As startups race to adopt AI, many enterprise leaders quietly admit they’re overwhelmed, underprepared, and unsure how to avoid becoming part of the 95% of failed AI initiatives. Kaspar Korjus isn’t one of them.

In this conversation, he breaks down how his company scaled AI negotiation agents from an idea to an engine trusted by Walmart, BMW, Rolls-Royce, and global enterprises moving hundreds of billions through automated procurement.

You'll hear the real story behind landing Walmart as an early customer, how founders should think about ICP discipline, the mechanics of scaling a global org across Estonia, Europe, and the US, and why freeing up mental bandwidth may be the most underrated executive skill in the AI era.

Kaspar also opens up about fatherhood, burnout-proof leadership, and the unexpected truth about work-life performance when you’re running a 100M-funded scale-up.

KEY DISCUSSION POINTS

• 00:00 — Welcome to Scaling Without Breaking
• 00:39 — The Walmart pitch that changed everything
• 01:12 — Building AI negotiation agents before it was cool
• 02:05 — Why 95% of AI initiatives fail—and why it doesn’t worry Kaspar
• 03:26 — Digital workforces + leveling the supplier playing field
• 05:16 — How AI is reshaping procurement at scale
• 06:26 — Founding story: from e-Residency to AI negotiations
• 08:15 — The Walmart negotiation—and what founders get wrong
• 10:10 — Non-linear negotiations & the myth of zero-sum deals
• 12:12 — Managing thousands of parallel negotiations
• 13:05 — Go-to-market strategy & landing enterprise early
• 14:45 — ICP discipline and the psychology of sales teams
• 16:02 — Hunters vs. farmers—when to split the sales org
• 17:12 — The shocking size of Factum’s marketing team
• 18:40 — Why the founder still needs to meet customers
• 20:05 — Avoiding “founder escalation chaos”
• 21:11 — Product vision: when (and how) to hire a CPO
• 23:18 — Europe vs. US founders—go-to-market mindsets
• 24:44 — How much should founders pre-sell?
• 26:19 — Driving internal AI adoption
• 27:46 — Creating a culture where people embrace agents
• 29:08 — The surprising internal use cases
• 30:03 — Estonia vs. US: building globally
• 31:22 — Remote culture done right
• 32:55 — Energy, trust, and the 90-day reset
• 33:19 — Childhood, Estonia, and early entrepreneurial patterns
• 35:19 — Family bankruptcy, tech, and resilience
• 36:28 — Fatherhood, Ironman training & CEO performance
• 38:11 — Creativity, mental space & leadership
• 39:56 — Books and influences
• 40:43 — How to reach Kaspar
• 41:23 — Closing thoughts

A masterclass for founders, operators, and anyone trying to scale without breaking.

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