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Insomnia Cookies CEO delivered cookies as a student at 2 a.m. Now he runs a $350 million empire

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College campuses are a breeding ground for innovation—including successes like Facebook, Snapchat, and Gatorade. Another prime example is Insomnia Cookies, which was created at an Ivy League campus house and has since turned into a cult staple for legions of students looking for their late-night sweet treat fix. 

Insomnia Cookies is now a fixture at U.S. colleges, with many of its 350 international stores (and counting) housed on or near university campuses. Delivering warm cookies into the wee hours of the morning, with some locations open until 3 a.m., it’s an easy pick for students coming back from rowdy parties or binge-watching TV past midnight. And its founder and CEO, Seth Berkowitz, truly knows his audience, as he launched his business as a University of Pennsylvania junior back in 2003. 

Berkowitz was an economics major living with eight other college roommates under one roof, which he describes to Fortune as “a bit of a frat house.” Together, they’d often stay up late playing video games or tuning into baseball and football games—with Papa John’s as their go-to snack. But he got sick of his housemates constantly ordering pizzas every night, craving something sweet instead. Then, Berkowitz had a light-bulb moment: There were no late-night dessert delivery options around him. He knew he could fix that.

“I walked into the common house and I was like, ‘Guys, I cannot believe we keep ordering from these over and over again. Let’s get something sweet—how great would that be?’ Well, no one delivers anything sweet,” Berkowitz tells Fortune. “And so it’s like, all right, somebody needs to change this.”

From hand-delivering 89-cent cookies at 2 a.m. to raising angel investments as a college senior

Recognizing a gap in the market, Berkowitz wasted no time getting his hobby off the ground. For the first four weeks, he would only get a maximum of five orders per night. He’d sell each cookie for 89 cents, delivering cookies as late as 2 a.m. to hungry customers around campus. But his home operation finally took off when the school newspaper ran a profile on his cookie-peddling scheme, plastering the story on the front page. That evening, he got 85 orders. 

Courtesy of Insomnia Cookies

“That night was a big spike. It then settled into the 30, 40 delivery range,” Berkowitz recalls. “I was like, ‘Okay, this really does work. If I can scale this up, there’s a business to be had.’”

Fervor over his cookies soon attracted investors before he even graduated college in 2004. The young up-and-coming entrepreneur wanted to take his brand to collegiate locations across the U.S., and the dominos fell. Hype over the late-night dessert chain gained enough traction for Insomnia to spread to campuses all over, including the University of Maryland and the University of Illinois. 

The 44-year-old entrepreneur says those early stages between the years of 2004 and 2008 were incredibly exciting. Insomnia Cookies was growing fast and adding units—but everything took a turn when the Great Recession hit. The business hadn’t reached profitability yet, and on top of their customers being financially strained, it was difficult to raise capital. Berkowitz says his angel investors weren’t sure how the world was going to be after the financial crash, and couldn’t put their money into “hobby investments” like they once did. It was a dark time for Insomnia, but it also pushed Berkowitz to keep the brand’s then-14 locations alive. 

“All of those things forge discipline in the brand. It pushed us to be much more methodical, much more focused,” Berkowitz explains. “I hunkered down, I reduced my team, I took a lot more on my own shoulders…It was all about persistence, perseverance, and just a belief in the opportunity.”

Selling a majority stake to Krisy Kreme for nearly $140 million

Insomnia Cookies has thrived since the bumpy years following the 2008 financial crash—and beloved donut titan Krispy Kreme shelled out millions to acquire the company. In 2018, Krispy Kreme purchased a majority stake in the business, paying around $139.5 million for 74.5% of the company, according to a 2021 SEC filing. Krispy Kreme has since sold off its stake, a transaction that valued Insomnia at $350 million in total enterprise value—roughly double what it was since the acquisition.

Berkowitz was able to turn his college passion project into a household name among college students across the country. It took more than two decades of hard work, navigating economic crises and ownership changes, to build the brand into a dessert-chain staple. But the CEO says 22 years of sustained dedication is what makes the business so successful today. 

“We always [say] Insomnia has played the long game, while everyone else has played the hype game,” Berkowitz says. “Businesses that don’t innovate typically don’t last very long…The question always becomes, ‘Can you keep doing it right? Can you reinvent yourself, remake yourself consistently and persistently?’ It continues to drive us.”

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Co-working provider JustCo CEO sees commonalities with hotels: ‘It’s a hospitality business’

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Kong Wan Sing, the founder and CEO of JustCo, one of Asia’s largest co-working space providers, doesn’t quite think of himself as leading an office company. Instead, he sees parallels with a different property business: Hotels.

“It’s a hospitality business. People come to us not just for the network, but also for the hospitality,” he told Fortune. “You need to serve them. You have to take care of their needs, like serving the customers who are coming to look for them in the office.”

Kong and JustCo are expanding their presence in Asia even as employers and employees continue to fight a battle about flexible work and returning to the office. Globally, corporate giants ranging from Amazon to JPMorgan have called workers back to the office full-time. But employees tout the benefits of working from home and hybrid work, forcing employers and office designers to get creative in how they bring people back. 

The company is also expanding into new markets regionally, including Malaysia and India. In the longer run, they’re also looking to move into countries in North Asia and the Middle East.

“After entering all these markets, we will be truly covering all the key cities in Asia-Pacific,” says Kong. He’s even considering returning to mainland China, after JustCo exited the market in 2022 due to tight social distancing regulations during the COVID pandemic.

JustCo just entered the Vietnam market with a new office along Ho Chi Minh City’s waterfront. The Vietnamese city is the tenth urban market in Asia for JustCo. It’s also a return of sorts for Kong, who was first exposed to the idea of a flexi-office in Ho Chi Minh City several decades ago. 

JustCo’s story

Kong Wan Sing founded JustCo in Singapore in 2011. Following a regional expansion drive in 2015, it now operates 48 offices across Asia-Pacific, including in major cities like Seoul, Bangkok, Taipei, Melbourne, and Sydney. Kong himself hails from a family of entrepreneurs; his parents operate garment factories in nearby Malaysia. “There’s genes inside me to build a business,” he says. 

In the early 2000s, Kong was an employee of Singaporean real estate investment company Mapletree, working out of a flexi-office in Vietnam’s Ho Chi Minh City. (A flexi-office is a modern workspace where employees don’t have assigned desks, but instead choose from various work zones including hot desks, quiet pods, and collaborative areas.)

The experience opened his eyes to the value of flexible workspaces, and he saw a business opportunity in Asia, where such spaces were still few and far between. 

Kong notes that, just three years ago, just under 4% of all offices in Asia-Pacific were flexi-offices. It’s since risen to over 5%, but that’s still half the level seen in more developed markets in Europe and the U.S. Yet JustCo’s CEO says he’s seeing a “surge” in Asia: “The growth is definitely much faster than European or American countries.”

JustCo also leases small offices for businesses to rent. Sixty percent of JustCo’s clients are multinational corporations looking for space for a regional office, Kong said. Companies like Chinese tech giant Tencent and U.S. vaccine maker Moderna use JustCo for their local offices. 

New brands

JustCo has since broadened its offerings to potential renters, launching two new brands: “THE COLLECTIVE” and “the boring office.”

The former is a luxury co-working space, equipped with premium white-glove services like daily breakfasts and aperitif hours, and twice-a-day office cleaning. The first such space was launched in Tokyo in March.

“Japan is a very mature market, and people in Japan—they appreciate luxury stuff,” said Kong, when asked why the country was chosen to debut its premium brand. Kong and his team has since launched THE COLLECTIVE in Bangkok and Taipei; the company will bring the concept to Singapore and India in 2026.

“The boring office” sits on the other end of the spectrum, catering to firms that want a stripped-down solution. “When you go to the boring office, there’s no cleaning [of rooms] every day, only once a week,” Kong says. “And the pantry is a very basic pantry that provides only water—there’s no coffee, nothing.” The first space under that brand was launched in Singapore in July.

These three brands cater to companies’ differing needs, and are priced along a sliding scale. 

The firm’s luxury offices are 20 to 30% more costly than the classic JustCo workspace, while the boring office’s spaces are cheaper by roughly the same amount, Kong explains.



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Creative workers won’t be replaced by AI, they will become ‘directors’ managing AI agents

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AI won’t automate creative jobs—but the way workers do them is about to change fundamentally. That’s according to executives from some of the world’s largest enterprise companies who spoke at the Fortune Brainstorm AI conference in San Francisco earlier this week.

“Most of us are producers today,” Nancy Xu, vice president of AI and Agentforce at Salesforce, told the audience. “Most of what we do is we take some objective and we say, ‘Okay, my goal is now to spend the next eight hours today to figure out how to chase after this customer, or increase my CSAT score, or to close this amount of revenue.”

With AI agents handling more tasks, Xu said that workers will shift “from producers to more directors.” Instead of asking, “How do I accomplish the goal?” they’ll instead focus on, “What are the goals that I want to accomplish, and then how do I delegate those goals to AI?” she said.

Creative and sales professionals are increasingly anxious about AI automation as tools like chatbots and AI image generators have proved to be good at doing many creative tasks in sectors like marketing, customer service, and graphic design. Companies are already deploying AI agents to take on tasks like handling customer questions, generating marketing content, and assisting with sales outreach. 

Pointing to a recent project with electric-vehicle maker Rivian, Elisabeth Zornes, chief customer officer at Autodesk, said that the company’s AI-powered tools enabled Rivian to test designs through digital wind tunnels rather than clay models. “It shaved off about two years of their development cycle,” Zornes said.

As AI takes on some of these lower-level tasks, Zornes said, workers can focus on more creative projects.

“With AI, the floor has been raised, but so has the ceiling,” she added. “We have an opportunity to create more, to be more imaginative.”

The uneven impact of AI

The shift to AI-augmented work may not benefit all workers equally, however.

Salesforce’s Xu said AI’s impact won’t be evenly distributed between high and low performers. “The near-term impact of AI will largely be that we’re going to take the bottom 50 percentile performers inside a role and bring them into the top 50 percentile,” she said. “If you’re in the top 10 percentile, the superstar salespeople, creatives, the impact of AI is actually much less.”

While leaders were keen to emphasize that AI will augment, rather than replace, creative workers, the shift could reshape some traditional career ladders and impact workforce development. If AI agents handle entry-level execution work, companies may need to hire fewer people, and some learning opportunities may disappear for younger workers. 

Ami Palan, senior managing director at Accenture Song, said that to successfully implement AI agents, companies may need to change the way they think about their corporate structure and workforce.

“We can build the most robust technology solution and consider it the Ferrari,” she said. “But if the culture and the organization of people are not enabled in terms of how to use that, that Ferrari is essentially stuck in traffic.”

Read more from Brainstorm AI:

Cursor developed an internal AI help desk that handles 80% of its employees’ support tickets, says the $29 billion startup’s CEO

OpenAI COO Brad Lightcap says ‘code red’ will force the company to focus, as the ChatGPT maker ramps up enterprise push

Amazon robotaxi service Zoox to start charging for rides in 2026, with ‘laser focus’ on transporting people, not deliveries, says cofounder



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Trump says ‘starting’ land strikes over drugs in latest warning

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President Donald Trump said the US would be “starting” land strikes on drug operations in Latin America, though again declined to provide details on when and where the escalation of his military campaign would actually begin, or if countries could still do anything to avert the threatened action.

“We knocked out 96% of the drugs coming in by water, and now we’re starting by land, and by land is a lot easier, and that’s going to start happening,” Trump told reporters Friday in the Oval Office.

The US president for days has been pledging to broaden the effort, which comes after the Pentagon has launched a series of attacks on what it has called drug-smuggling boats in international waters off the coast of South America.

While Trump’s posturing has largely been seen as a pressure campaign against Venezuelan President Nicolás Maduro, he on Friday insisted the land targeting may not only impact Venezuela.

Read more: Trump Says US Eyes Land Strikes Next After Drug Boat Attacks

“It doesn’t necessarily have to be in Venezuela,” he said, adding that “people that are bringing in drugs to our country are targets.” 

Trump has justified the actions in part by framing the fight against drug smuggling as akin to combat operations. He told reporters that if overdose deaths were counted like combat deaths, it would be “like a war that would be unparalleled.”

Striking targets on land would represent a major escalation, and Maduro earlier this week said that if his nation came under foreign attack, the working class should mount a “general insurrectionary strike” and push for “an even more radical revolution.”

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