How Now I Can with AI really works

It's an eight-week class where one trusted person from your business, your champion, learns AI beside me in person. They practice on your real work, build your rollout plan in class, and present it to you and the other owners at Week 8.

Getting AI to pay off is a change in how people work, not a software install. It moves fastest when one person inside your business has both the skill and the patience to bring everyone else along.

Wine ClubsThe work centers on keeping more members and getting hours back every release.

FirmsThe work centers on turning the AI tools you already pay for into tools your people use. AI handles the first draft. Your people handle the judgment.

HospitalityThe work centers on making every customer feel like a regular, and giving your team hours back every week.

Training that reaches everyone a little usually changes very little. One person who learns it deeply, on your own work, becomes the person everyone else asks.

Then they teach the next people, with me on call for the hard parts. Your team learns from someone they already trust, and you don't depend on me forever.

Someone with trust inside your business, enough time each week, and the respect of the people who will follow them. Enthusiasm helps, but credibility matters more. They don't need to be technical.

Wine ClubsYour club manager, or you, if you run the club yourself.

FirmsA practice manager, senior paralegal, operations lead or partner. Larger firms can send two.

HospitalityThe person who knows your regulars and keeps them coming back. An owner can be the champion with one to two hours a week.

We'll talk through who it should be before you enroll. It's the most important decision in the program.

• Enroll together with your champion.
• Protect their time each week.
• Meet with me at the midpoint, in Week 4.
• Come to Week 8 and see the plan your champion built with you.
• Ask them each week what they tried.

Your backing is what makes their work count inside your business.

About two and a half hours a week:

• 90 minutes in class, in person
• About 20 minutes between classes, on one real task
• A 30-minute one-on-one with me, which they can shorten or skip

Week 8 runs two and a half hours, and you're in the room. Your champion can also text me any time and hear back the same day.

Every session follows the same rhythm, so nobody spends energy figuring out what comes next.

10 min

Each person shares what they tried this week with their accountability partner.

20 min

Hands-on work beside a partner from another business.

5 min

A real break, and a seat change.

20 min

Hands-on work beside a second partner.

5 min

Another break.

20 min

Your champion works on their own real work, explaining it to a partner as they go.

10 min

Each person commits to one thing for the coming week.

How I teach: I show you. We do it together. You lead it.

1. Clear asks. The first answer is already good.Brief AI like a sharp new coworker: set the scene, make the ask, and show what good looks like.
2. Finish the job. They get it to finished, not just started.Push back, add what's missing, and keep going until it's ready to use.
3. Trust check. They know when not to trust it.Check facts, figures and names against the source, and read it the way your customer will.
4. Handoff. They know what to hand off first.Sort the week into what AI drafts, what they decide, and what stays personal. You sit down with me this week.
5. Protect data. They use it without giving away what isn't yours.What's safe to share with AI, how to take names out, and what never leaves your own systems.
6. Save and reuse. What works gets saved and keeps getting better.A request that worked becomes a saved tool they improve each time they use it.
7. Build it. They put it all together on one real project.One working tool on your own work, built with partners from other businesses helping.
8. Present the plan. They show their plan to bring your team along.With you and the other owners in the room.

Each week builds on the last. Your champion does each skill before anyone names it, and every week's practice is on your own work.

Wine ClubsIn Week 3, they check a drafted club note against the tech sheet. In Week 5, they turn a decline report into a list with member numbers only.

FirmsIn Week 1, they brief AI on a client status update for an attorney to review. In Week 3, they check a contract summary against the original, page by page.

HospitalityIn Week 1, they draft a reply to a real guest inquiry. In Week 5, they sort what guest information is safe to use and what stays in the booking system.

Think of it like a good MBA course. Class time teaches everyone the same core skills. The work between classes is where it becomes yours, the way an MBA student's project is about their own company.

About 20 minutes on one real task from your kind of business. Week 1 is the same task for everyone in their door, so nobody starts with a blank page. After that, they choose from a short list or bring their own. Their choice is the one thing they commit to at the end of class.

Wine ClubsA warm, personal note to a member who's gone quiet, or a one-page summary of what members said after a release.

FirmsA plain-language client update template, or meeting notes turned into next steps with owners and dates. Never with client information in it.

HospitalityA thoughtful reply to every recent review, or a short brief on a regular before their next visit.

Afterward they write a one-minute private note: how long the task usually takes, how long it took this time, and what else it saved. Then they share what they tried with the cohort, without numbers or names, so their partners can help. Our rule is "ask two peers before you ask me."

Three standing partners from other local businesses, set before Week 1 and kept for all eight weeks. I pair people so each pair mixes different working styles, using a short working-style assessment your champion takes before the first class.

One of the three is their accountability partner, who hears their weekly commitment and asks how it went the next week. By Week 8, your champion knows three people from other businesses well, and that peer network lasts past graduation.

No. The class is built for beginners, including nervous ones. I care more about attitude than experience. Someone curious and willing to try will do better than an expert who has already decided how it should work.

In class, everyone uses Claude, so the whole cohort shares one language and can help each other on the same screens. I'll help your champion get set up before Week 1.

What your champion learns carries over to whatever your business uses. Closer to your rollout, we work out how it looks in your own tools, including Microsoft Copilot.

FirmsIf your firm limits which AI tools people may use, we'll confirm before you enroll what your champion can use for work with no client information in it.

Real work. Every task produces something your champion would actually use, and their results become the evidence behind your rollout plan.

Early on, uses at home count too. Making sense of dreaded paperwork or planning a family trip is often where the first "now I can" moment happens.

Most AI training teaches the tool. This class teaches how your champion works, and the AI follows. Each week is inspired by a high-level idea from Stephen R. Covey's The 7 Habits of Highly Effective People, put in my own words and applied to AI.

The tools will keep changing. These questions won't, which is why the skills last after the class ends.

Every champion gets a pocket-size copy of the book to keep on their desk.

The 7 Habits of Highly Effective People is a trademark of Franklin Covey Co. Pismo Point Advisory is not a partner of, affiliated with, or endorsed by FranklinCovey. Now I Can with AI is inspired by high-level ideas from the book and does not teach The 7 Habits.

The idea behind this week: being proactive with AI. In practice, that means picking one real task and starting, instead of waiting for the perfect time or the perfect tool.

Club work this week covers

• Start release prep weeks earlier. A release checklist and timeline drafted before the scramble starts.
• Fix failed card charges before they turn into cancellations. A friendly, ready-to-send note for every declined payment.
• Answer member questions the same day. Ready replies for shipping dates, swaps, holds and address changes.
• Reach out before members drift away. Spot members who haven't picked up, visited or opened an email in months, and send a personal note.

The idea behind this week: start with the end in mind. In practice, describing what great looks like before asking is what turns a rough first answer into a good one.

Club work this week covers

• Release emails that sound like your winery. Describe the feel you want once, then get drafts that need light edits, not rewrites.
• Shipment and tasting notes members actually read. The winemaker's notes turned into something a member enjoys.
• A clear picture of the member's year. The welcome, the shipments, the events and the renewal, mapped from the member's side.
• Club offers and tier descriptions that are easy to say yes to. Clear wording for what each level gets and why it's worth it.

The idea behind this week: seek first to understand before you send. In practice, that means understanding your members before writing to them, and checking what AI tells you before you trust it.

Club work this week covers

• Learn why members really cancel. Cancellation reasons and exit notes, made sense of.
• Find the patterns in member feedback. Reviews, survey comments and tasting-room notes summarized into what keeps coming up.
• See your message through a member's eyes before you send it. Test a release email or a price change on a few imagined members first.
• Catch what AI gets wrong about your wines. Check vintages, blends, scores and claims before anything goes out.

The idea behind this week: spending your time where it counts. In practice, your champion keeps their own time for the work that needs their judgment, and lets AI take the first pass at the rest.

Club work this week covers

• Take repetitive emails off your plate. Shipment reminders, pickup reminders, holds and address updates.
• Decide what to hand off first. Recurring tasks sorted into what you keep, what staff can do, and what AI can draft.
• Make room for your most important members. Time for personal calls to long-time members and big buyers.
• Shrink the worst hour of release week. The one release-week task that hurts most, made shorter.

The idea behind this week: being fair to the winery and the member. In practice, that means protecting the member's trust: knowing what goes into AI and what stays out.

Club work this week covers

• Save cancellations with offers that work for both sides. A skip, a smaller shipment or a tier change instead of losing the member.
• Turn complaints into goodwill. Replies for broken bottles, heat damage, late shipments or a wine they didn't like.
• Turn tasting-room visitors into members. A short, honest way for staff to explain the club that doesn't feel like a pitch.
• Use member information without crossing a line. What's safe to put into AI and what stays out.

The idea behind this week: getting a little better every week. In practice, what works gets saved, reused and improved every release, so each one starts from your best.

Club work this week covers

• Reusable tools for the jobs you do every month. A release email builder, a shipment-note builder, a cancellation-save reply.
• A library of what worked. The emails, subject lines and saves that worked, kept so each release starts from your best.
• Look back after every release. A quick review of what went well and what to change next time.
• Fresh ideas from other wine clubs. New ideas for events, offers and member perks.

The idea behind this week: building better together. In practice, your champion's judgment, your team's knowledge and AI's speed work together, and what works spreads beyond one desk.

Club work this week covers

• Get the tasting room and the club on the same page. One shared guide to the club, current offers and the latest release that every staff member uses.
• Train new staff on the club faster. A club onboarding guide for new tasting-room hires.
• Plan pickup parties and member events together. One plan the owner, winemaker and staff can each add to.
• See the whole member in one place. What your club software, email platform and tasting room each know about a member, brought together.

The seven skills are set. The club work inside each week is flexible. Before Week 1, you and your club manager each pick the five focus areas above that would change your year the most. You see both lists side by side before class, and we revisit them together at Week 4.

Across the founding wine clubs, the most common picks decide which club work we practice on each week, so every session lands on the work that matters most to you. The order of the weeks may shift for a cohort.

Every week's practice goes into something real. In Week 7 your champion builds one working tool on your own work, and in Week 8 they present it with the plan. Every example follows the same rule: AI proposes, and a person decides.

Your champion leads it, using the plan they presented at Week 8. It usually moves in three phases:

1. Foundations, usually the first month. One page of house rules for AI that you sign, the rest of the team trained on the tools from class, and your know-how written down.
2. The work that brings customers back. Busy seasons, client and guest communication, and marketing, each built from your own expertise.
3. Bigger decisions. Your own calls, like pricing, made with a one-page case instead of a hunch.

If you add rollout coaching, I meet your champion every week for those 90 days. Either way, the alumni sessions continue.

On the website. Each door has a section called "What they build." Pick an example to see a preview of the tool, tap the gold stars to see what AI proposed and what a person decided, and tap any week to see what it covers.

Wine ClubsWine club examples, ten from the class and ten from the rollout.

FirmsLaw firm examples, ten from the class and ten from the rollout. Accounting, architecture, engineering and other firms are one tap away.

HospitalityInn examples, ten from the class and ten from the rollout. Clubs, spas, restaurants and home services are one tap away.

What's yours stays yours, from the first day. The group compares methods, never numbers.

Wine ClubsYour club numbers, sales and member data stay at your winery.

FirmsClient names, matters and numbers never go into an AI tool or the cohort's shared space.

HospitalityGuest details stay with you. The group shares what worked, not who it was for.

Week 5 covers this in depth, so your champion can set clear rules for your whole team.

No. Every task follows the same rule. AI handles the background work: sorting, drafting, summarizing and suggesting. People handle the judgment and everything people-facing: deciding, signing, calling and greeting.

The AI never sends anything on its own. A person reads it, decides, and sends it.

HospitalityHospitality is human. AI handles the background. You handle the guest.

Each cohort is built around one kind of business, so a wine club cohort means club managers from other wineries. Professional firms are limited to one per profession in each cohort.

Everyone compares methods and never numbers, so you share what works without giving away what makes you different.

You'll see it in your champion's own words and numbers, not mine.

• In Week 1, your champion records where the one number you care about stands today.
• Each week, they note how long a task usually takes and how long it took this time, in their own minutes.
• Before your Week 4 meeting with me, and again at Week 8, they give you a one-page update: minutes saved so far, where your number stands, and one short story.
• I also measure your champion's AI fluency at the start and the end, using 11 observable behaviors from Anthropic's research.

Wine ClubsMembers kept, hours per club release, or member engagement.

FirmsThe one number your firm picks: weekly users, hours given back, or client turnaround.

HospitalityThe one number you pick: inquiry response time, rebooking rate, or weekly marketing hours.

The estimates are your champion's, and a week with no savings is reported as it is. That's what makes the numbers believable.

A plan your company owns, built by your champion in class with my coaching. Every plan has the same seven parts, filled with your own work and numbers:

1. Where AI can help most, scored by impact and by how ready you are
2. The order to take those areas
3. The first 90 days in the first area
4. Who learns next, and how
5. The ground rules: what goes into AI tools, and who checks the results
6. A scoreboard: how many people use it, and the hours given back
7. How your champion keeps it going

Your champion proves it on their own work first, and that proof shapes the plan. For what the rollout looks like in practice, see What your champion builds.

Wine ClubsThe plan doesn't have to stop at the club. Many owners want the tasting room and the rest of the winery to come along too.

A two-and-a-half-hour session with every owner in the room. Each champion shows what they can now do and walks through the plan they built with you, much like the demo day at the end of a startup accelerator.

You'll see every plan in the room, not just your own, which is often where the best next ideas come from.

Many small businesses are like that, and it works. Your champion builds the same plan and presents it the same way.

The part about who learns next asks a simpler question: who's the next one person? Often it's a part-time employee, a spouse, a bookkeeper or the owner. If there's truly nobody, that part becomes what your champion will keep improving on their own.

Your champion keeps access to the cohort's online space and joins an alumni session with me every other week, for at least six months.

If you're bringing a team along, you can add 90 days of rollout coaching: a weekly one-on-one with your champion while they lead the change. We work on who to start with, how to bring the skeptics along, and what to do when it stalls. You decide on that after Week 8, once you've seen the plan.

You'd be in the first group. The founding companies shape how this class runs for everyone after them, and their stories are the ones I'll tell.

I'd rather have a smaller group of people who are all in than a full room.

I choose them, rather than taking the first companies that say yes. What I'm looking for is attitude: an owner and a champion who want the same thing and are ready to try.

A low score on a Health Check counts in your favor. It means there's room to grow.

I also build each cohort around one kind of business, so the room shares a language. The Health Check helps here too: businesses with similar room to grow learn best side by side, because they can answer each other's questions.

Wine ClubsYou and your club manager each take the Wine Club Health Check, then we compare notes together. Where your answers differ is where the conversation starts. See an example report.

HospitalityYou and your champion each take the Hospitality & Service Health Check, then we compare notes. The surprises are where we start. See an example report.

FirmsYou and your champion each take the Professional Firms Health Check, then we compare notes. Where your answers differ is where we start. See an example report.

• Your champion takes a short working-style assessment, which helps me pair them with the right partners.
• They do a first task from your kind of business.
• They have a one-on-one with me to talk about where they want to start.

FirmsWe also confirm which AI tools your firm allows, and what your champion can use them for.

Book a 20-minute AI Opportunity Session. It's an open conversation about your business, with no pitch.

Or bring your champion to First Taste, a free 90-minute class held in San Luis Obispo and in Paso Robles. Before class, I talk one on one with everyone coming about what’s getting in their way. In the room, we choose together which problems to take on, and you’ll see them move faster than you thought possible, with very little typing. It’s a first look at where the full class can take you.