URGENT UPDATE: Startup founders across the U.S. are facing a familiar yet awkward challenge this Thanksgiving: explaining their entrepreneurial roles to skeptical family members. As reported by Business Insider, many founders are struggling to convince relatives that their work is legitimate and not a sign of unemployment.
This trend of Thanksgiving awkwardness is unfolding at dinner tables from coast to coast as founders attempt to articulate their often complex and non-traditional jobs. For instance, at 11:00 p.m. on Thanksgiving last year, Kieran White, co-founder of Curo, a Y Combinator-backed startup focused on electric vehicle charging, found himself in a Pasadena parking garage. His mission? To prove to his girlfriend’s family that he is indeed a successful entrepreneur, not a scammer.
White’s efforts began at the dinner table and escalated to a late-night trip to showcase his company’s logo on a sign. “I wouldn’t let it drop that I wasn’t unemployed,” White said. The perception of startup founders as unemployed is a widespread concern, particularly as many work in environments that are decidedly non-corporate.
The dilemma extends beyond just proving legitimacy. Founders frequently encounter skepticism due to the portrayal of startups in popular media, which often depicts entrepreneurs as either scammers or failures. As Dagobert Renouf, a French salesman for Comp AI, shared, the disconnect between startup founders and their relatives can be painful, especially when family members are achieving traditional milestones like buying homes or getting promotions.
Another founder, Raechel Lambert, founder of DNNR, expressed frustration over the communication gap, stating “When I say Jason Calacanis, it just sounds like some random name” to her relatives. The challenge of conveying the significance and potential of their startups is a common theme among founders.
For Chris Pisarski, co-founder of Crustdata, the issue was compounded by the need to take work calls during Thanksgiving dinner. With his development team based in Vietnam, Pisarski explained that there is no Thanksgiving holiday in Vietnam. His family responded with confusion, questioning why he was working when he wasn’t seeing immediate financial returns.
Not all families are unaware of the demands of startup life. Chloe Samaha, founder of Bond, shared that her entrepreneur parents engage in business discussions during the holiday. However, she faces her own challenges with relatives skeptical of AI technology, the focus of her startup. Samaha noted, “Thanksgiving is for business talk and grilling,” but added that her aunts and uncles often criticize the tech she represents.
Founders have expressed that while some family members understand the entrepreneurial journey, others remain skeptical. Karun Kaushik, whose startup Delve recently secured $32 million in Series A funding, shared a moment of relief that his family loves him for who he is, not just what he does.
As Thanksgiving approaches, many founders are bracing for another round of potential misunderstandings and awkward conversations. White, who left his girlfriend’s family with a visual proof of his company’s existence last year, is set to face the same scrutiny again. “We’ll see this year,” he remarked, hinting at the ongoing struggle to earn validation in the eyes of relatives.
As families gather this holiday season, startup founders everywhere are encouraged to reflect on their journeys and the challenges that come with explaining their innovative roles. The emotional impact of these conversations is significant, highlighting the gap between traditional career paths and the evolving landscape of entrepreneurship.
With Thanksgiving just around the corner, the urgency for founders to articulate their work and dispel misconceptions is more critical than ever.
