Evaluating 5 Very Different Approaches to Acquiring a Software Company

In The Trenches

This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and to the best extent possible, I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. If that doesn’t say confidence, I don’t know what does. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.

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This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.

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Enterprise software is considered to be among the world’s best business models. However, getting access to the world’s best business model doesn’t come cheaply: Software businesses most frequently trade at multiples of recurring revenue, which stands in contrast to most other industries in which businesses tend to trade at multiples of EBITDA or cash flow.

But not all software investment theses are created equally: There are indeed several different approaches to acquiring and building a software company, and each approach presents a different investment thesis, requires different operational and value creation strategies, and is likely to command different asking prices. In today's episode, I present and evaluate 5 very different approaches that buyers might consider in their pursuit of a software business. Though this list of approaches is by no means exhaustive, it does capture those that I tend to see most frequently.

Please enjoy!