Conversation Review

Real Shadow Beta conversations — grade each AI Shadow turn.

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Chad Roebuck

Historical outboundOther

[Outbound message, no text]

Mar 18, 2026, 5:27:44 AM UTC
ProspectOther

Yes, please!

Mar 18, 2026, 5:29:58 AM UTC
Historical human replyOther

Ok great, what's the best email for you?

Mar 18, 2026, 5:29:59 AM UTC
Historical outboundOther

[Outbound message, 1 attachment, no text]

Mar 18, 2026, 5:40:00 PM UTC
ProspectOther

Chad@roebuckco.com

Mar 18, 2026, 5:40:52 PM UTC
Historical human replyOther

Saw you reached out to help with Sober Living, do you already have experience with real estate or looking to break into it?

Mar 18, 2026, 5:59:04 PM UTC
ProspectOther

no experience but have been looking into it for a bit now.

Mar 18, 2026, 6:09:49 PM UTC
Historical human replyOther

Ok cool, what's got you looking to break into Sober Living?

Mar 18, 2026, 6:26:53 PM UTC
ProspectOther

Perfect fishing hole to do the Lords work.

Mar 18, 2026, 6:39:33 PM UTC
Historical human replyOther

Can you elaborate?

Mar 18, 2026, 6:55:12 PM UTC
ProspectOther

I run a telecommunications business. I’m planning on a very good year and need to invest towards the end of the year in another business. Helping people and making money sounds good to me.

Mar 18, 2026, 7:08:02 PM UTC
Historical human replyOther

I gotchu

Mar 18, 2026, 7:23:51 PM UTC
Historical human replyOther

How much capital do you have set aside, liquid to invest into sober living and what's your credit score?

Mar 18, 2026, 7:23:57 PM UTC
ProspectOther

let me get back to you. thx

Mar 18, 2026, 7:33:56 PM UTC
Revenue AI — SHADOW (not sent)

Sounds good. Just so I know what to follow up on, is there something specific you're weighing?

Details

Primary intent: vague_or_unclear

Intent strength: medium

Objective: clarify_message

Objection type / stage:

Missing discovery context: Where they stand after the call with Josh — what's holding them back from moving forward

Discovery prompt:

Offer positioning: validate_fit_then_call

Execution route: constrained_llm

Qualification status: unknown

Disqualification reason:

Verdict
Automated/CRM messageEmail
Apr 24, 2026, 12:16:00 AM UTC
Automated/CRM messageEmail
May 12, 2026, 1:24:07 AM UTC
ProspectOther

Yo Andrew! I’m serious about getting into this in a few months. I made a lot of money this year building data centers and i need to write off a lot of bread. I’m figuring buying a couple of homes and starting the sober living

Jul 3, 2026, 1:58:39 AM UTC
Revenue AI — SHADOW (not sent)

Love it. What are you working with capital wise right now that you'd be putting toward this?

Details

Primary intent: interested_advancing

Intent strength: high

Objective: discover_context

Objection type / stage:

Missing discovery context: Specific liquid capital amount available to invest

Discovery prompt: How much do you have set aside right now to put toward this?

Offer positioning: validate_fit_then_call

Execution route: constrained_llm

Qualification status: unknown

Disqualification reason:

Verdict
Historical outboundOther

[Outbound message, no text]

Jul 3, 2026, 2:01:14 AM UTC
Historical human replyOther

Sure thing

Jul 3, 2026, 6:19:25 PM UTC
Historical human replyOther

Why don't we do this, are you open to meeting with one of my partners to show you everything I do in greater detail? If things make sense and you want to move forward he’ll help in building out your step-by-step plan to get started and connect you with me

Jul 3, 2026, 6:19:26 PM UTC
ProspectOther

Sounds good

Jul 3, 2026, 6:19:54 PM UTC
Revenue AI — SHADOW (not sent)

Love it. Before we set that up, how much do you have set aside right now to put toward this?

Details

Primary intent: scheduling_request

Intent strength: medium

Objective: discover_context

Objection type / stage:

Missing discovery context: How much liquid capital he has available to invest, as a specific number

Discovery prompt: How much do you have set aside right now to put toward this?

Offer positioning: validate_fit_then_call

Execution route: constrained_llm

Qualification status: unknown

Disqualification reason:

Verdict
Historical human replyOther

Let me know your email and phone no.?

Jul 3, 2026, 6:20:24 PM UTC
Historical human replyOther

What time zone are you in?

Jul 3, 2026, 6:20:29 PM UTC
ProspectOther

Chad@roebuckco. 8323024406 central

Jul 3, 2026, 6:20:55 PM UTC
Historical human replyOther

He can do 10am tomorrow or 2pm PT on Sunday, will be an hour long over Zoom, need you on a laptop with a pen and paper, let me know which one works best?

Jul 3, 2026, 6:22:20 PM UTC
ProspectOther

I can do 10 am tom.

Jul 3, 2026, 6:25:29 PM UTC
Automated/CRM messageEmail
Jul 3, 2026, 6:26:17 PM UTC
Automated/CRM messageSMS
Jul 3, 2026, 6:26:19 PM UTC
Historical outboundCall

[Outbound call, no transcript fetched]

Jul 3, 2026, 6:26:54 PM UTC
Historical human replyOther

Let me know once you get the invite?

Jul 3, 2026, 6:27:48 PM UTC
ProspectOther

I’m sorry i just realized i have a conflict with tomorrow at 10. i also run an electrical company and neither of those times is good with me. is there anything thursday and beyond next week?

Jul 3, 2026, 6:28:28 PM UTC
Historical human replySMS

Do you have the Zoom link for our call?

Jul 3, 2026, 6:28:40 PM UTC
Historical outboundEmail
Jul 3, 2026, 6:28:41 PM UTC
Historical human replyOther

Can you do Monday, 1pm or 8pm CST instead?

Jul 3, 2026, 6:29:05 PM UTC
Historical human replyOther

4pm is also open

Jul 3, 2026, 6:29:13 PM UTC
ProspectSMS

I do but just realized i have a conflict tom at 10. I also have a conflict with sunday at 2. Can we schedule for thursday next week?

Jul 3, 2026, 6:30:00 PM UTC
Historical human replySMS

💪💪 Pumped to talk with you! Just emailed you this link with a little more info to review before our zoom call. Please make sure you review before we connect: https://go.soberlivingriches.com/appt-confirmation

Jul 3, 2026, 6:30:04 PM UTC
Historical outboundEmail

Thanks for confirming your call with us! PS: And here's the quick video to watch before the call: https://go.soberlivingriches.com/appt-confirmation

Jul 3, 2026, 6:30:05 PM UTC
ProspectOther

thursday i will be available

Jul 3, 2026, 6:31:19 PM UTC
Historical human replyOther

How about, 10am or 4pm CST on Thursday?

Jul 3, 2026, 6:32:11 PM UTC
ProspectOther

Let’s do 4pm thursday

Jul 3, 2026, 6:32:34 PM UTC
Automated/CRM messageEmail
Jul 3, 2026, 6:33:04 PM UTC
Automated/CRM messageSMS
Jul 3, 2026, 6:33:05 PM UTC
ProspectOther

Sorry about that Andrew. i don’t want to waste your time. I also am very very busy person

Jul 3, 2026, 6:33:10 PM UTC
Automated/CRM messageOther
Jul 3, 2026, 6:33:10 PM UTC
Historical human replyOther

A deep-dive into the sober living business model: https://www.youtube.com/watch?v=oDLZLlHuQcg Sober Living Program Walkthrough - https://soberlivingriches.com/case-studies

Jul 3, 2026, 6:33:13 PM UTC
Historical human replyOther

No worries, I can understand

Jul 3, 2026, 6:33:21 PM UTC
ProspectOther

Thanks we will see you thursday at 4

Jul 3, 2026, 6:34:17 PM UTC
ProspectOther

Anyway we can add my partner to the call on thursday? His email is Jay@roebuckco.com

Jul 4, 2026, 8:19:26 PM UTC
Revenue AI — SHADOW (not sent)

I don't have a way to add him from my end, so I can't confirm that. Best bet is to bring it up with the advisor, or just have him join from the same Zoom link. See you Thursday at 4.

Details

Primary intent: question

Intent strength: medium

Objective: answer_question

Objection type / stage:

Missing discovery context: How much liquid capital they have available, with a specific number

Discovery prompt:

Offer positioning: validate_fit_then_call

Execution route: constrained_llm

Qualification status: unknown

Disqualification reason:

Verdict
Historical human replyOther

Absolutely, happy 4th of July!

Jul 4, 2026, 8:20:11 PM UTC
ProspectOther

Happy 4th. Thank you. See you guys thursday

Jul 4, 2026, 8:22:00 PM UTC
Revenue AI — SHADOW (not sent)

No reply drafted — routed to human_review instead.

Details

Primary intent: ready_to_confirm

Intent strength: medium

Objective: hold_for_human

Objection type / stage:

Missing discovery context: Their liquid capital and credit score as specific numbers

Discovery prompt:

Offer positioning: validate_fit_then_call

Execution route: human_review

Qualification status: unknown

Disqualification reason:

Verdict
Historical outboundEmail
Jul 6, 2026, 9:00:59 PM UTC
Historical outboundEmail
Jul 7, 2026, 1:01:25 AM UTC
Historical outboundEmail
Jul 7, 2026, 5:00:04 AM UTC
Historical outboundEmail
Jul 7, 2026, 11:02:40 AM UTC
Historical outboundEmail
Jul 7, 2026, 12:01:39 PM UTC
Historical outboundEmail
Jul 7, 2026, 3:01:44 PM UTC
Historical outboundEmail
Jul 7, 2026, 9:00:19 PM UTC
Historical outboundEmail
Jul 8, 2026, 1:00:32 AM UTC
Historical outboundEmail
Jul 8, 2026, 9:00:31 AM UTC
Automated/CRM messageSMS
Jul 8, 2026, 9:00:21 PM UTC
Historical human replySMS

Do you have the Zoom link for our call?

Jul 8, 2026, 9:02:25 PM UTC
Historical outboundEmail
Jul 8, 2026, 9:02:26 PM UTC
ProspectSMS

yes

Jul 8, 2026, 9:02:45 PM UTC
Historical outboundEmail
Jul 9, 2026, 1:00:02 AM UTC
Historical outboundEmail
Jul 9, 2026, 5:00:01 AM UTC
Historical outboundEmail
Jul 9, 2026, 9:01:12 AM UTC
Historical outboundEmail
Jul 9, 2026, 11:01:44 AM UTC
Historical outboundEmail
Jul 9, 2026, 2:01:49 PM UTC
Automated/CRM messageEmail
Jul 9, 2026, 7:00:38 PM UTC
Historical human replySMS

Automated Reminder: Your ZOOM call with Sober Living Riches is in 2 hours at 2:00 PM  PDT. We just sent you an email with the zoom link (please check your junk/spam just in case). As a reminder, please join from a device with a large monitor so we can share our screen as we review your goals & potential income with sober living. Talk soon!

Jul 9, 2026, 7:00:39 PM UTC
Automated/CRM messageEmail
Jul 9, 2026, 8:59:00 PM UTC
Historical human replySMS

Automated Reminder: Your Zoom call with Sober Living Riches is starting now! We just sent you another email with all your appointment information & the zoom link. You can join here: https://us06web.zoom.us/j/8924530025?pwd=6BHdSP6I4Q89w8sHIceOPxcYYKGxC4.1

Jul 9, 2026, 8:59:02 PM UTC
Historical human replySMS

https://soberlivingriches.com/case-studies

Jul 9, 2026, 9:54:49 PM UTC
Historical human replyOther

Hope you're good, how was your call with Josh?

Jul 10, 2026, 2:01:54 AM UTC