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Best of Bootstrapping: The Buy Side of Bootstrapping to an Exit

Posted on Friday, Mar 1st 2019

I am sure you are following the Bootstrapping to Exit (let’s call it B2E) articles. Last time, I showed you some case studies of larger companies who are acquiring bootstrapped startups.

In this post, I will double-click down on the buy-side psychology of the B2E phenomenon.

There are several factors that play into a relatively larger company acquiring a smaller player.


Companies acquire for different reasons. Some acquire to bring in substantial chunks of high growth revenue. Some acquire to bring in adjacent products that their sales force and channel can upsell to existing customers. Some acquire to diversify out of a one-trick pony situation. Sellers need to consider the buyer’s psychology and accordingly steer the conversation.

Valuations vary significantly depending of motivations. Revenue-driven acquisitions tend to be easier to put a price on. Valuations tend to be a multiple of the revenue, regardless of how much money the company has raised.

Strategic acquisitions tend to be more complex to value. They resemble the thought process of a VC. If I acquire your company, how much additional TAM does that open up for me? Can I leverage my sales force and channel and push your products through them? How much additional engineering is needed before we go to revenue? Have you raised too much money, making the valuation expectations irrational?


Today, products are built on technology stacks that are often incompatible. This makes merger integrations challenging. Take for example a SaaS company acquiring another that is on a different technology stack. What is the cost of rationalizing the two stacks post acquisition? Is there enough ROI post rationalization to go ahead with the transaction?

This also points to the fact that if you build on a compatible stack with an eye towards a B2E situation, your chances of finding a successful exit would be higher.’s Platform-as-a-Service (PaaS) strategy is a very good example. Numerous startups built on this stack, making it easy for Salesforce to acquire and integrate.

As you design your startup’s strategy, please keep in mind that the technology choices you make will determine whether or not you can find a satisfactory B2E outcome.


Culture matters tremendously. Whether an acquisition can be integrated successfully or not is often the factor of compatible cultures. If you are working with a B2E objective, study the culture of the potential acquirers and make sure you don’t get tripped with vastly incompatible dynamics.

There are other factors, but these three are the top ones.

Related reading: Qualys Acquires 1Mby1M Company Adya

This segment is a part in the series : Best of Bootstrapping

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