The Thanksgiving conversation startup founders dread: explaining their job

• This Thanksgiving, founders face explaining their businesses to friends and family — and proving they're not unemployed.
• Six founders told Business Insider their stories of Thanksgiving awkwardness.
• One founder said that they have to battle AI skeptics at dinner; another said their family didn't get why they had to take calls.

At 11:00 p.m. on Thanksgiving day last year, Kieran White brought his girlfriend's family to a Pasadena parking garage. His goal: prove that he's not a scammer.

White cofounded Curo, a Y Combinator-backed startup focused on electric vehicle charging. His girlfriend's family didn't fully get it, though. White's defense started at the Thanksgiving table, and eventually moved to the living room. While the family played games, White sat with his girlfriend's grandfather explaining his job.

Eventually, he decided to high-tail it to a parking garage to point out his company's logo on a sign to showcase its existence.

"I wouldn't let it drop that I wasn't unemployed," White said. "I always thought that everyone knew what YC was. It was like: 'Picture Harvard, but for startups.' It was a hard message to convey."

How exactly should a founder explain their job? It can be difficult to prove that the work is real — and even more difficult to show that the startup will still be around for a few years. It doesn't help that the work environment is often decidedly non-corporate, or that founders sometimes sleep on couches and air mattresses. Meanwhile, a slew of recent TV shows have framed some founders as scammers and flame-outs.

So, as you gather around the Thanksgiving table, consider lighting a candle for the startup founder, faced with defending their job to doubtful aunts and uncles. Six of them told Business Insider about their Turkey Day tussles.

The startup founder's Thanksgiving awkwardness

Dagobert Renouf said that his ex-wife's family didn't take him seriously.

The French salesman for Comp AI used to run a startup with his former spouse. After years of building, the couple had gotten their first customer. "Finally, we got some traction," he said.

His ex-wife's three siblings were at the Thanksgiving table that year. One was buying a house, another was having a baby, and the third was promoted at a bank. Meanwhile, Renouf and his then-wife were grateful to have made $200.

"It was a bit painful," Renouf said. "People could be excited. It's just that they didn't necessarily get it. It's such a disconnect, when you build your own business, with somebody who'd never done that."

Raechel Lambert knows that "disconnect" well. The New Hampshire-based DNNR founder said that she and her relatives sometimes sound like they're speaking a different language.

"When I say Jason Calacanis, it just sounds like some random name," she said.

Founders have long had difficult explaining their jobs — and proving that they will be successful — to family members. When Brian Chesky founded Airbnb, he told his mother that he was an entrepreneur. His mom's response: "No, you're unemployed."

For Chris Pisarski's family, the rub was that he had to take calls on Thanksgiving.

Pisarski's startup, Crustdata, has a dev team based in Vietnam. There's no Thanksgiving in Vietnam, Pisarski said, so he needed to take calls. "You're doing this now?" he remembered his family saying. "You're not making any money for this."

It didn't help that Pisarski recently moved from a top-floor Chelsea apartment to a basement, or that he had to raise his voice on the call during a "relaxing" holiday, he told Business Insider. He also had to skip out on the family tradition of mall shopping and movie-watching on Black Friday.

"It was a little bit of concern, but mostly confusion," Pisarski said.

The families who get it

Not everyone is so perplexed by the work of being a startup founder. But the clued-in family can prove a different kind of challenge, though — they may start asking hard-hitting questions.

Bond founder Chloe Samaha's parents are both entrepreneurs. Thanksgiving is for "business talk and grilling," she said.

"My dad's favorite question is: How many customers did you close today?" Samaha said.

On the other side of the table are Samaha's aunts and uncles, who she says are critical of AI and believe the tech is taking people's jobs. (Bond, Samaha's company, is an "AI chief of staff.") The San Francisco-based founder uses the example of the calculator with these family members; students continued to learn math even after its advent, after all.

Karun Kaushik remembers when people doubted him. In those pre-revenue days, with less funding to point to, Kaushik found it difficult to justify his work.

He's clearly serious now: Kaushik's startup Delve recently closed $32 million in Series A funding. Over vegetarian turkey — cauliflower with carrot feathers — his family talks about everything but work.

"They love me for who I am, not what I do," Kaushik said. "I try not to talk about it."

Can families learn to respect their founder children's work? It depends. I asked White, who brought his girlfriend's family to the garage on Thanksgiving day, whether he thought the defense worked.

"We'll see this year," he said.