September 25, 2026
Hi Everyone,
Before Joe Kinsella founded CloudHealth Technologies, he wrote down everything he lacked as a solo founder, then recruited six advisors to cover it: two CEOs, two entrepreneurs, a venture capitalist, and a startup executive.
Three years in, CloudHealth had grown from nine customers to more than 600. Kinsella calls that circle "quite possibly the difference between my early success and failure.”
Today we're covering the five seats to fill in your own circle, and a simple check that shows who's missing.
The five seats
- The operator. They’ve already run a company or team at the size you're heading toward. Bring them pricing, hiring plans, and org questions.
- The outsider. They work in a different industry. People in your market share your assumptions; the outsider questions habits your whole industry treats as normal.
- The truth-teller. They’ve disagreed with you before and been right. Invite them to attack the plan before you commit to it.
- The expert knows the one area your next big decision sits in. Raising prices this year? That's someone who knows sales. Opening a second location or market? Someone who has done that exact expansion.
- The leader one step ahead is doing your job at a company one size bigger than yours. They have already faced many of the problems that are heading your way.
One person can hold two seats, but nobody can hold all five, because hearing different views and perspectives is the whole point.
Who's missing from your circle
Write the five seats down the left side of a page. Next to each, add who fills it today and when you last asked that person anything.
Leave investors and your formal board off the page. Their advice can be good, but they're not neutral — they have a stake in what you choose.
Then read the page back and watch for three things:
- An empty row shows who to recruit next.
- The same name in three rows means the circle depends too heavily on one person's view.
- Names all from your own industry mean the outsider seat is empty, even when the page looks full.
Empty rows are normal. When Stanford surveyed more than 200 executives, nearly two thirds of CEOs said they get no coaching or advice from outside their company at all.
Won't five relationships take too much time?
Product executive Ha Nguyen runs her four-person circle on three or four short conversations per person per year, one at a time, whenever a decision touches what that person knows.
She pays them nothing beyond an occasional dinner. There are no standing meetings and no contracts.
Try this today
If the check shows an empty seat, you don't need a formal invitation to fill it. Send the person one specific question about a real decision this week. If the answer helps, ask again next quarter. That's the entire recruitment process.
Kinsella built his whole circle that way, and his conclusion was simple: when you ask for support, there are always people willing to help.
Go deeper
👉 Joe Kinsella: 6 Steps to Creating a Personal Board of Advisors — read this before you recruit anyone; the CloudHealth founder walks through picking advisors who cover what you lack.
👉 Ha Nguyen (via Deb Liu's Perspectives): Forget Networking and Build Your Personal Board of Directors Instead — use her four-person setup as a model for keeping a circle alive on a few calls a year.
👉 Stanford GSB: "Lonely at the Top" Resonates for Most CEOs — worth a look if you want the full numbers on who gets outside advice and who wants it.
Coming up on Monday
On Monday, you’ll learn how to structure your workday around food, caffeine, and focus.
Thanks for reading, and have a great weekend.
P.S. Does your version of this circle exist? Tell us what it looks like