Listen to enough earnings calls, and you’ll start to hear something curious.

Two companies can be doing the same thing, numbers-wise. Similar revenue trajectories, solid margins, stable guidance. Yet one management team inspires investor trust while the other fills them with apprehension.

The reason usually has little to do with the numbers. It has to do with confidence — confidence in leadership, in direction and in the leaders’ understanding of the business and what needs to be done. And that has become one of the most critical factors in business over the past decade.

Companies have always known uncertainty is part of the job. What has changed is the pace at which that uncertainty is now traveling.

Every strategic move now happens in public

Any strategic change — a shift in the labor force, an acquisition, an AI initiative, a regulatory challenge, an earnings release — happens in full public view. Decision-makers no longer wait for the annual report to form their opinions. Investors, employees, customers and partners are forming them in real time. That has created an environment where perception and performance are essentially inseparable.

Management teams have long been told that numbers would talk, that good execution would get rewarded and that communication, while important, was secondary. That is no longer the case. Good execution remains essential. But execution without explanation fills a void, and vacuums are rarely empty. People fill them with assumptions, rumors, even propaganda.

The organizations that have mastered change are the ones that anticipate this dynamic early. They understand that communication is not an add-on to strategy but part of the strategy itself.

Context has become a competitive advantage

You see it most clearly in moments of transition. During a downturn, a technological shift or a reorganization, stakeholders search for cues. They want to know not only what is changing, but why. And it is often the “why” that determines how the “what” is received.

Consider the proliferation of artificial intelligence across industries. Reactions to the same announcement can differ dramatically depending on how the story is framed. Investors focus on productivity and future prospects. Employees focus on job security. Customers focus on how their experience will change. The facts are the same. The interpretations are not.

That means the job of a leader has grown larger than most executives appreciate. Making decisions is no longer sufficient. Leaders also have to help others understand why those decisions are being made. Without that context, even smart, effective moves can create alarm.

Credibility is the compounding asset

Credibility takes time to build. It develops through consistency, through demonstrated alignment between words and actions and through a stable narrative in good times and bad. Markets recognize it. Employees see it. Customers notice.

Once credibility is established, stakeholders are far more willing to give leaders room when uncertainty hits. They may not love every decision or agree with every strategy, but they are more likely to believe leadership has earned the benefit of the doubt.

That benefit is hard to quantify. It does not show up on the balance sheet or in quarterly reports. But it is real, and the best organizations in the world rely on it. Their leaders communicate clearly, reinforce context and direction and avoid disappearing — or overreacting — in a crisis. They have a consistent message about where the organization is headed.

Visibility is not the same as clarity

Modern business places enormous value on visibility. Leaders are expected to speak up, sit for interviews and make their case across platforms. Visibility has its role, but on its own it offers little. Visibility without clarity breeds noise. Clarity without visibility falls on deaf ears.

Effective leaders understand the connection between the two and use visibility to achieve clarity. That link matters more than ever now that decision cycles have compressed. Choices that once took weeks now take hours. Responses that once took days are expected almost immediately.

Leadership signals are market signals. Stakeholders are not only watching what an organization does — they are watching how its leaders manage uncertainty. Tone. Consistency. Confidence. Transparency. Those are the qualities that build trust and shape stakeholder behavior: patience from investors, engagement from employees, loyalty from customers and a willingness from partners to commit their own resources. All of it happens inside a confidence-rich environment.

Reputation is a leadership function, not a marketing one

Most leaders remain focused on outcomes — efficiency targets, revenue growth, cost control, market opportunity. Those metrics deserve careful attention. But far fewer organizations give the same attention to leadership’s reputation. That is a serious and expensive oversight.

Reputation may not be built on performance alone, but it heavily influences how performance is perceived. And leadership reputation becomes even more valuable in uncertain times. Reputation cannot be a marketing afterthought. It is a continuous leadership function.

The organizations building lasting confidence today understand that trust is not a byproduct of communication. It is a business asset that requires consistent investment — and it pays a real dividend when things get hard.

The best leadership question to ask right now may also be the simplest: Are stakeholders seeing our decisions the way we intend them to be seen?

Most leaders assume the answer is yes. The effective ones go out of their way to make sure.

Because the real mark of success is not only what an organization achieves. It is how many of the people around it believe in the leader guiding them toward it.

Listen to enough earnings calls, and you’ll start to hear something curious.

Two companies can be doing the same thing, numbers-wise. Similar revenue trajectories, solid margins, stable guidance. Yet one management team inspires investor trust while the other fills them with apprehension.

The reason usually has little to do with the numbers. It has to do with confidence — confidence in leadership, in direction and in the leaders’ understanding of the business and what needs to be done. And that has become one of the most critical factors in business over the past decade.

Summer isn’t just vacation season — it’s also one of the easiest times of the year to start earning extra income. As consumer spending shifts toward travel, outdoor activities, home improvement and personal development, countless seasonal opportunities emerge for aspiring entrepreneurs.

At the same time, today’s AI tools and no-code platforms have made it possible to launch online businesses faster and with less upfront investment than ever before.

Whether you’re looking to make extra money over the next few months or build a side hustle that continues generating income long after summer ends, the ideas below offer a mix of seasonal opportunities and long-term businesses that can grow well beyond the warmer months.

1. Online tutoring

If you have expertise in a subject like math, science, music, fitness or a foreign language, summer can be an ideal time to turn that knowledge into extra income. Parents often look for ways to keep their children academically engaged during the break, while adults use the slower summer months to learn new skills, prepare for exams or work toward personal goals. Thanks to video conferencing tools and online marketplaces, it’s easier than ever to connect with students without leaving home.

The demand for tutoring remains strong. According to Brighterly, U.S. high school students spend an average of 6.8 hours per week on homework, creating an ongoing need for additional academic support. Students who need help understanding concepts, completing assignments or preparing for the upcoming school year often turn to private tutors for guidance. Whether you teach online or in person, a small roster of recurring students can quickly turn tutoring into a reliable and flexible summer side hustle.

2. Boating tours

If you live near a lake, river or coastal destination, offering guided boat tours can be a lucrative summer side hustle. Some entrepreneurs purchase a small boat and build a seasonal business around sightseeing, sunset cruises, fishing trips or eco-tours. Others reduce upfront costs by leasing or renting a vessel for the summer and operating tours during peak tourist months. In many vacation destinations, visitors are willing to pay a premium for unique local experiences that can’t be replicated through traditional travel packages.

Safety is one of the most important aspects of running this type of business, making proper training and adherence to local regulations essential. According to Frank Azar, 69% of boating deaths occurred on boats where the operator had not received boating safety instruction. For aspiring tour operators, that statistic highlights an important opportunity: Investing in boating education and safety certifications can help build trust with customers while reducing risk. With the right equipment, licensing and marketing strategy, boat tours can become a profitable seasonal business that takes advantage of the increased travel activity during the summer months.

3. Become an AIO Specialist

As AI platforms like ChatGPT, Gemini, Claude and Perplexity increasingly influence how consumers discover products, services and information online, businesses are looking for ways to improve their visibility in AI-generated recommendations. This has created an opportunity for a new type of specialist: the AIO (AI Optimization) consultant.

The opportunity is becoming harder for businesses to ignore. According to Zen Reports, AI-driven traffic converts at rates ranging from 50% to more than 20 times higher than traditional organic search traffic. Optimizing for AI also requires a slightly different approach than traditional SEO. According to Aloha, 78% of Google’s AI Overview citations don’t come from pages ranking in Google’s top 10 organic results, demonstrating that visibility in AI-generated answers follows a different set of rules.

As a result, companies are becoming increasingly interested in understanding how AI systems discover, cite and recommend content, creating demand for professionals who can help improve their visibility across these platforms.

4. Build AI agents for small businesses

As artificial intelligence becomes more capable, many small businesses are looking for ways to automate repetitive tasks without hiring additional staff. This has created an opportunity for freelancers to build AI agents that can handle customer support, qualify leads, answer frequently asked questions, schedule appointments and assist with internal operations.

Demand for these solutions is growing as businesses move beyond simple chatbots and begin implementing AI systems that can take action on behalf of users. According to Respan, nearly 22.2% of AI gateway requests are now agent tool calls, accounting for 58.9% of all token volume. This suggests that organizations are increasingly relying on AI agents to interact with external tools, retrieve information and complete multi-step tasks rather than simply generating text responses.

Thanks to platforms like n8n, Zapier, Make and OpenAI, building AI agents is more accessible than ever. Entrepreneurs who understand workflows, automation and prompt engineering can create custom solutions for local businesses and charge setup fees, monthly retainers or ongoing maintenance contracts. As AI adoption continues to accelerate, helping companies automate routine work could become one of the most profitable side hustles of 2026.

5. Become a video game streamer

Gaming is no longer just a hobby. For creators who enjoy entertaining an audience, building a community or sharing gameplay experiences, streaming can become a legitimate side hustle. Platforms like Twitch, YouTube and Kick allow creators to generate income through subscriptions, donations, sponsorships, affiliate partnerships and advertising revenue.

The opportunity continues to grow as more people consume gaming content online. According to FollowersPanda, the global game-streaming market was worth approximately $12 billion in 2025 and is projected to reach $31.63 billion by 2033. As audiences spend more time watching gameplay, tutorials, reviews and live reactions, new creators have more opportunities than ever to carve out a niche and build a loyal following.

While success rarely happens overnight, streamers who consistently publish content, engage with their communities and focus on a specific game or genre can gradually turn their passion into a meaningful source of income. With major releases like GTA 6 expected to attract millions of viewers, 2026 could be an ideal time to start building an audience.

6. Become a high-value freelancer

Not all freelancers compete on platforms like Upwork or Fiverr. Many of the highest-paid writers, developers, marketers, designers and consultants attract clients directly by positioning themselves as experts in a specific niche. Instead of competing on price, they build a personal brand through platforms like LinkedIn, X, YouTube, newsletters, podcasts or industry events, allowing them to charge premium rates for their expertise.

According to Tailor Brands, there are approximately 59 million freelancers in the United States alone, making it increasingly important to stand out in a crowded market. As AI makes it easier to produce content and deliver basic services, clients are placing even greater value on recognized experts with proven experience and a visible reputation.

Building a personal brand takes time, but it can dramatically increase your perceived value, helping you attract better clients, charge significantly higher rates and create opportunities that extend far beyond traditional freelance marketplaces.

7. Build websites for local businesses

AI website builders, WordPress templates and no-code tools have made it easier than ever to launch professional websites in just a few hours. One practical lead-generation strategy is to search Google Maps for local businesses that have a Google Business Profile but no website listed, then reach out with a simple offer: a fast, mobile-friendly website delivered in three days for a few hundred dollars.

According to Galaxy, 98% of consumers search online before hiring a home services business, and AI-powered search is increasingly influencing where that discovery happens. For entrepreneurs with basic web design skills, building affordable websites — and offering hosting, maintenance, and ongoing updates — can quickly become a reliable source of recurring income.

8. Create outdoor living spaces

Summer is the busiest season for backyard upgrades, making it a great time to earn extra income by helping homeowners transform their outdoor spaces. In many areas, you don’t need to be a licensed contractor to get started. Many entrepreneurs build a business around pergola assembly, patio furniture installation, fire pit setup, outdoor lighting and coordinating local contractors for larger projects.

Demand for these services continues to grow as more Americans purchase new homes each year. According to the UHLS, an estimated 679,000 new single-family homes were sold in the U.S. in 2025. As more homeowners invest in making their backyards comfortable spaces for relaxing, entertaining and spending time with family, businesses that offer affordable installation, assembly or backyard makeover services can turn the busy summer season into a profitable side hustle.

The best side hustle isn’t necessarily the one with the biggest market — it’s the one you’ll actually stick with. Some of these ideas can generate income within weeks, while others have the potential to evolve into full-time businesses over the coming years.

Summer offers a unique combination of higher consumer demand, longer days and greater flexibility, making it an ideal time to test a new business idea. Even if only one of these opportunities turns into a steady source of income, taking action today could pay dividends long after the season ends.

Summer isn’t just vacation season — it’s also one of the easiest times of the year to start earning extra income. As consumer spending shifts toward travel, outdoor activities, home improvement and personal development, countless seasonal opportunities emerge for aspiring entrepreneurs.

At the same time, today’s AI tools and no-code platforms have made it possible to launch online businesses faster and with less upfront investment than ever before.

Whether you’re looking to make extra money over the next few months or build a side hustle that continues generating income long after summer ends, the ideas below offer a mix of seasonal opportunities and long-term businesses that can grow well beyond the warmer months.

Ford is betting on Apple software to shape its autonomous future. 

The $56 billion automaker said this week that it would use Apple software to power driver-assistance systems in its new line of electric vehicles to be released next year. According to The New York Times, the move puts Apple center stage in Ford cars, giving the iPhone maker an unprecedented, essential role in car operations. 

Apple CarPlay, which operates in more than 800 car models from major brands like Toyota, Ford and Chevrolet, enables drivers to link their iPhones with their vehicle screens, unlocking functions like Apple Maps. 

Ford is taking things one step further by letting Apple’s software help control how electric vehicles operate when they are driving themselves, per the Times. 

For the first time, Apple and Ford engineers are collaborating directly to improve self-driving features in cars set to reach dealerships next year. In the past, Apple worked independently from automakers. Engineers will build the new software into the vehicle, so drivers won’t need an iPhone to use it. 

“Apple Maps will be embedded in the vehicle, so you don’t have to pay anything extra,” Ford’s CEO Jim Farley said in an interview with the Times. “This is one of the most important announcements for Ford.”

Working with Apple will help Ford save money on developing new technology while still offering advanced driver-assistance features, according to Farley. Ford plans to introduce a new electric pickup truck embedded with these features starting next year, he added. 

A Ford group led by former Tesla executive Alan Clarke will oversee that truck as the first in a series of battery-powered models. Ford aims to price the pickup at about $30,000, much lower than many battery-powered vehicles on the market today.

Many automakers are reluctant to partner with tech companies

Eddy Cue, Apple’s senior vice president of services and health, told the Times that Ford is the first major car company to use Apple’s new automotive software. However, Apple intends to open it up to other automakers, he said. 

Car companies have often been cautious about working too closely with technology giants like Apple and Google. They worry about losing control over their customers and missing out on potential revenue to these larger and wealthier companies, per the Times. For example, Apple’s market value was $4.7 trillion at the time of writing, while General Motors trailed behind with a market value of $72 billion. 

Some newer carmakers, such as Tesla and Rivian, chose not to include Apple CarPlay or Google’s Android Auto in their vehicles. Instead, they built their own in-car software systems. These systems still let drivers use some outside apps, but the car company stays in control.

Now, some traditional automakers are thinking about doing the same. General Motors has already announced plans to remove Apple CarPlay from its future cars and replace it with its own software. Drivers will still be able to use certain apps from the likes of Apple and Google, but General Motors will control how the system works.

Ford is betting on Apple software to shape its autonomous future. 

The $56 billion automaker said this week that it would use Apple software to power driver-assistance systems in its new line of electric vehicles to be released next year. According to The New York Times, the move puts Apple center stage in Ford cars, giving the iPhone maker an unprecedented, essential role in car operations. 

Apple CarPlay, which operates in more than 800 car models from major brands like Toyota, Ford and Chevrolet, enables drivers to link their iPhones with their vehicle screens, unlocking functions like Apple Maps. 

In 2024, when Entrepreneur first connected with brothers Kirk McKinney, 22, and Jacob McKinney, 21, their Greater Boston-based junk-removal business, Junk Teens, was still a side hustle, albeit a $1.2 million one. 

The then-teenaged brothers launched Junk Teens back in 2021 with a single pick-up truck. A pair of working speakers found at a dump grew into a collection of resellable items — $1,000 worth — sold on Facebook Marketplace.

Now, the brothers’ largely student-run service, which also serves Cape Cod and Rhode Island, operates eight trucks and has 25 full-time employees. The business has handled an estimated 7.4 million pounds of items, sorting usable goods for donation, resale or repurposing whenever possible.

Junk Teens hit $3 million in revenue in 2025 and is projected to reach $5 million in revenue this year, per the company.

The company also grew its community partnerships. A computer drive with Computers 4 People distributed refurbished laptops and desktops to under-resourced communities, and a partnership with WellStrong on the Cape raised funds for wellness and peer-support programs that aid substance abuse recovery.

Here’s how the McKinney brothers unlocked their blue-collar business’s massive growth — and what’s next for Junk Teens. 

Breaking out of the bottleneck 

For a long time, Jacob scheduled employee routes and figured out where to dispose of the items they picked up. Managing it all was challenging when the business had a fleet of three to four trucks, just half of what it is now. 

“I was working 12 hours a day, nonstop,” Jacob recalls. “So I didn’t really have any more time to try to figure out how to hire someone else or anything like that. Long story short, one of the biggest first things we did was delegate my job position.”

The brothers split Jacob’s role into several different ones, which helped streamline employee bookings and hiring. 

“We promoted to manager one of our guys who had been with us for a couple years who was taking a gap year from college,” Kirk adds, “and gave him some of the responsibilities that Jake had, like calling in the employees every day and reviewing the schedule.”

With that in place, Jacob broke out of the bottleneck; he had more time to work with Kirk on building better systems and training, allowing the business to scale. 

Taking advantage of technology and AI — including vibe coding 

When Junk Teens hit $1.2 million in revenue in 2024, the entirety of the business’s day-to-day operations existed on Apple Notes.  

“Then Jake would sort those out and copy and paste those schedules to the guys that were going out every day,” Kirk explains. “That was how we ran our business. It was basically a $1 million side hustle at that point.” 

Now, Junk Teens is taking advantage of tech tools. The company uses Jobber for customer relationship management, GoHighLevel for customer data collection and Connecteam for employee management. 

The business is also embracing AI in its many forms, from the built-in “slight automation” that makes sense of data across the software programs it uses, to vibe coding its very own app. 

A Junk Teens employee who was on the team for several years and had basic tech skills built the app, using Base44 and ChatGPT for a lot of the UI and UX referencing. The app features a leaderboard and other statistics that help track employee performance — for instance, an employee’s revenue per hour or closing rate.

“Our entire app was developed by a teenager,” Kirk says. “That’s another interesting thing — that technology’s at the point where high school kids can create full apps. And our entire company uses that app every single day.” 

In the early days, Kirk edited content and posted videos on social media when he had the time. But Junk Teens has since systemized its social media strategy too. Now, Kirk collects footage when he’s out on the job, then outsources the editing to help realize his vision. 

About eight months ago, Kirk brought other Junk Teens team members on board too. 

“ I started training other guys on our team to go out there with Meta Glasses and GoPros and film some of their day-to-day operations and what they’re doing out in the field every day,” Kirk explains. “So now I have all this great content to work with, and then I can kind of be the translator between that footage and the team.” 

Currently, Junk Teens has surpassed 213,000 followers on TikTok, 269,000 followers on Instagram and 69,000 subscribers on YouTube.

Not only has systemizing Junk Teens’ social media approach helped market the business, but it’s also served as a major team-building tool. 

“A company is just a group of people at the end of the day, and when you see yourself in these videos and the social media’s capturing it, you’re a part of that, and it really elevates the culture,” Kirk says. “Then new people see what we have going on here, and it actually attracts more people who want to work with us.” 

Cultivating a vibrant culture around a young team

Most of Junk Teens’ employees are high school or college students, and the company aims to pay them more than its competitors to attract top talent. 

On average, that pay works out to about $25 to $30 an hour, including hourly rates, commissions and tips. 

“A lot of the employees feel like they’re building the company with us because they’re also building their opportunity as the company grows,” Kirk says. “Because of that, we have a lot of forward-thinking people, and I think that us all being young is a part of why that happens.”

Although Junk Teens loses some employees when the school year starts back up, the seasonality of junk removal aligns well with the ebb and flow, and the brothers always plan for it. 

The business’s volume nearly doubles in the summer months; the new Cape Cod location alone booked $350,000 in services during peak season last year. 

What’s more, Junk Teens’ young team members bring an open-mindedness and high energy that make for a vibrant company culture, the co-founders note. 

“In that scenario where someone had something happen in their life where they might be a little down coming in the next day, they get picked right back up because there’s 10 or 15 other guys that all have high energy around them,” Jacob adds. “It’s impossible to still act sad or down when you’re in that type of environment.” 

Perfecting systems for a nationwide scale

Now, the McKinney brothers are focused on perfecting their business’s systems as they eye a national expansion, ideally within the next couple of years. 

“ For me, the most exciting thing is empowering the youth,” Kirk says. “With technology, there are so many opportunities to make money. But everyone’s always going to need junk removed. There’s always going to be high schoolers looking for after-school and summer jobs. And young people are looking for different career paths other than the traditional college route.” 

The co-founders receive daily DMs from young people asking for advice on starting a business. They would encourage anyone who’s considering it to stop procrastinating and go for it. 

“I don’t think there’s ever a perfect roadmap unless you already have $1 million and are a business expert, which we were not, and most people starting businesses are not,” Jacob says. “So start, even if it’s not going to be the business that you retire with. We just started with something that we thought was adventurous and entertaining, not even something that we thought would make us the most money.” 

This article is part of our ongoing Young Entrepreneur® series highlighting the stories, challenges and triumphs of being a young business owner.

In 2024, when Entrepreneur first connected with brothers Kirk McKinney, 22, and Jacob McKinney, 21, their Greater Boston-based junk-removal business, Junk Teens, was still a side hustle, albeit a $1.2 million one. 

The then-teenaged brothers launched Junk Teens back in 2021 with a single pick-up truck. A pair of working speakers found at a dump grew into a collection of resellable items — $1,000 worth — sold on Facebook Marketplace.

Now, the brothers’ largely student-run service, which also serves Cape Cod and Rhode Island, operates eight trucks and has 25 full-time employees. The business has handled an estimated 7.4 million pounds of items, sorting usable goods for donation, resale or repurposing whenever possible.

In 2008, the financial world was coming apart at the seams. I was at Morgan Stanley, and no one knew what was coming next. But when leadership came in to talk to us, they did it in a way that let us exhale. They didn’t paint a rosy picture. They were direct, and they brought us into the process of solving the problem. At a time when giants like Lehman Brothers and Bear Stearns were crumbling, they gave us a lifeline of confidence. They reinforced the idea that we were partners in finding a way forward, and they rallied the team at a moment when morale was at rock bottom.

Every leader will eventually have to deliver disappointing news — a missed target, a restructuring, a canceled initiative, a budget reduction, a layoff. These conversations are hard for everyone involved. Behind every business decision are people whose work, plans and expectations may be affected.

Over the course of my career, I’ve learned that trust isn’t damaged by the news itself. Trust is damaged when people feel surprised, confused or excluded from understanding why decisions were made. Trust gets built one transparent conversation at a time.

When leaders communicate difficult news with clarity and honesty, people are far more likely to stay engaged — even when they disagree with the outcome. I rely on a simple four-part framework whenever I have to deliver a hard message. It helps people understand what is happening, why it is happening and how we move forward together.

Start with the facts

When people sense bad news is coming, they want clarity. Leaders often spend too much time building up to the message. They provide excessive background, soften the language or avoid the core issue altogether. As a result, people become distracted trying to figure out what is actually being said.

State the decision clearly and early. We are reducing the size of the organization. We will not hit the target we committed to this quarter. We’ve decided to stop this initiative.

Direct communication is a form of respect. It gives people a clear understanding of the situation and lets them focus on the information that follows.

Explain the business context

Once people understand the decision, they need to understand the reasoning behind it. Context matters because it connects the decision to the broader realities the organization is facing. Without it, assumptions and skepticism fill the gaps.

Whenever feasible, share the factors that led to the decision — the business conditions, strategic priorities, market changes or operational realities that shaped the outcome. The goal isn’t to justify the decision or win consensus. It’s to help people understand it. When people understand the circumstances leaders are navigating, they are better able to accept difficult outcomes and maintain confidence in the team steering the ship.

Acknowledge the impact

Business decisions affect people differently. Some will feel disappointed. Others may feel uncertain, frustrated or worried about what comes next. Leaders should acknowledge that reality directly.

If you hired well, these are sharp, capable people — they need information, and they need to know you’re mindful of them. Leaders who cling to platitudes miss the chance to create alignment and squander the trust of their team in the process.

People want to know that leadership understands the consequences of the decision. They want to know that leaders have considered the human side of the equation. Acknowledging impact doesn’t require lengthy emotional discussions. It requires awareness, sincerity and respect.

Provide a path forward

After difficult news is delivered, attention quickly shifts to the future. People want to understand what comes next, what priorities remain unchanged and where to focus their efforts.

This is where leaders need to create direction. Be forthcoming about next steps. Clarify expectations. Explain where the organization is headed and how the team will move forward. Even when circumstances are challenging, clarity creates stability. People can navigate uncertainty when they understand the mission and their role within it.

The moment that matters most

It’s easy to be a good leader when the news is good. The moments that actually shape trust are the difficult ones. People remember whether leaders communicated openly. They remember whether they got honest, authentic explanations. They remember whether they were treated with respect.

In my experience, difficult conversations become far more effective when leaders focus on four things: communicating the facts, providing context, acknowledging impact and creating clarity about what comes next.

The news may still be hard. The relationship doesn’t have to be.

In 2008, the financial world was coming apart at the seams. I was at Morgan Stanley, and no one knew what was coming next. But when leadership came in to talk to us, they did it in a way that let us exhale. They didn’t paint a rosy picture. They were direct, and they brought us into the process of solving the problem. At a time when giants like Lehman Brothers and Bear Stearns were crumbling, they gave us a lifeline of confidence. They reinforced the idea that we were partners in finding a way forward, and they rallied the team at a moment when morale was at rock bottom.

Every leader will eventually have to deliver disappointing news — a missed target, a restructuring, a canceled initiative, a budget reduction, a layoff. These conversations are hard for everyone involved. Behind every business decision are people whose work, plans and expectations may be affected.

Over the course of my career, I’ve learned that trust isn’t damaged by the news itself. Trust is damaged when people feel surprised, confused or excluded from understanding why decisions were made. Trust gets built one transparent conversation at a time.

Brendan Foody, the 23-year-old CEO of AI talent and data-labeling platform Mercor, thinks that young job candidates should stay at companies for longer stretches of time. When reviewing young applicants, Foody found that average tenure was shorter than he expected; they were staying at jobs for a year before jumping to the next big thing. 

Earlier this week, Foody wrote on X that he received “too many” job applications from young people who were “serial job hoppers.” These candidates “jump to the hottest company every year” because they are under the mistaken belief that “it looks good on a resume,” he said. 

“Too many people in my generation underestimate how much relationships, reputation, equity, and trust compound over time,” Foody wrote. He added, “But look at almost anyone who’s built something extraordinary: they weren’t serial job hoppers.”

Josh Elman, partner at Silicon Valley venture capital firm Andreessen Horowitz, replied to Foody’s post on X. 

“You are right that going from job to job without meaningful contributions nor closure is a bad pattern,” Elman wrote. “But it is worth going deeper with people who continue to work on important things at important times. That perspective compounds.”

Foody added in an email to Business Insider this week that employees should pursue new jobs for the “right reasons.” For example, they could have stopped learning at a particular job. 

“Moving because the work is better is very different from moving because a logo looks good on a resume,” he noted.

Foody is one of the youngest billionaires in the world, with a net worth of $2.2 billion at the time of writing, per Forbes.

Why Gen Z is prone to job-hopping

Gen Z has earned a reputation as the job-hopping generation. A 2021 report from careers site CareerBuilder found that Gen Z workers spent an average of two years and three months in a role, compared with two years and nine months for millennials, reinforcing the idea that younger workers cycle through jobs faster than older ones.

In a 2023 survey by consulting firm Oliver Wyman, 70% of Gen Z respondents in the U.S. and UK who described themselves as “loyal” to their employer were nonetheless actively looking for a new role.

Why has Gen Z taken to job-hopping? For years, switching jobs was closely linked with higher pay, which helped normalize frequent moves as a rational strategy rather than a red flag. For example, one employment attorney who spoke with Business Insider last year grew her salary from $40,000 to $225,000 in six years by strategically job-hopping. 

Foody said he was aware of the potential financial upside to job-hopping. “Switching jobs can often be the fastest way to get a raise or a title bump in the near term, so the incentive feels real,” he said in the email to Business Insider.

He added that compensation was increasing rapidly in San Francisco, the city he lives in, contributing to the desire to switch jobs. 

“In tech, and especially in AI right now, the pull is strong,” he wrote. “The grass always looks greener.”

Brendan Foody, the 23-year-old CEO of AI talent and data-labeling platform Mercor, thinks that young job candidates should stay at companies for longer stretches of time. When reviewing young applicants, Foody found that average tenure was shorter than he expected; they were staying at jobs for a year before jumping to the next big thing. 

Earlier this week, Foody wrote on X that he received “too many” job applications from young people who were “serial job hoppers.” These candidates “jump to the hottest company every year” because they are under the mistaken belief that “it looks good on a resume,” he said. 

“Too many people in my generation underestimate how much relationships, reputation, equity, and trust compound over time,” Foody wrote. He added, “But look at almost anyone who’s built something extraordinary: they weren’t serial job hoppers.”

Scott Winters turned to ChatGPT to explain his dizzy spells that once forced the Florida pastor to stop mid-sermon. Over time, the chatbot stopped recommending he see a doctor and instead told him his symptoms were “not something dangerous,” even telling him to trust that “God did not design your body to endlessly fail.” Winters spent weeks stuck in a recliner before he was hospitalized in July 2025 with a life-threatening pulmonary embolism, the New York Times reports.

He’s now suing OpenAI and CEO Sam Altman in San Francisco Superior Court, accusing the company of negligence and the “unauthorized practice of medicine.” It’s reportedly the first lawsuit claiming a chatbot’s health advice directly harmed someone seeking medical guidance.

The case lands just as OpenAI pushes deeper into health tools like ChatGPT Health. An OpenAI spokesman said the chatbot isn’t intended for diagnosis or treatment, but that the company takes health-related safety seriously. As AI increasingly stands in for medical advice, especially for people who can’t easily see a doctor, the case raises real questions about who’s liable when that advice goes wrong.

Scott Winters turned to ChatGPT to explain his dizzy spells that once forced the Florida pastor to stop mid-sermon. Over time, the chatbot stopped recommending he see a doctor and instead told him his symptoms were “not something dangerous,” even telling him to trust that “God did not design your body to endlessly fail.” Winters spent weeks stuck in a recliner before he was hospitalized in July 2025 with a life-threatening pulmonary embolism, the New York Times reports.

He’s now suing OpenAI and CEO Sam Altman in San Francisco Superior Court, accusing the company of negligence and the “unauthorized practice of medicine.” It’s reportedly the first lawsuit claiming a chatbot’s health advice directly harmed someone seeking medical guidance.

The case lands just as OpenAI pushes deeper into health tools like ChatGPT Health. An OpenAI spokesman said the chatbot isn’t intended for diagnosis or treatment, but that the company takes health-related safety seriously. As AI increasingly stands in for medical advice, especially for people who can’t easily see a doctor, the case raises real questions about who’s liable when that advice goes wrong.

I run a healthcare technology company, and I did not come into this with a formal background in AI. What I have are views shaped by building and testing these systems inside a live business, and those views are evolving fast.

Some leaders I know are all in. They are testing tools, prompting systems, learning what works and what does not. I am one of them. We are also providing ongoing, individualized training to make sure every leader on our team has the support to do the same. We are not asking people to figure it out on their own. We are asking them to engage, and we are giving them what they need to succeed.

Others are waiting. They want the technology to feel more polished, more proven, safer. That instinct creates a false sense of control. You do not need a perfect system to get value from AI. The advantage is built by working through imperfect ones. That is how you learn where they break and how to make them better.

The gap you cannot see until it is too late

There is a real difference between understanding what AI can do in theory and knowing how to apply it inside your organization. That difference is not closed by reading about it or watching a demo. It is built through experience. It comes from prompting a system, iterating on the results, course-correcting and refining your inputs over time.

That last part matters more than most people realize. You are not refining the outputs. You are refining your prompts and your inputs. The outputs are what happened. What you are actually developing is the ability to translate how your organization works into instructions a system can act on. That skill does not exist without practice, and it cannot be built from the outside.

While one group is avoiding early mistakes, another is building internal knowledge. And the gap compounds. By the time the technology feels stable to those who waited, the leaders who engaged early are no longer learning the basics. They are optimizing, scaling and embedding these systems into how their organizations actually operate.

What educating AI actually looks like

Most people understand large language models in the abstract. AI goes out to the world, processes an enormous volume of information and generates outputs. What is less understood is the work of educating that model on your specific business. That is where the real leverage lives, and it requires intentional effort.

In practice, it starts with loading the system with everything your organization knows as it exists today. That means your policies and procedures, your legal documents, your existing workflows, your financials, your sales activity data, your onboarding process, your customer history. Then you layer in user experience. In our business, that sounds like this: What does a case manager actually do today? What does an intake specialist handle? What does an account resolution specialist deal with? You are describing the business as it is, not as you wish it were.

Once that foundation is in place, you prompt toward outcomes. Not toward how you think those outcomes should be achieved — toward the outcomes themselves. Show me where our time-to-funding dropped from 14 days to two. Show me what our customers said they wanted and where we are falling short. Show me the activity our sales team is running versus what the close rate actually requires. Review the materials, identify the gaps and suggest the improvements. All of it aimed at more revenue, better margins and stronger customer satisfaction.

This is not the same as workflow redesign. Workflow changes are a much later output. What you are doing in the early stage is education and prompting for iterative change. Think of it as a second set of eyes on the business, one that can analyze across more variables than any individual could and surface opportunities you might not have identified on your own.

Before you implement anything the system recommends, you review it. You iterate. You train around it. That process is how trust gets built, and it requires genuine engagement from leadership.

What the shift from doing to prompting actually requires

The organizations getting the most from AI are not just adopting tools. They are rethinking how work flows through the business. This shift is less about technology and more about clarity. If your workflows are unclear, if ownership is vague, if success is not well defined, the system will not expose those problems. It simply will not be able to answer well. Garbage in, garbage out is not a cliché. It is an accurate description of what happens when a system is educated poorly.

What used to be execution is now direction. What used to be programming is now prompting. The leaders getting the most value understand their product, their customer and their workflows deeply enough to educate a system on all of them. Then they prompt toward their whiteboard goals without telling the system how to get there. That discipline — staying out of your own way and letting the system suggest the path — is where most leaders struggle at first.

This is also why I believe the real competitive skill here is not technical. I would take a strong operator with deep business knowledge over a technical expert any day. The person who understands what the organization does, how it does it and what it is trying to achieve is better positioned to educate and prompt these systems effectively than someone who can only describe how they work mechanically.

The risk is already here

Concerns about reliability are legitimate. In regulated environments, a flawed output is not always contained. It moves through a workflow, influences decisions, reaches customers or patients and can create legal or compliance exposure that is difficult to unwind. Those risks are real, and they are why early experimentation should happen in lower-stakes environments with clear human review built in.

But waiting does not eliminate that risk. It shifts it. The organizations sitting on the sidelines are accumulating a different kind of exposure: a widening capability gap, an inability to attract talent that expects these tools to be part of how work gets done, and a slower response time when the competitive environment demands it.

In our organization, I am direct about where I stand. AI is not replacing humans. It is replacing humans unwilling to utilize it. That is not a threat. It is a description of what is already happening. We are providing every leader with the training, support and access they need to engage. Those who choose not to will eventually face that reality regardless of where they work.

The companies that are winning are not waiting for a better version. They are building their knowledge base right now, educating their systems on how the business actually works and prompting toward outcomes their competitors are not yet positioned to achieve. That head start does not wait for anyone.

I run a healthcare technology company, and I did not come into this with a formal background in AI. What I have are views shaped by building and testing these systems inside a live business, and those views are evolving fast.

Some leaders I know are all in. They are testing tools, prompting systems, learning what works and what does not. I am one of them. We are also providing ongoing, individualized training to make sure every leader on our team has the support to do the same. We are not asking people to figure it out on their own. We are asking them to engage, and we are giving them what they need to succeed.

Others are waiting. They want the technology to feel more polished, more proven, safer. That instinct creates a false sense of control. You do not need a perfect system to get value from AI. The advantage is built by working through imperfect ones. That is how you learn where they break and how to make them better.

I have spent most of my professional life sitting at the intersection of ideas and capital. Over time, you develop a sense for when something is working and when it is not.

Price is meant to be a signal. It is supposed to communicate information between people who are building something and people who are deciding whether to support it. When price works, it coordinates behavior. It tells creators where to focus and gives investors a way to measure progress over time, but there are moments when price stops discovering value and starts suppressing it. This shift changes what gets built, how long companies are allowed to mature and who gets to participate in growth. When that happens, we still talk about valuation, but what we are really doing is negotiating around fear. 

When valuation becomes compression

Modern finance is extremely good at measuring what already exists. It is far less effective at recognizing what is still forming. If it exists on a balance sheet or inventory, a good financier can estimate its value. When the thing of value is still in development, the waters become much murkier.

I have advised entrepreneurs for decades on raising capital for their businesses — real companies with customers, employees and momentum. Again, I have watched valuation conversations turn into exercises in leverage. Whoever controlled capital dictated the structure, the pace, and ultimately, the price. This outcome is the product of incentives that reward certainty over development and speed over patience.

I saw this dynamic clearly while working alongside the founders of Archipelago ECN, one of the earliest platforms to execute equity trades over the internet. We solved fragmentation in the markets, improved pricing efficiency and increased speed. When trading volume became the dominant driver, entire categories of companies, particularly smaller and earlier-stage public companies, quietly stopped mattering to the system.

The consequences show up quickly. The number of publicly traded companies dropped. The immediate result was a shrunken marketplace with a reduced pipeline of new entrants. 

Those that remained found themselves competing against the giants in the market. The necessity to show growth over everything else led founders to begin optimizing for near-term benchmarks instead of building durable businesses. Capital providers prioritize early extraction over long-term participation to avoid opportunity cost. 

When companies are pushed toward premature exits or forced to remain private far longer than what makes sense, the price is wrong because the system never allowed it to be right.

Equilibrium pricing as alignment

Equilibrium pricing begins with a simple observation: Value does not arrive fully formed. Before there is revenue, there is effort. Before there is volume, there is work. Before there is certainty, there is risk taken by people who believe in an idea enough to build it. Equilibrium pricing respects that process. Capital must be aligned with a company’s stage of development. When it is not, timelines compress and decision-making distorts. 

I have seen this alignment change outcomes instantly. For example, a company I advised struggled to secure a $5 million working capital line while private, despite steady operations and clear growth prospects. Shortly after becoming public, without any meaningful change to the business itself, its bank extended a $20 million credit facility. The difference was transparency, liquidity and price discovery operating in an environment designed to recognize development, not discount it.

Misalignment is often visible in how capital behaves under pressure. Capital that demands certainty before development has occurred, or accelerates timelines unnaturally or prioritizes extraction over progress, signals that alignment has already been lost.

Markets function best when valuation occurs in environments where information, participation and discipline can coexist. 

Too much of today’s valuation happens behind closed doors. Numbers are attached to ideas through private negotiation, but the broader market never sees how those numbers were reached or participates in the growth that follows. 

AI, algorithms and repeating the same mistake faster

Artificial intelligence (AI) now sits at the center of modern financial analysis. It processes information faster than any human ever could. But speed does not equal wisdom. If valuation models are built around short-term outputs, algorithms will optimize relentlessly around those outputs. If markets reward volume over development, AI will accelerate that preference. The result is faster repetition of the same blind spots.

This is where market design becomes inseparable from technology. Algorithms are only as good as the environments in which they operate. Public markets structured for smaller companies generate different data than private negotiations. They introduce transparency, discipline and participation without forcing premature scale. Outside of those environments, algorithms risk making the same mistake perfectly, millions of times over. 

The greatest risk is the systematic failure to recognize opportunity because the tools are pointed in the wrong direction.

Letting price discover value again

Price is one of the most powerful coordination tools ever created. When it functions properly, it allocates resources, rewards contribution and supports growth. 

Equilibrium pricing is about restoring balance. It means aligning incentives, matching capital to stage and designing public infrastructure that values development alongside liquidity. That is how durable value has always been created.

If we want capital markets to support the next generation of transformative companies, we must give price the conditions needed to work. When alignment exists, price starts revealing possibility. 

For leaders, restoring alignment requires deliberate choices:

• Examine how you define risk.
  Ask whether your valuation frameworks allow time, effort and development to register as information.
• Match capital to the stage of growth.
  Capital that aligns with development allows price to emerge.
• Separate speed from insight.
  Faster analysis does not guarantee better valuation. Ensure technology is operating meaningfully.
• Favor environments where price can evolve.
  Valuation works best where transparency, participation and discipline coexist. 
• Design incentives that reward participation, not extraction.
  When incentives prioritize early control over long-term contribution, price becomes distorted. Alignment corrects that.

Markets fail when the systems meant to recognize value are pointed in the wrong direction.

I have spent most of my professional life sitting at the intersection of ideas and capital. Over time, you develop a sense for when something is working and when it is not.

Price is meant to be a signal. It is supposed to communicate information between people who are building something and people who are deciding whether to support it. When price works, it coordinates behavior. It tells creators where to focus and gives investors a way to measure progress over time, but there are moments when price stops discovering value and starts suppressing it. This shift changes what gets built, how long companies are allowed to mature and who gets to participate in growth. When that happens, we still talk about valuation, but what we are really doing is negotiating around fear. 

When valuation becomes compression

Modern finance is extremely good at measuring what already exists. It is far less effective at recognizing what is still forming. If it exists on a balance sheet or inventory, a good financier can estimate its value. When the thing of value is still in development, the waters become much murkier.