This is an Open Coffee for Fractionals session — part of my coaching practice.

Chris Hilton joined this session as he considered stepping into the fractional CTO path. Kevin Knoepp and Diego Woitasen brought in their own perspectives from private equity portfolio work and consulting.

The conversation moved from DevOps history into the real challenges of building a fractional business: positioning, pricing, politics, and people.

We got into:

• Early stage startups expecting a fractional CTO to act like a founder
• Navigating equity offers and why they’re really investment decisions
• Deciding when to take loss-leader projects for credibility
• How much politics you can (and can’t) avoid in leadership roles
• Building trust through content and positioning
• Using contractors and agencies to keep momentum post-acquisition
• The limits of job interviews vs. building a client pipeline

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded August 11, 2025
🎙️ Hosted by David Raistrick

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