Acquiring Minds Why Choose Ownership Over Being a CEO
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Nov 10, 2025 Katherine Butler-Dines, an entrepreneur and former CEO, and Rahul Desai, a technologist and operator, share their transformative journey from being bound by traditional CEO roles to pursuing self-funded ownership. They discuss the challenges of acquiring a business while juggling day jobs and highlight their innovative back-office solutions that enhance margins in the travel industry. With a vision for a rollup strategy in niche brands, they emphasize the importance of majority ownership for balancing growth and lifestyle, as well as the economic advantages of travel businesses.
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Ownership Enables Values-Aligned Decisions
- Katherine realized operating under PE constraints forced profit-first decisions that clashed with her human-centered values.
- She concluded she needed majority ownership (51%+) to run a business aligned with her values.
Early Search: Lots Of Deals, One Tragic Near-Miss
- Rahul and Catherine looked at ~80 full deal memos and 100+ cursory deals while self-funding their search.
- Their first near-deal fell apart when the seller's house burned and they withdrew due to seller hardship.
Build Deal Muscle By Seeing Volume
- See as many businesses as possible to build deal-evaluation skills and pattern recognition.
- Use marketplaces and low-commitment inquiries to practice screening quickly.
