Live video podcastPremieres Wed, Oct 28 on YouTube Live00d 00h 00m

Executive Upskill

Three operators talk AI, business and brand from the seats they've held. Live on YouTube, clipped for your feed.

  • AI agents on the org chart
  • Human review, built in
  • Margin math on AI pilots
  • Chatbots as brand voice
  • Board questions about AI
  • A venture fund run on agents
  • Month-end close, automated
  • Moats you can't prompt
  • Blockchain's second act
  • Pop culture as market signal
James Christopher on the call from his home office
James Christopher
Greg Fisher
Bryce Gilleland

Pull up a chair

Three operators on one call. The premiere streams live on YouTube on Wed, Oct 28. Bring a question for the chat.

Get premiere alerts

Watch live or catch the clips

The full episode streams on YouTube Live, and you can ask in the chat. We cut the best exchanges into clips for Shorts, Instagram and TikTok.

YouTube Live@ExecutiveUpskill
Episode 1: Your 2027 AI Budget, Argued Three Ways

Premieres in

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Wed, Oct 28, 11:00 AM PT / 2:00 PM ET

Watch the full episode live and ask in the chat while the hosts can still answer.

Greg Fisher laughing on set
YouTube Shorts@ExecutiveUpskill

One argument per clip, short enough for the gap between meetings.

Watch Shorts
Instagram@executiveupskill

Reels of the sharpest exchanges, plus behind-the-set Stories.

Follow on Instagram
James Christopher on a video call
TikTok@executiveupskill

Fast cuts of the moments the hosts disagree, ready for you to stitch.

Follow on TikTok
Bryce Gilleland on a video call

Browse by lens

Meet the hosts

Pick the lens you need

Season 1, sorted by the host who leads each episode. The other two still weigh in.

One question. Three lenses.

Pick a question you're facing. Each host makes his call.

Should we replace a hire with an AI agent?

James, brand lens
Name the person who reviews the agent's work before a customer sees it. If you can't name them, you're hiring a liability.
Greg, AI and finance lens
Price the agent with the hours someone spends checking its work. Compare that number to the salary, then decide.
Bryce, venture lens
I run my fund's operations on agents I designed. Start with a workflow you can write down step by step. If you can't write it down, the agent can't run it.

The full argument airs live on Wed, Oct 28.

Get premiere alertsAsk your own

Host opinions for discussion. Nothing here is financial, legal or investment advice.

Meet the hosts

Host & moderator, brand lens

James Christopher

James is one of the few marketing leaders in the world who holds patents in machine learning and advanced sensor technology. With more than 20 years as a marketing executive, user experience expert and brand leader, he has applied his technical insights across IoT, health and wellness, and consumer electronics. He currently advises startups on AI transformation and is an advocate of human-in-the-loop systems and IRL experiences.

The question he asks first
“Who's the human in this loop, and can they say no?”
James on LinkedIn

Free live sessions from F3 Insights

Try it on your own files

F3 Insights, an AI and finance advisory affiliated with the show, runs free online working sessions for executives. Bring a laptop and a real problem.

Hands-on: bring your own files and toolsFree, online, 30 to 90 minutes

October 2026

SMTWTFS
Working session Weekly meetup

Every Saturday, 8:30 AM to 10:00 AM PT: Coffee and AI Coding. Weekly show-and-tell. Bring what you built, or come to watch.

Register free

Thu

8

Oct

Next up

Getting Set Up with AI Tools

4:30 PM to 5:00 PM PT. Free, online, 30 min.

Get your AI tools installed and working before you need them.

Pairs with EP 01, Your 2027 AI Budget, Argued Three Ways

Register freeOpens the F3 Insights site

Thu

22

Oct

AI and Excel for Forecasting

4:30 PM to 5:00 PM PT. Free, online, 30 min.

Bring AI into the spreadsheet you forecast in.

Pairs with EP 01, Your 2027 AI Budget, Argued Three Ways

Register freeOpens the F3 Insights site

Thu

5

Nov

Managing AI Context and Memory

4:30 PM to 5:00 PM PT. Free, online, 30 min.

Control what your AI tools remember between conversations.

Pairs with EP 03, Running a Venture Fund on AI Agents

Register freeOpens the F3 Insights site

Thu

19

Nov

Variance Analysis Automation

4:30 PM to 5:00 PM PT. Free, online, 30 min.

Have AI draft the budget-versus-actual explanations you write each month.

Pairs with EP 11, Reporting Your Board Will Believe

Register freeOpens the F3 Insights site

Thu

3

Dec

Automated Meeting Notes

4:30 PM to 5:00 PM PT. Free, online, 30 min.

Turn meeting recordings into decisions and follow-ups you can send.

Pairs with EP 08, Hire a Person or Deploy an Agent?

Register freeOpens the F3 Insights site

The show premieres Wed, Oct 28.

Get premiere alertsAll sessions

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We send a reminder the day before and the live link when we start, then one email per episode.

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Before you tune in

When does Executive Upskill air?

The premiere streams on YouTube Live on Wednesday, October 28 at 11:00 AM PT. New episodes follow on a regular schedule we'll announce to the alerts list first. Get premiere alerts and we'll email you the day before and again when we go live.

Can I join live?

Yes. Open the stream on YouTube, sign in and post in the live chat. The hosts take questions from the chat during the show. If you miss it, the replay stays at the same link.

How do I get my question on air?

Send it through the question form on this page before the cutoff shown there, or post it in the live chat during the show. The hosts pick questions that name a real decision and give enough context to argue about. You can ask us to read yours without your name.

Who should pitch as a guest?

Founders and operators who made a hard call on AI, money or brand and will defend it on camera. You can pitch yourself or someone you know.

Is it free, and where can I watch?

Yes, it's free. Watch full episodes live or on replay on YouTube, and find short clips on YouTube Shorts, Instagram and TikTok. The affiliated F3 Insights sessions are free too, and you register for them on the F3 Insights site.