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Functional Executives

Functional Executives

"Raccoons in a Trench Coat" – The Realities of Building Your Own Open Brain

Sep 14, 2026 · 33 min · 8 segments

Welcome to Functional Executives, where Jim Boswell and Veer Hossain peel back the glossy pitch deck to give a ground-level field report on building personal AI "Open Brain" systems. If you're a…

Welcome to Functional Executives, where Jim Boswell and Veer Hossain peel back the glossy pitch deck to give a ground-level field report on building personal AI "Open Brain" systems. If you're a leader thinking AI will magically 10x your productivity (spoiler: it won’t), or just want to know what actually happens after the hype, this one’s for you. ## **Episode Highlights** **The Reality Behind the Brochure:** Jim Boswell and Veer Hossain share why their Open Brain prototypes—meant to be the digital second brains—work well… until they really don’t.**The Raccoo...**

Welcome to Functional Executives, where Jim Boswell and Veer Hossain peel back the glossy pitch deck to give a ground-level field report on building personal AI "Open Brain" systems. If you're a…

Spotify Amazon Music Website

Show signals: SuitabilitySafeBiasNot political

Speakers: Veer HossainHostJim BoswellHost

Top entities: Large language model×16 Trench coat Claude×4 Notion Markdown×2

What the Open Brain Actually Does2:55 – 11:09

J

Jim BoswellHost

2:55

Right.

J

Jim BoswellHost

2:55

We said, well, I mean, the problem was you have lots of information.

J

Jim BoswellHost

3:03

You can't necessarily access it all.

J

Jim BoswellHost

3:06

And you're having to give little pieces of context to your LLM every time.

V

Veer HossainHost

3:11

Oh yeah, 100%.

V

Veer HossainHost

3:12

The issue was, it's like, how do I switch from Claude to ChadGBT to a local model, whatever it is, and still have it know everything about me, the work I'm doing, and be able to give me meaningful suggestions? That's the whole goal of an open brain, and it's a lot.

V

Veer HossainHost

3:33

It's actually not just one project.

J

Jim BoswellHost

3:36

There was

V

Veer HossainHost

3:36

a

J

Jim BoswellHost

3:36

data autonomy piece to that.

J

Jim BoswellHost

3:39

I mean, it was solving a lot of problems.

J

Jim BoswellHost

3:41

It was trying to address my data is my data.

J

Jim BoswellHost

3:45

I should be able to use any tool I want.

J

Jim BoswellHost

3:47

I should be able to access all my data.

J

Jim BoswellHost

3:48

I should be able to synthesize it and come up with something net new.

J

Jim BoswellHost

3:52

And I think that was the brochure.

J

Jim BoswellHost

3:54

Like, do all those things.

V

Veer HossainHost

3:55

Yeah, 100%.

V

Veer HossainHost

3:58

I would guess the best question to ask you is you built a product, you call it Cyrano, which I still think is a really clever wording, Cyrano balcony, and you've got all sorts of Cyrano related.

V

Veer HossainHost

4:14

It's a theme of all these little products that you've put together.

V

Veer HossainHost

4:18

So again, you call it the brochure.

V

Veer HossainHost

4:21

I said pitch deck, but marketing materials were Really flashy.

V

Veer HossainHost

4:27

How are you seeing it in action as you use it day to day? What are you seeing? What's real life?

J

Jim BoswellHost

4:36

It's really useful.

J

Jim BoswellHost

4:38

I mean, and I think what we talked about to people a while back was...

Large language modelEntity
96%16 mentions
Trench coatEntityClothing
88%1 mention
ClaudeSoftware ApplicationSoftware
81%4 mentions
NotionSoftware ApplicationProductivity software
73%1 mention
MarkdownEntityProgramming language
65%2 mentions
ChatGPTSoftware ApplicationSoftware
58%1 mention
ObsidianSoftware ApplicationSoftware
50%2 mentions
application programming interfaceEntityType of software
42%1 mention
OpenAI CodexEntitySoftware
35%1 mention
Microsoft OutlookSoftware ApplicationSoftware
27%1 mention
PostgreSQLSoftware ApplicationSystem software
19%1 mention
SharePointSoftware ApplicationSoftware
12%2 mentions
MicrosoftCompanyTechnology company
4%1 mention

AI System OperationsTechnology > Software Engineering
Open Brain Knowledge ManagementTechnology > Artificial Intelligence > Personal AI Systems
Cross-Model Personal ContextTechnology > Artificial Intelligence > Personal AI Systems > Open Brain Knowledge Management
Knowledge Worker ProductivityTechnology > Artificial Intelligence > AI Applications
Automated Email and Task PrioritizationTechnology > Artificial Intelligence > AI Applications > Knowledge Worker Productivity
AI Retrieval SystemsTechnology > Data Management > Data Architecture
Search Relevance and Contextual FilteringTechnology > Data Management > Data Architecture > AI Retrieval Systems
Security and Infrastructure MaintenanceTechnology > Software Engineering > AI System Operations
API Key Rotation and Credential ManagementTechnology > Software Engineering > AI System Operations > Security and Infrastructure Maintenance
AI-Enabled Professional ServicesBusiness > Entrepreneurship
Consulting Sales EnablementBusiness > Entrepreneurship > AI-Enabled Professional Services
Revenue Generation Through AI-Assisted ProposalsBusiness > Entrepreneurship > AI-Enabled Professional Services > Consulting Sales Enablement
Data ArchitectureTechnology > Data Management
AI ApplicationsTechnology > Artificial Intelligence
Software EngineeringTechnology
Data ManagementTechnology
Personal AI SystemsTechnology > Artificial Intelligence
Technology
Business
EntrepreneurshipBusiness
Artificial IntelligenceTechnology

What the Open Brain Actually Does2:55 – 11:09

J

Jim BoswellHost

2:55

Right.

J

Jim BoswellHost

2:55

We said, well, I mean, the problem was you have lots of information.

J

Jim BoswellHost

3:03

You can't necessarily access it all.

J

Jim BoswellHost

3:06

And you're having to give little pieces of context to your LLM every time.

V

Veer HossainHost

3:11

Oh yeah, 100%.

V

Veer HossainHost

3:12

The issue was, it's like, how do I switch from Claude to ChadGBT to a local model, whatever it is, and still have it know everything about me, the work I'm doing, and be able to give me meaningful suggestions? That's the whole goal of an open brain, and it's a lot.

V

Veer HossainHost

3:33

It's actually not just one project.

J

Jim BoswellHost

3:36

There was

V

Veer HossainHost

3:36

a

J

Jim BoswellHost

3:36

data autonomy piece to that.

J

Jim BoswellHost

3:39

I mean, it was solving a lot of problems.

J

Jim BoswellHost

3:41

It was trying to address my data is my data.

J

Jim BoswellHost

3:45

I should be able to use any tool I want.

J

Jim BoswellHost

3:47

I should be able to access all my data.

J

Jim BoswellHost

3:48

I should be able to synthesize it and come up with something net new.

J

Jim BoswellHost

3:52

And I think that was the brochure.

J

Jim BoswellHost

3:54

Like, do all those things.

V

Veer HossainHost

3:55

Yeah, 100%.

V

Veer HossainHost

3:58

I would guess the best question to ask you is you built a product, you call it Cyrano, which I still think is a really clever wording, Cyrano balcony, and you've got all sorts of Cyrano related.

V

Veer HossainHost

4:14

It's a theme of all these little products that you've put together.

V

Veer HossainHost

4:18

So again, you call it the brochure.

V

Veer HossainHost

4:21

I said pitch deck, but marketing materials were Really flashy.

V

Veer HossainHost

4:27

How are you seeing it in action as you use it day to day? What are you seeing? What's real life?

J

Jim BoswellHost

4:36

It's really useful.

J

Jim BoswellHost

4:38

I mean, and I think what we talked about to people a while back was...

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