My Guest Chris Smith is the Managing Partner of Spellbound Partners, a a company that helps acquirors with technical due diligence, fractional CTO services, and outsourced development services, among other things. Chris has over 25 years of experience building software platforms, and is an expert in cloud computing and software as a service (SaaS). HeContinue reading “Technical Debt: What it is, How Much of it You Can Live With, and How to Incorporate it into an Investment Thesis”
Tag Archives: technical debt
From Combat to Classrooms: How Jim Vesterman Went from Special Forces to a 13.5x Return in 8 Years
My Guest My guest today is Jim Vesterman, currently a lecturer at the Wharton School at the University of Pennsylvania. Prior to joining the faculty at Wharton, Jim was the CEO of Raptor Technologies between 2012 to 2020, where he grew the company from serving 7,000 schools in the United States to serving over 40,000Continue reading “From Combat to Classrooms: How Jim Vesterman Went from Special Forces to a 13.5x Return in 8 Years”
The Constellation Software Playbook for Acquiring and Growing Software Companies
My Guest Constellation Software is one of the world’s most admired, well-followed, and well-respected software acquirors. Since their founding in 1995, they have acquired over 500 individual software companies, and have grown to achieve $8.4B in revenue and a $77B market capitalization. They have achieved these staggering metrics through their exclusive focus on the lowerContinue reading “The Constellation Software Playbook for Acquiring and Growing Software Companies”
The 2023 SaaS CEO Survey
Listen to this Blog Post The Data Set The year in which each target company was acquired is detailed in the chart to the right. As can be seen, we were able to achieve reasonably good diversity by vintage year, with 18 of the 41 transactions taking place in 2019 or earlier, and 23 ofContinue reading “The 2023 SaaS CEO Survey”
Are You Selling to the Wrong Customers?
Listen to this Blog Post In my experience, among the countless strategic decisions that software CEOs must make, the decision of which end markets to serve doesn’t seem to command the time, attention, and level of thoughtfulness that it probably should. Leaders who run mature and established companies often take comfort in the product/market fitContinue reading “Are You Selling to the Wrong Customers?”
Evaluating 5 Very Different Approaches to Acquiring a Software Company
Listen to This Blog Post Enterprise software is considered to be among the world’s best business models, and for good reason: Revenue tends to be highly recurring. Switching costs, pricing power and customer retention rates are often high. And businesses have the ability to scale in a non-linear fashion owing to the fact that additionalContinue reading “Evaluating 5 Very Different Approaches to Acquiring a Software Company”
Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdge
My Guests My guests today are Steve Lau and Rameez Ansari, co-CEOs of AutoLeap, a cloud-based auto repair shop platform that counts Bain Capital Ventures among its investors. Prior to founding AutoLeap, Steve and Rameez purchased, operated, and sold D’Esco (later renamed FieldEdge), a software company that helps entrepreneurs run their HVAC, Plumbing, and ElectricalContinue reading “Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdge”
Considerations Unique to Acquiring a Software Company (Product)
Listen to this Blog Post: In a previous blog post, I discussed several financial considerations unique to acquiring software companies, specifically those of the small-to-medium-sized variety . In this week’s post, I present several non-financial considerations for the prospective acquiror to consider. Much of what I discuss below is intended to uncover how much “technicalContinue reading “Considerations Unique to Acquiring a Software Company (Product)”