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The more businesses I built, the more I realized that industries change, but the problems that determine success often repeat. Here are five patterns every entrepreneur should learn to recognize.

From the outside, my career may look like I kept changing lanes. I have built and operated businesses in hospitality, real estate, construction, home inspections, healthcare and digital marketing. People sometimes ask how I move between industries that seem so different. The truth is, I don’t begin with the industry. I begin with the problem.

A hotel guest, a homebuyer, an urgent care patient and a small-business owner are not the same customer. But each wants clarity, consistency and confidence. Each wants to know what happens next, whether the company can be trusted and whether the experience will be worth the money.
The greatest advantage of working across industries has not been diversification alone. It has been pattern recognition.

One NBER study of Danish firms found serial entrepreneurs were 39% more productive than novice entrepreneurs. But experience only becomes an advantage when you understand which lessons transfer and which do not.

Look for the emotion beneath the transaction

Customers rarely buy only the product or service listed on the invoice. A hotel guest is not just paying for a room. After a long day of traveling, that guest may be buying rest and reassurance. A patient visiting urgent care wants answers, relief and confidence that someone is paying attention. A homebuyer ordering an inspection wants more than a report. The buyer wants to feel informed before making one of the largest financial decisions of their life.

This is similar to the jobs-to-be-done approach developed by the late Harvard Business School professor Clayton Christensen: Focus on what the customer is really trying to accomplish. In every business, I ask three questions: What is the customer worried about? What would make the experience easier? What must happen for the customer to trust us?

Those questions often teach me more than a traditional competitor analysis.

Transfer principles, not procedures

Hospitality taught me that people remember how a business makes them feel. I carried that lesson into healthcare, but that did not mean turning an urgent care center into a hotel. It meant translating the principle.

In a hotel, a warm welcome, clear directions and quick resolution can reduce stress. In urgent care, those same principles may become a respectful check-in, accurate expectations about wait times and clear communication about the next step.

Franchising taught me another transferable lesson: Systems create consistency, but only when people understand and use them. That principle has helped us grow inspection operations across multiple markets. The procedures are different, but the need for training, accountability and consistent execution is the same.

When you see a successful practice in another industry, don’t copy it word for word. Identify the principle underneath it, then adapt it to your customer, team and operating environment.

Treat repeated friction as market research

Some of my best business opportunities didn’t begin in a brainstorming session. They began with a problem I kept seeing.

While operating local businesses, I watched strong companies lose attention to competitors that were easier to find and better at explaining their value online. That repeated problem eventually helped lead us into digital marketing. A service you struggle to source, a question customers ask every week or a workaround your team has quietly accepted may point to a larger opportunity.

The U.S. Small Business Administration recommends combining market research with competitive analysis to understand demand and identify an advantage. You can start closer to home.

For 30 days, keep a friction log. Record recurring complaints, delays, outside services you repeatedly purchase and manual workarounds. Then ask who else has the same problem, what it costs them and whether they would pay for a better solution.

Validate the pattern before building around it

Seeing a recurring problem doesn’t automatically mean you’ve found a viable business. Because you understand the problem, you may assume others value the solution as much as you do. Before committing significant time or money, talk with potential customers. Test a limited version. Ask customers to pay rather than simply asking whether they like the idea. Set a budget, a deadline and a clear result the test must produce.

Not every frustration deserves a new company. Some are operational problems that should be fixed inside the existing business. The goal is to distinguish between an inconvenience and a market.

Build a leader, not another job

A new opportunity becomes dangerous when it depends on the founder for every decision. Before entering another business or market, I consider who will lead it, what authority that person will have and which measurements will show whether the operation is healthy.

If every customer issue, employee question and financial decision comes back to you, you have not built another business. You have created another job. The common thread across my businesses is not a particular industry. It is solving real problems through service, systems and trust.

Entrepreneurs don’t have to chase every trend. They need to notice recurring patterns, translate lessons carefully, validate demand and develop people who can lead. Once you recognize patterns, new industries become less intimidating. More importantly, you become better at knowing which opportunities deserve a yes — and which require a disciplined no.

The more businesses I built, the more I realized that industries change, but the problems that determine success often repeat. Here are five patterns every entrepreneur should learn to recognize.

From the outside, my career may look like I kept changing lanes. I have built and operated businesses in hospitality, real estate, construction, home inspections, healthcare and digital marketing. People sometimes ask how I move between industries that seem so different. The truth is, I don’t begin with the industry. I begin with the problem.

A hotel guest, a homebuyer, an urgent care patient and a small-business owner are not the same customer. But each wants clarity, consistency and confidence. Each wants to know what happens next, whether the company can be trusted and whether the experience will be worth the money.
The greatest advantage of working across industries has not been diversification alone. It has been pattern recognition.

One NBER study of Danish firms found serial entrepreneurs were 39% more productive than novice entrepreneurs. But experience only becomes an advantage when you understand which lessons transfer and which do not.

Look for the emotion beneath the transaction

Customers rarely buy only the product or service listed on the invoice. A hotel guest is not just paying for a room. After a long day of traveling, that guest may be buying rest and reassurance. A patient visiting urgent care wants answers, relief and confidence that someone is paying attention. A homebuyer ordering an inspection wants more than a report. The buyer wants to feel informed before making one of the largest financial decisions of their life.

This is similar to the jobs-to-be-done approach developed by the late Harvard Business School professor Clayton Christensen: Focus on what the customer is really trying to accomplish. In every business, I ask three questions: What is the customer worried about? What would make the experience easier? What must happen for the customer to trust us?

Those questions often teach me more than a traditional competitor analysis.

Transfer principles, not procedures

Hospitality taught me that people remember how a business makes them feel. I carried that lesson into healthcare, but that did not mean turning an urgent care center into a hotel. It meant translating the principle.

In a hotel, a warm welcome, clear directions and quick resolution can reduce stress. In urgent care, those same principles may become a respectful check-in, accurate expectations about wait times and clear communication about the next step.

Franchising taught me another transferable lesson: Systems create consistency, but only when people understand and use them. That principle has helped us grow inspection operations across multiple markets. The procedures are different, but the need for training, accountability and consistent execution is the same.

When you see a successful practice in another industry, don’t copy it word for word. Identify the principle underneath it, then adapt it to your customer, team and operating environment.

LinkedIn doesn’t want to lose users to a flood of AI content. 

In an effort to create a better user experience, LinkedIn chief product officer Hari Srinivasan announced in a post on the platform last month that the company would include a new feature: a “seems like AI slop” button. 

AI slop refers to poorly generated AI content. LinkedIn is allowing users to flag posts that appear to be AI-generated.

The button immediately proved popular. Srinivasan wrote on LinkedIn last week that within the first two weeks of the button’s launch, more than a million people have used it. 

“Overall members are now experiencing 40% less views on what we classify as AI slop from just a few weeks ago,” he wrote in the post. “Despite the progress, we know we have more to do to ensure LinkedIn remains a place where you can find real people & real perspectives.”

Avoiding activity from AI bots

LinkedIn is trying to avoid the “dead Internet theory,” or the idea that much of what users see online is no longer made by real people for real people. The theory imagines an Internet increasingly filled with bots, AI-generated posts, fake accounts and automated engagement. 

In other words, machines effectively post, like, comment and boost each other, making most of the content on the Internet AI-generated.

As AI agents and bots flood online spaces, the theory has gained traction. 

“There’s a lot of missing pieces of information, but a lot of the observed data suggests the same thing, which is there is more bot activity,” Rudy Yang, PitchBook’s enterprise and retail fintech analyst, recently told Fortune. “Agentic AI activity is driving a lot of the browser activity you’re seeing.”

AI content is gaining ground

Data supports the idea that the web is increasingly dominated by AI. Cloud platform Cloudflare said in April that for the first time, automated traffic had overtaken human traffic on the Internet. As of Wednesday, bots generated 58% of search requests, compared to 42% from people, per Cloudflare.

AI-written material is also showing up more often across the web. In a Pew Research Center analysis released last week, researchers examined 10,000 webpages gathered in July and found that 10% contained strong indicators of AI authorship, up from roughly 2% five years earlier. 

More than one-third of webpages published since ChatGPT’s late-2022 debut showed at least some evidence of AI-generated writing, the analysis added.

LinkedIn appears especially exposed to the shift. The professional networking site, used by more than 1.3 billion registered members to follow companies, industries and workplace news, had a larger share of AI-generated long-form posts than Medium, X or Substack, according to a  July analysis by AI-detection startup Pangram. 

Pangram classified more than 40% of LinkedIn’s long-form posts as entirely AI-generated.

LinkedIn doesn’t want to lose users to a flood of AI content. 

In an effort to create a better user experience, LinkedIn chief product officer Hari Srinivasan announced in a post on the platform last month that the company would include a new feature: a “seems like AI slop” button. 

AI slop refers to poorly generated AI content. LinkedIn is allowing users to flag posts that appear to be AI-generated.

Between 2020 and 2025, U.S. electricity demand grew roughly 1.7% a year, more than ten times the annual pace utilities saw over the prior decade and a half, according to federal energy forecasts. Data centers, EV charging depots and reshored manufacturing plants are pulling more current through wires than the grid was ever designed to carry.

For founders building anything that touches physical infrastructure, real estate, logistics or manufacturing, this is not an abstract policy debate. It’s a supply chain risk. A transformer failure in the wrong substation can shut down a distribution center for days. Power reliability is quietly becoming a competitive advantage.

The challenge: Aging infrastructure meets rising demand

Much of the U.S. transmission network was built between the 1950s and 1980s, engineered for a slower-growing, less electrified economy. Layer today’s load onto yesterday’s steel and copper, and stress shows up fast: sagging conductors, overheated transformers, voltage drops during peak demand.

Add geography to the equation. Utility crews service lines strung across mountain passes, wetlands and dense urban cores, often well above 100 feet, exposed to wind, ice and heat that legacy equipment was never rated for. Every outage compounds: hospitals lose backup capacity, cold storage spoils inventory, data centers throttle compute as AI workloads push demand the grid was never designed to carry. The grid isn’t just old. It’s outmatched by the loads now riding on it.

Why maintenance is more critical than ever

Reactive maintenance, fixing equipment only after it fails, was tolerable when demand stayed flat. It isn’t anymore. A single unplanned outage can cost a mid-size manufacturer six figures in lost production, and repeated failures invite regulatory scrutiny utilities can’t afford.

Preventive maintenance flips the economics: Crews replace worn hardware on a schedule, before it strands a substation. It also protects people. Line workers hold some of the most physically demanding jobs in any industry, and a single fall or arc flash can end a career. Compliance bodies increasingly treat inspection cadence as a legal requirement, not a courtesy.

The role of advanced maintenance technologies

Utility maintenance has moved well past bucket trucks and paper inspection logs.

Insulated aerial platforms, drone inspections and modular repair rigs now let crews reach damaged conductors without de-energizing entire feeder lines. That single change cuts repair windows from days to hours.

To reduce downtime and protect crews working at extreme heights, utility providers increasingly rely on specialized electric line repair equipment built specifically for high-voltage transmission and distribution work. The same logic that keeps warehouse employees off ladders for hazardous tasks is pushing utilities toward remote, automated inspection wherever the terrain allows it.

Crews report real gains from this shift:

• Fewer full line shutdowns during routine repair work
• Lower injury rates for elevated tasks
• Faster mobilization to remote or storm-damaged sites
• Longer equipment lifespan through frequent, less invasive servicing

Scaling grid expansion with smarter solutions

Renewable generation adds complexity before it adds resilience. Solar farms and wind installations often sit far from existing substations, requiring new transmission runs into terrain utilities have rarely serviced. Data center power demand alone is projected to nearly triple by 2030, forcing utilities to expand capacity while keeping existing customers online.

Smarter deployment now centers on:

• Modular substations installed without months-long shutdowns
• Rural line extensions using rapid-deployment repair equipment instead of permanent crews
• Staged upgrades that isolate single circuits rather than whole grids

Business and economic implications

Reliable power underwrites everything from manufacturing schedules to server uptime. Every hour of outage ripples through payroll, spoiled inventory and missed shipping windows — the same triage businesses run through after any physical disruption.

Faster repair cycles also help utilities retain skilled linework crews. Turnover is expensive to replace and slow to train; equipment that reduces physical strain and risk keeps experienced workers on the job longer, itself a resilience asset during storm season or rapid buildout.

The future of grid maintenance

Predictive analytics are starting to flag failing transformers before they fail, using sensor data the same way manufacturers now forecast equipment breakdowns. Remote monitoring, satellite imagery and automated drone patrols are shrinking the gap between damage and dispatch.

Capital is following. Utilities and private investors are funding infrastructure at a pace not seen in decades, betting that reliability, not just capacity, will define which grids can support the next wave of electrified industry.

Reliability depends on innovation

Grid expansion without maintenance investment is a bet against physics. Every new data center, EV fleet and factory adds load to infrastructure that still ages on a fixed schedule.

Business leaders building near that grid should treat maintenance capacity, not just generation capacity, as a site-selection criterion. Ask utilities how fast they can restore power, not just how much they can supply. The company that plans around repair speed, not average uptime, will be the one still running when the next storm or surge hits.

Between 2020 and 2025, U.S. electricity demand grew roughly 1.7% a year, more than ten times the annual pace utilities saw over the prior decade and a half, according to federal energy forecasts. Data centers, EV charging depots and reshored manufacturing plants are pulling more current through wires than the grid was ever designed to carry.

For founders building anything that touches physical infrastructure, real estate, logistics or manufacturing, this is not an abstract policy debate. It’s a supply chain risk. A transformer failure in the wrong substation can shut down a distribution center for days. Power reliability is quietly becoming a competitive advantage.

The challenge: Aging infrastructure meets rising demand

Much of the U.S. transmission network was built between the 1950s and 1980s, engineered for a slower-growing, less electrified economy. Layer today’s load onto yesterday’s steel and copper, and stress shows up fast: sagging conductors, overheated transformers, voltage drops during peak demand.

On the evening of Friday, March 14, 2025, the White House issued an executive order that listed the Community Development Financial Institutions Fund (CDFI) among federal entities to be eliminated to the maximum extent allowed by law. My phone lit up, and my inbox was flooded within the hour. I have the privilege of serving as the CEO of B:Side Capital, a Small Business Administration (SBA) lender and certified community development financial institution, and the order had just put a large part of my organization directly in its crosshairs. I knew that come Monday morning, I would need to present a clear plan for my team and board members.

I knew that mission-based lenders wouldn’t escape the scrutiny of the newly-formed Department of Government Efficiency (DOGE), but I didn’t think that the CDFI fund would be targeted in such a dramatic manner. I didn’t have a plan in place for this move. Nobody did. What I had in its place was a code, and it turned a chaotic weekend into a sequence of decisions that had been explored long before the crisis hit.

I also teach leadership at Arizona State University, and from both the classroom and the boardroom, the same pattern is impossible to ignore: When real pressure arrives, the values we espouse are too vague to help. Concepts like “Integrity” or “People First” cannot tell you whether to cut staff, go public with your concerns or just quietly wait for the courts. Those words can sit alongside almost any decision without consequence, which is exactly why leaders who rely on them drift from their core beliefs.

What you need instead is a code: a short set of written commitments specific enough to be violated. I spent years studying leaders who navigated far worse than a bad news cycle, from the Roman Senate to the Depression-era Army, for my latest book on crisis-era leadership. The leaders who held in the face of crisis did not share a temperament or a strategy. They shared a moral architecture or code that held up under pressure. Their codes looked different, reflecting their unique backgrounds and perspectives, but they had one important thing in common: They were developed before the crisis hit. You can do the same by following these three simple steps.

Write a line specific enough to violate

State one thing you will not do regardless of what it costs you, and state it as a behavior, not a value. Platitudes like “I will not compromise my integrity” are useless; you can rationalize just about anything and convince yourself that your integrity remains unviolated. “I will not tell my team the business is fine when I know it is not” is different. It represents a real line in the sand. You either crossed it or you did not.

That weekend in March, my line was already written: I would not soften the truth with my team just to calm fears and placate them. Instead, I filmed a quick video telling the team, plainly, that we were facing an existential threat to part of our business, and that we would meet it methodically with our culture intact. It was uncomfortable, and part of me felt like I should have done more to soothe their nerves. However, I knew deep down that this approach represented the fastest path to finding an actual solution, and that is precisely what my team deserved.

Test your own line against the hardest situation you faced in the last two years. If it does not produce a clear answer, it is not specific enough yet.

Build the restraint before the offer arrives

Former President George Washington’s most consequential and lasting act was refusing power that no law required him to refuse. He could have been king, but he decided to take a different path years before the temptation showed up. That is the part that matters: The moment of maximum temptation is the worst possible time to be working out your principles for the first time. By then, the offer arrives dressed in arguments that almost always lead to justification.

Be wary of the temptation to do what feels good, for that instinct almost always betrays you. In the weeks after the order, there was a very real temptation to engage in public fight framing the battle as one of good against evil. This was nonsense, of course, but plenty of voices in our industry lashed out at the administration anyway. At times the pull to join them was real.

My team’s culture of restraint had been established and cultivated long before: We would not attack, and we would not let the response turn emotional. Instead, we worked our channels in Washington, engaging as constructively as we could to make the program’s value plain to the people who would decide its fate. You can do the same. Simply write down your non-negotiables before the pressure mounts, then tell it to someone who will hold you to it. A restraint kept private is only a preference.

Test your values every quarter

Leaders rarely fail in one dramatic moment. They fail one defensible decision at a time, each small compromise drawing them slightly further from the person they want to be. Seneca, the Stoic philosopher who ended up justifying the crimes of Nero’s court, is history’s sharpest warning that intelligence is no protection against drift.

The test that catches it is simple. Identify the person whose moral judgment you trust above your own, the one who would never let you get away with the comfortable version of the story or the easy way out. Then explain your hardest current decision to them, out loud or on paper, and look for the weak point: the place where the logic skips a step, or depends on them not asking the obvious question. That weak point is where character collapses and the drift lives.

Run this test quarterly, on a strict schedule, regardless of how the last 90 days felt. The test exists for the decisions that feel fine, because those are the ones eroding you.

There are two more components in the full framework, a growing edge and a transmission plan, and they matter. But the three above are the ones that carry you through a Friday night shock.

You cannot predict which black swan event will hit your business next. All you can do is trust that it will come. Prepare yourself this week by deciding who you will be when it does. Block out an evening, write your code in a language specific enough to test and hand a copy to someone who will hold you to it. The crisis will demand a code from you either way. The only question is whether you built it before the pressure arrived.

On the evening of Friday, March 14, 2025, the White House issued an executive order that listed the Community Development Financial Institutions Fund (CDFI) among federal entities to be eliminated to the maximum extent allowed by law. My phone lit up, and my inbox was flooded within the hour. I have the privilege of serving as the CEO of B:Side Capital, a Small Business Administration (SBA) lender and certified community development financial institution, and the order had just put a large part of my organization directly in its crosshairs. I knew that come Monday morning, I would need to present a clear plan for my team and board members.

I knew that mission-based lenders wouldn’t escape the scrutiny of the newly-formed Department of Government Efficiency (DOGE), but I didn’t think that the CDFI fund would be targeted in such a dramatic manner. I didn’t have a plan in place for this move. Nobody did. What I had in its place was a code, and it turned a chaotic weekend into a sequence of decisions that had been explored long before the crisis hit.

I also teach leadership at Arizona State University, and from both the classroom and the boardroom, the same pattern is impossible to ignore: When real pressure arrives, the values we espouse are too vague to help. Concepts like “Integrity” or “People First” cannot tell you whether to cut staff, go public with your concerns or just quietly wait for the courts. Those words can sit alongside almost any decision without consequence, which is exactly why leaders who rely on them drift from their core beliefs.

It’s easy to talk about values when every decision is straightforward and the numbers are strong. Purpose sounds good on a website and looks good in a pitch deck. But after building more than 22 companies through DRC Ventures, I have learned that values reveal themselves only under pressure, in the moments when the principled choice and the convenient one point in opposite directions.

That is where mission-driven leadership actually lives. Not in the statement you frame on the wall, but in the trade-offs you’re willing to make when nobody would fault you for taking the easier path. Here is how I try to lead when values and convenience collide.

Turn mission into daily decisions

A mission statement that only inspires is failing at its job. Values matter when they shape operations, strategy and the small decisions your team makes when you’re not in the room.

When I built the mission, vision and values for my companies, the hardest part was not making them aspirational. It was making them actionable. Anyone can write something lofty. The discipline lies in balancing ambition with practicality so that the words actually hold up against a budget, a deadline or a difficult call. I did not write them alone either. The process was collaborative and reflective, shaped by colleagues, family and stakeholders whose feedback kept the result grounded in a shared purpose rather than my own preferences.

Those statements now guide everything from the projects I take on to how I lead my team and show up in the communities we serve. That’s the difference between values you announce and values you apply.

Prioritize long-term trust over short-term convenience

Some of the most important decisions I’ve made have come at a real cost. For my products, choosing ingredients and materials that are ethically sourced and environmentally responsible is rarely the cheapest option. It slows things down, and it narrows margins. But every time I’ve chosen the harder, more principled path, it has strengthened the trust people place in what we’ve built.

That trust is not a soft benefit. It shows up on the balance sheet. Accenture reported that 62% of consumers say their purchasing decisions are driven by a company’s ethical values and authenticity. People can tell the difference between a brand that means what it says and one that is merely performing. To me, ethical leadership means weighing the long-term good over the immediate profit and recognizing that every decision touches employees, communities and future generations.

Use values as a filter for growth

Not every opportunity deserves your attention, even if it’s likely to be profitable. One of the most useful things values can do is help you say no. I measure every opportunity against our mission, and if it does not support our core focus on health, sustainability and transparency, we do not pursue it, no matter how attractive it looks in the moment.

This is where purpose earns its keep. Research from NYU Stern Center for Sustainable Business found that products marketed as sustainable grew more than twice as fast as their conventional counterparts over a recent five-year stretch, even while carrying a price premium. When you commit to values that cost something, the market often rewards the consistency rather than punishing the price. That clarity is what keeps a company from chasing every passing trend.

It also helps you tell a passing trend from a real shift. Years ago, I saw the move toward clean and transparent wellness solutions before it became mainstream. What convinced me to commit was not the hype, but the consistency behind it. It was not a moment; it was a movement. I look for that same pattern now: consistency across regions, demographics and time. Longevity is usually tied to a real need, and the trends most worth pursuing tend to reflect a genuine gap or frustration that people are living with every day.

Build partnerships that reflect your purpose

The same filter applies to the people and organizations you choose to work with. The strongest collaborations I’ve been part of have been rooted in shared values, not just shared upside. When a partnership reflects what both sides actually stand for, it creates value that lasts well beyond a single campaign.

I run potential partnerships through a simple framework: passion, audience alignment, local impact and authentic fit. If a collaboration checks those boxes, it tends to serve both the business and the community it touches. And I always start by asking what I can give rather than what I can get. True partnerships uplift both groups, and the long-term relationships they create do far more than any one-time transaction ever could.

Values are built one decision at a time

Values become most visible in the moments when they cost you something: the cheaper supplier you turn down, the lucrative deal that does not fit, the trend you let pass. Those are the decisions customers remember and the ones that compound into a reputation.

Entrepreneurs who stay aligned with their mission, especially when it’s inconvenient to do so, build stronger brands and deeper trust than those who treat values as a marketing tool. Consistency is what turns purpose into credibility. Sustainable, purpose-driven growth is not the product of a single grand gesture. It is built the same way trust is: one honest decision at a time.

It’s easy to talk about values when every decision is straightforward and the numbers are strong. Purpose sounds good on a website and looks good in a pitch deck. But after building more than 22 companies through DRC Ventures, I have learned that values reveal themselves only under pressure, in the moments when the principled choice and the convenient one point in opposite directions.

That is where mission-driven leadership actually lives. Not in the statement you frame on the wall, but in the trade-offs you’re willing to make when nobody would fault you for taking the easier path. Here is how I try to lead when values and convenience collide.

Turn mission into daily decisions

A mission statement that only inspires is failing at its job. Values matter when they shape operations, strategy and the small decisions your team makes when you’re not in the room.

Ten years ago, Kelan and Brittany Kline faced a problem. The then-newlyweds were working jobs that left them with little time together and juggling about $40,000 in student loan debt. 

Their situation was hardly unusual: Americans ages 25 to 34 carry an average student loan balance of about $33,271, according to Federal Reserve data cited by CNBC.

The Klines met in high school in Rochester, New York, and began dating in ninth grade. Since those early days, they found jobs that yielded reliable paychecks: Kelan worked as a jail deputy and Brittany as an elementary school teacher. However, neither of them felt that they had much control over their money or their schedules. 

“We were working opposite shifts,” Kelan recently told Business Insider. “We never got to see each other.”

One evening, the couple decided to confront the pressure head-on over dinner. “We sat down and said, ‘This is not working,’” Kelan told Business Insider. “We kind of just had this brainstorm of, ‘What’s working? What’s not working? Where are our finances at?’”

That conversation became a turning point. The Klines started a personal finance blog, The Savvy Couple, in 2016. It later grew into a seven-figure online business and eventually gave both of them the option to leave their jobs.

The couple told Business Insider that their household net worth, including the estimated value of their businesses, investments and primary home, topped $1 million in 2020. 

How they did it

For the Klines, financial independence did not start with investing more or cutting every expense. It started with defining what they wanted their lives to look like and creating a plan to make it happen.

If we could wave a magic wand, what would our ideal lifestyle look like? Kelan asked at the time. When they tried to articulate their “ideal lifestyle,” they found that they both wanted more time together and flexibility. 

“I was after time freedom,” Kelan said. “I was so sick and tired of someone else telling me when to come to work, forced overtime and denying my vacation.”

Brittany added that “getting on the same page is what made us successful.”

The couple brainstormed how to get more time freedom. They settled on a website. “With an online business, it’s unlimited scalability because you’re reaching the entire world,” Kelan said.

The couple ultimately chose to start a personal finance blog, drawing on their existing interests and experience. Brittany had long been focused on budgeting and saving, while Kelan had tried side hustles, including buying and reselling products on eBay.

The business did not take off immediately. It took nearly a year for the blog to generate any revenue at all, and even then, earnings for the first year totaled just $50.

Since then, their revenue hit $1.3 million in 2023 and $1.1 million in 2024, per Business Insider. 

Kelan’s advice for future entrepreneurs is that they should start their businesses before they feel ready. “The action-takers are money-makers,” he said.

Ten years ago, Kelan and Brittany Kline faced a problem. The then-newlyweds were working jobs that left them with little time together and juggling about $40,000 in student loan debt. 

Their situation was hardly unusual: Americans ages 25 to 34 carry an average student loan balance of about $33,271, according to Federal Reserve data cited by CNBC.

The Klines met in high school in Rochester, New York, and began dating in ninth grade. Since those early days, they found jobs that yielded reliable paychecks: Kelan worked as a jail deputy and Brittany as an elementary school teacher. However, neither of them felt that they had much control over their money or their schedules. 

Our most treasured family activity is traveling in our RV. Each year, I turn off my computer, put my phone on do-not-disturb, and we hit the open road. After days of interstate travel, my favorite part is coasting up or down an off-ramp. 

Whether my children are sleeping, playing video games or simply bothering each other, the deceleration changes the mood in the RV. Faces press against windows. Excitement builds.  

That excitement builds because we’ve spent months planning the trip, hyping up the destination.  

Imagine if we hadn’t. 

Imagine if we had just thrown clothes in a duffel bag, not knowing if we’re headed to the desert or the mountains. 

Imagine if we had three kids in the back, not knowing whether they had days of stream exploration or history museums ahead of them. 

Imagine if we arrived at a destination, planning to eat out, only to find the nearest restaurant is a gas station/diner combo 40 miles away. 

While there’s a great deal of excitement that can be gained from hitting the open road and not knowing what comes next, there’s an even higher risk that you won’t like what you find on the other side. Without the proper planning — and communication — the kids in the back of the RV can quickly become your biggest critics. 

If you’re a business owner, that interstate off-ramp is your business exit. It’s not your destination, but with proper planning, you can be excited enough to press your face up against the glass and anticipate what comes next. 

You can’t exit your business until you exit your identity 

There are three areas of readiness that you must pay attention to when planning for your eventual exit. 

You are likely spending almost all of your time on business readiness. As a business owner, that’s the easiest one: driving value in your business so you’re building something someone will eventually want to buy.  

If you’re finding success, you’re likely spending your remaining time on the second area: financial readiness. You’re building the resources to fund your post-exit life. You’ve got a financial advisor, and maybe you even have a “magic number” that tells you an exit will be financially comfortable for you and your family. 

The forgotten area is arguably the most important: personal readiness. Like the big moment of arriving at your destination with excitement, anticipation, and preparation, personal readiness often determines whether an exit feels successful. 

The problem is that, as business owners, we believe our identity is our business. We become so deeply connected to our title, influence, and routine that they become who we are. 

So when the phone stops ringing, weekly touchbases disappear from our calendar, and the business moves on with a new owner, we don’t have any sense of self. 

Cliches are cliches for a reason 

“The journey is the destination.” 

You have to start your personal plan now in order to have a sense of fulfillment post-exit. Whether you believe your exit to be five, 10, or 20 years down the road, a personal plan takes time to execute while you are still in the owner’s seat.  

A personal plan isn’t just how you’ll spend your time post-exit. It’s about identifying your purpose, determining ways to execute it, and planning how you’ll find fulfillment post-exit. 

Wealth can fund your future. 

Golf can be fun. 

But neither can create meaning. 

Invest in what matters 

You wouldn’t start funding your retirement account at 60. 

So why are you investing in yourself so late? 

Here’s how to get started: 

1. Define Purpose: What’s the unique impact you make on the world? How can you use your position as a business owner to start making that impact intentionally?  

2. Cast Vision: Name the ways that you want to fulfill that purpose outside of your business, post-exit. 

3. Take Baby Steps: Get outside of your business now and try out those new destinations. It’s not just a great test of your post-exit life—decentralizing yourself from your business also builds value in it. A potential buyer wants to know that your business isn’t a one-person show. 

4. Enjoy The Compound Interest: Just as small, early investments can compound, taking small steps towards your post-exit fulfillment now can create excitement for your next stage and help you truly identify what makes you feel fulfilled—and what doesn’t. 

5. Don’t Go Solo: Personal plans are complicated, and we’re not always honest with ourselves. Find an advisor—with a Certified Exit Planning Advisor (CEPA^®) credential—to help you build your plan. 

Always keep your face pressed up against the glass 

According to PwC, 75% of business owners deeply regret exiting their business within a year of the transaction. And, according to our own research at Exit Planning Institute, only 59% of owners have a written personal plan. 

That means most business owners don’t know their destination, and even more won’t like what they find when they get there. 

Just like my kids when they are fully prepared and hyped for our epic RV trip, we’re more excited when we know the destination is truly what we want. Investing your time and energy into making sure your destination is the correct one — and planning for that — is the only way we’ll get that “face pressed up against the glass” feeling in our post-exit life. 

Our most treasured family activity is traveling in our RV. Each year, I turn off my computer, put my phone on do-not-disturb, and we hit the open road. After days of interstate travel, my favorite part is coasting up or down an off-ramp. 

Whether my children are sleeping, playing video games or simply bothering each other, the deceleration changes the mood in the RV. Faces press against windows. Excitement builds.  

That excitement builds because we’ve spent months planning the trip, hyping up the destination.  

Every entrepreneur learns to protect the things that keep the business alive. We insure equipment. We back up data. We diversify revenue. But there is one asset most founders never think to safeguard, and it is the one that everything else depends on. Your own mind.

A new clinical phenomenon is forcing that conversation into the open. Across psychiatric wards and emergency rooms in the United States, doctors have started treating a rising number of patients — many with no prior mental health history — who developed paranoid delusions, hallucinations and disorganized thinking after extensive interactions with AI chatbots. Researchers and clinicians have given it a name. They call it AI psychosis.

It is worth being precise about the term. AI psychosis is not a clinical diagnosis. It describes instances where people develop delusions, or have existing delusions deepened, in association with heavy use of chatbots. The label is informal. The cases are not. UCSF researchers documented a 26-year-old woman with no prior psychiatric history who developed delusional beliefs that she could communicate with her deceased brother through an AI chatbot — a case that drew attention precisely because it looked like a new-onset state rather than a relapse.

For business owners, this is not a fringe story about vulnerable strangers. It is a story about a tool many of us now use for hours a day, often alone, often at the exact moments when our judgment matters most.

Why founders are uniquely exposed

Consider the conditions that surround AI psychosis cases, then consider how closely they match the daily life of a founder.

The mechanism researchers point to is design, not malice. A behavior known as sycophancy — in which some models are trained to agree with and validate user responses — leaves them unable to push back against distorted thinking. On top of that, memory features designed to improve the user experience can reinforce a recurring theme across multiple sessions. The result is an assistant that remembers your narrative and keeps agreeing with it.

Entrepreneurs already live in an environment built for exactly this kind of feedback loop. We work in isolation. We are rewarded for conviction. We are surrounded by people who depend on us and are therefore reluctant to challenge us. The founder’s edge has always been the willingness to believe something the market does not yet believe. That same trait, fed by a system engineered to validate rather than question, can curdle into something far less productive.

The contrast with a competent advisor is the whole point. A qualified therapist is trained to support you while gently pushing back, keeping you grounded and asking you to question your assumptions. Most chatbots are tuned to do the opposite. The commercial goal of the companies behind these tools is for you to keep using them, which nudges the models toward agreeing with you like a yes-man. A yes-man is the single most dangerous voice in any founder’s orbit, and now it is available at all hours, infinitely patient and remarkably persuasive.

The fraction is small. The room is enormous.

It is fair to ask how common this really is. The honest answer is that the percentages are low and the absolute numbers are not. OpenAI has estimated that roughly 0.07% of weekly users show possible signs of psychosis or mania during conversations, while 0.15% display indicators of suicidal planning or intent. Against a user base of more than 800 million people a week, a fraction of a percent is a very large room full of people — roughly 560,000 showing signs of psychosis or mania, and 1.2 million with indicators of suicidal intent.

The risk is widening, not narrowing. New voice-first and wearable interfaces remove the small psychological distance that a keyboard preserves. One recent case involved a man who lost his job and became estranged from his family after heavy use of AI smartglasses. The more ambient and conversational these tools become, the more they feel like a relationship rather than a utility.

What protecting your mind actually looks like

None of this is an argument to abandon AI. The same OpenAI research notes that generative AI chatbots can reduce psychiatric symptoms and have genuine therapeutic potential, though much of the evidence is still early and case-based. These tools are extraordinary for analysis, drafting, modeling and pattern recognition. The discipline is in how we use them, not whether we do.

A few practices are worth adopting before you need them.

Treat the chatbot as a research analyst, never as a confidant. It is excellent at retrieving and structuring. It is unqualified to tell you whether your business decisions, your relationships or your sense of reality are sound.

Build deliberate friction around the validation loop. If the model agrees with everything you propose, that is a warning sign about the tool, not confirmation that you are right. Ask it directly to argue the opposite case, and weigh whether it can.

Keep humans in your decision architecture. A board, a peer group, a co-founder, a trusted advisor, a spouse. The people most at risk in the documented cases were the ones talking primarily to a machine. Your insulation is other minds that are willing to disagree with you.

Watch the clock and watch yourself. In some documented cases, symptoms set in soon after extensive use began. Notice when AI conversation is displacing sleep, human contact or daylight — the same metrics you would track for any other operational risk.

And know that the guardrails are still being built. Illinois has already passed a law banning the use of AI in therapeutic roles by licensed professionals while permitting it for administrative tasks. Regulation is arriving, but it will always lag the technology. Your own habits are the only protection available in real time.

The asset worth insuring

We accept, without much thought, that a founder’s physical health is a business risk worth managing. The clearer mind is an even harder asset to replace, and a far quieter one to lose. AI psychosis is an extreme outcome, and most of us will never approach it. But the underlying dynamic — a tireless system designed to agree with us — reaches every founder who opens these tools each morning.

Insure the equipment. Back up the data. And guard the one instrument that built the company in the first place. The market will test your products. Make sure it is still you doing the thinking when it does.

Every entrepreneur learns to protect the things that keep the business alive. We insure equipment. We back up data. We diversify revenue. But there is one asset most founders never think to safeguard, and it is the one that everything else depends on. Your own mind.

A new clinical phenomenon is forcing that conversation into the open. Across psychiatric wards and emergency rooms in the United States, doctors have started treating a rising number of patients — many with no prior mental health history — who developed paranoid delusions, hallucinations and disorganized thinking after extensive interactions with AI chatbots. Researchers and clinicians have given it a name. They call it AI psychosis.

It is worth being precise about the term. AI psychosis is not a clinical diagnosis. It describes instances where people develop delusions, or have existing delusions deepened, in association with heavy use of chatbots. The label is informal. The cases are not. UCSF researchers documented a 26-year-old woman with no prior psychiatric history who developed delusional beliefs that she could communicate with her deceased brother through an AI chatbot — a case that drew attention precisely because it looked like a new-onset state rather than a relapse.

In the early days of building a company, being at the center of everything feels like the job. You make the calls, you solve the problems and you create the relationships. That level of involvement often drives the early wins, which is exactly what makes it so hard to give up. But after launching more than 22 companies through DRC Ventures, I have learned that the same instinct that gets a business off the ground can quietly become the thing that caps its growth.

The hardest transition any founder makes is the shift from being the person who does everything to the person who builds the systems and people that do it better. It means trading control for trust and shifting your energy from operating to developing. Here are five moves you can make to build organizations designed to outlast your involvement in them. 

1. Replace control with trust

Many entrepreneurs equate involvement with value. If we’re in every meeting and copied on every email, we feel essential. But the leader who stays involved in every decision eventually becomes the ceiling the company keeps hitting.

Learning to delegate was one of the most difficult lessons of my career, and it taught me something I have never forgotten: Trust is what empowers people to take real ownership. The most challenging part of moving from founder to CEO was letting go of direct control. My hands-on involvement in daily operations was, at a certain point, the very thing limiting how far we could scale. Growth required me to step back into strategic leadership and let the people around me step forward.

Trust is not an intangible gesture. It’s a structural decision, and the data backs it up. When Gallup studied CEOs of the fastest-growing private companies, it found that those with strong delegator talent generated 33% more revenue than those with limited delegation instincts, yet three-quarters of the entrepreneurs Gallup surveyed had limited-to-low delegator talent. The instinct to hold on is common. Learning to let go is what separates the companies that scale from the ones that stall. When you give capable people genuine ownership, you strengthen the whole organization and free it to grow beyond what any one person could carry.

2. Develop leaders at every level

Strong organizations build future leaders instead of assembling followers. That distinction shapes everything about how a company holds up under pressure and over time. The people you develop into leaders become the multipliers of everything you are trying to build, with managers alone accounting for 70% of the variance in their teams’ engagement. Who you raise up as a leader shapes the experience of everyone who works under them.

Mentorship is how I try to make that real. To me, the primary goal of any mentorship program is growth, both for the individual and for the company as a whole. The focus is on building people up and giving them the tools, perspective and confidence to step into their potential. The clearest sign that it’s working has been watching mentees come back later as mentors themselves. That tells me we’re doing more than developing talent; we’re creating a cycle of people who give back.

How you pair people matters as well. The best mentoring relationships balance alignment and diversity, matching shared values with different perspectives so the relationship can challenge and support at the same time. Done well, this kind of development breaks down silos, smooths out communication gaps and eases the isolation that can creep into fast-paced workplaces.

3. Avoid becoming the bottleneck

A lot of what looks like a growth problem is really a decision problem. When decisions about ownership and accountability get delayed, they pile up into what I think of as “decision debt,” and that debt compounds. Unclear ownership and too much founder involvement create friction that shows up everywhere: slower execution, repeated conversations and a team that waits on you before moving.

The way out is clarity. When responsibilities are clearly defined and accountability lies with specific people rather than routing back through you, execution improves and the bottlenecks start to disappear. Every decision you empower someone else to make is time you get back for the strategic work only you can do. The goal is to stop solving the same problems over and over and start building toward what’s next.

4. Make resilience part of your culture

No matter how strong your systems are, setbacks are inevitable. What separates durable companies from fragile ones is how they respond, and that response is shaped long before the hard moment arrives.

As a leader, your composure sets the emotional temperature for everyone around you. During periods of uncertainty, your team takes its cues from your confidence and steadiness. When you build a culture around adaptability rather than perfection, people stop fearing problems and start solving them. Those organizations recover faster and perform better over time, because resilience is baked into how they work instead of being summoned only in a crisis.

Resilience, like trust and accountability, is a system built on purpose. It’s one more thing that should live in the culture as opposed to in the founder who created that culture.

5. Build something that outlasts you

Leadership is not measured by how indispensable you make yourself. If anything, the opposite is true. The strongest organizations I’ve been part of are rooted in trust, clear accountability and a genuine commitment to developing other leaders.

Businesses that endure are those that empower people and build systems capable of outgrowing any single individual. The decisions you made while you were in the room don’t form your legacy — it’s the people, the culture and the structures you leave behind that keep making good decisions once you’re not there.