Chris Kille: How did delegation save his life and business?

Chris Kille is a serial entrepreneur who exited multiple companies, and we spoke about how running everything himself nearly killed him—and why delegation changed everything. At his first exit, he was earning a few million a year but doing every job himself, until “they thought I had a stroke.” That moment forced a hard reset: if the business depends on the founder, it’s fragile, stressful, and worth far less than owners believe.

We talked through the practical method he learned the hard way: replacing yourself step by step. Chris explained why founders should offload admin first, then customer support, then marketing—before sales—so revenue doesn’t collapse under its own weight. He shared how documented workflows, SOPs, and clear expectations matter more than heroics, and why “80% done by somebody else is a hundred percent awesome” when it frees the founder to lead.

Chris also unpacked the deeper reason this matters. Removing himself from daily operations didn’t just increase valuation and exit multiples; it gave him his life back. As he put it, “Systems matter more than people,” because strong systems survive churn, scale without burnout, and protect what matters most—health, family, and time.

If you’re building a company that feels stuck, exhausting, or unsellable, this conversation offers a concrete blueprint for turning effort into leverage—and a business into an asset.

Key takeaways

Founder-dependent businesses get lower exit multiplesNearly burning out forced delegation and changeHire admin first, not salesDocument SOPs for every repeatable taskStrong systems outperform individual talentDelegation creates time, health, and freedom