Some brands go for flash. But that wouldn’t be appropriate for an underwear brand like Tommy John. So naturally, they went for fit instead.

When the leading underwear and apparel company announced New York Knicks player Josh Hart as its first-ever athlete partner, it wasn’t looking to make a splash with a perennial All-Star or MVP candidate.

It was about alignment. It was about finding the right voice, the right personality and the right audience.

A perfect fit

Tommy John had already worked with Hart through The Roommates Show, his podcast with fellow NBA player Jalen Brunson. They’d seen his humor, relatability and ability to connect with fans beyond basketball. Combine that with the fact that Hart plays in the country’s largest media market, and the partnership became an easy call.

“Obviously, my lifestyle is extremely on the go,” says Hart, who, during our conversation, was in the middle of picking up his kids from school. “So I need stuff that’s really comfortable and convenient. Tommy John emphasizes those things.”

The partnership centers around Tommy John’s 2025 holiday campaign, “Gift from the Hart.” The brand’s first athlete-led campaign features a playful spot titled “‘ Twas the Hart Before Christmas,” where Hart shows off his easygoing personality while sharing his approach to gifting.

“I think it’s perfect,” he says. “The partnership is fun, loving, and a little funny — it fits my personality to a tee.”

Beyond promoting a product, Hart helps Tommy John reach new cultural spaces — blending sports, family and humor into a lifestyle message that connects with modern consumers. Known for his quick wit and easygoing charm, Hart’s trophy case may be light (for now), but he’s clearly the people’s All-Star.

For Tommy John, that’s smart brand-building. For Hart, it’s proof that athletes can win big by leading with personality over performance.

Related: Why the World’s Best CEOs Are Training Like Athletes

A partnership from the Hart

This collaboration reflects a larger trend in the sports fashion world. For years, athletes have been walking billboards for designer brands — the kind of clothes you call pieces rather than shirts and pants. That tide is changing.

Today’s athletes want to represent brands that align with their values and lifestyle. Accessibility, comfort and authenticity matter just as much as luxury. That’s why successful brands are shifting their focus from pure performance and prestige to purpose-driven storytelling that connects with athletes on a personal level.

“When I first got into the locker room, it was always like, ‘Oh, what brand are you wearing now?’” Hart says. “Now it’s more about, what’s he actually wearing today? How’s he feeling in it?”

That shift from image to intention is part of a broader movement across industries. Whether you’re an athlete or an entrepreneur, people now want to see themselves in your choices.

Related: Why Every Athlete Should Think Like a Startup Founder

Why it matters — lessons for entrepreneurs

1. Authentic partnerships outperform flashy ones.
Tommy John didn’t chase a superstar; they chose someone who genuinely aligns with their brand. In business, long-term success often comes from partnerships rooted in shared values, not just visibility. On top of that, successful partnerships start with a clear purpose. Knowing why you’re partnering guides every decision and helps build lasting, mutually beneficial relationships.

2. Lifestyle storytelling builds stronger brands. Consumers connect with how a brand fits into everyday life. By centering its campaign on comfort, family and personality, Tommy John turned an underwear ad into a lifestyle story.

3. Personality is currency. Josh Hart’s humor and relatability make him valuable beyond basketball. For entrepreneurs, it’s a reminder that authenticity and human connection can be just as powerful as titles or follower counts.

Some brands go for flash. But that wouldn’t be appropriate for an underwear brand like Tommy John. So naturally, they went for fit instead.

When the leading underwear and apparel company announced New York Knicks player Josh Hart as its first-ever athlete partner, it wasn’t looking to make a splash with a perennial All-Star or MVP candidate.

AI video tools have crossed a threshold. What used to require crews, budgets and weeks of post-production can now happen in minutes. Text-to-video generators can create actual clips that replace live-action filming — no cameras, no sets, no talent needed. Every brand, startup and side hustle can flood social feeds with polished content that would have cost thousands just a year ago.

The result is an avalanche of video content most marketers aren’t ready for. And when everyone has access to infinite content creation, the bottleneck shifts to something much scarcer: human attention.

Related: AI Made the Internet Louder Than Ever — Here’s How to Use It to Cut Through the Noise and Make a Lasting Impact

The great video inflation of 2025

Think about what happened when desktop publishing killed the printing industry’s pricing power. Suddenly, every business could create professional-looking brochures and flyers on demand. The market got flooded with mediocre design, but the cost advantages were too compelling to ignore. Printing companies that survived had to find new ways to add value beyond just putting ink on paper.

AI video is that moment for content marketing. When every solopreneur can generate Hollywood-quality product demos and every startup can create testimonial footage without actual customers, the video landscape inflates, and we’re not talking about a gradual shift. This is a supply shock.

The number of professional-looking videos published daily is already increasing by orders of magnitude. Marketing teams that were previously constrained by video budgets suddenly have access to unlimited content creation. The creative brief that once became one hero video now becomes 50 variations optimized for every platform, demographic and use case.

For marketers, this feels like winning the lottery. Unlimited content at near-zero marginal cost? What’s not to love?

But there’s a catch. When everyone has the same superpower, no one has an advantage.

Why this time is different

Previous waves of content democratization (think YouTube, smartphones or social media) expanded the pool of creators but didn’t eliminate production friction entirely. You still needed some combination of equipment, skill or time to create compelling video content. That friction acted as a natural quality filter.

AI video removes that filter in many ways. The barrier between having an idea and having a polished video is getting smaller and smaller. A text prompt becomes footage. A description becomes a testimonial. A concept becomes a commercial.

This creates what economists call a “lemons market” — when quality becomes indistinguishable at first glance, markets get flooded with mediocre products. Your audience will face an unprecedented signal-to-noise problem. Professional-looking content will be everywhere, but most of it will have nothing meaningful to say.

The brands that understand this dynamic — and position themselves accordingly — will have a massive advantage over those caught off guard.

Related: Why AI Makes Your Brand Voice More Valuable Than Ever

The coming brand extinction event

Here’s what most marketers aren’t seeing: AI video doesn’t just make content creation cheaper — it makes content forgettable. When every video looks professionally produced, none of them stand out visually. When everyone can create testimonials and product demos, the format itself loses credibility.

We’re heading toward a content landscape where production value becomes almost meaningless as a differentiator. The slick graphics, perfect lighting and smooth transitions that used to signal “professional brand” will be table stakes. Worse, they might even signal “generated content” to increasingly savvy audiences.

This shift will be brutal for brands that have built their entire content strategy around looking polished rather than saying something meaningful.

How to survive the content inflation

The companies that survive will be the ones that pivot from competing on production quality to competing on authentic insight, genuine expertise and genuine human connection. The production quality will be a given, so it’s the content strategy that will stand out.

This means treating AI video tools like what they actually are: incredibly powerful production assistants that still need direction, strategy and human judgment to create anything worth watching. The technology can generate and optimize the footage, but it can’t generate the insight that makes someone care.

Smart brands are already preparing for this shift. They’re investing more heavily in understanding their audiences, developing unique points of view and building authentic relationships that can’t be automated. They’re using AI to amplify their human creativity, not replace it.

Most importantly, they’re preparing for a world where having something meaningful to say matters more than saying it beautifully. Because when everyone can make beautiful content, the only competitive advantage left is having something worth saying.

Related: AI Slop is Everywhere We Look — Here’s How Businesses Can Avoid the AI Slop Cycle

The content inflation crisis isn’t coming — it’s already here. Early adopters are already flooding feeds with AI-generated content, and the volume is only going to increase. The brands that recognize this as an existential shift, not just a new tool to experiment with, will be the ones that survive.

Importantly, this conversation isn’t about whether AI video is good or bad. It’s about understanding that when production costs get lower, everything else about marketing changes. The rules, the strategies, the competitive advantages you’ve gotten used to — all of it gets rewritten.

Your choice is simple: Adapt to the new rules now, or get swept away by the brands that do.

AI video tools have crossed a threshold. What used to require crews, budgets and weeks of post-production can now happen in minutes. Text-to-video generators can create actual clips that replace live-action filming — no cameras, no sets, no talent needed. Every brand, startup and side hustle can flood social feeds with polished content that would have cost thousands just a year ago.

The result is an avalanche of video content most marketers aren’t ready for. And when everyone has access to infinite content creation, the bottleneck shifts to something much scarcer: human attention.

In the early days of a startup, hustle is everything. You’re answering customer support tickets at midnight, jumping into every sales call and doing ten jobs at once. It works for a while. But as your team grows and complexity kicks in, hustle starts to break. You become the bottleneck. And what once felt like momentum starts to feel like chaos.

In my time at ButterflyMX, I’ve determined that this is the moment when the smartest founders make the shift: from doer to designer, from operator to system builder.

Because the real unlock isn’t working harder; it’s building systems that scale your leadership impact.

Related: How Systems Can Help You Through the Haze, Daze and Craze of Starting a Business

Hustle gets you started. Systems keep you growing.

Startups are powered by intuition and urgency in the beginning. You move fast because you have to. Every process is ad hoc. Every decision is in your head. And if something breaks, you jump in to fix it.

But growth changes the game. Suddenly, it’s not just you; it’s 10, 30, 100 people. And they can’t read your mind. What worked with five people doesn’t work with 50.

And without systems, the cracks widen:

• New hires struggle to onboard because there’s no consistent ramp-up path.

• Team communication feels scattered, with constant context-switching.

• You’re still approving every decision because no one else knows how you think.

According to First Round’s State of Startups report, one of the top regrets among founders is waiting too long to codify processes. Why? Because what feels like “extra work” early on becomes your biggest lever later.

Hustle is linear. Systems are exponential.

The founder flywheel: Build the machine, not just the momentum

There’s a mental shift every founder has to make: from being the hero to building the machine.

Early on, you win by doing. But real scale happens when your thinking becomes embedded in how the company operates, whether you’re in the room or not.

Think of systems as your leadership flywheel. Every repeatable process, in hiring, onboarding, decision-making and communication, reduces friction and increases velocity.

Importantly, systems aren’t about bureaucracy. They’re about clarity at scale.

• A good hiring system doesn’t remove judgment; it enhances it by making criteria explicit.

• A good communication rhythm doesn’t stifle spontaneity; it ensures the right conversations happen at the right level.

• A good decision-making framework doesn’t slow you down; it prevents rework, confusion and fire drills.

And these systems aren’t static. The best ones evolve with the business. They get tighter, smarter and more nuanced as your team grows and learns.

Related: Creating Systems Is More Important Than Establishing Goals

From intuition to instruction: Building your first few systems

You don’t need to systematize everything at once. Start with your points of highest leverage.

1. Hiring:

You can’t scale without talent. But relying on “gut feel” isn’t sustainable.

Instead, turn your instincts into a process:

• Use structured scorecards to evaluate candidates on the things that matter.

• Standardize interview loops so that others can run them confidently.

• Capture feedback asynchronously to minimize bias and expedite decision-making.

2. Onboarding:

Most startups leave onboarding to chance. It’s an afterthought; a Slack invite, a Google Doc and a “let me know if you have questions.” But a new hire‘s first few weeks shape everything: their confidence, speed and cultural alignment. Intentional onboarding turns confusion into clarity. It shows people where to focus, how to win and who to turn to.

To have a clear onboarding process:

• Create a clear, role-specific checklist that guides their first 30-60-90 days.

• Record videos walking through your org chart, product vision and tools of the trade, so they can absorb context on their own time.

• Pair new hires with onboarding buddies or mentors to answer the “dumb questions” quickly and build early relationships.

• Set expectations early: What does great performance look like? What does ownership mean here?

The best onboarding systems reduce your time in the weeds while massively improving how fast and how well people ramp up. Done right, onboarding becomes a force multiplier, not a time sink.

3. Communication:

Meetings, memos, Slack channel — they add up fast.

Create clear norms for how your team communicates:

• What gets written vs. discussed?

• What’s async vs. live?

• What decisions need input, approval or just awareness?

This is how you reduce noise and focus energy where it counts.

Don’t fear process. Fear chaos.

Some founders resist system-building because they’re afraid of becoming “too corporate.” But the danger isn’t too much process; it’s not enough of the right process. Good systems are invisible when they work. They create freedom, not constraints. They let people run faster, with more autonomy, because the rails are clear.

At the same time, not everything needs a playbook. You’re still a startup. Leave space for judgment, serendipity and experimentation. The best systems balance structure with flexibility.

Related: How to Think About the Systems in Your Business

Your leadership, multiplied

The most valuable systems are the ones that scale your judgment. They let your team act with confidence and clarity, even when you’re not in the room. That’s how you move from being the center of every decision to being the architect of a company that makes great decisions on its own.

So, here’s the challenge: What’s one thing you do today, over and over, that someone else could own tomorrow, if only the system existed? Start there. Build the flywheel. And let it spin.

In the early days of a startup, hustle is everything. You’re answering customer support tickets at midnight, jumping into every sales call and doing ten jobs at once. It works for a while. But as your team grows and complexity kicks in, hustle starts to break. You become the bottleneck. And what once felt like momentum starts to feel like chaos.

In my time at ButterflyMX, I’ve determined that this is the moment when the smartest founders make the shift: from doer to designer, from operator to system builder.

You don’t need a computer science degree to build an app with AI.

Recent advances in AI have transformed app creation into something conversational and accessible to non-programmers, according to a Friday report from the New York Times. The key is an approach called “vibe coding,” which allows users to build apps and websites by giving AI tools natural language prompts rather than writing traditional code.

Users can type queries such as “make a recipe app using my fridge ingredients,” and the AI handles the entire technical implementation, including writing code for the app.

Related: This 28-Year-Old AI Billionaire Says Teens Should Spend ‘All’ of Their Time Learning One Skill

OpenAI co-founder Andrej Karpathy coined the term “vibe coding” earlier this year. In a post on X in February, Karpathy described how AI tools are getting good enough that software developers can “forget that the code even exists.” Instead, they can ask AI to code on their behalf and create an app without writing a line of code themselves.

There’s a new kind of coding I call “vibe coding”, where you fully give in to the vibes, embrace exponentials, and forget that the code even exists. It’s possible because the LLMs (e.g. Cursor Composer w Sonnet) are getting too good. Also I just talk to Composer with SuperWhisper…

— Andrej Karpathy (@karpathy) February 2, 2025

AI coding assistants can help users get started with vibe coding. One tool, Cursor, became the fastest-growing software app to reach $100 million in annual revenue in January. Another coding tool, Replit, says it has enabled users to make more than two million apps in six months. The company has 34 million global users as of November. Both Replit and Cursor have free tiers for users to experiment with vibe coding before upgrading to a $20 per month pro-level subscription.

Even tech CEOs are vibe coding. Google CEO Sundar Pichai said in June that he used Cursor and Replit to “build a custom webpage” containing all the sources of information he wanted in one place.

Despite his experience vibe coding, Pichai says Google will keep hiring human engineers and growing its engineering workforce.

“I just view this [AI] as making engineers dramatically more productive,” Pichai said at Bloomberg Tech in June.

Related: Nvidia’s CEO Says It No Longer Matters If You Never Learned to Code: ‘There’s a New Programming Language’

Vibe coding does have its downsides. AI tools can make mistakes, pose security threats and present results that look generic or similar to those found in other public projects.

Still, the U.S. market for AI code assistants is expected to grow from $1.8 billion in 2024 to $12.4 billion by 2034, indicating surging demand for vibe coding tools.

How can you vibe code an app? Here are four simple steps to help you get started.

1. Choose a vibe coding platform

Start by selecting a user-friendly AI platform that can generate code. Here are a few options:

• Lovable is ideal for absolute beginners with zero coding experience. It generates instant results.
• Replit requires understanding file structure and minor debugging. It’s ideal for users who want to learn foundational coding concepts or transition from no-code to writing code.

2. Describe the app you want to build in plain language

Draft your first prompt clearly. For example: “Design a landing page for a fictional product, including a hero section, feature list and call to action” or “Create a simple to-do list app with add, delete and mark as complete functionalities.”

The AI will create an app structure, design and logic from this description. Being more specific will improve the results.

3. Improve the app

You can improve the app after generating a first draft of it. For example, you can prompt the AI code assistant to “Add dark mode and a settings page” or “Use teal and orange colors for buttons.”

4. Hit publish

Lovable has a one-click publish feature that instantly generates a shareable link. For Replit, you have to press “Deploy,” and the build goes live on replit.dev.

Related: I Designed My Dream Home For Free With an AI Architect — Here’s How It Works

You don’t need a computer science degree to build an app with AI.

Recent advances in AI have transformed app creation into something conversational and accessible to non-programmers, according to a Friday report from the New York Times. The key is an approach called “vibe coding,” which allows users to build apps and websites by giving AI tools natural language prompts rather than writing traditional code.

Not long ago, small businesses could count on social media to deliver reach and visibility without much effort. A few consistent posts, some audience engagement and a little luck with the algorithm were often enough to get traction. In 2025, organic reach on social platforms is declining dramatically, and businesses that want to grow need to accept the new reality that social media has become a paid channel.

That may sound discouraging, but it doesn’t have to be. When you treat social media as a channel you invest in, just like paid search, email or events, you gain control over your visibility and your results. The key is learning how to spend wisely, measure effectively and make your content work harder so you don’t overspend.

Related: What It Really Takes to Stand Out on Social Media as a Business Today

Why organic no longer drives growth

The decline of organic reach isn’t accidental. Social platforms are businesses too, and their revenue comes from advertising. Over the years, algorithms have increasingly prioritized paid placements over unpaid posts. Today, even if you have a loyal following, only a small fraction of your audience will see your content unless you put money behind it.

For small businesses, this shift means that treating social media as a free marketing channel is no longer sustainable. The businesses still relying on organic alone, or posting and hoping to go viral, are essentially invisible, while those embracing paid strategies are the ones consistently showing up in feeds, building awareness and driving sales.

In other words, social media has evolved from a guessing game into a measurable marketing tool, if you’re willing to treat it that way.

Rethinking the role of budget

For many small businesses, the first barrier is financial. It’s tempting to assume that only big companies with big budgets can afford to advertise on social media, but effective campaigns can come from modest spend, too. Consistency is actually the most important part.

A good baseline is 30-50% of your monthly marketing budget going towards social, combined between organic content creation and paid social. Given a typical 15-20% marketing spend as a percent of revenue for most businesses, this can really scale with business size. Cost per click on Meta (the most common paid social platform) is typically less than $1 per click, so even a strategic spend of a few hundred dollars per month can go a long way. What matters most is showing up regularly, rather than boosting a random post here and there when sales feel slow.

Treating paid social as a line item in your marketing budget also forces you to think about return on investment. Are your dollars generating leads? Are you seeing conversions? The mindset shift here is just as important as the spend itself. Social is no longer going for virality, but is an intentional investment that you should measure like any other marketing spend you do.

Related: How Much Should You Spend on Social Media Marketing?

Making ads work harder

Once you’ve carved out a budget, the question becomes where to focus it. The most effective social campaigns tend to fall into three buckets: local awareness, lead generation and retargeting. Local awareness campaigns are essential for brick-and-mortar businesses that want to reach people nearby. Lead generation campaigns use offers, like a free consultation, discount or resource download, to turn casual scrollers into prospects you can engage with. Retargeting campaigns often deliver the highest ROI of all, reminding people who have already engaged with your website or profile to come back and take action.

Generally speaking, broad, untargeted ads are less effective than specific ones. Narrowing your focus by geography, demographics, interests or behaviors ensures your budget goes further. Retargeting is especially powerful for small businesses because it focuses your dollars on warm audiences and can multiply ROI on marketing you’re spending elsewhere.

For example, if you’re spending on email marketing or events, you can retarget those visitors on Instagram, helping keep you top of mind. Once you have some customer data, you can even build lookalike audiences to find more people who share the same traits as your best buyers.

Start by running one or two well-executed campaigns with strong creative (aka ad video!) rather than spreading your budget thin across too many initiatives. If you’ve never run social ads before, I would absolutely recommend finding an expert to support you at least for the first few campaigns.

Organic for credibility, paid for growth

If paid is the engine of growth, organic is the storefront window. Even though organic posts rarely reach new audiences anymore, they still matter for credibility. When someone clicks on your ad or visits your profile, they want to see that you’re active, trustworthy and consistent. In fact, studies show that customers are likely to look you up on social media as a way to inform their buying decision around 50% of the time — think of how many potential customers are looking at your profiles every day!

That means organic content has a new job. Posting a few times per week, sharing behind-the-scenes moments and keeping your feed fresh signals to potential customers that you’re a real, engaged business.

Organic social also doubles as a testing ground. You can use organic posts to see what resonates most with your current audience, then put spend behind the winners.

Related: 7 Paid Marketing Steps to Fuel Your Startup’s Growth

Creative and measurement go hand in hand

Once you’re paying for reach, quality matters more than ever. Ads with sloppy visuals or unclear messaging simply waste money. You need to invest in clean, professional visuals, clear copy and video if you’re going to put money behind it. Platforms reward content that keeps people engaged, and your dollars stretch further when the creative is strong.

Just as important as your creative quality is measurement. At a minimum, monitor cost per click, cost per lead and return on ad spend. These numbers tell you whether your campaigns are delivering, where to cut wasted spend and where to double down. This is another place where an expert can guide you on how to make those tradeoffs, so you can make the most of your investment.

The platforms have made it increasingly clear that if you want visibility, you have to pay for it. By budgeting consistently, focusing on high-ROI campaigns, investing in quality creative and tracking results, you can compete with far larger players and win. The businesses that embrace this shift and treat social as the paid channel it has become will be the ones showing up in feeds and converting customers.

Not long ago, small businesses could count on social media to deliver reach and visibility without much effort. A few consistent posts, some audience engagement and a little luck with the algorithm were often enough to get traction. In 2025, organic reach on social platforms is declining dramatically, and businesses that want to grow need to accept the new reality that social media has become a paid channel.

That may sound discouraging, but it doesn’t have to be. When you treat social media as a channel you invest in, just like paid search, email or events, you gain control over your visibility and your results. The key is learning how to spend wisely, measure effectively and make your content work harder so you don’t overspend.

If you’re stuck doing everything yourself in your business, you’re not alone. Most founders, CEOs and small business owners start with the best intentions of building a team, only to find themselves drowning in tasks they swore they’d hand off. The inbox piles up, the client work stretches into evenings, and that “freedom” of running your own business feels more like working overtime.

Delegating is a skill, not a personality trait, and if you’ve never learned how to do it, of course, it feels clunky or uncomfortable. The good news is that once you learn how to delegate well, you’ll unlock more time, better results and a team that’s empowered to actually support you.

Need another reason to want to delegate? Your business growth will reflect it — studies have shown that CEOs who delegate well see 33% higher growth in their businesses versus those who don’t.

So, why do so many leaders struggle to get things off their plate — and what can you do to fix it?

Related: Become a Master Delegator in 7 Simple Steps

The real reasons you’re not delegating

When business owners complain they “just don’t have the right people,” that’s often only part of the story. More often, the barrier sits in one of these areas:

1. You don’t trust the outcome: It’s tempting to think that nobody can do things as well as you. Maybe you’ve tried outsourcing once and it came back messy, or you’ve been burned by someone missing a deadline. So often, that leads to business owners holding every task hostage under the banner of “only I can do this right,” which ultimately is a recipe for burnout.

2. You’re not sure what to hand off: Many entrepreneurs operate in reactive mode, tackling whatever is in front of them that day. Without clarity on which tasks don’t need you versus which actually require your brain, it’s nearly impossible to decide what should be delegated.

3. You’re afraid it will take longer to explain: Training someone can feel slower than just doing it yourself, and there is some truth to that. However, that is a very short-term mindset. The first time you hand something off, it might take an hour to walk someone through it, but if they take that task off your plate 50 more times, that initial hour turns into a massive time savings.

4. You’re tied to your identity as the doer: For many founders, being the one who “handles it all” is a badge of honor. It feels like proof of value, proof of control or proof of grit, but if your identity is wrapped up in doing everything, you’ll eventually limit how far the business can grow.

How to get out of your own way

Delegation starts with rewiring how you approach your role as the leader. The first shift is in your approach to delegation — stop trying to dump everything at once and instead build momentum gradually. Start by handing off one small, repeatable task, something low-stakes like scheduling client calls, formatting blog posts or triaging your inbox. As you build trust and rhythm, you’ll be able to add more without overwhelming either yourself or your team.

To decide what makes sense to hand off, you need clarity on what’s actually on your plate. Spend a week tracking everything you do, then divide tasks into three categories: “must be me” (things like strategy, sales calls, final approvals), “could be me but doesn’t have to be” (email replies, calendar management, bookkeeping prep) and “shouldn’t be me” (data entry, design tweaks, admin follow-up). Start with handing off the third category.

Once you’ve identified what to hand off, create systems around it. It can be simple, starting with a short Loom video, a checklist or a quick written SOP, which is likely enough to give your team the consistency they need to deliver work to your standards. When tasks are systemized, your team can perform them confidently, and you can step back, knowing you won’t have to explain things from scratch each time.

Even when you’ve delegated the “right” way, you’ll almost certainly be tempted to step in the moment something comes back imperfect. Be prepared for this and resist that urge to take over. Instead, give feedback and let your team member fix the mistake themselves. Not only does this save you from redoing the work, but it also helps them learn and build confidence. Over time, they’ll need less handholding, and you’ll get closer to having a truly self-sufficient team.

Related: 5 Myths Preventing You From Delegating Effectively

The ripple effect of delegation done right

When you start to delegate effectively, you’ll notice changes that extend beyond your calendar.

First, your team will grow more confident with time. Instead of waiting for instructions, they’ll learn to anticipate needs and solve problems proactively. A team that’s empowered to handle tasks creates a smoother, more responsive client experience, which also takes stress off your plate.

With more time for sales, strategy and creative work, growth becomes less about how many hours you can squeeze into the day. You’ll gain time back, but more importantly, you’ll get mental space, which you can then use to grow your business even more.

Your delegation homework

If delegation still feels abstract, here’s how to make it real this month:

1. Pick one task to delegate this week: Choose something repetitive and low-risk, like scheduling social media posts or managing expense receipts.

2. Document the process once: Write out steps or record a short video walking through how you do it. Save it somewhere easy to find.

3. Hand it off fully: Don’t check in every five minutes. Give clear expectations for deadlines and output, then let your team member deliver.

4. Review and refine: Look at the results together. Provide feedback once, not five times. Then step back and let them own it moving forward.

Repeat that process with one new task every week or two. Within a few months, you’ll notice just how much lighter your load feels.

Related: Delegation is the Only Way to Scale — Here’s Why Most CEOs Do It Wrong

Getting comfortable with letting go

Delegation is uncomfortable at first. You’ll feel the itch to check in, the worry about quality and maybe even guilt that you’re not doing everything yourself. That discomfort is normal and expected when you delegate.

The longer you resist delegating, the longer you’ll stay capped at your own capacity. But once you lean into it, you’ll realize how much your business and your quality of life expand when you stop trying to do it all.

You don’t need to have delegation “figured out” perfectly to start — just start somewhere.

If you’re stuck doing everything yourself in your business, you’re not alone. Most founders, CEOs and small business owners start with the best intentions of building a team, only to find themselves drowning in tasks they swore they’d hand off. The inbox piles up, the client work stretches into evenings, and that “freedom” of running your own business feels more like working overtime.

Delegating is a skill, not a personality trait, and if you’ve never learned how to do it, of course, it feels clunky or uncomfortable. The good news is that once you learn how to delegate well, you’ll unlock more time, better results and a team that’s empowered to actually support you.

Most entrepreneurs dream of building a company, scaling it and one day capping it off in a lucrative exit. With that payout, they hope to ride off into the sunset. However, counting exclusively on future sales is a risky strategy that leaves business owners underfunded when they leave. Ideally, your business should fund your retirement years before you consider selling.

Shifting your mindset and your money is the key to building a business that thrives and actively secures your financial future.

The exit myth: Why a windfall isn’t a plan

Too many entrepreneurs treat their eventual business sale like a lottery ticket. However, a successful exit isn’t guaranteed. Market conditions can change anytime, and buyer interest may dry up. An unforeseen health issue or family responsibilities can also accelerate timelines.

It has been found that a large percentage of small business owners never succeed in selling their businesses. According to Morgan & Westfield, small businesses have a success rate between 15% and 30%. The success rate of mid-sized companies is estimated to be between 30% and 70%.

Even among those who do sell, many sell at prices below expectations. As such, an exit strategy based on the assumption that it may or may not occur is more of a gamble than a sound investment.

For this reason, forward-thinking entrepreneurs build retirement into their businesses from day one, not as an afterthought but as a fundamental part of their strategy.

Related: Why Every Entrepreneur Needs an Exit Strategy — and How to Create One

Principle #1: Treat your business like an income engine, not a piggy bank

In the early stages of your business, it’s tempting to invest every dollar back into it. However, that strategy often leads to a dangerous imbalance: your business grows, but your finances stagnate.

Start thinking of your business as an income-producing asset that can fund your operation and your financial goals. In other words, you should pay yourself a reasonable salary, make retirement contributions and accumulate wealth outside the workplace.

You will have a financial cushion with consistent income and investments, even if the business doesn’t sell.

Principle #2: Separate personal wealth from business wealth

There is often a blurring of the line between personal and business finances among entrepreneurs. Even though that may seem efficient, it creates a risk. If your business suffers or fails, your retirement prospects also disappear.

Instead, start investing a portion of your profits or salary. Included here are:

• Solo 401(k)s or SEP IRAs. Small business owners and self-employed individuals can save for retirement tax-deferred through these accounts.
• Brokerage accounts. Unlike retirement accounts, these are useful for building wealth over the long term.
• Real estate or passive income streams. Your assets shouldn’t be limited to your core business. You may consider investing in rental properties or dividend-paying stocks that offer regular dividends. In addition, selling digital products or online courses can provide a steady source of passive income.

You build a firewall between the two by diversifying your business and retirement.

Related: Why is it Necessary to Keep Personal Finances and Business Accounts Separate for Entrepreneurs

Principle #3: Use profit first — with a twist

According to Mike Michalowicz, “Profit First” encourages business owners to allocate profit before expenses, reversing the traditional income-expense-profit equation.

In retirement planning, you can apply the following logic: “Retirement First.”

You automatically deposit a fixed percentage into a retirement or investment account as soon as you pay yourself. This essentially puts it on autopilot instead of leaving it up to willpower.

If your business has a few bumps, this small habit will create a snowball effect and grow your retirement.

Principle #4: Build a sellable business, but don’t rely on selling

If you plan to sell one day, consider it a bonus — not your endgame. Until then, focus on creating a business that could survive without you. Essentially, that means:

• Creating systems and processes that are documented.
• Minimizing your direct involvement.
• Setting up recurring revenue streams.
• Establishing a strong financial record and performance metrics.
• Building a reliable, skilled team.

By taking these steps, you increase the business’s value, which is beneficial whether you sell it or pass it on. However, you’ll have built a sustainable income engine even if you keep it.

Principle #5: Don’t forget tax strategy

To plan for a successful retirement, you must consider tax strategies. To reduce taxable income and boost retirement savings, entrepreneurs can use the following tools;

• Defined benefit plans. Unlike traditional IRAs, these plans allow high earners to contribute massive amounts.
• Health Savings Accounts (HSAs). If used for medical expenses, it is triple tax-advantaged.
• Business expense deductions. If you take advantage of deductions for travel, home office and equipment, you can reduce your taxable income, which means you’ll be able to contribute more to retirement.

Talk to a tax advisor who is familiar with entrepreneurial finances. After all, whenever you save on taxes, you can invest that money in your future.

Related: 4 Ways To Eliminate (Or Significantly Reduce) Your Tax Bill

Principle #6: Think long-term, not just growth

Aiming for revenue goals or vanity metrics like 7-figure months, viral growth and investor buzz is easy. However, these achievements will not add up to long-term personal wealth in the long run.

Your business’s success shouldn’t be measured by its growth alone, but by its ability to support your life goals, especially your retirement. Regularly ask yourself:

• How much money am I consistently saving outside my business?
• Even if I never sell, could I retire in 10 years?
• How sustainable is my current lifestyle?

Rather than only relying on market trends or social media narratives, let those answers guide your decisions.

Principle #7: Consider annuities or passive investment vehicles

You might want to consider investing some of your personal wealth in low-volatility, income-producing assets once you accumulate it. Examples include;

• In addition to providing predictable returns, fixed indexed annuities protect the principal.
• Income can be generated by dividend-paying stocks or REITs.
• A CD ladder or bond ladder can provide a reliable cash flow without posing a high level of risk.

Although these options won’t provide the excitement of scaling a business, they can bring you peace of mind.

Final Thoughts: Build to live, not just to exit

There are other pathways to financial freedom than the “big exit.” For example, one of the most stable and realistic paths is to build a business that offers real-time retirement funding.

There is no need to wait for the perfect buyer, market cycle or exit for your future. Instead, let your business provide the steady energy that powers your long-term freedom, starting now.

Most entrepreneurs dream of building a company, scaling it and one day capping it off in a lucrative exit. With that payout, they hope to ride off into the sunset. However, counting exclusively on future sales is a risky strategy that leaves business owners underfunded when they leave. Ideally, your business should fund your retirement years before you consider selling.

Shifting your mindset and your money is the key to building a business that thrives and actively secures your financial future.

“Not liking to talk to people” is a weird concept in life. But take it or leave it, some of us genuinely have a less-than-normal affinity for interacting with others. Not because we hate people; people are awesome (well, not always, but mostly, people are cool).

The real issue is energy. Socializing takes too much of it. And since humans are naturally wired to conserve energy, as introverts, we end up avoiding what drains us most: talking. If they ever need a president for people like this, I’d make a good candidate. I’m naturally introverted to an almost comical degree.

Growing up, I was the kid who preferred to stay home when my brothers went out to play football. Even to this day, it takes a lot of effort to get me to leave my house. I’m the type of guy who doesn’t want to be seen, heard or heard of. I don’t want to speak, and I prefer not to be spoken to.

My ideal existence is to float through life like a ghost with Wi-Fi: present, but completely untouchable. Kind of a weirdo I am, right? Probably.

It comes with loads of disadvantages in an extroverted world, and mostly, you can barely survive in business with that weirdness. But I’ve found a way to make it work for my use case. In fact, I’m so good at coping with this, I talk to people on different calls more than half the day, and have an aggregate sum of hundreds of staff members directly or indirectly.

How? There are two approaches:

Let’s discuss both.

Related: Being an Introvert Doesn’t Make You a Bad Leader. In Fact, It Just Might Be Your Secret Weapon.

Survival: How to get by

Most conventional advice tells you to “work on your weaknesses.” But sometimes it’s smarter to let weakness be weakness and find your way around it. This is especially true when you have limited time, resources or energy. Survival mode means learning to leverage your actual strengths while developing systems that compensate for your weaknesses.

For me, not having excessive social interaction isn’t avoidance; it’s efficiency. When I force myself into energy-draining situations, I lose the capacity to excel at three other important tasks. The key is building coping mechanisms that preserve your energy for what matters most.

I found invaluable guidance in The Introverted Leader: Building on Your Quiet Strength by Jennifer B. Kahnweiler, which explains that “introversion isn’t a handicap in business, it’s a set of strengths. By leaning into those strengths and using specific strategies, introverts can manage businesses effectively without trying to be extroverts.”

Here are some of the survival strategies that keep me functional:

1. Set clear expectations: It’s easier when everyone you work with knows that you’re not a naturally social person. They don’t see you not socializing as rude. And we’re now in a world where introversion is common; most people adapt easily once they understand your approach.

2. Lead with genuine care: If you’re naturally quiet, people might misread you as dismissive. Counter this by being genuinely kind and practicing radical candor. When people know you care about them, they’re more receptive to your feedback and less likely to misinterpret your communication style.

3. Find your preferred alternative communication approach: Identify your least draining communication method and use it strategically. My preference hierarchy runs like this: Chat > Voice Messages > Phone Call > Video Call > Physical Meeting.

   Example: About eight years ago, I worked with a group of about 10 Indian developers to build a software product. I told them no calls. I communicated everything needed through writing and wireframes. We never met, we never spoke, I don’t know what they sound like and the job was still done. I wouldn’t do that now, though, because I’m better, but what I’m saying is, writing did work even for something as complicated as software design.

4. Overcompensate with natural strengths: As introverts, we excel at listening, deep thinking and thoughtful analysis. These are powerful leadership qualities that often produce good results if used correctly.

5. Work with people who can do the talking: Businesses need communicators, so it’s important to have people who naturally excel at talking. This sounds like delegation, but it’s more of smart team composition.

6. Build systems that can do the talking: For instance, documentation. If you have enough documentation, you’ll do less talking. I often create new Notion pages daily to explain, document, and keep information accessible. With good documentation, you repeat yourself less and explain yourself once.

Related: You Don’t Have to Be the Loudest Voice in the Room to Make an Impact

Transformation: How to get better

I’ve mastered the survival phase and found a way to make things work without getting excessively disadvantaged. But recently, I’ve been trying to work my way out of my discomfort.

The goal isn’t to snap out of it completely and become an extrovert (that’s neither realistic nor necessary). And it’s difficult to unlearn something that’s been a part of you since you were born. But we can always get better.

According to science, the only way to get better at talking to people is by talking to people more, which is true, as annoying as it sounds.

Exposure interrupts that “I hate this” cycle. By repeatedly facing situations we hate, our brain engages in extinction learning: the process of unpairing “the situation = stressful.” This means that with repeated exposure, our body’s stress response gradually decreases as the system realizes, “Oh… this is not that bad.”

Here’s how I’ve been exposing myself to uncomfortable situations:

1. Reducing the chance to say no to calls: I hate calls. But recently, I informed most people I work with to start calling me anytime they have something to say. Most of them know I hate calls, so this was a weird new behavior. But when you want to stop hating something, you can’t give yourself reasons to avoid it. If I ask you to call me, I promise to pick up, and also promise to call back if I’m busy at that moment. It’s like a social contract. And when the phone rings, I pick it up without thinking twice. Over time, my brain will start to understand that people won’t bite me through the phone.

2. Practicing storytelling: I’m good at writing narratives but terrible at telling them verbally. I often forget key details or lose the thread entirely. To improve, I’ve started sharing stories I would normally write with people who care to listen. Gradually, I’m noticing improvement in my ability to organize, remember and deliver verbal narratives.

3. Video call comfort: I would randomly turn on my video when joining an online call. Someone recently commented, “Kay didn’t even like calls before, and now he’s asking everyone to turn on video.” I still dislike it, but the only way to stop hating it is to do it repeatedly.

4. Daily interaction challenge: I’m planning a 180-day challenge where I initiate conversation with one unknown person daily, physically or over the phone. I haven’t started yet; these commitments are easier said than done, but I’m building toward it.

5. Improv classes: This represents the highest level of discomfort for me, but I plan to take improv classes to practice spontaneous communication in a structured environment. If I survive improv, I can survive anything.

I’ve also started viewing conversations as problem-solving sessions rather than purely social exchanges. If you have something I need and I have something you need, we’ll talk. This framing makes it easier to be consistent.

Related: These 2 Overlooked Introvert Superpowers Are the Secret to Strong Leadership and Success, Stanford University Expert Says

Bottom line

We all have weaknesses. The first step is admitting them. From there, you can either:

1. Develop strategies to work around your weaknesses = Survival.

2. Actively work to improve = Transformation.

In most cases, the survival approach is more efficient and sustainable. However, targeted growth efforts are necessary for skills that are truly essential to your success.

The secret isn’t to deny your wiring or to force yourself into someone else’s mold. It’s to optimize what you already are while strategically stretching your limits. Ultimately, introversion isn’t a bug to be fixed; it’s a feature to be optimized.

“Not liking to talk to people” is a weird concept in life. But take it or leave it, some of us genuinely have a less-than-normal affinity for interacting with others. Not because we hate people; people are awesome (well, not always, but mostly, people are cool).

The real issue is energy. Socializing takes too much of it. And since humans are naturally wired to conserve energy, as introverts, we end up avoiding what drains us most: talking. If they ever need a president for people like this, I’d make a good candidate. I’m naturally introverted to an almost comical degree.

Target on Thursday informed staff of its first major corporate workforce reduction in a decade as the retailer tries to revitalize growth after four consecutive years of sluggish sales.

According to The Wall Street Journal, the cuts affect approximately 1,800 positions, including 1,000 layoffs and 800 open roles. The move will reduce Target’s 22,000-person global corporate staff by around 8%, with 80% of the cuts affecting U.S. employees. Target is primarily reducing corporate employees based at its headquarters; the layoffs do not affect store or supply chain workers.

Affected employees will be notified on Tuesday and will continue to receive pay and benefits until January 3, as well as severance packages, the Wall Street Journal reports. Target is asking all employees at its U.S. headquarters to work from home next week.

Related: Target’s Soon-to-Be New CEO Started as an Intern at the Company. Here’s His 3-Part Turnaround Plan to ‘Get Back to Profitable Growth.’

Target’s incoming CEO, Michael Fiddelke, who takes over the role in February and currently serves as Chief Operating Officer, told staff about the layoffs in a memo viewed by CNBC.

Fiddelke, a 20-year Target veteran who will succeed longtime CEO Brian Cornell, stated in the memo that the decision to conduct layoffs was driven by the need to simplify “layers” of “complexity” to speed up decision-making.

“The truth is, the complexity we’ve created over time has been holding us back,” Fiddelke said in the memo. “Too many layers and overlapping work have slowed decisions, making it harder to bring ideas to life.”

The layoffs are “a necessary step in building the future of Target,” Fiddelke wrote.

An anonymous corporate Target employee, who works out of the company’s headquarters, told Business Insider that after Fiddelke sent the memo on Thursday afternoon, the atmosphere internally was one of “total panic.”

“We’re all trying to figure out if we’re essential team that’s going to be kept, the employee told BI.

Related: Target Teams Up With Shopify To Give Online Small Businesses Brick-and-Mortar Shelf Space

The layoffs are part of Target’s broader push to grow after years of underwhelming financial results. The retail giant has seen nearly flat or slightly negative sales growth for four consecutive years. From fiscal years 2023 to 2025, Target’s annual revenue decreased by roughly 2.3% or about $2.5 billion, dropping from $109.1 billion in 2023 to $106.6 billion in 2025.

The company’s revenue has been pressured by a combination of declining customer traffic and heightened competition from rivals like Walmart and Amazon. Shares of Target have declined by 65% since hitting a peak in 2021.

Target last made a significant workforce reduction in 2015, when the company cut roughly 3,100 jobs as part of a cost-cutting and restructuring plan under then-CEO Cornell. The 2015 restructuring followed Target’s exit from the Canadian retail market and a major data breach affecting up to 70 million individuals the previous year. Approximately 1,700 employees were laid off from headquarters, while about 1,400 open positions were also eliminated.

Target has a market capitalization of $43.28 billion at the time of writing, compared to Walmart’s $849.75 billion and Amazon’s $2.38 trillion.

Related: Walmart’s U.S. CEO Says ‘Resilient’ American Shoppers Are Opening Their Wallets and Spending

Target on Thursday informed staff of its first major corporate workforce reduction in a decade as the retailer tries to revitalize growth after four consecutive years of sluggish sales.

According to The Wall Street Journal, the cuts affect approximately 1,800 positions, including 1,000 layoffs and 800 open roles. The move will reduce Target’s 22,000-person global corporate staff by around 8%, with 80% of the cuts affecting U.S. employees. Target is primarily reducing corporate employees based at its headquarters; the layoffs do not affect store or supply chain workers.

This Side Hustle Spotlight Q&A features Channon Kennedy, 47, of Hayward, California. Kennedy works as a banker; she started her company, Kiwi Vision, which sells a “first-of-its-kind” measuring and marking tool, the Morgan Square, as a side hustle — and continues to run it as one today. Responses have been edited for length and clarity.

^{Image Credit: Courtesy of Kiwi Vision. Channon Kennedy.}

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What was your day job or primary occupation when you started your side hustle?
I still have a day job. I work as a banker for Silicon Valley Bank, focused on startup founders, primarily engaging with early-stage entrepreneurs and pre-seed companies and helping them navigate their journeys.

What inspired you to start your side hustle?
The inspiration for the Morgan Square came from a deeply personal story. At just two years old, Morgan Dean Hebberd, a spirited boy from New Zealand, was diagnosed with leukemia. After a six-year battle marked by courage and resilience, Morgan passed away at the age of eight. In his final months, his father, Gary — who is a close friend of mine — took time off work to be with him, cherishing every moment.

Not long after, Gary, a craftsman, shared with me a heartfelt wish: He wished he’d had a tool that could have helped him work faster, so he could have spent even more time with his son. That conversation stayed with me. It became the seed that grew into the Morgan Square — a tool designed to make woodworking more efficient.

Related: This Mom’s ‘Scrappy’ Side Hustle Started in Her Garage — Now It Makes $5 Million a Year

What were some of the first steps you took to get your side hustle off the ground? How much money/investment did it take to launch?
The first steps were patent and trademark searches, finding a manufacturer and creating prototypes. I had to establish an LLC, secure insurance and handle all the foundational legal work. Prototyping alone was costly, so when someone wrote me a $50,000 check to support the vision, that gave me the initial runway. Beyond that, I’ve bootstrapped everything.

Are there any free or paid resources that have been especially helpful for you in starting and running this business?
Yes, two in particular. First, SCORE.org, which connects entrepreneurs with retired business leaders for free mentoring. My mentor has been invaluable in helping me navigate everything from financials to patents. Second, the Black Chamber of Commerce, which provided resources on funding, introductions and exposure in the community. Those two resources, along with the business knowledge I gained as a banker, have been critical.

^{Image Credit: Courtesy of Kiwi Vision}

If you could go back in your business journey and change one process or approach, what would it be, and how do you wish you’d done it differently?
I wish I had invested in the right PR and marketing support earlier. I wasted a lot of time and money teaching myself Amazon ads and running into unreliable people who overpromised and disappeared with payments. Better vetting and earlier professional help would have saved me both money and stress.

Related: After an Eye-Opening Trip to Home Depot, This Grandfather Started a Side Hustle on Amazon — and Did About $500,000 in Sales Last Year

When it comes to this specific business, what is something you’ve found particularly challenging and/or surprising that people who get into this type of work should be prepared for, but likely aren’t?
How expensive prototyping is, and how many iterations it takes before you get it right. You can’t expect the first or second version to be perfect. It’s a slow process, and you need patience and a financial runway.

Can you recall a specific instance when something went very wrong? How did you fix it?
At my first major trade show, the International Woodworking Fair in 2022, my website wasn’t set up properly, and I wasn’t thoroughly educated on POS functionality. In the middle of making sales, the system flagged my transactions and stopped me from accepting payments. I had to pivot on the spot, pulling out Excel spreadsheets and my Square reader to manually take orders. It was chaotic, but we still sold out and shipped everything once we got back home.

How long did it take you to see consistent monthly revenue? How much did the side hustle earn?
During our first year, amid the pandemic, we generated less than $1,000 initially but closed the year with $5,000 in total revenue. By our second year, that figure grew significantly to more than $60,000, even without a formal marketing strategy in place. Not bad for a niche product and a young brand still establishing its presence and credibility.

Related: Sisters’ Savory Side Hustle Averages $7,000 a Month: ‘Reward We Didn’t Feel in a Corporate Job’

Consistency is still a challenge; it spikes whenever I’m at trade shows. Online, the product doesn’t always grab attention until people can actually hold it. That’s why I plan at least one or two shows per quarter moving forward. I launched the Morgan Square in March of 2020, just as the pandemic hit, and launched on Amazon in 2021. However, despite the challenge of most trade shows being cancelled during the initial years of operation, we sold an initial 50 units. As the economy normalized, we’ve seen a rapid transition and upward trajectory of sales. I grew to over 1,000 units sold in 2023 and over 3,000 units sold in 2024.

^{Image Credit: Courtesy of Kiwi Vision}

What does growth and revenue look like now?
Thanks to consistent effort and persistence, we’re now seeing a steadier stream of income, averaging around $4,000 per month. With the Morgan Square now featured in several retail locations and across multiple online channels, stronger partnerships with our retail partners and a dedicated marketing team executing a cohesive strategy, we anticipate continued growth and increasingly consistent sales.

How much time do you spend working on your business on a daily, weekly or monthly basis?
I work on my business every single day — early mornings, evenings and weekends — on top of my day job. Some days are focused on shipping orders, others on certifications, accounting or outreach. It depends on the month and what deadlines or opportunities are in front of me. But there’s not a day that goes by that I don’t do something for the Morgan Square.

Related: This Mom’s Creative Side Hustle Started As a Hobby With Less Than $100 — Then Grew Into a Business Averaging $570,000 a Month: ‘It’s Crazy’

What do you enjoy most about running this business?
The joy of seeing an idea come to life — and that people actually want it. Every sale excites me. Packaging boxes feels like wrapping gifts, and I don’t get tired of it. It’s humbling and energizing to know that people value what I’ve built.

What is your best piece of specific, actionable business advice?
Be intentional. Write down your goals and act on them. In 2025, I made a list of where I wanted to show up and what I wanted to achieve, and I followed through. That intentionality is how I ended up at trade shows, in new stores and ultimately in Home Depot. Don’t just keep moving things to “tomorrow.” Take deliberate action.

This Side Hustle Spotlight Q&A features Channon Kennedy, 47, of Hayward, California. Kennedy works as a banker; she started her company, Kiwi Vision, which sells a “first-of-its-kind” measuring and marking tool, the Morgan Square, as a side hustle — and continues to run it as one today. Responses have been edited for length and clarity.

^{Image Credit: Courtesy of Kiwi Vision. Channon Kennedy.}