INDUSTRY PERSPECTIVES September 17, 2026

The 3 walls every 7–8-figure founder hits with AI, and how to solve them

Most lifestyle-brand teams aren't short on AI ambition, they're short on a system.

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The 3 walls every 7–8-figure founder hits with AI, and how to solve them

Over the last few weeks, I spoke to 11 founders of 7-8 figure lifestyle brands about how they're approaching AI inside their teams. Different industries, different team sizes within that range, but every single one described the same three problems.

Here's my take on all three and what I'd do to move forward:

  1. Different levels of interest across the team → get everyone on the baseline
  2. No standardised way of using AI → pick a tool, build a shared brain
  3. No clarity on where to start → map and prioritise by impact

Not everyone wants AI at the same speed

Every founder described the same thing: their team doesn't respond to AI as one unit. From my experience, it usually splits into three groups.

There's the group that's already invested and loving it. They're curious by nature. They poke around with new tools on their own time, sometimes following tutorials and building small things before anyone's even asked them to.

Then there's a much bigger group who need proof and handholding before they'll try anything themselves. Show them a real result on their own work, not a generic dem, and they'll get on board. After that, they run with it on their own.

The third group isn't against AI. They understand it's here, it’s inevitable and they see the value in theory. But they are also a bit scared and not sure where to start, so they won't sit down with a blank chat window and figure it out themselves.

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Almost every founder had “rolled AI out” the same way: the founder or somebody in group 1 read a Linkedin post about “the best tool”, pitched it and the whole team is now subscribed. The result was predictable once you see the three groups clearly. The eager group ran in different directions, each building their own inconsistent version of the same idea. The cautious group waited for someone to hand them something concrete and mostly kept waiting. The third group, needing a finished, zero-effort way in, never opened the tool at all.

My fix for this is simple, if not sexy: basic training. Not a deep course, just a way to get everyone starting from the same point before anyone is expected to run with it alone. A one-hour presentation on the fundamentals, followed by a one-hour hands-on workshop, is enough. It brings the person who has been experimenting for months and the person who has never opened the tool to the same starting line. For the third group, it is often the only thing that gets them to open the tool at all. Show real, practical, applicable examples - you need an ‘aha’ moment to get the buy-in.

No two people used it the same way

The second problem was consistency or the total lack of it. Everyone on the team was using a different tool, writing different prompts and getting different results for what was, underneath it all, the same task.

Without a shared starting point, five people solve the same problem five different ways. They redo work that is already done. They produce five versions of the same report, each with a different structure, and someone still has to reconcile them by hand. AI was supposed to remove that duplicated effort. Instead, with nothing shared to plug into, it multiplies it.

My fix starts with choosing one tool and putting the whole team on it, instead of letting everyone bring their own. For ecommerce brands, the tool matters less for general chat quality. It matters more for whether it connects live to your actual stack: Shopify, GA4, your ad platforms, Slack. But the tool is only half the fix.

The other half is a shared brand brain: a living document AI reads at the beginning of every single conversation. It should cover your positioning, tone of voice, personas, historic and current performance, targets, budgets, the marketing calendar and the decisions you have already made and why. It must be plugged into all the platforms you work with and update itself daily, so the context never goes stale.

Put this in place and you stop getting five different answers depending on what someone typed into a prompt that day. This is called shared context and it’s the biggest unlock for any brand. Need help building this? Send me a dm!

Where most teams get stuck

The third problem was the simplest to state and the hardest to solve. Founders did not know what the first move should be.

This comes down to sequencing, not the tool itself. Once the tool is chosen and the team has a shared brain, the next step is mapping your processes and workflows, function by function. Ask what is actually happening today: which task, how often, who owns it, and what it needs to run. That mapping is what shows you the real inefficiencies and the real gains, instead of guessing based on whichever team shouts loudest.

From there, take your highest priority process and go deep on it. What is the process, what is its actual goal, and what does it depend on? What makes it hard today, and what would the ideal version look like? What is actually blocking you from getting there? Everyone involved in that process needs a say in answering these questions, not just the person who runs it day to day. You want them on board before anything changes, not finding out about it after the fact.

Once you know all of that, you either build the solution yourself or brief an AI systems specialist to build it. If you have time, you can get far by yourself. If you bring someone in, look for someone who already understands the industry you are in, the systems you run on and how your team works. The less time spent explaining your own business, the faster you get to something that works. Once it is live, train your team on it properly and schedule real follow-ups for feedback and QA. Launching something is not the same as it working. Then go back to your list of processes, pick the next one, and start again.

Put together, my advice is this: get the whole team on one tool and give them basic training so they start from the same ground. Build a shared brand brain so everyone works from the same context. Then map your processes, go deep on the one that matters most and build or brief the right solution for it. Train your team properly once it's live, follow up on it, and repeat with the next process.

Start today, not tomorrow!

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Paper Run

Paper Run helps brands win back customers that email can't reach through automated direct mail that integrates with Shopify & Klaviyo.

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Wayflyer

Wayflyer provides purpose-built financing to consumer brands worldwide, deploying over $6 billion to 7,000+ businesses since launching in 2020.

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Riverflow

Riverflow is the leading creative AI platform for CPG and Fashion brands, built specifically for high quality, brand accurate visuals in both photoshoots, static ads and videos.

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Vine Talent

Josh at Vine Talent provides consultative executive search for ambitious European consumer brands, helping founders access the calibre of international talent needed to unlock their next stage of growth.

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