StoryBrand Guide Retreat · Build It to Last · Nashville
The Time To Guide.
running a business that's highly autonomous and deeply human
Jay Owen.aiwithjay.com
Quick gut check · on your feet
On a scale of 1 to 5…
1
2
3
4
5
stand up if you're a four or a five
The Time To Guide · NashvilleJay Owen.
Circa 1994
There have been 3 times I thought…
This changes everything about everything.
Time 01
The Web
I had to convince people they even needed a website.
Time 02
The iPhone
Then everything had to fit on this screen.
Time 03
ChatGPT
The first answer that actually made sense.
The Time To Guide · NashvilleJay Owen.
Change never asks permission
Will you be shaped by it, or will you shape it?
The Time To Guide · NashvilleJay Owen.
Part 2 · First, breathe
You're not behind.
2.2%
of US households pay for an AI subscription
Source: PNC and Bank of America card data, 2026
~1 in 4
US businesses pay for AI
Source: US Census Bureau, 2026
The Time To Guide · NashvilleJay Owen.
1,000 people on earth
Six of them pay for AI.
ai years are like 70 human years
1,000 dots, 1,000 people on earth. The red ones pay for an AI tool. Source: OpenAI's 50 million paid consumer subscribers, February 2026, against a world population near 8.2 billion.
The Time To Guide · NashvilleJay Owen.
My daughter's science fair · two years ago
Real photo or AI?
She tested 100 people on 10 photos: five real, five AI. They got it right 37% of the time.
and that was two years ago
37%
The Time To Guide · NashvilleJay Owen.
The future worth building is both
The machines take the tasks
Highly autonomous.
If the work is a checklist on a computer, the robot can already do it.
&
The people take the people
Deeply human.
The part only a guide can do. Sit with the client. Make the call.
Broadway photo: dconvertini, CC BY-SA 2.0, via Wikimedia Commons
Something our pastor says
For every mile of road, there's two miles of ditch.
Ditch 01
"It's only AI. People don't matter."
The road
Autonomous & human
Ditch 02
"I'm never touching it."
Natchez Trace Parkway photo: Lasermanmcgee, CC BY-SA 4.0, via Wikimedia Commons
The Time To Guide · NashvilleJay Owen.
The deeply human lane, for every guide
Relationship is the moat now.
CoffeeLunchDinnerFlights to see clientsLive eventsWorkshopsWhiteboard sessions
the machine can make the content. you make the call.
The Time To Guide · NashvilleJay Owen.
Part 4 · Run every task in your business through four doors, in order
D.A.D.S.
D
Delete
Old task lists, templates, and SOPs. Select all, delete.
A
Automate
Seven workflows to copy, coming up.
D
Delegate
To an AI agent, a VA, a contractor, or your what-if teammate.
S
Schedule
If it has to be you, put it on the calendar.
automate used to be the smallest door. now it's the biggest.
The Time To Guide · NashvilleJay Owen.
Seven workflows to copy · 1 of 2 · team of one or twenty
01Ask me questions firstBefore any proposal, contract, or brief: "Ask me any questions you need to create the best possible outcome."
02Make it a skillWhen it's right: "Create a skill from this so I can do the exact same thing next time." The first took longer. The 52 after were almost instant.
03Talk, don't typeWispr Flow dictation: about 300 words a minute, against about 100 typing.
04Meeting to follow-upGranola on every client call. Send the follow-up while you still care.
The Time To Guide · NashvilleJay Owen.
Seven workflows to copy · 2 of 2
Workflow 05
Revision rounds
A client left 42 comments. Claude matched the Figma and made the changes, a second agent checked the work with screenshots, Claude drafted the reply, and a person sent it.
Workflow 06
Your numbers, made visible
P&L, balance sheet, and cash flow, with last year's comparison: "What am I missing?" One agency owner ran 10 years of billing data, found an undervalued top client, and got a referral.
Workflow 07
Read-only data, plain questions
Connect AI read-only to live data and ask in plain language. It gives three or four recommendations. A human applies the judgment.
the agents do the checking. a person still sends it.
The Time To Guide · NashvilleJay Owen.
Point both moves at the work guides already sell
Ask me questions first. Then make it a skill.
01BrandScript
02One-liner
03Website wireframe copy
04Sales emails
05Lead generator
06Client follow-up
07Proposal
→One skill each
The Time To Guide · NashvilleJay Owen.
When you confuse, you'll lose. That goes for prompts too.
Hand AI your BrandScript.
Clear structure in
BrandScript & one-liner
The template you already own.
→
The machine
Stops guessing
Probabilistic by default. Structure makes it consistent.
→
Clear message out
Same shape, every time
For every client you serve.
The Time To Guide · NashvilleJay Owen.
Part 5 · Live demo A
The interview & the skill.
Ask for a deliverable
A one-liner draft or a proposal.
"Ask me questions first"
Let it interview you.
Answer out loud
Dictate with Wispr Flow.
"Create a skill from this"
Save what worked.
Run it again
A second client. Same structure.
watch what happens on the second pass
The Time To Guide · NashvilleJay Owen.
Live demo, part two · pick one
Just enough to be dangerous, and now I can build it.
Demo B
Rebuild a site live
Replit. A small-business site rebuilt in about three prompts, published to a preview URL, then fed a brand kit.
Demo C
My agents at work
Text my agent a real task from the stage. Then the approval step: nothing goes out without a yes.
The Time To Guide · NashvilleJay Owen.
Demo backup · if the Wi-Fi wins
Same structure, second client.
Run one
The interview
It asks. You answer out loud.
→
Saved
The skill
"Create a skill from this."
→
Run two
New client
The same shape comes back.
The Time To Guide · NashvilleJay Owen.
Part 6 · What to sell, whether you're a team of one or twenty
Give clients a simple plan in.
Start
The build day
Half a day with one client: domain, branded site and copy, lead generator, automated follow-up. Or run it as an AI-assisted BrandScript workshop.
→
Then
The blueprint
A paid, full-day discovery before anything gets built.
→
Ongoing
The retainer
Twelve months. Plan annually, adjust quarterly, report monthly, execute weekly.
"that would have taken three months"
The Time To Guide · NashvilleJay Owen.
You can build it yourself now, even as a team of one
01
Off WordPress
Replit, with no deep dev skills. A Squarespace site cloned in about three prompts and live the same day.
02
Custom software
I rebuilt our project management system off teamwork.com, and prototyped an app before the first meeting.
03
Get found in AI answers
One agency owner got his agency found on ChatGPT within 30 days.
sites, software, and search
The Time To Guide · NashvilleJay Owen.
When a client asks, "Do you use AI?"
The honest answer is yes. The useful answer is why.
so you can be as relational as humanly possible
The Time To Guide · NashvilleJay Owen.
Part 7 · Write the rules while nothing is on fire
Automate the work. Keep the relationship.
The never list
Never publish the first draft
Never paste in data people didn't agree to share
Never use a tool to avoid a person
Never lie about it if you're asked
And keep SSNs, health data, and bank or card info out.
A named human boss
Every agent loop gets a person, by name, who reviews the output, takes the call if it goes wrong, and can stop the loop.
Team of one? The boss is you.
The Time To Guide · NashvilleJay Owen.
Multiply people, don't subtract them · my son is dyslexic, and so am I
The ideas were never the problem.
getting them out of his head was
The Time To Guide · NashvilleJay Owen.
When ten hours becomes two
Steward the dividend.
you're not the owner. you're the manager.
Say out loud where the eight hours go. If you do not name it, they disappear.
The Time To Guide · NashvilleJay Owen.
Part 8 · Your plan · the next 30 days · team of one or twenty
Pick the clog in your week.
01Get a paid Claude or ChatGPT account
02Give the task you hate 30 minutes with one tool
03"Ask me questions first," then save your first skill
04Write your never list. Put a name on every loop.
05Granola on your calls, Wispr Flow on your keyboard
The Time To Guide · NashvilleJay Owen.
Your plan · the next 90 days
Small and finished beats big and theoretical.
01Find your continually curious personTeam of one? It's probably you. Hire if you need to.
02Run every recurring task through the four doorsDelete first.
03Move one site off WordPress, or rebuild one toolYou can build it yourself now.
04Package one AI offer you can sellA build day, a blueprint, or an audit.
05Book in-person time with your top clientsDinner and a whiteboard.
The Time To Guide · NashvilleJay Owen.
Questions · the plan stays on screen
Q&A
Next 30 days
Paid Claude or ChatGPT
30 minutes on the task you hate
Ask me questions first. Save a skill.
Write your never list
Granola and Wispr Flow
Next 90 days
Find your curious person
Four doors, delete first
Off WordPress, or one tool
Package one AI offer
In-person time with top clients
The Time To Guide · NashvilleJay Owen.
One year from now: two guides, same tools
Holding back is still a vote.
Waited it out, and never told anyone what he was thinking.
Told her clients and her team where this was going, and that they still mattered.
both of them voted
Natchez Trace bridge photo: The_Gut, CC BY 2.0, via Wikimedia Commons
The Time To Guide · NashvilleJay Owen.
Be the guide your clients need
It's time to guide.
aiwithjay.com
Photos via Wikimedia Commons: Lower Broadway, Antony-22, CC BY-SA 4.0 · Broadway lights, dconvertini, CC BY-SA 2.0 · Natchez Trace Parkway, Lasermanmcgee, CC BY-SA 4.0 · Natchez Trace bridge, The_Gut, CC BY 2.0 · Skyline, Shelby Street Bridge, and AT&T Building, Kaldari, public domain/CC0 · I-65 skyline, Cessna86, public domain · Ryman Auditorium, CC0.
