Start Before You’re Ready and Let Confidence Catch Up with Davide “Davi” De Pierro

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0:32Don't wait for a problem to remind you you're uncovered. Policies start as low as$29 a month. Get protected in minutes at nextinsurance.com. That's N-E-X-T insurance.com. How do you speak life into somebody else that wants to make a jump and to try something new, to write a book, to start creating content, but they can't bear to put themselves on video? What advice can you give to someone to make a transition? It always looks impossible until it happens. You know, whoever out there is thinking, I can't do this, I can't do that. That's just a story that you're telling yourself. It's not based on in reality.

1:08It's not based in fact. My story prior to six months ago was also, oh, TikTok or videos. What are you, nuts? It suddenly becomes very obvious and very doable once it happens. You have to fight through that doubt. You have to fight through the feelings of maybe a little bit of embarrassment. You can't wait for the doubts or the uncertainties to disappear in order to begin. You have to begin while you're still not so sure. And then you'll be rewarded for that effort. And you'll gain confidence as you go because you'll suddenly see the results and say, wow, now I believe in myself because I see it.

1:46I'm on this journey with me. Each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. I'm ready for my close-up. Hi, and welcome back. I'm so excited you're here with me this week. I'm so excited for this episode. You have no idea. Okay, I want to welcome my guest today, Davide. Let's hope I don't completely debauch his name. DiPriaro, which I did, but okay. He's better than Davide on TikTok and Instagram. He is a writer, a storyteller, and he's exploring questions of love relationships and heartbreak with playful seriousness. He's freaking hilarious.

2:24He has a following of over 4 million across TikTok and Instagram. He is a voice for those navigating love, memory, and loss. And he is also a newly defined as an author. He's also a lawyer, which I had no idea. Happy day. Thank you so much for being here today. Thanks so much, Heather. I'm excited to be here. Oh, I can't take it. Okay, you guys, If you have not followed him on Instagram before, first of all, where have you been? Like, come to life. I watched you, Davide, like, scale and blow up in the past, I guess it's six months. It's like astronomical growth. What has been going on with you?

3:00I don't know what's been going on. Prior to starting this, exactly around six months ago, first on TikTok, and then eventually I carried it into Instagram maybe three months ago. I was, as someone used to say about me, chronically offline. I was that guy that girls say they want the one that doesn't use social media. That's like the new thing now. Oh, find yourself a guy that doesn't use social media. But I just randomly tried it one day because I want to give credit where credit's due. A girl I was dating at the time said, you know, you should try TikTok. And I said, what, are you out of your mind?

3:35At the time, I was 37. I'm 38 now. So I was like, 37, I'm going to do what I'm going to make videos about. I'm going to dance. There's nothing I can do. I'm going to take my shirt off or something. and she said, no, no, just talk about whatever you want. And so I did exactly that. One day I went into the car because I wanted the privacy of not being seen. I was so ashamed that I was actually doing it. And now the car is a thing. People enjoy seeing me in the car, but I went into the car just for the privacy of it. And I just started talking about whatever was on my mind, the kind of things I would talk about with friends, you know?

4:08And it kind of immediately just took off. And it's been, you're right. It's been a trajectory that I think is uncommon from what people are telling me in terms of the speed of it. So I don't know what's going on, but people seem to like it. I think mainly I'm just saying what people relate to, what's already on their mind. And maybe I'm saying it in a way that they find entertaining or enlightening. I don't know. But I just have fun with it, really. And it's easy for me because it's just me being myself. Oh, my gosh. I love that for you. I'm so excited for you. Okay, so this was, I was stalking you.

4:45I call it stalking when I start DMing people, I don't know. I was stalking you online, trying to get you to do the show. And when we first spoke, you explained to me, you have this whole other life, which was really shocking to me because, and this happens to me a lot, when people follow you online, they only know what they see online. So they think that's everything, right? So for me, I just, I know your personality from Instagram, from your videos, from your lives. And I think I know you. However, I'm hoping you can enlighten everybody on your backstory and this other side of your life that people don't see online.

5:17Yeah, I want to say, first of all, that the person that I am online is not so far as a character. Because I know that for some people, they put on a complete different character online. Maybe they even have a different accent and that's fine. And they're having fun with it, that they're playing a role. The person I am in those videos is one of the people that I really am. In other words, I mean, you know, we all have a little bit of a multiple personality going on. And especially you may have heard the phrase is become popular as of late code switching, which is when people have kind of different dialects depending on who they're hanging out with.

5:56So so when I'm hanging out with my Jersey boys at the diner, I sound exactly like I do in the video. But when I'm in court, so I'm a lawyer, when I'm in court, obviously I'm not saying, hey, your honor, listen, you know, the defendant is guilty. You know, I'm talking a different dialect that perhaps my accent gets slightly toned down, though I'm certain it's still very Jersey. And so I have different parts of me that are not in the videos. The most obvious, I guess, would be what I really do. Well, what I have done for the last 14 years, which is I'm an attorney, but what I've always wanted to be is the storyteller, a writer.

6:35And I just never thought that I would actually do it. I thought that I would just keep it all to myself. And then when this social media virality happened, it occurred to me, oh, my goodness, there's these millions of people now who seem to like me. Maybe I can show them what I'm writing. And that's exactly what I did. I published. It's an audio book for now. I also thought that would be best for now because my followers know me through my face and my voice. Rather than giving them something in print, I thought it would be a little bit more intimate if they could hear me. And so I recorded an audio book.

7:08It's called The Letters I Never Sent. You can find the link in my bios on TikTok or Instagram. And basically, it's the backstory of the content because it explores all of the same themes. what I speak most about in the content is relationships, dating, love, romance, and all that comes with that. And really, this is almost like as if I published my journal. Essentially, it's something that I've written for years. I've been writing it for over 10 years. And like I said, I was just going to keep it to myself. And now that I'm no longer chronically offline and people know that I exist, I figured, you know what, let me give them something else in case they want to know more.

7:46And so far, people have been loving it. And that's really exciting for me. It feels validating, obviously, when people enjoy what you're doing, what you're saying. And I'm excited to show people more of me because, you know, the videos are inherently comical. But, you know, great comedy, I think, is just saying something serious in a funny way. And so what I do in the book is I delve a little bit more deeply and profoundly and I hope emotionally in the same subject matter. and so far the returns have been have been positive people are really liking it people are really enjoying it and so that's that's great and i hope more people i hope more people check it out because i think it's it's really really great oh my gosh your content's amazing your book's amazing okay but thank you for explaining that however i want to come back for a minute let's run this back so one of the things i think is cool when we spoke offline you talked a lot about your family the importance of family to you like what that means to you if you could talk a little because i think that shows like a whole unique side of you especially in this day and age around the importance of family, how you got into law.

8:49Just give us like a brief overview. Oh, you know, certainly, certainly. Yeah. So I'm Italian. So family is incredibly significant. We've always eaten together. We've always done everything together. Everyone is always around. Sometimes that's too much, but yeah, there's just pros and cons to everything. My father became an attorney later in life in his thirties, which is interesting to me now, because now I'm in my thirties and it's, you know, To realize that he started being a lawyer at that age is incredible still, that he reinvented himself later in life. And so he became a lawyer in his 30s.

9:28You're reinventing yourself at the same age he did, but go ahead. Yeah, exactly. A bit of a different reinvention. Although he is supportive of my online presence, he's excited about it as well. But the reason I became a lawyer is because I just followed what essentially at that time had become the family business. It was basically like a pizzeria, but lawyers. It was a family business because my father, after he worked for a brief moment with some larger firms, eventually decided I'm going to open on my own thing. He opened up his own practice. My older brother, who went to law school before me, followed suit.

10:02And then it became clear to me, not really knowing what I wanted to do. All right, I guess I'm just going to follow along and join the family business, which just so happens to be law. So yeah, so for years, I've worked with my father, with my brother. There was a period of time where we even had my best friend working with us, then he moved on to another firm. So you can imagine, it was just like a hangout, and we were practicing law simultaneously. So yeah, that's how I got into it. It's just my usual tendency to be with family, which I think is a part of me. uh we're also uh i come from a very religious family um my parents uh have always from the day i was born we were going to church on sundays so when you add the mixture of religious family and an italian family it all just was a perfect storm for the fact that i was unable to at any point distance myself but we'll see how that goes now i'm starting to break away a little bit but but they're still involved they're excited they're happy that i'm doing this and i haven't quit my job yet to be clear yeah being the operative word so explain to me this because i i find this interesting, someone who I reinvented myself at 43.

11:08And there's a lot, at least for myself and for a lot of people, I know there's a lot of trepidation around, we have an identity with a job. So you as a lawyer, me as a former C-suite in corporate America, right? Like you start identifying in that way and to actually jump from that, leap from that and say, okay, now I'm going to go try this new thing. I could fail. I don't know how I'll do it. That for a lot of people, that's super scary. How has that transition been for you? Honestly, for me, it is a welcome transition. I've always hoped I could find something else to be passionate about. I always knew it had something to do with storytelling.

11:45I didn't quite think it would happen this way. There were times where I thought maybe it would never happen. But for me, the transition is only exciting. Now, it could be that I come from a very entrepreneurial background with my father, who was always starting a new business, was always reinventing himself. I mean, my father at 18 marries my mother and goes from New Jersey to Italy. And he starts a business in Italy at 18 years old, you know, with just a high school diploma and barely any Italian language skills. Then a few years pass by and we come back here and one thing leads to the next. And next thing you know, he's trying law school.

12:21So I had a family that instilled in me a sense of possibility, a sense that you can always do something different, that it's never too late to reinvent yourself. And there's a line that my father would often quote, I think it may be from George Eliot, but if not, I'll just quote my father, who says that it's never too late to be who you might have been. And I think that we all harbor so many different facets. We are not one dimensional, We're not just a lawyer. We're not just a father. We're not just a son. We can be so many things in this life. And life is long. It's the longest thing we do. And I think that we shouldn't be afraid to try something, even as silly as doing a video in your car, because anything can happen.

13:09And for me, it seems, in fact, like now anything is possible. So it's exciting. That is. That's so exciting. Okay, so let's get to your content. Thank you for the backstory. Your content is hilarious. And it's coming from, I think I'm so funny. Your content is like every time hilarious and so dry, sarcastic, like you kill it. The weirdest thing for me is that, and I know for a lot of my friends, in a world where everyone's out dating and so many of these guys are completely clueless morons. How do you know what's going on? You know everything that's going on in every, like, are you actually a 45 year old?

13:48woman. I don't know. Like, who is feeding you this information? School us a little bit. Listen, I wish that I could tell you that there was a secret. The closest thing I can come to giving credit elsewhere is the fact that I did grow up around a lot of women. My mother was the eldest of nine, and five of which were girls. So I had a ton of aunts. And again, being an Italian family, because sometimes people might think, okay, great, you have an aunt. So what? You see them at Thanksgiving. No, that's not the way it works with us. Okay. These women raised me. Okay. They, they were always around. We were always together.

14:23We spent so much time together. And then as I got older, the conversations obviously got more profound and deeper. And then we would talk about dating and they would give me advice and I would tell them I had a crush and they would say, well, this is what you want to do. So I certainly had a lot of guidance in my life from women. Beyond that, I think some of it is intrinsic. Perhaps I came into the world this way. I'm observant. I'm neurotic. I'm hyper self-aware. So I'm always seeing myself outside myself. And I think that certainly causes anxiety at times, but it also causes an ability to understand what's happening around you or at least take note of it and be informed by it.

15:00So I pay attention. I pay attention. I listen. I try to learn. And so I guess I've just accumulated some understanding. I don't think I really have all the answers. I've never position myself as a relationship guru or a coach of some kind. I don't think I ever would. You know, I just say the things that I think should be obvious and which is why the character, again, it's not fully a character. It is a side of me in the car or elsewhere. Now I'm even, you know, doing the videos in other places. I think he comes across as so exhausted because he is saying what he thinks should be obvious. And all the women commenting agree is obvious but somewhere along the way someone is missing this and what i do is i speak directly to men which is i think interesting the character is speaking to men but it's mainly women who are consuming it and just like high-fiving each other which is fine i think it's fun but yeah i don't know i think that's the best i can respond to where i get this from and is it the same for you in real life like so for example you're out on the weekend hanging with your guys they all don't get it and you just get it?

16:09That is what I find interesting. I don't know many men who don't get it. So my friends are fairly like-minded. I know people are not going to say, give us, send us their name and numbers, but they're fairly like-minded. We have these conversations together. Really, the things I talk about in the videos are exactly the things I talk about with my friends when we're hanging out at the diner. In fact, when this all happened, they started saying, I can't believe that you're going viral, literally just saying the things that we talk about whenever we hang out. But I don't know where these men are, but I know that they're out there.

16:42I've heard of them. But for the most part, I want to give credit to my friends and say that they're fairly well-adjusted men. You know, we got some problems and nobody's perfect, but they're typically intelligent and empathetic and not totally clueless. Meet a different guest each week. Confidence queen. Starting the year with a wardrobe refresh, Quince has you covered with Lux Essentials that feel effortless and look polished. They're perfect for layering, mixing, and building a wardrobe that lasts. Their versatile styles make it easy to reach for them day after day. Quince has all the staples covered, from soft Mongolian cashmere sweaters that feel like designer pieces without the markup, to 100 % silk tops and skirts for easy dressing up, to perfectly cut denim for everyday wear.

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20:29I ask you to try to find your passion. Okay, so that's good to know there are others out there. All right, for the win. Davide, what about this? As anyone knows, when you start growing an online audience, haters are going to come. It's just something that happens. Far for the course, we know that. Are you getting hate? And are you ever getting hate from former girls you dated saying like, oh, why didn't you show up that way when we dated? That's a great question. So I have to be honest. Again, as I said earlier, I was always offline, But I always heard about how scary a place the internet is and how there's so much bullying.

21:02And honestly, I have gotten 99 % positive feedback. Occasionally, you'll get a comment, always from a guy, that'll say something on the lines of, oh, you're pandering to girls. Oh, you're such a simp, which I had to look up because I'm 38. I had to look up the internet language. But that's so few and far between that I hardly ever even noticed. Generally, the comments are positive. I seem to generally just be in a little bubble of people who like me. So I'm protected from that. As far as my exes go, maybe this is controversial, but maybe it shouldn't be. I have good relationships with them. They're all very excited about this.

21:44I've only had two serious exes. So I've dated many girls, but I've had two real what I consider girlfriends where you actually, you know, did life together. And both of them are super excited. And I think they would probably not say a bad word about me, not because the relationship was perfect, but because I think there was a general understanding between us that we were all trying our best. No one was malicious. No one was thoughtless. We made mistakes, but I have a really good memory of both of them, and they do of me too, so they say, because again, I speak with them. You know who might disagree with the persona in the content?

22:25Some girls that I casually dated. You know, well, why didn't you keep following up? Why don't you keep dating me? Well, why didn't you respond? For the same reasons that we didn't become a couple. Evidently, we just, you know, we didn't connect well enough for me to continue to see you or speak to you. And that's, I think that's different. But I don't think I've ever been malicious to someone or thoughtless to someone that I was seriously dating. May I have been a little bit careless in my casual dating? I'm sure that I have. And to them, I issue a formal apology here and now. Please don't come after me.

23:00Okay, something interesting that you said is that you would never give relationship advice. And what's funny is after following your content, I always start thinking to myself, once I knew that, you know, formerly were a lawyer, still are a lawyer for the moment, but that obviously you have this trajectory ahead of you. And it's so obvious that you're going to spin off out of what your current main job is to doing something very different. I can see that clearly. But for me, what I anticipated you would say is that you would start getting into coaching women online, like having a show where you're giving feedback.

23:30But you said, obviously, you're not qualified to do that. To me, it's like the obvious next step for you. You know, I don't want to close the door to that. You know, I was being self-deprecating as usual. That's just my general tone. But I could see myself potentially doing some kind of a show. I don't know what that looks like now. But I don't know that I would enjoy coaching. So I don't know if I would go that far. Anything is possible. But I've never wanted to be a teacher. I love the literature. I was a literature student in college. And one of the options was, okay, I could go be a professor.

24:03But I thought the idea of having to teach people something felt like it would really trigger my impatience. So I just followed my father and my brother and went into the law, but where I could be less patient with people and just tell them what to do. But, you know, anything is possible. I just I don't think I want to position myself as a guru, coach, mentor. But in terms of having a show, that I see differently because that would allow me to still do what I do enjoy doing, which is just entertaining and storytelling and sharing ideas and thoughts and connecting. And I feel a little bit safer in that space rather than being responsible for people.

24:39And, you know, well, he told me to do this and it didn't work out. And now, I mean, that's the lawyer in me too, trying to be risk averse, trying not to have liabilities here. But yeah, I don't know. We'll see. Anything is possible, Heather. As we know, one minute you're a lawyer or you're working in corporate America, and then the next minute, you know, you're in your beautiful kitchen having a conversation with me. OK, so I like that you were able to make this leap so quickly and with confidence into this online world and, you know, blow up so quickly. Then for you to take that leap of faith and say, OK, wait a minute, now I think I'm going to bring my journal forward and turn this into a book.

25:13What did that look like and how did you make that decision to actually do that? For me, it was as simple as an eagerness to begin to position myself the way I see myself. And so what was happening online, though it was exciting and was opening up doors, I didn't want to let it get so far where I was going to be pigeonholed into, oh, this guy's a comedian. I never considered myself a comedian. Again, that's another thing that could happen someday. Maybe I'll do some comedic writing or maybe some stand-up. I don't know. It's not being ruled out. I'm being approached with things like that, and we'll see what happens.

25:49But I wanted to very quickly take this audience and bring them into the thing I care about most, which is real, profound storytelling. Not just the one-minute videos that are fun and entertaining and even helpful, I think. But I wanted to give them the thing that I think I do best. I didn't want to limit myself to just these videos. And I saw it as an opportunity. I saw it as an opportunity to finally let the world know, look, this is what I also do and care about. And I hope you'll care about it, too. And so that's what I did. And we'll see where it goes. So let's talk a little bit about the letters I never send.