• AI is replacing human hiring managers in job interviews—and candidates are pushing back. Despite being unemployed, professionals told Fortune they’re refusing to take calls with bots, calling it an “added indignity” and a red flag for company culture. Still, stretched-thin HR teams say it’s the only way to handle thousands of applicants.

The next time you get buttoned-up and sit down for a long-awaited job interview, you might not find a human on the other end of the call. Instead, job-hunters are now joining Zoom meetings only to be greeted by AI interviewers. Candidates tell Fortune they’re either confused, intrigued, or straight-up dejected when the robotic, faceless bots join the calls. 

“Looking for a job right now is so demoralizing and soul-sucking, that to submit yourself to that added indignity is just a step too far,” Debra Borchardt, a seasoned writer and editor who has been on the job-hunt for three months, tells Fortune. “Within minutes, I was like, ‘I don’t like this. This is awful.’ It started out normal…Then it went into the actual process of the interview, and that’s when it got a little weird.”

AI interviewers are only the newest change to the hiring process that has been upended by the advanced technology. With HR teams dwindling and hiring managers tasked to review thousands of applicants for a single role, they’re optimizing their jobs by using AI to filter top applicants, schedule candidate interviews, and automate correspondence about next steps in the process. AI interviewers may be a god-send for middle-managers, but job-seekers see them as only another hurdle in the intense hunt for work. 

The experience for some job-hunters has been so poor that they’re swearing off interviews conducted by AI altogether. Candidates tell Fortune that AI interviewers make them feel unappreciated to the point where they’d rather skip out on potential job opportunities, reasoning the company’s culture can’t be great if human bosses won’t make the time to interview them. But HR experts argue the opposite; since AI interviewers can help hiring managers save time in first-round calls, the humans have more time to have more meaningful conversations with applicants down the line. 

Job-seekers and HR are starkly divided on how they feel about the tech, but one thing is fact—AI interviewers aren’t going anywhere. 

“The truth is, if you want a job, you’re gonna go through this thing,” Adam Jackson, CEO and founder of Braintrust, a company that distributes AI interviewers, tells Fortune. “If there were a large portion of the job-seeking community that were wholesale rejecting this, our clients wouldn’t find the tool useful… This thing would be chronically underperforming for our clients. And we’re just not seeing that—we’re seeing the opposite.”

Job-seekers are dodging AI interviewers 

Social media has been exploding with job-seekers detailing their AI interviewer experiences: describing bots hallucinating and repeating questions on end, calling the robotic conversations awkward, or saying it’s less nerve-wracking than talking to a human. Despite how much hiring managers love AI interviewers, job-seekers aren’t sold on the idea just yet. 

Allen Rausch, a 56-year-old technical writer who has worked at Amazon and Electronic Arts, has been on the job hunt for two months since getting laid off from his previous role at InvestCloud. In looking for new opportunities, he was “startled” to run into AI interviewers for the first time—let alone on three occasions for separate jobs. All of the meetings would last up to 25 minutes, and featured woman-like cartoons with female voices. It asked basic career questions, running through his resume and details about the job opening, but couldn’t answer any of his questions on the company or culture.

Rausch says he’s only open to doing more AI interviews if they don’t test his writing skills, and if human connection is guaranteed at some point later in the process.

“Given the percentage of responses that I’m getting to just basic applications, I think a lot of AI interviews are wasting my time,” he tells Fortune. “I would probably want some sort of a guarantee that, ‘Hey, we’re doing this just to gather initial information, and we are going to interview you with a human being [later].’”

While Rausch withstood multiple AI interviews, Borchardt couldn’t even sit through a single one. The 64-year-old editorial professional says things went downhill when the robotic interviewer simply ran through her resume, asking her to repeat all of her work experiences at each company listed. The call was impersonal, irritating, and to Borchardt, quite lazy. She ended the interview in less than 10 minutes. 

“After about the third question, I was like, ‘I’m done.’ I just clicked exit,” she says. “I’m not going to sit here for 30 minutes and talk to a machine… I don’t want to work for a company if the HR person can’t even spend the time to talk to me.”

Alex Cobb, a professional now working at U.K. energy company Murphy Group, also encountered an AI interviewer several months ago searching for a new role. While he’s sympathetic towards how many applications HR has to sift through, he finds AI interviewers to be “weird” and ultimately ineffective in fully assessing human applicants. The experience put a bad taste in his mouth, to the point where Cobb won’t pursue any AI-proctored interviews in the foreseeable future. 

“If I know from looking at company reviews or the hiring process that I will be using AI interviewing, I will just not waste my time, because I feel like it’s a cost-saving exercise more than anything,” Cobb tells Fortune. “It makes me feel like they don’t value my learning and development. It makes me question the culture of the company—are they going to cut jobs in the future because they’ve learned robots can already recruit people? What else will they outsource that to do?”

AI interviewers are a god-send for squeezed hiring managers 

While many job-seekers are backing away from taking AI interviews, hiring managers are accepting the technology with open arms. A large part of it comes from necessity. 

“They’re becoming more common in early-stage screening because they can streamline high-volume hiring,” Priya Rathod, workplace trends editor at Indeed, tells Fortune. “You’re seeing them all over. But for high-volume hiring like customer service or retail or entry-level tech roles, we’re just seeing this more and more… It’s doing that first-stage work that a lot of employers need in order to be more efficient and save time.”

It should be noted that not all AI interviewers are created equal—there’s a wide range of AI interviewers entering the market. Job-seekers who spoke with Fortune described monotonous, robotic-voiced bots with pictures of strange feminized avatars. But some AI interviewers, like the one created by Braintrust, distribute a faceless bot with a more natural sounding voice. Its CEO says applicants using the tech are overall happy with their experience—and its hiring manager clientele are enthusiastic, too. 

However, Jackson admits AI interviewers still have their limitations, despite how revolutionary they are for HR teams.

“It does 100 interviews, and it’s going to hand back the best 10 to the hiring manager, and then the human takes over,” he says. “AI is good at objective skill assessment—I would say even better than humans. But [when it comes to] cultural fit, I wouldn’t even try to have AI do that.”

This story was originally featured on Fortune.com

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• Workers making over $100,000 no longer consider themselves “rolling in it”—more than half of six-figure earners no longer feel financially successful. Those with top salaries are shopping at discount grocery stores, and cutting back on dining, clothes, and travel as they try and make ends meet. They’re even stalling major life plans—like renovating their homes, and throwing their weddings. 

Being a six-figure earner once felt like an exclusive club, with the promise of a lavish life—but now those making over $100,000 are feeling the pinch. So much so that they’re even buying their groceries at dollar stores and ditching takeouts.

More than half (58%) of six-figure earners no longer feel financially successful, according to a recent report from Clarify Capital. 

Six-figure earners aren’t choosing to fly economy over first-class—they’re looking for better deals when it comes to the essentials. More than seven in 10 of these high earners are now being forced to shop at discount grocery chains to save cash. 

Around 74% also say they’re cutting back on dining out, 54% are skimping out on entertainment, 51% are getting thrifty with buying clothes, 49% are scaling back their subscriptions, and 49% are spending less on travel. 

However, they’re not ashamed of their new thrifty ways, with 62% of six-figure earners proudly claiming they aren’t embarrassed to admit they’re cutting back. 

“In today’s economy, income alone doesn’t guarantee financial peace of mind,” the report says. “High earners are feeling squeezed by inflation, stressed by social pressure, and more mindful about what it really means to be well-off.” 

“As spending habits shift and priorities change, one thing is clear: real wealth is about security, not just status.”

The wealthy are cutting back on major life purchases too

Once the epitome of “making it” in America, workers earning six figures are now in the same boat as their less wealthy peers. 

And beyond the day-to-day expenses, those considered to be “rich” are also delaying major life purchases. About 47% are setting back their dream vacations and travel, 31% are stalling on home renovations, and 26% are delaying buying or leasing a new car.

Perhaps unsurprisingly, the tough housing market has forced many to rethink their American dream timelines, as 17% are pushing back buying a new home—and 6% of six-figure earners are even delaying getting married. 

Essentially, the rising cost of living crisis has forced people in all tax brackets to watch their spending, causing anxiety. About 85% of six-figure workers say they feel stressed and anxious due to increased living costs—and it’s even worse for women. Around 88% of top-earning women feel worried about keeping their checkbooks balanced, compared to 81% of men. 

The new upper-class: making more than $200,000

It’s no surprise that six-figure earners are pinching pennies when it comes to daily essentials—after all, more than half of Americans making over $100,000 annually lived paycheck to paycheck in 2022, 7% more than the previous year, according to a 2023 report. The cost-of-living crisis has pushed the needle of wealth to a new high.

In some parts of the U.S., making around $200,000 isn’t even considered to be “rolling in it.” A household making $199,000 a year in Massachusetts and New Jersey would still be considered middle-class, according to a 2025 analysis of 2023 U.S. Census Bureau data. And in every single state in America, a $100,000 salary is no longer enough to be considered to be upper-class. 

There are several reasons why more six-figure earners are struggling to make ends meet. Some employees have been hit with wage deflation, and the prospect of switching jobs for better pay has been upended. Employees who stayed in their current roles received a 4.6% wage bump in January and February, while those who switched jobs received only a marginally higher increase of 4.8%, according to 2025 data from the Atlanta Fed. 

Also, inflation has increased living expenses across the board. People may assume a middle-class lifestyle could at least keep up with the basics, but 65% of those households say their incomes were falling behind the cost of living, according to a 2024 study from Primerica.

This story was originally featured on Fortune.com

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• Tripadvisor’s former CEO, Steve Kaufer, said he’s been ghosted on LinkedIn routinely since stepping down from the role three years ago. “Getting ghosted or shut out after leaving a position can happen, and even high-level leaders aren’t immune to it,” a career expert tells Fortune. Workers and hiring managers have also been leaving each other on read, but there are a few tricks to get a ghoster’s attention—or make even stronger connections who will actually message back. 

People aren’t only getting ghosted on dating apps—workers, hiring managers, and even CEOs are being left on read in their professional lives. After Tripadvisor’s former chief executive, Steve Kaufer, stepped down from the top job three years ago, he’s been on the receiving end of radio silence. 

“I laugh at it sometimes when I reach out to someone on LinkedIn and I get ghosted,” Kaufer recently admitted on the Grit podcast. “And I’m like, ‘Wow, that didn’t used to happen to me. But okay, get used to your new life.’”

Kaufer said he’s unbothered by people not responding to his messages. He explained that he kept a pretty low profile as Tripadvisor’s CEO, preferring to be in the thick of business problems and operations, only wanting to do speaking gigs when the publicity would help the company. 

But while Kaufer seems fine with slowly retreating from the limelight—even to the point of getting ignored by his own former peers on LinkedIn—job-seekers and managers are getting fed up with people not responding to them.

A career expert tells Fortune that there are a few common reasons why professionals get ghosted, and shares steps on how to deal with the silent rejection. The truth is ghosting isn’t always personal—and there’s no harm in following up, strengthening other industry connections, and tailoring professional materials to get visibility. Ghosting may even be a “blessing in disguise.”

“Getting ghosted or shut out after leaving a position can happen, and even high-level leaders aren’t immune to it,” Jasmine Escalera, career expert for LiveCareer, tells Fortune. “Always remember that rejection or silence is just part of the process, not a representation of how awesome you are as a candidate.”

CEOs aren’t the only ones getting ghosted

Tripadvisor’s former CEO being left on read is a high-profile example of a very common professional habit that’s hurting workers and employers alike.

The number of job candidate interview reviews on Glassdoor mentioning ghosting more than doubled, climbing 112%, between 2020 and 2023, according to the platform’s data. And hiring managers are even fessing up to doing it—about 69% of HR professionals admit to frequently closing a job search and cutting communication with candidates, according to recent data from Resume Builder and LiveCareer. Then there is the issue of “ghost jobs”—fake job listings that employers put up to feign company growth. Three in five job candidates say they’ve encountered one of these false postings, never hearing back from employers on the opportunity. 

But despite applicants describing the tiring hiring process as “frustrating,” “inequitable,” and “poor,” being ghosted may actually not be the worst thing in the world. 

“Being ghosted can actually be a blessing in disguise. Just like in dating, if someone disappears without a word, they’re simply not the right match,” Escalera says. 

“The same goes for companies, hiring teams, or recruiters. If they’re not communicating, it could very well be a sign that they’re not the environment where your skills and contributions will be truly valued.”

In response to ghost jobs, hiring managers’ radio silence, and exhausting hiring processes, job-seekers are turning the tables on their potential bosses. About 75% of workers say they’ve ignored a prospective employer in the past year, according to 2025 data from Indeed. And Gen Z are the worst offenders—about 93% have admitted that they’ve skipped out on an interview. 

What workers should do when they’re getting ghosted 

Job-seekers may feel powerless when a connection or hiring manager has ghosted them—but career expert Escalera suggests a few ways workers can make the most of it.

1. Build up a reputation beyond your role: Just like with the former Tripadvisor CEO, Escalera says some professionals get typecast into their role. If they leave, it makes it hard for others to see them out of the context of that job: “This is why it’s so important to build real relationships where people understand your expertise and contributions beyond your title or company.”
2. Tailor your applications: When leaving a job or making a career pivot, ghosting might occur if a worker is no longer the perfect fit for new opportunities. “You might get shut out before you have a chance to prove you’re a fit. This is why it’s crucial not only to tailor your applications to highlight transferable skills but also to invest in networking and connections in the industry you’re hoping to move into.”
3. Don’t be afraid to follow up: Double-texting is totally appropriate, and Escalera says it’s good to follow up with recruiters, hiring managers, and potential connections. “Politely ask for a status update or express continued interest in connecting. One no-response doesn’t always mean no. People get busy, inboxes get crowded, and professional persistence can often pay off.”
4. Grow your network: Sometimes old connections still won’t respond after a follow-up, so it’s crucial for workers to expand their networks and keep the momentum up. “If you still don’t get a response, just keep building momentum by focusing on growing your network, applying to other roles, and staying visible.”

While it can be very dejecting for workers to be ghosted by others, Escalera says it’s important for professionals to keep their heads held high. The right companies or opportunities will come. 

“The right company will make it known they want you by engaging, following up, and making space for your brilliance,” Escalera says. “Keeping a positive mindset and knowing your worth helps reframe ghosting not as rejection, but redirection toward better-aligned roles and companies.”

This story was originally featured on Fortune.com

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• Eventbrite CEO Julia Hartz ditched her cushy TV career working on hit shows like Friends, Jackass, and The Shield to bootstrap the ticketing platform with her two cofounders, scaling it from a windowless phone closet. She exclusively tells Fortune they shelled out less than $250,000 to get the company up and running, reasoning that “if it’s a disaster, we’ll just be broke.” But the Gen Xer’s nail-biting sacrifice paid off, as Eventbrite now boasts a $225 million valuation and serves 89 million monthly users. 

Most people would jump at the idea of working on hit TV shows like Friends, Jackass, and The Shield, but Eventbrite CEO Julia Hartz left it all behind to pursue her passion of bringing people together. 

Just five years into her rising TV career—where she’d climbed the ranks to junior executive at FX—Hartz tossed the towel in on her 9-to-5 to launch Eventbrite in 2006, bootstrapping the company entirely with her husband and fellow cofounder Renaud Visage. 

The pitch was: “Come work on something that doesn’t exist. We’ll use our own money to fund it, and if it’s a disaster, we’ll just be broke,’” Hartz tells Fortune. 

Eventbrite is now estimated to be worth $225 million, and offers events ranging from wrestling classes, to comedy shows, to cheese raves with Queer Eye star Antoni Porowski.

But it all started when Hartz and her husband—serial entrepreneur and early PayPal investor Kevin Hartz—assembled a dream team to get Eventbrite off the ground. They recruited fellow cofounder Visage to come on board as chief technology officer, and the trio of entrepreneurs decided to chuck $250,000 of their own money to get Eventbrite running, moving to San Francisco.

Hartz had to sacrifice her job to put all her energy into Eventbrite, skirting the route other entrepreneurs have gone down: juggling a full-time job while scaling a company on the side. Instead, she found it best to wipe her slate clean and leave her TV career behind to pursue Eventbrite. It was a professional gamble that paid off in the long run. 

“I’ve seen entrepreneurs do that, and I think that that’s a clever way to gain validation and product market fit, without putting yourself in such a perilous state,” Hartz says. “I did not do that.”

Inspiration struck during her 9-to-5 job in TV working on Friends and The Shield

Hartz started working at just the age of 14—pouring coffees in cafes, and driving kids to after-school activities—and hasn’t taken her foot off the gas since. 

While attending Pepperdine University, she worked as an intern on the set of hit TV-show Friends, later scoring an internship at MTV in the series development department. It was a “magical” experience that eventually landed her a job at the station—once she graduated, Hartz went straight into developing shows including Jackass, The Shield, and Rescue Me across MTV and FX. Part of her job entailed researching fandom events, and suddenly, something clicked. 

“I remember going to this fandom event that was insanely niche, and feeling the energy of the people in the room, it just stuck with me,” Hartz says. “It was this palpable, kinetic energy…When we started Eventbrite, I was thinking about that all along: ‘How do we enable the people who gather others around these niche passion areas and create this magic?’”

While most couples may wring their hands at the idea of putting their finances on the line to launch a company together, Hartz’s partner was enthusiastic about going all-in on a light bulb moment. 

In fact, the Gen X CEO’s nearly 20-year success may have never panned out if it wasn’t for her husband Kevin—who’s success investing in the then little-known startup called PayPal—persuaded her to take the leap into entrepreneurship.

“It’s only serial entrepreneurs who can convince someone of that,” Hartz says. “We made it on less than a quarter of a million dollars…I’m really, really proud of it.”

Scaling a business idea into a $225 million ticketing giant

Once Hartz made the decision to leave TV forever, she packed her things into boxes, and drove up the coast of California to settle in her company’s new headquarters: San Francisco. The Silicon Valley hub had the tech connections and industry access to help get things off the ground. So just like that, she set up shop in Potrero Hill, the “warehouse district”.

“I was moving saw horses and plywood into a windowless phone closet on Monday, in this warehouse district in San Francisco, going in my head, ‘Wait, what if he’s crazy?’ Well, it’s a little late for that,” Hartz says. “I’ve been working since I was 14 with no break. So it was really important to me that I be working on day one.”

Eventbrite was able to get things off the ground thanks in part to perfect timing; in the mid-2000s, social media platforms were looking to bring together its users in real life. Facebook made Eventbrite one of its first connect partners, solidifying a huge new customer base looking for community events to partake in. 

Then 2008 came, and thousands of workers from all across the U.S. were being laid off in droves during the financial crisis. Hartz said “the world collapsed” in those dire years, and people were desperate for community while facing hardship. It was a tough era for corporate American workers, but was an opportunity for Eventbrite to bring them together. Over the next decade the business would amass a total of $373 million in equity funding through 11 fundraising rounds, according to Pitchbook, attracting investors like Tiger Global Management, Sequoia Capital and Square.

The ticketing platform has since amassed a fanbase in nearly 180 countries—in 2024 alone, it had distributed 83 million paid tickets for over 4.7 million events. With 89 million monthly users, people are scoring seats at events ranging from a sunset Bach concert in Central Park to a house music cruise on the Hudson river. 

This story was originally featured on Fortune.com

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• Nvidia CEO Jensen Huang is worth $151 billion—and he’s bringing his team along to the billionaires club with him. The AI boss said that he’s minted more billionaires on his management team than “any CEO in the world.” The culture at Nvidia is intense, but by shelling out for staffers, Huang reasons: “You take care of people, everything else takes care of itself.”

Nvidia’s CEO Jensen Huang has amassed a $151 billion net worth thanks to the success of his $4 trillion semiconductor company. And the ninth richest person in the world says he’s bringing his team into the exclusive billionaire club thanks to Nvidia’s envy-inducing compensation packages. 

“I’ve created more billionaires on my management team than any CEO in the world,” Huang said recently during a panel hosted by venture capitalists running the All-In podcast. “They’re doing just fine.”

Tech leaders at Meta, OpenAI, and Google are now also shelling out to attract top AI experts—with Meta even attempting to poach OpenAI employees with $100 million signing bonuses, according to leader Sam Altman. With the AI race being so hot, chief executives are reaping billion-dollar net worth gains from their company’s rising stock valuation, begging the question of whether their staffers are getting in on the pot of gold too. But Huang asserts that his employees are well-rewarded for Nvidia’s success.

“Don’t feel sad for anybody at my layer,” Huang said. “My layer is doing just fine.”

In fact, Huang noted that he personally reviews all employee compensation to ensure staffers’ wallets are stuffed. While he said the rumor that he has a stash of stock options on deck “is nuts,” he does confirm that he bumps wages every year to keep Nvidia workers happy. 

“I review everybody’s compensation up to this day,” Huang said. “I sort through all 42,000 employees, and 100% of the time I increase the company’s spend on [operating expenses]. And the reason for that is because you take care of people, everything else takes care of itself.”

Fortune reached out to Huang for comment. 

Huang’s loves a small, well-paid team of AI geniuses—and ‘tortures’ them into greatness

Nvidia employs tens of thousands of people—but having a small, nimble, well-funded AI team may be the ticket to the top. Huang emphasized that DeepSeek and Moonshot AI both have relatively slim AI crews, yet have capitulated to great business success. 

“150 or so AI researchers can probably, with enough funding behind them, create an OpenAI,” Huang said during the panel. “OpenAI was about 150 people, [as well as] Deepmind. They’re all about that size. There’s something about the elegance of small teams.”

Once talent manages to get onto the lean-and-mean AI team at Nvidia, they have to reckon with Huang’s cutthroat culture. Current and former staffers have described an “always-on” expectation, with one ex-employee saying she attended seven to 10 meetings every day, where fighting and shouting was common. The CEO’s grindset has clearly bled into the way staffers approach their work, and Huang’s leadership strategy entails pushing workers to the brink. But he isn’t willing to give up and fire people if they can’t do the job at hand, because he always thinks “they could improve.” 

“I’d rather torture you into greatness because I believe in you,” Huang said during a fireside chat with Stripe CEO Patrick Collison last year. While the CEO said he was being “tongue-in-cheek,” he doubled down: “I think coaches that really believe in their team torture them into greatness.”

And there’s an upside for working long hours and sitting through tense meetings—Nvidia employees get special compensation perks. The tech company allows employees to contribute up to 15% of their salaries to buy up company shares at a 15% discount. One mid-level employee even reportedly bought in for 18 years, and retired with shares worth $62 million. It’s a deal that’s so lucrative that it’s become “golden handcuffs” for many staffers who can’t bear the thought of losing the perk. In 2023, Nvidia had a 2.7% turnover rate, compared to 17.7% in the semiconductor industry at large. 

As Huang said in an interview with 60 Minutes last year: “If you want to do extraordinary things, it shouldn’t be easy.”

This story was originally featured on Fortune.com

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• 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

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