The "Breakthrough AI Operators" Podcast
Subscribe & Listen
Real AI founders.
Real operating breakthroughs.
No vendor agendas.
Breakthrough AI Operators features founders who didn't just adopt AI — they rebuilt how their company makes decisions, deploys talent, and competes. One guest. One honest story. 30–45 minutes.
Listener Traction
Views
21,900+
across YouTube & podcast
Hours watched
243+
in 2026 alone
Active Listeners
214
dedicated audience
Subscribers
1,088
on YouTube
Founders who have shared their story
Over 100 honest conversations with builders from Silicon Valley and the global startup ecosystem — honest about the mess, the method, and what it actually took.
COMPANIES FEATURED AS GUESTS
RECENT Conversations
100+ episodes
EP 200 · MIDSTAGE ACCELERATOR
Why We Built Breakthrough AI Operators
Roland Siebelink & Doug Miller
EP 105 · PACTUM
While You Sleep, My AI Agents Close Deals in China
Kaspar Korjus — Founder & CEO, Pactum
EP 118 · KIKOFF
I Spent My 18th Birthday Studying Credit Cards. Now I Run a Unicorn.
Cynthia Chen — Founder & CEO, Kikoff
EP 120 · EQVISTA
Building Company Valuations That Take Hours, Not Months
Tom Milar — CEO, Eqvista
EP 102 · DAISY
The AI-Native Approach to Managing Buildings
Yotam Cohen — Cofounder & CEO, Daisy
EP 117 · LITHIC
Why Craft Still Matters in Fintech

Robin Gandhi — CPO, Lithic
WHAT GUESTS are SAYing
“Most podcast hosts want the press release version of your story. Roland wanted the operating model — how the decisions actually get made. That's a rare conversation to have in public.”
Kaspar Korjus — CEO, Pactum
“I came in prepared to talk about product. We ended up going somewhere more interesting — how you actually scale a team without losing the judgment calls that matter. Roland had clearly done his homework.”
Cynthia Chen — Founder & CEO, Kikoff

“Roland got to the heart of what we built before I'd finished explaining it. That prep call is real — you don't go on cold, you go on ready to say something worth hearing.”
Tom Milar — CEO, Eqvista
About the Show
What Makes This Show Different
Most AI podcasts are vendor pitches with a microphone. This one isn't. We talk to founders who are in the middle of it — honest about what worked, what didn't, and what cost them more than they expected.
Not a Vendor Parade
Our guests use AI. They're building and operating companies, not selling AI products. They're honest about the wins, the failures, and the surprises — because they have no agenda other than telling the truth about what it actually takes.
Operators, Not Engineers
We don't talk inference costs or model architecture. We go deep on operating models: how decisions get made, how teams own outcomes, and how founders stop being the bottleneck in every critical judgment call.
The 50% Startup
We believe AI does the work — humans decide what the work is for. Every episode draws that line honestly and explores what it means for how a real company organizes itself to compete and win.
Track Record
100+ episodes across three shows
Built over years, one honest founder conversation at a time. This isn't a new podcast experimenting with format — it's a proven platform with a growing audience of founders, investors, and senior operators.
1
Midstage Startup Momentum
90+ episodes
The original show. Roland started interviewing founders on what it really takes to build a lasting company — before the hype cycles, before the playbooks got commoditized.
2
Scaling Without Breaking
25+ episodes
The show that built the audience: founders, investors, and senior operators across Silicon Valley and the global startup ecosystem. Focused on the inflection points that make or break a company.
3
Breakthrough AI Operators
Episode 200 and counting
The current show — focused on founders who are rebuilding how their company operates with AI at the foundation, not bolted on as a feature layer.
Your Hosts
The People You'll Be Talking To
Roland and Doug aren't commentators. They've built from the inside — scaling companies through the hard inflection points that don't appear in the case studies until after the fact.
Co-founder, Midstage Accelerator
Roland helped scale 3 unicorns from ~10 to ~1,000 employees — in three different countries — each resulting in an IPO or equivalent outcome. After 16 years in Silicon Valley, he founded Midstage Accelerator to bring those operating lessons to founders before they learn them the hard way.
Co-founder, Midstage Accelerator
Doug has built 4 unicorns from the inside. He joins the show as co-host and interviewer, bringing the kind of pattern recognition that only comes from seeing the same inflection points play out across dozens of high-growth companies — and knowing which signals actually matter.
7
Unicorns Built
Companies scaled using the Midstage operating system
100+
Leadership Teams
Transformed across the portfolio and accelerator
2.5–3
Years Avg. Engagement
Founders stay because the work compounds
For Prospective Guests
What to Expect as a Guest
We don't put founders on camera cold. Every episode starts with a prep call, and every guest reviews their episode before it goes live. Here's exactly how it works.
01
30-Min Prep Call
Roland shapes the story arc with you before we ever hit record. You come into the conversation knowing what we're covering and why it matters — not winging it.
02
45-Min Recorded Conversation
Relaxed, real, unscripted. The story arc we built on the prep call, told in your words. No teleprompter, no pre-approved questions delivered cold.
03
Pre-Launch Sync
We coordinate with your marketing team before the episode drops. You get cross-promotion support — clips, graphics, timing — not just a Spotify link the morning it goes live.
04
Your Story, Your Way
You review the episode before it goes live. If something doesn't represent you or your company accurately, we fix it before the world hears it.
Ready to Share Your Breakthrough?
We review all applications and respond within 5 business days. If your story fits, we'll make it worth your time.
For Guests
Share your breakthrough story
We're looking for founders who have made AI a structural part of how their company runs — not a tool layer on top of the old way of operating. If you've rebuilt how your team makes decisions, deploys talent, or competes using AI, we want to hear it.
We review all applications and respond within 5 business days.
For Listeners
Never miss an episode
New episodes weekly. Founders who have done it — honest about the mess and the method. No filler, no hype. Subscribe on the platform you already use and the episodes come to you.
"We believe AI does the work — humans decide what the work is for. Every episode explores that line, honestly."
— Roland Siebelink & Doug Miller, Co-hosts
Breakthrough AI Operators is produced by Midstage Accelerator — the firm that has helped build 7 unicorns and transformed 100+ leadership teams. The podcast is one part of a broader operating system for founders who want to win at scale.