This Side Hustle Spotlight Q&A features Krista LeRay, the 34-year-old founder of needlepoint store Penny Linn. She lives with her husband and two children in Westport, Connecticut. Responses have been edited for length and clarity.

^{Image Credit: Courtesy of Penny Linn. Krista LeRay.}

Want to read more stories like this? Subscribe to Money Makers, our free newsletter packed with creative side hustle ideas and successful strategies. Sign up here.

What was your day job or primary occupation when you started your side hustle?
Before starting Penny Linn, a new-age needlepoint store offering hand-painted canvases, accessories and more, I was a full-time influencer running my blog, Covering The Bases. I started the blog in 2013, but I only took it full-time about a year before starting Penny Linn. While managing the blog, I had a corporate career at Major League Baseball, where I worked on the social media team for over five years.

Related: He Spent $36 to Start a Side Hustle. Now the Business Earns 6 Figures a Year — With Just 1-2 Hours of Work a Day: ‘Freedom.’

When did you start your side hustle, and where did you find the inspiration for it?
I initially learned to stitch from my grandma, who inspired the name of the business, and then I really got into it in college at the University of Kentucky. I picked it back up again in 2018 when I started stitching custom belts for my dad and husband, and a ring bearer pillow for my wedding in 2019. Little did I know that this would be the perfect hobby to fall back in love with as the pandemic approached.

As I got back into stitching, I quickly stitched through my stash of canvases and was disappointed with both the in-person and online needlepoint shopping experiences. It felt antiquated; there weren’t many sites with a good user experience, a handful of the shops made you call to order, and the designs felt very mature. I found myself wishing there were more fun and better accessories and canvases, so I started making them after my search came up short.

^{Image Credit: Courtesy of Penny Linn}

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?
When I started painting my own canvases, I wasn’t even in the mindset of starting a business; it was still just a hobby for me. I probably spent under $100 buying a blank canvas on Etsy and paint at Michaels, and painted the infamous Ralph’s Coffee cup for myself. When I shared it on my Instagram, I had an overwhelming number of followers ask to buy one, so I knew my followers were also interested in needlepoint.

As I began searching for cuter accessories for myself, I found that many custom items had a 100-item minimum. At the time, I had a business bank account for my blog, so I used that money to order the inventory and knew that I could at least sell 90 of them to my followers who also needlepointed. After making a few canvases and seeing the demand, I realized I had enough ideas to launch a larger collection online. So I bought the smallest Shopify package, started sourcing needleminders and project bags, and recruited my friends and family to help paint canvases.

All in all, I spent about $5,000 on the initial inventory for our accessories and an additional $2,000 on shipping materials, canvas tape, etc., but none of this accounted for my time painting the canvases one by one, which was the biggest investment.

Related: These 31-Year-Old Best Friends Started a Side Hustle to Solve a Workout Struggle — And It’s On Track to Hit $10 Million Annual Revenue This Year

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?
Looking back on how I built my business, it’s a catch-22; if I had known what I know today, I might have done it differently. However, having my hands in every aspect of the business has brought me a great deal of knowledge and appreciation that continues to shape the business.

In the beginning, I hand-painted nearly every canvas, which took many, many hours, but it kept costs low since my labor was essentially free and gave me control over my inventory. If I had known that people outsourced painting, it would have saved me so much time and energy, but doing it myself taught me the value of a hand-painted canvas.

Similarly, I wish I had hired people at the beginning to take more off my plate, but by doing it all, I learned valuable lessons and knew how I wanted every aspect of the business to run. I don’t think Penny Linn would be such a thoughtful and impactful brand today if I hadn’t had my fingers on every aspect of the business in the beginning.

Related: I Interviewed 5 Entrepreneurs Generating Up to $20 Million in Revenue a Year — And They All Have the Same Regret About Starting Their Business

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?
The reason Penny Linn has been so successful as a business, and also in reviving the cultural love for needlepoint, is that we brought much-needed innovation to the industry. I never expected the amount of pushback from vendors and industry vets I received. Across the board, people pushed back on our ideas and how we ran our business.

Today, we have found partners who believe in our growth and are building with us. When we launched our acrylic line in 2022, there was so much chatter online that it wasn’t innovative or unique, but today we hold a patent for the design, and it’s one of our bestselling lines. We also take a slightly smaller wholesale margin than the industry standard because I believe in making needlepoint accessible. Our wholesale partners were initially adamant that it wouldn’t be successful, but it has proven otherwise. I developed a thick skin while blogging and learned to shut out the noise, which has followed me into Penny Linn as we continue to shake up the industry.

^{Image Credit: Courtesy of Penny Linn}

Can you recall a specific instance when something went very wrong? How did you fix it?
I vividly remember one of our first bag launches, which did not go as planned. It was a beautiful project bag with leather and PVC that we sold through so quickly! As I was packing them, I tested a few of the zippers and was very disappointed to find that they stuck and were difficult to open, despite the samples working perfectly. I reached out to each customer who had ordered them and let them know that the bags weren’t up to our standards. I offered them a full refund if they wanted to return the bag or a discount if they wanted to keep it.

This became one of my biggest rules in business: When anything goes wrong, I need to take ownership and work to rectify it immediately. Our community was beyond appreciative of how proactive we were, and most ended up keeping the bags. We put the rest of the bags on clearance and now work with our team and vendors to ensure we have quality control measures in place.

How long did it take you to see consistent monthly revenue? How much did the side hustle earn?
In the first six months after we launched, the only consistent revenue was what we generated during launches. Everything would sell out so quickly that we wouldn’t have any inventory left until the next launch. We would often have a day or two without sales in between launches, which wasn’t a sustainable way to run a business. To prevent this, we started producing more inventory and introduced our Penny Linn Collective, allowing us to bring on designers who expanded our offerings. Our designer collective has been fruitful for us over the past five years, and we continue to grow it today.

We started seeing more consistent revenue in year two, doing just over $30,000 per month. The popularity of our launches started to level out, and we could better forecast inventory to keep our income steady. It was such a big deal for us at the time to reach these numbers, but we do that in a day now. Each year has been drastically different in terms of demand, and about every six months, we reach an inflection point where we need to increase quantities even more.

Related: This Couple’s ‘Scrappy’ Side Hustle Sold Out in 1 Weekend — It Hit $1 Million in 3 Years and Now Makes Millions Annually: ‘Lean But Powerful’

What does growth and revenue look like now?
It’s been really exciting that Penny Linn has doubled or tripled each year. In 2024, we did $4.4 million in revenue, and we have already surpassed that and are on track to double it in 2025. We are currently averaging $570,000 per month. Whatever I think our ceiling might be, we come in and double it each year. Our growth has been so explosive that I do expect it to start leveling out in the next year or so, but there is still so much opportunity for the business.

My mind is always racing with new ideas for the brand as we expand our product offering, launch new designers under the Penny Linn Collective and bring new accessories to market. Our store opening in Norwalk, Connecticut, earlier this year was a huge milestone for us, and now we are exploring what more stores might look like. I don’t see our growth slowing down anytime soon.

^{Image Credit: Courtesy of Penny Linn}

What do you enjoy most about running this business?
I honestly love what I do so much and find great fulfillment in it. I feel so much pride, excitement and joy thinking about what we’ve created at Penny Linn and the business I’ve built in under five years. It’s nothing I could have ever imagined as my career or what I expected Penny Linn to grow into. We haven’t seen many bumps in the road yet, and keep having success after success, which energizes me to keep going.

I pride myself on the fact that Penny Linn is “by a stitcher for a stitcher,” and there is nothing more satisfying as a needlepointer to want something in my collection and to be able to make it. I’m privileged to have the ability to work with our vendors to create the products of my dreams, and it’s just as exciting to see how much our community loves them.

I also find so much joy in the change we have brought to the industry and how we have been able to bring needlepoint to the forefront for a new generation. It’s crazy to sit back and think that my brand has revived a centuries-old tradition and built it into something that will continue to live on and evolve for generations to come.

Related: These Friends Started a Side Hustle in Their Kitchens. Sales Spiked to $130,000 in 3 Days — Then 7 Figures: ‘Revenue Has Grown Consistently.’

What’s your best business advice?
The first is, “If you don’t ask, the answer is always no.” People are often scared to reach out because they are afraid of rejection, but my motto is always to ask, and if they don’t reply, it’s still not a no. If they don’t respond, it’s not the end of the world, but the opportunity for the answer to be yes is so much greater.

My second is to learn the difference between constructive feedback and criticism. If someone doesn’t like you or your business, they will never have anything nice to say, and it’s not worth listening to. However, if they are a loyal fan and a frequent shopper, and they comment on how a product or process might be improved, it’s worth listening to. It’s easy to get lost in the negative feedback, but the faster you learn what is worth listening to, the better decisions you will make for your business.

Every day, business owners encounter large and small decisions that could significantly influence their company’s health and growth. Having the right tools and technology can be just as crucial as building a strong team, particularly as more resources become accessible to businesses of all sizes. That’s one reason AI adoption is climbing fast.

According to new research from Intuit QuickBooks, 68% of small businesses now use AI regularly, and most (74%) say it’s helping them accomplish more with less. Unpacking how AI can help your business in meaningful ways starts with understanding what it can do for you efficiently.

What’s the difference between generative and agentic AI?

GenAI has become one of the most familiar and accessible technologies in recent years, built into everything from search engines to accounting platforms. Today, 56% of small businesses using AI rely on these generative tools. GenAI excels at automating content creation: summarizing, translating and drafting responses, which helps business owners stay responsive, make faster decisions and reduce manual work.

However, even greater value can be achieved by layering in agentic AI, although only 9% of businesses currently utilize it. Unlike GenAI, agentic AI takes action on your behalf. These AI agents are context-aware, meaning they can handle multi-step processes and explain their reasoning behind decisions, drawing on past data to provide business owners with clarity and control.

In short, while GenAI helps you create, agentic AI helps you execute. Used together, they empower small businesses to achieve more with less. Among businesses using AI, 41% say their revenue has increased, and 86% consider their business in good health.

So, how can businesses best leverage AI tools? Here are five areas where businesses can infuse AI into their workflows.

Related: How AI Is Leveling the Playing Field For Small Businesses to Compete With Industry Giants

Marketing

In the next three months, 47% of small businesses say nothing would help them more than a successful marketing campaign. It’s no wonder 43% are already using AI to sharpen their marketing efforts. GenAI can create copy and images for social posts, email campaigns and digital ads. Let agentic AI manage audience delivery based on customer behavior, run A/B testing and track results.

How to get started: Start small by leveraging GenAI features in the tools you already use, such as social media scheduling. For your next marketing campaign, consider using agentic AI to experiment with email subject lines, optimize send times or segment audiences based on purchase behavior or engagement history. The key is to test and learn what resonates most with your audience. To go a step further, use a marketing platform that can analyze your customer communications and create unique campaigns based on their interaction with your product or service.

Customer service

Thirty-six percent of small businesses already use AI for customer service. Among them, 74% report higher productivity, and 24% have actually shortened their workdays. That’s time you can put back into your business. GenAI uses natural language capabilities to generate replies and power chatbots based on user prompts. While agentic tools can respond to customers as well, they go further with their ability to autonomously plan, reason, and take actions to resolve customer issues, such as routing requests, flagging urgent communications, tracking follow-ups and even making changes to customer records without human intervention.

How to get started: Try creating a library of automated templates for your most common questions first. Once you’re comfortable, test agentic features that can prioritize or escalate requests for you.

Related: AI Is an Incredible Customer Service Asset — But It’s Not Flawless. Here’s How to Avoid 4 Common Mistakes.

Admin and operations

GenAI can quickly summarize meeting notes, write reminders and create checklists, reducing everyday friction. Meanwhile, agentic AI can multiply administrative efficiency through automated actions. After a client call, for instance, it can create follow-up actions, schedule meetings, log notes into your CRM or assign tasks after a call — no manual effort required. Roughly a third (33%) of small businesses are using AI to handle administrative tasks, often through tools they already rely on.

How to get started: Simply turn on AI features in your calendar, email or project management apps. Then, explore ways to connect these tools for even smoother workflows.

Data and insights

AI is changing the way small businesses understand their numbers. GenAI is well-suited for summarizing reports, spotting trends and quickly answering “what happened?” within a business. Agentic AI drives tasks like forecasting future trends, alerting you to anomalies and connecting real-time data to your planning tools. Today, 32% of small businesses use AI to help make sense of their data.

How to get started: Ditch the spreadsheets and input your business performance data into an AI-powered software to get a clear baseline of your business health. Try AI-powered dashboards that notify you when key metrics shift, so you can stay ahead of the curve. This can help you with automating business reports, but can go as far as even helping you predict changes in cash flow.

Related: AI Can Turn Your Raw Data into Actionable Insights and Visual Stories

Bookkeeping and finance

The survey also found that 29% of small businesses use AI for bookkeeping, and 15% adopted it based on a recommendation from an accountant or consultant. With GenAI, business owners can automatically categorize transactions and track cash flow, so nothing slips through the cracks. To streamline workflows even further, agentic AI capabilities can automate account reconciliations, flag irregular transactions and send personalized invoices tailored to clients, helping businesses get paid faster.

How to get started: Look for a connected AI-powered platform that unifies your business data, automates accounting tasks and proactively delivers insights and recommendations, so you can spend less time on manual work and focus on growing your business with confidence. And, if you are using an accountant, pairing the power of AI with human expertise will lead to a clearer view into your finances.

AI is already helping small businesses work smarter, but business growth comes from using it with purpose. Generative and agentic tools each play a role, and when combined with your expertise, they can support better decisions, faster follow-through and stronger operations. If you’re one of the 1 in 4 small businesses not yet utilizing AI, here’s my advice: start in one area, build from there and keep moving forward.

When it comes to entrepreneurship, picking up a new hobby probably isn’t top of mind. You’re already juggling a packed schedule — and maybe you already have hobbies you love. Still, it should come as no surprise: hobbies are good for you.

In fact, a 2023 study published in Nature Medicine found that adults aged 65-plus who engaged in hobbies reported better health, higher life satisfaction and greater happiness. And in my own experience, embracing a musical hobby has been one of the most effective ways to improve my mental health, reduce stress and maintain a sense of balance as a business owner.

You don’t need to be a lifelong musician to benefit. Music offers a creative outlet and a mental reset — something all entrepreneurs need more of. Whether you’re learning an instrument, singing, or simply listening more intentionally, musical hobbies can change how you show up in business and life.

Let’s break down three key ways music can positively impact entrepreneurs.

1. Music relieves stress — fast

Entrepreneurship comes with constant pressure — deadlines, decisions, responsibilities. Stress builds up over time, and if left unchecked, it can lead to burnout, anxiety, trouble concentrating or even depression.

A musical hobby can serve as a powerful stress reliever. Studies show that playing an instrument or singing can lower cortisol levels and reduce anxiety. Even listening to music intentionally — without multitasking — can focus your mind and create a sense of calm.

Of course, not everyone has time to learn an instrument. That’s okay. For me, just putting on a record and truly listening helps me reset. Whether it’s practicing piano, jamming with friends or listening to a favorite playlist, music becomes something to look forward to — a reliable, restorative escape.

Related: How I Turned My Hobbies Into Profitable Side Businesses With My Friends — Without Losing the Joy

2. It builds transferable skills

Musical hobbies don’t just relieve stress — they sharpen your mind. Actively engaging with music can improve memory, concentration, and cognitive flexibility. For entrepreneurs, that’s a powerful edge.

Learning to play an instrument, for instance, requires self-discipline, time management and resilience — all skills that mirror the entrepreneurial journey. It challenges you to get comfortable being a beginner again, to practice patience, and to build momentum over time.

Musical practice enhances:

• Creativity
• Problem-solving
• Focus
• Coordination
• Confidence
• Discipline
• Learning agility

And perhaps most importantly, it reminds you that growth comes from consistency — a principle that applies just as much in business as it does in music.

Related: Every Entrepreneur Needs a Hobby Separate From the Company — Here’s Why

3. It strengthens your brain

Engaging with music activates multiple regions of the brain — the same areas responsible for memory, movement, emotional regulation and complex thinking.

A 2023 study found that musical training enhances auditory processing and working memory. According to AARP, playing an instrument lights up your brain, improving functions like listening, reading, and recall — and may even help grow new neural pathways. That means better cognitive health, greater adaptability, and increased creative thinking.

For entrepreneurs who rely on clear decision-making, creative problem-solving and rapid learning, that kind of cognitive workout is invaluable.

Treat music as self-care, not a side project

Musical hobbies give entrepreneurs more than just stress relief. They offer a creative space to disconnect from the daily grind, while strengthening the mental and emotional muscles that help you lead, build and grow.

Even if you can’t commit to lessons or learning an instrument, find ways to engage with music that work for your schedule. Deep listening, group classes, or even karaoke nights can reignite joy and spark inspiration.

Entrepreneurship demands everything from you — but that doesn’t mean you can’t take something back. A musical hobby could be exactly what you need to recharge, grow and show up better in every area of your life.

A new animated movie made mainly with AI could challenge the time and resources it takes to put together a Hollywood production.

According to a Sunday report from The Wall Street Journal, OpenAI is giving its tools and computing resources to a new feature-length movie called “Critterz,” which follows the journey of forest creatures who embark on a quest after a stranger intrudes on their home.

Chad Nelson, a creative specialist at OpenAI, conceptualized “Critterz” three years ago while experimenting with OpenAI’s image generation tool Dall-E. It was originally a short film funded by OpenAI that was released in 2023. Nelson has since joined forces with movie production companies in London and Los Angeles to make his vision of a feature film a reality. It’s unclear if OpenAI will be marketing the full-length movie.

Related: Meta Says Its New Movie Gen AI Is an Industry First — But a Demo Shows It Isn’t Perfect

Nelson says that the film will demonstrate what OpenAI’s tools can do, creating a highly visible (the plan is to debut at the Cannes Film Festival in May) use case for the technology.

“OpenAI can say what its tools do all day long, but it’s much more impactful if someone does it,” Nelson told WSJ. “That’s a much better case study than me building a demo.”

After being introduced at Cannes, “Critterz” is expected to be released in theaters globally next year. In a press release on Monday, Vertigo Films said the film will be funded by Vertigo’s Paris-based parent company, Federation Studios.

With a budget of less than $30 million, the movie would cost less to make than a standard Hollywood film. For reference, major Hollywood productions like Disney’s “Tangled” cost over $200 million to create, while the studio’s “Tarzan” cost $130 million. If successful, it could cause Hollywood to take notice and use AI for future films.

Related: A Movie About Sam Altman’s Ouster and Wild Week at OpenAI Is Currently Filming. Here’s Who’s Portraying the Tech CEO (and His Nemesis, Elon Musk).

“Critterz” would also take less time to produce: The production team is aiming to create it in nine months instead of the standard three to four years. Production has started, with casting decisions aiming to go out within the next few weeks.

Other Hollywood studios have already begun experimenting with AI. In July, Netflix disclosed that it had used AI to generate a scene on an Argentine TV show called “El Eternauta.” Meanwhile, Disney has experimented with tapping into AI to create clones or digital body doubles of actors.

Entertainment companies have also pushed back against unauthorized AI use. In June, Disney and Universal filed the first major Hollywood lawsuit against AI startup Midjourney, alleging that the startup copied its characters from copyrighted works without permission.

Related: Universal Pictures Just Added an Anti-AI Legal Warning to the End of Its Movies, Including ‘How to Train Your Dragon’

You’ve heard this story before: a couple of college kids launch a startup from their dorm room. Surrounded by engineers, finance majors and future founders, venture capital wasn’t just common — it was expected. So when my co-founder and I launched Prepory, our college admissions coaching company, we assumed we’d need funding to be taken seriously.

We entered a pitch competition and came in second. No check. We reached out to investors. No bites. We had a choice: give up or keep building.

We kept building.

What started as a one-person operation helping students in our local community has grown into a seven-figure, global company with nearly 100 team members. We’ve supported over 14,000 students, partnered with school districts and institutions in multiple countries and built one of the most trusted brands in college admissions — all without a single outside investor.

Here’s why we said no to VC, and why bootstrapping was the smartest decision we never planned to make.

The pressure to raise

In elite academic circles, starting a business often goes hand in hand with chasing venture capital. I pictured the high-stakes pitch rooms, the dramatic investor meetings — scenes straight out of The Social Network. But after our early efforts fell flat, we stopped trying to win someone else’s approval and turned our focus inward.

We obsessed over our product, our client experience and our outcomes — not “scale.”

One month before our one-year mark, we hit $100,000 in revenue. It wasn’t a headline-grabbing number by Silicon Valley standards, but it proved something more important: we didn’t need permission to grow. We just needed to execute.

Related: Most Startups Ignore This One Asset That Makes or Breaks Their Success

What bootstrapping taught us

In hindsight, bootstrapping didn’t just work — it shaped the business in ways VC money never could.

Every dollar mattered, which meant we tested fast and paid close attention to what customers wanted. Client feedback shaped everything. We pivoted early on from a B2C model to B2B — realizing that one school contract could bring the same revenue as ten individual clients. That insight wasn’t born from a boardroom; it was born from necessity.

Bootstrapping also made me a better leader. I didn’t start by managing dozens of people. I started with one, then five, then ten. That kind of slow, intentional growth gave me room to develop as a leader — learning how to listen, communicate clearly and lead with clarity and care. There was no pressure to scale overnight, so we could prioritize culture, values and quality.

The hidden cost of raising too soon

VC can be a powerful accelerator — but if you raise too early, it can also be a trap.

Many founders take funding before they’ve found product-market fit. They shift their focus from solving customer problems to pleasing investors. Instead of building a strong foundation, they’re stuck managing burn rates and expectations. Teams get stretched. Quality suffers.

We built slowly. That meant we stayed close to our mission and recruited talent who were energized by the opportunity to build something meaningful. Today, we outperform companies twice our size because we’ve built a team that shows up with purpose — and we’ve stayed aligned with what matters most: helping students reach their full potential.

Related: How to Scale a Business Without Wasting Millions (Or Collapsing Under Your Own Growth)

Should you bootstrap?

Ask yourself this: What do you actually need the money for?

If you’re building a product that truly requires upfront investment — hardware, tech or time-sensitive development — funding may make sense. But if you’re starting a service-based business, you might not need capital to get traction.

Bootstrapping requires resilience, patience and a tolerance for delayed gratification. But it gives you full ownership of your company, your vision and your decisions. Today, we have the freedom to invest in growth on our own terms.

People still ask if we’d raise money now. My answer? Not unless we have a strategic reason to. Not because I’m anti-VC, but because we no longer need it.

Bootstrapping gave us something far more valuable than capital: it taught us how to build a resilient, values-driven, adaptable business. And if we ever decide to raise, we’ll do it from a position of strength — not survival.

Running a business comes with enough challenges without having to manage a stack of disconnected tools. If you find yourself wasting time moving between platforms instead of focusing on growth, Sellful may offer a more efficient solution.

Sellful is a fully integrated business platform that combines website building, CRM, marketing, invoicing, scheduling, and project management in a single dashboard. Designed with agencies and entrepreneurs in mind, it supports full white labeling so you can brand the system as your own. You can manage everything from client portals to payroll, all in one place. The lifetime Agency Plan is currently available for $349.97, down from $1,497, but only for a limited time.

What can Sellful do?

You don’t need to be tech-savvy to use Sellful. It has a unique AI-powered website builder that lets you launch sites, landing pages, and sales funnels in minutes. You can manage product sales, inventory, and payments across 20 supported gateways. Built-in CRM tools help you track customer relationships and automate communication via email and SMS. Sellful also includes tools for scheduling, course and membership management, help desk support, and team collaboration.

Agencies can manage multiple client accounts, customize the platform for each business, and handle internal tasks like HR and accounting. With integration support for more than 5,000 apps, Sellful is designed to fit into your existing workflows without disruption.

There are no limits on users, contacts, or hosted websites. One upfront payment gives you lifetime access, allowing your business to scale without additional subscription costs.

For a limited time, you can get a Sellful Lifetime Agency Plan for $349.97.

Sellful – White Label Website Builder & Software: ERP Agency Plan (Lifetime)

See Deal

StackSocial prices subject to change.

Here’s a moment every technical leader knows too well: you’re in a room full of executives, creatives, agents or business leaders — and you’re the only one who speaks “tech.” Maybe you’re a new CTO. Maybe you’re just the most technical person in the room. You have ideas that could solve real problems. But no one gets what you’re saying.

I’ve been there more times than I can count — at UTA, the Clippers and now as co-founder of SkaFld Studio. And here’s what I’ve learned the hard way:

It doesn’t matter if you’re right if no one understands you.

Your job isn’t just to solve complex problems. It’s to help others see how those solutions fit their world. Harvard Business Review backs this up: the best leaders use clear, resonant language to make complexity approachable. That requires more than just communication skills — it requires empathy, strategy, and what I call the Translator Mindset.

The instinct is to lead with jargon, credentials or cleverness. But that only creates distance. The Translator Mindset is about meeting people where they are, then guiding them somewhere new. Clarity matters more than ego. Connection matters more than correctness.

Related: How to Build and Sustain Deep, Meaningful Business Relationships (and Why It’s the Key to Long-Lasting Success)

What the Clippers taught me about influence

One of my most valuable lessons came during my time with the LA Clippers, at a moment when the entire league was embracing analytics. We had the data. It felt like we had the answers. But I was walking among legends — Jerry West, Doc Rivers — and when they have an opinion, you listen.

During a tense draft season, the analytics team wanted to cast a wide net, calling dozens of prospects to increase our odds. But the old guard insisted we focus only on the top few. And more importantly, they wanted those calls to come from someone with real influence — one of our big names.

They were right. Every player who got a call from one of our top voices came on board.

The data team wasn’t wrong. But they were missing the bigger picture: it wasn’t about efficiency — it was about influence. That moment showed me how instinct and data don’t need to compete. But someone has to bridge the gap.

Why tech initiatives really fail

Most tech ideas don’t fall apart because they’re flawed — they fail because they’re misunderstood.

I’ve watched engineers try to bury doubt with detail. But doubt isn’t rational. It’s emotional. Disruption often feels like displacement. Confusion can trigger fear. And fear doesn’t get solved by specs.

Empathy is a strategy. Before I pitch anything technical, I ask myself:

• What does this audience actually care about?
• Where might they feel threatened?
• How do I make them feel like co-owners of the solution?

In the early days of my career, I used jargon as a defense mechanism. It made me feel competent. But it didn’t build trust. I had to unlearn that habit and retrain myself to reframe, simplify and connect. Once I did, everything changed — not just for me, but for the people around me. I went from being a translator to being the person who helped everyone in the room align.

3 tools to help you communicate tech better

Whether you’re the only technologist in the room or just the one willing to speak up, your job is to create clarity, credibility, and connection. These tools will help:

1. Reframe, don’t repeat
When someone pushes back, don’t double down on detail. Reframe their concern in their own language. Make them feel heard — and then offer a clearer path forward.

2. Start with outcomes
Never open with the tech stack. Open with the result. Instead of “We’re using containerized microservices,” say “We’re cutting load times by 70% so fans don’t drop off before tipoff.”

3. Speak their language
Metaphors work. To a producer, AI is a script assistant. To a VC, it’s a high-frequency analyst. Familiar language lowers resistance and builds buy-in.

Related: 14 Proven Ways to Improve Your Communication Skills

You’re the bridge

You’re not in the room to explain code. You’re there to turn potential into progress — to connect software with story, abstraction with action and fear with adoption.

That’s leadership. Done well, it builds momentum, earns trust, and drives real change.

And it starts not with speaking louder — but with being understood.

The owner of a luxury yacht worth around $940,000 had to swim to shore after his brand new 85-foot vessel, dubbed “The Dolce Vento,” launched for the first time on Tuesday off the coast of northern Turkey.

After hitting the water for its maiden voyage, the boat turned to its side and began to sink a couple of hundred feet offshore. A video widely shared on social media captured the boat being led into the water, and one person jumping as it sank.

Related: Video Shows Las Vegas Billionaire Traveling the East Coast With Two Megayachts — One Just Carries the Toys

#DolceVento is a motor yacht with an overall length of 24 m. The yacht is the largest built by Medyılmaz Shipyard from Turkey, who launched Dolce Vento in 2025. The superyacht has a volume of 160 GT, has a steel hull and a steel superstructure.https://t.co/FqFaN1nLIt pic.twitter.com/synkRUC07j

— Claudia Lozano ⚓ (@clokslozano) September 4, 2025

So far, no cause has been officially determined, but Boat International reports that an investigation has been opened, and local outlets are blaming a “stabilization issue.”

Local reports also said the captain and two crew members swam to shore without injury.

Related: These Luxury Boats Are Owned By Some of the Wealthiest People in Tech and Include Swimming Pools and Basketball Courts

For entrepreneurs and business leaders, the challenge isn’t finding valuable books—it’s finding time to read them. Between back-to-back meetings, managing a team, and keeping an eye on the market, even carving out an hour a day can feel like a luxury. But knowledge doesn’t have to wait for the rare moments when you have a free weekend.

The 12min Micro Book Library trims bestselling titles down to concise, actionable insights that can be read or listened to in about 12 minutes. With lifetime access, you’ll tap into 1,800+ titles across 24 categories and get 30 new additions every month, all designed to keep you learning without slowing down your schedule.

Imagine digesting the core ideas of The 7 Habits of Highly Effective People before your morning coffee or listening to The Subtle Art of Not Giving a F*ck on your commute. Instead of skimming or abandoning books halfway through, you’ll walk away with the key lessons—ready to apply them to your business, career, or personal goals.

The library supports English, Spanish, and Portuguese, works offline, and even syncs with your Kindle. That means whether you’re flying to meet investors, taking a break between calls, or catching up on strategy while commuting, your personal book vault travels with you.

For leaders who believe continuous learning is part of staying competitive, this is one of the most efficient ways to keep your edge sharp—without adding another subscription or calendar block to your day.

Get lifetime access to the 12min Micro Book Library for just $39.99 (MSRP: $399.90) while it’s still on sale.

12min Micro Book Library: Lifetime Premium Subscription

See Deal

StackSocial prices subject to change.

Running a business today means efficiency matters more than ever. Between client emails, financial spreadsheets, and polished presentations, having the right tools on your desktop can make or break productivity. That’s why having the most modern software to support you is key.

Microsoft Office 2024 Home & Business is the latest, tech-forward iteration of the widely used Office suite. It’s also currently on sale for just $169.97 (MSRP: $249.99) for either Mac or PC.

Unlike subscription-based alternatives, this one-time purchase gives you permanent access to Word, Excel, PowerPoint, Outlook, and OneNote—the backbone apps businesses rely on daily. The 2024 release is more than just familiar icons: it introduces AI-powered suggestions, improved Excel data insights, enhanced PowerPoint storytelling tools, and a modernized Fluent Design interface that looks and feels streamlined across every device.

For business leaders, the collaboration features stand out. Co-authoring lets teams edit in real time, Outlook has improved accessibility checks to ensure communications remain professional, and PowerPoint now supports full voice and video recording — ideal for remote pitches or client updates. Excel’s AI-driven analysis also helps entrepreneurs spot trends and make faster, more informed decisions.

Another key advantage is security. Office 2024 strengthens protection against malicious add-ins, while Outlook makes email safety and organization easier to manage at scale. And because this is a lifetime license tied to your Microsoft account, there’s no recurring cost, no surprise renewals—just dependable productivity software for the long haul.

For business owners looking to upgrade their workflow without adding another monthly subscription to the books, this Office 2024 lifetime deal is a straightforward win.

Pick up a lifetime Office 2024 Home & Business license while it’s just $169.97 (MSRP: $249.99) for a limited time.

Microsoft Office 2024 Home & Business for Mac or PC Lifetime License

See Deal

StackSocial prices subject to change.