A surprising insight that challenges conventional thinking about business ownership and strategic planning.
Every SMB owner should take their business to market once a year or so.
And they should self-list it.
That seems to be the conclusion we came to when I was talking to a young business owner that bought his business a couple of years ago.
Here's what he said:
"Buyers ask the best questions.
When you're a small business owner with a small staff, in a lot of ways you need to be your own personal coach which is very difficult.
Talking to the potential buyers will help me see the best ways to improve my business..even if I don't end up selling it."
This perspective challenges conventional thinking. Most owners list their businesses only when they're ready to exit. But what if the process of listing a business could serve as one of the most powerful strategic review mechanisms available to entrepreneurs?
When you run a business day-to-day, you develop blindspots. You become accustomed to operational inefficiencies, market positioning weaknesses, and growth limitations that an outsider immediately identifies.
Potential buyers bring a uniquely valuable perspective:
Buyers analyze your financials with forensic precision, identifying areas where profitability could be improved or where accounting practices need refinement.
They evaluate your systems, processes, and organizational structure with fresh eyes, often spotting inefficiencies invisible to those embedded in the business.
Buyers assess your competitive positioning and market opportunity with strategic objectivity, sometimes identifying pivot opportunities or untapped markets.
They focus intensely on what drives valuation in your business, providing clarity on which improvements would most significantly impact your company's worth.
Buyers methodically identify business risks and dependencies that owners often overlook or underestimate.
No consultant, advisor, or coach brings the same combination of rigorous analysis and genuine self-interest as a potential buyer evaluating a purchase opportunity.
Beyond the practical feedback, there are psychological advantages to regularly testing the market:
When you periodically view your business as a saleable asset, you make different decisions. You begin focusing on building transferable value rather than just managing operations.
Regular exposure to the selling process reduces the emotional grip that can cloud judgment about major business decisions.
Consistently seeing the market value of your business keeps exit options present in your strategic thinking, preventing entrenchment.
Receiving legitimate offers provides concrete validation of your business's worth, either building confidence or providing reality checks.
This psychological reframing has powerful effects on decision-making quality and strategic clarity.
While the benefits are compelling, this approach isn't without potential complications:
These considerations don't invalidate the approach, but they do suggest the need for careful implementation.
If you're intrigued by this unconventional approach, consider these implementation strategies:
Rather than choosing between total secrecy and complete openness, consider a middle path:
The original suggestion emphasized self-listing. This approach:
However, working with a broker on a limited engagement might provide:
To maximize value from the process:
Annual listing might be too frequent for some businesses. Consider:
The right cadence might be 18-24 months rather than annually, depending on these factors.
If the full listing approach seems too extreme, consider these alternatives that capture some of the same benefits:
Hire valuation professionals every 12-18 months to conduct formal business valuations, including detailed feedback on value drivers and detractors.
Engage M&A advisors or business brokers for "sell-side due diligence" to identify issues buyers would focus on, without actually listing.
Some investment bankers will provide informal market feedback sessions, discussing how buyers would view your business in the current market.
Join entrepreneur peer groups where members conduct structured reviews of each other's businesses, providing outside perspective.
Hire experienced advisors to conduct simulated due diligence, identifying issues before real buyers do.
These approaches provide valuable outside perspective without some of the risks of actually listing your business.
This strategy isn't equally valuable for all businesses. It likely delivers maximum benefit when:
If you genuinely would sell if an exceptional offer emerged, the process becomes more authentic for all involved.
Very small or owner-dependent businesses may receive limited useful feedback beyond the obvious dependency issues.
Some industries have more sophisticated and knowledgeable buyer pools than others.
In very small markets or highly visible businesses, confidential listings may be impractical.
The process requires the ability to receive direct criticism of your business without taking it personally.
The suggestion that SMB owners should regularly take their businesses to market is unconventional but potentially transformative when implemented thoughtfully. Few other mechanisms provide the same level of objective, motivated scrutiny of your business as potential buyers conducting acquisition due diligence.
Whether you fully embrace this approach or adapt elements of it to your situation, the core insight remains valuable: the buyer's perspective reveals business improvement opportunities that are difficult to identify from within.
If that's the case, should all business owners intentionally take their business to market every year or so?
If they get a great offer, that's great. But either way they'll receive great feedback that they can't get any other way.
The answer isn't a universal yes or no, but rather a thoughtful consideration of whether this approach—or a modified version of it—could provide you with strategic insights that drive your business forward, whether or not you ever actually sell.
The Unconventional Wisdom: Why Listing Your Business for Sale Annually Might Be Brilliant Strategy