In this episode of Creating Confidence, Italian-American attorney Davide De Pierro shares his journey from traditional legal practice to online content creation. At age 37, he began creating TikTok videos about relationships from his car, which unexpectedly went viral. While maintaining his family law practice as a safety net, he has expanded into storytelling through his audiobook "The Letters I Never Sent."
De Pierro discusses how creators can build confidence through action rather than waiting for perfect circumstances. He explores the importance of authenticity in content creation, explaining how staying true to oneself leads to stronger audience connections. The episode covers his approach to balancing his established legal career with his creative pursuits, and how he navigates the transition between these different professional spheres.

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Davide De Pierro's Italian-American heritage has profoundly influenced his life choices. Following in his family's footsteps, he became an attorney in the family law practice, working alongside his father and brother. Beyond his legal career, Davide nurtures a private passion for storytelling, inspired by his father's entrepreneurial journey and belief that "it's never too late to be who you might've been."
Initially hesitant to create content, especially at age 37, Davide began making TikTok videos from his car at his girlfriend's encouragement. His authentic discussions about relationships quickly gained traction, leading to unexpected viral success. While his online persona represents a specific side of his personality—the one his friends in New Jersey know well—it remains genuine, earning support from both family and former partners.
Davide expanded his creative pursuits by publishing an audiobook titled "The Letters I Never Sent," a collection of writings spanning a decade that explores themes of love and heartbreak. Despite his initial reservations, the audiobook has received enthusiastic response from thousands of listeners who find it healing and relatable. This success has helped Davide transition from being perceived as just a comedian to establishing himself as a serious storyteller.
Drawing from his experience, Davide emphasizes that self-doubt shouldn't prevent action, as confidence often grows through doing. He encourages creators to maintain authenticity rather than imitate others, noting that genuine content creates stronger audience connections. Currently, Davide is gradually transitioning from his legal career while keeping it as a safety net, demonstrating his practical approach to pursuing creative ambitions.
1-Page Summary
Davide De Pierro offers insight into his life, highlighting how his Italian-American heritage has shaped his values and career choices, and his private pursuit of storytelling reflects a belief in continuous self-reinvention influenced by his father.
Davide emphasizes the importance of family in his Italian culture, reflecting a tight-knit dynamic where family members frequently do things together. He exhibits pride in his lineage and how it informs his approach to both personal and professional life.
Davide’s decision to pursue law was deeply influenced by his familial connections. He humorously compares joining the family law practice to taking over a family-run pizzeria, indicating the natural progression of following a family trade. He worked alongside his father, brother, and at one point, his best friend.
In addition to his legal career, Davide harbors a private passion for storytelling and writing. This interest reflects a broader perspective on life and career choices, shaped significantly by his father's life narrative.
His father, starting a business in Italy at age 18 with little more than a high school diploma and basic Italian language proficiency, embarked on a diverse career path, i ...
Davide's Personal and Professional Background
Davide's journey to becoming an online content creator started with hesitation but led to unexpected success and a newfound identity on TikTok.
Davide, originally "chronically offline" and shy about the idea of making TikTok videos, especially at the age of 37, was encouraged by a girl he was dating to explore the platform. He began creating content from the privacy of his car, too ashamed at first to let his girlfriend watch him film. Despite this initial embarrassment, he found that making videos in his car not only provided him with privacy but later became a recognized part of his brand.
Davide's content, which consisted of him simply speaking his mind about topics similar to those he would discuss with his friends, quickly received rapid and positive attention. This type of growth was considered uncommon, signifying that his authentic voice resonated with a wide audience.
While Davide De Pierro's online persona isn't a completely different character, it showcases the side of him that he reveals when he's with friends in New Jersey. Although he behaves differently as a lawyer in court, the person in the videos is indeed a facet of his true self. Over time, as he gained experience, his voice and composure evolved, which can be observed when comparing his newer content to videos from five months prior.
Davide speaks of receiving mainly positive feedback from his viewers and maintains ...
Davide's Transition To Becoming an Online Content Creator
David De Pierro's transition from lighthearted content creator to profound storyteller comes to life as he publishes his long-held private writings in the form of an audiobook.
The audiobook, titled "The Letters I Never Sent," showcases Davide's emotional side as he explores themes of love, relationships, and heartbreak—an expressive departure from his more humorous video content. With writings collected over a decade, Davide sought to provide an intimate experience for his followers, believing that an audio format would leverage his familiar voice to add depth to his heartfelt stories.
Davide was hesitant to share his writing, expecting that it might not receive much attention. To his surprise and delight, his audiobook has been welcomed with enthusiasm by thousands of listeners who have found it to be beautiful, healing, therapeutic, and relatable. People have resonated so strongly that they are asking for a printed version and are eagerly inquiring about future works or sequels.
Davide, who didn't want to be pigeonholed as just a comedian, has made a conscious effort to redefine himself. Known for his one-minute videos, Davide wanted to transcend that medium and share profoundly resonating stories that demonstrate his passion for storytelling.
Despite his initial reluctance to share his writings, Davide now receives nothing but love and positive feedback for his work. His audience has expressed a connection to the book, appreciating its worth and asking for more content, which has been both exciting and validating for Davide.
He acknowledges that while the book is primarily a work of fiction, it is based on his own experiences and observations, which has sparked speculation that it may be his memoir. Davide finds amusement in this interpretation but hopes that regardless of how it is perceived, readers will find enjoyment and univers ...
Davide's Journey as an Aspiring Author
Davide De Pierro shares his personal journey and insights, providing advice to those considering a shift in their professional or creative life. He addresses the common fears and reservations that one may experience when undertaking such changes.
Davide emphasizes that the stories we tell ourselves about what is impossible are just that—stories. These narratives, rooted in doubt and fear of embarrassment, are not a reflection of reality. He shares from his own experience of creating content for platforms like TikTok that one must not wait for doubts to disappear before beginning. Instead, Davide suggests that starting even when unsure is beneficial, and that taking action can actually grow confidence and diminish doubts over time.
He also encourages people to pursue diverse paths and take risks, given that the worst-case scenario is one ends up where they started, implying that there is much more to gain than to lose by trying new endeavors. Davide believes we shouldn't hesitate to chase different opportunities because life is long and full of possibilities.
In his advice, Davide highlights that time will pass regardless of our actions, so it’s better to use it to try new things. He reasons that one will either discover something new or end up back where they started, making a compelling case for taking leaps toward one's dreams. He assures that rarely do people regret pursuing their passions and suggests that, by taking risks, one has the opportunity for growth and fulfillment.
Stressing the importance of authenticity, Davide encourages creators to be genuine in their content, as this fosters a real connection with their audience. He cautions against the temptation to copy others and underscores that an original voice is more effective than an imitation. This urges creators to remain true to themselves as a means of distinguishing their work and resonating wit ...
Advice For Career/Creative Transition
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