Looking For An Exit? Five Mistakes To Avoid

Forbes

2 days ago

Dr. Keegan Caldwell is the founder and global managing partner of Caldwell.
Over the years of guiding companies through exits—from scrappy startups to established tech giants—I've watched too many brilliant founders torpedo their own valuations with mistakes that could have been avoided with proper planning.
The stakes couldn't be higher. Bain & Company recently found investments and exits are "up 37% and 34% respectively," but for companies that managed to close last year, more than a third had been on that road for over two years. Only 21 exits last year exceeded $1 billion in value, with large, return-generating exits far more scarce than smaller deals.
The fact is, many founders are making the same preventable errors that can cost them millions in valuation and, in some cases, jeopardize the entire deal. Here are the five most damaging mistakes to see and how you can avoid them.
1. Treating IP As An Afterthought
The most expensive mistake founders make? Failing to get their intellectual property house in order before starting exit conversations. I've seen deals collapse entirely because buyers discovered that key IP wasn't properly assigned to the company or was entangled in licensing disputes that would take years to resolve.
This goes beyond filing patents. Your IP audit should include employee invention assignments, contractor agreements, open-source software usage and any third-party licenses that your technology depends on. The problem often traces back to the early days when founders were focused on building rather than documenting—but those shortcuts become expensive roadblocks when buyers start their due diligence, which ideally begins at the onset of exit negotiations.
Maintaining a clear, organized IP portfolio from the start is ideal. But if you don't have this, I recommend you start your IP cleanup at least two years before you're planning to kick off exit discussions. This gives you time to fix any gaps, file additional patents for recent innovations and make sure all your documentation is rock-solid.
Remember: Buyers aren't just acquiring your current IP; they're betting on your ability to defend it against future challenges.
2. Financial Opacity That Kills Buyer Confidence
Clean books are crucial for financial transparency, telling a story through your numbers that buyers can actually understand and trust. Too many founders think they can polish their financials during due diligence, but sophisticated buyers spot inconsistencies right away.
Common issues I see are revenue recognition problems, especially with SaaS companies that haven't properly accounted for subscription revenue, and undocumented expenses that make buyers wonder about your financial controls. Buyers also want to see predictable, recurring revenue streams, not one-time spikes that make your numbers look better than they are.
Invest in proper accounting systems and regular financial audits well before you're ready to exit. Document your revenue recognition policies, keep detailed records of all expenses and be ready to explain any weird stuff in your numbers. The companies that get premium valuations are the ones where buyers can clearly see the financial trajectory and trust the systems generating those numbers.
3. Ignoring Cultural Due Diligence
Buyers aren't just acquiring your technology or customer base—they're inheriting your team, your culture and your operational processes. Cultural misalignment is one reason acquisitions can fail to deliver expected value, yet it's often overlooked during exit planning.
Smart buyers conduct extensive cultural due diligence, interviewing key employees, assessing retention risk and evaluating whether your team can integrate successfully with their organization. Companies with high employee turnover, poor management structures or toxic cultures can get heavily discounted or passed over entirely.
Therefore, start building a scalable, documented culture early. This means clear policies, documented processes, strong management practices and measurable employee satisfaction. Buyers want to see your company can operate effectively without the founder's daily involvement—because that's exactly what they're buying.
4. Overestimating Market Interest
The biggest ego trap in exit planning is assuming multiple buyers will compete for your company. Most founders dramatically overestimate buyer interest, leading to unrealistic expectations when it comes to timing, valuation and negotiation leverage.
The reality is that there are typically only a handful of logical buyers for any given company, and they all have specific criteria, timing constraints and competing priorities. I've seen founders turn down solid offers while waiting for better ones that never materialize, then watch their leverage evaporate as market conditions shift.
Conduct realistic market analysis before you start the process. Identify your most likely buyers, understand their acquisition criteria, review their recent deal history and have honest conversations about what makes your company attractive to them specifically.
5. Holding On Too Long
The most painful mistake is waiting too long to exit. I've seen founders who've built incredible companies they intend to exit from hold on well past their peak, watching valuations decline as competitive pressures intensified or market conditions changed.
This often stems from emotional attachment or unrealistic expectations about future growth. Founders can fall victim to the mental trap of convincing themselves they need "just one more quarter" to hit certain metrics. The fact is, market windows can close quickly. The companies that achieve the best exit outcomes are often those that sell while they're still growing, not after they've hit a plateau.
Develop clear exit criteria early in your company's life. This might include reaching a certain revenue threshold, achieving market leadership in your category or simply recognizing when you'll have taken the company as far as resources allow.
Think about why you want to exit, write that down and stick to it. The best exits happen when you're selling from a position of strength, not scrambling to find buyers because you're running out of runway.
Your Exit Starts Today
The most successful exits I've orchestrated began years before the actual transaction. Every decision you make about IP protection, financial systems, team building and market positioning either strengthens or weakens your eventual exit position.
Start thinking about your exit strategy now, even if it seems far away now. The companies commanding premium valuations and achieving successful transitions are those building with the end in mind, not those trying to retrofit exit readiness.
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