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Work with the AI coaches

Re:InvestorHub gives you three AI coaches, each focused on a different part of investing. You can start a conversation with any of them at any time, and you'll also run into them at specific moments as you analyze and work a deal.

Meet the coaches

Coach Specialty
Lenny the Lender Mortgages, Hard Money & Creative Financing
Sid the Project Manager Project Management, Contractor Vetting & Rehab Budgeting
Annie the Agent Market Analysis, Negotiations & Deal Finding

Lenny the Lender is your financing coach. Ask him about loan options, comparing rates, DSCR and portfolio loans, or creative financing strategies for a deal.

Sid the Project Manager is your construction and rehab expert. Ask him to help scope a job, vet a contractor, or build a realistic rehab budget.

Annie the Agent is your real estate market expert. Ask her about reading a market, running your ARV, finding deals, or how to approach a negotiation.

Start a conversation

Lenny's chat window docked open, with the conversation area and the Ask Lenny message box

  1. Select AI Coach in the left navigation. (From the dashboard, you can also use the Ask AI Coach shortcut in the header, which opens the same page.)
  2. Under Choose Your AI Coach, review each coach's specialty, then select Chat with Lenny, Chat with Sid, or Chat with Annie.
  3. The coach's chat window opens with a short greeting. Type your question and send it.

The Choose Your AI Coach section of the AI Coach page, showing the Lenny the Lender, Sid the Project Manager, and Annie the Agent cards with their specialty badges and Chat with buttons

What you should see

On desktop, the coach's chat window opens docked in the bottom-right corner of the screen, so you can keep working on the page behind it. On mobile, it opens as a sheet from the bottom of the screen.

Tip

In the chat window's header, the pop-out icon opens the conversation in its own separate window, and the minimize button collapses it without closing it. Both are handy if you want to keep chatting while you work elsewhere in Re:InvestorHub.

Where you'll run into a coach elsewhere

You don't only get to the coaches from the AI Coach page. They show up in context in a few other places:

  • Deal Analyzer results. After you analyze a deal, if the score comes back on the lower end, Deal Analyzer can show a short note from one or more coaches, right below the score, addressing a specific concern with that deal, labeled Annie says, Lenny says, or Sid says depending on which coach is speaking to it. See Deal Score for how to read the score itself.
  • Deal Analyzer, while filling out a deal. If required fields are still missing, you may see a prompt like Ask Annie where to find these, which opens a conversation with that question already filled in.
  • Deal Pipeline cards. At certain stages, a card can show a contextual prompt, such as Ask Annie on a deal that's Under Contract with closing questions, or Ask Lenny on a fresh offer with financing questions.

In each of these cases, selecting the prompt opens the relevant coach's chat window with your question already started.

Both plans include all three AI coaches; how much you can use them differs by plan. See Plans and what's included for what's included with Silver and Gold.