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The skills that help you build a company are not always the same skills you need to lead it at scale.

When a company is small, the CEO knows almost everything that is happening. You know the people, the clients and where the biggest opportunities are. You are close to the details, and when something goes wrong, you can usually get involved and help fix it yourself.

I remember that stage of my career clearly. There was a certain comfort in being close to everything. Decisions could be made quickly because the distance between a question and the person making the decision was very short.

Then the company grows, markets expand, teams multiply, new offices open, customers come from different parts of the world. Decisions become larger, the consequences become harder to see immediately, and there are simply more things happening than one person can follow.

That is when I learned one of the harder lessons of leadership: The way you lead a company at one stage of its growth can become a limitation at the next. For a CEO, growth requires a change in role.

You stop being the center of every decision

In a growing company, there is a natural temptation to stay involved in everything.

It comes from a good place. You care about the business. You know its history. You have developed instincts that have served you well. You may even believe that your involvement protects the quality of decisions.

Eventually, though, the volume makes that impossible. The more important question becomes whether you have built a team that can make good decisions without you. That question has changed the way I see leadership.

At BGN, we operate across more than 120 countries, with people working across different markets, cultures and areas of expertise. I cannot be in every room where a decision is being made. Nor should I be.

My responsibility is to make sure the people in those rooms understand the direction of the company, the standards we expect and the judgment required to act in its best interests.

That takes time. It also requires trust.

The hardest thing to delegate is judgment

Delegating a task is relatively easy; however, delegating a decision is much harder.

The real test comes when you give someone responsibility for something important and resist the urge to step back in when they approach it differently from the way you would have. That is where leadership gets uncomfortable.

People need room to develop their own judgment. They need to make decisions, learn from the consequences and gradually take on more responsibility.

If a CEO corrects every decision before a person has had the opportunity to own it, that person learns something very quickly: Wait for the CEO. And that is exactly what a growing company cannot afford. The goal is to develop leaders who can think independently while remaining aligned with the company’s values and objectives.

I have found that this takes more than hiring talented people. It requires giving them meaningful responsibility and allowing them to grow into it.

Show me your calendar, and I’ll tell you what kind of CEO you are

One of the clearest signs that a company has changed is the CEO’s calendar.

Early in a company’s life, the calendar can be filled with operational questions: Which customer needs attention? Which deal needs to be closed? Which problem needs solving today?

As the company grows, the most valuable use of a CEO’s time changes. You need to spend more time thinking about where the company should be in three, five or 10 years. Which markets deserve investment? Where should we build? Which capabilities will we need? Who are the leaders who can take the company forward? What should the organization stand for as it grows?

Those questions rarely produce an immediate result: There is no satisfying feeling of crossing something off a list, and yet they may be among the most consequential decisions a CEO makes.

I have become increasingly protective of time for that kind of thinking. A full calendar can create the feeling of productivity while leaving little room for perspective. The larger the company becomes, the more valuable perspective becomes.

You have to let the company become bigger than you

There is a personal side to this transition that people do not talk about enough.

When you have spent years building a business, your identity can become closely connected to it. You know the history. You remember it all: the difficult years, the people who took a chance on the company when it was smaller, the decisions that changed its direction. That history is never truly behind us; it shapes where we go.

But the company also has to develop an identity of its own. If every important relationship, decision or opportunity depends on the CEO personally, the organization remains smaller than its size suggests.

A strong company should be able to carry its values through many people. That means developing leaders who can represent the business with customers and partners as well as giving people enough context to understand why decisions are made. It also means creating a culture where standards remain consistent even when the CEO is not present.

For me, that is one of the most rewarding parts of leadership.

Seeing someone you have developed walk into a room and handle a situation exceptionally well gives you a different kind of satisfaction from solving the problem yourself. You realize the organization is growing its own strength.

The CEO has to keep learning too

There is another trap that comes with seniority: People begin to assume that because you are the CEO, you should already know the answer.

Sometimes you do, but let’s face it — often you do not.

The larger and more international a company becomes, the more important it is to remain curious. Someone who works close to a customer may understand something the executive team has missed. A colleague in another market may see an opportunity that looks invisible from headquarters. A younger member of the team may question an assumption that has been accepted for years.

I want people around me who are willing to challenge my thinking. That requires humility, but it also requires confidence. A leader who feels threatened every time someone disagrees will eventually surround herself with people who agree too easily. That is dangerous for any company.

The CEO has to keep listening, especially when the company becomes large enough for the leader to hear mostly what other people think she wants to hear.

Growth changes the questions

I think about the evolution of leadership through the questions we ask.

When you are building a company, you ask, “How do we make this work?” As the company grows, the question becomes, “Who can make this work without me?” Then it becomes, “How do we build an organization that can keep growing?” And eventually, “What kind of company are we building for the people who will lead it after us?”

That last question changes the perspective completely.

It moves leadership beyond the next deal, the next quarter or even the next stage of growth. It makes you think about culture, talent, reputation and institutional knowledge. It makes you think about whether the company can continue to evolve when the people who built it eventually step aside.

That is a responsibility I take seriously.

Growth should change the CEO too

A company can only grow as far as its leadership is willing to grow with it.

For me, that has meant becoming more comfortable with distance from the details and more deliberate about where my attention belongs. It has meant trusting people with decisions that I once would have wanted to make myself. It has meant accepting that someone else may approach a problem differently and still reach an excellent outcome.

Most importantly, it has meant understanding that leadership at scale is a different job.

The instinct to get involved is still there. So is the satisfaction of solving a difficult problem yourself. But there is a greater satisfaction now in seeing a team solve something that once would have landed on my desk.

That is how you know the company is becoming bigger than its founder, its CEO or any single individual.

And perhaps that is one of the clearest signs that you have built something that can last.

The skills that help you build a company are not always the same skills you need to lead it at scale.

When a company is small, the CEO knows almost everything that is happening. You know the people, the clients and where the biggest opportunities are. You are close to the details, and when something goes wrong, you can usually get involved and help fix it yourself.

I remember that stage of my career clearly. There was a certain comfort in being close to everything. Decisions could be made quickly because the distance between a question and the person making the decision was very short.

Many brands use the U.S. Open to entertain clients or put up flashy signage. IBM does both, but its involvement goes much deeper. Behind the scenes, the century-old tech titan is the invisible hand shaping the fan experience, powering the U.S. Open app, and engaging 14 million fans worldwide. In the process, IBM is making the case that sports might be the perfect playground for AI integration.

The servers behind each serve 

From a fan’s perspective, it seems simple. You open the app, check the score and maybe watch a highlight or two. But making that experience work requires IBM and the USTA to process a mountain of data in real time, using AI alongside human review to balance speed and accuracy. One new metric, Serve Quality, analyzes 21 data points across a player’s body and racquet 50 times per second, generating roughly 4.6 million data points per match and more than 1.2 billion throughout the tournament. And then there’s the match chat, an AI bot that lets users ask conversational questions about the sport, like “what is the record for x?” 

Users appear to be embracing these features, if the numbers are any indication: More than 14 million unique devices engaged with U.S. Open digital platforms in 2025, generating nearly 47 million visits, up 19% year over year.

So why does the USTA need IBM to help run a tennis tournament? To understand that, you have to recognize that the U.S. Open isn’t simply a sporting event. It’s a massive, temporary business operation with millions of customers, enormous amounts of data, and a three-week deadline. That comes with a litany of challenges, from security and bandwidth to content production and infrastructure, that require the scale and experience of a company like IBM.

The USTA is a few-hundred-person team that’s expected to scale monumentally during those three weeks each year. With IBM’s help, however, it can deploy AI-powered tools to streamline infrastructure management, optimize costs, enhance content production workflows, and improve operational resilience. For example, the USTA’s small editorial team uses bespoke AI tools to generate match summaries, which humans then review and edit, increasing the team’s content production capacity by 300%. 

On top of that, an operation as large as the U.S. Open comes with major security risks, and IBM plays a key role in deterring them. According to a spokesperson, IBM protects against nearly 500 million suspicious requests targeting the USTA’s infrastructure and digital platforms. Its AI agents help identify, categorize and prioritize potential threats, allowing the team to respond faster and better protect the USTA’s assets.

Rallying fans around the world  

At the heart of this year’s experience is the all-new Live Updates homepage, a smarter, more personalized way for fans to follow the action that matters most. Fans can prioritize their favorite players and quickly zero in on the matches, insights and stories they care about most. From the World Cup to the NBA Finals, this summer has made one thing clear: demand for sports is exploding, but stadium seats aren’t.

For the millions of fans who can’t afford to attend the tournament or live too far away to travel to New York, these digital experiences let them feel closer to the action.

Here are some of the other new features in the U.S. Open app this year:

1. Match Chat: An AI-powered assistant that lets fans ask free-text questions about live matches and receive instant answers and insights based on match statistics, player information, historical performance, and tournament data. Responses are generated using AI agents and models trained in the USTA’s editorial style and the language of tennis.
2. Live Likelihood to Win: A real-time predictive feature that continuously updates each player’s chances of winning as a match unfolds, using live scores, statistics, and expert analysis. The AI-powered visual representation shows how match momentum is shifting in real time, essentially serving as the heartbeat of the match.
3. Key Moments: A generative AI feature within Live Likelihood to Win that goes a layer deeper, explaining why a player’s chances of winning changed by identifying the points, rallies, and sequences that had the biggest impact on match momentum.

While much has been made of the public’s skepticism toward AI, an IBM study found that sports fans have been fairly receptive. The IBM 2026 Sports Survey found that 80% of fans see value in AI-powered sports experiences, particularly real-time statistics, personalized content and translation. Among tennis fans, 64% said they trust AI-generated sports content.

The study also highlights the importance of having a strong digital presence. IBM found that 73% of tennis fans surveyed use sports apps. In comparison, 91% use them during live events, making a reliable, real-time digital experience increasingly important to how fans consume and engage with sports.

Image Credit: IBM

Playing the long game  

The U.S. Open isn’t IBM’s only sports play. The company is also involved with the UFC, the Masters, and Wimbledon, where it runs similar programs, powering digital platforms and handling data for each respective event. But IBM’s sports strategy extends beyond working with some of the world’s biggest events. It’s also looking at the grassroots level of sports and the startups building its future.

Earlier this year, the USTA launched the inaugural USTA Connect Innovation Challenge, a nationwide open call for tech innovators, engineers and startups to build the next high-impact digital solution for tennis. Selected participants receive access to USTA and U.S. Open data sets to power their prototypes, and a panel that includes USTA representatives, venture capitalists, and an IBM team member evaluates submissions. The top three finalists receive fully funded travel to the USTA Connect event at the 2026 U.S. Open to pitch their ideas, while the grand-prize winner receives $10,000 and exposure across the USTA ecosystem.

More recently, IBM launched the IBM Sports Tech Startup Challenge, which will give founders opportunities to showcase their solutions at Web Summit events in Rio, Vancouver and Lisbon, as well as alongside major tech events including a16z Tech Week in New York and San Francisco. The initiative gives startups a platform to pitch their ideas to audiences at the intersection of sports, technology, and entrepreneurship.

From quietly shaping the fan experience behind the scenes to seeking out the next generation of sports innovators, IBM is proving that even the world’s biggest companies are taking sports seriously. And entrepreneurs should, too.

Many brands use the U.S. Open to entertain clients or put up flashy signage. IBM does both, but its involvement goes much deeper. Behind the scenes, the century-old tech titan is the invisible hand shaping the fan experience, powering the U.S. Open app, and engaging 14 million fans worldwide. In the process, IBM is making the case that sports might be the perfect playground for AI integration.

The servers behind each serve 

From a fan’s perspective, it seems simple. You open the app, check the score and maybe watch a highlight or two. But making that experience work requires IBM and the USTA to process a mountain of data in real time, using AI alongside human review to balance speed and accuracy. One new metric, Serve Quality, analyzes 21 data points across a player’s body and racquet 50 times per second, generating roughly 4.6 million data points per match and more than 1.2 billion throughout the tournament. And then there’s the match chat, an AI bot that lets users ask conversational questions about the sport, like “what is the record for x?” 

Users appear to be embracing these features, if the numbers are any indication: More than 14 million unique devices engaged with U.S. Open digital platforms in 2025, generating nearly 47 million visits, up 19% year over year.

Opinions expressed by Entrepreneur contributors are their own.

It took Emil Barr just 14 months of work to see his first $1 million hit his bank account. He was 19 years old at the time.

Today, at age 23, the founder and CEO, who created two companies while still in school, estimates that his personal net worth is around $35 million. He is unapologetically aiming to be a billionaire by age 30. 

Born in Russia, Barr moved to the U.S. when he was three years old and grew up in a small Ohio town. He stuck out at an early age.

“I was the weird Russian kid that didn’t speak any English,” he tells Entrepreneur. “I think I always felt out of place. And I think that as an entrepreneur, you have to be comfortable with discomfort and that feeling of cutting against the herd.”

In high school, he made his peace with being different and even leaned into it. 

“I’m convinced every high school has at least one weird kid that wears suits to school every day,” he says. “You probably had one. That was me.”

Money, not ambition, first pushed him into entrepreneurship. When it came time to choose a college, Barr enrolled at Miami University, the only college that he could afford. He was looking into transferring to an Ivy League school, but tuition was out of reach. 

“I was like, If money is the limiting factor, how hard can it be to make $100,000 [and] go pay for a year’s tuition?” he says.

How he made his first $1 million

Barr was on the lookout for money-making ideas when he met a classmate with 11 million TikTok followers who was barely earning anything from her social media presence. 

“She got one brand deal for $200,” Barr says. “This is crazy because on Instagram, even if you had a million followers, that would be your full-time career. This was a platform that everyone was using. There was no revenue there yet.”

Barr started his company, Step Up Social, in his freshman year dorm room. His plan was straightforward: Businesses had no idea what to do with TikTok, but Gen Z did. Step Up Social positioned itself as a social media marketing and advertising agency focused on creating short-form video content.

Starting the company required little more than an iPhone and an Internet connection. 

“We grew from $0 to $1 million in revenue in six months,” Barr says of Step Up Social. “As an 18-year-old, I had no idea what I was doing. I never had a corporate internship or anything like that.”

Instead of spending the money, he reinvested in the company’s growth.

“I think the first time I had truly a million dollars in my bank account was 14 months in,” Barr recalls. “It was the start of my sophomore year of college.”

Decisions that led to rapid growth

Growing Step Up Social meant embracing risk, especially debt. When the company adopted 90-day payment terms with large clients, there was a funding gap. Barr had to pay influencers upfront while waiting months for invoices to clear. 

“I was basically running around and taking out as many credit cards and bank loans as I could to keep the company afloat,” he says. “I took out about $1 million worth of personally guaranteed unsecured loans, and everyone thought I was crazy.”

His logic was simple: At 19, he had no assets, so the downside was limited. “If we failed, what were they going to do?” he says. “Were they going to take my shirt or my car? I didn’t have anything to take.”

The third key decision, in his view, was prioritizing people over lifestyle. The “absolute best thing” he spent money on was hiring people with “20 or 30 years of experience,” he says. 

How he grew Step Up Social

Early on, intent on gathering clients, Barr cold-emailed a few hundred companies. The first serious bite came from Kao, a Japanese consumer giant and Procter & Gamble competitor. Barr drove his old, beat-up car an hour and a half to downtown Cincinnati and walked into a 47th-floor boardroom wearing a university T-shirt and shorts. The executives gathered there asked him for his deck.

“I was like, ‘What’s a deck?’” he laughs.

Despite underpricing himself at “$2,000 a month,” he landed the account. That one contract gave Step Up Social credibility and opened doors.

“It was exponentially easier for us to get our next 10 to 15 brands, and it was just off to the races,” Barr says. 

From there, Step Up Social scaled into a full-service TikTok marketing agency, hiring influencers and managing online presences for brands and celebrities. By the time he sold it last year, the firm, by then acquired and rolled into a larger agency, was working with Procter & Gamble, Nike, Nordstrom, Kroger, Alo and Banana Republic.

“We were doing about $2 million a year in revenue, but it was extremely high margins,” Barr says.

Step Up Social earned revenue by connecting brands with creators. For example, a brand might pay the company $600 for a video. The company would then pay the creator $400 to make it and count the remaining $200 as revenue for arranging and managing the deal.

“Gross transaction revenue was closer to $8 to $9 million,” Barr says.

Convincing his university to pay him

Barr didn’t just build a business while attending college; he turned the school itself into a revenue source and marketing machine. He convinced his university to cover his tuition fees. The school also paid him $200,000 and gave him a faculty parking pass. 

Miami University had introduced its entrepreneurship program relatively recently. Barr saw leverage. “I was effectively the only student entrepreneur on campus,” he says. If he dropped out, “they would have no student entrepreneurs. It wouldn’t be a very compelling case study.”

He started with “small asks” like flexible attendance, arguing that it was more important for him to run his company than to participate in group projects. Then, he applied for every grant and pitch competition he could find at the school, winning “$40,000 in a couple of months.”

From there, he reframed himself as both a case study and a vendor. Miami University became a client. Barr’s agency turned the school into “the most-followed public university on TikTok in America,” a result he argues paid back any support many times over.

“For every $1 they spent, whether it was in contracts with us or grants for the business, I’m sure they made at least $10 back in tuition from students who heard of Miami and were drawn to the school,” he says. “So it was probably a good deal for everyone.”

Building Flashpass

Barr’s latest venture, Flashpass, looks very different from a TikTok agency. At its core, Flashpass is his answer to a looming question: What happens to workers if AI replaces 25% to 50% of jobs?

“If we could actually build a way for these 25% to 50% of people who might lose their jobs to be able to quickly get certified online and go find a new job in 30 days, that would be a very valuable service to government as well as to individual users,” Barr explains.

Flashpass is an online platform built around “micro credentials.” Users can learn a new skill in 30 days or less and then be matched with jobs in industries that need talent.

“We have things like natural energy, like oil and gas careers. We have things like medical billing and coding,” he says. “These are all industries where they have a lot of job openings, and they can’t find enough people, and the average pay is over $80,000 a year.”

How Flashpass makes money

The platform doesn’t charge individual users or employers. Instead, Flashpass sells its services to state governments. 

“Typically what we do is we’ll partner with a school, and the government will pay the school, and we will split the revenue with the school,” he says. 

The school helps build curriculum and recruit candidates; the government treats Flashpass as one more education and workforce tool.

“If we could take this Flashpass idea and actually give it to the government and make it free for everyone who loses their jobs as a result of AI, we could build a very valuable business,” Barr says. 

The bet appears to be paying off. Flashpass began with a $4 million, two-year pilot contract in Ohio, with roughly $2 million in annual revenue. Barr says he invested about $75,000 of his own money to build a demo, then used it to land that pilot. Since then, the company has added contracts in Louisiana (about $1 million a year) and Delaware ($2.3 million a year), and has proposals out in 17 states.

“This year, just based on the existing contract volume, we’re set to do at least $8 million, and that’s a four-fold increase over last year,” he says.

Work-life imbalance

Today, Barr estimates his net worth is around $35 million, up from $25 million when he spoke with Business Insider in December. He’s open about the personal cost of becoming a millionaire. In college, his schedule was packed to the minute. He took college classes from 8 a.m. to the early afternoon, then conducted back-to-back calls until 7 p.m. and went to networking dinners. He did his “true work” on the business until 4 a.m., finishing his day with three hours of sleep. 

“I gained 80 pounds,” he says. “I lived off of Red Bull…four or five cans of Red Bull each day.” He skipped holidays and ignored invitations to go out.

He’s since lost 30 pounds and hired a trainer who comes to his house twice a day. The hardest part, he says, is realizing “it’s three times harder to undo the damage than to do the damage initially.”

He also has a personal chef, a home assistant and a driver. Barr still works 19-hour days, but he says he’s calmer and more measured as a leader with the extra help.

One lesson he wishes he’d learned earlier: Don’t spend your 18- to 20-hour days chasing small goals.

“It takes the same amount of effort to do something big as it does to do something small,” he says.

A service business owner usually knows how the work should be done: what a good client interaction sounds like, when an account needs attention, which problems require escalation and where margins can disappear.

That clarity makes the early stages feel manageable. The owner can catch problems, answer questions and keep clients satisfied. But as the business grows, the habits that once held everything together begin to strain.

Ten employees become 30, one market becomes three, and the owner can no longer know what’s happening everywhere. Decisions that once took a quick conversation now require others to have the context and authority to act.

That’s when a surprisingly common problem surfaces: the business has grown, but its systems have not.

I see versions of this throughout franchising. One of the most revealing questions I can ask an operator is not about revenue or customer acquisition. It’s this: “What happens here when you’re not available?”

The answer shows whether the company has translated the owner’s instincts into operating rhythms others can follow, or whether it still depends on informal knowledge passed along one interruption at a time.

If routine decisions stop without the owner, the company may have strong demand and talented people, but it does not yet have a business that can operate independently of the person who built it.

Growth exposes what the owner has been carrying

Small service businesses can run well on institutional knowledge because a few people carry the details that matter.

Someone knows which client needs a call before a schedule change, which employee can handle a difficult assignment, and which account needs an extra quality check.

Scale changes that. More clients, employees, and locations create a greater distance between the person who knows the answer and the person who needs it.

The systems gap appears when knowledge that once lived comfortably inside a few people’s heads needs to become repeatable across an organization.

Documentation is not the same as a system

Owners often respond by creating more procedures, as if a larger binder or longer checklist will automatically create consistency.

A functioning business system should help someone make the right choice, even when the usual decision-maker isn’t standing beside them.

But employees need more than tasks. They need the desired outcome, decision boundaries, and clear escalation points.

I’ve seen this distinction become especially important in commercial cleaning because the work happens across client locations, often outside traditional business hours. A manager cannot physically supervise every team at every facility.

In that environment, the system must operate independently. Ongoing education, quality controls, communication protocols, and accountability must create consistency even when management is miles away.

Technology cannot repair a broken process

Artificial intelligence and automation make this issue more urgent because service businesses now have more tools to speed up scheduling, communication, reporting, and performance management.

Those tools are valuable, but they can tempt leaders to automate before they’ve defined the process they want to improve.

A bad process does not become a good system because software executes it faster. If decisions are unclear, technology simply moves confusion more efficiently.

The sequence matters: clarify the desired outcome, identify inconsistent decisions, and understand why employees improvise. Then technology can reinforce a process that already works.

The CEO test is whether the business needs the CEO

That can be uncomfortable for founders because being needed often feels productive, especially in the early years.

Answering questions feels like leadership. Solving problems feels like service. Stepping in feels like proof the owner is still close to the business.

Over time, however, those strengths can become constraints when every answer still must pass through the same person.

As a CEO, I’ve learned my job is not to answer every operational question. It’s to build an organization that can reach the right answer without me.

Closing the systems gap

Service businesses often chase growth by adding more clients, employees, markets, and technology.

Sometimes the next stage requires something less visible: examining how decisions get made when the owner isn’t in the room.

Every recurring decision that requires the owner may reveal an opportunity to strengthen the system and make growth more durable.

The work often starts by naming the decisions that repeat each week, then deciding who should own them, what information they need, and when they should escalate. That simple discipline turns experience into guidance and gives managers confidence to act before small issues become larger problems.

Revenue and headcount show size. They don’t show whether the business can function without constant direction.

That may be the better test of scale: not just whether the business can grow, but whether it can keep making sound decisions after growth has stretched the founder’s reach.

A service business owner usually knows how the work should be done: what a good client interaction sounds like, when an account needs attention, which problems require escalation and where margins can disappear.

That clarity makes the early stages feel manageable. The owner can catch problems, answer questions and keep clients satisfied. But as the business grows, the habits that once held everything together begin to strain.

Ten employees become 30, one market becomes three, and the owner can no longer know what’s happening everywhere. Decisions that once took a quick conversation now require others to have the context and authority to act.

He helped build the soundtrack of the internet age, turned a scrappy MP3 player into a Yahoo acquisition, sold Beats to Apple and helped launch Apple Music. 

Now, Ian Rogers is betting that the next great consumer platform is not music, but security for your money and identity. He’s building the future from rural Italy as chief human agency officer at the $1.5 billion security startup Ledger.

From Indiana to Apple Music

Rogers grew up in Indiana and discovered computer science in the early 1990s, right as the web took off. “It was a great time to study computer science because when I started, it was sort of like rocket science to people, and then by the end, people were trying AOL,” he tells Entrepreneur. “I was there at the very beginning of the web and made some of the first websites.”

That curiosity quickly collided with music. He dropped out of grad school to go on tour with a band, which took him to California. There, he helped build a popular MP3 player that he sold to AOL in 1999, then another music application that Yahoo acquired. Rogers went on to run Yahoo Music from 2003 to 2008. 

He then built Beats Music and sold it to Apple in 2014. He joined Apple as senior director of Apple Music, overseeing the launch of the music streaming service in 2015. 

Rogers still feels a personal connection to that product. When he met his now-wife, she questioned his loyalty to Apple Music over Spotify. His answer about why he chose Apple Music was simple: “Because I built it.”

Rogers’ time at Apple continues to shape how he thinks about products.

From Apple, Rogers brought a simple, powerful lesson: People buy an ecosystem. “When you buy an iPhone, you’re not buying a piece of hardware,” he says. “You’re buying blue bubbles instead of green bubbles; you’re buying AirDrop; you’re buying FaceTime. That’s part of the experience of being an Apple user versus being an Android user.”

Apple’s genius was creating an integrated experience that “just works,” from the iPod in the early 2000s through to the modern iPhone, Rogers explains. 

After Apple, Rogers moved to Paris to serve as the chief digital officer of LVMH, helping take a traditionally offline luxury group from 3% ecommerce in 2015 to 100% online during the pandemic. 

Why Ledger exists

Nicolas Bacca, Eric Larcheveque and Joel Pobeda founded Ledger in 2014, and Rogers came on board in 2021 as its chief experience officer. Ledger was last valued at $1.5 billion in 2021.

The Paris-based company was founded on a simple premise: The same secure chip technology used in credit cards and passports could be used to protect digital assets. To that end, the startup makes physical hardware crypto wallets that store the digital passwords, known as private keys, needed to access and move cryptocurrency. The devices keep these sensitive keys completely offline, so hackers cannot access them. 

The company’s latest piece of hardware, the $179 NanoGen 5, claims “to protect your assets and identity.” Ledger has sold more than eight million devices.

Today, Rogers’ title is chief human agency officer; he pushed for the change as Ledger doubled down on AI security. “AI security is a top three problem for humanity at the moment,” he says. “What I realized is that that’s not about AI; it’s actually about humans. The job here is keeping humans secure and in control.”

Advice for founders

Rogers says that if he were 25 years old today, he would learn to manage AI agents. 

“We will all become the managers of AI agents,” he says. “The same way that we’re all kind of information peddlers today, we’re having an intelligence revolution that is actually computers taking actions on our behalf.”

In his view, humans will be “end to end” by starting processes and validating results, while agents handle the “middle to middle” work. “Therefore, the same way that we all have computers on our desks today, we will all be having agents on our desks tomorrow,” Rogers says. “And so, if I were 25 years old, I would be building skills at managing agents. Period.”

How do you actually do that? Rogers’ advice is to get your hands dirty with the tools, just as he did with web technologies in the 90s and 2000s.

For founders, his hard-won lesson is about market selection and pain points.

“I think the main thing I’ve gotten wrong in my career is sizing the market relative to my own personal interest,” he admits. “There’s a joke that every college student has a business idea that’s about either music or bars, because that’s what they know.”

What impresses him now are founders who dig deep into pressing, unsexy problems, like logistics and insurance, and uncover real pain. “You find the pain, and then you make a painkiller. You don’t make a painkiller and then go looking for pain,” he says. 

He helped build the soundtrack of the internet age, turned a scrappy MP3 player into a Yahoo acquisition, sold Beats to Apple and helped launch Apple Music. 

Now, Ian Rogers is betting that the next great consumer platform is not music, but security for your money and identity. He’s building the future from rural Italy as chief human agency officer at the $1.5 billion security startup Ledger.

From Indiana to Apple Music

Rogers grew up in Indiana and discovered computer science in the early 1990s, right as the web took off. “It was a great time to study computer science because when I started, it was sort of like rocket science to people, and then by the end, people were trying AOL,” he tells Entrepreneur. “I was there at the very beginning of the web and made some of the first websites.”

Four years ago, one of our clients in her early 30s came to us with $30,000 and a simple ask. She wanted her money working for her without turning into a second career. No inventory to manage, no customer service tickets to answer at midnight and no learning curve on Amazon’s backend. Just a real asset that produced real income, month after month, while she kept living her life.

That’s exactly what a managed storefront was built to do.

The model, in plain terms

At Elite Automation, we don’t sell “ecommerce businesses,” and we don’t do dropshipping in the way most people picture it. What we build is a fully managed, cash-flowing storefront on Amazon’s infrastructure. Our team handles sourcing, fulfillment, pricing and day-to-day account management. The client owns the account, owns the revenue stream and owns the asset. We operate it so she doesn’t have to.

That difference really does matter. It’s the difference between owning a job and owning an asset. A side hustle demands your time, but a managed digital asset demands your capital and then gets out of your way.

What the numbers actually look like

Her store isn’t a fluke or a one-month spike. Pulling from her own profit tracker, here’s what a recent month looked like in April:

• Total sold price: $165,291.14
• Units sold: 3,084
• Net profit: $25,344.03
• ROI: 22.10%

And that wasn’t an outlier. The two months before it told a similar story, with revenue consistently landing in six figures and net profit tracking in the five-figure range each month, ROI holding steady in the high teens to low 20s. This is what four years of consistent operation looks like when the fundamentals are sound and the store is being actively managed by people who do this full time.

That’s the part people underestimate. It’s not one big win — it’s the same disciplined process repeated order after order, month after month, until the compounding becomes obvious on paper.

Why this matters for diversification

Most high-income professionals we work with already have money in real estate, in the stock market and in their own primary business. Those are good things to own. But they’re also correlated in ways people don’t always think about, and none of them are exactly hands off.

A managed Amazon storefront is a different kind of asset. It doesn’t move with the stock market. It doesn’t require you to be a landlord. It doesn’t compete for your time the way your own business does. For our client, it became a genuine fourth pillar, something generating steady monthly cash flow in a lane completely separate from everything else in her portfolio.

That’s the real value of a managed asset. Not that it replaces what you already have, but that it fills a gap none of your other investments can.

Why this should feel encouraging, not out of reach

She didn’t start with a huge war chest. She started with $30,000 and a decision to deploy that capital into something built and operated by people who do this every single day. She never had to become an Amazon expert. She never had to learn fulfillment logistics or supplier negotiations. She just had to trust the process and let it compound.

Four years in, that decision is still paying off, literally, every month.

If you’ve got capital sitting idle and you’re tired of the idea that growing it has to cost you your time, this is what the alternative looks like. Not a side hustle and certainly not another full-time job, but rather a managed digital asset quietly doing its job in the background of a full life.

Diversification isn’t really about chasing more; it’s about not having all of your outcomes tied to the same set of variables. Most people’s version of “diversified” is still just different flavors of the same risk: a primary business that depends on their own time and energy, a stock portfolio that moves with the broader market, maybe a rental property that comes with its own version of a second job.

None of that is wrong, but none of it is actually independent either. True diversification means having at least one asset in your life that doesn’t rise and fall with the same forces as everything else you own, something that isn’t waiting on you to log in, make a call, or put in hours to keep producing. That’s the piece most portfolios are missing: not another version of what they already have, but something genuinely uncorrelated to it.

Four years ago, one of our clients in her early 30s came to us with $30,000 and a simple ask. She wanted her money working for her without turning into a second career. No inventory to manage, no customer service tickets to answer at midnight and no learning curve on Amazon’s backend. Just a real asset that produced real income, month after month, while she kept living her life.

That’s exactly what a managed storefront was built to do.

The model, in plain terms

At Elite Automation, we don’t sell “ecommerce businesses,” and we don’t do dropshipping in the way most people picture it. What we build is a fully managed, cash-flowing storefront on Amazon’s infrastructure. Our team handles sourcing, fulfillment, pricing and day-to-day account management. The client owns the account, owns the revenue stream and owns the asset. We operate it so she doesn’t have to.

I’ve been helping small businesses with their marketing for nearly three decades, and I’ve seen some beautiful websites. But I’ve also encountered a big problem, which is when they don’t convert visitors into prospects and ultimately customers.

There’s nothing wrong with wanting a beautiful website. In fact, a great website should look professional and build confidence. But somewhere along the way, too many businesses mistake looking good for doing its job.

A website isn’t a window dressing. It’s a marketing tool. Every page should help a visitor take the next step in their journey — whether that’s calling your office, requesting a quote, scheduling an appointment, making a purchase or simply learning enough to trust you.

If you want your website to generate more customers, here are three places to start.

1. Build your website to get leads and business — not for design awards

A person forms an impression about your website in just 50 milliseconds! Of course we want the website to be aesthetically pleasing, but what’s even more important is the customer’s journey.

When someone lands on your homepage, they should immediately understand:

• What you sell
• How your product or service benefits them
• What they should do next

Some of the biggest conversion killers prioritize design over usability, clever messaging instead of clear instructions and fluffy content instead of key information. Ideally, every element on your website works towards communicating one of these three purposes.

Trust and affinity builders:

When people land in an unfamiliar place like your website, there’s a slight barrier of distrust that comes up — and it’s your job to overcome that so they feel safe browsing your website and will stick around.

One way to build trust is through familiarity. Here are a few tactics:

• Place website navigation tools in expected places (don’t you hate when you want to go somewhere on a site and you can’t find the button or link?).
• Include trust signals like professional credentials and certifications, Google reviews, success stories and real photos of your staff, products/services and operations (not stock photos).
• Build on the trust by positioning yourself or your company as the expert in the space. You can do this by educating prospects on all aspects of your product or service so they consider you and your brand helpful.
•  Include strong calls to action that tell people exactly what to do next. On your website, this can be filling out a form, calling a phone number, sending an email or downloading a report. Make sure you keep it direct and clear so it’s as easy as possible for people to turn their interest into action. The call to action should give you minimally their email address so that you can follow up!

Your website exists to remove barriers to the sale, not add more. Take every opportunity to avoid a misstep in the customer journey. Provide as much useful information and calls to action as possible to make your purpose and direction clear.

2. Bring web visitors back with digital retargeting

If a person visits your website and leaves immediately without interacting with other pages or taking an action, this is called a “bounce” — and unfortunately it’s very common. The average bounce rate is 44% across all industries.

A bounce doesn’t mean they’re gone forever, though. In fact, returning visitors make up 50% of website traffic, and there are tools at your disposal to bring people back faster.

By placing a small piece of tracking code on your website, you can target anonymous visitors with digital ads after they leave. Depending on the network you choose, your digital ads will appear through Google’s Display Network, Meta or other online advertising channels while those prospects browse the internet.

This is called digital retargeting, and you’ve likely already seen ads like this following you around. Instead of disappearing after one website visit, your business stays visible.

We can never be sure what made someone leave in the first place. What we do know is that retargeting ads will help bring them back — about 76% of consumers are more likely to convert after being retargeted by digital ads.

3. Link up your website to the mailbox

Online ads are great at generating spur-of-the-moment clicks. But what happens when someone visits your website, looks around and leaves without taking action?

That’s where direct mail retargeting comes in. Direct mail retargeting works much like digital retargeting. Instead of serving another online ad to past website visitors, it automatically sends a pre-designed postcard to their mailbox immediately, usually within 24 hours.

The process is surprisingly simple. A small tracking pixel is added to your website, much like the ones used for Google or Facebook advertising. When an anonymous visitor leaves without converting, the system matches available mailing addresses and automatically triggers a postcard to be printed and mailed.

Instead of competing with dozens of browser tabs, social media posts, emails and digital ads, your message arrives somewhere far less crowded: the mailbox. Recent research found that 84% of consumers read direct mail the same day they receive it.

If you run an ecommerce business, you can take the same approach with abandoned shopping carts. When someone adds products to their cart but leaves before checking out, an automated postcard can remind them what they left behind and encourage them to complete the purchase.

Getting started is easier than many business owners realize. Several direct mail providers now offer website retargeting platforms that integrate with your website, allowing postcards to be triggered automatically based on visitor behavior — just like your digital retargeting campaigns.

So do you want compliments or dollar signs? Focus on a website that converts and builds customer loyalty, and your business will grow more than a flashy reputation.

I’ve been helping small businesses with their marketing for nearly three decades, and I’ve seen some beautiful websites. But I’ve also encountered a big problem, which is when they don’t convert visitors into prospects and ultimately customers.

There’s nothing wrong with wanting a beautiful website. In fact, a great website should look professional and build confidence. But somewhere along the way, too many businesses mistake looking good for doing its job.

A website isn’t a window dressing. It’s a marketing tool. Every page should help a visitor take the next step in their journey — whether that’s calling your office, requesting a quote, scheduling an appointment, making a purchase or simply learning enough to trust you.

For years, community colleges were seen as the overlooked corner of American higher education. They lost millions of students during the pandemic, faced questions about declining enrollment, and often sat in the shadow of four-year universities. They were hit harder by the pandemic, with fall 2020 enrollment dropping 10% compared to the prior year, the steepest decline on record for public two-year institutions, according to the NCES data.

But that narrative is changing. Community colleges are now leading one of the strongest enrollment recoveries in U.S. higher education, driven by a shift in what students value most: affordability, faster pathways to employment, and education that delivers measurable career outcomes.

From pandemic decline to enrollment revival

A 2023 Community College Research Center (CCRC) study at Columbia University found that between fall 2019 and fall 2021, community colleges enrolled 586,000 fewer students aged 18 to 24, compared with a decline of 277,000 students aged 25 and older. More importantly, those students did not simply shift to four-year universities. Enrollment among 18- to 24-year-olds at four-year institutions also declined by roughly 200,000 students during the same period. 

The numbers back up that shift. According to the National Student Clearinghouse Research Center’s Spring 2026 Enrollment Trends report, community colleges enrolled 5.8 million students in spring 2026, representing a 5.2% increase compared with spring 2021. The momentum has been building across academic terms.

In fall 2025, community college enrollment grew 3.0% year over year, outperforming several other higher education sectors and reinforcing that the recovery is becoming a sustained trend rather than a temporary rebound.

The comeback isn’t happening because students have suddenly abandoned four-year degrees. Instead, economic realities are reshaping enrollment decisions. Rising tuition costs, employer demand for job-ready skills, the growing popularity of short-term certificates and the return of adult learners are making community colleges an increasingly practical choice. Many institutions have also expanded workforce partnerships, improved transfer pathways and modernized student support, making it easier for learners to move from the classroom into high-demand careers.

Together, these forces are turning community colleges into something more than an affordable alternative. They are becoming a critical part of America’s workforce pipeline and a window into how higher education is evolving.

Students are increasingly choosing career-focused programs

One reason community colleges are having a moment is pretty straightforward: students want to know where their education can take them. Instead of spending four years on a degree with an uncertain payoff, many are looking for programs that help them build practical skills, earn a credential and move into a career faster. Community colleges are well-positioned for this, with certificates, associate degrees, technical programs and other shorter pathways designed around workforce needs.

A Strada Education Foundation study shows just how much career goals matter to community college students. Among recently surveyed community college students, 74% said gaining skills to be successful at work was an important reason for enrolling. Another 69% said advancing their careers and making more money were important motivations. In other words, students aren’t just asking, “What can I study?” They’re increasingly asking, “What will this help me do?”

The enrollment numbers tell a similar story. According to the National Student Clearinghouse Research Center, community college enrollment grew 5.4%, or 288,000 students, in spring 2025. Vocational-focused public two-year colleges saw particularly strong growth, with enrollment nearly 20% higher than it was in spring 2020. That suggests the community college comeback isn’t simply about students returning to college. It’s also about students gravitating toward education with a clearer connection to the workplace.

Affordability matters

There’s another reason community colleges are becoming more attractive: they make the financial equation easier for many students to manage. According to the Strada 2025 study, 77% of respondents found college to be unaffordable. 

Affordability is also about more than sticker price. Community colleges offer students access to a range of financial support, from scholarships and grants to emergency aid. Research from New America found that nearly 80% of new and continuing community college students said their institution offered financial aid, while more than half reported actually receiving it. 

A 2024 Lumina Foundation–Gallup survey of current, former and prospective college students found that 53% considered financial aid or scholarships very important to their decision to enroll or remain enrolled. The same share said confidence in the value of their degree or credential was very important. And for half of the students, the prospect of increasing their personal income was also a very important factor.

That cost-conscious mindset gives community colleges an obvious advantage. They have traditionally offered a lower-cost route into higher education, while also giving students the option to earn a credential, enter the workforce or transfer to a four-year institution. For students trying to make every education dollar count, that combination is hard to ignore.

Short-term credentials are becoming more attractive

Not every student wants to spend four years earning a degree before stepping into the workforce. More students are looking for a faster way to build practical skills, earn a recognized credential and start creating career momentum. That shift is making certificates, micro-credentials and other short-term programs increasingly appealing.

The interest is already there. Tyton Partners’ Listening to Learners 2025 found that nearly 90% of students expressed at least some interest in non-degree credentials, including certificates, micro-credentials, industry certifications and digital badges. Among community college students, 40% said they were very interested, while another 48% said they were somewhat interested.

The research backs up the trend. The Economics of Education Review 2025 study found that short-term certificates are the fastest-growing type of postsecondary credential in the United States. The study also found that certificates requiring less than a year to complete have grown by about 60% over the past two decades, highlighting the growing appeal of shorter pathways that can lead to employment more quickly.

For years, community colleges were seen as the overlooked corner of American higher education. They lost millions of students during the pandemic, faced questions about declining enrollment, and often sat in the shadow of four-year universities. They were hit harder by the pandemic, with fall 2020 enrollment dropping 10% compared to the prior year, the steepest decline on record for public two-year institutions, according to the NCES data.

But that narrative is changing. Community colleges are now leading one of the strongest enrollment recoveries in U.S. higher education, driven by a shift in what students value most: affordability, faster pathways to employment, and education that delivers measurable career outcomes.

From pandemic decline to enrollment revival

A 2023 Community College Research Center (CCRC) study at Columbia University found that between fall 2019 and fall 2021, community colleges enrolled 586,000 fewer students aged 18 to 24, compared with a decline of 277,000 students aged 25 and older. More importantly, those students did not simply shift to four-year universities. Enrollment among 18- to 24-year-olds at four-year institutions also declined by roughly 200,000 students during the same period.