Executive offsites & strategy retreats
A three-hour block that does what a slide deck can’t: shows the leadership team how it actually behaves when the pressure is real, then gives it a framework for what comes next.
Deal With It: A Game of Entrepreneurpoly Workshop
Almost three decades of entrepreneurship. Hundreds of years of crowdsourced experience. One session.
A facilitated business simulation for executive teams and C-suites. Your leadership team makes consequential calls with incomplete information, lives with the consequences, recovers from setbacks — and leaves with a shared way of dealing with whatever comes next.
Half-day or full-day · Executive teams of 6–12, scalable to 100+ · Offsites, retreats and leadership summits
Where Entrepreneurpoly fits
New leadership teams
A new CEO, a post-merger executive team, a reorganized C-suite. Build trust and a common operating language fast, before the first real crisis forces it.
Senior leadership & succession cohorts
The next tier of executives lives a decade of ownership-level decisions in one session, with a debrief tied to the roles they’re being prepared for.
Boards, owners & partner groups
For boards, family businesses and partner-led firms: align risk appetite and decision rights in a setting that is candid without being confrontational.
WORKSHOP OVERVIEWReal scars.
Real scars.
No real bankruptcies.
Executive judgment is usually earned the expensive way. Entrepreneurpoly compresses ten years of running a company into a single session: your leadership team starts with capital and a plan, then invests, negotiates, allocates, gets lucky, goes bankrupt and builds back — using real finance mechanics and 500+ cards drawn from Igor’s almost three decades of entrepreneurship and the crowdsourced experience of hundreds of founders and operators. Hundreds of years of hard-won lessons, on the table in an afternoon.
The game is the hook. The facilitation is the point. Igor pauses play at the moments that matter — a bad deal, a lucky break, a bankruptcy — and connects them to the decisions your executive team is facing right now. The session closes with a structured debrief using the Deal With It™ framework.
Download the executive overview (PDF)The game is the hook.The facilitation is the point.
IN THE ROOM
Facilitated personally by Igor Vainshtein
Every executive session is run by Igor himself. Almost three decades as an entrepreneur, 20+ companies started, 18 that failed along the way, a TEDx talk and a keynote at the United Nations. He’s sat in the seat your executives sit in — and the cards on the table come from his failures and the failures of the founders who contributed to the deck.
~30 yrsEntrepreneurship
20+Companies Started
18Failed Along the Way
500+Cards of Crowdsourced Experience
What your leadership team
walks away with
Decision quality under uncertainty
Executives make consequential calls with incomplete information. The simulation puts that on the table repeatedly, and the debrief examines how each leader actually decides.
Capital allocation & risk appetite
Where to invest, when to hold cash, how much leverage to carry. The team sees each other’s instincts and calibrates a shared risk posture.
Resilience as an operating discipline
Setbacks and bankruptcies are built in. The debrief converts recovery from a personal trait into a repeatable leadership practice.
Revealed team dynamics
Deals and negotiations expose how the leadership team really operates under pressure — who leads, who hedges, who goes quiet — in a setting where it’s safe to name it.
A shared language for the decisions ahead
The Four Pillars give the executive team a common framework it keeps using long after the session, not just the memory of a good afternoon.
THE SESSION01 02 03 04
How an executive session runs
Igor’s story
10 minA short talk on almost three decades of building companies, 18 failures, and what actually separated the ones that made it.
Tutorial years
30 minTwo guided rounds so everyone is fluent in the mechanics before the stakes rise. No finance background needed.
Play — years 3 to 10
2–3 hrsThe team invests, negotiates, allocates and recovers. Igor pauses at key moments to draw out the lesson behind the move and connect it to your business.
Debrief & application
45–60 minThe leadership team maps what happened at the table to what’s happening in the organization, using the Four Pillars — Flip Perspective, Master Inputs, Perfect Practice, Reframe the Random — and leaves with specific commitments.
Sessions run 3–5 hours and fit as a block within a larger offsite agenda. Groups over 25 play a compressed five-year version.
Format at a glance
- Core format
- Executive team of 6–12 at a single table. Deepest storytelling, full ten-year play.
- Scales to
- 100+ for broader leadership groups — 2–4 tables for 10–25; team-based play across up to 5 tables for 25–100+.
- Duration
- 3–5 hours including debrief. Half-day and full-day options.
- Setting
- In person — executive offsites, strategy retreats, leadership summits.
- Prior knowledge
- None required. Works across finance, operations, sales, product and legal leaders.
- Igor brings
- All game kits, facilitation, and debrief materials.
- You provide
- Round tables, seating, and a screen for the opening talk.
- Customization
- Cards, scenarios and the debrief tailored to your industry and the decisions your team is facing.
- Confidentiality
- Sessions are private. What’s discussed in the debrief stays in the room.
- Pairing
- Bookable on its own or bundled with an Igor keynote for the wider organization.
Under the hood: how the game works.
What’s in every box
- 1 phasing journey board tracking years, phases and bankruptcy.
- 5 custom dice: Opportunity, Encounter, Expenditure, Got Lucky and Deal With It™.
- 2 pawns for tracking progress.
- Asset and transaction sheets for ROI, growth, loans, income, expenses and charity.
- 500+ cards drawn from real entrepreneurial experience, plus player aids and rules.
How the five phases work
The Collection Phase
Roll the dice and collect Opportunity, Encounter, Expenditure and Got Lucky cards.
The Cash Phase
Earn income and pay expenses across jobs, property, businesses, shares and loans.
The Action Phase
Invest, negotiate shares and deals, and record purchased assets.
The Charity Phase
From year three onward, each player chooses a donation; group generosity unlocks discounts.
The Growth Phase
Update asset growth and ROI at year end, then move forward one year.
What executive teams ask
Does the leadership team need finance or entrepreneurial experience?
No. Two tutorial rounds get everyone fluent. Mixed executive teams — finance, ops, sales, product, legal — work especially well because the instincts differ.
Can it be tailored to our business?
Yes. Cards, scenarios and the debrief can be built around your industry, your current strategic questions and the decisions ahead.
Who facilitates?
Igor personally facilitates every executive session. For groups above 25, he brings additional table facilitators.
Can it sit inside a larger offsite agenda?
Yes. A three- to four-hour block works well, often paired with Igor’s keynote earlier in the day so the team hears the framework and then lives it.
What about confidentiality?
The debrief regularly surfaces candid observations about how the team operates. Sessions are private, and nothing discussed leaves the room.
What happens after the session?
The team leaves with written commitments from the debrief. A follow-up session or keynote can be scheduled to hold the team to them.
BEYOND THE EXECUTIVE TEAMExtend it across
Extend it across
the organization
Deal With It: A Game of Entrepreneurpoly
Once the leadership team has lived it, the board game version brings the same experience to senior leadership programs, onboarding cohorts and team offsites.
2–6 players per table2.5–3 hours per game
Buy This GameBring Entrepreneurpoly to your executive team.
Tell us the team, the date and what you need them to walk away with. We’ll send a proposal within two business days.
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