FleetFile

Why a ladder instead of one target

This idea is assessed at six MRR levels, not one fixed target. Compliance software for small fleets has skewed outcomes. Most small tools stall at a few dozen customers. A few, like Whip Around, grow by moving up to mid-size fleets. One "$20k MRR" number hides the useful part: how likely each level is, and what each level costs in hours.

The anchor: there is no verified base rate

No verified base rate exists for bootstrapped B2B micro-SaaS. Nobody publishes "the share of new B2B micro-SaaS products that reach $X MRR within 24 months". The nearest proxies were collected for TradeLedger (../../tradeledger/research/10) and weren't re-checked here:

• RevenueCat 2026, Business-category apps: 14.7% reach $1k a month, 1.6% reach $10k, within 2 years. These are app-store products.
• ChartMogul 2025: 13.4% of companies reach $1M ARR within 3 years of first revenue. The clock starts later and the bar is far higher.

The odds below are judgment estimates, anchored loosely to those proxies and to what the research found for this idea.

Three things push the odds up:

• The buyer list is public and complete. FMCSA's census lists every carrier, with fleet size, CDL count, phone and, for ~97% of small fleets, an email (10).
• The records are required by law and kept for years. A DQ file stays for 3 years after a driver leaves, so a firm that moves its files in rarely moves them out.
• Few customers are needed. At ~$85 a month, $10k MRR is ~118 firms out of ~60,900 interstate private fleets with 3–25 units.

Four things push them down:

• The buyer doesn't know the rule applies. You must teach the problem before you can sell the fix.
• The category is crowded at the bottom. At least 7 small DQ-file tools publish prices, most at $15–49 a month, and Motive and Samsara bundle DQ files.
• Liability. A missed medical card that ends in a crash puts your reminders in a lawsuit.
• Seasonality. Landscapers cut costs in winter.

Odds at each MRR level (reached by month 24)

The three alternative columns assume full-time work and the same conditions, so they're comparable with the right-hand column.

Notes on the alternatives:

• New and single-truck for-hire carriers are the biggest pool (226,152 single-truck interstate for-hire carriers). But they are the cheapest buyers, the most solicited, and the least likely to survive: 60–73% of new small for-hire registrations are gone within 3–5 years.
• Established for-hire carriers with 3–20 trucks are a real market and score close to the recommended version full-time. But they already have the most choice (J.J. Keller, Foley, Tenstreet, DQM Connect, Core Compliance, Motive and Samsara bundles), and they need Clearinghouse and drug-testing workflows on day one. It's the Pivot A option if trade fleets don't pay.
• Telematics-marketplace-only relies on Samsara and Geotab to bring customers. Samsara states no revenue share, can remove you without cause and sells DQ files itself. Geotab's DQ slot is held by DQM Connect. Both skew to larger fleets (10).

The recommended version (private trade fleets, landscaping first) is set out in WHAT-TO-DO-AND-AVOID.md. It assumes all 4 founder-only conditions:

• access to trade owners;
• a paid DOT compliance advisor, plus E&O insurance;
• 5 firms paying before building;
• hours per week stated honestly, with 6 of them in US business hours.

If owner access is missing, multiply the recommended odds by ~0.5. If any other condition is missing, multiply by ~0.7.

How to read the ladder

• $1k–3k (12–35 firms) is a realistic outcome if calls confirm that owners fear an audit or an insurer's demand.
• $5k–10k (59–118 firms) needs a repeatable channel: search, the free checker, an association, or insurance agents.
• $20k (~235 firms) is a stretch in 24 months. It needs full-time hours and usually a second trade.
• The two columns split most above $3k. The first 30 firms each need a call and a catch-up. At 15 hrs/week that caps new firms at ~3–4 a month in year 1.

Portfolio definitions (for comparison with other ideas)

• Tier A needs ~980 firms at $85, or a move up-market into Whip Around's and J.J. Keller's territory. It isn't the goal.
• Tier B sits just below the $20k rung. Margin (~87–89%, with MVRs passed through) isn't the problem. Profitability after a part-time support hire and winter cancellations are.

How this compares with the other ideas in this portfolio:

• Below TradeLedger at every level. Extinguisher shops know their records are required. Landscapers often don't.
• Similar to WaiverWorks and StoreComply, the other ideas that sell a legal record-keeping duty to small businesses.
• Its distinctive shape: a public, complete buyer list, but a buyer who must be taught the problem. Good odds at $1k, and a steep fall above $5k.

Fundable in current form?

No, and it doesn't need to be. A small-fleet compliance tool has a good-business ceiling. The venture-scale versions already exist: Samsara and Motive bundle compliance into telematics, and J.J. Keller sells it with services. See 06-fundability.md.

One-paragraph verdict

The catalog's evidence is real, but it points up-market. Whip Around's $10M comes from fleets with ~80–170 vehicles, not from 1–20 truck carriers. Small trucking carriers are the worst buyer here: they're numerous, cheap, heavily solicited, served by at least 7 small DQ tools and two telematics giants, and most of them are gone within 3–5 years. The better buyer is the one the catalog mentions second: landscaping, HVAC, plumbing and electrical firms whose trucks and trailers cross 10,001 lb. They owe DQ files, medical cards and annual MVR reviews but not drug testing, they rarely have anyone who knows it, and they stay in business. Build the driver text link, the expiry and annual-review engine, the catch-up and the audit binder, with a paid compliance advisor behind every rule. $1k–3k MRR is a reasonable expectation, $10k needs a channel that works without you, and $20k in 24 months is a stretch. If 5 firms won't pay by day 45, the problem isn't felt, and you should stop.