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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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When entrepreneurs talk about expansion, most conversations focus on revenue, opportunity and growth. Very few people talk about the operational pressure that comes with opening a second location. That pressure is where many businesses start to break down.

I have seen this happen in healthcare and in other industries. A founder builds a successful first location through hard work, close oversight and personal involvement. Then they assume the same formula will automatically work somewhere else. What they discover very quickly is that success tied to one person rarely transfers cleanly to another location.

When my brother Stephen and I started expanding our healthcare businesses, we realized something important. If the business only worked because we were physically present every day, then we did not actually have a scalable company. We had a demanding job with a good revenue stream.

That realization forced us to approach expansion differently. Before opening another location, we began asking ourselves a set of questions designed to test whether the business could truly operate at scale. Over time, those questions became our version of a franchise test. Here are the seven questions I believe every founder should answer before expanding.

1. Can someone else run your operation successfully?

This is the first and most important question. If the business depends heavily on your personal oversight, your second location will struggle from the beginning.

In our early years, I stayed involved in nearly every decision. I reviewed operations constantly, solved issues personally and approved far more than I should have. At the time, I thought that level of involvement protected quality. In reality, it created dependency.

Expansion requires the opposite. Your systems must allow competent people to operate successfully without constant intervention from the founder. A simple way to test this is to step away temporarily from day-to-day operations. If progress slows dramatically during your absence, your business still depends too heavily on you.

2. Have you documented your core processes?

Undocumented success does not scale. Many founders carry operational knowledge in their heads. They know how to onboard customers, resolve issues, manage scheduling or maintain quality because they have repeated those actions hundreds of times. The problem appears when another team tries to replicate the process without direct access to the founder.

When we started growing our healthcare businesses, documenting processes became one of the most valuable things we did. We created standard operating procedures for onboarding, scheduling, communication, staffing and patient workflows. That documentation created consistency across locations.

One exercise I recommend is identifying the five most critical systems in your company and documenting them step by step. Keep the instructions simple, practical and repeatable. A scalable SOP should allow another capable person to produce the same result consistently.

3. Does your culture exist beyond you?

A strong first location often reflects the founder’s personality and energy. Employees respond directly to your leadership style, standards and communication. The challenge comes when you attempt to recreate that environment somewhere else. Culture must become operational, not personal.

In our companies, we learned that culture requires reinforcement through hiring, training and leadership development. You cannot assume people automatically understand your standards because they spent time around you.

Before expanding, ask yourself whether your values are clearly communicated throughout the organization. Your team should understand how decisions are made, how customers are treated and what behaviors define success inside the company. When culture only exists through the founder’s personality, expansion creates inconsistency very quickly.

4. Do you have leaders ready to grow with the company?

A second location creates leadership pressure immediately. Someone has to oversee operations, manage people, solve problems and maintain standards while you divide your attention across multiple sites. One of the biggest mistakes founders make is expanding before building leadership depth.

I learned this personally as our businesses grew. Early on, too many decisions still came back to me because leaders had not fully developed ownership within their areas. That slowed growth and limited scalability.

Before expanding, identify whether you already have strong leaders capable of running operations independently. If you cannot clearly name those individuals today, leadership development needs attention before expansion. One practical step is assigning increasing responsibility to existing team members before opening another site — give them ownership over projects, operations or departments now so you can evaluate how they lead under pressure.

5. Can your systems handle more complexity?

Growth always increases complexity. Communication expands. Scheduling becomes harder. Staffing pressure increases. Financial oversight becomes more demanding. Without strong systems, complexity turns into chaos very quickly.

One of the best decisions we made during expansion was investing in automation and operational systems early. We evaluated repetitive tasks and asked whether technology could improve efficiency and consistency. Scheduling, communication, billing and documentation all became areas where systems reduced operational strain. This is not about replacing people — it is about creating structure that allows people to perform at a higher level.

Before opening another location, evaluate where your current systems already feel strained. Expansion magnifies weaknesses that already exist.

6. Is your first location consistently profitable?

Some founders pursue expansion too early because growth feels exciting. The danger is that a weak first location creates two weak locations instead of one strong company.

Your original operation should demonstrate stability before expansion begins. Revenue should be predictable. Margins should support growth. Operational issues should feel manageable rather than constant.

When we expanded into additional healthcare businesses, we focused heavily on operational consistency before adding complexity. That discipline created a stronger foundation for future growth. A useful exercise is reviewing the last 12 months of performance — look for operational stability, team consistency, customer retention and financial predictability. Expansion works best when the original location operates from strength rather than momentum alone.

7. Are you expanding strategically or emotionally?

This may be the hardest question of all. Opening another location can absolutely transform a business — it can create leverage, expand impact and position the company for long-term growth. But expansion amplifies everything inside the organization, including weaknesses.

That is why I believe the franchise mindset matters so much. Franchises succeed because they create repeatable systems, documented standards, leadership consistency and operational discipline. Founders who approach expansion with that same mindset dramatically improve their chances of sustainable growth.

The goal is never just opening another location. The goal is building a business that operates successfully beyond the constant presence of the founder.

If you tell someone you’re an entrepreneur, they’ll assume you’re from one of the anointed cities: New York, Silicon Valley, maybe Austin or Miami. Start a company outside of these major metros, and the general read is that you’re a farm league founder.

I know otherwise. I’ve built seven companies, all in my hometown of Lexington, Kentucky. I travel regularly, and when I tell people I’m from Kentucky, they often look surprised and say, “What’s going on in Kentucky?” Those who live here know there’s a lot going on. Lexington may be a mid-sized market, but it’s one that has a flourishing entrepreneurial community.

My friend Scott Shapiro, Lexington’s former Chief Innovation Officer, has done research on what he calls “University Cities” — mid-sized markets like Lexington, Madison and Ann Arbor, which are built around major research universities.

His data shows that these cities match the largest metros in talent, entrepreneurship and economic resilience at a fraction of the cost. The bottom line is this: Markets like Lexington give founders advantages that simply don’t exist in big cities.

Failure is survivable

Everyone loves a good entrepreneurial success story. The same can’t be said about the stories of failure. But even the most successful founders leave a trail of failures behind them. It’s inevitable.

I’m no stranger to failure. In 2017, I was running a clothing brand called Provisions, a Kentucky apparel brand built around giving back. We had a great product, customers and momentum. Then there was a market shift that impacted our licensing, and the ground disappeared out from under us. There was no pivot to make. The business was done.

In the end, that failure cost me a few hard months and a bruised ego. A year and a half later, I started Bolt Marketing, the agency I run today. If I’d been carrying San Francisco rent and payroll when Provisions went down, that story would have ended differently. In Lexington, the failure was tuition.

This is where the math comes into play. Housing, salaries, office buildouts and daily living expenses in mid-sized markets are a fraction of what they are in major metros, and all of it rolls up into one critical number: how long you can keep going before the money runs out. Lower costs mean more runway on less capital. When a failed idea costs you a few months instead of everything, you can afford to try, miss and try again.

You can make a name for yourself

In Silicon Valley, there might be thousands of businesses doing exactly what you do. You can produce excellent work for years and never make real headway. But in a mid-sized market, you can become the big fish, and if you do it right, you can get there fast.

Produce great work, make it visible, and the word gets around. Less competition and a tighter community mean a reputation actually builds, and a strong local reputation is something that will convert directly into revenue.

Networking in big cities is transactional. Everyone is hunting for their next opportunity, and genuine business relationships are hard to come by. I’ve seen this first-hand in bigger markets and have come to understand that mid-sized ones run on a completely different operating system. The business community is tight enough that real, collaborative relationships form on their own. Founders here look for ways to help each other. Those relationships become the most dependable source of referrals and new business you’ll ever have.

At Bolt, we regularly host happy hours, panels and events to bring the Lexington business community together. Nobody’s pitching anybody. People show up to learn from each other and enjoy the company, and lasting relationships come out of that. It can be harder to replicate that in a transient city of 8 million.

It’s easier to hold onto top talent

In hyper-competitive markets, your best people are always one recruiter call away from leaving. There’s always going to be a better offer somewhere. This means frequent turnover and constant pressure to keep your team intact.

In markets like Lexington, fewer businesses are competing for the same employees, and people live here on purpose. Family, affordability, lifestyle. When someone can buy a house, raise kids and still do work that interests them, they have far less reason to shop around.

This stability compounds. Institutional knowledge stops walking out the door every 12 months. Culture has time to form. People grow within your company, rather than treating it as a layover.

It’s not all easy

The advantages of mid-sized markets are very real — but there are downsides to any geography. You can’t have a surfing company in Omaha. But even beyond the obvious mismatches, if your business depends on large outside investment, the coastal metros give you more shots at that funding. And your local market in a smaller city is automatically smaller, which means some businesses have to think beyond their home geography from day one.

But these constraints push you toward building a stronger, more financially sound company from the beginning. The limits of a mid-sized market sharpen you as an operator.

Choose the unexpected location

I love big cities. There’s an energy about them that is infectious, and you can’t help but want to create. But energy doesn’t pay the bills; opportunity does, and it lives in more places than people think. The most interesting thing you can do as a founder is the thing people don’t expect, and building a thriving company in an “unexpected” place is exactly that. It makes you distinctive. It lets you build a team with hometown pride. It connects your journey to a community that will show up for you in ways a major city never will.

And the case for building business in unexpected geographies keeps getting stronger. In a post-Covid world, remote work erased the last real argument for coastal geography. Your clients, your talent and your capital no longer require a specific zip code. You don’t have to move to where people think founders should go. You can build a successful business right where you are. Pick a mid-sized market, plant your flag, and get to work. To some, you may look like a farm league founder — but the farm league is where the big leaguers come from anyway.

If you tell someone you’re an entrepreneur, they’ll assume you’re from one of the anointed cities: New York, Silicon Valley, maybe Austin or Miami. Start a company outside of these major metros, and the general read is that you’re a farm league founder.

I know otherwise. I’ve built seven companies, all in my hometown of Lexington, Kentucky. I travel regularly, and when I tell people I’m from Kentucky, they often look surprised and say, “What’s going on in Kentucky?” Those who live here know there’s a lot going on. Lexington may be a mid-sized market, but it’s one that has a flourishing entrepreneurial community.

My friend Scott Shapiro, Lexington’s former Chief Innovation Officer, has done research on what he calls “University Cities” — mid-sized markets like Lexington, Madison and Ann Arbor, which are built around major research universities.

Y Combinator (YC), a well-known startup accelerator that helped launch companies like Reddit, DoorDash and Airbnb, has invested in more than 5,000 startups since 2005. Now YC leaders note that founders seem to be outsourcing writing their applications to AI. 

The YC application requires founders to explain how they selected their idea, identify competitors in the space and outline their plans to generate revenue. Some tell-tale signs reveal that many tech-focused founders have recently decided to use AI to write answers to these questions.

One giveaway is the longer responses that AI produces. According to YC partner Tyler Bosmeny, YC applications have increased in length by 60% over the past three years. “I wonder what could explain that…” he wrote on X earlier this week.

Another YC partner, Pete Koomen, spent a week reading applications. He wrote in an X post this week that “back in my day (one year ago) founders didn’t talk like this.” He shared a chart showing that the percentage of applications containing the word “wedge” went from less than 1% in spring 2025 to greater than 20% in summer 2026. 

Meanwhile, em dashes, another AI giveaway, started growing in use in 2023 and “really hit their stride in 24,” Koomen said. According to the data he shared, by summer 2025, more than 50% of YC applications used em dashes. 

Koomen emphasized that the spacing of those em dashes was important. Em dashes with spaces around them spiked in use in summer 2025, around the same time that the word “wedge” became more popular. These signs of AI use coincided with the launch of Anthropic’s Opus 4 AI model, he said. 

One word decreased in popularity

YC co-founder Paul Graham wrote in an X post in April 2024 that someone sent him a cold email suggesting “a novel project.” Then he noticed that the email used the word “delve.”

“My point here is not that I dislike ‘delve,’ though I do, but that it’s a sign that text was written by ChatGPT,” Graham wrote in the post, which has been viewed 2.6 million times. 

He added a chart created by researcher Philip Shapira, which illustrated that the word “delve” has jumped from nearly zero to nearly 18,000 instances in published papers and articles from 1990 to 2024. 

“No one uses it [delve] in spoken English,” Graham wrote. “It’s one of those words like ‘burgeoning’ that people only use when they’re writing and want to sound clever.”

Founders using AI to write applications have recently stayed away from “delve.” Koomen found that the word only spiked in 1.25% of applications in the winter of 2024, before Graham’s post. 

Graham said more recently, in an X post in May, that “a lot” of emails from founders now adopt “a hard-hitting journalistic style.”

“I know they’re written by AI, because no founder ever wrote this way before,” he wrote, adding, “It feels like being lied to.”

Y Combinator (YC), a well-known startup accelerator that helped launch companies like Reddit, DoorDash and Airbnb, has invested in more than 5,000 startups since 2005. Now YC leaders note that founders seem to be outsourcing writing their applications to AI. 

The YC application requires founders to explain how they selected their idea, identify competitors in the space and outline their plans to generate revenue. Some tell-tale signs reveal that many tech-focused founders have recently decided to use AI to write answers to these questions.

One giveaway is the longer responses that AI produces. According to YC partner Tyler Bosmeny, YC applications have increased in length by 60% over the past three years. “I wonder what could explain that…” he wrote on X earlier this week.

A few years ago, I helped start a company called Kitchen Data Systems. At the time, ghost kitchens were exploding. Delivery was booming, and it felt like the kind of opportunity you move on quickly. We had some traction and real revenue early, but the business never scaled the way we expected. So we pivoted.

Instead of building delivery-only food brands, we explored a buyers’ club model for independent restaurants. Large chains like Domino’s can negotiate far better ingredient pricing because they buy on a massive scale. Smaller restaurants often serve great food but pay more because they lack that purchasing power. Our idea was to aggregate demand so independent operators could access similar pricing advantages.

It was a smart pivot, but we couldn’t execute the model well enough, and eventually we ran out of time and money. From the outside, that might look like failure. From the inside, it was a lesson in how businesses actually evolve. Almost every founder will face a moment where an idea doesn’t work the way they expected — you can’t avoid those moments. The real test is how you recover when they happen.

Conduct an honest post-mortem

The first step after a setback is analyzing what actually happened. Many founders either skip this step or let emotion dominate the process. A proper post-mortem is about identifying which assumptions were wrong and where execution fell short. Sometimes the market is not ready. Sometimes the product fails to meet the customer’s needs. Other times, the strategy is solid, but the team cannot execute it quickly enough.

In our case, the concept of helping independent restaurants with purchasing power had merit. The problem was execution — we were not able to build the system quickly enough for the model to work at scale. If founders misdiagnose failure, they often carry the wrong lesson into the next venture. The goal of a post-mortem is to understand the real cause so that the next decision improves.

Separate emotion from evidence

Building a company is deeply personal. Founders invest years of effort, reputation and energy into something that may or may not succeed. When the outcome falls short, the emotional response can be strong. That reaction is natural, but it also clouds judgment.

A common mistake founders make is convincing themselves they just need more time. Others double down on a strategy that clearly is not working because walking away feels like admitting defeat. A better approach is to step back and evaluate the situation objectively. Look at the numbers. Look at customer behavior. Look at the growth trajectory. If you were evaluating the opportunity fresh today with the information you now have, would you still pursue it?

If the honest answer is no, continuing to pour resources into the same strategy won’t improve outcomes. Discipline in entrepreneurship often means recognizing the difference between persistence and stubbornness.

Protect the relationships built along the way

When companies struggle or shut down, it can feel safe to retreat. Founders stop returning calls, investors move on and teams scatter. That instinct is shortsighted. One of the most valuable assets in business is your reputation during difficult moments.

Entrepreneurship is a long journey. The people you work with during one venture often appear again later in your career. A former employee may become a founder you invest in. An early investor may support your next idea. A partner from a failed project may introduce you to a future opportunity.

Because of that, how you handle difficult moments matters. Communicating honestly, acknowledging mistakes and treating partners fairly during setbacks builds long-term trust. People understand startups fail — what they remember is how you behaved when things became difficult. Maintaining those relationships ensures that one failed venture does not close the door on future opportunities.

Extract one strategic lesson

Rather than generating a long list of abstract lessons, a more useful approach is to identify one lesson that genuinely changes how you operate moving forward. Maybe it is about testing demand earlier, before building infrastructure. Maybe it is hiring differently or focusing on a different customer segment. Sometimes the lesson is simply about speed — early-stage companies cannot afford to wait long for proof. If the data is not moving in the right direction, adjustments must happen quickly.

Entrepreneurship rarely follows a straight path. Many successful founders tested several ideas before discovering the one that gained traction. Each attempt produces information that helps refine the next decision. If you walk away with one clear adjustment in how you evaluate opportunities, the setback has already paid for itself.

Re-enter the arena with calibrated conviction

The final step after a setback is returning to the arena. After experiencing failure, a drop in confidence is common. Doubt creeps in. Survival urges us to avoid risk or wait for certainty before trying again. But entrepreneurship and certainty are seldom bedfellows. Sales conversations begin with rejection. Investors decline pitches. Customers say no. Progress comes from continuing to ask, test and move forward. You may even have to face failure again before you finally find a company that takes off.

I was reminded of this recently by a story from one of my interns. He was standing in line at a Wetzel’s Pretzels and noticed the person ahead of him was Anthony Kiedis from the Red Hot Chili Peppers. He debated whether to ask for a photo, then decided to go for it. The worst outcome would have been a polite no. Instead, he walked away with a photo and a story he will remember for years.

Entrepreneurship works the same way. Most opportunities start with a message, a meeting request or a simple question that could easily be ignored. Occasionally, that attempt opens the door to something much bigger. After a setback, don’t forget what happened — apply the lessons while maintaining the courage to try again.

The end is up to you

Setbacks are an unavoidable part of building companies. Ideas fail, strategies miss the mark and sometimes the timing simply does not work. Those moments are sometimes brutal. They’re discouraging. It can feel like the end. But failure in entrepreneurship is only final if you stop learning from it.

Founders who recover well approach setbacks with discipline. They analyze what happened honestly, separate emotion from evidence and protect the relationships built along the way. They extract one lesson to inform the next decision, then return to the market with renewed focus.

A few years ago, I helped start a company called Kitchen Data Systems. At the time, ghost kitchens were exploding. Delivery was booming, and it felt like the kind of opportunity you move on quickly. We had some traction and real revenue early, but the business never scaled the way we expected. So we pivoted.

Instead of building delivery-only food brands, we explored a buyers’ club model for independent restaurants. Large chains like Domino’s can negotiate far better ingredient pricing because they buy on a massive scale. Smaller restaurants often serve great food but pay more because they lack that purchasing power. Our idea was to aggregate demand so independent operators could access similar pricing advantages.

It was a smart pivot, but we couldn’t execute the model well enough, and eventually we ran out of time and money. From the outside, that might look like failure. From the inside, it was a lesson in how businesses actually evolve. Almost every founder will face a moment where an idea doesn’t work the way they expected — you can’t avoid those moments. The real test is how you recover when they happen.