From Horror Story to $25M Exit with Mike Krupit

In this episode of the M&A Launchpad Podcast, hosts Casey Minshew and Feras Moussa sit down with Mike Krupit, founder of Trajectify, to talk about mentoring and coaching leaders through the stages of scaling a business — from one to two, two to five, and five to ten — and what it really takes to shift from a founder-led mindset to a CEO-led one. A software engineer turned COO turned CEO across eight Silicon Valley startups over 25 years, Mike walked away from operating companies 13 years ago to build a leadership and organizational development practice instead. The conversation also digs into the acquisition side, including two very different horror stories: a forced take-private during the dot-com bust, and a $1 million company that turned an $8 million offer into a $25 million sale after a bidding war. 

In this episode, we discuss: 

• Why Mike chose coaching and advisory work over buying a business himself, and the networking exercise (75 meetings in three months) that helped him find his lane 

• The four jobs of a real CEO — visionary, right people in the right seats, fiduciary accountability, and the outside voice of the company — and the "not-to-do list" that gets founders out of the day-to-day 

• Building an accountability chart (not an org chart) and using fractional executives to delegate without adding headcount 

• Spotting the "sweet spot" between an underprepared and an over-prepared acquisition target 

• Two acquisition stories from opposite ends of the spectrum: a chaotic forced sale during the dot-com bust, and a $1 million company that became a $25 million sale after being shopped around 

• Why mastering difficult conversations — not tactics — is the real skill buyers need before, during, and after a deal 

Guest Contact Information 

Mike Krupit 

Founder, Trajectify 

LinkedIn: https://www.linkedin.com/in/mkrupit/ 

Website: https://www.trajectify.com 

Additional Resources 

Thinking about buying a business? Connect with the Equity Launchpad team to learn more about acquisition entrepreneurship and upcoming opportunities. 

Contact Casey Minshew and Feras Moussa: [email protected] 

Explore more: https://www.equity-launchpad.com 

About The M&A Launchpad: The M&A Launchpad provides insights into acquiring, investing in, and selling profitable businesses in the lower to middle market. Whether you are a business owner, investor, or aspiring entrepreneur, we will provide you with the knowledge, guidance, and capital to navigate the world of mergers and acquisitions. The M&A Launchpad presents a series of weekly podcast episodes and hosts an annual M&A Launchpad Conference tailored to the M&A community. Connect with M&A Launchpad: 🎧 Podcast on Spotify: https://open.spotify.com/show/0mW6i4ooujqC7eOPWmguU7 🎧 Podcast on Apple: https://podcasts.apple.com/us/podcast/m-a-launchpad/id1740382586 🎟️ Attend Upcoming M&A Launchpad Conference: http://malaunchpad.com/