I Own a Professional Rugby Team — Here Are the 5 Biggest Lessons It’s Taught Me About Business Leadership

Opinions expressed by Entrepreneur contributors are their own.

When I signed on as a founding owner of the Houston SaberCats, people asked me the same question over and over: “Why rugby?”

To be fair, it wasn’t the obvious move. I’d already built a successful career in commodities trading and entrepreneurship. Rugby wasn’t a mainstream sport in the U.S., and it was clear we’d be climbing uphill in search for new market, new fans and new infrastructure. But that’s exactly what drew me to it.

Entrepreneurs know that if you only play safe games, you’ll never learn anything new. Rugby, in all its rawness, became a mirror for my business endeavors: tough, unpredictable and full of lessons that reshaped how I lead. Here are the five biggest ones.

Related: Adopt The Winning Habits of Elite Sports Stars to Unlock Entrepreneurial Greatness

1. Play through the hit

I’ll never forget standing on the sideline of our first SaberCats match, watching one of our players get leveled by a brutal tackle. Most people would’ve stayed down. He didn’t. He fought for every inch, rolled and kept driving the ball forward. The crowd erupted.

That image stuck with me. In rugby, getting hit is part of the game, and when you get hit, you don’t stop — you adapt mid-impact. In business, the “hit” looks like a failed deal, a regulatory curveball or a market downturn. I’ve had plenty of those. What separates winning leaders from the rest isn’t avoiding the hit; it’s what they do after. Push forward. Stay on your feet. Make the play anyway.

2. Trust the pack

Early on, I thought entrepreneurship was about individual brilliance, where the best idea, the hardest worker and the guy willing to put in more hours than anyone else wins. Rugby shattered that illusion.

A scrum is pure trust. Eight players lock in, shoulder to shoulder, with one mission: Move forward. If even one man falters, the whole formation collapses. It’s messy, it’s physical, and it’s all-or-nothing.

That’s exactly what business teams should look like. At GETCHOICE!, I’ve learned that success isn’t about me making every call. It is about surrounding myself with the right people, trusting them to do their jobs and creating a culture where loyalty and accountability are non-negotiable. No pack, no progress.

3. Adapt on the fly

Rugby is chaos. There are no endless timeouts to plan your next move. Plays evolve in seconds, and players must read the field, adjust and execute in real time.

I’ve had moments in business where a deal collapsed overnight or new regulations flipped our strategy upside down. The instinct is to freeze, but rugby trained me to do the opposite: Call an audible, pivot, and move. You may not always have perfect data, but you always have instinct and courage. And sometimes, that’s all you need to keep momentum alive.

4. Respect the grind

Here’s what most people don’t realize about rugby: These athletes play with no pads, no helmets and no glamour. It’s 80 minutes of collisions, sweat and bruises. And yet they do it because they love the grind.

That mentality is the same in entrepreneurship. When people see an acquisition announcement or a headline about success, they don’t see the years of grueling work behind it. The 4 a.m. flights. The contracts that fell apart. The stress of payroll weeks. Rugby reminded me that toughness isn’t a one-time choice but rather it’s a way of life. You have to enjoy the grind, because that’s what forges winners.

Related: Adopting an Elite Sports Mentality to Entrepreneurship

5. Leave it all on the field

Rugby has this tradition I fell in love with: After the final whistle, rivals share beers. Think about that — you spend 80 minutes hitting each other with everything you’ve got, and then you sit down together with mutual respect.

I’ve carried that same mindset into business. Compete fiercely, play full out, but respect your rivals. Shake hands. Learn from them. Because the legacy you leave isn’t about a single game or deal — it’s about how you show up, how you compete and the way people remember you when the whistle blows.

Rugby is the ultimate underdog game: tough, unpolished, but rich with lessons about teamwork, grit and respect. It changed how I lead, how I compete, and how I build companies.

And here’s the truth: Business, like rugby, isn’t for the faint of heart. You will get hit. You will get tested. But if you trust your pack, adapt when the field shifts and respect the grind, you’ll not just play the game, you’ll own it.

When I signed on as a founding owner of the Houston SaberCats, people asked me the same question over and over: “Why rugby?”

To be fair, it wasn’t the obvious move. I’d already built a successful career in commodities trading and entrepreneurship. Rugby wasn’t a mainstream sport in the U.S., and it was clear we’d be climbing uphill in search for new market, new fans and new infrastructure. But that’s exactly what drew me to it.

Entrepreneurs know that if you only play safe games, you’ll never learn anything new. Rugby, in all its rawness, became a mirror for my business endeavors: tough, unpredictable and full of lessons that reshaped how I lead. Here are the five biggest ones.

The rest of this article is locked.

Join Entrepreneur+ today for access.

https://www.entrepreneur.com/leadership/how-owning-a-professional-rugby-team-changed-the-way-i-lead/496147




Free Webinar | On-Demand: From Bottlenecks to Breakthroughs: 5 Barriers Stalling Entrepreneurs—and the System That Removes Them

Every founder eventually hits the same growth killers—isolation, decision fatigue, skill overload, stalled momentum, and a lack of real accountability. In this on-demand session you’ll see why these five barriers show up and why quick fixes rarely stick.

You’ll also be introduced to The Boardroom, Entrepreneur Media’s new six-month mastermind that pairs you with a hand-picked peer group and expert mentors who turn those obstacles into weekly breakthroughs.

Key takeaways:

  • Replace isolation with a curated advisory board

  • Slash decision fatigue using repeatable frameworks

  • Escape skill overload through expert playbooks

  • Restart stalled growth with high-leverage tactics

  • Close accountability gaps so goals become wins

Register now for instant access and start mapping your path from bottleneck to breakthrough.

Sign Up Now

About the Speakers:

Jason Feifer is the editor in chief of Entrepreneur magazine and host of the podcast Problem Solvers. Outside of Entrepreneur, he writes the newsletter One Thing Better, which each week gives you one better way to build a career or company you love. He is also a startup advisor, keynote speaker, book author, and nonstop optimism machine.

Jacqueline “JJ” Jasionowski blends luxury-brand rigor with entrepreneurial speed. After 17 years at BMW Group leading growth, training, and CX initiatives, she launched Shift Awake Group to deploy tech-forward training that lifts customer satisfaction and revenue. A Certified Professional Coach and expert facilitator, JJ builds behavior-shifting systems—reducing friction and driving measurable outcomes.

Every founder eventually hits the same growth killers—isolation, decision fatigue, skill overload, stalled momentum, and a lack of real accountability. In this on-demand session you’ll see why these five barriers show up and why quick fixes rarely stick.

You’ll also be introduced to The Boardroom, Entrepreneur Media’s new six-month mastermind that pairs you with a hand-picked peer group and expert mentors who turn those obstacles into weekly breakthroughs.

Key takeaways:

The rest of this article is locked.

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https://www.entrepreneur.com/starting-a-business/free-webinar-on-demand-from-bottlenecks-to/496744




He Was Working a Desk Job at a ‘Big Four’ Accounting Firm 3 Years Ago. Now He’s Pitching in Major League Baseball.

Nick Raquet’s LinkedIn now says he’s a “Professional Baseball Player with the St. Louis Cardinals.” But just a couple of years ago, he was a consultant at the “Big Four” firm, Ernst & Young (EY).

When Covid hit in 2020, Raquet, now 29, was a minor leaguer who hadn’t advanced past single-A (the lowest tier) ball. He decided to hang up his cleats and use his finance degree from the College of William & Mary to try his hand at a 9-to-5 in corporate America, per MLB.com.

For a little over a year in 2021-2022, Raquet was an “entry-level consultant on the Enterprise Risk team” at EY, where he “supported clients in identifying and managing risks to their business operations and objectives,” according to his LinkedIn.

Related: ‘Big Four’ Salaries: How Much Accountants and Consultants Make at Deloitte, PwC, KPMG, and EY

Nick Raquet #70 of the St. Louis Cardinals looks on during the game between the St. Louis Cardinals and the Seattle Mariners at T-Mobile Park on Monday, September 8, 2025, in Seattle, Washington.

It was short-lived.

MLB.com reports that after about a year, Raquet was not feeling “fulfilled” and decided to go back to the sport he loved. He joined an independent league team and began the grind once again, this time with a new attitude. He was just happy to be there.

A few years later, on Monday, he made his MLB pitching debut. (The Cardinals lost, but he earned a strikeout.)

Although Raquet may be quitting accounting forever, the skills he learned at EY (identifying challenges, implementing risk management processes, analyzing data, and participating in various training sessions, per his LinkedIn) will certainly come in handy in baseball, too.

Related: The Power of Thought in Shaping Your Success — How Mindset Drives Your Circumstances

Nick Raquet’s LinkedIn now says he’s a “Professional Baseball Player with the St. Louis Cardinals.” But just a couple of years ago, he was a consultant at the “Big Four” firm, Ernst & Young (EY).

When Covid hit in 2020, Raquet, now 29, was a minor leaguer who hadn’t advanced past single-A (the lowest tier) ball. He decided to hang up his cleats and use his finance degree from the College of William & Mary to try his hand at a 9-to-5 in corporate America, per MLB.com.

For a little over a year in 2021-2022, Raquet was an “entry-level consultant on the Enterprise Risk team” at EY, where he “supported clients in identifying and managing risks to their business operations and objectives,” according to his LinkedIn.

The rest of this article is locked.

Join Entrepreneur+ today for access.

https://www.entrepreneur.com/business-news/nick-raquet-from-big-four-firm-to-mlbs-big-league/496959




‘Most Powerful Yet’: Apple Just Revealed the iPhone 17, iPhone Air, and AirPods With Live Translation. Here’s What to Know.

Apple held its biggest launch event of the year on Tuesday, with the tagline: “Awe Dropping.” At the event, Apple released the next generation of iPhones, Apple Watches, and AirPods, including the Apple Watch Ultra 3, AirPods Pro 3, and iPhone 17.

“We’re taking the biggest leap ever for iPhone,” Apple CEO Tim Cook said at the event.

Here’s what Apple announced, from the ultra-thin profile of the iPhone Air to satellite connectivity on the Apple Watch Ultra 3.

Related: ‘We’re Very Open’: Apple CEO Tim Cook Says He Wants to Buy Startups. Could Your Company Be Next?

Apple Introduced the iPhone Air and iPhone 17

The new iPhone lineup includes four new phones: the iPhone Air, 17, 17 Pro, and 17 Pro Max.

Apple revealed its highly anticipated $999 iPhone Air, the “thinnest iPhone ever” — at 5.6 millimeters, it’s the slimmest iPhone yet. Apple also claims that the 6.5-inch phone is the most durable of all iPhones and benefits from an improved internal chip. It’s the most power-efficient iPhone ever made, with a powerful camera and an all-day battery life.

iPhone Air. Credit: Apple

Meanwhile, the $1,099 iPhone 17 Pro is “the most powerful iPhone yet, by far,” according to Apple. The phone has a unified outer body that uniformly dissipates heat from the battery, preventing overheating. Apple also said that the phone offers “the best battery life ever in an iPhone,” with 39 hours of video playback.

Related: How Much Does Apple Pay Its Employees? Here Are the Exact Salaries of Staff Jobs, Including Developers, Engineers, and Consultants.

Apple said the event was filmed with an iPhone 17 Pro, demonstrating the capabilities of the phone in real time. The $1,199 iPhone 17 Pro Max has a larger screen than the Pro, but features the same capabilities, including increased power and battery life.

iPhone 17 Pro. Credit: Apple

The standard iPhone 17 features a 6.3-inch display with thinner borders for a wider screen. The display is more readable in direct sunlight, and the phone has twice the scratch resistance. Charging is now faster than ever: Ten minutes of charge can result in 8 hours of video playback.

iPhone cameras are also improving, with better resolution and a wide field of view for the front-facing camera. Apple noted that users took 500 billion selfies last year, more than any other smartphone.

iPhone 17. Credit: Apple

Pre-orders for the new iPhone lineup start Sept. 12. The new phones will be available starting Sept. 19.

What’s New With the AirPods Pro 3

Cook said that this year, Apple was building on innovations with AirPods Pro, including the hearing aid function introduced last year that transformed the buds into assistive devices for people experiencing mild to moderate hearing loss.

Related: Your Old Apple AirPods Can Soon Act as an Over-the-Counter Hearing Aid, According to the FDA

At the event, Julz Arney, senior director of fitness technologies at Apple, introduced heart rate sensing for AirPods. Custom sensors on the AirPods allow the earbuds to track heart rate independently of a smartwatch, Arney explained.

AirPods Pro 3. Credit: Apple

The AirPods Pro 3 also deliver twice the active noise cancellation of previous generations. Apple claimed that the AirPods deliver the world’s best active noise cancellation of any in-ear headphones.

The earbuds also offer live translation, transforming words from one language into another in real-time. For example, if someone speaks a different language, the AirPods will lower their voice and deliver a real-time translation.

The AirPods Pro 3 cost $249 and will be available on Sept. 19. Preorders begin Tuesday.

Here’s How the Apple Watch Is Changing

Apple introduced the $399 Apple Watch Series 11, which comes with a thorough list of health features, including state-of-mind tracking for mental health.

In a new development, Apple is taking on hypertension, or high blood pressure, with a new feature that tracks irregularities in blood pressure over time. Apple expects to notify one million people of hypertension within the first year alone.

Apple Watch Series 11. Credit: Apple

The company is also introducing a new sleep score based on duration of sleep, how many times a user wakes up throughout the night, and regularity of sleep over time. The new sleep score function applies to the budget-friendly $249 Apple Watch SE 3.

The $799 Apple Watch Ultra 3 is also packed with new features, including satellite connectivity. Even when a user is off the grid, they can use their Apple Watch to get help in case of an emergency. The watch features 42 hours of battery life and also has hypertension notifications.

Apple Watch Ultra 3. Credit: Apple

Cook called Apple Watch “the most popular watch in the world.”

The Apple Watches can be pre-ordered today and will be available starting Sept. 19.

Apple held its biggest launch event of the year on Tuesday, with the tagline: “Awe Dropping.” At the event, Apple released the next generation of iPhones, Apple Watches, and AirPods, including the Apple Watch Ultra 3, AirPods Pro 3, and iPhone 17.

“We’re taking the biggest leap ever for iPhone,” Apple CEO Tim Cook said at the event.

Here’s what Apple announced, from the ultra-thin profile of the iPhone Air to satellite connectivity on the Apple Watch Ultra 3.

The rest of this article is locked.

Join Entrepreneur+ today for access.

https://www.entrepreneur.com/business-news/apple-reveals-iphone-17-iphone-air-airpods-apple-watch/496915




Email Isn’t Dead — But Your Strategy Might Be. Here’s How to Revive It

Opinions expressed by Entrepreneur contributors are their own.

Let’s address the elephant in the inbox.

Email marketing isn’t dead. It’s not outdated. It hasn’t been replaced by TikTok, Threads or an army of AI bots. In fact, email is still one of the most reliable, highest-ROI marketing channels in your arsenal — if you actually use it right.

But here’s the inconvenient truth: most businesses don’t. They treat email like a leftover tactic from 2009, not the strategic revenue engine it can be. So when their campaigns fail, the blame is often directed at the platform, the audience, the open rates — everything except the real culprit: a broken system.

I’ve had enough client calls that start the same way to spot the pattern. “We’ve been sending emails for years,” they say. “Newsletters, sales promos, special offers. But it’s just not working anymore.”

Spoiler: The problem isn’t email. It’s execution. Let’s break it down.

Stop sending and hoping

Before you send another message, ask yourself one question: What is the actual goal of this email? If your answer is “generate leads,” great. That’s a start. But leads don’t materialize just because you hit send. Email isn’t magic. It’s a relationship channel.

You need a strategy. Are you building relevance? Segmenting based on interest? Optimizing timing? Tracking behavior across your site and CRM? If not, you’re not doing email marketing. You’re just sending digital flyers and hoping someone notices.

Related: 12 Reasons Why Your Emails Aren’t Driving Business

Your list isn’t a strategy

Here’s the harsh reality: most email lists are digital junk drawers. Bloated, unsegmented and outdated.

One client had 25,000 contacts in a single list labeled “Newsletter.” No segmentation. No tagging. Just one-size-fits-all messaging to cold leads, VIP clients and long-lost contacts alike. Their click-through rate? Less than 1%.

Would you hand the same sales pitch to a returning customer, a cold prospect and a lapsed buyer? Then why are you emailing them like they’re all the same person?

Your email platform has segmentation tools for a reason. Use them. Tag based on behavior, purchase history, content engagement and lifecycle stage. And if your list is outdated? Run a re-engagement campaign. Let people self-select. And yes — let them unsubscribe. Because a clean, active list will always outperform a bloated one.

Your platform might be failing you

If you’re still using the free version of Mailchimp from 2017, expecting results is like entering a Formula 1 race on a tricycle.

Email platforms have evolved. If yours doesn’t offer automation, A/B testing, tagging, CRM integration or real-time analytics, it’s holding you back. For ecommerce, I recommend Klaviyo. It connects directly to Shopify, lets you recover abandoned carts, trigger smart automations and — this is key — track actual sales tied to email behavior.

And yes, you’ll need to invest in a platform that can handle more than “send newsletter.” If you’re serious about revenue, stop being cheap about the tool that drives it.

Stop worshiping the open rate

Everyone obsesses over open rates like they’re gospel. But here’s the truth: a high open rate doesn’t mean anything if no one clicks, converts or remembers you. Don’t just design pretty emails. Design strategic ones.

Ask better questions. What KPIs actually map to your business goals? For ecommerce, it might be revenue per email, cart recovery rate or product clicks. For B2B, it may be meetings booked or resources downloaded.

Start there. Reverse-engineer your content. Then test relentlessly. Subject lines. Send times. CTA placement. Message framing. Real marketers test. Lazy marketers send and pray.

Visibility, credibility, engagement — then sales

Email doesn’t operate in a vacuum. It’s part of a journey. You don’t go from “nice to meet you” to “here’s our invoice” overnight. So layer your content.

Visibility gets you seen.
Credibility makes you trusted.
Engagement builds the bridge.
Sales walk across it.

If every email is just a promotion, you’re not building a bridge — you’re shouting into the void. Offer value. Share insight. Deliver relevance. And when it’s time to sell, you won’t have to beg for attention. You’ll already have it.

Related: 6 Reasons Your Marketing Emails Aren’t Converting — and How to Fix Them All

Campaigns don’t build revenue — systems do

Most marketers jump straight to tactics — “Let’s send something Tuesday at 10 a.m.” — with no infrastructure underneath.

But if your email doesn’t plug into a system, it’s a short-term stunt, not a long-term strategy.

Here’s what a real email system looks like:

  • Set up automated workflows for key stages like onboarding, re-engagement and post-purchase to nurture your audience over time.
  • Build segmented customer journeys that align with specific buyer behaviors so your emails are always relevant and timely.
  • Integrate your email platform with your CRM and ecommerce systems to enable real-time targeting based on user actions.
  • Define clear KPIs that are directly tied to business outcomes before you create or send any campaigns.

This is the work most marketers skip. And it’s why their email marketing never scales. Strategy always beats volume.

Want to win Q4? Fix this in Q3

Here’s your reality check: once fall hits, you’re out of time. Black Friday. Cyber Monday. Holiday chaos. End-of-year goals. Your calendar will be execution-heavy and strategy-starved.

So fix it now.

Audit your platform. Clean your list. Segment your contacts. Define your goals. Connect your data. Build the machine. Because when email works, it doesn’t just deliver opens. It delivers ROI. Recurring revenue. Customer loyalty. And a real reason to celebrate when the quarter ends.

Let’s address the elephant in the inbox.

Email marketing isn’t dead. It’s not outdated. It hasn’t been replaced by TikTok, Threads or an army of AI bots. In fact, email is still one of the most reliable, highest-ROI marketing channels in your arsenal — if you actually use it right.

But here’s the inconvenient truth: most businesses don’t. They treat email like a leftover tactic from 2009, not the strategic revenue engine it can be. So when their campaigns fail, the blame is often directed at the platform, the audience, the open rates — everything except the real culprit: a broken system.

The rest of this article is locked.

Join Entrepreneur+ today for access.

https://www.entrepreneur.com/growing-a-business/email-isnt-dead-but-your-strategy-might-be-heres-how/495132




Microsoft’s Return-to-Office Mandate Will Begin in a Few Months. Here’s What We Know.

In August, it was reported that Microsoft was planning to mandate its employees back to the office “at least” three days a week as soon as January 2026. (Employees currently can work remotely “half” of the workweek.)

Now, according to an internal email sent to Microsoft staff on Tuesday, the company has finalized its plans and is issuing a return-to-office (RTO) mandate in three phases, beginning at the end of February 2026, according to Business Insider.

“In the AI era, we are moving faster than ever, building world-class technology that changes how people live and work, and how organizations everywhere operate,” reads the email from Microsoft HR chief Amy Coleman. “If you reflect on our history, the most meaningful breakthroughs happen when we build on each other’s ideas together, in real time.”

Related: Microsoft Just Became the Second Company in History to Achieve a $4 Trillion Valuation — Here’s How

As of June 30, Microsoft employed 228,000 workers, with 125,000 located in the U.S.

According to the email, the first phase will focus on employees who live in the Puget Sound, Washington area, and will begin around February 23. “If you live within 50 miles of a Microsoft office, you’ll be expected to work onsite three days a week starting [at the end of February],” the email reads.

A general view of the Microsoft Zizhu Campus in Minghang, Shanghai, China, on June 30, 2025. International employees will learn more about their RTO in 2026. Ying Tang/NurPhoto via Getty Images

The RTO mandate will then expand to other offices in the U.S. and, eventually, internationally, for which planning will begin in 2026, according to the email.

Related: Amazon Tells Thousands of Employees to Relocate or Resign

The memo said that the rest of the staff will hear from their “EVP or organizational leadership today with specific guidance,” the email reads. “If you are outside of the Puget Sound area, you do not need to take any action at this time unless your EVP communicates otherwise.”

“We’ve looked at how our teams work best, and the data is clear: when people work together in person more often, they thrive—they are more energized, empowered, and they deliver stronger results,” Coleman wrote.

Related: Microsoft’s CEO Says the Company’s Mass Layoffs, Despite Financial Success, Are ‘Weighing Heavily on Me’ in an Internal Memo

In August, it was reported that Microsoft was planning to mandate its employees back to the office “at least” three days a week as soon as January 2026. (Employees currently can work remotely “half” of the workweek.)

Now, according to an internal email sent to Microsoft staff on Tuesday, the company has finalized its plans and is issuing a return-to-office (RTO) mandate in three phases, beginning at the end of February 2026, according to Business Insider.

“In the AI era, we are moving faster than ever, building world-class technology that changes how people live and work, and how organizations everywhere operate,” reads the email from Microsoft HR chief Amy Coleman. “If you reflect on our history, the most meaningful breakthroughs happen when we build on each other’s ideas together, in real time.”

The rest of this article is locked.

Join Entrepreneur+ today for access.

https://www.entrepreneur.com/business-news/microsoft-rto-mandate-to-begin-in-february-2026/496912




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’

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.

https://www.entrepreneur.com/starting-a-business/moms-creative-side-hustle-grew-to-570000-a-month-penny/496484




10 Underrated Podcasts Every Entrepreneur Should Be Listening To

Opinions expressed by Entrepreneur contributors are their own.

As entrepreneurs, we’re constantly bombarded with recommendations for the same big-name podcasts (How I Built This, The Tim Ferriss Show or Masters of Scale). They’re good, but they’ve become the mainstream playlists of the entrepreneurial world. The real edge comes from discovering voices that are flying under the radar — podcasts that don’t just regurgitate clichés but dig into gritty lessons, unconventional strategies and the realities most entrepreneurs are too busy or too cautious to discuss openly.

As a venture investor and CEO, I’ve seen firsthand that the entrepreneurs who win are the ones who think differently, seek perspectives outside the obvious, and leverage wisdom from unexpected places. These podcasts won’t necessarily appear in your LinkedIn feed, but they’ll challenge your thinking and, more importantly, give you the kind of insights your competition probably hasn’t heard yet.

Here are 10 underrated podcasts that deserve a permanent spot in your queue.

Related: The 10 Best Podcasts Every Entrepreneur Should Listen to for Growth, Strategy and Success

1. The Indie Biz Podcast

This show focuses on small, independent businesses — the kind that bootstrap from scratch without Silicon Valley backing. The episodes highlight founders who navigate obstacles with resourcefulness rather than venture capital. For entrepreneurs, it’s a refreshing reminder that success isn’t about billion-dollar valuations but about building sustainable, real businesses.

Takeaway: Learn how scrappiness and creativity often matter more than scale.

2. Bootstrap Stories

This podcast dives into entrepreneurs who took the long road — growing without outside investment. It’s raw, honest and humbling. Founders share what it’s like to sacrifice personal comfort for business growth and how they resisted the temptation to chase capital too early.

Takeaway: Discipline in growth and ownership has its advantages. You control your destiny.

3. Creative Elements

Host Jay Clouse interviews creators and solopreneurs making a living on their own terms. It’s not just about business mechanics; it’s about the psychology of creativity, discipline and building personal brands. If your work involves content, media or personal branding, this podcast is pure gold.

Takeaway: Entrepreneurs are creators too, and learning from the creative economy can sharpen your edge.

4. The Unmistakable Creative

Unlike formulaic business shows, this podcast dives deep into the unusual and unexpected. It’s less about business tactics and more about perspective — bringing in artists, scientists, and thinkers whose insights cross-pollinate with entrepreneurship in surprising ways.

Takeaway: Great business breakthroughs often come from outside the business world.

5. StartUp Therapy

Two founders (Wil Schroter and Ryan Rutan) talk candidly about the mental and emotional battles entrepreneurs face. From burnout to imposter syndrome to co-founder conflicts, it’s a brutally honest discussion that feels more like a therapy session than a business seminar.

Takeaway: Entrepreneurship isn’t just about strategy; it’s about managing your mind and emotions.

Related: 25 Top Podcasts That Will Spark Your Entrepreneurial Vision

6. The Sweaty Startup

Nick Huber focuses on “uncool” businesses — self-storage, property management, cleaning services — that generate massive wealth. It’s a counterbalance to the obsession with tech startups, reminding us that riches are often made in industries no one brags about at cocktail parties.

Takeaway: Don’t overlook “boring” businesses — they’re often the most profitable.

7. The Exit

This show spotlights founders who’ve sold their companies, breaking down the process of negotiations, valuation and exit strategy. It’s tactical and strategic, and it teaches entrepreneurs to think with the end in mind, even when they’re just starting.

Takeaway: Building with an exit in mind shapes smarter decisions from day one.

8. Business Wars

More of a storytelling show than a tactical one, Business Wars dramatizes rivalries between iconic companies — Nike vs. Adidas, Netflix vs. Blockbuster, Uber vs. Lyft. For entrepreneurs, these stories reveal how strategy, timing and ego shape industries.

Takeaway: Learn from history. Understanding how giants fought their wars can prepare you for your own battles.

9. The Twenty Minute VC

Harry Stebbings interviews top investors and founders, but it’s not a polished PR tour. The conversations are direct and filled with behind-the-scenes insights about what investors actually look for and what separates good pitches from bad ones.

Takeaway: If raising money is on your roadmap, this show gives you a rare peek inside the investor’s head.

10. My First Million

While not completely “underrated,” it still flies under the mainstream radar compared to the giants. The hosts brainstorm business ideas, dissect companies and share unconventional strategies for building wealth. It’s fast, funny and refreshingly irreverent.

Takeaway: Business ideation is a skill — you get sharper at spotting opportunities by listening to others riff.

Related: 30 Top Podcasts for Influential Entrepreneurs

Why these podcasts matter

What sets these podcasts apart isn’t just that they’re less well-known; it’s that they expose you to perspectives and strategies outside the typical entrepreneur echo chamber. Mainstream shows often polish their stories for mass appeal, but these conversations are raw, unfiltered and unapologetically real.

They remind us that entrepreneurship isn’t a highlight reel — it’s the grind, the doubt, the breakthroughs and the failures that lead to transformation.

If you’re serious about growth, carve out time to listen. Put one of these podcasts into your rotation each week. Don’t just listen passively. Take notes, share with your team, and apply the insights to your business.

Because in a world where everyone is consuming the same mainstream content, the real advantage comes from tuning into voices your competitors aren’t even aware of yet.

As entrepreneurs, we’re constantly bombarded with recommendations for the same big-name podcasts (How I Built This, The Tim Ferriss Show or Masters of Scale). They’re good, but they’ve become the mainstream playlists of the entrepreneurial world. The real edge comes from discovering voices that are flying under the radar — podcasts that don’t just regurgitate clichés but dig into gritty lessons, unconventional strategies and the realities most entrepreneurs are too busy or too cautious to discuss openly.

As a venture investor and CEO, I’ve seen firsthand that the entrepreneurs who win are the ones who think differently, seek perspectives outside the obvious, and leverage wisdom from unexpected places. These podcasts won’t necessarily appear in your LinkedIn feed, but they’ll challenge your thinking and, more importantly, give you the kind of insights your competition probably hasn’t heard yet.

Here are 10 underrated podcasts that deserve a permanent spot in your queue.

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https://www.entrepreneur.com/leadership/10-underrated-podcasts-every-entrepreneur-should-listen-to/496160




I Built a Strong Company That Operates Without Me — These Are 8 Ways I Accelerated Team Trust

Opinions expressed by Entrepreneur contributors are their own.

Entrepreneurship is a hard road. There’s no rule book, and as a business owner, it can feel like you’re always on call.

Each summer, before my children start school again, I put that life on pause. We load up our RV and head out for a multi-week trip. I don’t invite distraction during this time: in fact, my team knows that I’m off limits. This time is for me, my family and our relationships.

Building a culture that can persist when I’m not in the office is crucial — not only to the success of my business but for my personal life. Creating culture takes intention, but the payoff is worth it. I won’t spend my waning days on vacation worrying about what I’m stepping back into.

I know. That’s because I work to decentralize myself from my business.

Not just short-term gains

Decentralizing yourself from your business isn’t just about the short-term gain of getting to go away on vacation or finding time to incorporate personal passions into your life outside of your business.

It’s about building a significant company.

Significant companies are ready to transition at any point. To have value in the eyes of a buyer, my business can’t just be about me.

That’s not to say that my mark isn’t on the business. Far from it. I put the work in on the front end with my executive team to craft eight “trust accelerators” that allow for clarity, alignment and informed decision-making.

Related: Lack of Trust—What Does It Do to Your Company? Here’s What Leaders Need to Know

Beyond core values

Almost every company has core values. We have them, too. But, right about the time that the COVID-19 pandemic hit, we all noticed that they weren’t working. While core values are general north stars for any organization, sometimes they can feel like they’re a galaxy away from the day-to-day issues that every person in a business must take accountability for.

What makes us unique is our trust accelerators, which are married to our core values. More than just guiding principles that we put on a wall, trust accelerators are active rules that we follow interaction to interaction.

In fact, we don’t put these on a wall somewhere in our waiting room: each trust accelerator is printed on a card that each member of our team carries with them.

Your culture is yours alone. These are the trust accelerators that we live by:

1. No meetings after the meeting

How we live it: If everyone is in a room to make a decision or discuss an initiative, they’re there by design. It’s inauthentic to invite input and then have two executives go into a room to debrief and make the real decision.

If a member of our team has something to contribute, we want them to do it in the room where the actual decisions are being made.

How it builds value: If people work at a place where they have obvious input into real decisions, they take more accountability for their contributions.

2. Put yourself in other people’s position

How we live it: We’re not just interested in the “how” of people’s actions; we’re interested in the “why.” After all, they may have good reasons that unlock clues about how we should operate. By seeking understanding, we build connection.

How it builds value: Empathy is a critical skill — not just for connecting with colleagues but for connecting with customers.

Related: 5 Foolproof Strategies to Help You Let Go and Trust Your Team

3. Listen while avoiding judgment

How we live it: My business, Exit Planning Institute, focuses on educating, credentialing and empowering Certified Exit Planning Advisors as they guide business owners through value creation and successful exits. While advisors have witnessed the factors that contribute to an owner’s success, every owner’s journey is unique — and there are many ways to build a significant company. Only through listening can we understand each other’s motivations and values, and embrace perspectives that might be counter to our own.

How it builds value: If a conversation is necessary, it deserves to be full-throated. That’s only possible with a listener who is willing to be curious, not judgmental.

4. 100% preparedness and participation

How we live it: Collaboration is crucial to an empowered workforce that can function without its leader. Our culture runs on every person showing up prepared and participating.

How it builds value: Every member of our team knows that they were selected for a reason. They can’t reach their full potential unless they are ready to contribute — and actually do.

5. Deliver the mail to the right address

How we live it: If we have an issue — or reason to praise someone — we don’t go to a trusted colleague or a supervisor. We go right to the correct address: the person we want to discuss with. It allows for more authentic communication — see “Listen While Avoiding Judgement” — and limits gossip, an incredible culture-killer.

How it builds value: Every member of our team knows they’re accountable to every other member—and our doors are open to have a conversation with each other.

6. Honesty without repercussion

How we live it: We’re not at work to be well-liked or adulated (although that happens sometimes, too!). We’re at work to advance our business. By cultivating an atmosphere of respectful honesty, we get to offer our insights and listen to how others might do things differently.

How it builds value: When every person on the team feels like they can contribute, we see how they might grow into their careers at the company — in the short- and long-term.

7. Respectful

How we live it: We’re bound not to see eye to eye. However, these trust accelerators do a lot of work to help us understand that we’re all working towards the same goals. When we put respect first in every interaction we have with each other, it reinforces that our differences aren’t personal — and can sometimes be assets to our business goals.

How it builds value: We can’t tackle the hard stuff until we see each other as humans. If everyone knows that their perspective is respected, we tap into each other’s skills.

8. Confidentiality

How we live it: We have to move past surface-level conversations if we’re going to be a significant company. We’re not shooting for good. We’re going for best-in-class. That requires trust—and in this case, trust that if something is shared confidentially, it stays confidential.

How it builds value: When we have deep trust, we believe that our colleagues—the ones we depend on to bring our goals to life—will do everything they can do to help us all achieve something great.

Related: 7 Proven Tips for Building Trust and Strengthening Workplace Relationships

Empowering your leaders

It isn’t easy to be an owner and not be in total control. However, there’s a multiplier effect that comes with empowering your employees and building trust across the organization. To build a culture where every person feels a sense of ownership, there must be two-way trust: employees feel trusted, and leaders actually trust the people they work with. Additionally, as I empower our leaders to build a culture where they are trusted to make informed, quick decisions, I’m also sure to:

  1. Train the executive team on my long-term vision.
  2. Be transparent about our profits/losses, our operations and even my salary. It takes a great deal of time to educate the leadership team, but it enables them to know the short-term impact of every decision.
  3. Over-communicate. I’m shocked by how many owners don’t communicate with their leadership team. They can’t make decisions that I’d ultimately agree with if they don’t know what I’m thinking.

Related: How to Close the Trust Gap Between You and Your Team—5 Strategies for Leaders

Building a culture of trust is something I think about every day, and not just because I know that culture will ultimately pay off with a more successful exit.

Culture also comes easily to me — it’s what I like to spend time on.

If you don’t, you can still build culture. Finding a Certified Exit Planning Advisor who specializes in company culture can help you start building human capital at your company.

https://www.entrepreneur.com/starting-a-business/8-ways-to-build-a-business-that-can-run-without-you/496481




Here’s How Barbara Corcoran Turned a Huge ‘Flop’ Into Pioneering Real Estate Technology

Many entrepreneurs have a deal they probably wish they didn’t make, or, perhaps worse, one that got away. And real estate pioneer and longtime “Shark Tank” investor Barbara Corcoran remembers hers clearly. She told her Instagram followers on Monday that she invested her first major profit into a “genius” idea that ended up being a total flop — and a bit ahead of its time.

“My greatest successes happened on the heels of failure,” Corcoran wrote. “The moment I made my first profit, it felt like all the long nights and rejection finally paid off. I wanted to invest it in something big that would set me apart.”

Related: How Nvidia CEO Jensen Huang Transformed a Graphics Card Company Into an AI Giant: ‘One of the Most Remarkable Business Pivots in History’

Corcoran says she “took every penny” she had, which was around $75,000 at the time, and made videotapes of all of her company’s real estate listings.

“I thought it was genius!” she said. “Buyers could pop in a tape and tour our apartments from the comfort of their La-Z-Boy chair.”

However, Corcoran didn’t anticipate her fellow real estate agents not wanting to hand out tapes with her face on it (and not their own). So, tens of thousands of dollars worth of VHS tapes went into boxes and “sat untouched” in storage.

“My brilliant idea was a total flop,” Corcoran said. “Just like that, my $75,000 was gone.”

But when the Internet went mainstream shortly after, she knew she was back in business.

Related: Barbara Corcoran Needed to Make Job Cuts. Here’s Why She Fired Her Mom First.

“I heard whispers about this brand new thing called ‘the Internet.’ Most people thought it was a joke,” Corcoran said. “I didn’t. I registered my company’s URL immediately, and I snagged my competitor’s, too. (That’s a story for another day.) Then, I remembered those dusty tapes.”

Corcoran says she took the boxes out of storage, uploaded the tapes to the website, and within a week had “two sales came in from London, site unseen.”

“The same idea that had failed miserably suddenly became my breakthrough,” Corcoran says. “The best successes often happen on the heels of failure.”

Moral of the story? Put your failures in a box out of sight, but don’t throw them away — you never know when they can be repurposed into success.

Related: ‘I Don’t Know How I Know This, But I Know This’: Learn This Psychic Medium’s Method for Trusting Your Intuition

https://www.entrepreneur.com/business-news/barbara-corcoran-how-i-turned-failure-into-monetary-success/496900