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How much does it cost to have fun? That depends on whom you ask — and how old they are. 

Nowadays, more Americans than two decades ago rate their hobbies or recreational activities as “extremely” or “very important” to them, per a recent Gallup poll.

But how much people spend on their preferred hobbies varies significantly across generations. 

A new analysis from Bank of America Institute, which examined credit card data across a three-month moving average to August 2026, explores how Gen Z, millennial, Gen X and Baby Boomer consumers participate in the hobby economy.

Hobby spending rose 7.9% and suggests a rise in “funflation”

Hobby spending rose 7.9% year over year in August, but at more than double the rate of transaction growth, suggesting an uptick of “funflation” hobbies, according to the report.

“Funflation,” a term coined by economists, refers to the rising price of entertainment and experiences that people are willing to pay to make up for lost time during the pandemic. 

On average, Boomers spend more than $200 per person on their hobbies monthly, the study shows. 

Boomers’ hobby spending is right in line with that of Gen X, but notably higher than that of Gen Z and younger millennials, who typically spend about $100 and just over $140 on their hobbies each month, respectively. 

However, older millennials take the top spot for monthly hobby spending, edging past Gen X and Boomers at nearly $220 per person. Researchers believe this may be because older millennials are most likely to be spending on their kids’ hobbies in addition to their own. 

Investing in your hobby could lead to a business opportunity

What’s more, for some people, hobbies evolve from a fun way to pass the time into lucrative business opportunities. 

During the pandemic, nearly 60% of Americans picked up a new hobby, and about half of them turned it into a side hustle to bring in extra cash, according to a survey from LendingTree. 

Earlier this year, Anna Hudick told Entrepreneur about how she turned a jewelry-making hobby into a business at age 58 after retiring from an engineering career. 

Today, Hudick sells her jewelry designs and teaches craft classes, priced between $65 and $75 per person, to introduce the hobby to more people. 

“They’re coming in after work, stressed, and they have two hours where they aren’t tied to their phone or email,” Hudick said. “They just relax. Then by the time they’re done, they’re so happy with what they’ve made. It’s really fulfilling.”

How much does it cost to have fun? That depends on whom you ask — and how old they are. 

Nowadays, more Americans than two decades ago rate their hobbies or recreational activities as “extremely” or “very important” to them, per a recent Gallup poll.

But how much people spend on their preferred hobbies varies significantly across generations. 

At some point, every business owner has looked at a successful company and thought, “I wish I had thought of that.” Maybe it’s Salesforce. Maybe it’s Costco. Maybe it’s Patagonia. Maybe it’s a competitor that seems to have figured something out before everyone else.

The problem isn’t admiration. The problem is where most entrepreneurs focus their attention. We study founders. We listen to podcasts. We read leadership books. We analyze personalities, habits and morning routines. What we don’t study nearly enough are the systems that made those companies successful in the first place. That’s where the real opportunity is.

Several years ago, one of our larger business partners launched a philanthropy initiative that caught my attention. Community involvement wasn’t an occasional activity. It was built into the company’s culture, and it was reinforced by a measurable process. My first reaction was the same one many small business owners have when they see something impressive: “That’s great, but we’re not them.” They were a much larger organization, with resources, budgets and staff we didn’t have. Replicating their program exactly wasn’t realistic. But then I realized I was asking the wrong question. Instead of asking whether we could copy the program, I started asking why it worked.

The answer was simple: It encouraged employees to engage with their communities and consistently rewarded that behavior. We didn’t need the same structure to accomplish the same goal, so we created our own version. Today, we track volunteer hours and reward team members for community involvement. The program looks different because our business is different, but the principle is the same. It’s also a smart investment. A 2024 Deloitte survey of 1,000 U.S. office professionals found that 87% consider workplace volunteer opportunities a factor in deciding whether to stay with their current employer or pursue a new one.

That experience taught me something many entrepreneurs miss. The companies you admire aren’t valuable because of what they do. They’re valuable because of the systems that make their results repeatable.

Most entrepreneurs study the wrong things

We’ve turned many founders into celebrities. We study Steve Jobs’ black turtleneck. We analyze Elon Musk’s work habits. We obsess over leadership styles and personality traits.

Meanwhile, the things that actually drive performance get far less attention: communication systems, accountability structures, documented processes and performance standards. None of those topics makes for an exciting keynote speech. Yet they’re often the reason one company consistently outperforms another. The next time you admire a business, stop asking what makes the founder special. Ask what allows ordinary people inside that company to perform at a high level, again and again.

That’s usually where the lesson lives.

Steal clear communication

One of the biggest differences between large organizations and small businesses is communication. Large companies can’t afford to keep information inside the owner’s head. They answer to shareholders, boards, investors and thousands of employees. Priorities have to be communicated. Expectations have to be documented. Goals have to be clarified.

Small businesses often work differently. The owner knows where the company is headed and assumes everyone else does too. The result is predictable: Team members fill in the gaps with their own assumptions, work gets misaligned and leaders get frustrated that employees aren’t executing a vision that was never clearly communicated.

Here’s a simple test. Ask your leadership team to write down the company’s top three priorities for the next 12 months. The results may surprise you. In a 2015 study of more than 250 companies published in Harvard Business Review, researchers found that only 55% of the middle managers they surveyed could name even one of their company’s top five priorities. And those were larger organizations with formal communication processes in place.

If everyone on your team gives a different answer, you don’t have a people problem. You have a communication problem. The companies we admire create clarity. Small businesses should do the same.

Steal standards, not personalities

It’s easy to admire leaders who make tough decisions, hold people accountable and maintain high expectations, and to assume their success comes down to personality. What often gets overlooked are the standards guiding those behaviors. The strongest organizations define what success looks like before performance becomes a problem. They set expectations, communicate priorities and coach people toward those standards. Most importantly, they address issues when those standards aren’t being met.

That kind of clarity is rarer than you might think. According to Gallup, just 47% of employees strongly agreed that they know what is expected of them at work as of mid-2025. Small business owners often struggle here because accountability can feel personal. You know your employees’ spouses. You know their children. You know what’s happening in their lives. That makes difficult conversations uncomfortable. But avoiding them creates confusion, not kindness.

You can be direct without being harsh. You can hold people accountable without being militant. The best organizations understand the difference.

Steal process discipline

Large companies create structure because they have to. They document workflows, establish procedures and define ownership. Small businesses often wait until they feel bigger to do those things. But structure is often what allows a company to grow in the first place.

If your team can’t answer these questions, there’s work to do: What are our top priorities? Who owns each one? How do we measure success? What process do we follow when problems arise? When those answers are unclear, people spend more time guessing than executing. The businesses we admire remove that uncertainty.

A simple exercise every entrepreneur should try

The next time you find yourself admiring a company, ask four questions:

1. What behavior are they trying to encourage?
2. What system reinforces that behavior?
3. How could I build a smaller version inside my business?
4. How would I measure whether it’s working?

Those questions shift your focus from admiration to implementation. You’re not going to become Patagonia or Salesforce, and the goal isn’t to become the next famous founder. The goal is to identify the systems that help great companies succeed and adapt them to fit your business.

The most valuable things to steal from successful companies are usually hidden behind the scenes.

At some point, every business owner has looked at a successful company and thought, “I wish I had thought of that.” Maybe it’s Salesforce. Maybe it’s Costco. Maybe it’s Patagonia. Maybe it’s a competitor that seems to have figured something out before everyone else.

The problem isn’t admiration. The problem is where most entrepreneurs focus their attention. We study founders. We listen to podcasts. We read leadership books. We analyze personalities, habits and morning routines. What we don’t study nearly enough are the systems that made those companies successful in the first place. That’s where the real opportunity is.

Several years ago, one of our larger business partners launched a philanthropy initiative that caught my attention. Community involvement wasn’t an occasional activity. It was built into the company’s culture, and it was reinforced by a measurable process. My first reaction was the same one many small business owners have when they see something impressive: “That’s great, but we’re not them.” They were a much larger organization, with resources, budgets and staff we didn’t have. Replicating their program exactly wasn’t realistic. But then I realized I was asking the wrong question. Instead of asking whether we could copy the program, I started asking why it worked.

I want to tell you about a puppy.

It was a mixed-breed puppy, which is the dog version of a mystery box (you don’t know exactly what’s inside, and I’m not convinced the dog does either). It was not house-trained. It was also staying at one of my properties, and nobody told me.

Someone snuck it in, so I found out about the puppy around the same time I found out about everything it had done. Those are two things I typically prefer in reverse order. This one chewed through baseboards, ruined floors, and kept going until the bill hit about $7,000. On a rental cash-flowing $300 a month, that’s almost two years of cash flow eaten by a puppy (in the baseboards’ case, literally).

(Before anybody from the rescue world emails me: I’m building a dog-first hotel, and this is a pro-dog article. It’s also an anti-surprise article).

What bugs me is how avoidable most of it was. If that puppy had been disclosed and screened, we’d have known what was coming and planned for it.

Every landlord eventually meets their own version of this puppy, and $7,000 turned out to be the cheap version. The expensive versions come down to what your paperwork can prove, which, for an animal nobody told you about, isn’t much.

You’re Not the Only One Who Got Surprised

PetScreening surveyed 673 property managers and leasing pros for its 2026 State of Pets in Rental Housing report. Unauthorized pets came out as their top pet problem. 

The same report found that only 43% of renters say they have a pet, compared with 71% of U.S. households, according to the American Pet Products Association. That’s a 28-point gap. Either renters are less into pets than everybody else, or plenty of dogs are living off the books, which is the report’s theory too.

Usually, nobody’s running a con. Someone adopts a puppy in month seven and never thinks to call you. A girlfriend’s dog comes over for a weekend in February and is somehow still there at Easter.

The Bills Come Later

Insurance usually won’t touch pet damage to the unit. Standard renter’s policies exclude it, and no adjuster in America considers a puppy an act of God (except maybe Air Bud). Chewed baseboards and a carpet that smells like a kennel get filed under preventable wear. That leaves your security deposit doing a job plenty of landlords assume insurance is doing.

Bites are the bigger number. Insurers paid $1.86 billion on 28,450 dog-related injury claims in 2025, averaging $65,450 per claim, according to the Insurance Information Institute and State Farm. On that same $300-a-month cash-flowing rental, a single average claim eats up about 18 years of cash flow.

The tenant’s renter’s policy is supposed to pay for a bite first. Plenty exclude certain breeds or any dog with a history of bites, and it gets messier if the tenant never told their insurer either. If you didn’t know the dog existed, you never asked for proof of coverage. Your own landlord policy may have animal exclusions, too, and it’s better to find that now than in a denial letter.

Disputes come down to paperwork

I’ll use Texas as an example because that’s where my properties are. Once a tenant moves out and provides a forwarding address, Property Code 92.103 starts a 30-day clock for the deposit refund. Anything you keep needs a written, itemized list under 92.104, and normal wear and tear doesn’t count. 

If they sue, 92.109 puts the burden on you to prove the deductions were reasonable. Miss the 30 days and the law presumes bad faith. That clock does not care how busy your month was. A bad-faith finding costs $100 plus three times what you wrongly kept, plus the tenant’s attorney’s fees.

Say you keep $600 for floor damage, your list goes out on day 34, and a judge rules against you. Now you owe $1,900, plus a lawyer you never hired.

If the animal were never disclosed, you would have even less to work with. There’s no pet addendum or description of the animal, and nothing signed showing the tenant knew your rules on pet sitting or adopting mid-lease. “I’m pretty sure those scratches weren’t there” won’t carry much weight when the burden of proof is on you.

(Outside Texas? Your state has its own deadlines and penalties. Look them up before a move-out forces the issue.)

That neighbor email is Exhibit A

In Texas, owning the house doesn’t automatically make you responsible for a tenant’s dog. Liability usually turns on what you knew about the dog being dangerous and whether you did anything once you knew.

Now picture the neighbor’s email saying the tenant’s dog charged her kid at the mailbox again. That email is evidence you knew. You can’t unread it. Attorneys in bite cases love a written complaint like that, especially next to a lease rule nobody enforced.

Three Houses, Three Rulebooks

Nobody sets out to run three different pet policies. It happens one house at a time. 

• House A has the good pet addendum and move-in photos. 
• House B has a one-line “no pets” clause. 
• House C is on a lease somebody downloaded in 2019. 

Each one looks fine on its own. Together, they read like a group project where the members never met.

That works until those leases have to back each other up in front of a judge or a fair housing investigator. They notice when similar situations got handled differently.

Assistance animals and ESA’s make this more urgent. HUD withdrew its assistance animal guidance in September 2025. A May 22, 2026, memo narrowed federal enforcement to animals individually trained for disability-related work or tasks. State laws didn’t change; residents can still sue on their own, and attorneys are telling landlords to be careful with denials. 

With the federal approach changing twice in eight months, this is not the place to freestyle. Have an attorney in your state review how you handle these requests.

One Pet Process for Every Door

The fix is boring: Run the same pet process on every property and keep the record. It’s free for housing providers, and more than 28,000 property management firms and communities use it. On a long-term rental, it looks like this:

1. Everyone Goes Through It: That includes residents with no animals. Their profile is free, takes a few minutes, and has them acknowledge your rules on pet sitting, visiting pets, and getting a pet mid-lease. That’s the signature you’ll want when the weekend dog is still around at Easter.
2. Every Animal Gets a File: Pet owners upload photos and vaccination records, then attest to your policies and their pet’s history, including bites. You get a FIDO Score, a paw rating of the pet’s housing risk built from more than 35 data points. It won’t make the decision for you, but it helps you make it the same way at every property.
3. Assistance Animals and ESAs Get Their Own Lane: Requests go to PetScreening’s in-house review team, which verifies the documentation with the healthcare provider. Residents don’t pay a profile fee, and you’re not improvising on a legal question that’s still moving.
4. Re-Up at Renewal: Have every resident refresh their profile every year. That’s how you meet the new puppy at renewal instead of at move-out.
5. One Dashboard for Every Door: Every animal and signed policy lives in one place, and it integrates with property management software, including Buildium, Rent Manager, AppFolio, and Yardi. When the neighbor emails, you can pull up that dog’s file instead of guessing.

If a property manager runs your doors, try this: Pick three random units (not the three you know are fine) and ask for the animal record on each. If it takes more than a few minutes, that’s your gap.

Back to That Puppy

None of that $7,000 was the puppy’s fault. A rescue that isn’t house-trained yet is just being a puppy. The problem was that no one on our side knew it was there, so no one had a plan.

So yes, still pro-dog, still anti-surprise. Most residents with pets will do this right if you give them a clear, single process, and that costs way less than the surprise.

Get the animals on paper before you have a puppy that has an appetite for baseboards.

When growth slows, there is no shortage of advice about what to do next. Post more on LinkedIn. Invest in SEO. Run paid ads. Rewrite your homepage. Improve onboarding. Change your pricing. Launch a referral program. Hire a salesperson.

But they all have the same problem: They start with a solution before you understand the problem. 

If your company isn’t growing as quickly as you expected, something is preventing potential or existing customers from taking the actions you need them to take. The question is: Why?

Before deciding which growth tactic to try next, I would start there.

Growth metrics tell you what is happening, not necessarily why

Most companies have enough data to identify where their funnel isn’t performing.

You might know that only 2% of website visitors start a trial. You might know that 80% of those trials never become paying customers. Maybe your sales team loses half of its qualified opportunities. Or perhaps customers sign up but never adopt enough of the product to stick around.

Those numbers tell you something important. They tell you where to look. But they don’t necessarily tell you what to fix.

Imagine that 1,000 people visit your website every month, but only 10 request a demo. There are dozens of possible explanations. 

You might be attracting the wrong visitors. Your ideal customers might not immediately recognize that the product is for them. You might be describing a problem they don’t consider important. They might understand the value but not believe your claims. They might think the product is too expensive. They might not want a demo. Or they might simply have unanswered questions preventing them from taking the next step.

The metric is the same in every scenario: 1% visitor-to-demo conversion. But the appropriate solution is completely different. That is why jumping from a disappointing metric directly to a growth tactic can be so inefficient.

The same growth problem can have completely different causes

Consider another common SaaS problem: Lots of people start a free trial, but few become paying customers.

What should you do? A common recommendation might be to improve onboarding. That sounds reasonable. But first, consider some of the reasons people might not be converting.

Maybe your marketing attracts people who were never likely to buy. Maybe users sign up expecting a capability your product doesn’t have. Maybe they can’t figure out how to use the product. Maybe they understand how to use it but never experience enough value during the trial. Maybe they love the product but can’t get their team on board. Maybe they can’t justify the price. Or perhaps they simply aren’t ready to buy yet.

If the problem is usability, improving onboarding could work. If the problem is that you’re attracting the wrong people, it probably won’t. If the problem is missing functionality, a better nurture sequence probably won’t solve it either.

This is why I think of growth problems as discovery problems before they become execution problems.

You need to understand the cause before you can confidently choose the treatment.

Start with the customer behavior you need to change

Instead of beginning with “What should we try next?” start by identifying the behavior that isn’t happening.

For example:

• Your target buyers see your ads but don’t click.
• Website visitors don’t start trials.
• Website visitors don’t book demos.
• Trial users don’t become paying customers.
• Demos don’t convert to qualified opportunities.
• Qualified opportunities don’t close.
• New customers don’t adopt important features.
• Existing accounts don’t add more users.
• Customers cancel.

These are much more useful starting points because they force you to focus on a specific customer behavior. Then ask a simple question: Why aren’t these customers doing what we expected them to do?

That changes the growth conversation. Instead of brainstorming tactics, you start by investigating causes. And one of the most useful ways to investigate those causes is to talk to the people who actually made the decisions.

Ask customers what happened

Analytics are incredibly useful for understanding behavior. They can show you where people drop off, which features they use, how often they return, which campaigns produce signups and how different customer segments behave.

But analytics can’t always tell you what was happening in someone’s head when they made a decision.

That is where customer interviews can help. Suppose you want to understand why trial users aren’t buying. Talk to people who recently completed a trial but didn’t convert.

Ask what originally caused them to look for a solution. Ask what they hoped your product would help them accomplish. Ask what they expected when they signed up. Walk through what happened during their trial. Find out what they liked, what confused them, what disappointed them and what ultimately prevented them from purchasing.

Don’t ask, “Would you have bought if our onboarding were better?” That introduces your hypothesis into their answer.

Instead, reconstruct what actually happened. The same approach works throughout the funnel.

If target buyers aren’t responding to your marketing, talk to people who resemble the audience you’re trying to reach and understand how they think about the problem you’re solving. If qualified prospects aren’t buying, interview lost opportunities and find out how they evaluated the decision.

If customers aren’t expanding, talk to accounts that considered adding users but didn’t. If customers are leaving, talk to people who recently canceled.

You’re looking for the gap between what you expected customers to do and what they actually did. Then you’re trying to understand why that gap exists.

Look for patterns, not individual requests

One customer interview shouldn’t determine your growth strategy.

Customers have individual preferences, circumstances and opinions. Someone might dislike your pricing model. Another might ask for a particular integration. Someone else might want a completely different feature.

The value comes from patterns. If six of eight lost prospects tell you they couldn’t confidently explain the product’s value to the person approving the purchase, you may have discovered a champion enablement problem. If trial users repeatedly tell you they signed up but didn’t know what they were supposed to accomplish first, you may have found an onboarding problem.

If customers who churn consistently tell you they stopped using the product months before canceling, you may have discovered an adoption problem that begins much earlier in the lifecycle. Those findings give you something much more useful than a list of growth ideas.

They give you evidence about which problem deserves to be solved and strong clues into how to solve it.

Then choose the tactic

This is where tactics become valuable. Once you have evidence about what is preventing customers from moving forward, you can decide what intervention is most likely to change their behavior.

• Maybe the answer really is a new onboarding flow.
• Maybe it’s different positioning.
• Maybe you need stronger customer proof.
• Maybe you need to change who you’re targeting.
• Maybe sales needs better tools for helping a champion build internal consensus.
• Maybe customers need more support during their first 30 days.
• Maybe the product is missing something important.

You still have to make a judgment. Customer interviews won’t hand you a perfect growth plan, and qualitative research should usually be considered alongside funnel data, product analytics and other evidence.

But now your growth ideas are responding to something you have observed rather than something you have assumed. That is a very different way to make growth decisions.

Diagnose before you prescribe

There will always be another growth tactic to try. That’s part of what makes growing a company difficult. There are hundreds of things you could be doing at any moment, and many of them sound plausible.

The challenge is figuring out which problem is actually preventing growth and which action is most likely to address it. So the next time a funnel metric disappoints you, resist the temptation to immediately ask what tactic you should try.

1. Start with the behavior.
2. Identify the people who aren’t doing what you expected.
3. Talk to them.
4. Understand what happened.
5. Look for patterns.

Then decide what to change. Because the fastest route to growth may not be trying more things. It may be understanding why the things you need customers to do aren’t happening in the first place.

When growth slows, there is no shortage of advice about what to do next. Post more on LinkedIn. Invest in SEO. Run paid ads. Rewrite your homepage. Improve onboarding. Change your pricing. Launch a referral program. Hire a salesperson.

But they all have the same problem: They start with a solution before you understand the problem. 

If your company isn’t growing as quickly as you expected, something is preventing potential or existing customers from taking the actions you need them to take. The question is: Why?

Early-stage founders love to talk about vision. I get it. Vision is exciting, and it is often the reason a company exists in the first place. Still, when I sit across from a founder, I usually learn more from their operating habits than from their headline.

I have heard plenty of polished pitches over the years. The founders who earn my attention are usually the ones who show me a simple system for execution. They know what matters this week, who owns it, how progress gets tracked, and when the team will review it again. That may sound basic, yet basic wins more often than a grand speech.

My father taught me that lesson long before I worked in venture. He came from very little, built from scratch and expected the people around him to care deeply about the details. But one thing he said really stayed with me, and that’s if you expect other people to care about your company, you had better care first.

Founders who gloss over the details usually reveal something larger. They want the title of a founder more than the work of actually building. You can’t expect the investors to care more about your company than you. And that shows up in how you organize the details.

Care shows up in the calendar

One of the clearest signals of discipline is how a team runs its week. I want to see a recurring execution meeting with a fixed rhythm, a short agenda and real owners on every priority. A good weekly meeting does not need fancy software or a consultant. It needs structure. The best teams I meet can answer four questions quickly. What were the top priorities last week? What moved forward? What slipped? What matters most before the next meeting? If a founder cannot answer those questions with clarity, then the team is probably drifting.

I think about punctuality the same way. People love saying they arrived right on time, as if that proves seriousness. To me, arriving exactly on time often says the opposite. Life happens. Traffic happens. Tech issues happen. People who truly care usually build margin into the day. That mindset carries into company building. Great founders prepare before the meeting starts. They do not show up and decide what matters in real time.

Keep the weekly plan painfully simple

Founders often assume better execution means more process. Usually, it means less. Early teams rarely need layers of bureaucracy. They need one page.

I like a one-page weekly plan because it forces clarity. The company mission may be broad, yet the week should feel specific. List the three to five priorities that matter most. Name the owner beside each one. Add a target date or metric. Then review the same sheet at the next meeting.

That simple habit does two things. First, it exposes confusion early. Second, it makes accountability feel normal instead of personal. A missed priority no longer becomes a dramatic confrontation. It becomes a visible item the team can address, learn from and reset.

Too many founders confuse motion with traction. They stay busy, take meetings, answer messages and jump between fires. Then Friday arrives, and nobody can say what actually moved. A one-page plan gives the week a spine.

Metrics need owners, not admirers

Another thing I watch closely is how founders talk about metrics. Vague language tells me very little. I don’t want to hear that revenue is improving or the pipeline looks strong. I want to know who owns revenue, what the customer pipeline looks like, where deals are stalling and what number the team is trying to move next.

A young company does not need 50 dashboards. It needs a handful of numbers that matter and a person responsible for each one. Revenue, pipeline, customer conversations, burn, runway, hiring or product releases can all matter depending on stage. What matters most is ownership.

When no one owns a metric, everyone gets to admire it from a distance. That helps nobody. A founder should be able to say, “Sarah owns the pipeline. James owns product delivery. I own fundraising and key hires.” Clear ownership creates clear conversations.

Investor updates are a discipline tool

Many founders treat investor updates like a favor. I see them as an operating tool. A solid monthly update forces a founder to slow down, look at the business honestly, and decide what belongs in the headline, what belongs in the lowlight, and what support is needed next.

One of the better update formats I have seen is also one of the simplest. Share key metrics, cash in the bank, runway, major wins, major misses, asks and priorities for the next month. That is it.

I have also seen the other side, and it is painful. I have backed founders who chased the investment hard, then went silent after the investor made the deposit. In one case, I learned through LinkedIn that a founder had moved on to a new job while investors were still waiting for a clear update on the company. That kind of behavior kills trust fast. Bad news doesn’t ruin a relationship, but silence does.

Accountability works best when it feels normal

The strongest teams make accountability part of the culture before a crisis arrives. They revisit priorities every week. They schedule standing check-ins. They create a place where asking for help feels responsible rather than weak.

That matters because founders carry a lot. There will be weeks when the plan slips, the hire falls through, or the customer says no. A disciplined operating cadence gives the team a way to recover without panic. It turns execution into a repeatable practice.

If you are building an early company, start here. Set a weekly execution meeting. Build a one-page plan. Assign clear owners to the few metrics that matter most. Send a monthly investor update that tells the truth. Then repeat. Vision opens the door. Discipline keeps it open. Traction usually comes from founders who care enough to do the simple things every single week.

Early-stage founders love to talk about vision. I get it. Vision is exciting, and it is often the reason a company exists in the first place. Still, when I sit across from a founder, I usually learn more from their operating habits than from their headline.

I have heard plenty of polished pitches over the years. The founders who earn my attention are usually the ones who show me a simple system for execution. They know what matters this week, who owns it, how progress gets tracked, and when the team will review it again. That may sound basic, yet basic wins more often than a grand speech.

My father taught me that lesson long before I worked in venture. He came from very little, built from scratch and expected the people around him to care deeply about the details. But one thing he said really stayed with me, and that’s if you expect other people to care about your company, you had better care first.

For most of marketing history, a company would only chase you so far. Another sales call took a salesperson’s time. Another direct-mail piece cost money to print and mail. Another ad required more media spend.

Those constraints weren’t good, exactly, but they created natural stopping points: At some point, you had to decide whether pursuing someone was still worth it.

Marketing technology has steadily removed those stopping points.

Today, someone visits your website and gets added to a retargeting audience. They download something and enter an email sequence. They click an email and their lead score goes up.

And once all of that machinery starts running, it can be surprisingly difficult to get it to stop. Now AI is removing even more friction. It can create variations of ads and emails in seconds, personalize messages and recommend or execute what happens next.

That’s why I think one of the most underrated marketing skills today is knowing when to stop.

A signal isn’t the same thing as intent

People like personalization when it works. A Boston Consulting Group study of more than 23,000 consumers found four in five were comfortable with personalized experiences. The same study found two-thirds had recently run into personalization that was inaccurate or invasive — experiences that pushed people to unsubscribe, disengage or simply not come back.

Think about your own behavior online. You look at patio furniture you might buy next summer. You research a hotel for a trip you ultimately don’t take. Then the ads start.

One innocent click has somehow convinced a company’s marketing system that you have developed a deep and enduring passion for patio furniture.

A recent Site Impact survey of U.S. adults who regularly consume personalized marketing found that 57% are frequently targeted for products they looked at once but never seriously considered buying. More significantly, 43% said they have stopped considering or purchasing from a brand because its personalization was repetitive, too personal or simply wrong.

We collect enormous numbers of signals, but signals aren’t instructions. Visiting a page doesn’t necessarily mean someone wants the product. Downloading a report doesn’t mean they’re ready to talk to sales. And something a person wanted six months ago isn’t necessarily something they want today.

Even the advertising platforms have a stop button

There’s a reason digital advertising platforms give marketers tools to control how often people see their ads. Google Ads, for example, allows advertisers to set frequency caps for display and video campaigns.

That feature reflects a basic tension. You need repetition for someone to remember you. But at some point, another impression isn’t accomplishing anything. A 2024 paper in Decision Support Systems modeled consumer “ad fatigue” and produced an inverted-U curve: Advertising generates increasing returns up to a point, then diminishing or negative ones.

There’s no universal number where that happens. Five impressions might be too many in one situation and nowhere near enough in another, which is precisely why judgment matters.

Your customer sees one company

This can get harder because most companies don’t actually have one marketing system. They have an email platform, CRM, advertising platforms, SMS software, social media, sales automation and customer service software. Each has its own rules and its own view of the customer.

The customer doesn’t care. They don’t think, “That’s only my fourth marketing email because the other three came through different channels.” They think, “Why won’t this company leave me alone?”

That’s why stopping rules need to operate across the customer relationship. If someone buys the product, stop advertising that product to them. If someone hasn’t opened the last 15 emails, reconsider sending number 16. If a prospect tells a salesperson they’re not interested until next year, your automated marketing shouldn’t spend the next six months pretending that conversation never happened.

Sometimes the smartest marketing action is no action.

AI changes the economics of persistence

Until recently, even automated marketing had constraints: Humans still had to write the emails, develop the creative and build the sequences. Generative AI removes most of that friction. That can make good marketing dramatically more efficient. It can also make bad marketing relentless.

And consumers have a limit even when the personalization is right. Adobe’s 2026 consumer research found that 45% of customers would disengage from a brand if they received too many promotions, even relevant ones.

The marginal cost of another message keeps falling. The cost to the customer’s patience doesn’t.

Build a stop system, not just a send system

As you add more automation and AI to your marketing, I think every entrepreneur should ask four questions:

1. How strong was the original signal? Someone requesting a demo is telling you something very different from someone spending 30 seconds on a product page. Don’t treat curiosity as intent.
2. How old is the signal? Customer data should depreciate. A search from yesterday might tell you something important. A search from six months ago may tell you almost nothing. Your marketing system needs a forgetting function.
3. How much have you already said? Look across channels rather than evaluating each one separately.
4. What should make us stop? Marketers spend enormous time designing triggers: If the customer does X, we do Y. Put equal thought into suppression triggers. A purchase, silence, a service problem or a plain expression of disinterest should change what happens next.

None of this means giving up easily. Repetition works. Follow-up works. Any salesperson can tell you that a “no” sometimes becomes a “yes” months later. But there’s a difference between persistence and refusing to take a hint.

Technology has given entrepreneurs extraordinary tools for figuring out what message to send next. The businesses that use them best won’t be the ones that send the most messages. They’ll be the ones that know when they’ve said enough.

For most of marketing history, a company would only chase you so far. Another sales call took a salesperson’s time. Another direct-mail piece cost money to print and mail. Another ad required more media spend.

Those constraints weren’t good, exactly, but they created natural stopping points: At some point, you had to decide whether pursuing someone was still worth it.

Marketing technology has steadily removed those stopping points.

Some businesses sell products that customers already understand. Others have to explain the category before they can explain why their company is the right choice.

I operate in one of those industries. Most people have seen window film, but many do not know how solar control window film differs from decorative film, privacy film or security window film. They may also associate window tinting only with cars, rather than home window tinting or commercial window film for buildings. Before customers can evaluate a proposal, they first need to understand what the product can do and can’t do and which option fits the problem they are trying to solve.

This challenge is not unique to the window film business. Technology companies, financial services firms, healthcare providers, specialty contractors and many other businesses offer products or services that are difficult to evaluate from the outside. In these industries, customers are often being asked to make a significant decision without having the technical knowledge that the seller uses every day.

That knowledge gap can create hesitation. It can also tempt a business to sell more aggressively. In my experience, pressure does not resolve confusion — clear education does.

Confusion changes how customers evaluate value

When customers do not understand the differences between their options, price often becomes the easiest way to compare them. Two proposals may appear similar even when the products, installation requirements or expected outcomes are very different. If no one explains those differences clearly, the customer may reasonably assume that the lowest price represents the best value.

This is why education is not separate from selling in a specialized industry. It is a necessary part of helping customers make a useful comparison.

The conversation should begin with the customer’s problem, not the company’s product catalog. A homeowner may be dealing with rooms that become uncomfortably hot in the afternoon. A property manager may want to reduce glare in an office, improve privacy in a conference room or add another layer of protection to existing glass. Those customers are not initially looking for a lesson on film construction. They want to know whether their problem can be solved.

Once the goal is clear, the business can explain the available options in terms that connect directly to that outcome. Technical knowledge still matters, but it becomes valuable to the customer only when it is translated into relevance.

Leaders in any industry can apply the same approach. Listen for what the customer wants to change or improve, then explain the solution through that lens. A buyer does not need to understand every technical detail, but they should understand why a recommendation makes sense for their situation.

Honest limitations are part of good education

Businesses naturally want to emphasize what their products can do. The harder, and often more important, conversation is explaining what they cannot do.

In specialized industries, broad terminology can create expectations that a product or service was never designed to meet. For example, customers exploring safety and security window film need a clear explanation of how the system is intended to perform and why no responsible company should make guarantees that the product can’t support. 

Every technical business has its own version of this issue. Software has implementation limits. Financial products involve risk. Construction projects can reveal hidden conditions. Healthcare services do not produce identical outcomes for every person. Avoiding these realities may make an early sales conversation easier, but it often creates disappointment later.

Trust grows when a company is willing to say that a solution is not right for a particular situation. That honesty may cost a transaction, but it protects the customer relationship and the company’s reputation. It also helps the right customers move forward with realistic expectations.

Education should therefore include tradeoffs, not just benefits. Customers should understand why one option costs more, what they gain from it and when the added expense may not be necessary. Recommending the right solution instead of the most expensive one shows that the company is focused on the outcome, not simply the size of the sale.

The people delivering the work complete the lesson

Customer education cannot belong only to the marketing department or sales team. In a service business, the employees performing the work often have the greatest credibility because customers can see their expertise in action.

Our installers are the final and most important impression customers receive from our company. They may answer questions about care, appearance, and what to expect after installation. Their technical ability is critical, but so is their ability to communicate clearly and without unnecessary jargon. A strong installation paired with a dismissive interaction can still weaken the customer’s overall experience.

This is true well beyond the window film industry. Technicians, consultants, healthcare professionals, delivery teams and other frontline employees frequently become the most trusted representatives of a company. Their communication can either reinforce what the customer was promised or create doubt at the moment the business should be building confidence.

Leaders should teach employees the reasoning behind common questions and know when to involve an expert instead of relying on scripts. Frontline employees also know where customers get confused, so their feedback should guide training materials. 

Clarity creates confidence

Some entrepreneurs worry that educating customers will make the sales process longer. Poor education can certainly overwhelm buyers with information they don’t need. However, good education does the opposite. It answers the questions preventing a decision and helps customers understand whether the solution is right for them.

The goal is not to turn every buyer into an expert. It is to replace uncertainty with enough clarity for the customer to make a confident choice.

In technical service businesses, that confidence depends on both the product and the people delivering it. A customer may begin by searching for residential window tinting, commercial window film or a way to reduce heat, but what they ultimately need is confidence that they understand the recommendation and can trust the team carrying it out.

When customers are confused, clarity is the answer. The companies that teach well do more than close sales. They create stronger relationships with customers and a reputation that competitors can’t copy. 

Some businesses sell products that customers already understand. Others have to explain the category before they can explain why their company is the right choice.

I operate in one of those industries. Most people have seen window film, but many do not know how solar control window film differs from decorative film, privacy film or security window film. They may also associate window tinting only with cars, rather than home window tinting or commercial window film for buildings. Before customers can evaluate a proposal, they first need to understand what the product can do and can’t do and which option fits the problem they are trying to solve.

This challenge is not unique to the window film business. Technology companies, financial services firms, healthcare providers, specialty contractors and many other businesses offer products or services that are difficult to evaluate from the outside. In these industries, customers are often being asked to make a significant decision without having the technical knowledge that the seller uses every day.

Google’s latest workforce bet is helping veterans enter the skilled trades.

According to a recent report from Fox Business, Google is partnering with veteran groups to tackle the skilled trades worker shortage. The tech giant wants to help 25,000 veterans transitioning from service and military family members launch careers in the skilled trades. It’s unclear how much Google is investing in the initiative. 

The effort will offer hands-on pre-apprenticeship training, career coaching and job-placement support for roles including electricians, pipefitters and project managers.

Google’s new workforce initiative will enlist the help of national organizations serving veterans, including Hiring Our Heroes, Student Veterans of America (SVA), and Home Builders Institute. 

The program arrives as demand for trade workers accelerates alongside the buildout of AI data centers and related infrastructure. There is a nationwide skilled labor shortfall. A report from Bring Back the Trades revealed that there will be 1.4 million trade jobs unfilled by 2030.

Google data-center operations leader Tim Chadwick, a 21-year U.S. Navy veteran, said in a blog post that the initiative will make civilian-career transitions easier for veterans. 

Chadwick, who oversees data-center operations across Ohio and Indiana, said “hundreds of thousands” of skilled-trades jobs remain open nationwide. He added that the initiative was a response to that workforce need. It is also a way to steer veterans and military families toward durable, “high-growth careers” like his own with long-term earning potential.

“But beyond just the growing need, these roles also make the most of the kinds of skills veterans and military families know better than anyone — skills like problem-solving under pressure, teamwork, and getting a job done right,” Chadwick stated.

Nationwide, the latest U.S. Bureau of Labor Statistics data show that electricians earned a median annual wage of $63,190 in May 2025, while plumbers, pipefitters and steamfitters earned a median of $63,800.

Project management specialists, a broader occupational category that can include construction and infrastructure project roles, earned a substantially higher median of $102,320 annually.

The commitment expands Google’s broader trades-training push. The company recently joined BlackRock, Ford and Carhartt in June to launch the Alliance for America’s Skilled Trades, which aims to train one million workers by 2030, and previously committed funding for AI-enabled training tools and veteran-focused career certificates.

Cory Boatwright, president and CEO of SVA, told Fox Business that the organization’s collaboration with Google included 22 roundtable discussions across 11 states. They sought a clearer picture of what veterans want as they prepare for civilian life. 

He said that the consistent message was that many are looking for more accessible routes into purposeful careers. 

Boatwright said SVA is also taking a broader view of who qualifies as a “student veteran.” Rather than limiting the term to people pursuing traditional college degrees, the organization now includes veterans seeking any form of continued education, from professional certificates to training in the skilled trades.

“The student decides the path and what is meaningful to them,” he said.

Google’s latest workforce bet is helping veterans enter the skilled trades.

According to a recent report from Fox Business, Google is partnering with veteran groups to tackle the skilled trades worker shortage. The tech giant wants to help 25,000 veterans transitioning from service and military family members launch careers in the skilled trades. It’s unclear how much Google is investing in the initiative. 

The effort will offer hands-on pre-apprenticeship training, career coaching and job-placement support for roles including electricians, pipefitters and project managers.

Over the next decade, up to $5 trillion in U.S. businesses is expected to change hands.

Most of that value sits with baby boomer owners aging out of companies they spent decades building, ready or not. On the buying side, private equity firms are sitting on about $1.2 trillion in uninvested buyout capital, nearly a quarter of it held for four years or more and now under real pressure to be deployed. In early August, I met with a firm backed by sovereign wealth that manages more than $30 billion in assets. It’s one piece of a global network of sovereign funds that together control roughly $15 trillion. Many of these funds have direct investment goals, including acquiring private companies in targeted sectors.

Market headlines are calling this ownership change a wave, a cycle, even a tsunami. AI-related investments dominate the news, but there’s considerable interest in industrials, infrastructure and “old-school” brick-and-mortar businesses too.

Entrepreneurs often ask the wrong questions. They ask how to time the market or how to land the best multiple, meaning the price a buyer will pay relative to the company’s earnings. Those questions matter. But I’ve been involved in more than 38 mergers and acquisitions across four continents. I’ve bought companies, sold companies and advised on deals from nearly every other seat at the table. And I’ve learned that price rarely decides whether a deal closes on good terms, or closes at all.

There’s never an optimal time to sell, and no business is ever perfectly ready. But there are concrete things every business must do to prepare for a sale. The usual preparations include strong financials, an independent review confirming your earnings are reliable, improved efficiency and a healthy backlog of orders. These are all important. But in a market this competitive, buyers can afford to be picky, and what separates a good offer from a premium one is increasingly something most sellers never think to document: culture.

I don’t mean culture in the team-building-retreat sense. I mean culture as an asset a buyer can actually see, test and price. And it matters just as much for a $10 million family business as it does for a billion-dollar platform.

Why cultural fit beats the multiple

Buyers aren’t only pricing your EBITDA, the earnings before interest, taxes, depreciation and amortization that most deals are valued on. They’re pricing their confidence in the story you tell them. A founder who can’t clearly explain how their people think, decide and operate day to day gives a buyer nothing solid to price. So the buyer prices in the uncertainty instead, and uncertainty always shows up as a discount.

Poor cultural alignment kills more deals than numbers ever will. I’ve seen it end negotiations backed by strong financials, and I’ve seen a well-articulated culture rescue deals that looked shaky on paper. The pattern holds whether the deal is worth $10 million or $10 billion.

Three ways to build a culture that earns a premium

If you plan to sell your business in the next few years, know this: your company already has a culture, whether you’ve shaped it on purpose or not. Your job isn’t to create one. It’s to make your culture clear enough that a buyer, who doesn’t know your company, can see it, trust it and take it over.

1. Define the values you actually live by. Many companies have values printed on a wall that don’t match how people really work. Ignore those and focus on what’s true. Which decisions, behaviors or commitments stay the same no matter who owns the company? Write down a short, honest list. It gives a buyer something solid to build on instead of something to guess at.

2. Document how your culture shows up in practice. Buyers want proof, not promises. That proof looks like leaders who behave consistently, customers who keep coming back, employees who are engaged and a team that cares about more than a paycheck. Claims in a pitch deck won’t hold up when a buyer examines your business closely. Records of what your company actually does, again and again, will. And that evidence can raise a buyer’s offer before negotiations even start.

3. Make sure your culture works without you. Ask a manager two levels below you how the company makes decisions, treats customers or handles a bad month. If their answer matches yours, your culture can survive a change in ownership. If it doesn’t, you’ve found the biggest risk in your sale before a buyer does, which is exactly when you want to find it.

Can your business run without you?

Every acquirer eventually asks some version of the same question: Can this business survive without the founder? A business that depends entirely on one person for its relationships, decisions or institutional memory isn’t really a business to a buyer. It’s a dependency, and buyers don’t pay premium multiples for dependencies.

What buyers want to see instead is an organization where strategy, structure, process and everyday behavior all point in the same direction.

A healthy, documented culture lowers a buyer’s perceived risk and earns a premium. A dysfunctional or founder-dependent one raises that risk and gets discounted, no matter how strong last year’s revenue looked. That gap is often larger than anything a price negotiation can close, and only the owner can close it, long before a banker or attorney ever gets involved.

The capital is ready. The buyers are motivated. What most owners haven’t grasped yet is that the one variable still fully in their control, months or years before any offer is on the table, isn’t the market or the multiple. It’s whether their culture is something a buyer can actually measure.

Over the next decade, up to $5 trillion in U.S. businesses is expected to change hands.

Most of that value sits with baby boomer owners aging out of companies they spent decades building, ready or not. On the buying side, private equity firms are sitting on about $1.2 trillion in uninvested buyout capital, nearly a quarter of it held for four years or more and now under real pressure to be deployed. In early August, I met with a firm backed by sovereign wealth that manages more than $30 billion in assets. It’s one piece of a global network of sovereign funds that together control roughly $15 trillion. Many of these funds have direct investment goals, including acquiring private companies in targeted sectors.

Market headlines are calling this ownership change a wave, a cycle, even a tsunami. AI-related investments dominate the news, but there’s considerable interest in industrials, infrastructure and “old-school” brick-and-mortar businesses too.