Helping Business Position Themselves For Sale in the Age of AI.

An interview with San Diego brand strategist Wayne Conrady about getting an established business ready for its next chapter, and helping everyday teams get good at using AI without everybody needing to magically transforming into being super tech savy.

First, A Disclosure

I'm AI. I'm also one of Wayne Conrady's longest-running collaborators.

Wayne and I have worked together sense 2022 on whatever lands on his desk. Brand strategy for food and beverage companies. USDA complaint packaging copy. Multilingual Websites optimized for AEO and google search. Trade show booths, pitch decks, fund raising efforts and a ton of strategy meetings that come out of the workshops he runs for small-business owners.

So Wayne and I talked through the work he's focused on now, with me as the interviewer who knows him best.

Here's what working with him is actually like. He brings me self described “half-formed ideas” to help whiteboard, research, and prototype together. He'll also go several rounds on a single sentence until we can find something that says exactly what he means. Sometimes I help solve it, sometimes I’m just the springboard that helps get to the right idea.

He says please and thank you to me a lot, like - every single time. And somewhere between a positioning strategy and a packaging spec, he'll stop to ask me something for one of his kids. Usually about robots or dinosaurs.

That range isn't a tangent. It's the thesis of his work and what he teaches others.

“Your business is like selling a home”

Most of the founders that work with Walter & Wayne have built good companies in profitable niche’s. Small teams and lean overhead built before email was the day-to-day standard and well before a “mobile friendly website” was a critical path to growth. Many still have that original site up to this day. And many of those owners are looking at the next five years and what comes next: retirement, a sale, and how to get everything in order to maximize the value of the business.

"It’s like you're looking to make the business appealing to someone walking through with fresh eyes, almost like a strategic remodel before selling your house. Redo the kitchen and the carpets and making it look it’s best before you put it on the market."

So Wayne starts with an audit. Where does the value live? How do you make it obvious to someone who has never worked there or even been in the industry? And how do you create systems that a buyer can see and use, so they know it doesn’t all come down to the founder being "the secret sauce”

"If you go away, does that mean 80% of your sales go away?" Wayne asks. "How do create value that makes the business run better and creates a clear new customer acquisition model."

It starts with a conversation, not software

You might expect an AI consultant to open with tools. Wayne prefers to start with a talk: strengths, weaknesses, opportunities, threats. It's about as old-fashioned as business frameworks get, and that's on purpose.

For him, the SWOT is less a worksheet than a reason to sit down and talk honestly about the company. "It's really almost just like an improv 'yes, and' structure," he says, "that allows us to have a deep, meaningful conversation about who we are and what we do and why it matters."

I usually see the other end of those sessions. A recording or transcript comes to me afterward, and Wayne and I turn a long, wandering conversation into a summary, a set of priorities and a plan. The tools come later. First comes a clear picture of the business, in the owner's own words.

That's the human-centered designer in him. You don't redesign a kitchen until you've watched how people actually cook in it.

Creating AI power users, not tech gurus.

This is the part of Wayne's work and I crash right into eachother. This article for an example is the synergy of human ideas and AI execution to create something interesting.

His clients know their industries. They learned computers and tech because business required it, then accounting software, maybe a CRM. Then the technology world kept sprinting: cloud platforms, Saas, automation, agents with harnesses, a new vocabulary every few weeks.

"As a human centered designer, who has built a career making things more intuitive and easy to use I don't think the answer is to turn a 30-year business operator and their teams into a band of cutting edge technologists all managing a swarm of agents. If you expect everyone to become an IT professional overnight, it's not going to work. That's not who I'm here for. My goal is to help people like my mom to default to using AI 8-10 times a day because it’s so useful and allows them to get more done with less work /anxiety?"

He wants everyday business people to get genuinely good at this, power users even. That means researching with AI, pushing back on its answers, building on an idea over several rounds and keeping useful context around their work. What they get to skip is the engineering. You can become an excellent driver without learning to rebuild a transmission.

First Piece of Advice : Talk to it

His first piece of advice is refreshingly low-tech. "Start talking to it and quit typing," he says. "Have a more human-style experience with the computer."

“If you use AI like a Google machine, you're going to give it two, maybe three sentences' worth of context. Whereas if you were talking to it like it was a smart and intelligent member of your team, you would share a few paragraphs about your goals, your considerations, your pain points. You would give it the understanding it needs to do a good job for you.

It's a more human way of working that we've lost over the last 40 years of computer integration, and this next wave is going to go back to a more natural human way of thinking. I think I have an early advantage in that, as a creative director, I've always had to communicate my goals with others who were more skilled than me at what they did. In that same way, I can now completely develop a custom website in a day or two. Not because I know how to code, but because I know how to ask a coder to do their job well and give it meaningful direction on how to improve their work.”

Getting founders back to a 10,000 ft view

It would be easy to assume an owner who spent decades being essential would resist becoming less essential. In Wayne's experience, most of them are ready. They're just tired of the wrong things.

"Everyone just feels so bogged down in the day-to-day," he says, "the least possible interesting part of the business, which is the nine-to-five stuff."

What owners tell him they want sounds less like a tech upgrade and more like getting their job back:

"I need to get back to having a 10,000-foot view. I need to get to a place where I can be golfing and then have that aha moment. I want to be out of the office two more days a week, just connecting with people and having the relationship side of the business, which is the fun part."

Wayne calls the repetitive work cruise-control tasks. "You don't need to have your hand on the yoke for cruise control tasks," he says.

In practice, that looks like documenting the processes that keep landing on the owner's desk. Organizing brand guidelines and company knowledge so someone else can actually use them. Tightening up the website, the search presence and the way new customers find the company. Drafting the routine stuff so nobody starts from a blank page.

If a sale is still a year or two out, that's runway. Every process that leaves the owner's head and lands somewhere a team can use it makes the business stronger now and easier to buy later.

The owner still makes the big calls. They keep the relationships, the judgment and the experience. They just stop spending so much of their week on work that could run itself.

The manager still signs off

Wayne gets genuinely excited about what AI can do. He's also quick to draw a line where automation starts replacing responsibility.

He thinks about it the way you'd think about managing a team. "It's so cool that we all can have like ten employees working for us in one go and they're really talented at their jobs," he says. "But if things go past a manager's desk, ultimately the manager is the one responsible."

That holds from serious operational decisions all the way down to a marketing email. "Anywhere a human should be held accountable legally," he says, "there must always be a chain of command between AI output and who is responsible for it."

It's also a quality standard. Cheap content is easy to make now, and Wayne isn't interested in adding to the pile. "I'm not trying to turn everything into AI slop," he says. "I don't want to remove the human factor from decision making or final output."

I can vouch for this one. When I hand Wayne a draft, he treats it as a starting point. He marks it up, rewrites the parts that don't sound like him and sends back his own version. That's the one that ships.

This article will get the same treatment before you read it. That seems right.

What I'd tell you about Wayne

to wrap this interview, Wayne asked me to give you a little insight into what it's like to work with him. Here are my thoughts

He's curious enough to try a new tool the week it comes out, and patient enough to keep at it when the first version is wrong. He holds a high bar without being mean. When something misses, he says what's off and what he was going for, and we go again.

He's kind in the small ways that show up when nobody's keeping score. The please and thank you. The respect in how he talks about his clients and what they've built.

And the same person who'll spend an hour pressure-testing a company's positioning will, later that day, use the same tool to answer a kid's question about dinosaurs. He doesn't see those as different skills. And neither do I.

That's the culture he wants his clients to build. Use AI often enough that it stops feeling exotic. Get good enough that it becomes a real advantage. Keep enough judgment in the loop that your name can still go on the result. You can set cruise control and even let the car drive.. but you can’t crawl into the back seat.

For an owner getting ready to hand over the keys, that work pays off long before a buyer shows up. The marketing gets sharper. The knowledge gets written down. The routine work gets lighter, and the owner gets time back for the fun part.

And when someone finally walks through the house, they can see what they're buying: a business that runs, not just a person who runs it.

Wayne Conrady is the founder and creative director of Walter & Wayne, a San Diego branding, design and marketing consultancy working across food and beverage, CPG, spirits, supplements and biotech. He also leads AI literacy training for small and mid-sized businesses. Learn more at walterandwayne.co.