• Vinay Hiremath, a co-founder of Loom, just wrote about finding purpose after selling the company.
• Software company Atlassian acquired Loom for $975 million in fall 2023.
• The 32-year-old has climbed mountains and joined DOGE. Now, he's in Hawaii.

Vinay Hiremath is grappling with one of success's unexpected downsides.

The 32-year-old cofounded Loom, a video communication company that was acquired by Australian software company Atlassian in October 2023 for about $975 million.

In a recent blog on his website, the former chief technology officer of Loom wrote about giving up $60 million in pay when he decided not to work for Atlassian. Instead, he said he briefly evaluated building a robotics company and climbed two Himalayan peaks. Hiremath also worked for Elon Musk and Vivek Ramaswamy's Department of Government Efficiency for a month.

"I started to realize that, although the mission of DOGE is extremely important, it wasn't the most important thing I needed to focus on with urgency for myself," he wrote. "I needed to get back to ambiguity, focus on my insecurities, and be ok with that for a while. DOGE wasn't going to fix that."

Hiremath, who broke up with his long-term girlfriend, also wrote about the challenges of tying his identity to his startup.

"When we went through our first round of layoffs, this company my ego was hitched to had suffered a massive blow, so I lost myself. This whole chapter of Loom has created a complex web of internalized insecurities I must now work hard to disentangle and free myself from."

His co-founder, Joe Thomas, remains CEO.

A Wednesday X post in which Hiremath shared a link to his blog has been viewed nearly 540,000 times. The post garnered over 500 comments, many from other tech enthusiasts and startup founders thanking Hiremath for opening up.

Hiremath wrote he is in Hawaii, learning physics and aiming to start another company "that manufactures real-world things" — even if he doesn't find as much success as he did at Loom.

And he's wrestling with philosophical questions about his identity and how he relates to others.

Hiremath did not respond to a request for further comment.

Purpose beyond the job

Hiremath is part of a wider community of suddenly wealthy people or early retirees who struggle to find purpose after decades of working. Experts in personal finance say the feeling is common.

"When we have more money than we could ever spend, most people quit their job — but the job provides many of us with structure, a sense of purpose, and a great deal of our social interaction. Remove this, and it leaves a big void," Robert Pagliarini, a financial advisor who wrote a book about sudden wealth, previously told Business Insider.

Clayton Christensen, an academic and business consultant best known for his theory of "disruptive innovation" and his views on purpose, long said that focusing on a purpose is essential for personal and professional success.

The Rhodes Scholar and Harvard Business School alumnus, who died in 2020, wrote that he had to "think long and hard" about his purpose.

"Over the years I've watched the fates of my HBS classmates from 1979 unfold; I've seen more and more of them come to reunions unhappy, divorced, and alienated from their children," Christensen wrote in a 2010 Harvard Business Review article. "They didn't keep the purpose of their lives front and center as they decided how to spend their time, talents, and energy."

• Tamara Ponzo Brattoli's retirement plans changed after her son's sudden death in 2018.
• Brattoli took a job at Costco to pay her bills, but she worries about her financial future.
• Many older Americans face financial struggles after losing loved ones, which affects their retirement.

Tamara Ponzo Brattoli, 57, was set on retiring comfortably in her 60s. She raised three children with her husband and worked as a professor at a community college in a Chicago suburb.

However, when her son died suddenly, she said, in addition to the grief, she became much more worried about her retirement.

Her son Anthony was a college student who died after working abroad in the summer before his senior year. His death hit the family hard, and Brattoli struggled to return to work. After taking a leave of absence to grieve and returning for a few semesters, she retired from teaching, took her pension early, and got a job as a warehouse manager at Costco to help her make ends meet.

She's proud of herself for lessening her financial burden and for getting back to work in a role she could handle, even though it was in a completely different industry.

Though she makes enough to live comfortably, she said she's worried her pension won't keep up with inflation, which could make her finances tighter down the line. She wishes she had more resources and guidance to solidify her finances after Anthony's death and had saved more money earlier in life in case tragedy struck.

"I regret not maximizing my options during that awful time," she told Business Insider. "I needed better help to make decisions but did not know where to turn, and I do not feel like my former employer, or my union, or my therapists really knew how to help me."

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Brattoli is one of a few dozen older Americans who told BI through interviews and a voluntary survey in recent months that losing a loved one affected their finances and retirement plans. Some respondents said losing a spouse, a parent, or a child made them panic and make poor financial decisions. Others said they had to quit working or take lower-stress jobs to cope with the pain.

Read a letter Brattoli wrote to her younger self about what she would have done differently or kept the same. Her story continues below.

Raising a family as a college professor

Brattoli grew up in a middle-class family in Sacramento, California, and was the first in her family to graduate from college. She got a master's degree in English and found work teaching at a community college outside Chicago in 1993, where she also ran its study-abroad program.

She and her husband had three children and invested much of their money in them. She taught extra classes to keep their finances stable and fund vacations.

Brattoli supported her children's musical passions, including financially. Anthony played the tuba and enrolled at Brown University. He won the Brown University Orchestra Concerto Competition and had a concentration in English and Slavic studies. In 2018, he got a job in Prague translating Russian legal documents into English.

"I had this job that allowed me to be flexible during the day, but then so I would run around, take the kids to their appointments," Brattoli said. "And then at night, I was up grading papers until really late."

Grieving and working

While in Prague, Anthony suffered a brain hemorrhage and was in a vegetative state for a month. Brattoli traveled there and stayed with Anthony for three weeks, and they flew him back to the US, where he lived the last days of his life. The university's insurance paid for the flight back, though she regretted not investing in good travel insurance as a backup in case Brown didn't cover it in full.

Brattoli went on leave after Anthony's death but returned to work starting in spring 2019 — including remote teaching before and during the pandemic — to pay her bills.

"I was completely incapable of teaching, and I forced myself to get through it for a time, but I could not function," Brattoli said.

She said because of the grief, she did not prioritize long-term financial planning, adding that she didn't know where to turn for help beyond her therapists or employer. She wishes she would have spoken with a financial advisor or sought retirement resources to make her savings go further.

While winding down her teaching career at 54, she took a job at Costco, first as a seasonal clerk packing e-commerce orders, then in an administrative role handling accounts payable and scheduling truck routes. She was promoted to facilities supervisor at a distribution center, which paid about $65,000 annually. She said that she's still financially stable and that her Costco salary allowed her to somewhat comfortably pay her bills.

Her husband, who is a few years older than her, worked after Anthony's death but lost his job during the pandemic. He also pivoted to Costco, working at a warehouse.

Financial pains

Brattoli contributed to her public-school retirement plan, though she said she and her husband didn't save much. She didn't track how much she put into her retirement accounts and said it was cumbersome to increase her contributions. She wishes she had set aside much more of her earnings earlier so interest would compound on them.

In the years after Anthony's death, Brattoli said her grief and lack of direction led to some financial issues. Because she gave up teaching, she cashed out her state pension early and got paid less than if she continued teaching for more years.

Since she has a public pension, a Social Security provision cuts her benefits from her private-sector work.

"I'm now at a penalty, and that'll be for the rest of my life," Brattoli said. "Even though now I'm working for Costco and I'm putting into Social Security, my Social Security is going to be terrible."

She intends to work for Costco until she's 65, when she expects to have enough for retirement, fearing she won't be physically equipped to work there much later. Costco gives her health insurance, and with her children now financially stable adults, she said she could save more for her future, putting much of her earnings into her 401(k). She said her pension would help keep her afloat after retirement.

"I feel uncertain right now because inflation has messed up my pension already," Brattoli said. "I suffered with that because I took my pension, and then inflation jumped up, and it's not like Social Security where it automatically increases based on how much inflation goes up."

Brattoli said despite the pain of the last few years, the decision to work at Costco was the best choice. Her Costco income and pension brought her to about where she'd be if she still taught full-time, and the role helped her rebuild her confidence.

"It gave me a chance to focus on something completely different than teaching," Brattoli wrote in her letter. "Now, I wear steel-toed shoes. I learned how to drive a forklift. I climb into the backs of semi-trailers and onto the roof of the building."

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• In 2018, at 46, Chris retired and left Chicago for Bangkok.
• He spent two years planning and saving for his move by investing in real estate.
• He enjoys the affordability of living in Bangkok and how easy it is to make friends.

As he soaked in the pool of his Airbnb in Bangkok, Chris wondered, "How can I make this my home permanently?"

It was 2016, and he had spent the past 25 years in the toy industry overseeing product development. His routine was the same: wake up, go to work, come home, play a video game, and sleep. At 44, retirement was weighing on his mind.

"There was nothing else I needed to really do," said Chris, now 52, who asked to be identified only by his first name to protect his privacy. "I mean, could I have worked longer to buy a cooler car? Maybe. Could I have bought a bigger house? Maybe. But nothing like that was really important to me."

At the same time, Chris knew he didn't want to retire in his home state of Illinois. He loved the city but couldn't stand the long and bitter winters. Most of his friends — unlike him — were married with kids. He wanted to challenge himself with a hard reset.

Chris had taken many business trips to Asia and started to love that part of the world. So, he mapped out a plan to save up, quit his job, and then live there full-time.

The first thing he did was tell no one

He didn't want to deal with negative reactions, he said. So, he kept his plan a secret for almost two years.

But behind the scenes, Chris worked feverishly to make his plan a reality.

First, he ramped up his real estate investments. Chris got more involved in the real estate market in 2014 after paying off the mortgage of his first home 17 years early. "When you pay off a house, it's the coolest feeling for a couple of weeks — you don't have a mortgage payment. And then you're like, what do I do?" he recalled.

He decided to invest in more property. By 2018, he had nine properties earning around the same amount as his full-time job.

He also visited Thailand eight times to ensure it was where he wanted to be. He had considered Hong Kong and Japan but eventually decided against them due to the higher cost of living.

"I wouldn't do touristy things. I would sometimes spend days just hanging out at the condo I was renting as if I already lived here," he said.

By September 2018, he had a six-figure safety net in the bank — in case he "didn't survive" and had hired a property manager to look after his properties. With a Thai Elite Visa — a long-term tourist visa that permitted his residency for the next five years, he left frosty Chicago for sunny Thailand.

The first six months were hard

Chris said he was used to being in a job where he had a team and worked on multiple projects.

"It was very strange to be fully retired and not have any responsibilities at a young age," he said. "I definitely, in the beginning, had some panic attacks where I'd wake up at 3 in the morning and be like, 'What did I just do?'" he recalled.

Things improved when he followed a friend's suggestion to explore a site for meeting people with the same interests. Through meetup.com, Chris was able to connect with other expats and make Thai friends. Playing pickleball was a great way to connect with new people, he said.

"Bangkok is such a massive city. It's so easy to walk up to almost anybody and say hello," he said. "I don't do it as much as I used to because I have a lot of friends now. I'm like, I can't handle more friends," he said with a laugh.

Living in Thailand is more affordable

Chris lives in an 882-square-foot two-bedroom apartment in Thonglor, a hip neighborhood in Bangkok with trendy bars and shopping centers. His rent is 62,000 Thai baht, or around $1,785 a month.

Before he left the US, he had set a budget of around $3,000 a month based on three factors: his age, lifestyle, and health. Describing his lifestyle as "semi-luxury," Chris said that he's increased his budget year after year to adjust to his changing circumstances. Now, his budget is at $3,800.

Still, it's almost half of what he spent in Chicago, which was over $6,000 a month.

Chicago is the most expensive place to live in the Midwest. Among 32 Midwestern cities, Chicago has the highest Cost of Living Index score, the Council for Community and Economic Research found last October.

"I get so shocked every time I go home once a year to visit my mom and see how it's gone up even more exponentially over the last couple of years," said Chris, who would spend a few weeks with his 82-year-old mom.

He recalled that his parents were more shocked about his early retirement than his move.

"I think this is important for people that move away from family," he said. "You can't think of it as how many years you have left with somebody. You have to think about it as how many visits you have left with that person."

Thailand is a popular retirement destination

Chris is not the only one who has found a retirement haven in Thailand.

According to the World Bank, the number of foreigners over 50 who received retirement visas to stay in Thailand doubled between 2013 and 2018 to nearly 80,000.

Retirees enjoy the country's slow pace of life and low cost of living.

John Walker, 73, moved from Australia to Chiang Mai, a province in northern Thailand, in 2019. He lives on an annual pension of around $18,000 and saves around 40% of his income. "People from all different countries come here," he told BI. "It's got a huge retirement community."

Similarly, Jeffrey Odgen, 75, decided to retire in Hua Hin, a beach town south of Bangkok. "The people here are very respectful. They respect their elders, whereas you don't get that in other European countries," said Odgen, who is originally from the UK.

For Chris, being able to live any type of lifestyle is his favorite part of living in the city.

"If you want to be a recluse and just hide in your condo all day and get everything delivered, you can do that. If you want to explore the city, the public transportation is amazing," he said. "There's a lot of great culture, and everything is just right at your fingertips."

Although he's been in the city for six years, Chris says it only feels like six minutes.

"It has been the fastest and the best six years of my life living here," said Chris, who has since extended his visa for 20 more years. "I absolutely want to stay as long as I possibly can."

Do you have a story about moving abroad to retire that you want to share? Get in touch with the reporter, Erin: [email protected].