Having Hard Conversations (Live Panel Discussion from 2022 MIT Sloan Search Fund Summit)

In this week’s episode, we discuss the importance of having difficult conversations, something that CEOs find themselves doing on a near-daily basis. We discuss three primary types of difficult conversations, including: Hard conversations around internal company dynamics (eg: terminations); Hard conversations about dynamics external to the company (eg: politics and global affairs); Difficult conversations thatContinue reading “Having Hard Conversations (Live Panel Discussion from 2022 MIT Sloan Search Fund Summit)”

Quality of Earnings Analysis: What You Need to Know Before Buying a Business

My Guest My guest today is Chris Hutchinson, a Partner in Ernst & Young’s Transaction Advisory Services Group. Chris has over 15 years of experience advising clients on M&A, financings, valuation projects, and due diligence mandates, with a specific focus on private lower-middle-market businesses. Chris and his team have completed an untold number of QualityContinue reading “Quality of Earnings Analysis: What You Need to Know Before Buying a Business”

Lessons Learned in Capitalizing an Acquisition

Listen to This Blog Post Among the myriad variables that must be carefully considered when acquiring a business is the question of how the acquisition is going to be financed. My intent in the material that follows is not to cover the countless options available to acquirors stemming from this question (that wouldn’t be possibleContinue reading “Lessons Learned in Capitalizing an Acquisition”

What M&A Lawyers Want CEOs to Know About Selling Their Companies

My Guest Mario Nigro is one of Canada’s preeminent M&A lawyers, and currently serves as a Partner in the Mergers & Acquisitions and Private Equity & Venture Capital Groups at Stikeman Elliot based out of Toronto. His practice focuses on mergers and acquisitions, financings, complex corporate reorganizations, and general business law. Mario has extensive experienceContinue reading “What M&A Lawyers Want CEOs to Know About Selling Their Companies”

Rich Manders: Lessons from Founding, Growing, Buying, Selling, Coaching, and Investing in SMBs

My Guest Rich Manders Co-Founded and led iAutomation, a Massachusetts-based machine control and automation company, and grew the business from $0 to $90M in sales with 180 employees. After selling that business to The Riverside Company (a leading global Private Equity firm), Rich stayed on with the business, and alongside his partners at Riverside, grewContinue reading “Rich Manders: Lessons from Founding, Growing, Buying, Selling, Coaching, and Investing in SMBs”

Busting the Biggest Myth About Selling Your Business

Listen to This Blog Post The entrepreneurial journey is full of innumerable risks: Your largest customers can leave at any time, and for any reason. The market may change faster than your company’s ability to adapt. Your largest supplier may decide to cut you out of the value chain and simply build your product themselves.Continue reading “Busting the Biggest Myth About Selling Your Business”

Migrating Your Company from On-Premise to SaaS: Part 2

This is the second post in a two-part series on navigating the transition from on-premise to SaaS. You can read Part 1 here. Listen to This Blog Post: In Part 1 of this blog, we evaluated some of the more common challenges that companies face when attempting to migrate both their product and revenue modelsContinue reading “Migrating Your Company from On-Premise to SaaS: Part 2”

The Private Equity Perspective on Acquiring, Operating and Selling Software Companies

My Guest Jordan Bettman is a Partner and Co-founder of Radian Capital, a New York-based Private Equity firm focused on B2B software and technology-enabled services businesses. Radian has ~$500 million of assets under management, and is now investing out of their second fund of ~$315 million. Prior to co-founding Radian, Jordan was a Partner atContinue reading “The Private Equity Perspective on Acquiring, Operating and Selling Software Companies”

Migrating Your Software Company from On-Premise to SaaS: Part 1

Listen to This Blog Post: The overwhelming majority of software companies founded over the past fifteen years or so have never known anything other than a cloud-based, single-server-multi-tenant architecture coupled with a subscription revenue model. If you’re running a software business that fits this description, then you’ll (thankfully) never need to navigate the transition thatContinue reading “Migrating Your Software Company from On-Premise to SaaS: Part 1”