August 2026

Forty thousand dollars is a lot to wait on when you’re running a small restaurant. But that’s exactly what happened to Joy Kim, who spent eight months chasing down money Uber Eats owed her.

Kim, who owns Kyoto Teriyaki on Seattle’s Capitol Hill, had been waiting since November 2025 for the company to pay out nearly 1,500 orders, according to Fox 13 Seattle. She called support, sent emails, updated her bank information. Nothing worked.

It wasn’t until Fox 13 Seattle began inquiring about the missing funds that Uber Eats moved. Uber Eats said the delay came down to identity verification required to protect the merchant account, and that representatives made multiple attempts to reach Kim without success. The company said it completed video verification with her in late July and began processing the payment shortly after.

Despite the ordeal, Kim plans to keep using the platform. Local customers order through Uber Eats every day, she said, and cutting it off would mean losing a revenue stream she can’t afford to lose.

Forty thousand dollars is a lot to wait on when you’re running a small restaurant. But that’s exactly what happened to Joy Kim, who spent eight months chasing down money Uber Eats owed her.

Kim, who owns Kyoto Teriyaki on Seattle’s Capitol Hill, had been waiting since November 2025 for the company to pay out nearly 1,500 orders, according to Fox 13 Seattle. She called support, sent emails, updated her bank information. Nothing worked.

It wasn’t until Fox 13 Seattle began inquiring about the missing funds that Uber Eats moved. Uber Eats said the delay came down to identity verification required to protect the merchant account, and that representatives made multiple attempts to reach Kim without success. The company said it completed video verification with her in late July and began processing the payment shortly after.

Despite the ordeal, Kim plans to keep using the platform. Local customers order through Uber Eats every day, she said, and cutting it off would mean losing a revenue stream she can’t afford to lose.

It may be stalled growth, a customer segment that is not converting or a team issue that keeps resurfacing.

Every business owner has a problem they know they need to address.

To really solve the problem, business owners need dedicated time to focus, honest feedback from people who understand the stakes and a structured way to turn a broad source of frustration into a decision and a plan.

That’s why we teamed up with Robert Irvine — the celebrity chef who has helped hundreds of struggling business owners on his show “Restaurant: Impossible” — to put together Overcoming Impossible Live, a one-day Entrepreneur Level Up event taking place on October 23, 2026, at 1 Hotel Brooklyn Bridge in New York City.

This is not a traditional business conference built around back-to-back keynote presentations. It is a working session for founders and business owners like you who are ready to confront the specific issue holding their company back — and solve it.

Solve Your Biggest Business Challenge

At Overcoming Impossible Live, attendees will identify the “impossible” issue holding their business back, then work through it in structured small groups alongside founders facing similar business problems.

This is not a generic networking exercise. The goal is to put entrepreneurs in a room with peers who understand the same kind of pressure, whether that is a growth problem, leadership challenge, operational issue or difficult strategic choice.

Robert Irvine and Entrepreneur Editor in Chief Jason Feifer will coach attendees through the workshop experience. The goal is to help you leave with:

• Clarity on the problem you need to solve
• Feedback from founders facing comparable business challenges
• A concrete action plan for when you return to work

Hear Real Business Lessons

The afternoon will bring together three entrepreneurs who have built, rebuilt and made difficult decisions at scale.

Robert Irvine will be joined by Gary Vaynerchuk and Megan Thee Stallion, who will each share an honest story about a moment when they were stuck—what happened, what it cost and the steps they took to help them move forward.

Gary Vaynerchuk will deliver his “State of the Union on Attention,” while Megan Thee Stallion will share lessons on overcoming the odds and owning difficult decisions.

Ask the Questions That Matter

Overcoming Impossible Live also creates space for entrepreneurs to ask direct questions about their own businesses.

That distinction matters. The value this exclusive event provides is to use the room to pressure-test your own situation, hear candid perspectives and leave better equipped to act.

If there is a problem you have been working around instead of working on, this is the day to put it all on the table.

Register for Overcoming Impossible Live

It may be stalled growth, a customer segment that is not converting or a team issue that keeps resurfacing.

Every business owner has a problem they know they need to address.

To really solve the problem, business owners need dedicated time to focus, honest feedback from people who understand the stakes and a structured way to turn a broad source of frustration into a decision and a plan.

Founders are often taught to move quickly, listen to feedback and keep improving. That advice is useful, but it can also create a trap. When a product or business model starts to struggle, many entrepreneurs immediately look for ways to refine the solution. They add a feature. They adjust the messaging. They change the packaging, pricing or sales process.

Sometimes that works. Other times it only makes the business more complicated. I have learned that one of the most important questions a founder can ask is not “How do we make this better?” It is “Are we still solving the right problem?”

That question matters because markets do not stand still. Economic pressure changes buying behavior. What felt urgent to customers at one stage of the business may feel less relevant six months later. A product that once solved a clear need can slowly drift away from the problem it was created to address.

This is especially important for founders building in health, wellness, consumer products or any category where trust, behavior and daily routines matter. Customers may not always be able to explain what they need in a survey or review. But they will show it through what they buy, repeat, abandon and recommend.

Research from McKinsey has found that organizations that leverage customer behavioral insights outperform their peers by 85% in sales growth and more than 25% in gross margin. For founders, the takeaway is simple: strategy should not be built only around what customers say. It should also be built around what they do.

Reassess the problem before refining the solution

Founders can become attached to their original idea because they remember the energy that gave rise to it. They remember the pain point, the early conversations and the first signs of traction. But early validation is not permanent validation.

The more a company grows, the more dangerous assumptions become. A founder may think the problem is still convenience, when the customer now cares more about trust. They may think the challenge is price, when the real barrier is confusion. They may think the market wants more options, when customers are actually asking for a clearer path.

Before refining a product, founders should pause and define the current problem as clearly as possible. What is the customer trying to solve today? What has changed in the market? What pressure is the customer feeling now that they were not feeling before?

In my own work across consumer and wellness brands, this reassessment has been essential. A product may begin with one promise, but the customer’s relationship with that product can reveal something deeper. They may not only want a supplement, a skincare product or a wellness solution. They may want simplicity, confidence, consistency or a better way to make daily choices that support their lives.

When my team understands that deeper problem, improvement becomes more focused. The goal is no longer to add more. It is to solve more precisely.

Let behavior lead your strategy

Customer feedback matters, but it is not the whole story. Customers can tell you what they think they want. Their behavior tells you what they truly value.

That is why founders should pay close attention to purchasing patterns, repeat usage, drop-off points, engagement signals and the moments when customers hesitate. These signals reveal where your business is aligned and where it is creating friction.

If customers consistently purchase one product but ignore a bundle, the issue may not be awareness — the bundle may be too confusing. If customers engage heavily with educational content but hesitate to buy, the product may need clearer proof or simpler positioning. If customers buy once but do not return, the problem may be experience, expectation or follow-through.

I have learned to separate preference from behavior. A customer may say they want more choices, but too many choices can create decision fatigue. A customer may say they want innovation, but what they actually reward is reliability. A customer may praise a brand’s mission, but only buy when the offer feels clear and useful.

Real-world action is one of the most honest forms of feedback. The founder’s job is to notice it without defensiveness.

Simplify before you scale

When growth slows, many companies respond by adding. They add more products, more features, more campaigns and more explanations. The intention is usually good. The result is often confusion.

Complexity can make a business feel more sophisticated internally while making it harder for customers to understand externally. In their influential Harvard Business Review study on “feature fatigue,” Roland Rust and colleagues found that consumers routinely pick feature-rich products at the moment of purchase, then abandon them once they discover the complexity gets in the way of actually using them. The lesson for founders is unambiguous: more is not the same as better.

Founders should ask hard questions before scaling. Is the offer clear enough to grow? Can people quickly understand what the product does? Can they see who it is for? Can they explain the value in their own words? Can they buy, use and recommend it without needing excessive explanation? Answering those questions requires looking at the entire customer journey.

Simplicity does not mean reducing ambition. It means removing anything that distracts from the core value. In many cases, scaling becomes easier when the offer is narrower, the message is cleaner and the experience is more intuitive.

Build reassessment into the business

Product-market fit is not a finish line. It is a relationship between the company, the customer and the market — and like any relationship, it requires continued attention.

Founders should create systems that make reassessment part of the business rhythm. That may include regular reviews of customer behavior, cross-functional conversations between product and marketing teams, post-purchase analysis, customer service insights and market trend reviews.

The key is not to collect more data for its own sake. The key is to turn feedback into decisions. What should be simplified? What should be removed? What should be tested? What needs to be explained differently? What assumption is no longer true?

This process also requires humility. Founders must be willing to admit that a product can be good and still need to change. A strategy can be smart and still need to evolve. A market can validate an idea once and still demand something different later.

The founders who build lasting companies are not only the ones who move fast. They are the ones who stay close enough to the customer to know when to pause, reassess and redirect.

Growth is not always about building the next version of the solution. Sometimes it is about returning to the problem with fresh eyes. When founders make that a habit, they give their companies a better chance to stay relevant, useful and resilient as the market changes.

Founders are often taught to move quickly, listen to feedback and keep improving. That advice is useful, but it can also create a trap. When a product or business model starts to struggle, many entrepreneurs immediately look for ways to refine the solution. They add a feature. They adjust the messaging. They change the packaging, pricing or sales process.

Sometimes that works. Other times it only makes the business more complicated. I have learned that one of the most important questions a founder can ask is not “How do we make this better?” It is “Are we still solving the right problem?”

That question matters because markets do not stand still. Economic pressure changes buying behavior. What felt urgent to customers at one stage of the business may feel less relevant six months later. A product that once solved a clear need can slowly drift away from the problem it was created to address.

Most people assume successful businesses start with a detailed plan or a big idea. In my case, both companies I founded began with little more than a willingness to act.

Years spent helping companies grow through strategy, content and customer acquisition taught me a lot, but eventually I hit a ceiling. My first business had run its course. The real value was in what it revealed: bigger opportunities waiting beyond my current work. So I sold my company and started over.

The path forward was anything but linear. Mistakes, hard lessons, international travel and personal investment shaped every phase. Each decision, good or bad, pushed me closer to launching a biodegradable startup.

During the Covid years, I spent nearly four years in Uttarakhand working closely with farmers and rural communities across different regions. Working alongside farmers gave me a ground-level view of challenges and surfaced opportunities that rarely show up in market reports.

Transitioning from idea to reality, I realized building a sustainable business is a different game from launching a conventional startup. Timelines stretch, challenges multiply, and results take longer to materialize. But when progress comes, it tends to last. Each phase surfaced lessons that still shape how I approach decisions today.

1. Spend time in the field

One of my biggest lessons came from working in the hemp industry. It looked easy to source hemp because it was widely available. But in practice, scaling up was much more complicated.

There were regulatory hurdles, unclear land titles and tough terrain that made operations difficult. I wouldn’t have known about these problems from reports or research alone. I learned about them by living and working in those areas.

This experience showed me that opportunities are rarely limited by demand. Instead, they are often held back by challenges you only see when you’re actually there. If you want to build something that lasts, spend time where the problems are real. Firsthand exposure reveals challenges and opportunities that rarely show up from a distance.

2. Be ready to change direction

One of the hardest decisions I made was selling my first business. Entrepreneurs hear a lot about persistence, but self-awareness matters just as much. Sometimes the right move is to step back and ask whether your current path still aligns with your long-term goals.

For me, the business served its purpose. It gave me experience, industry knowledge, relationships and a better understanding of sustainability.

3. Think global, act local

As I continued exploring opportunities in sustainability, I traveled to China and Australia to better understand how other markets were approaching innovation, manufacturing and the environment. Travel forced me to rethink how I approached challenges and opportunities. That shift in perspective is often what drives sustainable growth.

In China, I saw how industries can scale rapidly when infrastructure, manufacturing capabilities and market demand align. In Australia, I saw a strong emphasis on sustainability and long-term environmental thinking.

Opportunities often appear in one market years before they show up in others. Most founders focus on local competition, but the real edge comes from spotting global trends before they hit your own market.

Travel doesn’t always give you answers, but it does give you perspective. And having perspective helps you make better decisions.

4. Build credibility before visibility

People often ask me how I managed to grow my business without spending money on ads. The answer is simple: I focused on building credibility before trying to get noticed.

It’s tempting to think growth only comes from bigger marketing budgets. Advertising can buy attention but not trust. Focus on building relationships, understanding the industry, educating stakeholders and creating genuine value.

While founding Ukhi, the materials science deep tech startup I started, I focused on building genuine content authority through original research studies and high-quality blog posts, all intended to help our customers. Now, this strategy is paying off.

This approach took patience. Building credibility is slow, but the payoff lasts longer than any quick win from advertising.

Business growth came slower, but it stuck. People engaged because they trusted us. We did not run ad campaigns at all. And increased trust led to referrals, partnerships and opportunities that money rarely buys.

Credibility compounds

One of the most valuable lessons I learned is that credibility compounds. Advertising stops when the budget runs out, but trust keeps working long after. Look at successful businesses; they often focus on outcomes. They see growth, funding, partnerships or market traction.

What rarely gets noticed are the years spent learning, making mistakes and investing before results show up.

Those early stages are what make sustainable success possible. For me, it evolved through years of working with farmers, expanded through international exposure and continues today through new ventures and ongoing investment in sustainability.

If there’s one lesson for aspiring entrepreneurs, it’s that clarity almost never comes before action. Most of the opportunities that shaped my career only showed up after I took the first step.

The path was rarely clear or easy, but every lesson and mistake helped me better understand my impact. That, more than any business plan, is what helped me build a sustainable business from nothing.

Most people assume successful businesses start with a detailed plan or a big idea. In my case, both companies I founded began with little more than a willingness to act.

Years spent helping companies grow through strategy, content and customer acquisition taught me a lot, but eventually I hit a ceiling. My first business had run its course. The real value was in what it revealed: bigger opportunities waiting beyond my current work. So I sold my company and started over.

The path forward was anything but linear. Mistakes, hard lessons, international travel and personal investment shaped every phase. Each decision, good or bad, pushed me closer to launching a biodegradable startup.

Mark Zuckerberg published a 6,500-word essay this week laying out his vision for artificial intelligence. The timing isn’t random. Meta is lagging behind in the AI race and trying to catch up to rivals like Anthropic and OpenAI, according to the Wall Street Journal. It also comes as investors grow impatient with Meta’s AI spending, after the company’s free cash flow recently collapsed.

Here’s the gist of his argument. Zuckerberg wants AI to stay open, meaning anyone can download and build on Meta’s models, rather than locked inside a few giant companies. He’s argued before that concentrating AI power is dangerous and believes open access creates more jobs. He also wants the government working more closely with AI labs before models launch, rather than a fixed review period. And he’s giving Meta’s own board more say over what counts as safe.

Perhaps to fend off local opposition to data centers, Zuck also offered a new $1 billion fund for communities near Meta’s data centers.

Mark Zuckerberg published a 6,500-word essay this week laying out his vision for artificial intelligence. The timing isn’t random. Meta is lagging behind in the AI race and trying to catch up to rivals like Anthropic and OpenAI, according to the Wall Street Journal. It also comes as investors grow impatient with Meta’s AI spending, after the company’s free cash flow recently collapsed.

Here’s the gist of his argument. Zuckerberg wants AI to stay open, meaning anyone can download and build on Meta’s models, rather than locked inside a few giant companies. He’s argued before that concentrating AI power is dangerous and believes open access creates more jobs. He also wants the government working more closely with AI labs before models launch, rather than a fixed review period. And he’s giving Meta’s own board more say over what counts as safe.

Perhaps to fend off local opposition to data centers, Zuck also offered a new $1 billion fund for communities near Meta’s data centers.

Most companies don’t break all at once. They crack in predictable places, but founders often don’t look there until something forces them to.

I went through this cycle at UNest, the fintech company I founded to help families invest for their children’s future. On paper, we were growing, raising capital and building a product customers wanted. But underneath, there were risks we hadn’t fully pressure-tested. When the environment changed, those risks surfaced quickly.

If you want to understand how resilient your business actually is, you don’t need a complex framework. You need to test four things: your cash, your dependencies, your level of control and your ability to make decisions under pressure.

1. Start with cash: Model the version of reality you don’t want

Most founders track runway based on current burn and expected growth. That’s useful, but it doesn’t tell you how the business behaves under stress. The faster way to see the truth is to model scenarios that break your assumptions.

Take your current numbers and run three variations. First, assume revenue drops by 30%. Second, assume your costs increase by 20%, which happens more often than people expect when something shifts in the market. Third, assume you cannot raise capital for six to 12 months. Then look at what happens.

How many months of runway do you actually have in each case? How much of your cost base is fixed versus variable? If you needed to reduce burn by 30% to 50%, how long would that take, and what would be the impact? I’ve seen founders realize that what looked like 12 months of runway turns into five very quickly.

External shocks are a real possibility you must insulate yourself from. A platform like Meta can change priorities overnight. A new AI feature can replace part of your product. Shipping costs can spike unexpectedly, as many companies experienced during COVID. If your model only works when everything goes right, you’re doing it wrong.

2. Map dependencies like they’re risk, not strategy

Most startups have a hidden single point of failure. It might be a partner, a distribution channel or even one person on the team.

At UNest, we leaned heavily on third-party infrastructure early on. It helped us move faster and conserve cash, which looked like a smart trade-off. What I didn’t fully appreciate was how much control we were giving up. We started seeing it in small ways — onboarding flows in our app depended on external processes, and what should have taken minutes required manual work, workarounds and sometimes even physical paperwork. That friction compounds, and over time, it becomes an operational risk.

To make this visible, you need to map dependencies explicitly. List out your top dependencies across three areas: how you acquire customers, how your product actually works behind the scenes and where your capital comes from. Then test each one.

You’ll start to see patterns. Some dependencies are painful but manageable, while others are existential. The ones that fall into the second category are the ones you need to fix or diversify. When infrastructure providers shut down, they can take down entire ecosystems.

3. Can you even make the decision you want?

Most founders assume they are in control of their company. That assumption usually holds until the first real downturn. The question to ask is straightforward: If things start breaking, do you actually have the full authority and support to change direction?

Start with your cap table and board structure. If one investor has blocking rights over financing, strategy or exits, that will shape what options are realistically available to you. The same is true if multiple board members are tied to the same fund or aligned incentives. On paper, it may look balanced. In practice, it can concentrate control.

You also need to understand where approvals are required. Can you reduce burn, pivot the product or change strategy without board approval? Or do those decisions require alignment across multiple stakeholders?

This becomes critical in a downturn. I’ve seen situations where founders wanted to pivot and keep building, while investors pushed to shut the company down and have capital returned. That outcome was determined by how control was structured from the beginning. You don’t want to discover these constraints when you’re already under pressure — by then, your options are limited to what the structure allows.

4. Even if you can decide, can your team execute quickly?

Having the authority to make decisions is only part of the equation. The next question is whether your company can act on those decisions fast enough.

In most startups, execution slows down under pressure — not because people aren’t capable, but because the system isn’t designed for speed. The breakdown usually happens in predictable ways: teams spend too much time analyzing instead of acting, decisions get reopened instead of executed and ownership is unclear so work stalls even after alignment.

You can test this directly without waiting for a real crisis. Take a realistic scenario and run it as a working session. For example, assume your primary acquisition channel doubles in cost overnight, or a key partner shuts down. Then walk through what actually happens.

Pay attention to how the team responds. If it takes too long to reach decisions, or if no one clearly owns the next steps, that’s where your system will fail under real pressure. In a downturn, speed is not just helpful — it determines whether you have the time and ability to recover.

Don’t ignore the founder side of the stress test

There is one more variable in all of this, and it’s the founder. In every difficult moment I’ve gone through, the hardest part was not identifying the problem. It was making decisions quickly without complete information and standing behind them. You should pressure-test that as well.

Are you ready to make decisions that will be unpopular internally or with your investors? Can you keep operating when you don’t have clear answers? Do you have the resilience to lead through uncertainty?

At some point, every founder hits a roadblock. The question is whether you’ve already examined your own reactions and performed this stress test before it happens. Because in a downturn, your judgment, your speed and your willingness to act become the system the company runs on.

Most companies don’t break all at once. They crack in predictable places, but founders often don’t look there until something forces them to.

I went through this cycle at UNest, the fintech company I founded to help families invest for their children’s future. On paper, we were growing, raising capital and building a product customers wanted. But underneath, there were risks we hadn’t fully pressure-tested. When the environment changed, those risks surfaced quickly.

If you want to understand how resilient your business actually is, you don’t need a complex framework. You need to test four things: your cash, your dependencies, your level of control and your ability to make decisions under pressure.

Founders are often celebrated for their ability to do everything. In the early stages of a company, that closeness can feel necessary. You are close to the product, the brand, the customers, the operations and the decisions that keep the business moving.

That involvement can be powerful. It helps you understand the details, respond quickly and protect the vision while the company is still taking shape. But there is a point in every growing business when the same instincts that helped you build the company begin to limit it.

If every decision still depends on you, the company cannot move faster than your personal capacity. If every department relies on your direct involvement, growth becomes exhausting instead of expansive. The business may be getting bigger, but your leadership model is still built for the earliest stage.

The pattern is well-documented. When Harvard Business School professor Noam Wasserman analyzed more than 200 U.S. startups, he found that by the time the ventures were three years old, 50% of founders were no longer the CEO. Most did not step down willingly. The founders who lasted were the ones who evolved before the board decided the company had outgrown them.

I have experienced this shift across multiple companies and ventures. As my responsibilities expanded, I had to recognize that my role could not remain the same. The business needed more than my ideas, urgency and energy. It needed strategic leadership, stronger systems and trusted people who could carry the mission with consistency.

The goal is not to stop thinking like a founder. It is to become the kind of CEO your growing company now requires.

Shift from doing to directing

In the beginning, founders are involved in everything because they have to be. You may be making decisions about product one hour and customer experience the next, reviewing finances, refining messaging and solving operational problems all in the same day.

That level of involvement gives you valuable insight. It also creates a habit of being the person who answers every question and fixes every problem.

As the company grows, that habit becomes risky. The organization starts waiting for you instead of moving through clear systems. Team members hesitate to take ownership because they are used to you stepping in. What once created speed eventually creates a bottleneck.

One of the hardest parts of my own transition was learning to release direct control without releasing accountability. Those are not the same thing. Letting go does not mean becoming disconnected from the business. It means building the conditions for other leaders to make strong decisions without needing constant approval.

A practical way to begin: Identify which decisions truly require the CEO and which should live elsewhere in the organization. If everything is treated as mission-critical, nothing is. Founders have to learn to separate high-impact strategic decisions from daily operational choices capable leaders can own.

Build leaders before you need them

A company cannot scale on the founder’s passion alone. Growth requires people who understand the vision, take ownership and make decisions that strengthen the whole organization.

When I think about leadership, I look beyond technical ability. Expertise matters, but so do integrity, accountability, adaptability and communication. A leader who is highly skilled but disconnected from the mission can create progress that looks efficient in the short term but becomes misaligned over time.

This is especially vital in mission-driven work. As my own ventures have grown across wellness, science, sustainability and consumer products, alignment has been just as important as execution. Different brands may have different audiences, but the larger purpose still has to be clear.

Founders should not wait until they are overwhelmed to build leadership capacity. By then, delegation feels rushed and reactive. Start developing leaders while the company is still small enough for people to learn the business deeply.

Give emerging leaders clear expectations. Define what they own. Explain what success looks like. Create enough structure that people can act confidently, and enough accountability that quality does not depend on the founder watching every detail.

Trust is not built through vague encouragement. It is built through clarity.

Protect time for the work only you can do

The founder-to-CEO transition often shows up first on the calendar.

In the early stage, a founder’s schedule is full of immediate needs. That works for a while because the company is still forming and speed is necessary. But as the organization grows, a reactive calendar becomes a reactive leadership style.

The CEO’s time has to reflect the company’s highest priorities — strategic planning, partnerships, innovation, leadership development, long-term decision-making. It also means recognizing that being busy is not the same as being effective.

This is difficult for founders used to being accessible to everyone. I often felt guilty stepping away from daily tasks or declining meetings that once felt important. But if your calendar does not create space for strategic thought, your business will keep moving without enough direction.

One exercise that has helped me: regularly reviewing where my time is going and asking whether it matches the role the company needs me to play now — not the role I played three years ago, and not the role I played when the company was smaller.

A CEO’s most impactful work is not always the most visible work. Sometimes it is the quiet planning, the difficult prioritization and the disciplined decision-making that keep the company moving in the right direction.

Communicate with more structure

In a small company, communication happens naturally. People hear conversations, understand priorities and absorb decisions because everyone is close to the founder. That changes as the team expands.

As more people join the organization, communication has to become more structured. Founders cannot assume that everyone understands the vision simply because it feels obvious to them. Priorities need to be repeated. Decisions need context. Expectations need to be clear enough that people can act without guessing.

This is one of the most underestimated parts of becoming a CEO. The message that feels repetitive to you is the message your team needs to hear again. Consistency creates alignment. Alignment creates better execution.

Strong communication also reduces confusion during growth. When teams do not understand what matters most, they work hard in different directions — which creates frustration, slows decision-making and weakens the culture.

A CEO’s communication should help people understand where the company is going, why and how their work contributes. It does not require long speeches or constant meetings. It requires clarity, consistency and the discipline to reinforce what matters most.

Stay close to the mission

One risk of growth is distance. As the company becomes more complex, founders can become removed from the original purpose that inspired the work. More systems, meetings and layers of leadership create space between the CEO and the people the company serves.

That distance is dangerous, because your mission is not just a brand statement — it is a decision-making filter. For me, staying grounded means regularly reconnecting with the people impacted by the work, the problems we are trying to solve and the purpose behind the companies we are building. Growth introduces complexity, but a mission helps simplify the most important choices.

When a company is small, the mission lives inside the founder. As the company grows, the mission has to live inside the organization. It has to shape hiring, product decisions, partnerships, communication and culture. That only happens when the CEO protects it intentionally.

Grow with your business

The transition from founder to CEO is not a single milestone. It is an ongoing process of self-awareness, adaptation and leadership development. At some point, every founder has to ask a hard question: am I leading the company that exists today, or am I still leading the company I started years ago?

That question can be uncomfortable, but it is necessary. Long-term success depends on your willingness to evolve alongside the business. The founder’s vision may start the company, but the CEO’s discipline helps it scale.

The strongest leaders do not abandon their founder instincts. They refine them. They keep the vision and purpose that built the company while developing the systems, team and strategic focus required to sustain it. That is the transition no one fully prepares you for. It may also be the one that determines whether your company can truly grow beyond you.

Founders are often celebrated for their ability to do everything. In the early stages of a company, that closeness can feel necessary. You are close to the product, the brand, the customers, the operations and the decisions that keep the business moving.

That involvement can be powerful. It helps you understand the details, respond quickly and protect the vision while the company is still taking shape. But there is a point in every growing business when the same instincts that helped you build the company begin to limit it.

If every decision still depends on you, the company cannot move faster than your personal capacity. If every department relies on your direct involvement, growth becomes exhausting instead of expansive. The business may be getting bigger, but your leadership model is still built for the earliest stage.

On January 27, 2026, the visibility of thousands of businesses changed overnight — and almost nobody noticed why. That day, Google quietly swapped a new model, Gemini 3, into AI Overviews and AI Mode. There was no “core update” announcement and no warning to site owners.

Yet according to an analysis of the aftermath, the number of cited sources per AI answer jumped by roughly a third, freshness suddenly carried more weight and entity-rich websites gained share at the expense of thinner ones. ChatGPT, running on an entirely separate pipeline, was completely unaffected.

I have come to think of this event as the template for the second half of 2026. The first half made AI search official. Google published its first optimization documentation. Marketers began allocating more budget to AI search than to traditional SEO. The discipline of generative engine optimization moved from experiment to expectation.

The second half will be defined by something less visible but more consequential: the engines themselves are changing underneath us.

Model upgrades are the new algorithm updates

For two decades, marketers learned to brace for Google’s algorithm updates. The AI-era equivalent is the model swap — and unlike Google’s updates, these arrive unannounced, undocumented and on multiple platforms at once.

The mechanics explain why each one matters so much. Modern AI search systems do not process your question as a single query. They fan it out into many parallel sub-queries — often eight to twelve, and in ChatGPT’s case up to twenty — retrieve sources for each, verify claims and synthesize an answer.

As models become more capable, this process grows more thorough and, crucially, less gameable. Research already shows that only a quarter to a third of AI citations come from pages ranking in the traditional top ten. The newest models reason more, check more and trust selectively.

In our own client work, we observed this firsthand around the release of GPT-5.4: noticeably increased volatility in AI recommendations across accounts. Not necessarily steep drops, but a constant reshuffling that would have been unthinkable in the comparatively stable world of classic search rankings.

With Gemini 3.5 Pro arriving and further flagship releases expected from every major lab before year’s end, businesses should plan for several more of these invisible resets in the second half. The only durable hedge is content that survives machine scrutiny: verifiable claims, named expertise and consistent factual signals about who you are and what you do.

Three platforms, three different games

The second thing to understand about the coming months is that “AI search” is no longer one thing. The three dominant assistants are diverging into fundamentally different strategies.

ChatGPT is doubling down on personalization and monetization: its memory features are maturing rapidly, and its advertising pilot is expanding internationally to the UK, Mexico, Brazil, Japan and South Korea. Gemini is fusing Google’s retrieval and trust infrastructure with in-chat commerce, letting users complete purchases without ever leaving the conversation. Claude, by contrast, has positioned itself as the ad-free option focused on professional and agent-driven work.

The consequence is measurable: one large-scale citation study found that only 11% of domains are cited by both ChatGPT and Perplexity, and brand recommendations can differ by 40 to 60% across platforms for identical queries. Each engine is its own ecosystem, with its own biases and blind spots.

What makes this genuinely workable, however, is that the models will often tell you about those blind spots — if you ask. When we run AI visibility audits, we routinely ask the models directly why a client was not included in a recommendation.

These explanations should be taken with a grain of salt, since we cannot rule out that they are post-hoc rationalizations. But they frequently surface actionable insights.

One example: a dropshipping platform we work with was being recommended heavily by Gemini as a top option, yet had vanished entirely from certain ChatGPT recommendations — despite having been ChatGPT’s number-one pick for the same prompts just two months earlier. When we asked why, ChatGPT explained that the platform was not known for working well with Shopify, even though our prompt had never mentioned Shopify at all.

The model had silently made ecosystem compatibility part of its decision. After the client published substantial content addressing Shopify integration specifically, they reappeared in those recommendations.

That is the texture of GEO in late 2026: less about rankings, more about understanding — and correcting — what each model believes about you.

The personalization endgame

There is a deeper shift hiding inside the memory race. As ChatGPT, Gemini and Claude all build systems that remember individual users — their preferences, their history, their context — two people asking the identical question will increasingly receive different recommendations.

I argued recently that AI visibility is a winner-takes-all game, because most users simply accept an assistant’s initial recommendation rather than browsing alternatives. Personalization extends that logic to its conclusion: the contest becomes winner-takes-all per user.

A brand that wins the early interactions with a customer’s assistant gets reinforced within that relationship, query after query, while competitors become progressively harder to surface. It also means third-party visibility tools, which track generic prompts from anonymous accounts, will capture an ever-smaller slice of reality.

Expect measurement to get harder in the second half, not easier — and expect the premium on being a customer’s first AI-recommended choice to keep rising.

The web starts charging admission

The final trend on the horizon concerns the infrastructure beneath all of this. Publishers and infrastructure providers are erecting toll booths. Cloudflare now blocks declared AI crawlers by default and offers a pay-per-crawl model, millions of sites have opted out of AI training, and licensing intermediaries are signing up mid-sized publishers.

Every business now faces a strategic question that did not exist two years ago: open your content to AI systems and compete for citations, or block them and protect your work at the cost of invisibility.

My view — informed by having sat on the publisher side of the table as well as the marketer’s — is that history overwhelmingly favors staying open.

When Spotify effectively killed CD revenues, the music industry did not die. It restructured. Artists today earn far more from live events than their predecessors did, and smaller acts can build an audience and income through self-publishing at a speed that was impossible in the label-gatekeeper era.

AI will impose a similar restructuring on many industries, and not all of it will be comfortable — but businesses that withdraw from the new distribution layer to protect old revenue lines have rarely ended up on the winning side of such transitions. Adaptation, not retreat, is the historical pattern.

One practical aside: despite the hype, the llms.txt file — often sold as a quick AI visibility fix — is still used by no major AI provider in production, and Google has said on record it does not support it. For now at least, you can spend your energy elsewhere.

On January 27, 2026, the visibility of thousands of businesses changed overnight — and almost nobody noticed why. That day, Google quietly swapped a new model, Gemini 3, into AI Overviews and AI Mode. There was no “core update” announcement and no warning to site owners.

Yet according to an analysis of the aftermath, the number of cited sources per AI answer jumped by roughly a third, freshness suddenly carried more weight and entity-rich websites gained share at the expense of thinner ones. ChatGPT, running on an entirely separate pipeline, was completely unaffected.

I have come to think of this event as the template for the second half of 2026. The first half made AI search official. Google published its first optimization documentation. Marketers began allocating more budget to AI search than to traditional SEO. The discipline of generative engine optimization moved from experiment to expectation.

Flo Jacques bought her first home at 22 on a $35,000 salary as a college admissions counselor, simply because she’d saved $15,000 and wondered if buying made more sense than renting. It took her three more years of getting licensed, networking, and learning before she felt ready to buy an investment property. 

When she finally moved, she moved fast: a roach-infested single-family flood-zone rehab, followed a month later by a six-figure duplex renovation, followed by an off-market flip with a ceiling that didn’t meet code. Two years in, she’s built a four-property portfolio using 100% financing and has her sights set on real estate development. 

Here’s how she built it.

You went three years between buying your primary home and your first investment property. What finally pushed you to act?

I got my real estate license first to learn the business while I built up funds, since college admissions doesn’t pay much. I joined professional organizations and started attending investor-focused sessions, and by 2024, I knew I wanted to build a portfolio instead of working until I died. 

I found my first deal almost by accident: I was helping an investor client evaluate a 19-property portfolio a retiring investor was selling near Rocky Mount, North Carolina. While sending her the list, I decided to make offers on one or two properties myself. 

I went under contract for $90,000 but closed at $70,000 after discovering the property was in an undisclosed flood zone. I moved forward anyway, since the price was still right.

That first deal turned into a full gut renovation. How did the financing and the actual rehab go?

I found a hard money lender with no experience requirement, which is rare. They financed 100% of both the purchase and the rehab, as long as the total stayed under 70% to 75% of the after-repair value. All I had to cover were origination fees and closing costs. 

The renovation itself was brutal: We had to rebuild the entire foundation, and I went through three different contractors. The first didn’t have the crew for the scope, the second got greedy with pricing, and the third finished the job. 

The rehab budget started at $75,000 and ran over. When I went to refinance, the appraisal actually came in $26,000 lower than expected because the underwriter questioned my comps in a market with limited recent sales. That property is currently rented to a group home tenant for $1,595 a month.

A month after that first deal, you bought a $287,000 duplex in downtown Durham. How did that one perform?

Same hard money lender, same 100% financing structure. That renovation was supposed to be $65,000 but came in closer to $130,000, since I also furnished it to run as a midterm and short-term rental. I wasn’t checking in on the property regularly during construction, which I now consider a mistake; I was mostly just wiring money based on photos contractors sent me. 

Once finished, it appraised at $462,500, and I pulled cash out of the refinance to help recover from going over budget on both projects. It now cash flows between $800 and $1,000 a month on Airbnb and VRBO.

Your most recent deal was your first off-market find, and it had a defect most investors were avoiding. Walk us through it.

I found it on an off-market wholesaler platform after attending a private money lending conference that got me back in the game. The property had ceilings under seven feet, which doesn’t meet Raleigh’s code minimum, so a lot of investors were passing on it. 

I saw that as an opportunity to negotiate. I bought it for $120,000, and the ARV is a conservative $337,000. This time, since I’m now a full-time investor with more time for due diligence, I structured it more conservatively at 65% of ARV, built in a real contingency budget, and even started paying myself for my own time managing the project. We’re currently raising the roofline to get the ceilings to code.

What’s the biggest lesson you’d pass on to someone considering this same sub-$100K, heavy-rehab strategy?

Structure your deals more conservatively than you think you need to, especially in cheaper, high-renter markets where there aren’t many comparable sales to support a high post-renovation appraisal. 

On my first deal, I underwrote at 75% ARV and got burned when the underwriter pushed back on my comps. I also learned to budget in contingencies and to pay myself for the time I put into managing a renovation, not just materials and labor. 

Beyond that, don’t be afraid to move on properties other people are passing on, whether that’s a flood zone or a code issue, as long as you can put a real dollar amount on what it costs to fix.

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