At 11:00 p.m. on Thanksgiving Day last year, Kieran White found himself leading his girlfriend’s family into a dimly lit Pasadena parking garage — an undeniably odd post-dinner excursion. His purpose, however, was not to extend the evening’s festivities but to defend his professional reputation. White wanted to prove, once and for all, that he was genuinely employed and not, as some quietly suspected, a scammer.
White is the cofounder of Curo, a Y Combinator–backed startup dedicated to improving infrastructure for electric vehicle charging. To those immersed in the world of technology and entrepreneurship, such credentials would be immediately impressive. Yet his girlfriend’s family—intelligent, kind, and well-meaning though they were—struggled to grasp what his work actually entailed. The challenge began inconspicuously enough around the Thanksgiving dinner table and then stretched into the living room, where the family gathered to play games while White attempted to summarize the complexities of his job to his girlfriend’s grandfather. Words, however, failed to persuade. Exasperated but determined, he opted for a grander gesture: he ushered the family out to a parking garage to physically point at his company’s logo emblazoned on a charging station sign — tangible proof that Curo was real.
“I just couldn’t let them keep assuming I was unemployed,” White confessed later. “I always believed that everyone knew about YC — as if it were obvious to compare it to Harvard, but for startups.” This analogy, he realized, carried little weight outside the tech bubble, where ‘Y Combinator’ might sound more like a math term than an entrepreneurial pedigree. Conveying what he did, and why it mattered, was far harder than he expected.
Indeed, White’s dilemma highlights a broader question that countless startup founders face: how does one convincingly explain the nature of entrepreneurial work to a skeptical audience—especially family members for whom success traditionally looks like a steady paycheck, not a dream financed by venture capital? Proving that one’s labor is legitimate can be tricky enough; proving that the venture will still exist a few years down the line is exponentially harder. The challenge becomes steeper when one’s workplace lacks the familiar trappings of corporate life—offices, HR departments, or even consistent salaries. Many founders work from spare bedrooms or coworking spaces, often subsisting on coffee and little sleep, occasionally crashing on couches or air mattresses. When popular media consistently portrays entrepreneurs as either visionary disruptors or disastrous fraudsters, suspicion becomes inevitable.
So this Thanksgiving, as families gather around tables laden with turkey and pie, perhaps a moment of empathy is due for the founder in the room—the one caught between explaining their burning ambition and defending their legitimacy to doubtful aunts or incredulous uncles. Several founders recently shared how these holiday conversations unfold, revealing that proving one’s professional worth to family can sometimes be the hardest pitch of all.
French entrepreneur Dagobert Renouf remembered that his ex-wife’s family never fully respected his efforts. At the time, he and his then-wife had spent years struggling to build their small technology venture, finally acquiring their very first customer—a milestone that, in the startup world, represents a breakthrough of enormous emotional weight. “At last, we’d gained some traction,” he said. But at that year’s Thanksgiving celebration, his personal pride stood awkwardly beside the traditional measures of success displayed by his ex-wife’s siblings: one had just bought a house, another was celebrating a newborn, and the third had been promoted at a bank. By contrast, Renouf’s revenue tally stood at a mere two hundred dollars. “It was painful,” he admitted, recalling the mix of excitement and disconnection. “They weren’t unkind — they simply couldn’t understand. Unless you’ve built something from scratch yourself, it’s hard to grasp what progress looks like in that context.”
New Hampshire–based founder Raechel Lambert expressed similar sentiments. As the creator of DNNR, she frequently feels as though she and her relatives inhabit different linguistic worlds entirely. “When I mention someone like Jason Calacanis,” she joked, “it sounds to my family as if I’m just tossing out a random name.” This cultural gap between startup founders and everyone else is not new. Even Brian Chesky, who would later become the billionaire cofounder of Airbnb, once told his mother that he was an entrepreneur — to which she replied bluntly, “No, you’re unemployed.”
For Chris Pisarski, founder of Crustdata, the friction took another form entirely. His family’s frustration centered on the fact that he could never fully step away from work — not even on Thanksgiving. With his development team operating out of Vietnam, where no such holiday exists, he was expected to join work calls despite the festive chaos at home. “You’re doing this now?” his family asked incredulously. “You’re not even making money from it!” The situation was compounded by personal sacrifices: Pisarski had recently moved from a stylish top-floor apartment in Chelsea to a basement unit, and on top of that, his obligation to speak loudly on work calls actively disrupted the supposedly ‘relaxing’ family day. He skipped long-standing traditions like shopping trips and movie outings on Black Friday. “It was mostly confusion,” he reflected. “A little bit of concern, but mostly just not understanding.”
Yet not every founder faces only skepticism. Some are surrounded by relatives who understand entrepreneurial life all too well — which comes with its own complications. Take Chloe Samaha, founder of Bond. Her parents are both entrepreneurs, and as she put it, Thanksgiving in their household means “business talk and grilling.” Her father’s go-to question, delivered with affectionate scrutiny, is invariably, “So, how many customers did you close today?” Meanwhile, her aunts and uncles tend to represent the opposing camp: critics who distrust artificial intelligence and lament its influence on the workforce. Since Bond functions as an “AI chief of staff,” Samaha often finds herself explaining that technological tools don’t replace people entirely — much like calculators didn’t eliminate mathematics, but rather changed the way humans engage with it. Her dinners become debates disguised as family bonding sessions.
Others, like Karun Kaushik, recall earlier Thanksgivings filled with doubt and skepticism. When his startup Delve was still pre-revenue and fundraising remained a long shot, Kaushik struggled to justify his endeavors. Now, years later, having secured $32 million in Series A funding, the dynamic at the dinner table has mellowed dramatically. Over a vegetarian ‘turkey’ centerpiece—an artful combination of cauliflower and carrot feathers—his relatives no longer interrogate him about metrics or milestones. “They love me for who I am, not for what I do,” Kaushik said with quiet gratitude. “I try not to bring work up anymore.”
So, can families truly come to respect and understand their entrepreneurial children? The answer, it seems, varies. When asked whether his daring parking-garage demonstration ultimately convinced his girlfriend’s relatives, Kieran White paused with a wry smile before replying, “We’ll see this year.” His response, half confident and half humorous, perfectly encapsulates the perennial plight of the founder: forever pitching, forever proving, even to those closest to them.
Sourse: https://www.businessinsider.com/startup-founders-explain-job-family-thanksgiving-2025-11
