Club Caddie
👤 Jason Pearsall (Attorney, golf-course owner, and repeat golf-tech founder — he sold Golfler for $4.2M in 2017, then built Club Caddie.)🌐 siteLinkedIn
A golf-course owner got tired of running his club on a dozen apps that never talked, so he built the one that did.
Will it work? · our read
Insider advantage. The all-in-one pitch is easy to copy; a founder who owns courses and already sold a golf-tech exit is not. And most of the 20x scale came only after Constellation bought in.
01How the money moves
Course signs up: POS, tee sheet, members, F&B in one system
→
Pays about $15K a year on subscription
→
600+ courses = about $9M recurring ARR
02The numbers
$9M ARRStated2025, founder-stated
2025-12
All figures founder-stated on Nathan Latka's podcast, Dec 2025. podcast episode
$9M ARR (2025, founder-stated on podcast)
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You have the verdict. Members get the work behind it.
- The CENTS scorecard — where it's strong, where it's soft
- The founder's key move, and the counter-move
- How it could die — the evidence, and how sure we are
- The case against our own call
- A 🚀 launchpad prompt — the case, as a plan for your business
We rate our own confidence — and argue against ourselves. Nobody else in this category does.
Sources always public on all 560 cases · cancel anytime · 14-day refund
See a full teardown, free → ImportYetiSourcesSources last checked 25 August 2026
Nathan Latka podcast — 'From $450K to $9M ARR in 5 Years', founder-stated numbers (Dec 3, 2025)Jonas Software acquires Club Caddie Inc. (Feb 10, 2020)Club Caddie — About (product, Jonas/Constellation ownership)ShoutOut interview — Pearsall background, Golfler $4.2M exitgetLatka — Club Caddie $9M ARR, $11.6M valuation (self-reported, unaudited)
Revenue is first-party but self-reported: $9M ARR, 600+ courses, about $15K ACV, and the $600K raised were all stated by founder Jason Pearsall on Nathan Latka's podcast (Dec 3, 2025). Latka's own getLatka tracker lists $9M ARR / $11.6M valuation, but other third-party estimators (e.g. Kona Equity) peg revenue nearer $4.1M, so figures are unaudited. The '$450K to $9M in 5 years' arc spans 2020-2025 — i.e. mostly AFTER Jonas Software (a Constellation company) acquired Club Caddie in Feb 2020 — so 'bootstrapped' is only partly true: it raised $600K, then scaled with an acquirer's resources under a long-term earnout. Founding year (about 2019) is approximate; development began around 2017. The Golfler exit ($4.2M to Supreme Golf, 2017) is founder-stated. No drama was invented — the acquisition and earnout are documented. We never score you.