Scaling Without Breaking

About Scaling Without Breaking

Breakthrough AI Operators is a podcast about how the best startup founders are reinventing how their companies work. Not AI hype. Not vendor pitches. Real operators who've rebuilt significant parts of their business around AI — and can talk honestly about what worked and what didn't. Hosted by Roland Siebelink and Doug Miller, co-founders of Midstage Accelerator (7 unicorns built between them, 100+ leadership teams scaled), each episode features a founder who's achieved a genuine step-change breakthrough in how their company operates. These aren't productivity wins or tool adoption stories — they're companies that are structurally different because of AI. If you're a founder at a 20–300 person company actively figuring out what AI means for your operating model and competitive position, this show gives you real stories from people in the field — not consultants theorizing from the sidelines.

Publisher

Roland Siebelink

Category

business

Language

en

Explicit

No

First episode

15 Oct 2025

Latest episode

9 Jun 2026

Latest episodes

26 episodes in the feed.

1. 

   9 Jun 2026

   Most Companies Are Measuring Marketing Wrong — And AI Won't Save Them | Hawke Media | Erik Huberman | EP 202

   Erik Huberman, founder and CEO of Hawke Media, explains to host Roland how many companies misinterpret marketing data, leading to flawed decisions and ineffective AI implementation.

2. 

   3 Jun 2026

   The Unlikely AI Pioneer: How heyData Out-Innovates Flashier Silicon Valley Startups | heyData | Miloš Djurdjević | EP 201

   Roland is interviewing Miloš Djurdjević, co-CEO and co-founder of heyData, about how necessity drove their innovative AI operating model, transforming customer support and revenue operations.

3. 

   27 May 2026

   The AI Breakthrough Stories Most Founders Are Not Telling | EP 200

   Midstage Accelerator co-founder Roland Siebelink interviews host Doug about achieving AI breakthroughs in operations by focusing on team adoption over tool implementation.

Who has been a guest on Scaling Without Breaking

Names identified in recent episode analyses. Showing up to five guests.

• Erik Huberman
• Miloš Djurdjević
• Ali Evans
• Nikola Borisov
• Tom Milar

Contact Scaling Without Breaking

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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