8. If I Were You: The Next 90 Days
The single most important thing
Find out, within 45 days, whether landscaping owners will pay to have their DQ files built and kept. Get 5 firms paying at least $49 a month for a hands-on service before you write product code.
- Segment: US landscaping, lawn and tree firms with 3–25 trucks or truck-and-trailer combinations over 10,001 lb, mostly non-CDL, in 3 states you can reach.
- Job: "Tell me what DOT actually needs from us, build every driver's file, and keep the medical cards and annual reviews from lapsing, without me chasing paper."
- How: a concierge MVP. Send each driver an e-sign form and a photo-upload link, build the files in Airtable, email the owner a gap list and a monthly "due in 60 days" list, and hand over a PDF binder. Charge from week 1. Automate only what you've done by hand at least 20 times.
Timing: today is 30 Sept 2026. October to January is the landscaping quiet season. Owners have time for admin, and the pitch is "get ready before spring hiring". Conversion should peak in February to April. Plan for a slow first month and a busy spring.
The plan runs in two versions. Full-time is about 40+ hrs/week. ~15 hrs/week is the same plan with the milestones stretched. The ~15 hrs/week budget is: 6 hours of live calls with US owners, 6 hours of build, 3 hours of content and automation.
Week by week
| Weeks (full-time) | Weeks (~15 hrs/week) | Goal | Exit criteria |
|---|---|---|---|
| 1–2 | 1–3 | Advisor and discovery. Sign a paid DOT compliance advisor. Pull 300 firms from the FMCSA census: private-only, 3–25 power units, landscaping, lawn or tree in the name, in 3 states (query). Contact one state landscape association and 3 commercial-auto insurance agents. Interview 25 owners (12 at ~15 hrs/week). Ask: do you keep DQ files, when does each driver's medical card expire, how many drivers do you hire each spring, has DOT or your insurer ever asked for these records, and what happened? | You can write the top 3 triggers (audit, roadside, insurer, hiring) in owners' own words. You know what share of owners know the 10,001 lb rule. |
| 3–4 | 4–6 | Concierge pilot. Offer 8–10 firms a done-for-you catch-up and upkeep: driver links, gap list, file building, monthly due list, binder. Charge $49–119/month plus $149 catch-up. | Day 45 kill test: 5 firms paying (3 at ~15 hrs/week). If fewer than 3 will pay, the pain isn't felt. Switch to HVAC and plumbing once, then stop. |
| 5–8 | 7–13 | Build the thin v1 (web + mobile web): "does DOT apply to me?" checker, drivers and documents, driver text link with OCR expiry dates, e-signed application, expiry engine with owner and driver reminders, § 391.25 review signed on a phone, catch-up gap list, binder PDF, retention log, Stripe billing. Advisor signs off every rule and template. | Pilots move from Airtable to the app. Every pilot firm has 100% complete files for active drivers and zero expired medical cards. |
| 9–10 | 14–16 | Free hook and channels. Publish the checker and 10 SEO pages ("DOT number for a landscaping trailer", "medical card for a non-CDL driver", "DQ file checklist for landscapers", by state). A recorded 8-minute demo. Personal outreach to 20 census firms a week, quoting their own census data. | 100+ checker uses and 5+ trial requests from search, the association or agents. |
| 11–12 | 17–20 | Measure and decide. | 15 firms paying on the app (8 at ~15 hrs/week), zero missed reminders, and a measured outcome per firm (files from X% to 100% complete). Hit: continue to the roadmap. Miss: back to discovery, or Pivot A or B. |
At ~15 hrs/week the plan takes about 20 weeks, not 12. That lands the product just before spring hiring, which is the right moment. The gates in WHAT-TO-DO-AND-AVOID.md already account for that.
Automation from day one (what keeps the hours low)
- Booking links for owner calls, with a 5-question intake form (trucks, trailers, drivers, CDLs, states).
- Driver links and e-sign templates set up once and reused per firm.
- An automated "due in the next 60 days" email per firm on the 1st of each month.
- A catch-up checklist and column-mapping sheet. Every catch-up you do by hand becomes the spec for the guided import.
- A recorded demo on sample data, sent before every call.
- One weekly office-hours call for all pilot firms.
Kill criteria (write these down now)
At day 45 (week 6 at ~15 hrs/week):
- fewer than 5 firms paying (3 at ~15 hrs/week), after 25 (12) owner calls: switch trade once, then stop.
At day 90 (week 20 at ~15 hrs/week):
- fewer than 8 firms paying, or
- any pilot firm has an active driver with an expired medical card that the product didn't flag.
Then the wedge or the product is wrong. Don't respond by adding features. Respond by changing the trade, the trigger you sell on, or the channel.
The one thing to stop doing
Stop thinking of this as trucking software.
Every Clearinghouse screen, ELD integration and "for owner-operators" landing page aims at the segment where customers disappear and tools cost $15. It feels like the bigger market, because it is, but it's the crowded one. A close second: stop planning marketplace integrations before 10 firms have paid.
What stays on the long-term roadmap (only after proof)
- Vehicles: maintenance due dates, the annual inspection, defect reports with repair certification.
- MVR ordering through a licensed vendor, and the insurer pack.
- Spring hiring mode and Spanish-language driver screens.
- A second trade: HVAC, plumbing and electrical.
- CDL add-on for mixed fleets (Clearinghouse reminders, test-result storage).
- Field-service app marketplaces (Jobber, ServiceTitan, LMN, Aspire), then Samsara and Geotab listings.
- White-label for insurance agents and safety consultants.