Breakthrough AI Operators
By Roland Siebelink
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Category: Management
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Episodes: 24
Description
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.
| Episode | Date |
|---|---|
|
The AI Breakthrough Stories Most Founders Are Not Telling | Midstage Accelerator | Doug Miller | EP 200
|
May 27, 2026 |
|
From PE Boardroom to Operator — What Investors Get Wrong | HCIM | Ali Evans | EP 122
|
May 13, 2026 |
|
Why 20 People Can Beat Billion-Dollar AI Companies | Deep Infra | Nikola Borisov | EP 121
|
May 06, 2026 |
|
Built real-time private company valuations that take hours, not months — while staying profitable in an industry where competitors bleed money | Eqvista | Tom Milar | EP 120
|
Apr 30, 2026 |
|
I Left My Company. Came Back to Find a Shell. Then Rebuilt It. | Wundertax | Daniel Hanemann | EP 119
|
Apr 25, 2026 |
|
I Spent My 18th Birthday Studying Credit Cards. Now I Run a Unicorn | Kikoff | Cynthia Chen | EP 118
|
Apr 16, 2026 |
|
Why Craft Still Matters in Fintech | Lithic | Robin Gandhi | EP 117
|
Apr 07, 2026 |
|
Shipping Every Week: The Release Strategy That Finally Unlocked Fieldmagic's Growth | FieldMagic | Glen Richmond | EP 116
|
Mar 31, 2026 |
|
When Half Your Industry Thinks You're Dead Wrong | Mobio Interactive | Besh Saab | EP 115
|
Mar 25, 2026 |
|
How to Place Big Bets Without Betting the Farm | SeedLegals | Anthony Rose | EP 114
|
Mar 20, 2026 |
|
The more AI spam there is, the better for my team! | Kontaktikeskus | Erki Koldits | EP 113
|
Mar 11, 2026 |
|
We spent $12M chasing product-led-growth. Then doubled revenues by ignoring it. | Portainer | Neil Cresswell | EP 112
|
Mar 04, 2026 |
|
How to Scale to 8,000 Merchants with a Sub-70 Person Team | Montonio Finance | Karel Nappus | EP 111
|
Feb 24, 2026 |
|
How to Scale Enterprise Sales with A Team of 11 | Eon Media AI | Ashish Agarwal | EP 110
|
Feb 10, 2026 |
|
Bootstrapping Clinked: 14 Years of Profitable SaaS Growth | Clinked | Tayfun Bilsel | EP 109
|
Jan 27, 2026 |
|
How to Scale Yourself as a CEO Without Breaking | Markup AI | Matt Blumberg | EP 108
|
Jan 13, 2026 |
|
Weaponize the POC: How to Turn Your Biggest Sales Liability into Your Secret Weapon | Scaling Without Breaking | Provarity | Steve Davis | EP 107
|
Jan 06, 2026 |
|
Your Series A Vanishes Because You Build What You Could Have Bought | Scaling Without Breaking | Dragonfly | Sven Sabas | EP 106
|
Dec 23, 2025 |
|
While You Sleep, My AI Agents Close Deals in China | Pactum | Kaspar Korjus | EP 105
|
Dec 09, 2025 |
|
Scaling Culture Through Storytelling | Vyntra | Gerlinde Boback | EP 104
|
Nov 25, 2025 |
|
Fail 40 Times, Build a Hit | Sesh | Pepe Del Rio | EP 103
|
Nov 11, 2025 |
|
Making HOAs Loved Again | Daisy | Yotam Cohen | EP 102
|
Oct 28, 2025 |
|
Introducing Scaling Without Breaking | Midstage Accelerator | Roland Siebelink | EP 101
|
Oct 15, 2025 |
|
Scaling Without Breaking Podcast
|
Oct 15, 2025 |