• Multimillionaire Shark Tank investor Kevin O’Leary looks for three star qualities in the entrepreneurs he goes into business with: those who have a “founder’s mindset,” a balanced talking-to-listening ratio, and executional prowess. From working with the likes of late Apple cofounder Steve Jobs and multimillion-dollar entrepreneurs to being an investor on his hit-TV show, he’s picked up a few patterns of the most successful people. 

Multimillionaire entrepreneur Kevin O’Leary knows a thing or two about picking the right people and ideas to invest in. Having worked with greats like Steve Jobs, not to mention his success on Shark Tank backing businesses generating millions, he’s picked up on a few key qualities in great founders. 

O’Leary looks for three qualities in the people he chooses to do business with. The 71-year-old investor tells Fortune the most critical trait is having “founder’s mindset”: adopting a frame of mind that prioritizes “signal,” or what has to get done in the next 18 hours, while drowning out the “noise” of everyday life and complications. He witnessed this demeanor while working with Jobs, when Apple was partnering with O’Leary’s $4.2 billion software company SoftKey Software Products. He requires that the founders he invests in have that same leadership ethos—even if it’s a quality that’s hard to come by. 

“The ability to see all the noise coming at you and filter it out, and focus on the three to five things you’re going to get done, that’s a remarkable attribute,” O’Leary tells Fortune. “You find that in 30% of the people. Then you want to back those people, because if they’re not successful in their first mandate, they’re going to figure it out. That attribute is very important.”

When it comes to the signal versus the noise, he currently operates on a 80:20 balance, just like Jobs did while running Apple, and looks for entrepreneurs who can keep their eye on the ball.

O’Leary admits that he didn’t always have the right ratio in embodying the founder’s mindset—but now has achieved it, and looks for it in others.

“You have to decide everyday, every 18 hours, what three to five things you have to get done,” O’Leary says. “It’s not the big vision. It’s what you have to get done in the next 18 hours that matters.”

The two other traits a founder needs to have O’Leary’s backing

O’Leary has heard hundreds—if not thousands—of entrepreneurs plead their business case while starring on Shark Tank. Thanks to his intuition from decades in the game, he’s worked alongside and invested in a lot of winners.

In 2014, O’Leary put $150,000 down for 80% of licensing profits of small photo-book subscription service Groovebook, which was later bought by Shutterfly for $14.5 million, making it one of the show’s biggest acquisitions.

He also had luck with sustainable cleaning-products business Blueland, investing $270,000 for 3% equity and $0.50 per unit royalty until principal was recouped. By 2022, Blueland made over $100 million in lifetime sales and profitability, with its products now flying off the shelves of Target and Whole Foods every 10 seconds.

It’s clear the serial investor has developed a keen eye for what will work well. In addition to the “founder’s mindset,” the serial investor also emphasizes the importance of having a balanced listening-to-talking ratio and strong executional skills, which he says is “impossible to find.” 

He says he didn’t always get the talking-to-listening balance right. Wall Street and Silicon Valley executives may think they should be the loudest and most outspoken people in the room—but taking a backseat and giving others the floor is important, too. Not enough listening and too much talking may stifle great business ideas that get drowned out.

“Reverse the ratio of talking and listening. Most people love to hear themselves talk—I was guilty of that for years, and I’ve reversed it,” O’Leary says. “I listen two thirds of the time, and I talk one third of the time. That’s my new ratio, and it’s much more powerful.”

Lastly, the baby boomer investor looks for unparalleled executional skills. Coming up with the next billion-dollar business venture is one thing, but getting it off the ground is another.

O’Leary looks for founders and teams that can get the job done—even if it takes more than one try. Being an excellent executor doesn’t always mean hitting a home run your first time at bat. Sometimes, O’Leary says, investors and entrepreneurs need a little karma and luck. 

“Great ideas are dime a dozen—executional skills are impossible to find,” O’Leary continues. “I’ve invested in lots of teams over the years that screw up their first deal, they go to zero, and then I invest again, and I get a huge hit, because I know they’re good.

“I’m working on a deal right now with a team that I just finished a great execution with, and hopefully will be good on the second one. I like to work with people that I know have proven executional skills.”

This story was originally featured on Fortune.com

© Christopher Willard / Contributor / Getty Images

• Gen Z’s career plan to go to college, land a white-collar job, and achieve financial security has been dashed. After just a few years in the corporate world, they’re already fed up with the nine-to-five lifestyle, with a majority of young professionals finding traditional gigs “soul-sucking.” They can take a page from the playbook of millennial and Gen X leaders helming Too Good to Go, Sweet Loren’s, Hella Cocktail Co., and Wellhub who also left corporate America. 

Gen Z are watching their career plans go up in flames as entry-level jobs are being snubbed by AI, and white-collar salaries aren’t keeping pace with inflation. So they’re ditching their nine-to-fives to become their own bosses—and they aren’t the only ones.

White-collar Gen Z don’t have to look far to find success stories of people quitting their nine-to-fives to do something they actually liked. 

From Too Good to Go’s Mette Lykke to Sweet Loren’s Loren Castle, these millennial and Gen X entrepreneurs ditched corporate America and haven’t looked back since—and now they’re running a trio of self-built getaways, leading a $120 million cookie dough brand, and spearheading sustainable food apps. 

Just like Gen Z, these entrepreneurs hated the idea of working all day to make their bosses money. Plus, the work they were doing was simply unfulfilling—and they know life is too short to stick with careers they weren’t happy in.

Sweet Loren’s Loren Castle

Courtesy of Sweet Loren’s

Sweet Loren’s CEO Loren Castle now leads a $120 million cookie dough brand stocking the refrigerated aisles of Target, Whole Foods, and Costco. But when she was fresh out of college and grappling with a cancer diagnosis, she tried her hand at a boutique PR firm, also juggling other restaurant-industry jobs. Ultimately she was unhappy working for someone else, and wanted to make the most out of a scary situation recovering from illness—so she quit her “real” job, and launched her own healthy sweets company. 

“Life is short. I don’t want regrets. I was so keenly aware of my feelings. If I wasn’t in love with something, it was really hard to make myself do it,” Castle told Fortune. “It got to that point of, ‘I don’t like my boss, I don’t want to be making him money.’”

Dunlap Hollow’s Bryant Gingerich 

Courtesy of Bryant and Amy Gingerich

Entrepreneur Bryant Gingerich was also uninspired in his engineering job, but quickly unearthed his true passion after discovering a swath of wooded land for sale. The millennial purchased the property with his wife Amy, and began building short-term rentals that are now part of his Dunlap Hollow business. 

In the middle of reeling in success from his three home rentals—which raked in over $700,000 in 2024, with Gingerich taking home over $350,000 in net profits—he was finally able to ditch his engineering role. 

“I don’t think I ever want a 9-to-5 again. I honestly haven’t even missed it one time,” Gingerich told Fortune. “I love every bit of what we’re doing here. I love that I get to design things and work with my hands, and not be sitting at a desk all the time. Working on our property in beautiful nature, and that’s just really life-giving for me.”

Hella Cocktail Co’s Jomaree Pinkard

Courtesy of Hella Cocktail Co.

Gen X entrepreneur Jomaree Pinkard had all the makings of a successful corporate worker. He held an esteemed Wharton degree, and had worked at $120 billion professional services firm Marsh & McLennan. But in his 30s, working as a consultant for the NFL, he started to pull away from his nine-to-five path to pursue his hobby making canned beverages and cocktail bitters.

After three to four years of scaling up his passion project, Hella Cocktail Co., with his two best friends and cofounders, he officially quit his NFL job to run his successful business full-time. The CEO was even tapped by $64 billion alcohol giant Diageo for his expertise—and hasn’t looked back on leaving his old corporate career since. 

Wellhub’s Cesar Carvalho

Courtesy of Wellhub

Cesar Carvalho, the chief executive of $2.4 billion corporate wellness platform Wellhub, once had a budding corporate career. The millennial executive once held positions at consulting giant McKinsey & Co. and marketing research firm AC Nielson, even enrolling in Harvard’s prestigious business school—but he dropped out of the university, and took a complete career 180. 

Carvalho left corporate America in pursuit of making it better: by bringing calm and exercise to white-collar workers. Wellhub now serves 26,000 employers across 13 countries, providing gyms, studios, and wellness classes to more than 20 million corporate workers. 

Too Good to Go’s Mette Lykke

Courtesy of Too Good To Go

Too Good to Go’s CEO, Mette Lykke, also left McKinsey with her coworkers without much of a plan. The consultant-turned-executive had the itch to “quit and build something,” so after quitting her job without a coherent business idea, sat down and created a list of 10 start-up ideas. Lykke and her peers opted to launch a fitness community app called Endomondo—which was sold to Under Armour for $85 million in 2015. That was the start of her chapter as a serial entrepreneur, later scaling her sustainable food app Too Good to Go to a massive success. 

“A lot of aspiring entrepreneurs are just sitting there in their corporate jobs waiting for that lightning moment when they have the great idea,” Lykke told Fortune. But she added a warning: “It’s not going to land in your lap, you just decide to go for it or you don’t. Once you decide to go for it, you will come up with something because you have to.”

Why Gen Z are already over their new corporate gigs

Just a few years into working, about 43% of American Gen Zers say they have no desire to work a traditional job, and 60% find nine-to-five roles “soul sucking,” according to a 2024 report from Credit Karma. This comes as 36% of the young professionals struggle to find a corporate gig, with some job-seekers sending out over 1,700 applications and searching for over a year with no luck. 

Even Gen Zers who could snag a role, 65% say they’re unsatisfied because they’re not paid enough, and 61% think their pay hasn’t kept pace with the cost of living. And it’s weighing heavily on their psyche—nearly half say their jobs have had a negative impact on their mental health. Plus, by working for “the man,” they have less control over their schedules. About 41% say they’re unhappy with their gigs because it leaves them with no time to do anything else. 

There are other underlying reasons why young people are so against the nine-to-five career pathway—and a part of it may come from observing those around them. Nearly half, 47%, of Gen Z say watching how obsessed older generations are with work has made them rethink their career paths, according to the report. And they’re also taking inspiration from their peers on TikTok and Instagram. Around 26% of Gen Z say social media posts have motivated them to quit their corporate jobs, and 39% identify as part of the FIRE movement, dead-set on retiring early while financially dependent.

This story was originally featured on Fortune.com

© bojanstory / Getty Images

• Gen Z watched their peers get fired for dressing inappropriately for the office. Now, they’re too scared to dress themselves, even reaching out to managers for guidance. The confusion is also causing stress, as the young generation and millennials are almost three times as likely to have outfit anxiety compared to their boomer coworkers. Many are even turning to their boss for fashion advice, but experts tell Fortune they’d be better off silently taking cues by copying their looks.

After years of wearing pandemic-era tracksuits and a nice top for Zoom meetings, many employees are in the dark about what’s appropriate to wear now that they’re back in an office. While all generations are lost, Gen Z is having the hardest time, with many even turning to their managers for styling tips.

About 78% of workers are seeking guidance on what to wear at work, according to recent data from workplace solutions company IWG. But the youngest cohort of employees needs the most help, with 94% of Gen Z looking for advice on their work outfits, compared to 84% of millennials, 70% of Gen Xers, and 61% of baby boomers. Much of Gen Z’s confusion may chalk up to simply being the newest in the office, with many having started their careers from their couch.

“It’s understandable that the generation with the least working experience will have the most questions about what to wear and what is appropriate in the workplace,” Diana Tsui, a stylist and creative consultant partnering with IWG, tells Fortune. “There has been a fundamental shift in the way in which employees of all generations approach their workwear attire.”

But with over half of employees in each generation looking for workplace fashion tips, the changing rules have left many unsure of what’s appropriate. The lack of clarity is so bad it’s stressing people out—staffers said they experience anxiety about what to wear to the office seven times a month. 

Gen Z and millennials are nearly three times as likely as baby boomers to worry about dressing properly, so they’re turning to their superiors for guidance. About 30% of Gen Z seek guidance from their manager, compared to 14% of Gen X and 10% of boomers. Instead of outright asking their boss what to wear, they could take Tsui’s advice of taking silent cues by copying their looks.

How Gen Z should dress for the office: take inspiration from higher-ups and show restraint

Gen Z has been popularizing new fashion trends at the workplace, like the “office siren” look: dressing 1990s-corporate while “pushing the boundaries of what’s considered acceptable,” the report notes. It’s a twist on power-dressing, but certain elements—like plunging necklines and short skirts—could land them in a meeting with HR. Data shows that already, many Gen Zers have been fired for dressing inappropriately, only adding to their anxiety.

Luckily, there are a few surefire ways that Gen Z can avoid the early-morning anxiety of having to pick out an appropriate outfit for the office. 

“Workwear is never going back to its suit-and-tie days, although that can be fun to dabble in,” Tsui advises. “Take a cue from your industry and see how their prevailing dress codes enmesh with your own sensibilities.”

Tsui has three major tips for young staffers to stay in line with company dress codes and avoid getting sacked for their outfit: 

1. Take inspiration from your superiors: Take a look around the office or check how older coworkers are showing up in Zoom calls. She notes that young workers don’t have to copy their higher-ups, but rather get a vibe-check on the dressing environment.  
2. Express yourself, with restraint: If it’s a more conservative environment, playing with proportions can be a fun way to spice up drab corporate attire. A chunky shoe or eccentric pair of earrings can go a long way in adding flair to an outfit.
3. Don’t show too much skin: Wearing clothes that are too small and show too much skin is “usually still frowned upon,” so try to avoid anything too revealing.

Why nobody knows how to dress for work anymore

Gen Z isn’t the only generation of workers torn on what’s acceptable to wear to the office anymore. Experts Fortune has spoken with all contend that the COVID-19 pandemic was a major turning-point for workplace attire. Now, employees are back in the office, and they don’t know how to give up their stretchy pants. Tsui says it’s on employers to navigate the new world of work attire, and share clear policies with their staffers to avoid any unnecessary stress. 

“This shift away from traditional norms toward more flexible policies highlights the need for modern guidance,” she explains. “As companies adapt to hybrid models and multi-generational teams, employees are increasingly seeking clarity on how to balance self-expression with professionalism in evolving work environments.”

With four generations in the office—Gen Z, millennials, Gen X, and baby boomers—it’s natural that there’s going to be huge divides in terms of style. 

But HR experts agree that a few shifts are here to stay for everyone: sneakers are in, ties and heels are largely out, and you still probably shouldn’t wear shorts. 

Sometimes, casual and comfortable styles can blur the lines of what’s proper for the office—but Tsui says if styled properly, employees can make it work. 

Young staffers can also better curb their outfit stress by adopting a “work uniform.” Gen Z and millennials already lead the way in having a standard style, with 59% having a uniform, compared to 53% of baby boomers, the IWG report notes. It’s a trend among younger generations that gives them a sense of control over their careers—and takes away the concern of picking out a new outfit everyday that may or may not be appropriate for the job.

This story was originally featured on Fortune.com

© Tara Moore / Getty Images

• $61.5 billion tech giant Anthropic barred job applicants from using AI tools in the hiring process in May. Just months later, it has changed its mind on the policy—but unemployed Gen Zers (or any other generation for that matter) should watch out for various other guidelines still in place.

Hiring has become an all-out AI war with managers juggling thousands of fake applications from North Korea, meanwhile, job-seekers are grappling with automated interviewers. AI giant Anthropic even got ahead of the curve by (ironically) barring candidates from using chatbots and assistants to prepare for their interview in May—but it’s just backtracked on the ban. 

The $61.5 billion technology company alerted Fortune to its recently updated policies. Job seekers can now refine their resumes, cover letters, and applications with AI.

But there’s a catch: They’re still barred from using it during most assessments and while they’re sitting in the interview.

“At Anthropic, we use Claude every day, so we’re looking for candidates who excel at collaborating with AI,” the company wrote in its candidate AI guidelines. “Where it makes sense, we invite you to use Claude to show us more of you: your unique perspective, skills, and experiences.”

The company had previously reasoned that by banning the tools, hiring managers could have a better sense of applicants’ “personal interest” and their “non-AI-assisted communication skills.” 

However, Anthropic may be changing its guidelines, as in reality, it’s hard to police, gets candidates using their product, and levels the playing field—since the company uses Claude to create job descriptions, improve interview questions, run candidate communications, and more, it’s only fair that candidates can access such tools too.

“This isn’t revolutionary, but it’s intentional,” Jimmy Gould, head of talent for Anthropic, wrote on LinkedIn. “We recognize that deploying AI in hiring requires careful consideration around fairness and bias, which is why we’re experimenting, testing, and being transparent about our approach.”

The changes to AI in hiring: when Anthropic applicants can use the tech

Anthropic has a few rules for applicants using Claude in the hiring process: they must use the tool thoughtfully, be themselves, and be transparent. Here is where they can and can’t use AI in Anthropic’s hiring process, as the company says, to “use Claude to show us more of you”:

• When applying: Applicants should write their own first drafts of resumes, cover letters, and application questions. Then they can use Claude to refine their materials, to “polish how [they] communicate about [their] work.”
• During take-home assessments: Candidates can use Claude when instructed to, but otherwise cannot use the tools. 
• Preparing for interviews: Claude can be used for applicants to research Anthropic, practice their answers, and prepare questions for the interviewer.
• During live interviews: No AI assistance is allowed in this part of the process unless told otherwise.

These updated guidelines allow more flexibility after the tools were barred from the process altogether—but candidates shouldn’t get too comfortable with the current process as it could change again. Anthropic revealed it plans to regularly review and update the policy “to reflect evolving AI capabilities.” 

How AI is changing the hiring process

Anthropic isn’t the only company that has been wary of job seekers using the tech to get a leg-up. Goldman Sachs similarly issued a warning to students interested in its private investing academy in EMEA, reminding them that the bank “prohibits the use of any external sources, including ChatGPT or Google search engine, during the interview process.”

But the hiring process may already be changed forever, as both recruiters and job-seekers are leveraging the tools in the talent war. Companies like KPMG, Eventbrite, and Progressive are using the technology to sort through thousands of applications, speed up the process, and make better hiring decisions. It’s proved to be an incredibly helpful tool as managers have to comb through piles of documents.

Candidates are increasingly leaning on AI in response to the white-collar job hunt becoming so dire. In 2024, nearly half of job-seekers used generative AI to “build, update, or improve” their resumes, according to a report from Canva. 

OpenAI’s ChatGPT seems to be a particularly popular tool, with around 57% of applicants using the chatbot in their job applications, according to a study from consulting firm Neurosight data. And in 2023, around 73% of Americans said they would consider using AI tools in 2024 to help them embellish or lie on their resume, according to a report from StandOut CV. 

As some job-seekers apply to jobs for over a year, sending out thousands of applications, AI has become integral in keeping pace and landing a gig. 

This story was originally featured on Fortune.com

© Kimberly White / Stringer / Getty Images

• Cardinal Health’s CEO says “ruthless prioritization” was needed to turn around the Fortune 500 company whose earnings plummeted $300 million just three years ago. The Gen X chief executive, Jason Hollar, slashed business segments, slimmed down the company and didn’t shy away from ruffling feathers with his new reports. But instead of revolting, he reveals they actually embraced the changes: “People want to win.”

Cardinal Health is one of the largest healthcare giants in America, supplying medical products and data solutions for over 90% of U.S. hospitals. But just a few years ago, its operating earnings plummeted $300 million as some segments struggled. When Jason Hollar took over as CEO of the Fortune 500 company in late 2022, the business turnaround required some serious tough love. 

“This concept of relentless simplification and ruthless prioritization was the cornerstone of the change management and the strategy,” Hollar tells Fortune. 

“And I use the word ruthless for a very particular reason, to put a little bit of an edge to it, because I didn’t want people just to reprioritize everything they’re doing. I wanted them to stop doing certain things.”

Before Hollar took the reins, certain segments were costing the $38 billion health care company hundreds of millions of dollars each year. Cardinal Health’s non-GAAP operating earnings fell 12% from $2.3 billion in 2021 to $2 billion in 2022, while non-GAAP net earnings plummeted 13% from $1.6 billion to $1.4 billion in the same time frame. So on his first day as chief executive, Hollar laid out a cutthroat game plan to bring Cardinal Health back to its former glory, including slashing business segments and slimming down the company. And so far, it’s worked—the business’ operating earnings for Q3 of the 2025 fiscal year hit $730 million.

Usually ruffling feathers is a major concern of incoming chiefs. But perhaps surprisingly, Hollar says that Cardinal Health’s staff weren’t just on board—they were itching for an overhaul.

“[Cardinal Health] is a great place to work. But [employees] were getting frustrated as well that we weren’t succeeding,” Hollar says. “It’s great to be with a great group of people, but people want to win, and we weren’t winning as much as we could have.”

Hollar’s first days in office: slashing segments and halting M&A

It’s no easy feat to turn around a heritage company like Cardinal Health that’s been operating for nearly 55 years. But Hollar’s “ruthless” approach was the juice the healthcare business needed to get back on track. 

The 52-year-old executive first joined the Fortune 500 business as CFO in the thick of COVID, when the business was reeling from uncertainty around those pandemic-era changes and product liabilities like opioids. The company had a large balance sheet restructuring, and some recent acquisitions from prior leadership were driving operational challenges.

Two years later as CEO, he had the extensive knowledge base to turn things around quickly—so he exited product lines, pulled Cardinal Health out of a “significant number” of countries, and sold off its non-healthcare portfolio. 

“There were a lot of changes done in a pretty short period of time,” Hollar explains. “I saw that some poor decisions on capital deployment was a primary driver of some of those operating challenges. So I believed if we did fewer things, [if] we simplified the operations in the organization, and then took those resources and reprioritized it to the faster-growing parts of the industry in the business, that we could be a lot more successful.”

Cardinal Health’s Medical segment, which manufactures surgical and laboratory products, also needed a complete revamp—it had lost $16 million in just one quarter, prior to Hollar stepping in. The CEO also increased its capital expenditures and selling, general, and administrative expenses (S&GA) in speciality growth initiatives. Simultaneously, Hollar streamlined Cardinal Health’s focus. During his first 18 months, he didn’t pursue any significant M&A, and instead put all his energy into existing products and clients. The business later acquired Specialty Networks in 2024 for $1.2 billion.

“It was an absolute pivot from where we were. We were trying to grow in so many different ways. We were not doing any of them really well,” Hollar says. “Our service levels improved dramatically, our productivity, our efficiency, and even things like safety and quality are at much better levels. My philosophy is that you can’t just do some of the processes better some of the time—all [are] deep-rooted success across the board…or you don’t do any of them well.”

Not changing the culture, but finally putting in the elbow grease so all workers ‘win’

It wasn’t just the more technical side of Cardinal Health that needed a facelift—Hollar says employees were happy to work there, but were a bit dejected by recent losses. To build up morale and finally get workers on the “winning” side of things, Hollar delivered an honest truth. 

“I told the team, ‘There’s one value we don’t show up with every single day, and that’s accountability. That’s the one we have to work on,’” Hollar says. “We’re not going to change the values, we’re not going to change our mission and vision. What we need to do is we actually just need to live up to them.”

Hollar says he knew exactly what leadership shake-up would help him achieve his mission. He separated three of his eight direct reports, eliminating two of the roles entirely. By restructuring the business, he was able to add another three direct reports. Hollar was changing up his personnel, and moving fast—which he says proved to employees that his dedication was stronger than just platitudes. 

“[I] demonstrated to the team that these are a lot more than happy words, these are our actual actions, that we’re going to put resources behind the strategy that I laid out,” Hollar says. “Ultimately that led to $5 billion of M&A that we’ve done over just the last 18 months.”

This story was originally featured on Fortune.com

© Courtesy of Cardinal Health