The operator.
Who you are, in all the ways you show up. Not one title — a multipreneur's identity doesn't reduce to a single company.
Primary contact
How you describe what you do
In your own words — when someone asks what you do, what do you tell them?
Public-facing roles
Every capacity you show up in publicly — businesses, board seats, elected or appointed positions, advisory roles. Add as many as you need. The deeper detail per entity comes in the next section.
Other key people
Anyone who shapes decisions across your portfolio — a business partner, COO, chief of staff, EA. Add as many as you need.
Billing
Scheduling
The portfolio map.
Every hat you wear. We'll fill out one card per entity or role. Keep it fast — mostly dropdowns and short answers. The detail comes later.
Your entities & roles
One card per entity or major role. For civic or board roles that aren't revenue entities, the revenue field has an option for that. The two fields in the highlighted box — time and mental energy — matter most: answer both honestly.
The seams.
Where the friction actually lives. Almost never inside one business. Almost always between them.
Between the entities
When something comes across your desk, how do you decide which entity it belongs to?
Where do leads or opportunities for one business come from another? Is that working, or is it leaking?
Whose calendar are you actually living in? Does one role bleed into the others?
The one thing
If you could fix ONE thing in your business tomorrow — one thing that would make everything else easier — what would it be?
How long has this been a problem? What has it already cost you in time, revenue, or stress?
What have you already tried to fix it? Why didn’t it stick?
Where things drop
When you're pulled into one role, what falls behind in the others?
Where is information about one entity trapped in a tool, an inbox, or a person that the others can't reach?
Is there one assistant, ops person, or system that serves all of it — or does each entity have its own?
Operations & tools
Answer for whichever entity has the most operational complexity — or answer separately per entity if they're materially different.
Walk us through how a new client moves through that business — from first contact to delivered result. Where does it slow down or break?
What tools and software run it? List everything — CRM, project management, billing, comms, scheduling. Note which work well and which you just tolerate.
Where it’s going.
What stays, what grows, what gets put down.
Engine and drag
Which of your roles or entities do you want to grow over the next three years?
Which do you want to exit, hand off, or wind down?
Which is non-negotiable, regardless of return? (Often the civic or family one.)
Three years from now, are you still wearing all of these hats? If not, which ones have you put down?
Revenue across the portfolio
The dream state
If you had unlimited funds and could hire anyone — a full team, every role you've been missing — who would you bring in first and what would they do? Don't be realistic. Dream team only.
Describe the ideal version of your working life three years out. How the portfolio is shaped, how you spend your days, what you've stopped doing.
If everything ran exactly the way you want it to — what would change about your personal life?
What success looks like
If we looked back 12 months from today and this engagement was a smashing success in your eyes — what would have needed to happen?
What does success look like in 90 days? What is the first thing you want to feel different about?
Readiness for the shift.
Where things stand with technology today — and where a well-placed system could actually move the needle across the portfolio.
Tech comfort & prior experience
How would you rate your own comfort with technology, 1 (low) to 10 (high)? What about the teams across your entities?
Have you experimented with any AI tools — ChatGPT, Notion AI, automation, voice agents? What was that experience like?
Are your teams generally open to adopting new tools, or is there resistance? Does that differ by entity?
When you think about a “company brain” — a single place that holds how things run — is it one brain for the whole portfolio, or one per entity? Where would the boundaries live?
Quick-win opportunity scan
For each area, note how it works today, where the pain is, and whether AI or automation could help. Answer for the entity with the most operational complexity — or note differences between entities in the cells. Leave blank if it doesn't apply.
| Business area | How it works today | Where the pain is | AI opportunity? |
|---|
Budget & decision-making
Do you have a budget range in mind for this type of initiative? What's your thinking on investment vs. expected return?
Who else is involved in a decision like this — a partner, investor, board, finance lead? Do they need to be in the next conversation?
On a scale of 1–10, how urgent is solving the problems we discussed? What happens if nothing changes in the next 6 months?
What’s already built.
Brand assets, the current tech stack, and the accomplishments worth knowing about. So we can audit and build from what exists rather than rebuild from zero.
How would you like to answer this?
Brand and digital presence almost always differ per entity. Tech stack might be shared, might not. Choose whichever fits.
Branding
Current tech stack
Digital presence
Worth knowing
These attach to you, the operator — not to any one entity.