The ride-along that uncovers everything

Lesson 3 of 12 · 8 min read

Spend a full day on the route before closing. You'll learn things no spreadsheet shows, and you'll catch problems that would have cost you in month two.

What to test on a ride-along:

- Real drive times between stops. Often longer than advertised, especially in summer traffic. Measure with the seller's actual vehicle on the actual day of the week.
- Gate codes and access. How many work first-try? How many require texting the homeowner? How many have a dog you have to navigate?
- Seller-customer rapport. Which customers are home and friendly vs distant? Which ones come outside to chat (those are sticky), which ones avoid contact (those are flight risks)?
- Time per stop. A "10-minute stop" that's actually 18 minutes destroys daily capacity math. Time 5–10 stops with a stopwatch.
- Equipment condition at the pad. Note pump models, age, filter condition, automation systems. You're not just inspecting, you're building a 12-month repair-conversation list.
- Chemical inventory and usage. Does the seller carry a real working stock or restock daily from the supply house? Consumption per pool tells you about chlorine demand, stabilizer levels, and whether the route is truly low-touch.
- Truck condition under load. Brake feel, A/C function, suspension on rough roads, cargo organization. Pop the hood. Ask about recent repairs.
- Tech tool use. Are they actually logging service in the CRM at every stop, or filling it out at the end of the day from memory? The latter means the data quality is lower than it appears.

Things to ask the seller while driving:

- "Which customer surprised you the most this year, good or bad?"
- "Which stop do you dread, and why?"
- "Which one is your favorite, and why?"
- "What's the one thing that would make this route 20% easier?"
- "Who's your backup if you break your arm tomorrow?"

You're getting honest stories at 35 mph that you'd never get in a meeting room.

Run the route twice if you can. Once with the seller driving (you observe), once with you driving (they coach). The second pass reveals whether you can actually do the work, physically, technically, and emotionally, at the pace the route demands.

Ride-along etiquette. Bring water, bring snacks, dress for outdoor work, leave the watch and the suit. If the seller works a 7-hour day, do the full 7. Anything less and you don't have data.

The ride-along is the single highest-ROI hour you'll spend in due diligence. Don't skip it, don't shorten it, and don't accept "I'll just send you a video."

Quick check

1. Why ride along on a typical day, not the seller's best?
2. What should you secretly time on a ride-along?
3. What customer interactions reveal the most?
4. Equipment-related signal to watch for?
5. How many days should you ride before LOI on a meaningful deal?
6. Order what to observe on a diligence ride-along.
  1. 1Time on each pool
  2. 2Tech-customer interactions
  3. 3Drive time between stops
  4. 4Equipment condition & inventory
7. If the seller insists on doing the ride-along themselves rather than the regular tech, that's a green flag.
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