Bring your network to the table.
Table Stakes is a private, invite-only roundtable for middle-market business owners and operators — 8–12 to a table, an honest conversation about AI: what it is, what’s working, and what it means for how you run your business. No vendor pitches. Facilitated by Frogslayer. Free.
Small groups. Honest conversation.
We keep each table to 8–12 operators (capped at 12) so everyone stays in the conversation. It’s invite-only, practitioner-led, and run under one rule: what’s said in the room stays in the room. No slides, no demo, no one selling to anyone.
- Fluency on what these tools actually are — and where they help, where they don’t.
- A shorter list of the decisions only you can make, and a clearer view on what to delegate.
- A real sense of what other operators your size are actually doing (not what vendors claim).
Best two hours I’ve spent on AI strategy all year. No vendors, no slides — just operators being honest about what’s working and what isn’t.
A structured conversation, not a lecture.
Every table follows the same shape — tight enough to stay on track, open enough to go where the room needs to go.
Where AI is actually working in middle-market operations right now, what’s changed lately, and what to ignore.
Peer discussion: specific examples, real numbers, real deployment stories from operators in the room.
Honest conversation about what isn’t working — data, vendors, adoption, budget. No judgment. Just candor.
A practical framework for deciding what to build first — business impact, data readiness, and capacity.
Ask anything. We stay to answer specific use-case and engagement questions and how to apply what you heard.
The conversations that matter most usually happen after the formal session ends. We leave time for that.
~2 hours over a meal, plus open networking. A half-day commitment — a year’s worth of clarity.
What the room has tackled.
Twenty years of high-stakes workshops behind us — here are themes participants have dug into.
AI in field service dispatch — what’s actually working
Using AI to improve scheduling, cut windshield time, and dispatch smarter — without replacing the field team.
Pricing intelligence for PE portcos
CPQ, margin visibility, and how PE-backed companies use AI to sharpen pricing and protect margin at scale.
Data readiness — the honest conversation
Why most AI projects fail before they start, and what the operators who succeeded did to get their data house in order first.
Replacing manual workflows without breaking the business
Automating approvals, reporting, job costing, and compliance without disrupting the operations keeping revenue flowing.
Tech integration after acquisition — avoiding the traps
What happens to your stack after a deal, and how operators consolidate systems without losing continuity.
Building the AI business case for your board
Quantifying ROI, structuring the case for leadership, and setting KPIs that hold tech partners accountable.
It’s the only room where I can ask a dumb AI question and get a straight answer from someone who’s actually done it.
Built for operators. Not observers.
You’ll fit right in if
- You’re an owner, CEO, COO, or CFO at a middle-market company
- You’re PE-backed or on an acquisition / growth path
- You’ve tried AI and hit walls — data, integration, or adoption
- You want unfiltered peer input, not vendor demos or consultant pitches
- You’d rather hear what other operators are actually doing than read another think-piece
- You’ll speak openly under the room’s confidentiality rule
It’s not for you if
- You’re looking to sell something to the room
- You want a product demo or a sales pitch (this isn’t that)
- You’d send a junior delegate instead of attending yourself
- You want a passive lecture or webinar
- You’re not willing to share real challenges and real experiences
Straight answers.
Is it really free?
Will you pitch me?
Who else is in the room?
Is it confidential?
What if none of the dates work?
How long is it?
We run Table Stakes in small batches across Texas.
Request a seat below and we’ll reach out with the details. Dates firm up once a table fills.
Save your seat at the table.
Tell us a bit about you and which date works. We’ll confirm by email — small tables, so seats go fast.
- 8–12 to a table — invite-only
- No vendor pitch, no slides, free
- What’s said in the room stays in the room
I came in skeptical and left with three specific things to stop doing. Worth clearing the calendar for.
Reserve your spot
Tell us a bit about you and which date works. We’ll confirm by email — small tables, so seats go fast.