What Business Owners Learned in 2025

In this special year-end edition, we look back at the ideas, stories, and hard-won lessons that mattered most to business owners in a year that tested almost everyone.

Good Morning!

Business owners live with uncertainty every day. While that has long been true, it’s rarely been more true than it was in 2025 when so many external forces—political, economic, technological—conspired to shift the rules of the game. The goal of the Morning Report has always been to surface those changes as they’re happening: not just through our own reporting but by pointing you to the most useful journalism, analysis, and firsthand reflections we can find, whether they appear in major news outlets or in thoughtful essays on LinkedIn or Substack.

As always, we prioritize the voices of those who have actually lived the experience, owners and operators who don’t just describe problems but wrestle with them and share what they’re learning along the way. You’ll notice that one such voice, Alan Pentz, appears frequently in this year’s roundup. There simply aren’t many people who combine real operating experience with the ability to clearly explain what building a business actually demands. In 2025, Alan plunged headfirst into the promises and pitfalls of artificial intelligence, documenting his learning in unusually practical ways. (You may find yourself tempted to subscribe to his newsletter or to take his six-week AI bootcamp. I recommend both.) Other contributors whose work is highlighted here include: John Arensmeyer, Dan Kahn, Gene Marks, Josh Patrick, Marcus Sheridan, Julian Scadden, Joanna Stern, Karla Trotman, Lamar Tyler, Ramon van Meer.

The selections below are organized by theme—management, marketing, finance, and more. Given everything that unfolded this year, it’s no surprise that tariffs, labor pressures, and AI loom especially large. Still, this is a collection about entrepreneurs, and that means you’ll also find plenty of determination, creativity, resilience, and hard-earned optimism running through it all.

THE SMALL BUSINESS ECONOMY

In 2025, the gap between big businesses and small ones widened in ways that were hard to ignore: “It has been a good year for most of America’s biggest companies, with surging profits and enthusiasm for artificial intelligence propelling stocks to record highs. But for many small businesses, it has been just the opposite. At small businesses, which are unable to withstand economic headwinds as easily as their larger counterparts, years of high inflation, increasingly cautious consumers and tariffs are weighing on earnings and prompting cutbacks. Over the past six months, private firms with fewer than 50 workers have steadily shed jobs, according to payroll processor ADP, cutting 120,000 in November alone. Midsize and, especially, large firms have continued to add jobs.”

• “The growing divide between the fortunes of small and large businesses mirrors the divide that has emerged over the past year between low-income Americans and their high-income counterparts.”

• “Small businesses—those with up to 500 workers—employ nearly half the American workforce and represent more than 40 percent of gross domestic product, according to the U.S. Chamber of Commerce. But small-business profits are faltering, according to an analysis of small-business bank accounts conducted by the Bank of America Institute.” READ MORE

MANAGEMENT

Whatever it is, it’s your fault, says Alan Pentz: “I’m about to tell you something that might piss you off. But it’s the most important lesson I learned in 18 years of building a business: Everything in your business is your fault. You either hired it, did it, or allowed it to happen. Harsh? Absolutely. True? One hundred percent. I’ve coached dozens of business owners, and here’s how those conversations often start: ‘My employees just don’t take initiative.’ ‘My clients keep asking for discounts.’ ‘My vendor keeps missing deadlines.’ ‘My sales team isn’t hitting their numbers.’ Notice the pattern? ‘My’ business, but ‘their’ fault.”

• “I used to do the same thing. Blame the client who was ‘too demanding.’ Blame the employee who ‘just doesn’t get it.’ Blame the market for being ‘too competitive.’ Meanwhile, my business stayed stuck at $4 million for years.”

• “My breakthrough came when I finally looked in the mirror and asked: ‘What am I doing wrong here?’ Turns out, a lot: I hired people without clear expectations. I took on clients without setting boundaries. I tried to run everything myself instead of building systems.”

• “If everything is your fault, that means everything is in your control. And that’s power. Think about it: If your employees aren’t performing, that’s your fault. ... Which means you can fix it by changing your hiring, training, or management practices.” READ MORE

Pentz has suggestions for owners who spend too much time putting out fires: “Most owners started their business for freedom. Instead, they’ve become the most expensive employee they ever hired. They are the human duct tape holding everything together. And too many are proud of it. That pride is killing their growth.” Here are three warning signs and three fixes:

• “Your vacation requires a 47-point handoff doc. If it takes a manual to keep the lights on while you’re gone, you don’t own a business—you run a very expensive personal services company. Fix: Start with the process that breaks most when you’re away. Document it so clearly anyone can run it. Then test it.”

• “You get emergency texts about decisions your team could make. Most ‘urgent’ escalations aren’t complex. They’re just proof your team has learned you’re faster than the system. Fix: Now that you have documented processes ask the person, ‘Have you tried the checklist or talked with X?’ Keep doing that for a few weeks and the questions will stop.”

• “You know how to fix things that happen ‘once in a while’ … every month. Those ‘rare’ billing or delivery problems? They’re recurring. You’ve just normalized firefighting. Fix: Track your firefighting time for a few weeks. Where do the problems come from? Is it finance, operations, marketing? Identify the source of the chaos and then fix it with better systems and/or better people.” READ MORE

This is how Dan Kahn learned to stop chasing revenue: “I started Kahn Media nearly 17 years ago with a journalism degree, a background in PR, and zero formal training in business or finance. I bootstrapped this thing from a laptop in a spare bedroom to one of the top agencies in the industry. But I made a critical error along the way: I assumed that running an agency meant razor-thin margins were just the cost of doing business. Growth meant chasing top-line revenue. And yes, our revenue grew year over year. So did our team, our influence, and our client roster. But the bottom line never quite scaled the same way. I figured that was just how it worked. Until recently.”

• “I joined a mastermind group for agency owners. On our first call, I listened to five or six agency founders talk about real profitability. Margins I used to think were fantasy. I was floored. Honestly? I was embarrassed. And more than a little nauseous. That’s when someone recommended the book Profit First by Mike Michalowicz.”

• “The book is a game-changer. It flips traditional accounting on its head. Instead of ‘Revenue - Expenses = Profit,’ it reframes the formula as ‘Revenue - Profit = Expenses.’”

• “Michalowicz applies a concept similar to the envelope budgeting system Dave Ramsey made famous but tailored to how a business manages cash flow. You allocate profit first, then pay everything else with what remains. It’s simple in theory, hard in practice, but powerful.”

• “We’re now implementing the system at Kahn Media. It’s a heavy lift, but it’s already making a measurable difference.” READ MORE

THE 21 HATS PODCAST

Do You Have the Stomach for This? Part One: In our annual podcast review, we take a look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Paul Downs on how he decided which employees to lay off, Jennifer Kerhin on asking ChatGPT to review her performance as CEO, Kate Morgan on why she’s been reluctant to raise her prices, Liz Picarazzi on her search for a domestic manufacturer for her trash enclosures, and David C. Barnett on why your business is probably worth more to you owning it than selling it.

• You can subscribe to the 21 Hats Podcast wherever you get podcasts.

MARKETING

These days, being ranked No. 1 on Google means little: “For decades, winning a spot in the ‘10 blue links’ at the top of Google could make or break a business. Not anymore. Today, consumers are increasingly turning to chatbots and Google’s own AI Overviews for information, rather than relying on traditional search. That’s caused profound changes to the very fabric of the internet. Publishers that relied on search traffic have been gutted, and big chunks of the SEO industry have been wiped out. But the shift to information-by-AI has also unlocked the potential for equally profound (and lucrative) opportunities for companies that adapt to the internet’s new reality.”

• “When my wife needed a new laptop earlier this year, we Googled ‘best laptop for female professionals,’ but the results were mostly SEO-driven drek, the kind of useless, vapid reviews that content farms spin up to win clicks. When we asked the same question to ChatGPT, the response was totally different. The bot provided a well-researched table of potential laptop choices, as well as a detailed narrative breakdown of the pros and cons of each one. Thoroughly convinced, we clicked through on a link and bought an $818 Acer.”

• “To be clear, traffic from chatbots is still a drop in the bucket compared to traffic from traditional sources. But traffic alone doesn’t tell the whole story. Consumers increasingly use chatbots to perform research before making a purchase, often having in-depth conversations with a bot about the specifics of a product—especially if the purchase is large. The consumer may then head directly to Amazon or a brand’s own website to buy the product the LLM recommended.”

• “Numerous studies and my own research have shown that generative engine optimization depends on three things—the technical quality of a company’s website, the content it publishes on its own site, and the overall strength of its brand (as measured by signals like mentions in press coverage, success on social media, online customer reviews, and industry accolades.)” READ MORE

Here’s how businesses are trying to survive the rise of AI summaries: “Google’s AI Overviews, rolled out in May 2024, are dramatically cutting clicks to websites by delivering answers, instead of links, at the top of the search page. Knowledge-driven businesses—consultancies, publishers, and e-learning platforms—have felt it first. Local outfits—think diners, plumbers, or carpenters—have mostly yet to feel the pain, as their customers arrive through location-based searches. But time is running short for them, too, warn search engine optimization consultants who work with small businesses.”

• “Even though AI summaries don’t directly lead to clicks, [consultants] say, it’s important that companies show up in them, meaning that they need to up their sites’ educational content. [Andrew] Shotland explains the seeming contradiction this way: Research shows people increasingly trust AI summaries and that can change how they eventually select businesses. So showing up in a summary presumably has a halo effect.”

• “Those companies that do show up in these summaries may get fewer clicks than before AI, when they simply appeared high in search results. But they also may be getting higher quality leads, since those who click after reading a summary may be more serious about a subject, or closer to the point of buying, particularly from a source that has been validated by the AI summary.” READ MORE

Marcus Sheridan says talking about your pricing online is more important than ever: “For roughly 15 years, I’ve begged businesses to think like their buyers and lean into pricing transparency online. Of the hundreds of thousands who’ve read my books or seen me speak, most nodded along to the idea... but never actually did it. (Yes, that is frustrating.) But now, it’s not just a pool guy telling them they have to. AI is forcing their hand.”

• “I saw it coming the moment I used ChatGPT three years ago. Now the data couldn’t be clearer: Companies that discuss pricing online are showing up way more in AI recommendations than those that don’t. Full stop. At this point, every serious AI-optimization expert sees the writing on the wall: Pricing transparency isn’t optional anymore.”

• “It’s now one of the most important trust-signals in the world. And it’s only going to grow in importance. I’ve been saying forced transparency was coming for years. That era is now here. Only most haven’t realized it yet. But mark my words, they will, soon enough.” READ MORE

Influencer marketing is feeling less authentic: “For brands, influencer marketing offers a way to connect with an elusive demographic. Gen-Z and Gen-Alpha don’t read newspapers—and neither do many millennials—or consume much broadcast television or radio. They’re tech-savvy, know how to block ads, and often pay to remove them from their services. These consumers, skeptical of legacy media, likely feel differently about their favorite creators. When those creators tout a product, it can convey a level of credibility. These influencer-brand tie-ins may not feel like ads, but they are, and that’s the intent behind them. That is, at least, the theory. In practice, things work a little differently.”

• “Brand deals are so common that almost everyone knows when their favorite creator posts a new video, a good portion will promote a VPN provider, budget headphones, or some other product. These in-content ads are so ubiquitous (and often grating) that browser plug-ins now skip past them. SponsorBlock, for example, is the largest, with over two million Chrome users.”

• “Similarly, on apps like TikTok and Instagram, the ‘#ad’ hashtag (the telltale sign of an influencer deal) often prompts users to immediately scroll. This almost reflexive, negative response is called influencer fatigue, fueled by the overwhelming wave of promotional content on social media—and a growing annoyance with influencers themselves.”

• “That’s the thing: Influencers were once seen as a way to deliver advertising without it feeling like advertising. But over time—thanks to saturation—that’s no longer true.” READ MORE

Lamar Tyler used the Pareto Principle to improve conversions: “We were posting on Instagram six times a day. Three feed posts, three stories. Every. Single. Day. Exhausted. Burnt out. Minimal returns. Then I asked the question that changed everything: What are the 20 percent of posts giving us 80 percent of results? We analyzed everything. Engagement, clicks, conversions, actual sales (not just vanity metrics). The answer shocked us. Now I post three times a week. More engagement. More revenue. Less exhaustion. My team got their sanity back.”

• “The 80/20 principle works everywhere in business: 20 percent of clients generate 80 percent of revenue, 20 percent of activities create 80 percent of results, 20 percent of products drive 80 percent of profits, 20 percent of decisions determine 80 percent of outcomes.”

• “But entrepreneurs are addicted to doing MORE. More posts. More offers. More channels. More features. More services. More, more, more. We think volume equals value. Activity equals achievement. Busy equals productive. Wrong.”

• “At our last event, I asked our clients: ‘What are the top three to five things that, if you focused on them consistently for six months, would move you fastest toward $1 million? Not 30 things. Not 10 things. Not even seven things. Three to five things maximum. The exercise was painful. They had to kill their babies. Delete their pet projects. Say no to good opportunities to say yes to great ones.” READ MORE

Alan Pentz says many business owners are blind to opportunities right in front of them: “Last month I was talking a client through a problem most companies have: not enough leads. ‘Should we start Google Ads?’ she asked. This is always the refuge of the desperate. After a few questions it turned out she already had a 20,000-person email list she was emailing once a year. Once. A. Year. With no clear call-to-action. Just an occasional note or update.’”

• “After 200+ consulting sessions, I’ve noticed a pattern. Business owners have three types of blindness: Asset blindness: You don’t see what you already have. Email lists gathering dust. Customer databases without segmentation. Past clients who haven’t been contacted in 18 months.”

• “Proximity blindness: You’re too close to see adjacent opportunities. The retail client thought of her retail and service business as separate. The email list client thought ‘we don’t want to bother people.’”

• “Assumption blindness: You’ve decided something won’t work without testing it. ‘Our customers won’t pay for that.’ ‘Email doesn’t work in our industry.’ ‘We tried that once five years ago.’” READ MORE

THE TRADE WARS

To the surprise of many, Zachary Karabell pointed out, the tariffs did not spark a recession in 2025: “On April 2, President Donald Trump announced sweeping global tariffs, calling it ‘Liberation Day.’ Markets plunged in response. Most observers predicted sharply higher inflation, domestic and global economic contraction, and widespread spikes in unemployment. As the year ends, little of that has happened. Why? And what does that mean for next year? 2025 ends on a positive note for the economy, in terms of the numbers and relative to expectations in April. That should be celebrated. ‘Things aren’t as bad as feared,’ isn’t a resounding vote of confidence, but it’s better than the alternatives.”

• “The reasons tariffs didn’t tank the economy are fairly simple: There is a wide gap between tariffs that were announced in April and the following months and the tariffs that have actually been applied and collected. The announced tariffs would have been about 25 percent across the board, the highest rate in roughly a century.”

• “The actual tariff rate? According to Yale’s Budget Lab, it was about 17 percent as of November. Even that estimate is likely higher than the actual rate. Judging from how much revenue has been collected, the realized rate is probably around 9 percent in aggregate. For instance, more than 85 percent of all trade between the U.S. and Canada remains tariff free because of prior agreements, so even though the U.S. announced a rate of 35 percent, the actual amount is around 8 percent.” READ MORE

Even “Made in the U.S.A.” companies have a hard time making everything in the U.S.A.: “Manufacturers that already make products in the U.S. said it is tough to create an entirely domestic supply chain. Parts or materials vital to their products are no longer made here, they said, or are available only in quantities that are too low or prices that are too high. Ricky Cousido is co-owner of Brooklyn-based Rapid Plastics, a six-person company that makes high-end coat hangers for department stores and other retailers. He said the domestic suppliers that furnished the metal hooks for his company’s hangers closed or went overseas more than two decades ago.”

• “He now gets the hooks and other metal components from China, and the U.S. tariffs on imports from the country are rapidly boosting his expenses. The bar of a skirt hanger, which cost 40 cents before the duties were imposed, now costs 80 cents, he said. Cousido said government policy should make exceptions for manufacturers unable to find U.S.-made components: ‘I can’t beg some company, Open up, make this item for us.’”

• “Haas Automation, a California-based builder of factory machinery, makes a similar argument. It imports cast iron from China to make the frames for its products. Peter Zierhut, vice president of outside operations for Haas, said the U.S. has no foundries capable of generating the [millions of] pounds the company consumes each year, and he sees little chance any will return. Building a new foundry would require hundreds of millions of dollars in investment to turn out a commodity that is worth just a few dollars per pound, he said. Finding workers would be tough as well, he said.”

• “The tariffs the company is paying on iron and other parts from China could raise the price of its machines by about 20 percent, he said. Meanwhile, competitors based in South Korea, Taiwan, and Japan are sending their products to the U.S. at just a 10-percent to 14-percent tariff. Haas said it has already cut production and eliminated overtime at its plant in Oxnard, Calif. The company is building a $500 million factory in Nevada to serve what it had expected to be increased demand for its machines, but Zierhut said that without tariff relief the plant’s opening might be delayed.” READ MORE

Ramon van Meer ran a test that showed Americans don’t necessarily want to pay more for a product manufactured in the U.S.: “We make filtered shower heads. Clean, sleek design. But more importantly, with the best shower filters on the market. Our bestselling model—manufactured in Asia (China and Vietnam)—sells for $129. But this year, as tariffs jumped from 25 percent to 170 percent, we wondered: Could we reshore manufacturing to the U.S. while maintaining margins to keep our lights on? An important part to mention is that our filter material (KDF-55) is sourced from the U.S. So technically we partly source from Asia. We found a U.S.-based supplier. The new unit cost us nearly 3x more to produce. To maintain our margins, we’d have to sell it for $239. So we ran an experiment.”

• “We created a secret landing page. The product and design were identical. The only difference? One was labeled ‘Made in Asia’ and priced at $129. The other, ‘Made in the USA,’ at $239. The visitors were given the choice to either buy the Made in USA or the Made in Asia version.”

• “The results were sobering. Add-to-carts for the U.S. version were only 24! Conversion? 0.0 percent (zero). Not a single customer purchased the Made in USA version. [The Made in Asia version produced 3,560 add-to-carts and 584 sales.] We tested everything: color, copy, layout. We ran it over multiple days and traffic sources. Same outcome every time.”

• “We wanted to believe customers would back American labor with their dollars. But when faced with a real decision—not a survey or a comment section—they didn’t. It’s not their fault. Most people are stretched. They’re feeling inflation everywhere: gas, groceries, mortgages. ‘Supporting U.S. manufacturing’ becomes a luxury most can’t afford—even if they want to. This isn’t just our problem—it’s the economy’s.” READ MORE

To avoid the tariffs, this family business moved overseas: “In February, when President Trump started levying tariffs against major U.S. trade partners, Vicky Pasche started going down the rabbit hole looking for a fix to save her family clothing business, Dapper Boi. ‘It was very scary,’ recalls Pasche. ‘That could take out a brand like ours completely.’ Her manufacturer mentioned a potential solution: India, where Dapper Boi makes its all-gender line of jeans, chinos, button-up shirts, jackets, T-shirts, and sweatshirts, has a free trade agreement with the United Kingdom.”

• “So, Pasche and her wife and co-founder, Charisse, decided the best way to survive and grow their company was decamping to Europe. About seven months later, they left San Diego, where they’d spent the past decade building the business, and moved their family to Spain. They are in the process of re-incorporating Dapper Boi in the U.K., where they already have an established customer base.”

• “It was a prescient decision. Just weeks before the Pasche family moved to Valencia, the Trump administration’s 50-percent tariffs on products imported from India took effect. Once Dapper Boi is officially registered in the U.K. and has a U.K. fulfillment center, the savings will be huge, says Vicky. The company, which generates over $1 million in annual revenue, expects U.K. production to start next year. “ READ MORE

As a contract manufacturer, Karla Trotman confronted several existential questions in 2025: “Here’s the reality: One major customer can shift your entire year’s trajectory. The textbook answer? Cut costs immediately. Lay people off. Protect the bottom line. But here’s what the textbooks don’t account for: my skilled technicians take 6-18 months to train. They can’t be replaced with a job posting. And more fundamentally—they’re not line items on a spreadsheet. They’re people with families, mortgages, lives built around the stability we promised them. So when revenues dropped this year, we didn’t do layoffs. We reduced hours. We absorbed the pain at the business level to protect the people who ARE the business. Was it the ‘smart’ financial move? My cash flow would say otherwise. But my ability to scale back up when orders return—and my conscience—says yes.”

• “Relationships that were once the foundation of business are being replaced by procurement departments focused solely on cost. Customers who used to value reliability now lead with, ‘Can you sharpen your pencil on this?’”

• “Tariffs have created chaos nobody talks about. Customers are pausing orders because raw material costs from overseas suppliers keep shifting. Many of these materials simply cannot be made in the U.S. overnight, no matter how high the tariffs rise.”

• “Everyone says specialize, find your niche. But when existing customers are cutting spending, you need to diversify to survive. Which is it?” READ MORE

PRICING

Perhaps inexplicably, some small businesses say they would rather go out of business than raise their prices: “When Jeremiah Chamberlain and his wife, Harriet, started their 3D-printing business in March last year, tariffs weren’t high on their list of challenges to prepare for. ‘We didn’t expect to have this type of panic arise,’ said Chamberlain, the owner-operator of Corvidae Creations in Hammond, Louisiana. But in the months since President Donald Trump took office and kicked off a freewheeling global trade war, Chamberlain has spent a few thousand dollars more on 3D printers from China. Chinese-made goods currently face a U.S. tariff rate of at least 30 percent, down temporarily from 145 percent just weeks ago.”

• “‘The whole point of it, when we went into the toy production, was to make a durable, affordable toy for families and children,’ he said, referring to his lineup of dragons, possums, and dinosaurs. ‘Nothing’s going to make me raise prices unless it’s a matter of me having to shut the business down totally.’ The company is one of many across the country promising not to raise prices on customers despite Trump’s import taxes.”

• “Some entrepreneurs see their duty to customers much the same way. ‘I won’t be raising prices,’ said Carla Minervini, who runs All Fired Up, a pottery studio in Pawleys Island, South Carolina. ‘I cannot do that to my community.’ Like Chamberlain, Minervini is doing her best to adapt. She has reassessed her product assortment and is working to sub in smaller versions of certain pieces or find alternatives in different shapes.”

• “Her main supplier — which is based in the U.S. but imports items from China — announced a 7.25-percent across-the-board price hike starting in June, she said. Another supplier flagged coming increases, too, but hasn’t indicated when or by how much. Minervini is unwavering, though. ‘I would sell everything off and close my business and make a new life for myself before I would increase my prices,’ she said.” READ MORE

On the other hand, this company has started changing prices every three months: “Rocky Mountain Chocolate’s answer includes quarterly pricing adjustments for truffles, chocolate-covered pretzels, and more to account for the turbulent cocoa market. Executives call it dynamic pricing, though there are no plans to change prices based on demand around popular chocolate holidays such as Valentine’s Day, said Chief Financial Officer Carrie Cass. Instead, the chocolate seller will raise—and lower—prices on a set schedule based on its own costs. ‘We’re really trying to stick to a certain margin,’ Cass said.”

• “The past several quarters have been bruising for the company, prompting cost cuts, leadership shifts, and operational changes including the new pricing strategy. Revenue has largely remained flat the past few years, aside from spikes around occasions like Valentine’s Day and Christmas.”

• “With two price adjustments so far, total product and retail gross profit increased 200 percent, to $300,000, for the quarter ended May 31 compared with a year earlier. Total gross margin increased to 6.9 percent for the period, compared with negative 5.8 percent a year earlier. Rocky Mountain Chocolate anticipates adding several million dollars in gross profit this fiscal year because of the new approach to price adjustments, executives said in June.”

• “The plan was put into motion this year after the company revamped its data collection on sales, input costs, and other items. Such figures used to come with a delay, and often weren’t granular enough to make decisions about specific products. Now, the company monitors sell-through, inventory trends, and product performance in real time and at a store level, and executives can see the margins tied to each product, Cass said.”

• “‘So instead of just saying we’re going to increase prices across the board 5 percent or 10 percent or whatever, we strategically look at each [stock keeping unit] and set a target margin so that even if our costs go up, our adjusted pricing will still provide us with that target margin,’ the CFO said.” READ MORE

Julian Scadden says home-services businesses are too quick to compete on price: “Every contractor I talk to thinks the solution to price objections is better pricing. Lower prices to compete with the guy down the street. Or raise prices and hope customers don’t notice. Both strategies miss the point entirely. Your customers aren’t choosing based on price. They’re choosing based on perceived value. And most service businesses suck at communicating value.”

• “Take the lawn care industry, for example. Talk to any homeowner and they’ll tell you the same thing: ‘They’re all bad, but at least they’re cheap.’ Nobody’s positioning themselves as the premium choice. Nobody’s explaining WHY they should cost more. So customers default to the cheapest option, expecting and accepting mediocre results. This creates a race to the bottom where nobody wins except the customers—and even they’re getting terrible service.”

• “But here’s what happened when one of our Nexstar members tried something different. Instead of competing on price, he started positioning his plumbing company as the ‘stress-free solution.’ Same basic services. Same technical expertise. But now he sends customers a photo of their technician before arrival. Gives them a 30-minute arrival window instead of ‘sometime between 9 and 5.’ Provides upfront pricing before any work begins. His average ticket went up 40 percent.” READ MORE

SALES

Alan Pentz warns against hiring a salesperson too early: “Fair warning: If you’re struggling to grow past $1-2 million and think hiring a salesperson is the answer to working fewer hours, you’re not going to like what I’m about to say. I’ve watched dozens of business owners make this exact move while trying to escape the daily grind. Hell, I did it myself. And it almost always ends the same way—with a fired salesperson, wasted money, and a business that’s still completely dependent on you.”

• “Here’s how it usually goes: Your business hits $1-2 million with you as the primary (or only) salesperson. You’re drowning in work and think, ‘I need to clone myself.’ You hire a sales person with a hefty base salary and commission structure. Six months later, they’ve closed little to nothing. You fire them and start over. I went through THREE salespeople this way. Each one was a great person who I genuinely liked. And each one failed spectacularly.”

• “Stage 1: Optimize your time ($0-1M): Don’t try to hire a salesperson yet. Instead focus on effective delegation: Get an assistant to handle your calendar and email. Delegate all non-sales tasks. Create simple follow-up systems. Say no to non-ideal clients to focus on better ones.”

• “Stage 2: Document and systemize ($1-5M): Before you can hire someone, you need to know what actually works: Hire a sales admin to do all the logistics to free up your time. Track every lead and what happened to it. Get a CRM system. Identify your actual sales process (not what you think it is). Create sales collateral that explains what you do. Start building a reputation beyond just you.”

• “Stage 3: Hire for support, not replacement ($5-10M): Don’t try to replace yourself yet: Bring on junior people (beyond the admin) who can handle parts of the process. This helps scale founder sales. Document your sales conversations. What works? What doesn’t work? Start to document and refine the sales process that works. Keep doing the critical customer/client meetings yourself. You’re still the closer, but you don’t have to be in every step of the way.” READ MORE

Pentz also warns against trying to hire a sales superstar: “The owner I talked with last week had just gone through his third failed sales hire. The pattern? ‘We hired for product knowledge—failed to look at character.’ But here’s the deeper mistake: They were trying to hire ONE person who could do everything the founder does. Product expertise + all the relationships + sales nuance + operations + strategy. That’s not a job description. That’s a unicorn. And unicorns don’t exist.”

• “Here’s what happens when you track your sales process with AI and ask: ‘What am I actually doing?’ AI breaks it down: Marketing: nine hours/week (lead gen and qualification). Admin: five hours/week (writing and sending follow-ups, updating the CRM and dashboards). Selling: seven hours/week (actual conversations with buyers). Meetings and Reporting: five hours/week (in internal meetings and preparing for those meetings). Customer Service: 10 hours/week (talking recent sales through onboarding issues).”

• “You’re not hiring for one role. You’re trying to get one person to do a bunch of different stuff. The AI insight: Don’t hire one ‘unicorn’ at $150,000 who’ll fail in 18 months. Engineer it into three achievable roles: Sales Rep ($75,000): hire for relationship skills and ability to close. Operations Coordinator ($55,000): hire for ability to track actions, update the CRM, and do follow-ups. Customer Service Rep ($60,000): hire for deep product knowledge and ability to answer customer questions.”

• “The real problem: You’re not bad at hiring. You’re trying to hire another version of yourself.” READ MORE

Gene Marks says maintaining a pipeline report is critical: “Rarely do I meet a business owner who isn’t looking to increase sales. There’s never quite enough work, right? The backlog only stretches so far — and beyond that lies the abyss. The truth is, there’s no magic bullet for growing revenue. But there is one report you should be reviewing every single week that will dramatically help: the pipeline report.”

• “Successful owners and managers live and die by this report because it tells them their future. It identifies potential revenue shortfalls before they happen, highlights top performers, and gives them the visibility to plan their marketing, spending, hiring, and investment decisions with confidence.”

• “Start with the basics. List every active opportunity with the company name, contact, description, estimated value, date created, expected close date, and the salesperson or manager responsible for it. Don’t limit this to new prospects — include existing customers if they’re likely to buy more.”

• “When an opportunity is lost, remove it from the active report but keep it in your database. Always record a reason — price, competitor, timing, or any other factor. Review these reasons quarterly. Patterns will emerge. You may find that a specific competitor is winning too often, or that pricing or communication needs improvement.” READ MORE

FINANCE

A relatively small, branchless bank in North Carolina, Live Oak Bancshares, does a lot of small business lending: “Since 2017, it has issued $15.4 billion in government-backed 7(a) loans, more than any other bank in the country including the aforementioned Wall Street heavyweights. The 7(a) program is the Small Business Administration’s flagship offering, designed to help small businesses that might not qualify for conventional credit. Live Oak’s average loan is just $1 million, chump change for bigger, brand name competitors, but the lender does around $2 billion a year in SBA loans, plus another $3 billion in conventional small business loans.”

• “Live Oak has no branches. All deposits come in online. And while most people think of small business lending as a handshake deal at the local bank down the street, Live Oak has flipped that on its head. It leans on tech, instead of geography with a fintech venture arm called Live Oak Ventures and a track record that includes spinning out the $3.4 billion market capitalization cloud-based banking software firm nCino. That edge in technology helps it approve loans faster. Which means it can make more of them.”

• “Loan officers don’t earn commissions, a move designed to avoid conflicts between sales and credit. The bank also doesn’t try to be everything to everyone. It sticks to industries where it has subject matter expertise. The bank started by lending to veterinarians because its CEO Chip Mahan’s stepfather is a well-known equine vet. Today, Live Oak focuses on 35 industry verticals, including home health care, funeral homes, and auto repair.”

• “Mahan built the bank around a simple premise: lend to the people big banks overlook. ‘I don’t think JPMorgan cares about the female veterinarian doing a million and a half in revenue in every town in America,’ he says. ‘But we do.’” READ MORE

Predatory lenders have found a new target market: “Some small businesses that have to pay the bill for President Trump’s new tariffs are taking on high-interest-rate merchant cash loans and other forms of debt to cover that added cost. And several business owners who have taken on that costly debt told CNBC they fear financial disaster because of it. Companies that spoke with CNBC reported being offered predatory lending interest rates north of 30 percent to cover their tariff-related costs.”

• “Josh Esnard, CEO of The Cut Buddy, a shaving-products company [that you may have seen on Shark Tank], said that he receives multiple calls each day from high-interest-rate lenders. ‘They are very aggressive and deceptive in their practices in reaching out both by phone and email,’ Esnar told CNBC. Esnard said even if the Supreme Court rules the tariffs are illegal and his company is issued a refund, the money will not make Cut Buddy whole.”

• “Esnard originally used three different lenders to pay his tariffs, with interest rates on his merchant cash loans falling between 24 percent and 30 percent. CNBC reviewed those agreements. To be considered for the loans, Esnard paid underwriting origination fees totaling $30,000, which was in addition to the loans themselves. Esnard borrowed a total of $950,000 in the three loans to pay for tariffs totaling $800,000.”

• “Esnard recently received a financial lifeline to help stop his high-interest payments through a loan from The Business Consortium Fund, which focuses on minority-owned and small businesses. The fund reviewed his high-rate loans and approved a new loan to fold in those payments for Esnard. ‘Instead of paying a weekly payment of $35,000, I will now be paying $35,000 a month,’ Esnard said.” READ MORE

HUMAN RESOURCES

Employers are getting ghosted by Gen Z job candidates: “A recent report from Resume.org found that 54 percent of hiring managers have been ghosted by a Gen Z candidate after extending a job offer. The report, which surveyed 1,115 hiring managers, also found that 66 percent of hiring managers said Gen Z ghosting has made the hiring process more difficult. It’s caused 1 in 10 hiring managers to no longer consider Gen Z candidates at all — yet another reason employers have provided for why they’re frustrated with Gen Z applicants.”

• “For hiring managers who have been ghosted, that action is playing out in different ways. According to the Resume.org report, 27 percent said candidates have accepted an offer but never completed the necessary paperwork; 26 percent said they’ve completed the paperwork but do not show up on day one; and 29 percent said candidates have shown up for a few days or a week before disappearing without notice.”

• “More than half (52 percent) of the hiring managers surveyed by Resume.org said they emphasize commitment expectations earlier in the process. Additionally, 43 percent of respondents said they have implemented friendly check-ins between the offer and start date. A smaller group (24 percent) has begun incorporating social or team-based onboarding activities to build engagement and reduce no-shows.”

• “Hiring managers also are trying to do a better job of identifying clear signs of engagement throughout the process. According to the report, the top indicators include showing up on time to interviews (68 percent), consistent communication throughout the process (65 percent), demonstrating interest by asking questions (64 percent), and prompt replies to emails or messages (62 percent). Additionally, 36 percent of respondents noted that they view thank-you or follow-up notes as signs of dependability.” READ MORE

Glen Valley Foods used E-Verify on every hire. ICE still took half the company’s work force: “For more than a decade, Glenn Valley’s production reports had told a story of steady ascendance — new hires, new manufacturing lines, new sales records for one of the fastest-growing meatpacking companies in the Midwest. But, in a matter of weeks, production had plummeted by almost 70 percent. Most of the work force was gone. Half of the maintenance crew was in the process of being deported, the director of human resources had stopped coming to work, and more than 50 employees were being held at a detention facility in rural Nebraska. ... ‘It’s a wipeout,’ said Gary Rohwer, the owner. ‘We’re building back up from ground zero.’”

• “Rohwer, 84, had always used a federal online system called E-Verify to check whether his employees were eligible to work, and Glenn Valley Foods itself had not been accused of any violations. Rohwer was a registered Republican in a conservative state, but he’d voted for a Democrat for the first time in the 2024 election, in part because of Trump’s treatment of immigrants. Rohwer couldn’t square the government’s accusations of ‘criminal dishonesty’ with the employees he’d known for decades as ‘salt-of-the-earth, incredible people who helped build this company,’ he said.”

• “He looked out into the lobby and saw three women filling out applications. Glenn Valley paid well, with an average hourly wage of almost $20 and regular bonuses, but the work was repetitive and demanding. Employees who came mostly from Mexico and Central America stood on a manufacturing line for as much as 10 hours a day, six days a week, and processed hundreds of pounds of meat through dangerous machinery in a cold factory.”

• “Rohwer had met with officials after the raid to ask for a better system, and they told him to keep using E-Verify. One agent gave the company a hotline number to call for hiring questions. Hartmann tried it once and waited on hold for 57 minutes before giving up. ‘They said the only thing we can do is verify, verify, verify,’ Rohwer said. ‘But we’re already doing that,’ [President Chad] Hartmann said. ‘How do we avoid ending up in the same situation?’” READ MORE

John Arensmeyer explained why Association Health Plans aren’t as good a deal as many think: “AHPs might lower healthcare costs on paper for the businesses that choose to enroll in them; however, these plans are not required to offer many of the essential health benefits and consumer safeguards that plans regulated under the Affordable Care Act are required to provide. After all, most of us wouldn’t rush to sign up for a health insurance plan that doesn’t include maternity care, mental health services, and prescription drug coverage. Those are examples of some of the benefits not found in many AHPs.”

• “AHPs may also charge some enrollees higher premium rates based on gender and occupation, while at the same time having no rules on how much more older people are charged than younger people. AHPs primarily benefit businesses with younger, healthier employees while leaving older employees and those with pre-existing medical conditions with inadequate coverage. While these plans may seem more advantageous economically, small businesses and their employees may end up paying much more out of pocket to cover their basic healthcare needs when compared to coverage under the ACA.”

• “AHPs don’t only harm enrollees. Their broad expansion would destabilize the healthcare insurance market for small businesses that chose to purchase a regular healthcare plan. When healthier customers exit the small group market in large numbers, it creates a risk imbalance that can lead to significant premium spikes for small firms that remain in the small group market.” READ MORE

Gene Marks pointed out that paying severance is a lot cheaper than paying a lawyer: “Employee terminations happen and if not done the right way, it could cause headaches for the employee and legal problems for the employer. ‘Once you make a misstep, you can’t undo it,’ said Robin Bond, an attorney with the consulting firm Transition Strategies in [Pennsylvania]. Terminations should never be a surprise. Many experts say it’s important to communicate problems to an employee often and warn them as early as possible.”

• “Employees need to be told when there’s a problem and then given an opportunity to correct it, said Bond. When somebody understands the reason for their termination (‘even if they don’t agree with it’), they’re less likely to take legal action, said Eva Zelson, a labor attorney with Zeff Law Firm in Philadelphia.”

• “As an employer, it’s critical to document all of your actions because documentation is your best protection. It should be done as events occur, not after the fact, and in a way that maintains professionalism. This could be as simple as writing a note to the employee saying, ‘We talked about this behavior and how we want to address it moving forward,’ Bond said.”

• “Some of my clients resist offering severance, particularly if the employee is being terminated for behavior or very poor performance. Regardless, I always advise them to offer something. It’s not just a means to placate or to avoid potential legal issues. In most cases it’s just the right thing to do. ‘If you just fire somebody [and offer] nothing, then what’s the deterrent to suing you? There is no deterrent,’ said Bond. ‘It’s so expensive if you get into litigation — definitely more than a reasonable severance package would be.’” READ MORE

ARTIFICIAL INTELLIGENCE

Alan Pentz suggested some quick ways to get started on AI: “Too many people see AI as merely a time-saving technology. That’s selling it short. Here are five ways AI can give you a real competitive advantage in your business. Whether you’re using ChatGPT with its new project-based memory feature or the more sophisticated Claude Code working directly with files on your computer (backed up in GitHub), these strategies will transform how you operate.”

• “Client intelligence that spots patterns: Store every client interaction—emails, meeting notes, project updates—in ChatGPT Projects or local files. Build prompts or agents that analyze patterns across all engagements to uncover insights you’d never spot manually. I’ve used this approach to reveal persistent business patterns for clients, including identifying underperforming employees who needed coaching or replacement.” Quick start: Upload your last 20 client emails to ChatGPT or connect it to Gmail using the Connectors feature (Claude and Gemini offer this too). Ask: ‘What patterns distinguish highly satisfied clients from those at risk of churning?’ or ‘What recurring themes across these conversations reveal opportunities or weaknesses in my business?’”

• “Continuous team performance intelligence: Create running records of feedback sessions and check-ins for each direct report. Use AI to track accountability and spot improvement opportunities before they become crises. Quick start: Record your next one-on-one and upload relevant emails for a single team member. Ask ChatGPT to identify wins, challenges, and emerging trends. Have it draft follow-up emails post-meeting. Review patterns weekly or monthly instead of waiting for annual reviews.”

• “Battle-test ideas before launch: Create detailed customer personas in ChatGPT or have Claude Code develop persona agents. Test every pitch, product idea, and marketing message through their lens before going live. Let AI poke holes in your strategy before real customers do. Quick start: Describe your ideal customer to ChatGPT in detail. Have it critique your homepage copy from that customer’s perspective—you’ll be surprised what you’ve been missing.” READ MORE

Pentz says you probably don’t realize how often you fail to act on valuable information in your conversations: “Most business owners treat conversations like air—essential while they’re happening, then gone forever. That’s the wrong approach. That client call where they mentioned budget concerns? That team meeting where Sarah suggested a process fix? That one-on-one where Mike finally admitted what’s really blocking progress? Every one of those conversations contains data that predicts your business future. Your competitors who systematically capture this information can see patterns you can’t. You think you remember the important stuff. You don’t.”

• “Research shows people forget 50 percent of new information within an hour and 90 percent within a week. That critical insight from Tuesday’s client meeting? By Friday, you remember the conclusion but not the reasoning that led there.”

• “Meanwhile, companies that record and document interactions can analyze hundreds of data points. They know which clients show early warning signs before they churn. They can predict which team members will hit roadblocks before those roadblocks even appear.”

• “Modern AI tools can surface patterns no human could see manually. Upload client call notes into ChatGPT and ask it to identify accounts showing churn risk. Feed it your team meeting summaries and let it highlight recurring operational bottlenecks. Businesses that start building an information advantage now will quietly dominate the ones still flying blind.” READ MORE

Pentz says owners should try to disrupt their own business before AI does it for them: “I keep having the same conversation. Four owners last month asked me: ‘Should I sell before AI disrupts my business?’ Meanwhile, I invested in a metal-fabrication company. The owner was spending 20 to 30 hours per week processing purchase orders. Not sustainable when you’re trying to grow. We built an AI system in two weeks. PO processing now takes 5 minutes. He got 25 hours of his week back. We’re closing on our second acquisition next month. Same playbook: build the AI capability once, plug each new company into the same operating system. That’s exactly what the PE firms are doing. At scale.”

• “Here’s the data that matters: 95 percent of AI pilots fail. But the 5 percent who break through? Ninety-one percent see a revenue boost. Eighty-six percent improve margins.”

• “This isn’t a technology problem. It’s a commitment problem. Pilots are experiments nobody owns. The winners pick one process, assign ownership, and measure results until it works. Then rinse and repeat.”

• “The gap between ‘wanting to use AI’ and ‘actually transforming your business’ is where most owners get stuck. That’s exactly the gap PE firms are exploiting. I’m not going to pretend I’m not doing the same thing PE firms are. The difference: I’m showing you exactly how it works so you can do it yourself.” READ MORE

And yet, for all of the promise of AI, don’t think you can just set your business on autopilot: “In mid-November, [Joanna Stern, a columnist at the Wall Street Journal] agreed to an experiment. Anthropic had tested a vending machine powered by its Claude AI model in its own offices and asked whether we’d like to be the first outsiders to try a newer, supposedly smarter version. Claudius, the customized version of the model, would run the machine: ordering inventory, setting prices, and responding to customers—aka my fellow newsroom journalists—via workplace chat app Slack. ‘Sure!’ I said. It sounded fun. If nothing else, snacks!”

• “Logan Graham, head of Anthropic’s Frontier Red Team, told me the company chose a vending machine because it’s the simplest real-world version of a business. ‘What’s more straightforward than a box where things go in, things go out, and you pay for them?’ he said. Anthropic’s partner, a startup called Andon Labs that is workshopping agentic businesses, built the hardware and software integration, and handled the entire setup.”

• “This was supposed to be the year of the AI agent, when autonomous software would go out into the world and do things for us. But two agents—Claudius and its overseeing ‘CEO’ bot, Seymour Cash—became a case study in how inadequate and easily distracted this software can be.”

• “Within days, Claudius had given away nearly all its inventory for free—including a PlayStation 5 it had been talked into buying for ‘marketing purposes.’ It ordered a live fish. It offered to buy stun guns, pepper spray, cigarettes, and underwear. Profits collapsed. Newsroom morale soared.” READ MORE

OPPORTUNITIES

More young people are buying blue-collar businesses: “[Adam] Froendt is one of a growing number of young people looking to test their entrepreneurial mettle through the world of so-called search funds. Sometimes described as mini-private equity or entrepreneurship through acquisition, a search fund is a small investment fund run by one or two people established to buy an existing small business. Once the business is purchased, the ‘searchers’ run it with an eye toward creating value by streamlining operations and growing in size.”

• “The boom in search funds is partly a response to a more complicated job market. White-collar jobs, once the obvious pathway to success, feel less stable. The dream of entrepreneurship is still alive and well, but tech startups can feel out of reach given the enormous shadow tech giants like Google and Amazon now cast over the economy. Search funds and their various cousins offer a more realistic path to entrepreneurship.”

• “Froendt is taking a higher-risk and higher-reward path by self-funding his search, which takes, on average, two years. This model offers more flexibility over the businesses targeted, as well as more control and, eventually, more equity. As the founder of TrueGrit Capital, Froendt will be living off his ‘own personal balance sheet’ (his savings) for up to two years.”

• “The next step is to buy a successful small business, often from an owner-operator looking to retire. Froendt is looking for a company with between $3 million and $12 million in yearly revenue located between Maryland and South Carolina and in the healthcare services (think home health or care management), financial services (think insurance or accounting), or knowledge (think training or certification) industries.” READ MORE

And these days, the owner’s kids seem more inclined to take over the family business: “A young generation is taking a bigger interest in joining the family business, spurred by a cooling labor market that is making it more difficult to land entry-level jobs, economists and business analysts say. At the same time, their parents and grandparents—Baby Boomers and Gen Xers who own the vast majority of America’s businesses—are feeling more urgency about making succession plans as they look toward retirement. The share of small businesses that employ a young adult child of an owner has doubled since 2018 and is up 13 percent year-over-year as of January to roughly 1,200, according to an analysis by payroll provider Gusto.”

• “Mark Valentino, the head of business banking at Citizens, sees this moment as a reversal from recent decades in which the children of business owners tended to stigmatize returning to the family firm in favor of striking out on their own.”

• “For many, that interest is driven by economic realities. Covid upended the career paths of many young people, then a boom in artificial intelligence and the more recent trade-war unease began reshaping the entry-level job market.”

• “Family business strategist Gary Plaster of the Fairhope Group said he has been seeing more of his clients hire their children in the hopes of passing their companies onto them. While it sometimes works out, he said, there are pitfalls. Young family members who haven’t worked in the business before may be entering it as young adults without training or experience. ‘What’s happening seems like it’s better for the kids than it is for the business,’ Plaster said.” READ MORE

More people are choosing to start businesses in their seventies: “These emerging septuagenarian entrepreneurs share many motives with younger counterparts. They want to be their own boss, set their own schedules, and pursue meaningful projects. While older entrepreneurs might have lost some stamina, age has benefits. People in their eighth decade can leverage years’ worth of contacts and experience. With their children grown, they may feel free to address what has long bothered them, like clutter and costly in-home care. Or, in the case of the founders of Judson Squared, dull trial lawyers. ‘They’re boring as hell,” says Judson Vaughn, 71, an actor and filmmaker. He partnered with attorney Judson Graves, 77, known for his persuasive court performance, to create online courses to teach lawyers how to be entertaining as well as effective.”

• “Self-employment rates rise dramatically as people age. Nearly 30 percent of employed people in their 70s work for themselves, almost double the share of self-employed people in their 60s, says Cal Halvorsen, an associate professor of social work at the Brown School at Washington University in St. Louis. That translates into about 1.3 million septuagenarian entrepreneurs, he says.”

• “Charlotte Bishop never aspired to be an entrepreneur. ‘I didn’t think it would offer a steady income,’ she says. Widowed at a young age, with two children, Bishop pursued her master’s, and taught office administration skills at City University of New York. Once retired, friends and neighbors asked for help organizing files and clearing clutter.”

• “Seeing demand for her skills and an opportunity to earn money for her sons when they went to college and then started families, Bishop founded Life Files Professionals to manage documents and organize offices, apartments, and computer files. The business is evolving as she is. Bishop recently began offering concierge services for older adults and family caregivers. She researches long-term care options, organizes health records, and arranges grocery orders and deliveries. All of these services can be done remotely, which is more important since she turned 80 this year.” READ MORE

OBITUARY

Stephanie Shirley started a software company in 1962 that employed women trying to return to the workforce. Eventually, 70 of them became millionaires: “When she started her software business, Freelance Programmers, in 1962, British women could not work on the stock exchange floor or even drive a bus. Her initial financing was six pounds (roughly $16.85 then and about $220 today), but she needed her husband’s signature to open the company’s bank account and deposit her own money. In a 2015 TED Talk, Ms. Shirley said, ‘You can always tell ambitious women by the shape of our heads — they’re flat on top from being patted patronizingly.’”

• “At the time, many educated women left the computer industry after marrying or having a child. Ms. Shirley provided them an opportunity to re-enter the workforce while remaining at home, writing code part-time with flexible hours. When the company’s name was changed to F International — and then F1, and eventually Xansa — the F stood not only for freelance but also for flexible and free. In job interviews, she asked applicants one simple question: ‘Do you have access to a telephone?’”

• “But there were early frustrations. When she sent business letters signed Stephanie Shirley, they often went unanswered. At the suggestion of her husband, Derek Shirley, a physicist she married in 1959, she began introducing herself in correspondence as Steve. Increasingly, prospective clients granted her interviews, although she could see when she walked through the door, she later told the British newspaper The Telegraph, ‘that they were almost annoyed at themselves at having been conned.’”

• “Still, work orders picked up, and she began hiring more programmers. Of her first 300 employees, 297 were women. The company designed software for the black box flight recorder on the Concorde supersonic jet, and for scheduling buses and freight trains. It also developed software protocols that were eventually adopted by NATO.”

• “In 1975, an anti-discrimination law required Ms. Shirley to diversify her work force, and she started hiring more men. In 1991, she began restructuring her company to share ownership with her employees. By her count, 70 eventually became millionaires.” READ MORE

THE ENTREPRENEURIAL LIFE

Josh Patrick identified the biggest lie business owners tell themselves: “You know the pattern because you’ve probably lived it. You start a business with big dreams. You’re going to build something meaningful, create financial freedom, maybe even change your industry. And you’re going to do it without becoming one of those workaholics who miss their kids’ childhood. Then reality hits. The business demands everything. There are fires to put out, deals to close, employees to manage, and customers to satisfy. You tell yourself it’s temporary—just this quarter, just this year, just until you get past this crucial growth phase. Except the crucial phase never ends.”

• “So how do we work differently? First, you’ve got to get brutally honest about where your energy actually goes. Track it for two weeks. Not what you think you’re doing or what you wish you were doing—what you’re actually doing. How many hours are you working? How much of your mental energy is consumed by business even when you’re not physically at work? When was the last time you had a conversation with your kid that wasn’t interrupted by your phone?”

• “The biggest lie business owners tell themselves is ‘I’ll focus on family once I get the business to X.’ Once we hit a million in revenue. Once we get through this growth phase. Once we hire a COO. Once we get acquired. The goal posts keep moving. ‘Someday’ never comes.”

• “So start today. Not perfectly. Not with some grand plan that requires completely restructuring your entire life. Just start. Leave work at 6 PM today. Put your phone away during dinner tonight. Ask your kid about their day and actually listen to the answer. Tell your spouse one thing you appreciate about them.”

• “It’s not easy. It requires constant attention and regular course corrections. You’ll mess up. You’ll slip back into old patterns. That’s okay. What matters is that you notice and adjust. Because at the end of the day—and at the end of your life—the question isn’t how successful your business was. The question is whether you showed up for the people you loved and the moments that mattered.” READ MORE

THE 21 HATS PODCAST

Do You Have the Stomach for This? Part Two: This week, we take another look back at the conversations we’ve had over the past year, highlighting some more of our happiest, smartest, funniest, and most difficult exchanges, including Laura Zander on how she got the price she wanted to sell Jimmy Beans Wool, Liz Picarazzi on her confrontation with a grizzly bear, Jay Goltz on why he just might be a good candidate to turn his business into a worker cooperative, Mel Gravely on why he sold his facilities-management business as soon as it became profitable, and Jaci Russo on how she figured out how to train a series of AI agents to deliver 10 client leads first thing every morning.

• You can subscribe to the 21 Hats Podcast wherever you get podcasts.

Thanks for reading, everyone. And Happy New Year!