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u/imjp 6 days ago How Do I?

12 years running a B2B company in the Caribbean, ~$1.6M ARR, and I've never had a mentor. How did you find yours?

I've run a fleet tracking company for about 12 years. We sell GPS tracking and AI dashcams to commercial fleets, mostly across the Caribbean, with a smaller operation in Colombia. We have around 370 clients, roughly $1.6M ARR, and we're on track for about 30% growth in the Caribbean this year. On paper it's going fine. But I've reached the point where I don't fully trust my own read on the business anymore. I built most of it by figuring things out as I went, and I'm starting to suspect some of what I see as normal is actually a blind spot. Here's a concrete example. Almost half our clients, about 170 of 370, pay late. They don't default, they're just consistently late. We get paid by wire transfer because that's how most businesses in the region pay, and we bill across 20+ territories with different banks and payment habits. I've lived with this for so long that I honestly can't tell anymore whether it's just the market or something I've been tolerating that a more experienced operator would have fixed years ago. I suspect it's the second. That's the kind of outside perspective I'm looking for. I want someone who has been further down the road and can look at what I'm doing and tell me what I'm not seeing. A few questions for anyone who's been here: 1. Mentor or coach? I don't know if I need a founder who's done it, a paid coach, or both. If you've had both, what did each give you that the other couldn't? 2. How did you find yours? And if it was someone senior who didn't owe you anything, how did you make the ask? 3. Has anyone dealt with late payments in a market where wire transfer is the default? What actually changed client behavior? 4. Looking at my situation from the outside, what would you be asking me? I'm not selling anything and I'd rather not get coaching pitches in my DMs. I'm just trying to learn from people who've been in this spot. Happy to answer questions about selling B2B in the Caribbean if that's useful to anyone.
2 comments held Reddit says 1 on reddit ↗
  1. u/AutoModerator moderator pinned 1 6 days ago
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  2. u/TennisSkirt1628 1 6 days ago
    Has anyone dealt with late payments in a market where wire transfer is the default? What actually changed client behavior?
    How late are we talking? What percentage of it is aging past thirty days?