HoldCo Builders From VC to Main Street: How AI Is Rewiring Service Businesses
12 snips
Dec 3, 2025 Cyrus Hessabi, an investor-operator with a rich background in aerospace engineering and venture capital, shares insights on transitioning from VC to private equity at Shore Capital Partners. He discusses how AI is revolutionizing traditional service industries, revealing that ripe opportunities exist in sectors like property management and accounting. Cyrus defines AI-enabled services as transformational tools rather than replacements and emphasizes the importance of evaluating founder capabilities. His journey illustrates the blend of optimism and discipline essential for success in this evolving landscape.
AI Snips
Chapters
Books
Transcript
Episode notes
Early Spark From Aerospace Workflows
- Cyrus traced his interest in modernizing traditional industries back to his first aerospace job where workflows were paper-based despite advanced engineering.
- That early frustration seeded his thesis of bridging tech and the traditional economy using data and AI.
Blend VC Optimism With PE Discipline
- Combine VC tolerance for J-curves with private equity execution discipline when building AI roll-ups.
- Ensure services deliver quality and cash from day one while pursuing technological upside.
Define AI-Enabled Services From First Principles
- AI-enabled services are rebuilt services businesses that start from first principles with AI tools in the toolbox.
- Cyrus contrasts building software vendors with building new service firms that use AI to beat incumbents on cost and outcomes.
