Todd Anthony is Partner and Executive Creative Director at Pinwheel Agency, which he has been running for over 12 years – a rare run in the agency world. Before Pinwheel there was another agency, a partner that didn’t work out, and a lot of lessons learned the hard way. We asked him how he tries new tools and ideas, what he does when they don’t work, and what he still wants to try.

What’s something new you’ve tried recently that changed how you work?

It really feels like “how we work” changes constantly these days. I was in a meeting with our client Stripe recently to discuss creating a graphic for one of the breakouts at their annual conference, Stripe Sessions. I had been typing careful notes as the client described what she was looking for. And I had a kind of aha moment. I thought, what if I just feed these notes into Claude right now and have it generate a prototype or rough sketch of how we understand the idea, so that we could ideate on it in real time. And I think that basically changed, for me, the nature of these complex graphical projects. Clients don’t have a lot of time these days for iteration, and a lot of the collaboration is happening async. Being able to do this IN the briefing meeting WITH the client not only speeds the process, but it improves the quality of the collaboration.

How do you test new ideas without risking client outcomes?

Well, for starters, we don’t charge for them. In fact, we’re testing a new idea right now. Working with a technology partner, we’ve built a brand health diagnostic tool that collects signals from all over the internet to basically hold up a mirror to a brand and show them how everyone else sees them. It points out things they’re doing and not doing that tend to cut against the brand image they’re trying to project out into the world. And it points out inconsistencies and the ways in which they can/should bring their brand into alignment with itself, better reach their buyers, and drive higher revenues.

So we tried it out on one of our client brands, but didn’t send it to them. We just worked on it through what we perceived to be their perspective. We knew their marketing programs, their internal challenges, and the way that they were structured. Therefore, we knew there were things in the report that they wouldn’t care about, and some things we knew they couldn’t do anything about. There were also some areas in the report that, upon further reflection, weren’t so clear. After fine-tuning the tool, we finally offered to present their brand health report to them – free of charge. They seemed enthusiastic, and the meeting went well, but they left the meeting not quite sure what to do with the information. So we’re now making the tool more actionable and useful to marketers. It’s been a fun process that only cost the client an hour of their time. And while it’s certainly an investment on our part, we think it’ll be highly valuable to current and future clients.

What’s an experiment that failed but was still worth it?

Oh my gosh, so many beautiful, glorious failures. I had an agency before I owned Pinwheel called Minty Fresh, and I took on a partner early on. At first, I thought we both wanted the same things, but then it became clear we had completely different visions for what we wanted the agency to become. And his style was absolutely NOT compatible with mine. He was more showy and braggy, and tended to stretch the truth quite a bit. Not to pat myself on the back, but I’m the exact opposite. We were 50/50 partners, and things eventually came to a head. I knew we were going to have an ugly fight over control, so I offered to sell my half to him – just as a way to avoid some of that pain and anguish. We still had to have lawyers intermediate the whole thing, and it did get pretty ugly at the end, but I gleaned some extremely valuable lessons from the whole experience: the importance of vetting your partners very thoroughly, that you should always maintain a dominant share, that you don’t need a lot of the overhead you think you need, and so on.

And, if I’m being honest with myself, I have to acknowledge that I learned a lot from him as well. The notion of having bigger ambitions, of not being afraid to self-promote (though absolutely DO NOT stretch the truth), of realizing that I’m actually really good at what I do, and so on. And all of that learning has helped me navigate the Pinwheel journey for over 12 years now – which I’ve learned is fairly rare in the agency industry.

How do you decide when a new tool, trend, or technology is worth integrating into your workflow?

We don’t have a rubric, but when a tool seems to have enough traction to gain the attention of a significant portion of our agency and client brethren, starts showing up in conversations and newsletters for a period of time, and sounds like something that will help us, we give it the ol’ college try. Some stick, some don’t. Granola is an AI notetaking app that we love very much. When AI came onto the scene, I started using a product called PrettyPrompt that automatically improved prompts – making the outputs far more useful. The models have improved since then and I don’t need it as much, but it still comes in handy. We used Trello at one point. Didn’t love it. So we switched to Airtable after we heard from other agencies that they loved that product. We also have a section of our twice-monthly marketing newsletter, the Spin, called “Tool Joy” where we review new tools that we think our marketing partners might benefit from. And I follow Product Hunt so I can stay on top of the incredibly swift pace of digital innovation that’s changing the way we work on an almost monthly basis.

As a side note, we like to think that we’re highly adaptable, and we are. But there is a cognitive load that’s getting heavier and heavier to carry due to the increasing pace of change. At some point, the cost of changing will be higher than the benefit that would be gained from that change – even if there is a clear value proposition. And that’s because we’re basically slightly smarter apes.

What’s something you want to try but haven’t had the chance yet?

I was scheduled to go skydiving about 30 years ago in the former Czechoslovakia with a friend of mine. It was going to be in a Russian plane with American parachutes, which is a configuration far superior to its opposite. We did the training. I started getting butterflies. We were about to go up, but then the wind picked up and they had to postpone for a day.

Ready to go the next day, we had a miscommunication and my friend didn’t show up to the pick-up spot. I tried finding buses to the airport, but couldn’t quite sort that out (this is pre-internet, pre-smartphone). So I never got to do it. And as I’ve gotten older, I’ve lost my nerve a little. Isn’t that funny how that works? You’ve gotten far more out of your life (in my case I’ve been married, had two kids, owned two companies, etc.), and yet you’re less inclined to risk the remaining time. Should really be the other way around, don’t you think? In any case, I’d still jump if there was an enthusiastic friend instigating it.

Final Thoughts

Todd’s approach to new things is simple: try them on your own dime, keep what works, and be honest about what didn’t – including a partnership that ended with lawyers. After 12 years at Pinwheel, that mix of curiosity and caution seems to be the thing that keeps the agency going.

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Most advice on how to start a creative agency assumes a runway: a plan, a website, a pipeline. Nick Stagge’s version took three days and no money at all. He posted on LinkedIn that he was going out on his own as a fractional CMO, and within a week he was running an agency he hadn’t registered yet, billing around $70,000 a month. Six years later The Grounded Company is one of three agencies he runs, still bootstrapped — no loan, no investors, not even his own savings. In Episode 4 of the NoRobots Podcast, Vlad asks him how that happened and what he’d do differently starting today.

Sixty jobs before nineteen

Nick worked around sixty jobs before he turned nineteen, including talking his way into managing a store with no relevant experience. What he took from it wasn’t hustle mythology — it was a tolerance for discomfort. He got comfortable learning on the fly, and comfortable leaving when something wasn’t working.

The useful residue is a specific kind of calm: if this doesn’t work, something else will come along. That belief is what made starting an agency from zero feel survivable rather than reckless.

The post that accidentally started a company

After stints in-house at Skullcandy and GoPro — both through IPO and after — and a run as CEO of a video production house, Nick decided he didn’t want to work for anyone and didn’t particularly want anyone working for him. He’d be a fractional CMO. He posted exactly that on LinkedIn.

Two leads arrived within ten minutes. Both closed inside twenty-four hours: Dixxon Flannel, who brought him in to build their retail program and who he still works with six years later, and Breville. That was Monday.

Wednesday brought a call from another production group. They had brands they couldn’t serve at their prices and were parceling them out. Except the caller had the wrong idea about Nick — he thought Nick owned a creative agency. When Nick started to correct him, the man explained the actual situation: ten brands, already signed, waiting to be onboarded Monday, because the agency that was supposed to take them had just folded.

Nick said yes. He spent Thursday and Friday setting up a business license, a bank account, and an email address. Monday he started onboarding ten clients while simultaneously hiring designers. Those ten were $50,000 a month in retainers, on top of Dixxon and Breville.

Sell it before you build it

Asked what his first step would be starting from zero today, Nick doesn’t hesitate: sell it before you build it. If you can’t sell it, don’t build it.

His second agency is the clean example. Grounded clients kept asking whether he knew an ad buyer or an email marketing manager. He started referring people out, then white-labeling the work under Grounded contracts — learning the process, keeping the client relationship. Only when that white-labeled business hit roughly $35,000 a month did he spin up Adapted as its own agency and bring the freelancer in-house.

The thing that irritates him is the opposite pattern: founders with a logo, business cards, and a website who have never spoken to a single potential customer. The first conversation should be about what problems someone has, which of them you can solve, and what that’s worth to them. Deliver against that and you have a company.

What actually works in content now

Content has a shorter shelf life than ever, and platforms decide who sees it. So the job is to stop the scroll and start building trust. Expecting a first touchpoint to convert a sale happens occasionally, but as a strategy it doesn’t last.

Nick splits creative into two categories that behave differently. Foundational work — brand, website, packaging — is closer to compound interest: hard to attribute, slow to pay off, but everything else rests on it. Marketing content is the opposite: test constantly, let data decide.

His teams run this in two-week sprints, deliberately borrowed from how dev teams work. Ship something, give it two weeks, read the data, iterate, overlap the next sprint. When a formula starts working, put 70 to 80 percent of your effort into scaling it and keep the remaining 20 to 30 on new ideas — because every winning formula eventually expires.

Whose opinion wins

Clients arrive with strong views about how their brand should look. Nick’s rule for handling that is neat: on foundational work, the client’s opinion matters more than anyone’s. On marketing creative, the customer’s opinion matters more.

The job is bridging those two, not picking a side. Lean too far into marketing and the brand becomes soulless, a blip that disappears. Stay too rigid on brand and you’ve built something you love that nobody cares about.

Ten years of LinkedIn, one year of crickets

The post that started the company didn’t come from nowhere. Nick had been posting on LinkedIn regularly for about a decade. The first year produced nothing — no business, no traction. He was writing thought leadership, recapping articles from his own field, which he now describes as a sales pitch everybody could see through.

What changed was writing like a person: the trip to Iceland, the problems in the business, the difficulty of balancing work and life. It still didn’t produce leads immediately. It produced conversations, podcast invitations, and magazine columns — and those compounded into the moment when one post could land two clients in a day.

Lead flow today is word of mouth, partner referrals, and organic social. Across all three of his agencies, he has never run an ad and never sent a cold email or DM.

Things that don’t scale

Nick writes handwritten letters to clients and seals them with wax. Not on a drugstore card — on something custom.

His argument is that this doesn’t just close deals, it keeps them for years, because clients start treating you like you’re in-house. He knows about their lives; he’s held their kids in the office. He credits his teenage son with reframing why any of it matters: behind every client is someone whose business feeds a family and a team.

Client red flags, in order

Nick has walked away from leads and terminated contracts. His filter runs in a strict sequence.

People first: smart, ambitious, communicative, respectful. If those four aren’t there, nothing else matters. Product second — early on he took on a product he privately didn’t believe would sell, and it didn’t; he eventually walked away because he couldn’t keep taking the money. Third is willingness to invest. Not big budgets, but not endless nickel-and-diming either. He recently ended a negotiation where concessions kept being met with fresh demands.

“We’re the carpenter and AI is the hammer”

Clients do arrive asking for AI-generated creative at a discount. Nick’s answer: they use AI as a tool, but they’re not replacing the carpenter with the hammer — and if that’s what a client wants, they’re not the right agency.

His objection is practical rather than romantic. Today AI hands you the average, the middle, assembled from what your competitors already did. He points at the identical templated flyers everyone’s neighbours produced last summer. If you’re Nike with an in-house AI team and unlimited budget, fine. If you’re doing $10 to $50 million a year and lean on AI for creative, you become interchangeable.

The template trap makes the point for him: clients come asking his team to make them templates because the ten thousand existing ones aren’t working. The problem isn’t which templates — it’s templates.

What’s next

The plan for the next 18 to 24 months is to double revenue and hire a GM or CEO to run Grounded. The hard part isn’t the revenue target, it’s that the growth has to come from somewhere other than Nick. He’s already pulling himself out of day-to-day client work, staying in quarterly reviews but out of deliverables.

His reasoning is honest about himself: he’s a builder, and the moment he’s only maintaining and optimizing, he’s both bad at it and bored — which would eventually cost the team and the clients. Notably, none of this is aimed at an acquisition. He wants someone else running it well, not a sale.

For a different take on saying no to clients and earning that right as you grow, see our episode with Josh Webber of Big Red Jelly.

Find Nick at thegroundedcompany.com or on LinkedIn, and watch the full episode on YouTube.