10 hours ago
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: info@equity-launchpad.com
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.
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