Roundish. Purple. Two legs, short arms, big bulgy eyes. Might be food related.
George threw that at Chad and Max cold, no setup. Chad's brain went straight to Barney. Max's brain went to the Hamburglar, then landed on Grimace. Same words. Two brains. Two completely different answers. That's context, or more honestly, that's what happens when there isn't enough of it.
HubSpot Breeze Context (Settings, then Breeze, then Context) is where you stop letting HubSpot's AI guess. It's the grown-up evolution of what used to be called AI data sources, and as the crew put it, it's a different wrapper on the same idea: tell the machine who your business is, who you serve, and how you operate, so the content engine, the prospecting agent, and the customer agent all pull from one shared understanding instead of three different guesses. If you've been scrolling past that settings page, this is the one where you stop scrolling and start typing.
Layers Inside The Layers
Max hadn't seen the screen before we hit record, and his first read was the right one. It breaks everything into who the business is, who our customers are, and how we operate and serve them. Three fundamentally different things, kept apart on purpose so they don't get confused with each other.
Then George went a level deeper. Each of those tabs is layered too. The Business tab alone holds Identity and Classification, Location and Scale, Business Profile, Market and Ecosystem, and Products and Services. Onion, Shrek-style.
“When the machine needs to grab what the machine needs to grab, it knows where to go to grab the thing.”
It's the same shape George teaches inside the AI Content System: the second brain, the identities, the stories, the hands, the tools. Every layer has one job, and the machine knows which drawer to open. HubSpot is building that structure inside the portal, one settings tab at a time.
Chad's read: this is the next evolution, and it tracks with how context works everywhere else. In any local AI harness, context lives at multiple levels. Some of it lives in every session. Some of it lives only inside a single project. Some of it gets injected into every single turn so the thing never forgets who it is or wanders off into hallucination shenanigans. Breeze Context is HubSpot walking that same road. Today it feeds the assistant and your agents, and you can see the connective tissue being built for the rest of the platform.
The Business Tab, Field By Field
This is where you start, and most of it is easier than it looks.
Identity and Classification: legal name, web domain, industry, ownership structure, and whether you're public or private. That last one is newer, and it's an open question what HubSpot does with it downstream.
Location and Scale: headquarters, employee count, revenue band, and the year you were founded. Easy stuff.
Business Profile: business description, unique value proposition, business model, primary business goal, mission, vision, and social responsibility. Hit edit and a sidebar opens where you can add, modify, and tweak each one. This is the meaty part.
Market and Ecosystem: main competitors, stakeholders, and your tech stack. Chad's honest read is that some of this is HubSpot collecting a little information for HubSpot. Probably true. Fill it out anyway, because the fields that help you sit in the same form as the fields that help them.
Products and Services: name, description, and category for each thing you sell.
Category is new. The fields used to be name and description only. And George's own portal had zero categories set, even though the Sidekick Strategies site sorts services into categories already (AI services, design, HubSpot implementation). If your AI can't see how you group what you sell, it can't group it for anybody else either.
This Isn't Set It And Forget It
The whole internet still thinks George B. Thomas LLC, DBA Sidekick Strategies, sits in Indian Trail, North Carolina. During this episode he changed the headquarters field to Kings Mountain, North Carolina, which is where the business actually lands in about two weeks. Which means HubSpot now holds context about the business that the rest of the internet doesn't have yet. That's the mindset shift. Breeze Context is a living record, not a form you complete once and abandon. Headcount changes. Revenue band changes. Goals change. So does the truth your AI is repeating on your behalf.
AI Prompts AI The Most Effectively
“I always feel like AI prompts AI the most effectively.”
That line from Chad is the most practical thing in the episode. Don't stare at the empty form. Point your AI assistant at the page with its browser, have it scan the company knowledge you already have (Notion, mission and vision docs, your website, whatever it's connected to), and let it stub out options and drafts.
Then do the part only you can do. Read those drafts with a critical eye and make sure they line up with what the business actually stands for. It kills analysis paralysis, and it hands you something to react to instead of a blinking cursor. As Chad put it, AI knows what AI likes to read, and AI is what's going to be reading this.
Max co-signed immediately, and he was blunt about why. He does this all the time, because a big form full of blank boxes freezes him even when he knows every single answer by heart.
“Use AI to not let this overwhelm you.”
AI assisted, human powered. That phrase came up over and over on this episode, and it's the operating rule. The machine drafts. The human critiques, corrects, and owns the result. That order never flips.
The Personas Didn't Pull Themselves In
George's ideal customer profiles were already in there, built back in the AI data sources era. Personas was completely blank. Which stung, because he's had persona properties baked into that portal since roughly the dawn of HubSpot time.
So he fixed it with browser automation. Claude in Chrome, pointed at his portal, told to read the persona property, look at the screenshot, and populate the personas area inside Context. It went and worked in the browser, and out came the personas: names, job titles, value propositions, the works. Will he go back through and tweak, add, and cut? Of course. But he didn't start from a blank screen, and neither should you.
Chad's question is still open, by the way. Legacy personas, markets, buyer intent, and the ICPs inside Context are not fully connected yet. Do something in one place and it doesn't always show up in the other. Worth watching, and worth asking HubSpot about.
Max's answer for why any of this still matters: the thing has to know who you're selling to and what their goals and challenges are. Same as it was back when you hand-crafted every piece of content yourself. The beans you use to build the end product changed. The requirement didn't.
Team And Processes Is A Six Month Old Baby
George admitted, before he even clicked the tab, that it scared him. Not because of what's inside it, but because of what it implies. If your processes aren't nailed down and you hand them to a machine as context, you just taught a very fast system a very sloppy way to work.
“AI accelerates good, but it also accelerates bad.”
Then he opened it and relaxed. Today the tab is a user profile, an email personality, and a set of email types: cold outreach, follow up, introduction, scheduling, status update, sign up. It's email. All of it. His read: this tab is a six month old baby, not a 16 year old.
Max pushed back on the shrug, and he was right to. Hit add email type, open the dropdown, and look at the list. Humans run each of those differently. You do cold outreach a specific way. You do scheduling a specific way. It looks like just email, but there's real process hiding behind every one of those choices.
Be precise about what you're describing in there, though. This isn't how the human writes. It's how AI does the cold outreach, the follow up, the scheduling on your behalf. Chad's addition: it'll likely feed your own email generation too, so when you're writing AI assisted rather than AI powered start to finish, you can pick a profile and go.
Max's wishlist item: Service Hub. Of every team in a company, service usually carries the tightest and most complex processes, with SLAs, standards, and regulations attached. Marketing sits on the creative end, where process is looser by nature. If any team stands to gain from a Team and Processes tab that grows up, it's the one running support at scale.
One more gap worth naming. You can't build an agent inside HubSpot today and assign it to a team the way you assign a human. Chad noted that permissioning is starting to break out per API key, so agents can at least carry their own permission set. But George's mental picture (Quinn the writer, Finch the editor, Morgan the designer, Riley the developer, all sitting on a HubSpot team) isn't buildable yet.
The Beta Tab Chad Had And George Didn't
Mid-walkthrough, Chad cut in with the line that makes this show worth recording live: I got another tab that you don't have. Beta signup, naturally.
What's in it: free form text plus file upload, with a scope toggle for everybody in the account or just me. So the savvy humans in your portal can hand Breeze their own knowledge-vault markdown without forcing it on everyone else. Sitting next to that are the Breeze assistant app connections: SharePoint, Teams, Linear, Jira, Notion. The places your knowledge actually lives.
Chad's forward-look is the good part. Today you paste context in. The promise is selecting a specific item from a connection, so when that doc or that folder updates, your context updates with it.
“You don't need to come back in here and keep telling Mr. Wizard what the context is.”
George's counterweight: over-contexting is a real risk. He wondered out loud whether the team at HubSpot loses sleep over it, because too much stuffed into one layer can throw off everything that follows downstream. Which is exactly the kind of question you want to ask the person who built the thing.
Two Threads We're Still Pulling
- The why and the how: we're working on getting the HubSpot product manager behind Breeze and Context on the show to answer the deeper questions. No names yet, and it's still a maybe, but the ask is in. Tune in next week.
- Breeze isn't only in HubSpot. It shows up in Excel and in Google Sheets too. Go search that one, it's your tidbit for the day.
Go Fill It Out
Max got asked where his brain was at on all of this, and his answer was about four words long.
“Fill it out. Put information in.”
George closed the show by repeating it, because that's the whole takeaway. Here's what it looks like on Monday morning.
- Open Settings, then Breeze, then Context, and read every field on the Business tab before you type a single word.
- Point your AI assistant at that page, let it read your site and your existing company docs, and have it stub out drafts you then critique.
- Add your products and services, and use the new category field so the categories match how you actually sell.
- Check your ICPs and personas. If personas is blank and you already have a persona property, point your AI at both and let it do the copying.
- Walk Team and Processes and set the email types you actually run, with the personality you actually want.
- Update headquarters, headcount, and revenue band if any of them moved. This is a living record.
Max framed the payoff better than anybody. This isn't about handing the keys over. It's about knowing that if this thing ever talks to one of your customers, it understands who you are and what you do at a basic level. That's trust level one, and Breeze Context is where you earn it.
So go fill it out. And while you're doing that, remember to be a happy, helpful, humble human and do some happy HubSpotting along the way.
