Show Notes

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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