OVER/UNDER+
The Operating Model · Investor Briefing

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People · Partners · Platforms

The Operating Model.

How O/U+ turns invested capital into acquisition instead of overhead — a tiny human core, an agentic technology stack that does the work of a department, and Partners who carry the licensing, inventory, and audience. Senior operating horsepower, without senior-hire burn.

The one-page version.

O/U+ is not a software company and isn't capitalized like one. The moat is the proven venue model, the fan relationship, and the owned first-party data — not code. So we buy or rent the technology, partner for the heavy lifting, and point an agentic stack at the work — invested capital funds the two things that compound, creative and acquisition, rather than payroll and infrastructure.

The operating rule: humans set strategy, approve, and close. Agents research, draft, enrich, personalize, and plumb. Partners do everything that would otherwise be a build or a balance-sheet risk.
5
Leadership seats — founder, operations, tech, AI & creative development
~$2–3K
Monthly software floor replacing an ops, ad-ops & marketing team
1
Role we're recruiting — an operations leader, ahead of the launch
7
Partner pillars doing work we never staff or license ourselves
People
Everyone O/U+ engages directly — the founder, tech and AI development leadership, advisors, and the operations leader we're adding. They set strategy, approve, and close.
Partners
People at other companies doing work for us — the build partner, the exchange, the books, the venues, the creators. They carry licensing, inventory & audience.
Platforms
The internal stack we execute on — ad platforms as our ad-ops team, agentic tools as our back office, one data backbone as our P&L.
O/U+One data backbone · one P&L · the truth stays in-house

Four things that must be true.

Decide first
Prize structure
Free-to-play (non-cash, <$5K per promotion) vs. sweepstakes decides our entire ad access. Locked with gaming counsel before a dollar of media.
Secure early
Channel access
Certification/permission on the ad platforms — and a community channel where we're actually allowed to promote.
Validate first
Postback proof
One end-to-end test conversion confirmed before acquisition spend. It is how revenue is recognized — a miswired postback is how CPA affiliates quietly lose money.
In seat
Technology leadership
Frank Filippi leads tech development and Jordan McCrary leads AI development — the stack, integrations, data & attribution are owned inside O/U+.

Build vs. buy vs. partner — across the whole company.

We build essentially one thing: the fan relationship and the owned data. Everything else is rented, partnered, or handed to agents.

FunctionDecisionHow we do it
Fan relationship + first-party dataBuild & OwnThe only real moat. Owned CRM/warehouse and owned agent logic — never let a partner hold this.
The AI avatar (VBA)PartnerSpecialist build partner (Biz4Group) delivers it; O/U+ owns prompts, workflows, credentials & data contractually; MCP keeps the agent layer swappable.
Licensing & compliance railsPartnerWagerWire's affiliate licenses + the CPA model keep O/U+ in the light regulatory tier, nationwide.
National reach / audiencePartnerPrediction markets as the 50-state front door; venues, teams & creators supply warm reach we didn't buy.
Ad-ops & media buyingPlatformPlatform AI runs targeting, bidding & optimization. No ad-ops hire.
Creative, ops & lifecyclePlatform + AgentAI tools generate creative at volume; agentic ops do the repetitive work under human approval gates.
Growth capabilities ×3PlatformAudience intelligence, automated GTM, and data monetization licensed separately — no single supplier grading its own performance.
The technology functionIn-houseLed by Frank Filippi (tech development) and Jordan McCrary (AI development) — the stack, integrations, data & attribution.
The dollars, plainly
O/U+ human layer
$20K / mo
Department it replaces
$45–60K / mo
A founder-led core at $8K/month + technology and AI development leadership at ~$5K + $7K reserved for the incoming operations leader and flexible senior support = $20K/month against the $45–60K/month department it replaces — plus a ~$2–3K/mo software floor. The difference becomes acquisition budget: the same raise buys materially more customers here than in a conventionally-staffed competitor.

A deliberately flat, senior roster.

Founder · Operations
Ed Berry
30+ years in ad sales & sales management; built and ran the Over/Under sports-bar concept and the O/U+ model profitably for three years. The proof, the face, and the relationship engine.
Operations
Leader of Operations — TBH
The open senior seat: day-to-day execution across venues, partners, and the member funnel — recruited against the launch and funded in the raise. Until it is filled, the founder carries it with the agentic stack underneath.
Mark Allen
CRM / ROI / ROAS
30+ yrs direct marketing & CRM — lead capture and automated remarketing for the VBA.
Dave Kirk
Retail Partnership Development
30+ yrs sales (Time Inc.), close ties to Caesars — deep venue, team & affiliate BD.
Erin Petty
AI Compliance
18 yrs PM & AI governance (Meta, WarnerMedia) — the bridge to responsible, compliant AI.
Matt Perrault
Sports-Betting "Muse"
Podcast host and authentic voice of the VBA; anchor of the creator channel.
Frank Filippi
Leader of Tech Development
Technology leadership via PsyCray — owns the platform build, the integrations, and the data backbone O/U+ keeps.
LinkedIn
Jordan McCrary
Leader of AI Development
Leads AI development for the VBA — the conversational engine, the avatar experience, and the model work behind both.
LinkedIn
Barry Burdiak
Leader of Creative Development
Leads creative development — brand, ad creative, and the content volume the acquisition engine depends on.
LinkedIn
Additional Support
Flexible senior capacity · TBH
$7K/mo reserved — creative, BD, or ops — deployed wherever the launch shows strain.
How the AI workforce replaces headcount

Agents do: research & enrichment, drafting at volume, runtime personalization, and plumbing between systems. Humans keep: strategy & judgment, approval gates on anything touching money or contracts, closing, and taste. Everything else is not a person.

Technology & AI development, owned in-house.

The stack, the integrations, the data, and — above all — attribution are led from inside O/U+. Frank Filippi leads tech development; Jordan McCrary leads AI development. Build partners deliver against their specs, and the asset stays with O/U+.

Tech development
Frank Filippi
Technology leadership via PsyCray. Owns the platform build and every integration — agent ↔ CRM ↔ growth platforms ↔ sportsbook postbacks ↔ warehouse — plus the data & identity model, so a "lead" means one thing everywhere.
LinkedIn
AI development
Jordan McCrary
Owns the conversational engine behind the VBA — prompts, evals and drift monitoring — the avatar experience, and the personalization and model work that make the ambassador improve with every conversation.
LinkedIn
What in-house ownership buys
Attribution & CAC as one source of truth, reporting to O/U+ rather than to any supplier. Partner work is specified and graded against SLAs. O/U+ owns the VBA's logic, credentials and data — and the stack stays swappable as tools change.
The role we're recruiting

An operations leader — day-to-day execution across venues, partners, and the member funnel. Recruited against the launch and funded in the raise; until then the founder carries it with the agentic stack underneath.

The work we never have to build or staff.

Four partners carry the pieces that would otherwise be a licensing regime, a balance-sheet risk, a state-by-state legal calendar, or an audience we'd have to buy. Each one removes a function O/U+ would have to hire for.

In hand
Exchange · Creators · Venues
WagerWire's marketplace + licensing; the anchor creator network; teams, venues & bar distribution.
In talks
Payments & crypto rails
Friction-light deposits, faster payouts, a second commission stream.
Targets
Prediction · Data · Compliance
Event-contract venues, official sports-data providers, and geo/KYC/responsible-gaming infrastructure.
The eighth partner — the one on the critical path

A specialist AI build partner (Biz4Group) delivers the Virtual Betting Ambassador — phased deliberately, QR/website first, native app later, so launch never waits on an app-store cycle. Three things hold it: contractual ownership (prompts, workflows, credentials, data assign to O/U+), open connectivity (MCP keeps the agent layer swappable, not welded in), and a counterparty who can grade it — tech development leadership, on our payroll, from Day 1. If the build slips, the free-to-play front door and venue motion still generate onboards on a degraded agent.

Partner risk we own — stated, not waved away

Outsourcing the machinery is efficient but creates dependency. Prediction-market legal status is actively contested (a counsel-dependent upside, never the base case), and CPA revenue depends on sportsbook postbacks firing correctly. Partners carry the risk; we carry the responsibility for verifying them — which is precisely what tech development leadership is funded to do.

The stack that replaces a department.

In 2026 the ad platforms have absorbed targeting, bidding, and optimization — so money and attention go to creative volume, a clean data backbone, and an agent layer that runs the ops. Nothing needs an engineering department; a few pieces need one technical owner.

The product front door
The VBA stands up first as a QR-launched web experience (scan → chat → onboard, zero download friction at the bar), then as a native app once the base justifies it. O/U+ owns the guts contractually.
Acquisition & community
Paid-heavy on every platform that permits betting promotion, paired with community-native distribution (Whop, Discord) where high-intent bettors already gather. The free-to-play front door is what keeps us advertisable.
Lifecycle & CRM
Email-primary + web push now, native push at app launch, voice via the VBA — SMS modeled at zero until a gambling-tolerant carrier relationship exists. Consumer profiles live in the owned warehouse (BigQuery + RudderStack + RedTrack core), never a partner's.
The data backbone — the flywheel
Postback fires → warehouse matches → a live "funded bettor" segment builds itself → activation syncs to the ad platforms → CAC falls. Each turn makes the next customer cheaper and the owned dataset more valuable.
The whole stack, one number

Acquisition, lifecycle, agentic ops, data backbone, compliance, and B2B GTM land the software floor around $1.8–2.8K/month — the entire "operating department," rented not hired, and fully swappable. The three growth capabilities (audience intelligence, automated GTM, data monetization) are licensed separately — no single point of failure, no supplier grading its own performance.

Constraint 1
Prize structure
Non-cash free-to-play, each promotion under the $5K threshold — broadly advertisable, no gambling certification. Any change routes through gaming counsel first.
Constraint 2
Channel access
Every platform that lets us promote requires approval — the free-to-play front door is what unlocks them.
Constraint 3
Postback proof
One validated end-to-end test conversion — tech development's first deliverable — gates all acquisition spend.

What the first 90 days of capital buys.

First 30 days · De-risk & decide
Lock the prize structure with gaming counsel · tech leadership audits the build partner and locks IP/data · secure channel access (ad-platform certification + community) · stand up the data backbone core and validate one test conversion through the chained WagerWire postback.
Days 30–60 · Wire the machine
Turn on the agentic ops layer — agents + automation glue; build the ops cockpit · stand up acquisition — platform-native AI campaigns, AI creative, landing page, lifecycle · wire attribution — server-side tagging + Conversions API · contract the named stack; open the B2B venue pipeline.
Days 60–90 · Prove & compound
Run the Chicago paid pilot — validate cost-per-onboard & free-to-funded conversion · close the flywheel — first funded-bettor seeds into lookalikes · advance Second-Half partners — prediction-market & payments conversations · convert the tech owner to full-time at/into the launch raise.
The one-sentence version: a lean leadership core, an agentic stack that does the work of a department, Partners who carry the licensing, inventory, and audience — and owned technology leadership that makes sure it all works and that we, not our partners, own the truth.

The GTM plan is the promise. This is the proof it can be kept.

The GTM plan commits to……and the operating model is why that's achievable
A 20,000-profile base in 60 days, 6,000 funded by Month 8 — on a team of twoThe agentic stack does the work of an ops + ad-ops + lifecycle + analyst department at a ~$2–3K/mo software floor. The ~$45–60K/mo of payroll we don't carry becomes the media budget that buys those onboards.
Two funnels in parallel — B2C consumer and B2B venue/partnerPlatform pillars carry both motions on one data backbone — which is why two motions don't require two teams.
Activation deferred to Month 3 — Months 1–2 are a deliberate asset buildRevenue arrives in Month 3, so the data backbone must be wired inside the first 60 days with no revenue yet to justify it — precisely why technology leadership is a Day-1 engagement.
Illinois → Ohio → North Carolina, sequenced by handle × bar densityWagerWire's licenses across all 35 legal states mean the map is sequenced purely by venue economics. Licensing is a launchpad, not a gate; prediction markets extend the front door to all 50.
$107 / $75 / $32 unit economics per activationUnprovable unless the sportsbook postback fires. Constraint 3 gates all acquisition spend on one validated end-to-end test conversion — tech development's first deliverable.
A data-monetization line as the second revenue streamThe clean room sits inside the warehouse we already run. The binding constraint isn't technology, it's consent captured at the QR — a Month-1 design decision that cannot be retrofitted later.
Chicago validated, then replicated into 15+ venues and chainsPartners supply warm foot traffic we never bought; the automated-GTM platform runs the venue pipeline so replication doesn't require a BD headcount per market.

Cost, revenue, breakeven — and what happens after.

Cumulative revenue against cumulative program cost across three years, on the GTM model's unit economics ($107 / $75 / $32) and the real sports calendar. The first eighteen months are the proving ground; the profit curve is a Year-3 story, when national scale and the platform layer land on a base that's already built. Directional, not a forecast.

Cumulative revenue, cost & profit · Months 1–36
RevenueProgram costCumulative profit
$0 $10M $20M $30M CASH-FLOW-POSITIVE · M6 CUMULATIVE BREAKEVEN · M~17 YEAR 3 · NATIONAL + PLATFORM LAYER $34.0M REVENUE $23.9M COST $10.2M PROFIT M1 · Sep '26 M12 M18 · Feb '28 M25 M36 · Aug '29
▲ $500K MVP    ▲ $1.5M Launch    ▲ $1M Offseason    ▲ $2M Full Season — each capital tranche priced on the proof delivered by the one before it
How profitability grows — contribution by stage
Launch · M3–8
$192K
Flywheel · M9–18
$704K
Scale · M19–36
$9.3M
Each stage is funded by the proof of the one before it — the step change comes when national rollout and the platform layer land on a member base that is already paid for.
M6
First cash-flow-positive month — Super Bowl LXI, five months after kickoff
M~17
Cumulative breakeven, fully loaded — the second season's playoff run
$10.2M
Cumulative 3-year profit on $34.0M revenue
30%
Net margin held constant across every phase of the model
PhaseRegistrationsActivationsRevenue− Program cost= Contribution
Months 1–2 · MVP — free adoptionbuilding base0$0build + pilot$0
Months 3–8 · Launch — activate20,0006,000$642K$450K$192K
Months 9–18 · flywheel (~6%/mo)73,50022,000$2.35M$1.65M$704K
Months 19–36 · national + platform layer966,500290,000$31.0M$21.8M$9.3M
3-year arc1.06M318,000$34.0M$23.9M$10.2M
The raise behind it: $500K MVP (Sep–Oct '26) → $1.5M Launch (Nov '26–Apr '27) → $1M Offseason → $2M Full Season — ~$5M across the arc. Basis: GTM Investor Deck v10 unit economics; operating overhead at $20K/mo human layer + ~$2.5K/mo software (rising as technology and AI development scale from Season 2). Seasonality follows the sports calendar — peak months are not annualized. These figures are projections, not guarantees — they depend on unvalidated conversion assumptions and actual results may differ materially.

Asked the way a sophisticated investor would ask them.

We ran an adversarial review of our own plan before writing this. Where the honest answer is "we don't know yet," that is the answer.

Q · Is the $75 cost fully loaded?
Inside it. The $75 carries acquisition, operations, and the cost of onboarding profiles that never activate. What we owe at diligence is the decomposition — and we're building it.
Q · Is the peak month your run rate?
No, and we won't present it as one. Handle collapses from spring to late summer; a blended annual figure is realistically 40–60% of peak months. The off-season is an explicitly funded tranche, not a buried assumption.
Q · Where does free-to-funded conversion come from?
It's an assumption — and the number most likely to be wrong. That's the entire reason Months 1–2 are a paid Chicago pilot before the launch budget locks: we buy the real conversion rate at small scale first, and resize the raise before committing the media, not after.
Q · Can a team this lean genuinely run this?
Yes — tech and AI development are led in-house, and we've named exactly where the model strains: security and PII first, then production edge cases, then cost at scale. Tech and AI development leadership sits ahead of that ceiling, and any agent touching money, contracts, or customer data has a human approval gate.
Q · Why do the sportsbooks need you?
We deliver what they can't buy programmatically: an in-person, venue-verified, 21+ bettor onboarded through a human moment plus an AI agent, at a point of intent no ad impression reaches. And the model doesn't depend on any single book's affiliate budget — if one cuts terms, the funnel re-points.
Q · What compounds as this scales?
The asset, not the code. A venue base already operating profitably, an owned first-party dataset collected at the point of highest intent with consent designed in, and a loop where every funded bettor makes the next one cheaper. Three years of venue operations and a consented member base can't be bought off the shelf or collected retroactively — so the lead widens with every month the engine runs.
Contact  Ed Berry · ed@overunderchicago.com