Technical Debt: What it is, How Much of it You Can Live With, and How to Incorporate it into an Investment Thesis

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”

Evaluating Customer Retention in Recurring Revenue Businesses: With Craig Zingerline

My Guest Craig Zingerline is a serial entrepreneur currently working as the CEO of Growth Minded, a company that helps startups and other technology companies scale their growth and retention strategies. Prior to Growth Minded, he founded Velocity Growth and scaled to 7-figures of ARR, was Chief Product Officer at Sandboxx, and the Head ofContinue reading “Evaluating Customer Retention in Recurring Revenue Businesses: With Craig Zingerline”

Leverage: Doing More With Less

Listen to this Blog Post “Give me a lever long enough, and a place to stand, and I will move the earth.”– Archimedes “Leverage” is one of those concepts that tends to be interpreted as being more complex than it actually is. The simplest way to define leverage might be “the ability to do moreContinue reading “Leverage: Doing More With Less”

You Don’t Have an Engineering Problem, You Have a Product Management Problem

My Guest Rich Mironov is one of North America’s preeminent Product Management thought leaders. He has spent 40 years in the software industry in numerous capacities, and currently acts as a Coach, Consultant, and Interim Executive for CEOs and Heads of Product across Canada and the United States, advising them on a diverse range ofContinue reading “You Don’t Have an Engineering Problem, You Have a Product Management Problem”

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”

A Deep Dive on Hiring

Listen in Your Browser Questions Asked Randy Street (3:30) Many of you will know Randy Street as co-author of the book Who: The A Method for Hiring, which introduced the now widely used Topgrading hiring method to the world. The book went on to become a New York Times, Wall Street Journal, BusinessWeek, USA Today,Continue reading “A Deep Dive on Hiring”

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?”

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”

The Biggest Temptation of a Software CEO

Listen to This Blog Post In his book, The Five Temptations of a CEO, author Patrick Lencioni discusses five areas in which CEOs tend to inadvertently prioritize the wrong things. These “temptations”, as he calls them, can lead to poor decision making at best, and can risk the very survival of the company at worst.Continue reading “The Biggest Temptation of a Software CEO”