What's really going on

You've got two pipelines that touch the same deal: the investing side sources, the DSCR brokerage funds. That handoff is where deals leak, not in the CRM UI. You're pricing seats before you've decided who owns a lead at which stage, and you're shopping for ISAs before the pipeline they'd work in exists on paper. Pipedrive at $80/seat is their top tier — you don't need that tier. HubSpot's free plan has no permissions because it's built for one shared team, not two entities.

What to do instead

1. Pipedrive, ~$14-15/user/mo entry tier — use one account, two pipelines (Investing / DSCR), custom fields to tag the handoff. Skip the $80 tier; you don't need it until you're actually sending LOIs at volume.
2. Airtable, free to ~$20/user/mo — build the LOI and PSA generator here with a form + document automation. Cheaper and more flexible than paying Pipedrive's top tier for docs.
3. Habit: every deal that crosses from investing to brokerage gets a written handoff note in the CRM before anyone touches it. No note, no handoff.

Today, in the next 30 minutes: open Pipedrive's trial, create two pipelines named exactly after your two businesses, and drag your last five deals into the right stages. You'll see the leak.

What you're being oversold

HubSpot's $760/mo jump is the classic free-to-Sales-Hub upsell — you're being pushed there because of the permissions gap, not because you need sequences or forecasting. Ignore Outreach, Salesloft, Apollo — those are for 20+ person outbound orgs, not a founder hiring their first ISAs. Doing nothing costs you the deals that fall between your two entities: the investing lead that didn't get offered DSCR, the DSCR inquiry that had an investing angle nobody noticed.

When to revisit this

When you've actually hired ISA #2 and they're stepping on each other's leads — that's the permissions moment, not before.

The part worth getting right

The one call: are your two businesses one pipeline with a stage-gate, or two pipelines with a formal handoff? If the same person often works both sides of a deal, it's one pipeline with a "convert to DSCR" stage — Pipedrive entry tier handles it. If the investing team and brokerage team are truly separate humans with separate comp, it's two pipelines with permissions — and that changes the tool, the seat count, and whether you need paid HubSpot at all. Get this wrong and you'll migrate CRMs inside a year, right when you're onboarding ISAs.