Prepared for today's working session

The next golf platform isn't a product. It's an operating system.

Sixty days of independent, evidence-led discovery to convert founder conviction into investable evidence — TAM, ICP pull, willingness-to-pay, competitive moat, capital path. Built for the way Dale Ventures already wins.

John Osberg Primary Consultant · ex-PGA of America, OnCore Golf
Steve Coulton Primary Consultant · Coulton Ventures, ex-OnCore Golf
2:00PM ET · TODAY
With
Jon Varley · ArcStone / Moneta · advising Dale Ventures
Working session Discovery review & sync · 60 min
The market we're moving into

Eight straight years of growth. On 2,000 fewer courses.

Demand has outrun the tools. The category leaders are running 2008-era software. That's the opening.

0M
U.S. Golfers · 2025
All-time high. Up 55% in a decade.
+55% / 10Y
0B
U.S. Economic Impact
$102B direct industry size.
+22% / 5Y
0
Global Golfers
148 countries. 18,500 courses.
2026
+58%
Juniors since 2019
~6M juniors on-course in 2025, most since 2004. 35% are girls.
+46%
Women since 2019
8M+ women now play on-course. Net gain of 2.5M in six years.
+73%
Simulator golf since 2019
19M Americans play off-course only. Topgolf, xGolf — the new front door.
Market sizing · working hypothesis

A $2B market. A $500M U.S. opportunity. A $25M ARR beachhead, in three years.

These bands are deliberately wide. Narrowing them — and naming the segment that gets CaddieOS to the high end of SOM fastest — is what the 60 days are for.

TAM
$2.5B
SAM
$500M
SOM
$25M
TAM
Global golf operations softwareTee sheet, POS, member mgmt, agronomy, F&B, instruction, retail. 7–10% CAGR.
$1.5–2.5B
SAM
U.S. private, resort, upper-tier daily-fee~16,000 U.S. courses × $8–25K ARR, plus ClubCorp / Troon / KemperSports / Invited.
$300–500M
SOM
3-year beachhead capture2–5% SAM penetration. Benchmarked to Toast, Lightspeed, Mindbody at comparable maturity.
$6–25M ARR
Competitive landscape

Everyone's solving a slice. Nobody owns the operator's day.

Player-side data, range-and-sim hardware, marketplace tee-times — the category's fragmented along the surface a vendor happens to touch. The whitespace is the operating layer that connects them.

OPERATOR DEPTH → PLATFORM BREADTH → PLAYER POINT TOOLS PLATFORM OPPORTUNITY OPERATOR POINT TOOLS OPERATOR STACK Arccos Trackman Foresight GolfNow Topgolf Legacy POS Tee Sheet CaddieOS target xGolf Dale portfolio
Player-side ←
→ Operator-side
Adjacent / point tools
Legacy operator software
Dale portfolio (xGolf)
CaddieOS — operating layer
The 60-day shape

Four parallel workstreams. One synthesis. Decision-quality evidence.

Independent. Evidence-led. Time-boxed. Every recommendation traces back to interview data, market analysis, or competitive benchmarking — not opinion.

A
WORKSTREAM A
Module Assessment
Lead: Steve
Structured teardown of the existing CaddieOS module set against real operator workflows. Keep, cut, expand — scored on operational value, technical maturity, defensibility, effort-to-finish.
B
WORKSTREAM B
Primary Research
Lead: John
~20 interviews across PGA pros, shop owners, superintendents, GMs, COOs, multi-course operators. Every guide closes with willingness-to-pay testing against three live price models.
C
WORKSTREAM C
Competitive & Market
Lead: John, with Steve on technical
Feature-parity matrix, install-base scan, funding posture. Bottoms-up TAM/SAM/SOM. Adjacent integration pressure points and partnership candidates.
D
WORKSTREAM D
Synthesis
Lead: Joint
Module keep/cut/expand. Named beachhead. Pricing hypothesis with A/B/C test results. Build-vs-partner-vs-buy on every adjacent capability. 12-month roadmap.
Our competitive advantage

This proposal — and this site — were built by an AI agent harness.

John and Steve don't just bring 20 years of golf operator relationships to this engagement. We bring leverage. The proposal you read last week, the engagement plan, this lander, the comp landscape work — all of it ran through our agent harness. Senior partners thinking with senior tools.

  • 5–10× faster. Discovery work that takes a typical advisory shop a month, we ship in days. The same analytical depth.
  • Evidence-grade. Every claim traceable. Every source cited. Adversarial verification before anything ships to you.
  • Live, not static. The deliverable is a living document. Dale asks a follow-on question on day 75; we answer in hours, not weeks.
  • Scoped to senior judgment. The model doesn't decide. We do. The tool sharpens our reach; it doesn't replace the work.
ross · caddieos-discovery · live
→ agent.workflow("competitive-scan")
fan-out: 7 finders · 3 verifiers per claim
✓ Trackman · Arccos · Foresight · GolfNow · xGolf
✓ 41 sources read · 12 cross-verified
emitted: comp_matrix_v3.json (42 fields)
→ agent.workflow("market-sizing")
3 independent triangulations
✓ TAM/SAM/SOM bounds + confidence
→ agent.workflow("lander-prep")
draft → review → humanize → render
✓ shipped · 2026-06-23 11:00am ET
→ ready
Today, 2:00 PM ET

What we'd like to cover.

A working session, not a pitch. We're here to surface the right shape — and the right questions — together.

01
Calibrate roles & lens
Confirm Jon's hat on this — capital-markets advisor to Dale-Canada, or broader. Aligns how we'd frame the deliverable.
~10 min
02
Walk the 60-day shape
Four workstreams, deliverables at day 60, pricing-tested by primary data, named beachhead.
~15 min
03
CaddieOS next to xGolf
Dale already has conviction in golf-tech (xGolf ME). CaddieOS as the operator-layer adjacent to an operator-format brand.
~10 min
04
The capital-markets read
What would discovery need to surface for Jon to bring this to his institutional network with conviction? Comparable exits, defensibility, TAM, ICP.
~15 min
05
Next steps & deciders
Who at Dale needs to be comfortable with the scope. Path to signature. Kickoff timing.
~10 min
Your consultants

Operators first. Sellers second. Senior across both.

Twenty-plus years of distribution, partnership, and capital work across U.S. golf. The operator-and-investor network this engagement actually needs.

JO
John Osberg
Primary Consultant · WORKSTREAM B + C LEAD
A decade building distribution, partnership, and revenue engines across U.S. golf. At PGA of America: 60+ brand-partnership portfolio (Michelob Ultra, Club Car, Oakley, Tito's, Ralph Lauren RLX, Corebridge), $250K+ annual partnership revenue, scaled the PGA veteran program to $220K+ annual funding. Prior: Director at OnCore Golf, $3.5M+ in distribution revenue across national retail and golf-specialty channels.
PGA of America
OnCore Golf
50+ events
Partnership build
SC
Steve Coulton
Primary Consultant · WORKSTREAM A LEAD
Co-founder & VP Sales at OnCore Golf — scaled to ~$5M ARR at exit, raised $2M+ in early capital, $20M+ cap base (Charles Schwab among backers). Built a 30+ rep sales network, DICK'S / Golf Galaxy + Wegmans national distribution ($2M+ big-box revenue). Structured PGA Tour / LPGA / LIV ambassador relationships. Today: founder, Coulton Ventures. Prior: Deutsche Bank Commercial Paper Trading. NYU Econ, Men's Varsity Golf.
Coulton Ventures
OnCore Golf
Deutsche Bank
Capital + sales
The ask, plainly

Sixty days. One named beachhead. The evidence to deploy capital with conviction — or not.

The cheapest way for Dale to earn conviction before the next capital cycle. The cleanest way for CaddieOS to be ready when that cycle opens. We're excited to walk it with you.

John Osberg · johnosberg@gmail.com
Steve Coulton · coultonventures@gmail.com
Today · 2:00 PM ET