Daniella Pierson: Why Failure is the Measure of Success

Full Transcript

Note: Transcripts are generated by machine and lightly edited by humans. They may contain errors.

Daniella Pierson: I’m kind of the recipe for the person who should never be an entrepreneur, but I still am. Just because you have all of these barriers that’s history and statistics say will not work for success, you can actually make a new recipe. And that’s why I built Be a Breadwinner and why I’m so excited for the launch is because it really is for somebody who wants to have success on their own terms and be a barrier breaker, a bread taker of a new mold and a moneymaker.

Zack Doherty: That was Daniella Pierson, CEO of The Newsette. Daniella visited Stanford Graduate School of Business as part of View From The Top, a speaker series where students like me sit down and interview leaders from around the world. I’m Zack Doherty, an MBA student of the Class of 2024. In our conversation, we discuss pursuing creative, entrepreneurial paths, overcoming mental health barriers and empowering others through financial freedom.

Daniella, welcome to Stanford.

Daniella Pierson: Thank you so much for having me. It’s weird. I feel like when I was 18, if I would have even stepped foot here, I would just like burn into ash because I was the dumb twin. But my sister would have thrived. She would have turned into these flowers.

Zack Doherty: I’m sure you would have done great, and it is such a pleasure to have you here. I have to admit, I’ve been following you on Instagram, and you are partnering with some really heavy hitters — Selena Gomez, Serena Williams.

Daniella Pierson: Yeah.

Zack Doherty: DVF, who has actually sat in this very same seat as a View From The Top speaker.

Daniella Pierson: I’m going to send you a picture like right after this, and she’s going to be like, “Ha-ha.”

Zack Doherty: But there’s actually one star in particular on your posts who I would love to get on next year’s slate.

Daniella Pierson: Okay.

Zack Doherty: Your Chief Happiness Officer, Leo.

Daniella Pierson: He would love it, but he would just honestly curl up and nap the whole time. But I think people pay for that.

Zack Doherty: Well, I’m sure we’ll all have to find some good questions to keep him engaged. But in all seriousness, I can’t wait to get into your entrepreneurial journey, from founding your first company at just 19 years old to recently announcing your third venture in collaboration with J.P. Morgan.

Daniella Pierson: Yes.

Zack Doherty: But your early experiences that got you to this point are equally as inspiring, so I want to start back there.

Daniella Pierson: Okay.

Zack Doherty: You’ve spoken previously about growing up in Florida in a family of hard workers, between your mother, your father and your identical twin sister. How did those early childhood experiences shape your understanding of success?

Daniella Pierson: Wow. Well, first of all, thank you so much for having me. I have horrible eyesight. I was just talking to Nora who’s right there with the camera on me saying that it was just so odd that my story has gotten me here, because, again, I just did a Ted Talk at U Penn, and that’s where my sister went.

Here’s Stanford and a lot of my super-smart friends went there and super successful friends went here or are still here like Phoebe Gates, etcetera. And I just always felt so, what’s the word, jealous that they got to be among so many other people that excelled in that amazing lane. But it was very different than the lane that I was supposed to be on.

So I think in order to answer your question, the first thing I need to say is success looks different, and now I know that, and now that’s really the message of Be a Breadwinner. It looks different for everyone.

So, I grew up in Jacksonville, Florida, the sexiest part of Florida. No one ever knows it, but it is. I grew up as the “dumb” twin. My father, who is from Niagara Falls, New York, he didn’t go to college. His dad worked in a factory and died very young, unfortunately. And he had four siblings, and he started working at 13 and worked his way washing cars, fixing cars, etcetera.

My mother grew up in Columbia in Bogota. We both have Hispanic upbringings. And she actually grew up even poorer. She lived next to a mass grave, that’s how poor. But they were the lucky ones. They had shoes and an actual roof instead of like a hut. But she worked her ass off, and she was like all of you guys and like my sister. She really excelled at school. And she almost didn’t really have a choice; she had to, because there were private schools in Columbia and then very, very bad public schools. And the only way she could ever go to a private school was to win the one scholarship that they had every single year and had to be the best student. So she literally won it every single year. She didn’t have a choice. It wasn’t like, “Oops, if I get a B” — it’s like survival mode.

And her family just wanted her to become an oral surgeon, a dentist, because my grandfather, he still does this, I don’t know why because he doesn’t have to anymore, but he still makes dentures. I don’t even know what it would be called here. But the whole dream was that she was going to be an oral surgeon, he was going to do the dentures, and it was going to be great and like the epitome of success.

So, both of my parents know what it’s like to go from absolutely nothing to success, but in totally different paths. And I mirror my father a lot, and my sister mirrors my mother a lot. And my dad was always much harder on me because I think he thought that I was kind of like his son, as like a tomboy. He was such a playboy, and he says that God’s curse to him for being a playboy was that he got two twin girls and never got a son. So I was like the one that would fish with him, etcetera.

But it’s a very long way of me saying that the way that I developed my version of success was through school because that’s all I knew. I was very lucky to go to a very good school in Jacksonville, Florida. Again, my parents worked their asses off to make sure that we would never have to suffer like they did.

And Alex was just always amazing at school; that’s my twin. Her name is Alex Aster. She’s a New York Times best-selling author, so cool. But she was always excelling, and I just hated it. I honestly thought I was dumb, and it’s because my teachers told me I was dumb. I didn’t have a lot of teachers that were like, “No, you might be so good at this other thing.” It was like, “If you’re not good at math and science and history and all these things,” — sorry professors in the room, but if you’re good at all of those subjects, I don’t want to hire you on my team. I want you to be amazing at one thing. But it made me feel so stupid because I just couldn’t learn it.

And I realized as I got older that I couldn’t learn it because I didn’t care. I knew I was never going to professionally measure triangles, so why? I still wonder. Please, someone in the audience, please let me know in the Q&A. Or the earth’s crust, how many times did I learn about that? Amoebas, oh my goodness. Jesus. It’s like they’re preparing us to be Renaissance people of the world.

And I just could not get myself to care until sophomore year when I saw my sister getting letters from places like this and U-Penn, etcetera, begging her to apply, and I obviously got letters telling me not even to try because I was a B and C student; my sister graduated from U-Penn Summa Cum Laude, etcetera.

So then I was like, okay, if I don’t get my shit together, I’m going to be stuck in Jacksonville, Florida my entire life, and that’s not happening to me. So those triangles became very interesting, and I almost used it as a path. Instead of caring so much about what I was learning about, and I had professors who almost liked to bring people down; it was just very odd and liked to make the comparison of the dumb twin and the smart twin. That was literally my nickname from professors. It was really cruel. Hopefully times have changed.

But I started basically using something that would become a barrier to me that I didn’t know I had, which was OCD. I was undiagnosed. I found out I had it my freshman year of high school because I took a behavioral science class, and we talked about Schizophrenia, OCD, and I was like, “Oh my god. That’s the stuff I do.” And even though my parents were in a position to get me a therapist, a psychiatrist and it would have changed my life, my mother had the shame of Latinas — “Oh no, if something hurts, you don’t say anything. It’s just emotional. Whatever.” My dad is a very man’s man, like, “Oh, we don’t talk about that stuff. Whatever.” So I basically got no help from anybody. My parents feel very bad now about it, but times have changed.

So I used that OCD to my benefit. I didn’t know it at the time, but when you have OCD and ADHD, which I later found out I had, if you love something, you can do it for eight hours straight without even getting up to pee, like truly. So, that’s what I did. I saw getting out of Jacksonville, Florida here and then put all this work here, and I ended up going from almost all C’s and B’s to straight A-pluses. And I think my parents were like, “Wait, what happened?” And I ended up getting into B.U.

But that was my first introduction to what does success look like, and it truly felt like if you were not perfect at the things that the professors are telling you you have to be perfect at, at such a young age, middle school, high school, when you’re developing as a person, it felt like you were an outcast, where I see so many successful people, like my friend, Rupi Kaur, who’s the best-selling poet in the world. Actually, her, Milk and Honey book outsold Odyssey, which is crazy. And she’s a multi-millionaire, and she’s a very similar way.

So, I think both ways, like what you guys have done to be in this room is so admirable, and I wish I had tried harder in high school before so maybe I could have been among you all, but I’m still proud of my success story.

Zack Doherty: It’s incredibly inspiring, and I think it’s amazing how you were able to channel that focus into your success in high school, which, as you mentioned, led you to be you. While you were in college, that’s also the time when you founded your first company, “The Newsette.”

Daniella Pierson: Yeah.

Zack Doherty: What was your motivation for starting a company at that point rather than trying to have a more traditional college experience?

Daniella Pierson: Yeah, so basically, it’s funny how so many different categories are woven through your entire life. I’m 28. I’m too young to say this. I used to feel so young, and now I feel so old in so many rooms. I’m too young to say this, but I’ve really lived in the last nine years, better or worse. And so many themes come back to almost haunt you, but sometimes in a good way. Like the thing you thought was the worst thing in the world, you’re like, “Thank God that happened.”

And so, when I was in school, I was so excited when I got into B.U. I was thrilled because of the first two years of high school, my GPA average wasn’t as good as it would have been if I would have cared the entire time. So, B.U. has this special program called The College of General Studies.

And so I was like, “Okay, great.” Basically, I think it’s like the bottom 10 percent are people who get accepted. They go into this school, and you kind of have to prove yourself to go into the College of Arts and Sciences, whatever the F that means, you know, the business school, the com school, etcetera.

So, I wasn’t off the hook yet. I had to prove that I could get into the business school. So, I was still, “But I’m going to learn. I’m going to finally learn things I want to do, and I’m going to be a professional,” because I always just wanted to go out and work. And the first day I go to College of General Studies, I sit down, and guess what the first subject is?

Zack Doherty: Triangles.

Daniella Pierson: Triangles. And I was like, “What the actual fuck?” And I realized for two years I was going to be doing the same thing, learning about history, amoebas, all of those things again. You’d think I’d be an expert, but oh my God; I don’t even know any of that stuff. But, like, I just literally was like, “No.”

And so the first year, I was so depressed and I honestly thought like, I got into B.U., but lightning doesn’t strike twice. I’m not going to get into the business school.” I just counted myself out because I felt stupid in those classes. I didn’t care. I wanted to use that time to do something.

So, very quickly in my sophomore year, I stopped feeling sorry for myself, and I realized that I actually had an opportunity, that I was there, and I was lucky enough because my parents, again, worked their asses off to allow my sister and I to go to college without having any debt or having to have a job. That was the best gift that they could have ever given me. They gave me the gift of time.

So while they were like, “Go find yourself and make friends,” that wasn’t happening; I wasn’t invited to any parties; I decided to use that time and say, “Okay, if I’m not going to really care, I’m just going to kind of not fail out, which would be hard, and I’ll tell you about that in a second, harder than I thought, let me use these next three years where this is the only time in my life I’m not going to have any responsibilities. I have a bed to sleep in at a dorm. I just have a few classes a day. Let me use this time if no one’s going to hire me to hire myself after college.”

And I just got it into my mind. I don’t know where this confidence came from because I had zero confidence. I literally would wake up sometimes in the morning and think, “What am I even doing? I’m just a waste of space.”

Truly, at 19 or 18, I didn’t feel like I had a purpose in this world. I oftentimes would tell my mom, to her horror, that I thought I would die young because there had to be some inkling of like, “I want to be a news reporter. I want to be a scientist” — not a fucking scientist.

Zack Doherty: [Laughs]

Daniella Pierson: Sorry. But like, you know, “I want to do something.” But I just could not picture myself doing anything. So, I was like, “Oh, I guess I’m just psychic, and there’s no future, and that’s it.” And my mom was also struggling because she dedicated her entire life to me and my sister, my twin, so she left at the same time. And then she just had my dad.

And she really had no life because she gave up being an oral surgeon because when she came here, she had to take another course to be certified here, and she immediately got pregnant with twin girls, and she wanted to be a mother. So she was kind of like losing herself and her independence, and she would call me with her problems, and all of a sudden I felt like I was the parent.

And I told my mom, “Don’t worry. I’m going to make it so that me, my sister, her, anyone, could make our own decisions because we’re going to have financial freedom because I’m going to build a company, and I’m going to make us all filthy rich.” And she’d be like, “Okay, honey. Whatever. Maybe Alex, but not you.” But she was like, “Oh, no, don’t worry about me.” But honestly, the worry and the fact that so many women in the world are beholden to spouses who make a certain amount of money, etcetera, and the wife doesn’t work or maybe she doesn’t make as much or a partner, you know, woman and woman, man and man. There’s such a power imbalance there.

And my mom, even though she had worked so hard, just like my dad, didn’t really have any money of her own. And even though they didn’t sign a prenup or anything, she would have gotten half, not that they were going to get divorced, but she just kind of felt like, “Wait, what is my purpose now?” And I wanted to give her that purpose and that freedom.

So that’s the stuff I really don’t talk about. I talk about, “Oh, I was dumb, so I wanted to hire myself. Ha-ha.” And then that’s like the headline. It’s also that I wanted to save my mom from ever having to make a decision based on just staying with somebody because they would pay for me and my sister’s college or whatever. My parents are still together today. I’m painting it like my dad’s horrible. No, they’re still together today, but she could have traveled the world. Like, go play tennis with your friends. I don’t know.

But she just didn’t feel like she had that freedom because she didn’t feel like she had anything of her own. And I was able at 25 to make my mother a multi-millionaire because I gave her 15 percent of my company. And that was the greatest gift I could have ever given my entire family because now they are free to do what they want, and that’s the greatest gift I got as well. Because I really thought it was going to be when I saw millions of dollars in my bank account, I really thought it was going to be like an F-U moment. Like, “I’m going to go to my high school reunion” and whatever. And I didn’t care.

It was like, you work so hard, and you finally make it, and you’re in this big apartment that used to be owned by the Chairman of NBC, and you feel like you married a rich guy, and you’re just like, “Yeah, I guess I live here.” And it’s so weird. I kind of pinch myself every day because I was the dumb twin. That was my identity for my entire life. Only the last four years I was, “Oh, she’s not a dumb twin; she’s a9 smart twin.”

And my sister is wildly successful as well now. But no one thought I would be anything, like literally anything. And so the fact that I’m in this room, and it’s not like, “This is why you don’t do drugs” or something like that — [laughs] I’ve actually never done drugs. That’s why I had no friends in college. But it’s just astounding because I know how hard my sister worked to get into Penn and how hard all of you work to work so hard here and then afterwards. And it really is just like the harder you work, the luckier you get.

And I found an opportunity for me to work really hard on something that, thank God, became something. But it wasn’t luck. I worked every single second of the day. I was obsessed with it. And it was because I wanted independence for myself and my family, and I also kind of needed a job when I got out of college. I didn’t want to go back to Jacksonville. [Laughs]

Zack Doherty: I think that’s a amazing motivation. And obviously you proved a lot of people wrong. “The Newsette” has grown into a phenomenal success. It’s become a next-gen media company and creative agency that now works with over one million customers daily.

As you were seeing the early signs of success and the company was scaling, how did you initially think about differentiation and product market fit considering how competitive and crowded the media space is?

Daniella Pierson: Yeah. So, I wish we had a million customers. That would be cool. No, we have a million readers or reach, and they are customers. The weird thing about media, and honestly, none of you get into media. It is so ridiculous. I wish I sold a packaged good or something because with a media company — actually though, while growing it, it made me build confidence. It was like I was a new person, and I like grew my shell because it’s so complicated.

So really quick, with media, you don’t have one client. Like, if you were selling these glasses that I might need in a second to like actually see faces, because right now, I see just a bunch of baked potatoes because I stare at my screen for nine years in a row. Seriously, I had good eyesight. It’s really bad. And if anyone can help me here later — anyway, you don’t just have one customer; you have two because you have to give free value to one customer and basically give them all of your energy and make content and grow the audience, etcetera, for a customer that is not paying you; that’s your reader.

And then you also at the same time have to give just as much energy to the other customer, which is the advertiser. So there are barely few industries where you have to make that huge balance, and you can’t just focus on one, because if you only focus on one, you lose the other one. So that is something that I learned very early on.

But for media, when I started in 2015, there weren’t any newsletters out there. It was just like a few coming up. “Daily Candy” obviously was a big deal like a decade prior, but AOL kind of F’d it up, and it went from like 100-million-dollar valuation to like -100 million. And so, I think people stayed away from newsletters for a while.

But when I decided, “Okay, I’m going to start a company.” I was like, “Okay, I’m going to make a list. What am I good at?” And there was nothing on that list. I am not joking or trying to be cute. I couldn’t even lie to myself. I was like, “I know I’m not good at writing. I know I’m not good at this.” I wasn’t good at anything. And so I was like, “Okay, I’m going to become good at these things.” And so I decided that instead of making a list of what am I good at, what do I love to do — and I love to read magazines, which is like, “Okay, what are you going to do, be a professional magazine reader?” No. I decided to make my own magazine.

And I thought, the inbox can be such a toxic place. It’s such a wide space in the market for actual positive stuff, where you’re trying to refresh your inbox and not looking for the email from your professor that’s telling you something bad or good or a payment for your credit card, whatever. It’s like a gift in your inbox.

So, that’s the story I tell people. The actual story is I tried to make it a website. I had no idea how to make a website. I was on Squarespace for like 17 hours straight, and I just could not do it. So I was like, “What’s easier than a website? Newsletter.” And thank God I did that because having a newsletter means that you own your audience. You have those emails. It’s literally like going to somebody’s door every day and saying, “Hello, listen to me.” And they can open the door or they cannot open the door.

But having a website, it’s like being a car on the freeway passing the house. There’s no intimacy — I’m sorry. I made that up, so that was a really bad analogy or metaphor, whatever. Anyways, I was so lucky that I stumbled into that because I was differentiated in the market space. There was nothing like me. There were a few other newsletters coming about literally like that exact same time that I didn’t know about and then I found out about later on. But I was just in my lane. I didn’t know how media worked. I didn’t know any other media company. So I just did what I wanted to do.

And the newsletter today actually is very similar, in terms of topics, as it was nine years ago.

Zack Doherty: Well, as someone who can definitely relate to having an inbox that causes a lot of stress; I’m going to follow up with you about tips for that, another really unique part of your founder story is that you were able to build this newsletter to a very impressive 200-million-dollar valuation. And you did that all without raising any VC funding. For any aspiring founders in the room, what are your considerations on the merits and costs of bootstrapping versus raising VC?

Daniella Pierson: Yeah, well, first, I want to say in I think it was last year or the year before, I was named by Forbes as the youngest, wealthiest, self-made woman of color in the world. The only woman younger than me and wealthier than me was Kylee Jenner, and I was like, “I’ll take it.” But that was like a nice headline. And just to be totally honest with all of you, companies, just because they’re valued one year with something, it doesn’t mean that the value holds that same way.

I actually was one of the people who proved that value because someone bought a percentage of the company at that valuation. Usually, it’s like a funding around where it kind of is a fake valuation, and people around here are starting to think that and figure that out that profitability is acutally quite a nice word and not a bad word.

But I’m not going to sit here and be like, “Oh yeah, I knew I wanted to just have so much money in my 20s and not have to wait until I exited, if I ever exited, etcetera.” I tried to raise money. I came right to New York.

The way I monetized the newsletter, I knew that I could not monetize until I graduated. The dumb twin had one smart thing in her mind because I knew, “What if I get a dream advertiser and they’re like, ‘Oh, can we talk?’” And I had so many fake emails, like saraatthenews.com, because people didn’t know people, would email from Buzzfeed and stuff, and they’re like, “Oh, we should do a traffic swap because you’re driving so much traffic to our site.” And I’m like, “Oh, let me have Sarah answer you.” Sarah was my toenail.

So, I literally faked it ‘til I made it, and it was just me. And every newsletter subscriber, I literally could feel like I was getting them. I actually was such a stalker. During the time that I was in the classrooms and they were studying trees and very important stuff that I should never be in charge of, I was on Facebook looking at my friends — well, not really friends, I guess, people who I sent to high school with, looking to see who their new friends were because Facebook did chronological order there, so thanks, Facebook.

And I would be able to say, “Oh, these are people from their new college.” So then I would DM all of these people that were complete strangers to me. And as a sophomore, I don’t know if you guys can relate, it’s really hard to get a cool internship until you’re like a junior or senior. I wouldn’t know. I never got an internship. I was me, myself and I’ing.

But, basically, everyone wants something on their resume, and this was a time where stuff to put on your resume wasn’t just out there, everywhere. So I would DM all these random people. I never knew who they were, and I would say, “Hey!” And I didn’t look like a serial killer so at least they knew that much.” But I was like, “Hey, I work at this amazing company called The Newsette. All you have to do is just have 10 of your friends subscribe, and then you will become an official ambassador, and you can put that on your resume, etcetera.

And almost everybody I messaged was like, “Okay.” This is a lesson for everybody and might be so obvious, but you sometimes forget, even after doing business for so many years as myself. You almost have to put yourself in the other person’s shoes, like what do they want? They’re not going to do something for me because they care. No one cares. You have stuff to do. You got shit going on.

So, I was like, “I know these people want something to put on their resume, and they want something to be able to be a part of to get an internship, etcetera. So I made it that, and I pretended like I worked there instead of I started it. Because if they saw me and I started it, they’d be like, “Yeah right, this is like a Joe Schmo thing,” and it was. But I made it look like it was bigger than it was.

And I actually have a really good friend from B.U. that became an ambassador and had no idea that I was the founder of the company for like two years. And she’s still an incredible friend today. I don’t remember the question, honestly. I just started talking.

Zack Doherty: I think that’s the best fake it ‘til you make it story, but clearly you made it.

Daniella Pierson: It wasn’t building like a car or something; that would have been troublesome. Like, they don’t know, just get in, it will work. No.

Zack Doherty: But it obviously was so successful that it led you eventually —

Daniella Pierson: Oh, okay. Sorry. No, this is actually something that I told him I wanted to talk about, and then I just started talking, and the words escaped me. So, I told you that I really wanted to talk to all of you about the different paths of funding versus bootstrapping.

So I realized that I had to make money. Obviously, like in my very long story; sorry about that; I have ADHD, and I don’t think I took that medicine today, basically, I realized that I could not sell anything to advertisers until I graduated because I didn’t want a huge advertiser to be like, “Oh, can you be on a call,” and I’m like, “Oh no, I have math class,” like, you know, embarrassing. Not embarrassing here though. If you’re at Stanford, they’d be like, “Oh cool, okay.”

But so one month before graduation, it was just like exams and stuff, I started to monetize. I opened it up, and so many brands came to me, like Stitch Fix and Casper Mattress and all of those guys that I think are still out there. They would come to me, and I would be like, “Oh no, we don’t do advertising.” And then they want you. It’s like the girl that’s like, “I don’t like you.” It’s like, “Oh really,” and comes back with a dozen roses.

And so finally when I opened the doors to advertisement, I actually made $25,000 in one month. And for somebody with overhead of three people, me, myself and I, that was a lot. So I was like, “I’m going to New York.” So, me and my sister moved to New York, and I had that $25,000, and I had to make it work, like Project Runway says.

Literally, I just worked my ass off because I knew that was the money I had. It wasn’t like some genie was going to come and give me money. But then I quickly realized because I realized all these people were getting these cool profiles, and they were usually men. This was when I was 21, 22. I would email reporters and pitch myself, which I didn’t know was an ick thing to do for reporters because it’s usually like your PR team does it, but pitch yourself; who cares?

Anyway, they were like, “So how much have you raised,” every single one of them. And I was like, “God, I have to raise money.” And I should have known because when I was making the presentation, I was like, “What am I going to do with this money?” It was like what I was already doing was sustainably, but it would just take me less time. But everyone was getting funding, so I was like, “I’ve got to do it.”

So I weaseled my way into every room, and I actually got into some pretty important rooms because their associates or their secretaries were readers of “The Newsette” and were like, “Oh no, you’ve got to meet with this person.” Everyone I met with was an old white man, apologies for all of you out there. You’re great.

So, specifically, there was one old white man who all of you would know, very, very, very successful investor person and very old. And I did my whole presentation, and I was so excited. I was looking for a million dollars at a 10-million-dollar valuation, and that was that.

So I was doing my presentation, and he starts laughing. And I’m like, “Ha ha ha,” like laughing with him, like, “Oh, let’s all laugh together.” And then he stopped. I was like, “What’s so funny?” And he said, “You remind me of my granddaughter.” And I was stupid enough to not even see that as an insult, so I was like, “Tell me more!” So, I was like, “Oh really? She must be so smart and cool and entrepreneurial.”

And he got super dead-faced and said, “No, actually, she talks way too fast, and she has no idea what she’s talking about.” I’m not joking. And he literally sat there waiting for me to get up, and I actually got that social cue to get up and leave. And I cried the entire Uber way home. That sounds like the end of a Taylor Swift song, but it’s true. I did.

And I felt so sorry for myself, whatever. Something I’ve learned is the measure of success is not how much you win; it’s truly, and I sound like a baseball player from the ‘20s or something. It’s not about how many times you win; it’s about the times you fail and how you react to those failures.

And I’m somebody who sometimes can cry and feel sorry for myself, but I listen to one song, “Girl on Fire” or something like that, and then I’m like, “You know what? Ask everyone. I’m going to do it my way.” That’s one of my favorite songs, “My Way.” It’s like, I really chewed him up and spit him out, that investor guy. Again, it was another old, white man telling me that I couldn’t do what I wanted to do.

I skipped over this, but I actually failed my entrepreneurship project at B.U. It was very fair. I don’t know if you guys do something like this, probably not because you’re Stanford. But it was an entrepreneurship project. And how many of you guys know founders who have eight co-founders? Anyone? Not a good idea.

When you start a company that’s going to be super successful, and I’d love to split it in eight pieces after I have like 1 percent. Nope, not a good idea. But they were like, “Okay, we’re going to put all of you guys in groups of like 9 to 10,” like first wrong. “Then we’re going to have one of you guys fail.” Oh, okay. No, all of us fail if the entrepreneurship project doesn’t work in real life, but okay, one of us will fail. And the cherry on top was the professors, aka the investors or whatever in the real world, aren’t going to pick who fails. The other people in your group are.

Whoever came up with this — and I told the current dean now, and I think they took that away because I have shit on it so many times, but I was the one they picked to fail because I, instead of going out to drink or whatever after we were all done with the project; it’s something we did every single day for six months, I would go home and do my newsletter, and everyone knew that.

And so literally a guy that never brought his computer once to any of the meetings and like, “I’m sorry, you can’t do a project like that without a computer,” he didn’t fail; I failed. So that meant I failed all of my classes because it was like 70 percent of the grade. And so I got a nice letter from the dean saying, “If you don’t get this GPA, retake all of these classes on top of the new classes, on top of doing The Newsette, which my professors called ‘my little newsletter,’ you are going to be kicked out one semester before graduation.”

So, that was the hardest time in my life, and I literally felt like dying. And that’s when I actually did something about my OCD and went to get help. It was the hardest semester of my life, but I somehow did it, and I ended up graduating on the Dean’s List, which is like a much better letter to get from him. He was also an old white guy. I’m joking. I’m joking. And my dad’s one.

But I realized at that moment, “Okay, another old white guy.” Back to the investor guy, the really old, mean guy, the one that made me cry. I was like, “Am I going to let him define me?” Mm-mm. [Negative] Even though I should have been like, “Yes, sir. I am a failure, goodbye,” because he still is so successful I think. I don’t know. I don’t Google him everyday or everything. I’m joking. But I was like, “Am I going to let that happen?” And I said, “No.”

And I probably sounded so stupid. I didn’t tell anybody this, and thank God I didn’t because this was so far-fetched, and thank God I’m so stubborn. But I said, “Instead of getting a million dollars from four, white, old men in suits, like four investors, let’s say, I’m going to get a million dollars from 200 companies if it takes those many for advertising.” And that’s what I did.

And in 2019, we did a million dollars in sales. 2020 we did 7 million, and 2021 we did 40 million dollars in sales with eight figures of profit. And because I never took on an investor because, “Oh, they’ll laugh me out of the room,” I was able to write myself an 8-figure check and deposit it into my bank account. So, all the founder friends that I have; this is a cautionary tale, all the founder friends I had that raised at a billion dollar valuation, and oh, like 2 percent of the company, and they were like so cool and laughed about my company, I had like lots of money in the bank, and they had like 200K from secondaries, and then their company tanked.

And they bought like an 8-million-dollar house before. There are some horror stories. So people don’t tell you that. People don’t tell you the parts where it’s like, “Oh yeah, that person’s so successful,” but all these valuations finally caught up on them, and they’re never going to sell for that much; they’re going to sell for half, meaning they’re not going to get one penny.

“So that one million dollars you got in secondaries, but you bought like a 100-million-dollar house because you thought you were going to be a billionaire, sorry, you’re in debt now.”

So I was in a very unique position, not just among women or Latinas or whatever, among men too where I had a lot of money at 25 years old, and no one else that I knew did because it was all fake money. And so it worked out for me. And the reason why, again, the valuation of that company was so high is it’s four times our revenue that year, and we had an agency. We worked with companies like Amazon, Mattel, etcetera, and it was a lot of hustling and struggling. There were definitely lucky points.

DVF that sat here, I actually flew with her the first time I ever came to Palo Alto. We stayed in Anne Wojcicki, or Anne W’s guest house. And I was like watching Shark Tank with the Google heirs. They were so cute. But I came here because I convinced her for her “In Charge Movement” to do something with Facebook. And I met Mark Zuckerberg, and I shook his hand, and I started to sell him at 23 years old. And she was like, “Stop it!” And we like died laughing the whole way back. But she’s the one that opened so many doors for me, like introducing me to Amazon, and that became one of our biggest clients and was responsible for tens of millions of dollars in revenue over the years.

Zack Doherty: So, even though there were a lot of people early on who might not have believed in you, it sounds like you ended up finding a really strong support system of people who did.

Daniella Pierson: Yeah.

Zack Doherty: And for your second company, I know you were able to cofound it alongside Selena Gomez and her mother, Mandy Teefey?

Daniella Pierson: Yes.

Zack Doherty: The company, Wondermind, to destigmatize and democratize mental health.

Daniella Pierson: Yes.

Zack Doherty: One of the main concepts of Wondermind is this idea of mental fitness, exercising our minds like we do our bodies.

Daniella Pierson: Yes.

Zack Doherty: To a room full of Type A overachievers who could probably benefit from incorporating some of those practices, how should we be prioritizing mental health relative to our other priorities?

Daniella Pierson: So, the reason why I don’t get nervous for these things is because long gone are the periods where I care about what people think about me because I cared so much. So I will just share a secret with you all. I would be a fucking hypocrite if I told you guys I knew the answer to that question because I’m still not there, but I’m trying.

I started Wondermind with Selena and Mandy because I realized that I all of a sudden lived in this eight-figure apartment. I literally could spend hundreds of thousands of dollars a month and it didn’t even matter. I went from not even getting paid from “The Newsette” and only the incidentals and stuff. It was a really big job. And I wasn’t happy. And I realized that maybe the freedom was great, but the material stuff wasn’t making me happy. I wanted to figure out what would.

And I have realized that whenever I speak on a panel for Forbes or a keynote speaker at something like this and I am open about my OCD, ADHD, depression, that so many people come up. There was literally a conference where there was a huge celebrity that spoke after me, and then I had a line like I was a huge celebrity because people were like, “Wow, I can’t believe you say all those things about yourself. That’s kind of embarrassing.” And I’m like, “Yeah.” And some people would be like, “I have OCD too.” I realized that, wow, by me being so transparent, it was actually making people either be like, “Wow, she’s a fool” or like, “Wow, maybe we should talk about this more.”

So, I’m a strong believer in the only way to change the world, and this is a very capitalist mindset, but it’s a realistic one, the only way to change the world is to prove that your change can make a lot of money. And so instead of starting a fund or a charity or something, I said, “Let’s start a business.” And just like 15 years ago; I don’t know how old you guys all are, again, I have no glasses on; I’m 28, but 15 years ago, if I wanted to go to a yoga class, I had to drive in Jacksonville, Florida to the yoga studio, sweat, drive myself back, whatever. That was my only option. Then, all of a sudden, 10 or 15 years later, you can literally have access to hundreds of free workout apps, do yoga in like your car if you want to, unlike with the goat, and it’s free.

So, I realized, wow, that market was so small. And then as soon as people started realizing, “Oh wait, you can make money like “The Lemon” and “SoulCycle,” and all of a sudden it became bigger and bigger. Then, all of these resources are free for people. People don’t have to even pay for a gym membership because basically people are giving it to you for free because it’s all funded by VCs and Wall Street. It’s kind of funny to think about.

So I thought, we’re going to make this the biggest company ever and help people at the same time so that we can do the same thing that physical fitness did where in hopefully 5 or 10 years, people won’t have to even pay for a psychiatrist or a therapist because there’ll be so much money from Wall Street and from ambassadors paying just for them to be a user, you know?

So that was my goal and still is my goal to destigmatize and democratize mental health and to treat it like mental fitness. And so going back to the hypocrite part is I think everyone in this room, if you want to be an entrepreneur, you have to be really honest with yourself because just like the race to get into Stanford, you are up against the best and brightest. And if you don’t work your ass off, someone else will. And it’s okay if you don’t want that life. I envy people who don’t have that life, to be totally honest with you. And I have a curse where I just can’t stop it; I have to keep going.

And so hopefully I figure that out. But making therapy a priority, it still is a struggle for me. So, again, I don’t want to be a hypocrite and be like, “Oh, now I float in the air and meditate.” That’s not the case. But I do do yoga now like three times a week and started meditating. I thought it was a fake thing, but actually it’s real. And Nora, who’s in the front row, my right and left hand, she literally makes me feel bad if I don’t do my therapy sessions because I’m somebody who doesn’t like to talk about my feelings. I just want to keep going and going and going. And I’ve been in survival mode for the last nine years of my life.

And so, I would encourage all of you to not learn the hard way through multiple burnouts and just really tough parts of your life, to start your journey with those practices, with working out, with walking with friends, with making family a priority. I didn’t go home for Christmas for three years — making those things a priority before you even start, because here I am not having to hustle every day like I used to, and I still do, and I still missed Christmas last year.

So, I would just caution all of you guys and just take care of yourselves first because I learned the hard way that if you don’t take care of yourself, you can’t take care of anyone else.

Zack Doherty: One of the themes that I really drew from in your story is this idea of empowering others, which brings us to your latest venture, “Be a Breadwinner.” You just announced it last month in collaboration with J.P. Morgan and the CEO of their Wealth Management arm, Kristin Lemkau.

Daniella Pierson: Yes.

Zack Doherty: As you’re building this company and looking to the future, if you could use that to redefine tomorrow in one way, what would it be?

Daniella Pierson: That’s a great question. So, again, I told you guys in the beginning, and you guys are probably like, “I can’t follow this conversation.” But I promise you, there’s a [through line]. It’s like Dave Chapelle and his comedy specials. You’re like, “Where is he going?” And then at the end you’re like, “That was the first joke. It all connects.” I promise it’s going to connect.

I just saw him because one of my business partners and someone that I’m close to, his team is Kevin Hart, and I was lucky enough to watch him get the Mark Twin Award. And then Dave Chapelle came out, and I was like, “Oh my God!”

Anyways, sorry to disappoint; it’s just me. But it all comes back. So, everything I’ve been saying today is kind of the thesis of what I’m about to say, which is the mission of “Be a Breadwinner.” The mission of “Be a Breadwinner” is for anybody and everybody to build financial freedom and their future.

The one thing I have realized through all these years is money can’t buy happiness. Money can’t buy friends. Money can’t buy that stuff. But you what it can buy? Money can buy freedom. Freedom to what? Freedom to leave a toxic relationship, freedom to quit the job you hate and start a new job or start an entrepreneurial journey. Freedom to change the world.

So, to answer that question, if I could change the world in one day, it would be the mission of this company, which is make your barriers your building blocks. And so, I wish everybody could wake up tomorrow with zero bias of, “Are you a woman? Are you a woman of color? Are you a male of color? Do you have dyslexia? Do you have a mental health problem? Are you from the wrong side of town?” All those things, nothing matters. All that matters is you get to the mat, and whoever performs, performs. That’s what I wish we could have in society, and that’s what “Be a Breadwinner” is all about because it’s for men and women, but it’s for everybody, even people in this room.

Clearly all of you guys are empowered in some way because you’re here and thriving. But it’s for everybody to kind of ignite that voice in your head and say, “Wait, just because I’m a psychology student, but maybe I want to be an entrepreneur, do it, just do it!” Anybody can do anything, and I’m living proof of that.

My goal is to take that Forbes title and give it to someone else as quickly as I can because it is ridiculous that at 27, I was the youngest, wealthiest, self-made woman of color in the world when the male equivalent or the white male equivalent is probably 13 in someone’s basement making bitcoin or whatever. Did you make bitcoin? I don’t know.

That’s my concept. And J.P. Morgan, Wealth Management and Kristin Lemkau, they were such fantastic partners for the launch, the soft launch; it still hasn’t officially launched yet. But this is my ecosystem of everything that I have proven in my story and everything, and none of my businesses have ever been me first.

I didn’t want to start a blog about myself. I hate seeing myself in pictures. When I see my sister on TikTok, she’s my identical twin; I’m like, “Oh my God.” This is kind of like my way of taking everything that I’ve learned and my personal story and literally saying if a Latina with no funding, no pedigree, no belief from anybody except family members, no connections, no help, no anything was able to build that kind of not on-paper wealth, in-the-bank wealth at 25, anyone can do it. I promise. It’s just about breaking down those barriers and making them your building blocks.

The more barriers that you face, stack them up even higher because I promise you that every single weakness that you think is a weakness is actually your strength, and that’s something that DVS says all the time, so I totally just stole that from her, but it’s so true. That woman is an oracle. She literally has predicted my entire life.

But seriously, every person here is not only capable of changing the world, but also changing your life and other people’s lives. And just because maybe you have some sort of preconceived notion of what it is you want to do with your life, if you feel like you want to do something else, go for it. Just put yourself in a position where you can, and that’s where financial freedom and practicing financial fitness comes in.

Zack Doherty: I think that message has the power to inspire and help a lot of people, so thank you so much.

Daniella Pierson: It’s really hard to inspire this crowd because you guys already are great.

Zack Doherty: With our last couple months, I’d like to turn it over to the audience for Q&A. I think we’ll have time for one question, and then we’ll wrap up with a “View From The Top” lightning round tradition.

Daniella Pierson: Oh.

Zack Doherty: So, if you have a question, please raise your hand, and one of our mic runners will give you the mic.

[Trey]: Hi, I’m Trey.

Daniella Pierson: Hi.

Trey: So, last year, Andy Dunn came to speak with us, and he has bipolar disorder and spoke about how he’s managed that and built a business. I’m curious, with your mental health situation, A, how you managed depression, OCD and ADHD, but also, how have you turned those things into strengths for yourself through this process?

Daniella Pierson: Great question. And I love the hat. A dermatologist definitely told you you need to stay out of the sun; is that it? Yeah? I need one too. So, Andy Dunn and I actually did like a co-keynote for Forbes a couple years ago where we talked about having mental health illnesses and thriving past that, and that’s a really good question.

Again, everybody’s journey is different, but when I failed that project and I realized that it was so unfair that this group of people could just decide my fate, because my fate would have been getting shipped right back to Jacksonville, Florida, and I don’t think I would be here today. It made me so upset and angry and numb that my pre-nightly ritual — because when you have OCD, some people have rituals, like, okay, the difference between being psychotic and having OCD is that you know that things that you think aren’t true, but you still have the intrusive thoughts. And so it’s like, if I don’t look under the bed every night before I go to bed, my mom’s going to die. And you know it’s not going to happen, but it kills you.

So, those rituals, I would look under the bed until the bad feeling went away, and it wouldn’t go away, and I would slap my hand. And one time, they literally were bloody. And my boyfriend at the time who is still my partner today was actually the COO of my company for quite a while, but that was literally when I was just starting my company, he took it upon himself, and I will never be able to thank him enough for doing this, because I would have never done it myself, he found me a therapist, and he found me a psychiatrist. And I paid for it with my little affiliate money because I could not have my parents know about it.

And I actually got on medicine, and am still on it today, Prozac. Prozac has enabled me to completely take away all of the intrusive thoughts. So no longer do I feel like, “Ooh, I have to tap this five times” or anything like that, which it was such a curse. So it’s such a blessing not to have that. But my OCD does manifest in other ways, but that was crippling, so that’s something that I did.

My ADHD, I didn’t actually get diagnosed with that until like two years ago, and it explains a lot. But now I’m also on medicine for that, and I’m able to now, if I’m super anxious or if I’m obsessing about something, I can say, “It’s your OCD.” Everything is less scary when you can put a name and a fact to it. So it’s like in Monsters Inc — I have so many great analogies today — when the monster comes, but you’re like, “Oh, you’re cute, and I’m going to name you whatever,” then it’s not as scary. That’s kind of how it is now with my OCD, ADHD and depression, because it’s like, “Oh, it’s just my OCD coming out, and I have these tools and remedies to solve it.” I used to give up and just take a nap for three hours. “I’m not going to do that. I’m going to go for a walk, and I’m going to reinspire myself.”

So, truly for me, the way that I’ve been able to continue on is having a mission that’s greater than myself. I want to help people, and I want to change the world, and I can’t do that if I’m going to be depressed in my bed all day. I do it for every single person that thought that they could be successful, but decided not to even try because they have ADHD, because they didn’t go to an Ivy League school, because they were a person of color, because they got laughed out of a room by an old man with some sort of granddaughter issue, you know? That’s why I do it.

So, I think having a purpose that’s bigger than just making money, that also helps. I have really bad days. Nora can tell you, there are times where I just cry because it’s hard. If you’re an entrepreneur and you’re not getting punched in the face 20 times a day, you’re not doing it right; you just aren’t. And I’m the recipe for the person who should never be an entrepreneur, but I still am.

So I guess that literally closes it all out with the fact that like just because you have all of these barriers that history and statistics say they will not work for success, you can actually make a new recipe, and that’s why I built “Be a Breadwinner” and why I’m so excited for the launch is because it really is for somebody who wants to have success on their own terms and be a barrier-breaker, a bread-taker, the new mold of a money-maker.

Zack Doherty: Well, it’s clear nothing is going to get in your way or stop you. Before I let you go, we do have to finish with this “View From The Top” tradition. It’s a quick lightning round.

Daniella Pierson: Okay.

Zack Doherty: So I’m going to give you five short phrases, and you’re just going to finish it with the first word or short phrase that comes to mind.

Daniella Pierson: Oh God. I came back to college, and I have to do work now.

Zack Doherty: Pop quiz.

Daniella Pierson: Okay.

Zack Doherty: Biggest difference between you and your twin sister?

Daniella Pierson: She loved school.

Zack Doherty: Favorite article that you wrote for “The Newsette?”

Daniella Pierson: I wrote “The Newsette” every single day for five years from 5:00 a.m. to 10:00 a.m. every single weekday, even when we made a million dollars because I was so cheap with the money. So, I don’t even remember, but I’ve written thousands of things.

Zack Doherty: Mental fitness technique that works best for you?

Daniella Pierson: I actually just started doing yoga three times a week before work. I used to think that meditation was like a myth, but it’s totally not. I’m not good at it or anything yet, but the breathing works.

So, there’s something called a box breath situation where you inhale, one, two, three, four, five, hold it, one, two, three, four five, exhale, one, two, three, four, five, hold it, one, two, three, four, five. I might have messed that up and all of you guys are going to get an aneurysm. But I’m pretty sure it was that. And I’ve actually used that recently, so it’s a recent discovery.

Zack Doherty: Most played song by Selena Gomez?

Daniella Pierson: “My Mind and Me.”

Zack Doherty: I’m partial to “Same Old Love.” But we’ll let it slide. Last but not least, I know you were just on the Mario Lopez, “Access Hollywood” for an interview. Which one did you have more fun with?

Daniella Pierson: Oh, like Mario Lopez or you?

Zack Doherty: Yeah.

Daniella Pierson: I definitely had more fun with you.

Zack Doherty: There you go.

You passed the pop quiz. Daniella, it has been such a pleasure. Thank you so much, and we are so excited to see all your continued success.

Daniella Pierson: Thank you.

Zack Doherty: You’ve been listening to View From The Top podcast, a production of Stanford Graduate School of Business. This interview was conducted by me, Zack Doherty, the MBA Class of 2024. Lily Sloane composed our theme music. Michael Reilly, Elizabeth Wyleczuk-Stern and Jenny Luna produced this episode. Find this series on our YouTube channel or on our website at gsb.stanford.edu. Follow us on social media at Stanford GSB.