Question 1

How much does Sidekick Solo cost?

Accepted Answer

Sidekick Solo is $800 CAD, one-time. There is also a Solo + Coaching option at $1,400 CAD that includes everything in Solo plus four weekly 30-minute coaching sessions with Chase, async messaging between sessions, and hands-on support for your first month. No subscription, no retainer, no ongoing charges. You pay once and the workspace is yours.

Question 2

What's the difference between Sidekick Solo and Sidekick for Teams?

Accepted Answer

Sidekick Solo is a done-for-you personal AI operating system for professionals and business owners. You get a configured workspace built around your specific context, voice, and workflows, delivered directly to you and ready to use. Sidekick for Teams is an organizational deployment where we build custom AI workflows for your team's operations: lead generation, client management, internal processes, and more. Solo is for you personally. Teams is for your organization.

Question 3

What's included in Sidekick Solo?

Accepted Answer

Twenty configured skills covering strategic thinking, communications, meeting intelligence, and operations. Done-for-you setup built around your specific role and context. Seven days of direct email support from Chase. A refinement window to adjust anything that is not working the way you would expect. You receive a workspace that is ready to use from session one, not a template you configure yourself.

Question 4

Can't I just set up Claude myself?

Accepted Answer

You can. Most professionals and business owners who find Sidekick Solo have already tried. The difference is between a general-purpose AI that starts from zero every session and a configured workspace that already knows your role, your priorities, your communication style, and the way you make decisions. Solo is twenty integrated skills built around your specific context, not a blank chat window with a clever prompt.

Question 5

How long does Sidekick Solo setup take?

Accepted Answer

One session, typically two to three hours. We book a working session, go through your role, your clients, your communication style, and how you make decisions, then configure your workspace around that. You leave with a system that is ready to use the same day.

Question 6

Do I need any technical skills for Sidekick Solo?

Accepted Answer

No. If you can use Claude, you can use Sidekick Solo. The setup session requires nothing technical from you. You describe how you work and we build around it. After delivery, using the system is just opening Cowork and starting a session. Nothing to install, configure, or maintain.

Question 7

Is my data private with Sidekick Solo?

Accepted Answer

Yes. Your Solo workspace runs on your own Claude account. Sidekick does not have access to your sessions, your files, or your conversations after delivery. Nothing you put into your workspace is used to train AI models or shared with anyone. Your context stays on your machine, in your account.

Question 8

What if Solo doesn't work for me?

Accepted Answer

Every Solo delivery includes a refinement window and seven days of direct support from Chase. If a skill is not landing or a workflow does not fit how you actually work, we adjust it. Most refinements are small: a tone shift, a different output format, an added context source. The goal is a workspace you actually use, not one that looks impressive on delivery day.

Question 9

What Claude plan do I need for Sidekick Solo?

Accepted Answer

You need at minimum Claude's Pro plan. If you are not hitting your plan's usage limits, you are likely not using this enough to get the ROI. Pro handles most users well. If you run multiple long sessions each day, Claude Max removes the ceiling entirely.

Question 10

Why does a Cowork session take longer than a regular Claude chat?

Accepted Answer

Cowork is not a chat interface. When you give it a task, it reads your files, runs specialized tools, and builds actual output, not a single generated response. Sessions take longer because they are doing more. The people who get the most out of Solo keep two or three sessions open at once and rotate between them. The wait disappears.

Question 11

What if I start with Solo and later want a Teams deployment?

Accepted Answer

They are designed to work together. Clients who start with Solo and move to a Teams deployment build on the foundation they have already established. The context you build in Solo (your workflows, your communication style, your decision patterns) becomes the starting point for a broader deployment, not something you rebuild from scratch.

Question 12

Do you replace our existing tools?

Accepted Answer

No. Sidekick builds automation around your current stack. We connect to what you already use (your CRM, your email tools, your project management software) and build workflows that run on top of them. The goal is fewer manual steps, not a rip-and-replace.

Question 13

What does human-in-the-loop actually mean in practice?

Accepted Answer

It means nothing executes without your team approving it first. AI handles the research, drafting, and preparation. Your team reviews the output, makes any edits, and approves before anything gets sent or logged. We design this into every workflow from the start, not as an add-on. That review step is where trust gets built, and it is non-negotiable.

Question 14

How do you handle our data?

Accepted Answer

Your data stays yours. We implement strict protocols ensuring no sensitive information is used to train external AI models. Read/write access is granular: we touch only what the workflow requires, and nothing more. Data handling is scoped as part of every engagement; it is one of the first things we map in the Discovery Sprint.

Question 15

What does the engagement look like: timeline, cost, commitment?

Accepted Answer

Every engagement starts with a free 30-minute Intro Call. From there, we run a paid Discovery Sprint, a focused assessment that maps your workflows and identifies where automation actually drives value. The Sprint is a standalone deliverable: if you walk away after it, you still have a clear automation roadmap. Sprint and build pricing is scoped on the Intro Call. No retainer begins until your workflows are live and performing.

Question 16

We've tried AI before and it didn't stick. Why would this be different?

Accepted Answer

Most AI projects fail because they ask your team to learn a new tool and change how they work. Sidekick inverts this. We map your existing workflows first, then build automation to fit them. And we start with a paid Discovery Sprint, a focused engagement that maps your workflows and identifies where automation actually makes sense, before you commit to a full build. If the Sprint reveals that automation is not the right move for a particular workflow, we will tell you. Your team does not learn a new tool. They just do less of the repetitive parts of their current job.

Question 17

Do we need a technical team to work with you?

Accepted Answer

No. One of our core requirements is that clients do not need to manage anything technical on their end. You will have a clear point of contact at every step. What we do need is someone who understands the workflows we are automating, typically a manager or ops lead, not an engineer.