How to Survive a Million-Dollar Loss

This year I’ve sprinkled occasional “Ecommerce Conversations” episodes with real-life master classes from Beardbrand, my company. To date I’ve addressed hiring, branding, profit-building, priority-setting, and exiting.

For this installment, I’ll share Beardbrand’s experience of losing nearly $1 million across 2023 and 2024. I’ll recap how we managed to survive our worst years in business while remaining 100% bootstrapped.

It got bad. Our cash levels dropped to where they were in year one, 2014. We were hemorrhaging money.

But we’re still here — still building and still learning. We made it through without outside funding.

Here’s what the future holds for Beardbrand. My entire audio dialog is embedded below. The transcript is condensed and edited for clarity.

Ghosted

A big portion of our loss came from Target. The company had been a seven-figure account for us for years, and we thought the relationship was solid. Every year, we pitched Target our plans. Historically, the staff there provided us with clear feedback — what worked, what didn’t, and where there was room for growth.

In 2023, Target had a sustainability initiative. We revamped our packaging, switching from glass and plastic to aluminum. It’s lighter, more recyclable, and aligns with eco-conscious goals. At the same time, we increased the size of our beard oil packaging from 1 oz. bottles to occupy more shelf space and stand out.

We committed early, produced inventory, and delivered Target’s purchase orders on time. Then silence. Nothing. After years of working with us, the staff ghosted us. No feedback, no responses. Worse, they dropped us and left us with nearly $200,000 of unpaid product.

We erred by giving Target exclusivity, which meant we weren’t selling on Amazon or Walmart. That killed our ability to move leftover inventory quickly when they dropped us. By the time we finally got on Amazon, the products had already aged out. We destroyed a large quantity that had expired.

Reserves

We’ve always run Beardbrand conservatively. That means keeping a decent amount of capital in reserve — not because we’re paranoid, but because you never know when a black swan event might hit. Having that runway lets you make clear, intentional decisions rather than panicking. It gives you time to explore solutions, test channels, and get a better night’s sleep.

Thankfully, during our stronger years, we built up a solid cushion. And that cushion is what kept us afloat during the downturn. We essentially burned through all of it. But we never dipped below zero, which meant we didn’t have to take out high-interest loans, open lines of credit, or bring in outside investors.

We did have conversations just in case. I even considered withdrawing money from my personal savings. But that’s a hard decision when things aren’t going well. When you’re in the middle of the storm, it doesn’t feel like a temporary dip — it feels like a freefall. You start wondering: Is this the bottom, or is there more pain ahead?

Writing another personal check to the business, especially after years of building wealth from it, was not something I wanted to do. And neither did my partners. We were determined to find a way forward that didn’t involve doubling down with personal capital or giving up control.

Pileup

In addition to losing Target, we experienced a series of setbacks. First, the state of Texas audited us. We cooperated fully, waited for the final numbers, and instead got slapped with a tax lien. That lien triggered Brex, our corporate credit card provider, to freeze our account, despite our perfect payment history. Thankfully, American Express stood by us and kept things moving.

Then came an ADA lawsuit, a leaked 100% off coupon code, and a $20,000 air conditioner repair at our barbershop. We also faced regulatory changes that forced us to reformulate key fragrances.

We had internal missteps, such as losing a key growth team member and coasting when we should’ve pushed harder. We focused on profitability, but the business slowly declined.

We simplified our product line to meet a manufacturer’s needs, which, in hindsight, proved to be a mistake. The lesson? Partner with vendors who value your business. You don’t want to be too small to matter, or too big to be managed. That relationship needs to be just right.

We also lowered prices to drive volume, but it backfired. Loyal customers just paid less, and those who thought we were expensive still did. Meanwhile, larger packaging reduced purchase frequency, and killing off beloved fragrances hurt loyalty. Top-line revenue got cut in half.

Furthermore, when your business shrinks, fixed costs such as office leases and payroll can become overwhelming. Our $10,000 per month lease that once felt small became a big deal.

Rebuilding

The good news? Beardbrand is alive. We’ve weathered the storm and slowly started turning things around. It hasn’t been a dramatic rebound — it’s been steady, slow progress. We have focused on improving operations, addressing inventory issues, resolving stock-outs, tightening pricing, and enhancing product quality.

We now have the right fulfillment provider, manufacturing partners, and systems in place. Instead of existential crises, we’re dealing with everyday stuff — shipping issues, ad performance, and the occasional bad product batch. That’s a massive shift. It’s not glamorous, but it’s no longer a matter of survival.

We cut costs aggressively — even eliminating $15 per month software. We reestablished healthy margins. Our customer service, returns, and product quality all depend on having room to breathe financially.

The Target fallout is behind us, the tax lien is resolved, and the ADA plaintiff dropped the bogus lawsuit. My business partner stepped out of day-to-day operations, and some team members transitioned to part-time roles, which helped improve our cash flow. We’ve managed all of this without layoffs. My team is the same one that helped us grow, and they’re still incredibly talented and dedicated.

I’ve also cut my own salary and lived off personal savings to keep things afloat. But I’m optimistic. With the business stabilizing, we can rebuild our savings and start exploring new growth opportunities again.

Momentum

Survival mode means focusing on making it through the day. Some entrepreneurs try to grow their way out of problems. For us, it started with stabilizing operations. We can finally think long-term again.

We’ve begun reinvesting in growth, supporting our paid media and Meta efforts, and expanding our creative team to produce more content and ads. More creative output means more chances to connect with customers and fuel a rebound.

We’re also rethinking channels beyond direct-to-consumer. Target was a strong retail partner for years. Retail as a channel still holds potential — perhaps it’s independent salons, boutique pharmacies, and grocery stores. The goal is to diversify. Beardbrand.com will always be our home base, but we’re a business that sells to people, not just an ecommerce brand.

It’s exciting to think ahead instead of looking back. We’re aiming for 7% profitability this year — that’s breakeven in my book. It provides us with a buffer for unpredictable events, such as lawsuits, audits, and air conditioning failures. The real goal is 17% profit — that’s when we can fund growth, hire employees, and breathe easier. Anything beyond that is the sweet spot where the stress and sacrifice start to feel worth it.

I’m excited again — for the team, for the future, and what we’re building.

MNLY’s At-Home AI Powers Men’s Health

Next-gen health and wellness is an apt description of MNLY. Luke Hartelust launched the platform in 2021, pronouncing it “manly,” and then pivoted twice while remaining focused on modern care for men.

The current version combines AI with home-based testing, diagnoses, and nutrition. Customers pay an upfront fee and a monthly subscription afterward.

In our recent conversation, Luke shared the company’s origins, growth, mistakes, and more. The entire audio of that discussion is embedded below. The transcript is condensed and edited for clarity.

Eric Bandholz: Tell us about your work.

Luke Hartelust: I’m the founder and CEO of MNLY, a men’s health and wellness platform. We use at-home diagnostics, AI, and advanced tech to create custom supplement, lifestyle, and nutrition solutions.

My background is in fitness franchising. I led multiple locations across Southern California and worked closely with male entrepreneurs and executives. That experience revealed gaps in men’s healthcare, particularly in the lack of proactive, preventative approaches.

Telehealth has improved access to care, but the model has flaws. Most providers have long waitlists — often up to 90 days for lab results and treatment plans due to backlogged consultations.

At MNLY, we streamlined the process. We removed the practitioner bottleneck and built a scientific advisory board to train a complex AI model. The result is an automated analysis and quick, personalized health recommendations, going from signup to actionable results much faster than traditional telehealth providers.

Bandholz: Walk me through the customer journey.

Hartelust: Customers start by purchasing our at-home blood sample kit — a simple finger prick using dried blood spot sampling, eliminating the friction of in-person visits. Once received, our partner lab processes samples within hours.

While awaiting results, users complete an 86-question health assessment. It focuses on seven areas: concentration, confidence, stamina, mood, sleep, libido, and recovery.

We combine lab and assessment data — roughly 100 data points per user — to generate a clean, easy-to-understand health dashboard. It explains results and provides reference ranges, visuals, and comparison metrics. An overall health score benchmarks the data.

Next, our AI builds a personalized health plan, including nutrition suggestions based on biomarkers and lifestyle hacks such as breathwork and even testicular cooling for hormone support.

Finally, we formulate a custom dietary supplement. Based on the user’s data, our AI prescribes specific nutrients and doses. We then manufacture the supplement and ship every 30 days. It’s fully automated.

Bandholz: What does it cost customers?

Hartelust: The initial lab kit is $199. Supplements are $249 per month.

We recommend retesting with new blood samples every three to five months. Each time new bloodwork is submitted, our system updates all biomarkers, adjusts supplement dosages, and revises the health plan. Users experience clear visual progress, including changes to their overall health score.

We’ve just completed our first year in business. It’s our third iteration under the MNLY brand. We launched in 2021 as a nutritional subscription box provider, with two attempts.

A year ago, with this version, we didn’t prioritize retention. Our small team focused on product development, and we lacked an automated customer journey to guide and remind users about retesting. We started those reminders 90 days ago.

From an ecommerce perspective, not building that journey sooner was one of our biggest missteps. Many customers experienced strong results in the first six weeks — improved libido, mood, sleep, recovery, and focus — but when those effects plateaued, some dropped off around the five- or six-month mark. Even though biological improvements continued, users weren’t always aware without updated data. That’s why consistent testing and communication are now central to our retention strategy.

Bandholz: What’s your growth strategy?

Hartelust: As a startup raising capital in a tough market, I needed a strategic partner to expand our reach. I secured a deal last year with Hyrox, an indoor fitness competition, as its exclusive U.S. men’s health partner. I landed the deal with just a minimal viable product and a pitch deck, right before Hydrox’s U.S. expansion took off.

The company’s events grew in a year from 2,000 athletes to 14,000, and its audience — 50,000 social followers, 30,000 email subscribers, and 200 gym partners — aligned perfectly with our brand. We paid for the sponsorship, but it gave us massive exposure, credibility, and direct access to our core demographic.

We could have taken out, say, $100,000 in Meta Ads. That same $100,000 in a strategic Hyrox sponsorship gets us brand equity, athletes, investors, and a much lower acquisition cost — around $200 per customer, far better than we could achieve with ads alone.

Bandholz: How do you convert Hyrox athletes?

Hartelust: A presence on-site at the competitions is our most effective strategy. We recently wrapped an eight-month national tour where we set up our brand installation inside each venue. Our core leadership team was there to bring deep product knowledge, passion, and real connection.

The sponsorship provided us with access to email lists and social media audiences. Before the competition, we emailed attendees with offers, a discount code, and booth details. We reminded them of the promotion during the event and shared recaps after. We encouraged the participants to show the code at the booth for a lower rate.

Bandholz: How did you raise the capital to fund such a complex launch?

Hartelust: I spent the first six years of my career building wellness and fitness studios and nurturing strategic relationships. When we sold the company in 2021 for several million dollars, I reinvested some capital to start MNLY. But, again, before our current model, MNLY failed twice as a subscription box concept. I lost a lot on those early versions before pivoting to what we have now.

Launching this model required more than just personal funds, so I began raising a true pre-seed round about 18 months ago. I had raised capital before, but never for a startup. I tapped every possible connection — friends, family, clients — and hired a virtual assistant for cold outreach. One of our venture capital partners shared a valuable investor database. I ended up doing roughly 250 pitches and raised just under $800,000.

This round focused on micro angels rather than traditional VCs. Many brands rely heavily on Meta ads and lack a real connection. We leveraged our Hyrox community and offered equity to athlete ambassadors, which provided us with additional operational capital. That blend of brand, relationships, and community has fueled our growth.

Bandholz: Where can people support you?

Hartelust: Our website is getMNLY.com. We’re @getMNLY on Instagram and Facebook. I’m on LinkedIn.

Ecommerce to Real Estate: An Owner’s Story

Shakil Prasla once owned 12 ecommerce consumer brands generating $50 million in combined annual revenue with 50 employees. But he grew weary of the fluctuating revenue and non-stop marketing, so he pivoted during Covid to wholesale personal protective equipment.

That’s when he and I last spoke. The PPE business, Gloves.com, had misgauged demand and lost, initially, a whopping $6 million. He has since recovered and pivoted again, this time to real estate and convenience-store gas stations.

He’s an example of resilience, priorities, and seizing opportunities. He shared those lessons and more in this our latest conversation.

Our entire audio is embedded below. The transcript is condensed and edited for clarity.

Eric Bandholz: Give us a rundown of what you do.

Shakil Prasla: I own Gloves.com. We primarily sell disposable protective gloves for medical, food service, and other industries, mostly wholesale. We import from overseas, store our inventory in warehouses, and have a team of sales representatives who build relationships and sell to large distributors, such as Sysco.

Sysco, in turn, supplies restaurants and businesses like McDonald’s and Taco Bell. Orders flow through backend integrations, and while we use automation, we’re essentially a logistics company: importing, storing, and distributing goods.

I acquired the business with a private equity group. The brand has been around for over 30 years, so it came with an established sales history. When evaluating it, we looked at total market share — disposable gloves are a surprisingly massive, multi-billion-dollar industry. They’re used everywhere: hospitals, nail salons, barber shops, grocery stores, even gardening.

While gloves are our core offering, we also provide other disposable wearables, such as bouffant caps and beard covers. What I learned from ecommerce is that consumables drive strong repeat business. Customers reorder when they run out, which increases lifetime value and makes the business model attractive.

I bought my first online business in 2013, before acquiring ecommerce brands was popular. I enjoyed improving and growing them. By 2018, I owned 12 brands, generating over $50 million in annual revenue with more than 50 employees.

During Covid, I sold most of my brands and transitioned into wholesale distribution of personal protective equipment. Now, I’m also involved in real estate — buying land, building strip centers, and gas stations around Austin, Texas.

Bandholz: You scaled this business quite a bit.

Prasla: We acquired the company with just the inventory — no team, no tech — so we had to rebuild it from the ground up. Fortunately, it had been a large business with strong brand recognition, so we focused on the low-hanging fruit: reactivating old customers.

We reached out to clients from 15 to 20 years ago and informed them that the brand had new ownership, improved service, and the same trusted products. We addressed past issues and emphasized improvements — faster shipping, better pricing, and consistent product quality. That approach worked well, and many customers returned.

Unlike ecommerce, where you’re constantly running ads on Facebook, Google, TikTok, and writing emails, we don’t rely on traditional marketing. Our sales reps do the marketing. They follow KPIs, and their bonuses are tied to performance. That incentive structure has been a key driver of our growth.

Bandholz: How do you find operators and get aligned so they can thrive and help scale the business?

Prasla: I realized early on that operations aren’t my strength — I get bored by the day-to-day details. Back in my ecommerce days, I started outsourcing operations. I hired someone from what was then oDesk (now Upwork) to handle customer service, agency calls, and other tasks. At first, it was messy because I didn’t have proper operating procedures, but I refined the process over time.

Finding great people is hard. A one-hour interview isn’t enough. Candidates are selling themselves, and what they present isn’t always accurate. So there’s a trial-and-error phase.

Today, we use staffing agencies, LinkedIn, and platforms like Monster. My human resources team handles job postings, and we make sure to clearly outline the role — for example, “I need a leader to run a nine-figure business and inspire sales reps.” That clarity helps attract the right people.

Incentives are also critical. Some candidates seek a stable income, while others prefer a lower base pay with high performance bonuses. I try to understand what motivates them and tailor compensation accordingly.

To filter applicants, we include a short questionnaire: “If you were running this company, how would you grow it?” Only thoughtful responses move forward. Then our team conducts interviews, and I speak with the final candidates. That’s the process that’s worked for me.

Bandholz: What is your relationship with the CEOs?

Prasla: I keep it simple. One 30-minute call per week, focused on high-level strategy. We review a dashboard with key metrics, including revenue, what’s working, what’s not, and where the opportunities lie. I get the agenda in advance, and we stick to it.

I don’t micromanage. My job is to empower, not control. I give CEOs guardrails — for example, “Let’s grow from $1 million to $1.2 million this year.” Then I ask how they plan to do it. They break it down into quarterly and monthly KPIs. Maybe the goal is to increase conversion from 1% to 1.5% through home page A/B testing. I guide the direction, but they own the execution.

That ownership is key. When they create the plan, they’re more committed to achieving it.

Compensation for a seven- or eight-figure company typically includes a base salary ranging from $150,000 to $300,000, plus phantom equity that vests over time, profit sharing, and performance bonuses.

If my CEO brings in an extra $1 million in value, I’m happy to share in that. It’s about alignment — when they win, we all win.

Bandholz: Tell us about the shift into real estate and convenience stores, and getting into strip malls.

Prasla: My move into real estate came from two things I noticed in ecommerce. First, the ecommerce revenue was unpredictable. One month it would be up, the next it would drop due to factors such as algorithm changes, underperforming ads, or supply chain issues. It was stressful, and I wanted more stability. Second, I wanted to build long-term wealth through equity, not just profit. Real estate gave me both.

It’s been a fun challenge. I enjoy negotiating land deals and working with brokers, developers, and banks. Once I find a property, the real planning begins — figuring out the building footprint, engineering, architecture, and sometimes dealing with environmental or access issues. It’s rewarding to see a project come to life from the ground up.

I’m not the general contractor — I hire one to manage all the subcontractors, including plumbing, roofing, MEP, and foundation, among others. We also work with about 20 professionals per project, including architects, engineers, and traffic consultants. Financing typically requires a down payment of 20–35%. After construction and getting a certificate of occupancy, it takes about six months to stabilize.

This isn’t a flip strategy for me — I plan to hold the properties long term. Traffic at busy intersections brings consistent footfall, unlike the volatility of ecommerce.

After years of grinding, experiencing burnout, and incurring some losses driven by ego, I’ve reevaluated what truly matters. I have two young kids, and now my priority is time — being present. I built a stable financial base, and now I’m focused on enjoying the next chapter.

Bandholz: Where can people find you?

Prasla: Gloves.com is our business for disposable products. Our convenience stores — called Snack Stop  — are in Austin, Texas, where I live. I’m on LinkedIn.

Faith, Family, and Ecommerce

Michael Simpson is a New Mexico-based father of seven and a National Guard veteran. Returning from a 2021 deployment, he sought a business to acquire, hoping to move on from his previous job. A listing from the Quiet Light brokerage caught his attention.

Discount Catholic Products had launched in 2003 and was for sale. The company’s mission appealed to Michael. Plus it was not reliant on Amazon or a single product or imports from China — all key requirements. He purchased the business.

Fast forward to 2025, and the retailer perseveres. Michael’s role has evolved to part-time oversight. A single employee, his sister-in-law, runs daily operations with help from his kids.

In our recent conversation, he and I discussed financing the acquisition, cash flow challenges, marketing tactics, and more. Our entire audio is embedded below. The transcript is condensed and edited for clarity.

Eric Bandholz: Who are you, and what do you do?

Michael Simpson: I own Discount Catholic Products, an online retailer of spiritual goods, such as prayer cards, decorative crosses, and church supplies. It launched in 2003, and my wife, Catie, and I bought it in 2021. We ran it together for a couple of years, but recently I accepted a job with the National Guard, where I’ve served for 22 years. We have seven kids who help with the business, as does my sister-in-law, our only employee.

I found the business through Quiet Light, a brokerage. I’d been on their email list for a year. I wanted something that wasn’t reliant on Amazon, with its own website, not tied to a single product or imported from China. I also wanted a product I could genuinely care about. This listing was the first that fit my criteria and budget.

I saved about $40,000 for a down payment from a deployment in Africa with the National Guard. After returning, during the pandemic, I didn’t want to go back to my old job.

To acquire the business, we injected our down payment and borrowed from the Small Business Administration, securing a 10-year loan at a 5.5% interest for the first five years. Plus the seller carried 5% of the purchase price on a 10-year loan. I also secured a line of credit early, which I highly recommend.

Four years in, we’ve paid about 25% of the debt.

Bandholz: Has the business met your expectations?

Simpson: There were definitely surprises. The business carried about $75,000 in inventory across thousands of SKUs. I negotiated that down to $65,000, but probably still overpaid by $15,000. A lot of it was stale items that sold maybe one unit a year or not at all.

I also underestimated working capital needs. I figured cash flow would be smooth with immediate revenue from customers and 30-day terms with U.S. suppliers. However, our cash quickly evaporated as we expanded and purchased more inventory.

I assumed only about 10% of products were drop-shipped, mostly larger or more expensive items. In reality, it was a lot more. That became a problem as the global supply chain fell apart during Covid. Products from Italy, China, and even the U.S. were delayed or unavailable, leading to backorders.

So early on we shifted to more in-house inventory. We now run our own warehouse from our base in Albuquerque, New Mexico. We sell and ship low-cost, low-margin, lightweight products. The pick-and-pack fees of a third-party fulfillment provider would wipe out profits.

Bandholz: Did the seller have employees?

Simpson: She ran it with a friend, who handled pick, pack, and ship, as well as customer service. She decided to sell when the friend couldn’t continue. I underestimated the amount of work involved. I assumed my wife and I could handle it easily.

But it turned out to be nearly full-time for both of us. My wife handled fulfillment, while I managed customer service, reordering, website updates, and finances. We hired an employee early on, but she moved away. The next hire didn’t work out. So for about two years, my wife was doing fulfillment a few times a week, and I was managing everything else.

Then we had our seventh baby about a year ago. With a newborn and several homeschooled kids, my wife couldn’t keep working in the business. So we hired her sister, and it has worked out well. She works part-time, from about 9:00 a.m. to 1:30 p.m. — enough time to handle fulfillment and customer service.

Bandholz: You’re now employed outside the business.

Simpson: Yes. I realized a few months ago I was borrowing from our line of credit to pay myself a modest salary, which made no sense. I’d been praying the business would improve, and soon, an unexpected opportunity came up — working with the National Guard on a local project. It pays double what I was paying myself and has regular hours, so I took it. Now I’m focused on reducing debt and stabilizing the business, which is being run day-to-day by our one employee.

We have a 30% contribution margin, but that wasn’t enough to cover fixed costs and my salary. Once I stepped back, the business became profitable again. Ironically, sales are now up even though I’m barely involved. A mastermind peer joked, “I think you found the problem!”

Now I’m focused on high-impact tasks such as ordering inventory and launching email campaigns. I’m training our employee to take on more responsibilities. My goal is to fully step out of daily operations and focus on long-term growth — working on the business, not in it.

Bandholz: How do sales break down between individuals and churches?

Simpson: About 80% of our sales come from individuals, with the rest from churches and schools. We have amazing customers.

One woman received a broken statue, so we shipped another. She ended up fixing the first one, sold it on eBay, and sent us the money. Another customer purchased a replacement necklace, then found the original and asked to pay for both. We’ve had dozens of stories like that — just honest, kind people.

Churches are great customers. They place large orders — $500 to $1,000 — but without the red tape of big organizations. Often, it’s parish secretaries or priests placing the order, and they tend to buy year after year.

Bandholz: What’s your marketing strategy?

Simpson: We’re primarily a demand capture business, not demand generation. Meta Ads haven’t been profitable — we’re lucky to break even. However, Google Shopping ads consistently deliver a return of 4.0 or higher. We also rely on organic search traffic. Social media has never been a big sales driver.

Email has been critical. The previous owner had a distinct tone, but we’ve since shifted to our own voice, which resonates well. Customers often respond warmly, and many older buyers even call to place their orders directly.

Bandholz: Where can folks buy your products and connect?

Simpson: Our site is DiscountCatholicProducts.com. I’m on X and LinkedIn.

Don’t Exit for the Wrong Reasons

We often frame selling a business as “exiting.” But it’s a decision to walk away, to quit. That’s not negative, but it’s important to examine your reasons. Some are valid, others less so, and many fall into a gray area that deserves deeper thought.

Ideally, founders build a business they love, one that enhances their life. Business is, to me, one of life’s greatest gifts. It offers freedom, wealth, connection, and the ability to serve, create, and leave a mark on the world.

The headphones I use, the tools I carry, the art on my wall — all exist because someone built them. Entrepreneurs shape society. That’s the power of business.

This week’s “Ecommerce Conversations” is my fifth master class on entrepreneurship, following installments on hiring, branding, profit-building, and priority-setting. For this episode, I’ll address the reasons — valid or not — for selling a business.

My entire audio dialog is embedded below. The transcript is condensed and edited for clarity.

Invalid Reasons

The decision to sell a business is of course subjective. My view is owners often sell for invalid reasons, such as the following.

Believing another business is easier

Sure, some businesses may seem simpler, but what’s easy for one person is hard for another. It depends on your skills, team, and experience.

Business is a series of never-ending problems to identify, prioritize, and solve. Jumping to another doesn’t escape problems — it trades one set for another. If you think the next venture will be problem-free, you’re chasing an illusion.

Consider instead how to make your current business more enjoyable. Solving that problem — how to love showing up every day — is a worthwhile pursuit.

Wanting to ‘retire’

Lying on the beach, traveling nonstop, or restoring cars may sound appealing, but they are misguided. Work is a gift, not a burden. The true win is designing work around what you love, with people you enjoy, and on your own terms.

Ask yourself, “How do I create a business that lets me work on what I want, when I want, with people I want to work with?” If you can’t solve it now, you won’t likely solve it with the next venture.

Many entrepreneurs do fulfilling work, enjoy time with their families, and travel the world — not by quitting, but by shaping their businesses to support the life they want.

Valid Reasons

Certainly owners have many legit reasons to sell. Here are a few.

Partner problems

If you aren’t philosophically aligned with your partner(s), it’s nearly impossible to run a successful company. Misalignment in vision, values, or decision-making creates friction, and that tension will eventually stall progress or tear the business apart.

If you’ve made a genuine effort and still can’t find common ground, then it might be time to sell.

Failure of minimum viable product

The idea of an MVP is to test the market at a low cost. If the early results are poor with an uphill battle to gain traction, it may be wiser to quit early rather than sink tens of thousands of dollars into something the market doesn’t want.

The best products solve a specific problem for a targeted audience and generate genuine interest, even in highly competitive markets.

If your product doesn’t build momentum, consider cutting your losses and continue testing, refining, and seeking the ideal market fit.

Bankruptcy

If you’ve exhausted all options — negotiating with creditors, extending credit, selling assets, liquidating inventory — it’s time to step away.

Filing for bankruptcy doesn’t define you. It simply means you took a risk to build something new, and it didn’t work out. Many successful entrepreneurs have declared bankruptcy. It’s not a personal failure — it’s part of the learning process.

Use the experience as a stepping stone. Rebuild your confidence, reflect on the decisions, and learn from the lessons. That knowledge will serve you in the next venture.

Poor health

Serious health issues could signal a time to reassess. No business is worth sacrificing your well-being.

Find a way to integrate healthy habits, such as exercise, nutrition, and stress management, while continuing to build. But protecting your health sometimes means walking away and starting over. You only get one life. Time is your most valuable asset, and if your business is actively shortening it, the cost is too high.

Poor growth outlook

If you’ve hit a long-term growth plateau, selling the company is an option. The key is long-term. A business that has stalled for a few months or even a couple of quarters might have only a temporary setback. Ask yourself, “Are your expectations realistic? Are you experiencing the natural ebb and flow of entrepreneurship, or is this truly a dead end?”

Dive into the root cause. Is your market too small? Is profit razor-thin? Are there operational inefficiencies or overly aggressive growth strategies that aren’t yielding the desired results?

If you’ve exhausted all strategic options, it might be time to consider what’s next.

A life-changing offer

Getting a life-changing offer might tempt you to sell. Maybe you told yourself, “If I ever get $5 million, I’m out.” Then that offer comes. But here’s the catch: If you haven’t figured out what’s next, you might find yourself with time and money, but no direction. Many entrepreneurs discover they actually enjoyed building their business, and that magic doesn’t come back.

Especially if you’ve built it with partners you love and trust, selling is like a divorce. Once the business ends, so might that tight-knit bond. Great partnerships are rare and irreplaceable.

Selling when a strong offer arrives can be a smart move, but be clear on what comes next.

Declining market

Think Blockbuster — once a giant, but eventually overtaken by Netflix and Redbox.

Netflix pivoted — from DVD-by-mail to digital streaming, then to original content creation — completely transforming their business model. Blockbuster did not.

Before selling or closing your business, consider whether there is a pivot opportunity. If beard trends shift, could Beardbrand, my company, expand into men’s grooming or women’s products? An innovative pivot can keep you relevant, no matter how the market changes.

Pro Tennis Player Pivots to Ecommerce

For years Jack Oswald was a touring tennis professional. He aimed for top worldwide rankings, the key to serious earnings. The rankings never came, but constant travel exposed a nagging problem: his tennis bags kept breaking.

Thus began his passion for designing a better bag for athletes on the go. And that led to Cancha, a direct-to-consumer seller of sport and travel bags, which he launched in 2019 from his base in the U.K.

Jack and I recently spoke. He discussed his transition to entrepreneurship — early struggles, raising capital, and more. Our entire audio is embedded below. The transcript is condensed and edited for clarity.

Eric Bandholz: Tell our guests who you are and what you do.

Jack Oswald: I’m the founder of Cancha, which means “court” in Spanish. We design customizable, modular sport and travel bags — gear that transitions easily between work, play, and fitness. Our mission is to make sports travel seamless and help people stay active.

My background is in tennis. I spent years training and traveling to compete, chasing the dream of going pro. I didn’t reach the top, but I learned a great deal and gained valuable global experience, including learning French and Spanish.

Before the pandemic, I began designing bags for myself to meet the needs of an athlete on the move — from court to city to nature. I had no background in soft goods design, but I dove in. During the pandemic, with travel and tennis on hold, I focused full-time on building Cancha and learning ecommerce.

Initially, our target market was traveling athletes, but most customers today are everyday commuters and recreational players. We’re especially popular in the U.S., which accounts for 60% of orders. Brexit made selling in Europe more challenging, so the U.S. became our primary market. Interestingly, we also have a loyal customer base in Asia, including Japan, Hong Kong, and Singapore, despite not marketing in those locales.

Bandholz: Tell us more about the transition from tennis to entrepreneurship.

Oswald: It was a long, gradual process. As a kid, I believed nothing could stop me from turning pro. But reality hit — tennis is tough to make a living in. Only the top 100 players earn well, and beyond 150 in the rankings, you’re often losing money. Unlike soccer, where thousands of players make a living, tennis is financially brutal unless you’re at the top.

I gave it everything — traveling constantly, chasing ranking points, trying to survive each week. The grind was intense, and you’re often alone without the same resources as competitors. A coach, decent accommodations, or even a meal can make a big difference. The mental and physical toll is enormous, especially when facing losing streaks or setbacks.

I eventually realized I needed a new path. I probably would’ve kept pushing had I not discovered a new passion with Cancha. Many of my peers struggled post-tennis, but I was fortunate to find something meaningful. Even so, it took over a year to fully shift. I was still half-committed to tennis while building Cancha, gradually accepting that it was time to move on.

Bandholz: Bags are expensive to manufacture. Where did you get the money?

Oswald: It started scrappy. I wasn’t spending much at first. I was learning from friends who knew about soft goods design. Between tennis tournaments, I attended trade shows, where I met suppliers who generously offered samples, perhaps thinking I was more established.

In late 2019, I ran a crowdfunding campaign, raising approximately £10,000 ($13,500). I had no marketing experience, but it provided a bit of capital to move forward. Then, during the pandemic, we received a government relief loan, which helped fund our first production run and enabled us to undertake better design work. That was a major boost.

We began with tennis bags because that’s what I knew. The concept was a modular system — bags with add-ons for shoes, laptops, or wet gear. We first tried a backpack with racket add-ons, but it was too bulky. So we pivoted to a dedicated tennis bag and expanded from there.

Having contacts in the U.S. tennis space — reviewers and influencers — helped us get early traction. From there, we’ve grown into other racquet sports and more lifestyle-oriented bags.

A main reason for launching Cancha was frustration — my tennis bags kept breaking. Tennis is a growing sport, but the industry itself remains largely traditional, especially in marketing. Most brands rely on sales representatives and retail, and their bags are often poorly made, used as loss leaders to sell rackets. Unlike golf, where premium bags are the norm, tennis bags lack innovation and quality.

I saw a gap for better materials, thoughtful design, and durability. That became our focus: premium, modular bags that meet the needs of modern players and travelers.

On the marketing side, I also wanted to break the mold. Most tennis brands rely heavily on player sponsorships, but those come with restrictions — players who wanted to use our bags often couldn’t. So we went direct-to-consumer via ecommerce, bypassing the old-school gatekeepers.

Bandholz: How did your growth evolve?

Oswald: It has been gradual. We haven’t had a breakout moment from ads or gifting — no “rocket ship” success. It’s been a steady improvement across the board. Our bags are significant purchases. They last a long time, and people take time to decide. That makes acquisition challenging, especially with rising ad costs.

Our limited production approach has worked well. We’ve leaned into that with email marketing — offering limited-edition drops, exclusive colorways, and brand collaborations within tennis and beyond. We’ve also done a lot of pre-orders.

Creating excitement around the product development process and scarcity has helped drive engagement and interest. Instead of relying on one big channel, it’s been a mix: building hype, maintaining a tight brand, and slowly earning trust.

Bandholz: Do you have repeat buyers?

Oswald: Yes, and that’s been a strength. Our modular design allows customers to add accessories, naturally encouraging repeat purchases. People often buy a base bag first, then return for add-ons.

I design accessories to stand alone while also integrating with our bags. That dual approach gives us crossover appeal — some people buy just the laptop bag, while others build complete travel systems over time.

Limited drops play a role, too. Customers offer feedback on what they want. That helps guide future product development. We’ve had customers spend upwards of $2,000 over a few years. That kind of engagement has been key to our growth.

Bandholz: Where can people buy your bags or reach out?

Oswald: Our site is MyCancha.com. I co-host the Underdog Ecom Podcast for bootstrapped owners. I’m on X and LinkedIn.

Great Mom Builds Global Craft Biz

Sally Wilson is a lawyer turned craft entrepreneur. She’s also an involved mother who shares her business and passions with two kids. She says being a great mom doesn’t mean sacrificing who you are.

Sally launched Caterpillar Cross Stitch a decade ago from her home in England. Fast forward to 2025, and her company has 12 employees, selling cross-stitch supplies, courses, and events to customers worldwide.

In our recent conversation, she addressed early struggles, leadership lessons, global selling, and yes, raising kids. Our entire audio is embedded below. The transcript is condensed and edited for clarity.

Eric Bandholz: Tell us what you do.

Sally Wilson: I own an ecommerce company called Caterpillar Cross Stitch. We sell cross-stitch and crochet kits, subscriptions, and run events and classes — everything stitch-related — from our base near Birmingham, England.

I launched the business nearly 10 years ago after leaving a law career I hated. I took an ecommerce course and followed the advice: find a niche, a community, and a product people love.

I bootstrapped the business from the start, using savings and reinvesting carefully. I’d always wanted to work for myself, originally thinking I’d open a law firm, but I knew I needed something outside of law.

We now have a team of 12, including my husband, who joined the business three years ago. He was an engineer, but juggling two careers and raising kids was tough. On our 10th anniversary trip, I suggested we work together toward the same goal, and he joined soon after.

Working together wasn’t easy at first. There was conflict, especially since we discussed the business at all hours. But we set boundaries and now work in separate offices. I handle marketing and design, he runs operations. We’ve found a strong balance and deep respect for each other’s roles, which makes the business — and our marriage — work.

Bandholz: How have you adapted your leadership style with a larger team?

Wilson: I’ve learned that not everyone thinks or works like me. Early on, I assumed everyone approached things the same way, but I’ve come to appreciate that people are gifted differently. This awareness has made me more mindful and patient. Now, I focus on balancing my style with what works best for the team.

In the early days, I was more rigid, expecting people to fit my workflow. Coming from a law background, where I worked alone in a closed office, this was normal. But business, especially creative work, requires more interaction. Now, I’m much more intentional about how I communicate to bring out the best in others.

I try to make our employees feel safe sharing how they best receive communication. I’ve done a lot of reading, including recently exploring the distinction between feedback and criticism. Feedback, when delivered well, is a gift — it helps relationships and growth. But criticism, even if it sounds the same, can feel harsh and unhelpful if it lacks intention. It’s all about how it’s delivered.

I’m emotional and reactive by nature. Sometimes my husband and I go to bed angry — and that’s okay. Time offers perspective, and I’ve learned to own how my words or tone contribute to how something lands.

Bandholz: What’s your vision for the business?

Wilson: I want Caterpillar to be the brand women think of for crafting, especially in the U.S., Canada, Australia, New Zealand, and parts of Europe. Australia, in particular, is an exciting opportunity. The data shows a passionate, underserved community there that we haven’t fully tapped into yet. I’d love to give it more focus.

More broadly, I’m driven by the idea that you only get one life — so why not see what’s possible? That’s not about always winning or having the right answers. It’s about being resilient and reframing failure as learning. You either win or you grow. I’ve let go of fears and leaned into trusting myself: Even if I don’t know something now, I believe I can figure it out.

It comes down to grit, consistency, and a refusal to quit. That mindset has carried me this far, and it’s what I’ll continue to bring as we scale globally.

But my health and my children come first. For years, I sacrificed sleep, working until 2 a.m., and it took a toll. Now I’m more intentional. If I’m not well, the business suffers too.

As a mom, especially a female entrepreneur, there’s a lot of pressure to step back, work part-time, or choose a less demanding path.

But showing up fully for both my business and my kids is the example I want to set. I pick them up from school every day, attend nearly all their events, and I’m always available. They see how hard I work, how driven I am, and how lit up I get when things go well. I think that’s powerful for my daughter and son to see that passion.

Being a great mom doesn’t mean sacrificing who you are. I want them to grow up with open minds, strong values, and a real understanding of what it means to chase their purpose.

Bandholz: Where can people follow you?

Wilson: Our website is CaterpillarCrossStitch.com. We’re on Facebook, YouTube, Pinterest, Instagram, and TikTok.

Build a Business You Love

For this week’s “Ecommerce Conversations,” I’m offering another master class on entrepreneurship. It’s my fourth this year, following episodes on hiring, branding, and profit-building.

My goal is to help existing and future entrepreneurs based on operating Beardbrand, my direct-to-consumer company, for a decade now. This installment is my most important master class to date. It’s about setting priorities for business and life.

My entire audio is embedded below. The transcript is edited for clarity and length.

Purpose

A common entrepreneurial mistake is building a business without intention or purpose. There are many ways to approach entrepreneurship, but I focus on creating a company that gives me freedom — doing what I want, when I want, with people I enjoy working with. That’s my North Star, and it influences every decision.

Your North Star might be different, but it’s important to define it early. For me, I lean toward less drama and more personal freedom. Bigger companies with rapid growth often have more lawsuits, employee issues, and general chaos. I keep things simpler to avoid unnecessary headaches.

If you aim to build a massive, high-growth company and sell it for millions as quickly as possible, this approach isn’t for you. But if you value a sustainable business that supports your lifestyle and aligns with your values, that’s what I’m here to share.

Profit Equals Freedom

A common mistake for entrepreneurs is chasing revenue instead of bottom-line profit. They obsess over gross sales, but the key is what you can keep, your net profit. High revenue with slim margins won’t give you freedom.

Money has never been important to me. My first job paid $11 an hour at a Dell call center. My parents were upper-middle class and supportive, but they were not investors in Beardbrand beyond buying products and cheering me on.

What kept me afloat was simple math: spend less than you earn. When income drops, cut expenses. When income rises, save aggressively. That cycle of living below my means has created financial stability over time.

Remember, freedom comes from strong margins.

Improving margins means lower costs (mostly for products and customer acquisition), higher prices to customers, or both. Entrepreneurs tend to focus on marketing, such as Facebook and Google ads and search engine optimization. But those channels can become more expensive over time and erode margins.

It’s just as important to lower the cost of goods while improving the end products so customers will pay more. Efficient supply chains and nonstop product improvement are critical.

A common trap is holding onto low-margin products because they generate top-line revenue. If a product doesn’t contribute to your bottom line, it’s not worth keeping — you’re working for free. But don’t abandon products too quickly. Test ways to cut costs, raise prices, or acquire customers more affordably. If those efforts fail, discontinue the item.

External Funds

Entrepreneurs often take on loans or seek investors, but the goal should always be to build the company without outside debt or equity.

The traditional route — bank loans, venture capital funding, or friends and family — means taking on debt or giving up ownership. A better option is customer financing. Crowdfunding platforms such as Kickstarter sell your product to consumers before it exists, providing seed money and real-world feedback while reducing risk and maintaining ownership. No debt payments. No investors telling you how to run your business.

Before borrowing money, ask if there’s another business to build first, perhaps a product launch in small batches. To start Beardbrand, I made 100 bottles of beard oil in my kitchen. Small beginnings can still lead to freedom.

Remember why you started. Is it for freedom, wealth, or ego? For those chasing freedom, avoid debt if possible. Fund your business in a way that keeps you in control.

Long-term

Too many business owners have a short-term mindset. We’re all bombarded with stories of entrepreneurs selling their businesses for millions. That narrative gets beaten into our heads: build fast, exit fast, make millions. But think long-term. Not just five or 10 years out, but 50 or 100 years — a multi-generational business.

For that to happen, you have to love showing up every day. And that usually starts with being profitable. Losing money is not fun. Cut unprofitable products, downsize, or humble your lifestyle to fix cash flow.

Beyond finances, entrepreneurs choose who they work with. That’s a gift.

Ultimately, think about your kids. Would they want to take over your business? If so, integrate them in a way they enjoy, not out of obligation. That requires investing time with your family now, away from the business, so they’ll want to be part of it later.

Self-invest

A long-term vision does not mean neglecting other aspects of life. I’m investing in my health and mindset — ensuring my body and mind are ready for my kids, grandkids, and the company as I age.

I exercise six days a week — three lifting and three rowing. I built a garage gym for time-saving convenience.

For my mental health, my family and I travel to Denmark every summer. It’s not a vacation — I still work — but being in a new place sparks adventure. For me, that’s travel. Others may value hobbies, gardening, or whatever keeps their lives interesting.

Priorities

How we spend our time is a key decision in life. It starts with knowing our priorities — serving our body, mind, business, spouse, kids, and friends.

I write in a Moleskine notebook what’s important to me. Then I rank them. No ties, no equals. For me, family ranks above business.

But above all, I prioritize my health and mindset. I can’t show up for my wife, kids, or company if I’m absent physically, mentally, or emotionally. You can’t pour from an empty cup. Get clear on your list.