Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

The real reason invoices don’t get paid has nothing to do with accounting.

Late payments aren’t just annoying, they quietly drain focus, energy, and leadership bandwidth. In this episode I sit down with entrepreneur Maximiliaan van Kuyk to discuss why trust in business payments is breaking down, and what CTOs can do about it.

Drawing on years of experience across startups, agencies, and global markets, Maximiliaan explains why accounts receivable is no longer just a finance function, but a leadership and systems problem. They explore how late invoice payments persist not because people are malicious, but because incentives are misaligned, and accountability is invisible.

You’ll hear why consistency beats confrontation, how social accountability in business can outperform legal threats, and why CTOs should care deeply about cash flow management even if they never touch invoicing.

If you’ve ever felt the quiet frustration of waiting to get paid, or watched payment delays impact runway, morale, or growth, this conversation will reshape how you think about trust systems, AI in accounts receivable, and the future of getting paid on time.

You’ll Learn:

[00:00] Introduction

[02:18] Why getting paid is really a trust problem, not a money problem

[06:41] How chasing payments drains founders emotionally and why it usually lands leadership

[10:52] What happens when small businesses become accidental lenders, and why the system works against them

[15:37] Why consistent follow-ups beat confrontation and legal threats when recovering unpaid invoices

[21:04] Why late payments persist even with contracts and how incentives shape behavior

[27:56] How social accountability changes payment behavior faster than reminders or credit scores

[34:48] Why reputation only works when it’s visible, and what hidden payment history enables

[41:22] Why CTOs need to understand cash flow risk even if they never touch invoicing

[48:09] How tracking payment behavior could reshape trust, partnerships, and who gets hired

You can connect with Maximiliaan on Instagram or find his work on his website here.

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

398: Stop Self-Doubt: How to Reprogram Your Brain for Confidence | Best Of 2025