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.