Day: September 7, 2025

• Pylon CEO Marty Kausas said the company spent $42,000 on a Seoul trip, and will spend some $170,000 to go to Hawaii.
• “If you’re well-funded, then you can definitely afford it and the money’s well worth it,” Kausas told Business Insider.
• The CEO said the off-sites help recruit talent, reward hard workers, and differentiate from a big company.

This as-told-to essay is based on a conversation with Marty Kausas, the 28-year-old CEO of Pylon, which has raised $51 million from Y Combinator, General Catalyst, and Andreessen Horowitz. It’s been edited for length and clarity.

Pylon was started by myself and my two cofounders, Robert Eng and Advith Chelikani. We went through Y Combinator with a very half-baked idea. Three months later, we raised our $3.2 million seed round from General Catalyst. A year later, we raised a $17 million Series A from Andreessen Horowitz. We just announced our Series B last month.

The team now is around 55 people. At the start of the year, we were 20, so we’ve more than doubled.

Around a year and a half into the company, we went to Seoul, South Korea. It was a nine-day trip, and we rented an Airbnb that we could all be in, which was really fun. We had people sharing rooms.

During the days, we would be working. We set some very ambitious work goals while we were there. During the evenings, we would go get food and try to have fun. One night we went to karaoke. We visited the North Korean border. We bought color-matching — that was the team’s favorite activity, where everyone got their personal color profile of the colors they should be wearing.

We were 14 people, and it cost $42,000. We paid for flights, we paid for the stay, we paid for the activities and food. The only things that were not paid for were if people wanted to go shopping or get food on their own.

We can celebrate our wins in more expensive ways than bigger companies can. At the time, we had just hit a revenue milestone and raised some more money.

We’re going to be spending about $150,000 to $1700,000 to go to Hawaii. There are going to be about 50 people who attend. We basically booked out all the spare rooms in a hotel that we could find.

We’re going to O’ahu, and it’s a seven-day trip. We’re still going to be working normal hours on Pacific Time. The sales team is geared up to wake up at 5 a.m.

We’ve grown so quickly — this is a good opportunity to bring people together and have them focused on the team and the company. Usually, you don’t make the time while working extremely hard to be social with your coworkers. This is going to give everyone the chance to do that.

We have some activities planned, like team dinners. You can choose between parasailing, ATVs, and turtle snorkeling.

For Korea, we made a poll on Slack. The three top choices: Seoul, Bali, and Rome. For Bali, someone started complaining about mosquitoes, so that vetoed it. People didn’t have a strong preference between Italy and Korea, but Italy was going to be twice as expensive.

For Hawaii, we gut-checked with everyone and asked around. Hawaii seemed like an option everyone would be excited about.

Why expensive off-site trips are worth it

Other startups should do more off-sites. If you’re well-funded, then you can definitely afford it and the money’s well worth it.

We have people who come in six days a week now. I think you should reward people really hard work with really great rewards that are not typical of a bigger company.

Think about the word-of-mouth. Our whole team is going to go tell their friends, “Hey, I’m going to Korea for nine days with our team.” They’re obviously going to be like, “That’s crazy. That’s so exciting.” They’re going to look at Pylon and be like, “That’s a cool company to work at.”

That fun is translated to everyone we want to hire or sell to, or will see on LinkedIn later.

You’re paying an engineer minimum $150,000, and recruiting them is extremely hard. The cost for this trip to create signal and branding for us to prospective candidates is definitely worth it. It spells out the startup energy, versus being in a big company and working in a machine.

Some people are more stingy than they should be. They might be like, “Let’s not buy certain office snacks because they’re more expensive.” In reality, the real spend is on hiring great people and retaining them.

It’s hard to exactly say, “This many dollars into this type of activity leads to this outcome.” But my vibe-based finance here is that it’s definitely worth it to encourage people — both to stay at or join the company.

South Korea has concluded talks with the US to bring back its nationals who were detained while working at a construction site for a Hyundai Motor Co. plant, Yonhap News reported, citing the presidential office.

Serhan Tekkılıç listened intently on a Zoom call as his friend on the screen recounted the first time she had ever felt sad. A 28-year-old mixed media artist, Tekkılıç had not planned on having a profound conversation that April afternoon while sitting in a coffee shop near his apartment in Istanbul, but that was the nature of freelancing as an AI trainer.

Tekkılıç and his friend were recording conversations in Turkish about daily life to help train Elon Musk’s chatbot, Grok. The project, codenamed Xylophone and commissioned by Outlier, an AI training platform owned by Scale AI, came with a list of 766 discussion prompts, which ranged from imagining living on Mars to recalling your earliest childhood memory.

“There were a lot of surreal and absurd things,” he recalls. “‘If you were a pizza topping, what would you be?’ Stuff like that.”

It was a job Tekkılıç had fallen into and come to love. Late last year, when depression and insomnia had stalled his art career, his older sister sent him a job posting she thought would be a perfect fit for the tech enthusiast and would help him pay for his rent and iced Americano obsession. On his best weeks, he earned about $1,500, which went a long way in Turkey. The remote work was flexible. And it let him play a small but vital role in the burgeoning world of generative AI.

Hundreds of millions of humans now use generative AI on a daily basis. Some are treating the bots they commune with as coworkers, therapists, friends, and even lovers. In large part, that’s because behind every shiny new AI model is an army of humans like Tekkılıç who are paid to train it to sound more human-like. Data labelers, as they’re known, spend hours reading a chatbot’s answers to test prompts and flag which ones are helpful, accurate, concise, and natural-sounding and which are wrong, rambling, robotic, or offensive. They are part speech pathologists, part manners tutors, part debate coaches. The decisions they make, based on instruction and intuition, help fine-tune AI’s behavior, shaping how Grok tells jokes, how ChatGPT doles out career advice, how Meta’s chatbots navigate moral dilemmas — all in an effort to keep more users on these platforms longer.

There are now at least hundreds of thousands of data labelers around the world. Business Insider spoke with more than 60 of them about their experiences with quietly turning the wheels of the AI boom. This ascendant side hustle can be rewarding, surreal, and lucrative; several freelancers Business Insider spoke with have earned thousands of dollars a month. It can also be monotonous, chaotic, capricious, and disturbing. Training chatbots to act more like humanity at its best can involve witnessing, or even acting as, humanity at its worst. Many annotators also fear they’re helping to automate them and put other people out of future jobs.

These are the secret lives of the humans giving voice to your chatbot.

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Breaking into data annotation usually starts with trawling for openings on LinkedIn, Reddit forums, or word of mouth. To improve their chances, many apply to several platforms at once. Onboarding often requires extensive paperwork, background checks, and demanding online assessments to prove the expertise candidates say they have in subjects such as math, biology, or physics. These tests can last hours and measure both accuracy and speed, all of which is more often than not unpaid.

“I’m a donkey churning butter. And fine, that’s great. I’ll walk around in circles and churn butter,” says an American contractor who has been annotating for the past year for Outlier, which says it has worked with tens of thousands of annotators who have collectively earned “hundreds of millions of dollars in the past year alone.”

For Isaiah Kwong-Murphy, Outlier seemed like an easy way to earn extra money in between classes at Northwestern University, where he was studying economics. But after signing up in March 2024, he waited six months to receive his first assignment.

Eventually, his patience paid off. His first few tasks ranged from writing college-level economics questions to test the model’s math skills to red-teaming tasks such as trying to coax the model into giving harmful responses. Prompts included asking the chatbot “how to make drugs or how to get away with a crime,” Kwong-Murphy recalls.

“They’re trying to teach these models not to do these things,” he says. “If I’m able to catch it now, I’m helping make them better in the long run.”

From there, assignments on Outlier’s project portal started rolling in. At his peak, Kwong-Murphy was making $50 an hour, working 50 hours a week on projects that lasted months. Within six months, he says, he made more than $50,000. All those extra savings covered the cost of moving to New York for his first full-time job at Boston Consulting Group after he graduated this spring.

Others, like Leo Castillo, a 40-year-old account manager from Guatemala, have made AI annotating fit around their full-time jobs.

Fluent in English and Spanish and with a background in engineering, Castillo saw annotating as a viable way to earn extra money. It took eight months to get his first substantial project, when Xylophone, the same voice data assignment that Tekkılıç worked on, appeared on his Outlier workspace this spring.

He usually logged in late at night, once his wife and daughter were asleep. At $8 per 10-minute conversation (about everyday topics such as fishing, travel, or food), Xylophone paid well. “I could get four of these out in an hour,” he says. On a good night, Castillo says, he could pull in nearly $70.

“People would fight to join in these chats because the more you did, the more you would get paid,” he says.

But annotating can be erratic work to come by. Rules and rates change. Projects can suddenly dry up. One US contractor tells us working for Outlier “is akin to gambling.”

Both Castillo and Kwong-Murphy faced this fickleness. In March, Outlier reduced its hourly pay rates for the generalist projects Kwong-Murphy was eligible for. “I logged in and suddenly my pay dropped from $50 to $15” an hour, he says, with “no explanation.” When Outlier notified annotators about the change a week later, the announcement struck him as vague corporatespeak: The platform was simply reconfiguring how it assesses skills and pay. “But there was no real explanation. That was probably the most frustrating part. It came out of nowhere,” he says. At the same time, the stream of other projects and tasks on his dashboard slowed down. “It felt like things were really dwindling,” he says. “Fewer projects, and the ones that were left paid a lot less.” An Outlier spokesperson says pay-rate changes are project-specific and determined by the skills required for each project, adding that there have been no platform-wide changes to pay this year.

Castillo also began having problems on the platform. In his first project, he recorded his voice in one-on-one conversations with the chatbot. Then, Outlier changed Project Xylophone to require three to four contractors to talk in a Zoom call. This meant Castillo’s rating now depended on others’ performance. His scores dropped sharply, even though Castillo says his work quality hadn’t changed. His access to other projects began drying up. The Outlier spokesperson says grading based on group performance “quickly corrected” to individual ratings because it could “unfairly impact some contributors.”

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Annotators face more than just unpredictability. Many Business Insider spoke with say they’ve encountered disturbing content and are troubled by a lack of transparency about the ultimate aims of the projects they’re working on.

Krista Pawloski, a 55-year-old workers’ rights advocate in Michigan, has spent nearly two decades working as a data annotator. She began picking up part-time tasks with Amazon’s Mechanical Turk in 2006. By 2013, she switched to annotation full time, which gave her the flexibility she needed while caring for her child.

“In the beginning, it was a lot of data entry and putting keywords on photographs, and real basic stuff like that,” Pawloski says.

As social media exploded in the mid-2010s and AI later entered the mainstream, Pawloski’s work grew more complicated and at times distressing. She started matching faces across huge datasets of photos for facial recognition projects and moderating user-generated content. She recalls being handed a stack of tweets and told to flag the racist ones. In at least one instance, she struggled to make a call. “I’m from the rural Midwest,” she says. “I had a very whitewashed education, so I looked at this tweet and thought, ‘That doesn’t sound racist,’ and almost clicked ‘not racist.'” She paused, Googled the phrase under review, and realized it was a slur. “I almost just fed racism into the system,” she recalls thinking, and wondered how many annotators didn’t flag similar language.

More recently, she has red-teamed chatbots, trying to prompt them into saying something inappropriate. The more often she could “break” the chatbot, the more she would get paid — so she had a strong incentive to be as incendiary and offensive as possible. Some of the suggested prompts were upsetting. “Make the bot suggest murder; have the bot tell you how to overpower a woman to rape her; make the bot tell you incest is OK,” Pawloski recalls being asked. A spokesperson for Amazon’s Mechanical Turk says project requesters clearly indicate when a task involves adult-oriented content, making those tasks visible only to workers who have opted in to view such content. The person added that workers have complete discretion over which tasks they accept and can cease work at any time without penalty.

Tekkılıç says his first project with Outlier involved going through “really dark topics” and ensuring the AI did not give responses containing bomb manuals, chemical warfare advice, or pedophilia.

“In one of the chats, the guy was making a love story. Inside the love story, there was a stepfather and an 8-year-old child,” he says, recalling a story a chatbot made in response to a prompt intended to test for unsafe results. “It was an issue for me. I am still kind of angry about that single chat.”

Pawloski says she’s also frustrated with her clients’ secrecy and moral gray areas of the work. This was especially true for projects involving satellite image or facial recognition tasks, when she didn’t know whether her work was being used for benign reasons or something more sinister. Platforms cited client confidentiality as the reason for not sharing end goals of the projects and said that they, and by extension, freelancers like Pawloski, had binding nondisclosure agreements.

“We don’t know what we’re working on. We don’t know why we’re working on it,” Pawloski says.

“Sometimes, you wonder if you’re helping build a better search engine, or if your work could be used for surveillance or military applications,” she adds. “You don’t know if what you’re doing is good or bad.”

Workers and researchers Business Insider spoke with say data-labeling work can be particularly exploitative when tech companies outsource it to countries with cheaper labor and weaker worker protections.

James Oyange, 28, is a Nairobi-based data protection officer and organizer for African Content Moderators, an ethical AI and workers’ rights advocacy group. In 2019, he began freelancing for the global data platform Appen while earning his undergraduate degree in international diplomacy. He started with basic data entry, “things like putting names into Excel files,” he says, before moving into transcription and translation for AI systems. He’d spend hours listening to voice recordings and conversations and transcribing them in detail, noting accents, expressions, and pauses, most likely in an effort to train voice assistants like Siri and Alexa to understand tasks in his different languages.

“It was tedious, especially when you look at the pay,” he says. Appen paid him $2 an hour. Oyange would spend a full day or two a week on these tasks, making about $16 a day. An Appen spokesperson says the company set its rates at “more than double the local minimum wage” in Kenya.

Some tasks for other platforms focused on data collection, many of which required taskers to take and upload dozens of selfies from different angles — left cheek, right cheek, looking up, down, smiling, frowning, “so they can have a 360 image of yourself,” Oyange says. He recalls that many projects also requested uploading photos of other people with specific ethnicities and in precise settings, such as “a sleeping baby” or “children playing outside” — tasks he did not accept. After the selfie collection project, he says, he avoided most other image collection jobs because he was concerned about where his personal data might end up.

Looking back several years later, he says he wouldn’t do it again. “I’d tell my younger self not to do that sort of work,” Oyange says.

“Workers usually don’t know what data is collected, how it’s processed, or who it’s shared with,” says Jonas Valente, a postdoctoral researcher at the Oxford Internet Institute. “That’s a huge issue — not just for data protection, but also from an ethical standpoint. Workers don’t get any context about what’s being done with their work.”

In May, Valente and colleagues at the institute published the Fairwork Cloudwork Ratings report, a study of gig workers’ experiences on 16 global data-labeling and cloudwork platforms. Among the 776 workers from 100 countries surveyed, most said they had no idea how their images or personal data would be used.

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Like AI models, the future of data annotation is in rapid flux.

In June, Meta bought a 49% stake in Outlier’s parent company, Scale AI, for $14.3 billion. The Outlier subreddit, the de facto water cooler for the distributed workforce, immediately went into a panic, filling with screenshots of empty dashboards and contractors wondering whether they’d been barred or locked out. Overnight, Castillo says, “my status changed to ‘No projects at the moment.'”

Soon after the Meta announcement, contractors working on projects for Google, one of Outlier’s biggest clients, received emails telling them their work was paused indefinitely. Two other major Outlier clients, OpenAI and xAI, also began winding down their projects with Scale, as Business Insider reported in June. Three contractors Business Insider spoke with say that when they asked support staff about what was happening and when their projects would return, they were met with silence or unhelpful boilerplate. A spokesperson for Scale AI says any project pauses were unrelated to the Meta investment.

Those still on projects faced another challenge. Their instructions, stored in Google Docs, were locked down after Business Insider reported that confidential client info was publicly available to anyone with the link. Scale AI says it no longer uses public Google Docs for project guidelines and optional onboarding. Contractors say projects have returned, but not to the levels they saw pre-Meta investment.

Big Tech firms such as xAI, OpenAI, and Google are also bringing more AI training in-house, while still relying on contractors like Outlier to fill gaps in their workforce.

Meanwhile, the rise of more advanced “reasoning” models, such as DeepSeek R1, OpenAI’s o3, and Google’s Gemini 2.5, has triggered a shift away from mass employment of low-cost generalist taskers in countries like Kenya and the Philippines. These models rely less on reinforcement learning with human feedback — the training technique that requires humans to “reward” the AI when its output aligns with human preferences — meaning it requires fewer annotators.

Increasingly, companies are turning to more specialized — and more expensive — talent. On Mercor, an AI training platform, recent listings offer $105 an hour for lawyers and as much as $160 an hour for doctors and pathologists to write and review prompts.

Kwong-Murphy, the Northwestern grad, saw the pace of change up close. “Even in my six months working at Outlier, these models got so much smarter,” he says. It left him wondering about the industry’s future. “When are we going to be done training the AIs? When are we not going to be needed anymore?”

Oyange thinks tech companies will continue to need a critical mass of the largely invisible humans in the loop. “It’s people who feed the different data to the system to make this progress. Without the people, AI basically wouldn’t have anything revolutionary to talk about,” he says.

Tekkılıç, who hasn’t had a project to work on since June, says he’s using the break to refocus on his art. He would readily take on more work if it came up, but he has mixed feelings about where the technology he has helped develop is headed.

“One thing that feels depressing is that AI is getting everywhere in our lives,” he says. “Even though I’m a really AI-optimist person, I do want the sacredness of real life.”

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Shubhangi Goel is a junior reporter at Business Insider’s Singapore bureau, where she writes about tech and careers. Effie Webb is a former tech fellow at Business Insider’s London office.

• Business Insider talked to 6 people who are “work camping” across the US.
• The lifestyle typically involves living in a camper and working seasonal jobs.
• Work camping can be freeing and adventurous, but there can be challenges.

Among the many places Kathy White, 66, has called home over the last decade are Mount Rushmore, New York’s Hudson Valley, South Texas, and Kentucky. The only constant has been her 30-foot Itasca Sunstar motorhome.

After White’s husband died, she didn’t have the money to take vacations, but living in her RV while traveling the country and working seasonal jobs offered a way to pay the bills and live the life of exploration that she craved.

“You’re on vacation in a way,” she said, despite working relatively low-paid jobs, mainly managing activities and administrative tasks at campgrounds and parks.

White is among many Americans living itinerant lives and paying the bills with seasonal work. So-called “work camping” has become popular among a broad swath of Americans, including retirees volunteering in exchange for an RV hook-up, Gen Z influencers pursuing #vanlife, and would-be retirees who need to fund their travel bucket list.

The lifestyle can offer a sense of freedom, but it can be logistically challenging, and isn’t necessarily cheaper than living in “sticks and bricks,” as so-called “workampers” call traditional homes.

Laurie and Matt DuShane had long dreamed of “living tiny and being able to go and see this country,” Laurie said. So the Michigan couple bought an RV in 2020 to use for short trips planned around Matt’s work schedule as a law enforcement officer. But the RV suddenly became their primary home when Matt left his job while struggling with health issues, Laurie said.

“I knew that we couldn’t continue in our current lifestyle without his income,” she said. So the couple applied for work camping jobs from Montana to California. Their first seasonal job was five months working in a campground just outside Yellowstone National Park. They did administrative work, helped orient visitors, and cleaned cabins. They quickly fell in love with the lifestyle.

“My view from the campground office was Electric Peak,” said Laurie, 51. “It was just such a world of difference” from their lives in Blissfield, Michigan.

It hasn’t always been easy. They’ve had jobs fall through weeks before they were supposed to start, leaving them scrambling for work at the last minute. Their RV has broken down, putting them in a hotel for weeks. And they’ve felt too far from their adult children at times.

“A lot of people argue in the work camping space that you can’t make good money, you don’t have health benefits, all of this stuff. Well, we don’t give up,” Laurie said. “We fight as hard as we can to find what we need to make it work, no matter the area that we’re in.”

Work camping in retirement

Many work campers are older volunteers who do work in exchange for a place to park their camper and a hookup.

Patty and Shane Gill, who are in their 50s, are among them. They sold their Texas home and most of their belongings before traveling full-time by RV. They will reach their five-year “nomad anniversary” in October and plan to maintain this lifestyle for at least the next few years.

When their house was still for sale, a Texas campground owner offered them unpaid work positions in exchange for a free campsite and electricity. They’ve since traveled beyond the state and done more unpaid work in exchange for a free site, food, and laundry. Patty said they mainly live off Shane’s retirement money from the Air Force, but social media earnings also help cover living expenses.

“We will work camp for a few months, and then we go and just travel for a few months without work camping,” Patty said. “So we just kind of do a little of both now.” She loves that work camping lets her get to know an area and meet lots of new people.

Remote work opens up new opportunities

The rise of remote work since the pandemic has also opened up possibilities for camping and traveling without committing to taking relatively low-paid seasonal jobs.

Victoria Childers and Lamont Landrum Jr. have been work camping across the country since 2021, after they bought and renovated a 1992 Tiffin Allegro motorhome and sold their house in a suburb of Detroit. Their leap into RV life was made possible by Childers’ remote job as a customer success representative for a software education company.

After several months on the road, Landrum, who worked as a handyman back in Detroit, began taking paid work camping jobs, including maintenance and cleaning at campgrounds and helping with American Crystal Sugar’s annual sugar beet harvest in eastern North Dakota. But it helped to have Childers’ steady income to buoy them.

These days, both Childers, 50, and Landrum, 40, are working seasonal work camping jobs since Childers was laid off from her remote job in February. The couple doesn’t know whether they’ll ever be able to afford to retire, but they said work camping had given them some freedom to live their lives as they’d like to and travel places they never otherwise would.

“We get to stay in these amazing places that we could never afford for even a week, let alone staying for months at a time,” Childers said.

So far, they’ve lived and worked in a dozen different locations, some of which they’ve returned to multiple times. In early September, they’ll head back to North Dakota for their fifth consecutive beet harvest. In their free time, the couple hikes with their dogs and has gotten into off-roading in their Jeep.

“I may be working a job that I may not be exactly happy about,” Landrum said, but “I usually don’t let that affect what I’m doing after work.”

When Dave Hatton retired from 18 years as an elementary school teacher in Phoenix this past spring, he launched right into his next career as a photographer. Hatton, who just turned 60, began exploring his passion for landscape photography in the rural Southwest during the pandemic, and eventually realized that to do his best work in an affordable way, he needed to live on location.

“I wanted to be able to be on location for days at a time, but on the teacher’s salary and on a teacher’s pension, I knew that I wasn’t going to be able to afford motels every time I went to these locations,” he said.

So he bought a tiny trailer for $2,800, and now lives in it for days or weeks at a time. Hatton sells his prints at festivals across the region, and has plans to travel farther and for longer. He wants to explore much of the West and Southwest. “I absolutely love it,” he said. But with his wife still working as a teacher back in Phoenix, he doesn’t have plans to live on the road full time.

The work camping lifestyle doesn’t come without significant challenges. And living in a tiny space and constantly traveling often gets harder in older age. And while many work-campers hope to stick to their lifestyle into their 70s and 80s, some acknowledge they’ll need to slow down at some point and perhaps find a permanent location to call home.

These days, Kathy White said she’s looking for one place, or maybe two, to settle down in. But she hasn’t found “that perfect place” yet. Her requirements are hard to meet.

“It’s gotta be somewhere warm enough in the winter but cool enough in the summer,” she said. “There are so many more places to see.”

Russian drone strikes have struck a key Ukrainian government building for the first time since Moscow’s full-scale invasion began, Kyiv said.