How can you tell if your 10+ year old startup is gearing up for a sale, and more importantly, for what kind of sale? (Like to a competitor, private equity, or something else?)

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People are answering the wrong question. OP thinks their company may be getting ready to be sold.

OP. Sales usually involve some combination of many of the following:

Requests for copies of the company's financials.
People asking for documentation for various core systems or services.
People gathering key contracts with vendors and customers.
Questions about core metrics that you haven't received before.
Contracts or contacts with investment banks, auditors, advisory firms.
Lots of hush-hush meetings with Sr execs, especially CEO, CFO, and GC.

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1. How consistent is your income generation? Do you have long-term contracts in place?
2. What percentage of the market share do you own and is it growing/static? Are you a threat to the largest competitor? Would they or anyone else be interested? (You can usually figure this out pretty easily)
3. What is your GIM? This is one way to value your company but there are far more complex/robust ways. This is just a baseline to see what it might be worth.
4. What is the talent pool at your company like? Would everyone stay if you sold out or is the culture so great that people will stay.

If you have relatively positive answers to these, you might be a good candidate for a buyout (or expansion).

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If you think a 10 year company still operates as a startup, it is ready

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Hiring freeze or headcount reduction. Project/initiative delay, reduction, re-clarification, or reprioritization. Contract, SOW, invoicing, and income statement roundup. Tons of investors & boards meetings (which generate ad hoc internal reporting requests). Stress in upper management. Stuff like that…

If your company makes between 12 and 24 million per year, you're in a "sweet spot" for a sale. If there is a sudden focus on process/procedure or abandonment of some future plans in favor bulletproofing existing products that might be a sign. Some of your key executives going off on business trips together might tip you off. A company considering a sale is likely to lay off or remove any personnel not absolutely critical to maintaining the business. A "consultant" might join the team to help do something that involves review of some or all operations. That said, most negotiations are predicated on confidentiality (break that and the deal is off), so don't expect the few, and it will be as few as possible, involved in those efforts to let anything slip.

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