech, and I got to watch it from backstage. What I saw was just this … I get the chills even just talking about it. There’s almost this tidal wave of energy that just sort of ripped through the stadium, and I became one of, I think, millions of young people that night, I became really fascinated with Obama’s story. Who is this? Who is this guy? He was running for senate at the time. Whereas I started to unpack his story, which is what I love to do now, unpack people’s stories, understand sort of what was the arc of it. You do this way better than I do. I’m learning from you.
Debbie Millman:
Hardly.
Suneel Gupta:
What I found, though, was really surprising, which was that four years prior to that speech, he had run for Congress, and he lost.
Debbie Millman:
He lost.
Suneel Gupta:
He lost by a huge margin, a two-to-one margin. It wasn’t close. But the thing that surprised me even more than that, was the way that he was received during that campaign. People described him as stilted—
Debbie Millman:
Professorial.
Suneel Gupta:
Professorial. Yeah, there was a reporter named Ted McClelland who followed him around during that campaign, shadowed him, who wrote that Barack Obama is so dry that he sucks up all of the air out of the room.
Debbie Millman:
It’s crazy.
Suneel Gupta:
Then, four years later, he is this bastion of hope and energy and inspiration. That to me was just the most inspiring thing, which is not necessarily that, “Wow, I was seeing this person who clearly was a rising star.” What was most inspiring to me was sort of this moment of … I call it reinvention or turnaround or whatever it was. I wanted to kind of focus more on that, what happened during those four years and really, that’s how I spend my time today. I try to go to these sort of moments where we don’t really pay much attention to, because we kind of assume that the people that we admire have always sort of been that way. If you rewind the clock, I try to find these almost dips in their experience where it’s like, “No, things actually were going very poorly, and here’s what they did. Here are the adjustments that they made to get to where they are today.”
Debbie Millman:
That is what is endlessly fascinating for me. You did that over and over. While you were at Mozilla, you initially were hired to work on legal matters but you found yourself drawn to the engineering and design areas of the business. You talk about how you were finally given a chance to lead and launch a new product feature for Firefox, but you don’t really talk about how you did it. How you actually got that chance. You certainly were hanging around and showed that you were interested, but what was the catalyst to making that happen?
Suneel Gupta:
Yeah, I mean, I asked for it. One of the things I think I’m pretty decent at is sort of just … if I look at somebody’s workflow, how are people working, I tend to sort of kind of be the person who says, “Well, what about … could we do that? Maybe that could be a little bit different or could that improve things?” Which is interesting because that’s, what I just described to you, is the job of an optimizer, and I don’t like to optimize, but in this case, what I was doing is I was watching these brilliant engineers and designers work. What I was finding is that they were sort of putting things into spreadsheets, and sort of tracking their work in pretty disjointed ways because they were focusing on doing what they were doing, which was writing code and creating designs. So, it started out as, “Hey, could I actually just organize this a little bit for you?”
Suneel Gupta:
I think whenever you’re not really asking for something—you’re not asking for a title, you’re not asking for a role—but you’re saying, “Hey, do you mind if I just … could I do this, and if you like it, great, and if you don’t, then throw it out?” That’s kind of what I did. I went to the head of that time of Mozilla Labs, a guy named Chris Beard, who ended up eventually becoming the CEO, and asked him, and he’s like, “Sure, knock yourself out.” I mean, there’s no sort of pressure for him at that point in time to give me anything. I think when I started to organize things, I think that what he saw was, A, I was a pretty collaborative person. I think the other thing he saw was just a curiosity. I was very curious about what they were doing, and then the reason that matters is because I can help other people get interested in it as well. In some ways, the job of a product manager is, how do we take all this cool stuff that we’re building on the inside and make it intriguing to people on the outside? That’s why I ended up getting the shot.
Debbie Millman:
It’s so interesting to compare the instinct to wait for something to happen, to wait to be discovered, versus asking for something. I have to say, there’s maybe been three instances that I can think of off the top of my head where I was just offered something. Two of those three things were from the same person, whereas 99.9% of everything I’ve ever been able to do was because I had to ask for it.
Suneel Gupta:
Yeah.
Debbie Millman:
It takes a lot of courage to do that. Although, I wouldn’t have thought of that at the time, I think that I’ve come to that conclusion in reading your book sort of that … taking that risk to ask—
Suneel Gupta:
OK, I have to ask this. Was there one moment in particular where you sort of realized that you didn’t want to ask but you realized you had to?
Debbie Millman:
Not until after. Not until after. Now, I give that advice a lot to my students—you have to ask, you have to ask, as you get older and find that the waiting isn’t really working.
Suneel Gupta:
Yeah.
Debbie Millman:
If you really want something you have to take action. You have to.
Suneel Gupta:
Yeah, yeah. Tell me if this resonates, too. When I talk to people who are sure to kind of … I think waiting, one of the things I also hear is that “I’m not ready. I’m not ready yet.” I’m not ready tend to be sort of the three words. “I’m not ready to step into that role.” “I’m not ready to speak my mind.” “I’m not ready to run with that idea.” “I’m not ready.” I’m often asked with the people that I was studying and interviewing for my book, was there one thing? Was there one common denominator amongst all of these extraordinary people, and I would say that, yeah, the common denominator is that none of them were really ready. I could not find a single situation where it was like, “Yup, that person was completely ready to go do what they did.”
Three friends from design school were not ready to start Airbnb, a mid-level talent manager wasn’t ready to start Soulcycle, a 15-year-old from Stockholm, Sweden, wasn’t ready to build an environmental movement, but today, Greta Thunberg is Time magazine’s youngest ever Person of the Year. There were setbacks and there were failures along the way, of course, but I think the mantra that either consciously or unconsciously, most of the people that I study seem to adopt, is that the opposite of success is not failure, it’s boredom.
Debbie Millman:
I also say that the opposite of love isn’t hate, it’s indifference. I think it’s sort of the same thing. The opposite of success isn’t failure. It’s boredom and mediocrity, I think, when you’re just too afraid to take that risk. But one thing about sort of that notion of being ready, that I think is so important to also acknowledge, is that, that sense of readiness usually comes when you feel like you’re not going to have fear about it anymore. That’s never going to happen.
Suneel Gupta:
Never.
Debbie Millman:
Because anything uncertain really does kick up that reptilian part of the brain, and you can’t ever, ever get rid of that. Uncertainty is just the place where that fear lives, and you just can’t ever get rid of that, in the same way you couldn’t ever expect that if you were confronted by something terrorizing, you would feel the adrenaline rush that just happens instinctually.
Suneel Gupta:
Yeah, yeah. In some ways, it reminds me a lot of what you’ve talked about in the past, which is this idea of competence versus courage. I mean, you can wait to build confidence, and what I’ve kind of realized, at least for myself, is that that doesn’t really happen, especially when it comes to new things. I think you said, the idea of confidence comes from repeating something over and over again.
Debbie Millman:
Yeah, the successful repetition of any endeavor.
Suneel Gupta:
That’s how you build confidence, but you can’t necessarily have confidence in that case for anything that’s brand new to you. So, waiting to have confidence, to go tackle something that’s different, that moment may never come, which comes back to sort of like, you can wait to be discovered and that moment will never come.
Debbie Millman:
Yeah, if not now, when?
Suneel Gupta:
If not now, what not now, when?
Debbie Millman:
If not now, when? So you said that after years of working inside other startups, whether it be Groupon or Mozilla, you realize that what you really wanted you had been afraid to do, so what was that?
Suneel Gupta:
I wanted to start my own company. I wanted to put myself out there, and I was afraid to do that. I think that especially when you’re part of another organization that’s doing pretty well, you can get a lot of credit that sometimes maybe you don’t deserve. When Groupon was doing well, at that time, I was the first head of product development that was hired there. There were all these articles being written and I was getting thrown in, as like, “Hey, this guy must be a star,” and I remember thinking to myself like, not really. I think I’m pretty capable. I’m learning as I go but I’m certainly getting a lot more credit than I deserve because I feel like I’m part of this rocket ship right now. If I put myself out there, with my own thing, then it’s just me. It’s just me. I don’t have anything to ride off of, and that really scared me.
Debbie Millman:
At that point, you had what you believed was a winning idea for your own business. Can you share what it was?
Suneel Gupta:
Yeah. So the idea was … at that time, Airbnb was starting to hit its stride, Uber was starting to hit its stride, and I thought to myself, why isn’t more of this happening in the field of healthcare? What can we do with the many, many, I think talented healthcare professionals who are out there right now that might be sort of wanting to do more, have more impact? That was kind of the problem space I was thinking about, but more than that, it was really just going back to a story that I continue to think about, about my father, who, when he was in his 40s, had a triple bypass surgery. It was emergency. By the time I got to school that day, my aunt picked me up, took me to the hospital. I remember seeing him and he looked like he aged 20 years overnight.
I remember when we were on our way back to our house, a few days later, they’ve given us some paperwork. Part of the paperwork was how to eat at home, and listed on that sheet was sort of the dos and don’ts. It had things like “eat broccoli,” “eat Brussels sprouts.” I remember thinking to myself, like, we don’t eat broccoli. We don’t eat Brussels sprouts. We eat Indian food. I remember thinking to myself, This isn’t going to really work for my dad, and it didn’t. He had a very difficult time, as many of us do, trying to adopt a different lifestyle, trying to change our own behavior. It was lucky for us, finally, at the hospital, I was like, “Look, we have to find a program that’s going to work for you.” Insurance ended up kicking in and we ended up getting the help of a nutritionist, who really helped customize our lifestyle into something that was going to work.
We could still be Indian. We could eat Indian food, but we could do it in a healthy way. I believe that that nutritionist is a big part of the reason that my dad is alive today. So the idea for my startup RISE was we could match you one on one with a personal nutritionist over your mobile phone, give you the same quality of care, but we could do it at a fraction of the cost because we could just be … we could be a lot more efficient, using mobile. So, that was the idea.
Debbie Millman:
So as much as it was and is a great idea, you were struggling to get other people excited about it. You started to feel at the time the same frustration that you had back when you were sitting in that cubicle in Detroit. In the meantime, you were contacted by the organizer of an event called The Failure Conference, or Fail Con, where you’ve been repeatedly nominated to speak, and you agreed to be the keynote. But moments before your speech, you began to question your life choices. Not a great time to have that epiphany. How did that impact your talk? Because that really, if you look at the arc of your life, it was one of those defining moments.
Suneel Gupta:
Yeah. I mean, it’s a humbling experience when someone calls you and says, “Hey, we’re doing this conference on failure, and we would love for you to be the keynote speaker.” I thought to myself, I’ve been trying to craft, as some of us do, this image of success, and things don’t seem to really be falling into place for me right now. And I’m about to go talk about that pretty openly. I think that today it’s a little bit different, because failure, I think, is talked about a little bit more now than it was before. This is 2012 when I gave that speech. I felt like, All right, well, now I’m going to end up being sort of the failure guy, which totally ended up being the case.
Debbie Millman:
There was a reporter in the audience for that speech. She ended up writing a huge story on failure in The New York Times, prominently featuring you. It went viral and you ultimately had to change your identity from that “fake it until you make it” attitude of success to being honest about what you did and didn’t know. How did that article change your life?
Suneel Gupta:
Yeah. There was a time where you could literally Google “failure,” and my face would have been one of your top search results. A friend of mine that I spoke to around the time kind of reminded me of a lesson that we’ve learned when we were kids. We used to go to temple together, and the priest that we would see would often talk about … he talked about Hinduism, but he talked about Buddhism as well. I remember there was a parable that he shared with us from the Buddha, and it was that when you feel pain of any kind, two arrows are shot. The first arrow is the arrow that punctures your skin, and there’s nothing you can really do about that arrow. You’re going to feel the pain. The second arrow is the arrow where you really ascribe meaning to that pain.
It’s where you decide that you want to do something with it. That arrow is very much up to us. That’s our choice. He motivated me in some ways of like, what could I actually do with this. One of the things I decided to do was I started to email people I admired but had never had a chance to talk to. I would email them and I would actually include the link to the article and I would say, “As you can see, I have no idea what I’m doing right now, but would you be willing to grab coffee with me or jump on the phone with me?” The response rate to that email was extraordinarily high. I think more important than that, was that because it wasn’t an email that was sort of, I think, espoused in success—it wasn’t somebody who was trying to impress, it just opened the gateway to just really honest conversations.
I was surprised that people were, I think, as willing and actually wanted to share their own failure story, because people don’t really ask that. I think that we … again, we craft these images that almost hide that stuff, but there’s some really, really interesting stories there, and I was starting to hear those stories. That ultimately ended up becoming the foundation for, I think, how I spent the next several years.
Debbie Millman:
Yeah, I mean, they weren’t mercy meetings; people weren’t meeting you because they felt sorry for you. They were really interested, and that provided an epiphany that changed the way you see everything. People who change the world aren’t just brilliant, they’re backable, and ultimately gave you the runway to write this remarkable book. Talk about what being backable actually means.
Suneel Gupta:
Yeah, yeah, I was finding that there are certain people who have this almost mysterious it quality. It seems to be this ability to walk into a room and really just inspire people to take action. The trick of it is, I think the most important thing is, it’s when it’s not necessarily obvious. When you can walk in with the obvious sort of like, “this absolutely we need to do, I have all of the data, I have all of the proof”—that’s not necessarily a backable moment. A backable moment is when we don’t know. We actually have to take a bit of a leap of faith here on you. We have to take a leap of faith on your idea. We still feel inspired to do that. It really kind of cuts to this idea that I just didn’t understand at the time, which is that creativity and persuasion are two different things.
You can have a brilliant idea, and you can still be dismissed. At the same time, by the way, it works the other way. You can have ideas that aren’t necessarily all that great, that don’t necessarily do a lot of good. We’ve seen plenty of documentaries on some of these lately. Yet that person is incredibly backable. They have that it quality. What I thought to myself as I was starting to kind of watch more … what was happening with Theranos, what was happening with the Fyre Festival, and later on what was happening with WeWork—I thought to myself, we need more high-integrity people in the world who know how to sell a good idea, and maybe this book can provide a little bit of a framework. One person that I sort of continued to keep in mind, even though it’s an older story, is a guy named Bob Ebeling. Ebeling was an engineer on the Space Shuttle Challenger.
The day before the Challenger went up, he actually was looking at some of the data and he found that, “Look, this is actually a little bit too dangerous.” Overnight, conditions are going to change. The temperature is going to drop and it’s going to put things at risk. So he does what I think most of us would do. He calls a meeting. He gets his colleagues into a room and he presents sort of his findings, and then he presents a recommendation, which was, let’s just delay this thing. And he was dismissed. The Challenger goes up the next morning, disintegrates within 90 seconds, killing everybody on board. Ebeling ended up spending the rest of his life blaming himself for that. He gave an interview with NPR where he said, “God should not have chosen me for that role, because I had the information, but I didn’t have the persuasive ability to get everybody bought into what I had to say. God should have chosen someone else.”
So I think that we may not have the drama of a Bob Ebeling, but I think we can all, I think, relate to that, where it’s like, we feel inside that we have something to offer, but the people that we’re sharing it with are not nearly as excited about it as we are. There’s something missing there, and that’s where this book really aims to come in.
Debbie Millman:
You used to consider people who were backable to be that way naturally—it was a talent you either had or you didn’t. Now you know it can be learned. How did you realize that?
Suneel Gupta:
I think it’s by rewinding the clock and realizing that the people that they are today aren’t the people they were in the past. They had gone through these failures. They had gone through these rejections, and what inspired me to write the book … because if I found that these people were all naturals, there would be nothing to write here, right? Just either have it or you don’t. But what I found is that there was a series of adjustments that they made. What really got me excited is that these adjustments actually weren’t that big. The way that I put that to practice, to test, was I was actually out there pitching my own idea, and I was getting rejected by every investor that I was pitching. So as I was learning these techniques, I was just putting them … I was bringing them right into the pitch room and realizing that, “Hey, I’m getting a little bit of a different response now.”
Debbie Millman:
So it essentially revealed to you at the time that your idea for RISE, your business idea, wasn’t a bad idea. You were just sharing it in a way that wasn’t really getting backers excited. So how did you change your pitch to essentially raising the money that you needed, to launching RISE and serving over a thousand patients, Apple naming it the best new app of the year, and then First Lady Michelle Obama asking you to be on her technology team and becoming her official technology partner in the Obama White House? So just share with me a little bit how you adjusted your own pitch for that monumental success.
Suneel Gupta:
Yeah, yeah. One of the things that I think was really important was the way that I talked about my dad’s story, the story that I shared with you before. My thought was that going to pitch sort of analytical, Silicon Valley sort of folks, it’s all going to be about the numbers. It’s all going to be about the data. It was very much focused on the increasing rates of diabetes and hypertension, and obesity, and how large a market we were really going after, right?
Debbie Millman:
Right.
Suneel Gupta:
I remember, one of the people that I ended up speaking to was Tim Ferriss.
Debbie Millman:
Yes.
Suneel Gupta:
What I did is, again, I spent all this time talking about the market size, and at the very end, I told a story about my dad. Then Tim says to me, “why did you save that story to the very end? Why did you make it a footnote? You should tell that story up front and then you can zoom out and you can talk about the numbers. You can talk about the millions of people who are out there, who are going through their own version of your father’s story.” I mean, he shared with me that when he did that for his book, by the way, with The 4-Hour Workweek, how when he changed from having to write for a mass market to changing to writing for just one friend, how it made his writing sharper, how before he had been turned down by over 25 publishers but now when he was writing for one friend, publishers ate it up.
The point he was trying to make and what we talk about in the book is the power of, I think, casting a central character for your idea. One person that you are trying to serve, and making sure that you never forget about that one person. You’re bringing them to the forefront of your pitch. We talk a lot about storytelling in business; I think it’s kind of become sort of an in-vogue term. But storytelling is not getting up and saying, “once upon a time, so and so happened,” and sort of leaving. You have to marry it with substance as well, right? In this case, it’s the story that brings you in, but it’s the substance that really keeps you there. Again, when I just made that shift, when I started telling my dad’s story first, what … I could just see that inside the room, people were engaged in a way that they weren’t before.
Now they wanted to learn more, and I found by the way that was a reoccurring theme. Kirsten Green, who runs a venture capital firm named Forerunner Ventures, she was one of the first investors in the Dollar Shave Club, and I asked her, like, “Why did you invest in that business?” She said, “Well, the reality is that when I got that pitch deck, I had zero interest in investing, zero. In fact, I said no.” But when she met Michael Dubin just happenstance at a party, the founder of the club, he walked up to her to share more about the idea. She told me, she was like, “Oh, god, I’m going to hear the same thing that was in the deck.” He didn’t even bring up any of the numbers. Instead, he walked her through the customer experience. He said, “Today, you have these 20-something males who care a lot more about their health than their father ever did. That means what they put in their body, also what they put on their body; they’re very used to convenience. They’re used to buying things online, but when it comes to razor blades, that all kind of goes out the door. They walk into a pharmacy. They’ve got to sort of locate where the razor blades are; oftentimes it’s behind literally a security case, so you have to push a button and you have to wait for somebody to come find you in the aisle. By the way, now everybody is sort of staring at you, and behind that lock case are things like condoms and laxatives, and no one knows what you’re leaning there to buy.” She’s like, the whole thing just … it doesn’t make sense. For Kirsten, who by the way is like a former Wall Street analyst, who loves the numbers, was like, that’s the thing. It was that story that sort of pulled her in. It got her engaged. So I know it sounds simple, but oftentimes we save the stories to the very end or sometimes we don’t tell them at all. Just making that simple shift of telling the story first, and then talking about the market, made a huge difference.
Debbie Millman:
Yeah, it reminds me … my dad also had triple bypass; he’s since passed away but after his surgery, we also had to dramatically change his diet, dramatically. He was so unhappy with it and we ended up finding slews of sweets in the glove compartment of his car, because he was hiding it and still eating it. But it would have been really helpful to have something like that when he was alive.
Suneel Gupta:
It’s so interesting, because my parents would work late. So they come home, and that meant we wouldn’t eat until probably around 8, 8:30 or so. This was a late meal, and we go to bed pretty soon after; it’s by 10:00, so it wasn’t a lot of time in between. This is one simple thing that we ended up doing, was we started making these low-fat lassis. Have you ever had lassi at a restaurant, an Indian restaurant? It’s basically yogurt and water, and you can mix in some other things, but ours was like a low-fat sort of low-sugar version. It’s like yogurt and water with some spices in. We would always have that in the fridge. So when they came home from work, the first thing that he would do is he’d have a glass of that. He was eating much less.
Debbie Millman:
Yeah, it changes everything.
Suneel Gupta:
Which is that simple thing.
Debbie Millman:
You took RISE to the next level. In 2016, One Medical, a thriving healthcare company, acquired RISE from multiple times its original value. I have to say I’m a member of One Medical. So I really love that app and the brand. You’ve since gone on to become an entrepreneur and residence at the VC firm Kleiner Perkins; you’re also currently a visiting scholar at Harvard University. What made you decide to write your book? What made you decide to write Backable?
Suneel Gupta:
Yeah, I think it still all comes back to that story in 2004, with Barack Obama, and just realizing it’s just this moment, the way that people are today is in some ways an assumption that we say that they have always been that way, and realizing that that wasn’t the case. It just made me excited about the idea that, like, “Hey, there’s some stories out there that just haven’t been told before.” I find them everywhere. I worked in politics. I spent some time working in Hollywood. I spent time working in tech, and I just had this like endless curiosity for, “OK, you’re successful right now. That’s great, fantastic. Let’s rewind the clock a little bit. What’s the Version 1 of you like, and then let’s talk about how we went from Version 1 to where we are today.”
Debbie Millman:
You declare that everyone is within striking distance of becoming backable, and we just need to make adjustments to our style without sacrificing what makes us who we are. The book details several adjustments or steps, and we talked a little bit … we hinted at that they course-corrected both your life and career, and I really do think that they can help a lot of people do the same with theirs. But Step 1 is to convince yourself first, and you go on to state that what moves people isn’t charisma, it’s conviction. So I’m wondering if you can elaborate on that a little bit.
Suneel Gupta:
Yeah, definitely. One of the assumptions that I made when I started doing this research was that Backable people were going to have a certain style of communication. They were going to, for the most part, speak with compelling hand gestures and they create eye contact and just sort of have more of a, almost a Toastmasters-esque or Dale Carnegie-esque way about them.
Debbie Millman:
Yes.
Suneel Gupta:
I found that very quickly to not be the case. In fact, I would say that now the vast majority of the people that I studied for the book don’t talk that way, and they don’t have sort of classic communication styles. One quick example of that is if you go look up the No. 1 most popular TED talk of all time, and one of my favorite speakers, the late Sir Ken Robinson, who gives his brilliant talk on education. When you watch it, he has one hand in his pocket, he meanders on and off script, but it’s a brilliant talk. I found that to be more the case, which is that backable people take the time to convince themselves first, and then they let that conviction shine through with whatever speaking style it is that feels most natural to them.
Debbie Millman:
Step 2 is to cast a central character, and I think we’ve been talking about that, with you casting your dad or me casting my dad, but talk about what it means for others.
Suneel Gupta:
With anything that we’re doing, I think having the ability to be representing someone who’s other than you, it’s so important. I ended up talking to a lot to agents, people who represented other people—sports agents, talent agents—when I was writing this book. One of the things I noticed is that when they were in the room, representing their client, they were a lot more confident than when they were in the room representing themselves.
Debbie Millman:
Absolutely. I totally understand that. Yeah.
Suneel Gupta:
Right, and I think that even though we’re not all necessarily agents by profession, we can all, I think, put ourselves in that mindset, which is that no matter what it is we’re doing, no matter what type of work it is, there’s always somebody else that we are there for. Sometimes we can forget that. When I was at Groupon, early days, our central character was the small mom and pop shop, and there was this small business owner. I still remember, when I went to go interview for that role and when I spoke to Andrew Mason, who is the founder, CEO of the company, he took me on a walk around downtown Chicago. He pointed to these different shops. He knew each of these shop owners by name. He told me their stories. “Jim is a baker. He grew up baking with his mom and he had that craftsman early age.” Right?
He was just telling me his really compelling stories. That was a central character and I remember thinking to myself, I have to work at this company. Right? I have to. And when we’re in the office, that’s all we talked about. When we looked at the walls, it was the stories of these small business owners, and it wasn’t done in like a cheesy way. We really did believe that. As we started to grow as a company, especially as we started to think about going public, the focus shifted from that central character to quarterly earnings. What are the things going to look like to shareholders now? And because we lost that focus, I think that our business really, really suffered. We lost 80% of our market value within months, and some of our best talent ended up leaving.
If you compare that to I think some of the other organizations we see out there that really keep like in touch with their central character … I’ve been going to the Airbnb office to spend time ever since they were in their first-ever spot in Potrero Hill. I remember they had a storyboard up on the wall of what their guests go through, and what their host go through. It was literally a frame by frame of the experience, so that designers and engineers and business people could go to that storyboard together and say, “Hey, this is the part of the experience that we’re sort of thinking about,” or “here’s the part where we think could be reinvented a little bit.” It was just his brilliant, beautiful way of making sure that every time you walk into the office, you knew who you were there for.
Every time you walk into a meeting, you knew who you were there, representing. So whomever it is, right, it could be just bringing to mind a very clear image of that person who is other than you, that you were there to serve. I think just can do wonders for your … the way you can convince others to get behind an idea.
Debbie Millman:
Step 3 is to find an earned secret. What does that mean?
Suneel Gupta:
One of the people that I studied for the book was Brian Grazer. He’s this prolific filmmaker, he’s won over 130 Emmys and dozens of Oscars. He also invests in technology companies, and he runs large teams. So when I was in his waiting room, there were people there ready to pitch him on everything, apply for jobs, film ideas, technology companies. I said to him, “Brian, there’s a lot of nervous people out in that waiting room right now, and if I could have given them one piece of advice on how to be prepared for this meeting, what would it be?” He thinks for a moment. He says, “Give me something that I can’t easily find on Google.” I thought that was so interesting, because great interviews, great pitches, great presentations, they tend to be based on an insight.
They tend to be based on something that you have gone out into the world and you have found through firsthand experience. By the way, it doesn’t necessarily need to be a revolutionary finding. One of the key things about having an earned secret is that you earned it. You put yourself out into the field. You did it yourself. Shortly after my book launch, somebody contacted me. She’s a mom and she’s returning to the workforce, and she was applying for a job at a social media company. The thing is, that it was very much not a product that she used. Her kids used the product, but she didn’t. So she was trying to prepare for the interview and she was like, “How do I do this?” What she did was really clever, I think.
She decided to interview every single one of her daughter’s friends. What do you like about the experience? What do you not like about the experience? Then she had them send her screenshots, these little moments that they loved or wish were different. She takes her phone with her to this interview, which is over Zoom, it’s during the pandemic. Now, instead of just having her background, her bio, she shows this hiring manager this gallery of moments, these screenshots that she’s collected through her research. This hiring manager is so impressed that not only does she get the job, but right in the middle of the meeting, he ends up patching in one of their UX designers so that they could see some of this stuff, right? I asked her, like, “How much time did it take you to really prepare for this?”
Her answer with me was less than two hours, less than two hours to do all of that. All the interviews, packaging it all together. It just wasn’t all that much, but the point is that she sort of, in some ways, followed a very simple framework that I think backable people follow, which is like, what would most people do in this situation? What’s the kind of research most people would do? Then, how do I put myself one step further into the story?
Debbie Millman:
One of my favorite anecdotes in your book is when you talk about how when you were working on RISE, you stood outside Weight Watchers meetings and as people arrived, you ask them if you could show them a quick demo. That’s how you found your first customers.
Suneel Gupta:
Yeah.
Debbie Millman:
I just think that’s brilliant. I want to jump to Step 5, which is to flip outsiders to insiders. In telling us what that means, I was wondering if you could share my second favorite anecdote in the book, which is the instant cake mix anecdote, please.
Suneel Gupta:
Of course, of course. Yeah. In the 1940s, Betty Crocker came up with this idea for instant cake mix. All you had to do was pour water into a mix, and then pop it in the oven, and voila, you get this really tasty treat. So they were very confident that this was going to be a huge mega bestseller product. So they were very confused when they found out that people were not buying these instant cake mixes. They could not figure out why. So they hire this psychologist, a guy by the name of Ernest Dichter, to go out to the field and start talking to customers. What Dichter comes back to the executives at Betty Crocker with is, “I think you have made the process of making a cake too easy, too simple.”
Debbie Millman:
All they had to do is add water.
Suneel Gupta:
It’s all they had to do.
Debbie Millman:
Right, nothing else.
Suneel Gupta:
It’s all they had to do, they add water and say it was so easy that when the cake actually came out of the oven, they actually didn’t really feel a sense of ownership over that cake; they didn’t really feel like they had made that cake. So Dichter’s recommendation was really simple: Why don’t you remove one ingredient and just see what happens, one key ingredient? So they do, they remove the egg. Now, as a customer, you have to go out, you have to buy fresh eggs, come back, crack it into the mix, mix it in and then you pop it into the oven. Sales just completely skyrocket. They completely take off. So much so that Betty Crocker ends up building their entire advertising and marketing campaign around the idea that you crack in your own egg, right?
You’re still part of the process, and researchers have unpacked I think this idea over and over again; there’s a group out of Harvard that called this “the IKEA effect,” which basically says that we place up to five times the amount of value on something that we help build than something that we simply buy off the shelf. So, if you think about “what does this have anything to do with creativity or building things?” I think we’ve kind of been told that innovation is a two-step formula—you come up with a great idea and then you execute on it really well. There’s a hidden step in between, right? This hidden step is where you bring in early people. You bring in early employees, early colleagues, where they can actually crack their own egg into the mix, where they can actually feel like it’s their creation as well, right?
I think you can trace literally every successful organization, every successful product, every successful political movement, back to this hidden step. We know that. It was never just one person who came up with an idea and ran it all the way down the flagpole. It was always a group of people who felt almost founder-level ownership over the idea, even though they didn’t come up with it themselves.
Debbie Millman:
So you’ve discovered that people tend to fight the hardest for ideas that they feel some sense of ownership for and with.
Suneel Gupta:
Yeah.
Debbie Millman:
So for somebody that is trying to get their own idea off the ground or pitch themselves in a way that is more successful, how do you foster this? How can people sort of find their own egg?
Suneel Gupta:
Yeah, yeah. Well, I think it’s about how do you give the person on the other side of the table, the person that you’re talking to, how do you hand them an egg? How do you actually have them crack their own egg into the mix? One of the ways that we do that is by falling in love with a problem, but not necessarily always falling in love with the solution. One of the mistakes that I used to make going into rooms is that I would walk in with everything figured out, a fully baked plan, right? Then, I would ask people to buy in. This didn’t just happen as an entrepreneur, by the way. This happened when I was working inside companies and I was having to rally people who didn’t think necessarily like me. They were part of different departments. They were in charge of different metrics.
I wanted them to rally around what I had to say, and so I’d walk in with these bulletproof plans, and I would say, “Hey, are you with me?” Oftentimes, the answer was, funnily, no. Actually, we’re not with you. What I found is that instead of walking in with a fully baked plan, walking in with some semblance of what something could be, but not necessarily how it has to be, right? In other words, sharing just enough, you can get across like the problem that you’re trying to solve, but then open it up to the creative possibilities that come up inside the room. Now, I always have to caveat this, because it doesn’t mean that because you’re walking in and sharing 20%, that you’re only 20% prepared. You’re actually 100% prepared. What I have found is that it takes a lot more preparation to have a discussion than to have a presentation.
Debbie Millman:
Yes.
Suneel Gupta:
The second thing I’ll throw in just very quickly, as part of that, is, what are the people who are in the room, what are they excited about? Oftentimes we do research on the people we’re trying to pitch for. We kind of understand their sort of bio but I think that we need to like all take a Debbie Millman sort of approach to research. You are a very thorough researcher; when you interview your guests, it’s very clear. I think we all need to do that with the people we’re walking into a room with. What do we care about? Those are the things that you want to bring into the room. “Hey, I know that one of the things you paid attention to, you love thinking about, is how mobile distribution really works.” That’s actually one of the things I’m trying to figure out right now.
I have some options, but can we talk through that together? Right? If you can get to a point where now you shifted from presentation mode into huddle mode, where the two of you are looking at something together, now, you’re giving that person founder-level passion over your idea.
Debbie Millman:
Suneel, you have backed startups including Impossible Foods, Airbnb and 23andme. What did those founders say to you to feel confident in backing them?
Suneel Gupta:
I think they very, very much had put themselves I think inside the story. Brian Chesky again, for example, not coming in with just, “Hey, wouldn’t this be cool,” but like having come in with like, “I’ve been sleeping on couches, investigating how this whole thing works. I’ve been renting out my own apartment. I put out Craigslist ads. Here’s how many people actually applied for the vacancy that I had.” Leah Busque, when she was founding TaskRabbit, she was actually cleaning homes herself. When Logan Green was creating Lyft at that time, Zimride, he was the one actually carting passengers around Los Angeles himself. He was doing that and it was just curiosity that was taking people into the story and then, they were getting these insights along the way.
That impresses me, just going way beyond Google, and I respect it so much, especially for people who are smart, who could just stay behind the desk and come up with a really great pitch deck, but they decided not to do that. They took much more of a person on the street kind of approach, and that’s what I tend to look for.
Debbie Millman:
Suneel, I have one last question for you. I want to ask you about a little morning routine that you have with your two daughters. You ask them two questions, and I’m wondering if you can share both what the questions are and their responses. I think it’s a really wonderful insight into who you are deep down.
Suneel Gupta:
So I started doing this during the pandemic. My daughters are doing homeschool, and every morning I was getting them sort of set up. I would ask them two questions. I’d say, “Hey, what is the meaning of life?” They’d say, “To find your gift.” I’d say, “Well, what is the purpose of life?” They say, “To give it away.” It’s my favorite quote by Picasso. The meaning of life is to find your gift, and the purpose of life is to give it away. I continue, Debbie, to come back to not just how we get there, but the three words that tend to hold us back from sharing our gift with the world—which is, “I’m not ready,” right? “I’m not ready to do that.” If I have one role, as a dad, it’s to somehow tap into my mom’s energy, let it sort of generationally flow through me in some way so that they can feel that they are ready.
Debbie Millman:
I think that it is one of the most heartwarming things that I learned about you, and such an inspiring way to think about the world. Suneel Gupta, thank you so much for such an engaging conversation, and such a generous conversation, and thank you for joining me today on Design Matters.
Suneel Gupta:
It’s such a pleasure. Thank you so much Debbie.
Debbie Millman:
Suneel Gupta’s new book is titled Backable, The Surprising Truth Behind What Makes People Take a Chance on You. You can read more about everything that Suneel does at Backable.com. This is the 17th year we’ve been podcasting Design Matters, and I’d like to thank you for listening. Remember, we can talk about making a difference, we can make a difference, or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.