FAQ
Straight answers for busy founders.
What exactly is a Chief of Staff, and why would I need one?
A Chief of Staff runs the business so the leader can lead it. Systems, priorities, follow through, judgment. Every executive we have supported had one. Most founders need one years before they can afford the traditional six figure version. That gap is exactly what we close from both sides: our system runs the machine a Chief of Staff would run, and our quarterly and fractional involvement brings the judgment one would sit beside you with, all without the six figure salary.
How is that different from an assistant?
Assistants manage calendars and admin. A Chief of Staff drives strategy, systems, and follow through, deeply embedded in how the business actually runs. That is the level our systems are built at, whether you install them yourself or bring us in to run them with you.
Which of the four options is right for me?
If you are just meeting us, start with the Playbook, and if within two weeks you decide you want us building beside you, your $997 becomes a credit toward your Cohort seat. If you want it built and done from day one, the Cohort. If you have the systems and want a partner on the big calls, the Quarterly Check In. And if the season is too big to run alone, apply for us to step in. Nothing you build at one level is wasted at the next.
What is actually in the Playbook?
Six AI employees who live inside Claude, each with a name, a job, and a schedule. One plans your week, one handles leads, one drafts replies, one drafts content, one watches money, one organizes your notes and processes. They all read one page you write once, your Brain, so everything sounds like you, and Claude cannot send your email, Anthropic built it that way, so every word waits in your Drafts for your yes. The book assumes zero AI experience, explains every click, and includes an emergency brake page, because you are the boss and bosses set the tempo.
What do I need to run it?
A Google account for your business (Gmail and Google Calendar), a paid Claude plan (any tier), and the Claude app on your computer, open while your team works. If you live in Outlook, hold on: we will release that version once we have tested it properly on our own accounts, because we do not sell maybes.
Playbook or Cohort: which should I choose?
Same system, two ways to build it, and the honest answer is that most founders are happier in the Cohort. The Playbook is right if you enjoy building alone and want the lowest cost of entry. The Cohort is right if you want it done: we write your Brain together, hire your six employees live, and approve your first drafts before we hang up, so nothing stalls in a someday folder. The choice is also reversible on purpose: buy the Playbook, and for two weeks your $997 is a full credit toward a Cohort seat. Still torn? Write us and we will find fifteen minutes to talk it through, no pitch.
Do I need to be technical?
If you can copy and paste, you can hire your team. Every page is written for someone who has never touched AI before, every word gets explained, every step says exactly where to click, and nothing requires code.
What happens in a Quarterly Check In?
A few days ahead, you share view access to your numbers and answer three short questions, about fifteen minutes of your time. Then we spend ninety minutes together on three things: what your numbers are saying, which system needs tuning, and the one decision you have been circling. You leave with a ninety day plan, written live on the call.
Why is the Quarterly Check In a one year commitment?
Because one conversation is advice, and four are momentum. Each session builds on the last: we remember what you committed to, we watch your trends across quarters, and by the fourth session we know your business almost as well as you do. That compounding is the entire value, and it cannot happen in a single meeting.
How does We Step In work, and why is it by application?
We come on board ourselves, fractionally or for a defined project: a launch, a first hire, a messy quarter, a big client. We do the work personally rather than through a team, so we take only a few founders at a time and we decline more than we accept. The application is one email telling us about your business and the moment you are in.
How quickly can we start?
The Playbook is yours the day you buy it, and cohorts run on scheduled dates. For check ins and stepping in, we begin with a discovery call to align on priorities, and most engagements start within one to two weeks.
How do you measure success?
We focus on outcomes that matter: faster decision making, smoother workflows, clear priorities, and ultimately, growth without chaos. Regular check ins and transparent metrics keep us accountable to your goals.
