How to Burn Six Months and $100k on the Wrong Designer

A founder's step-by-step guide to hiring someone you'll have to fire in a quarter.

Friday, September 5

Design hiring dumpster fire AI slop courtesy of Nano Banana

The real stakes of early-stage design

Your biggest competitor isn't another startup: it's your customer's non-negotiable expectation for great design. The bar’s high because people spend a bunch of time these days on products built by serious product teams. It’s why enterprise companies snatch up small design studios or startups for that obsessive level of design quality, even when they could replicate the major features in-house, albeit clumsily.

But in a world where AI can (sometimes) quickly generate a passable interface, the real differentiator is making something that feels right. Instead of inventing engaging micro-interactions and visual stories, AI delivers only what you explicitly ask for. If you're missing the vocabulary or background to form the coherent inputs or the design taste to judge output, your product likely joins the pile of forgettable AI-generated MVPs. But that’s another post altogether.

Buckle up, we're about to see a steaming dump truck full of that shit the market.


How some startups sabotage themselves

Getting design right means bridging the gap between high-level strategy and deep-in-the-details, hands-on execution. Some founders, trying to save on costs, believe a cleanup implementer is all they need while they handle the broader "vision". This leaves no one truly driving the design narrative. Design becomes a shared, orphaned task that suffers a death by a thousand cuts.

When there's a gap where design usually lives, problems become systemic:

  • Strategic clarity drops

  • Circular conversations drag out

  • No one translates vision into tangible, well thought out prototypes

  • Collaboration stalls because no one's pushing back or iterating with the team

A senior design partner can and should propose systemic changes that improve holistic UX, that’s what functioning design teams do. That includes visual UI, motion, systems, the whole package. Without that visualized north star, engineering loses leverage and ends up building one-off screens, flows, and components that waste cycles. You may not need a robust design system from day one, but a scalable design language is as non-negotiable as a scalable codebase. Your engineers and users will thank you.


Why the "unicorn hunt" is a trap

If they can afford it, most founders search for unicorns, only to find that the design hiring market is a complete garbage fire right now. You are forced to sift through predictable archetypes. To call out a few:

  • The out-of-touch career manager (hasn't designed a real feature in years)

  • The UX purist (pedantic about user flows , devoid of craft and taste)

  • The young gun (near flawless aesthetic, light on systems thinking)

Frustrated, founders often go junior. That is when the real trap springs. You become Head of Design. Hours disappear into critiquing, rewriting, and translating between designer and engineering.

I am talking with a founder right now who is in this exact position. The gap is system thinking and prototyping. Their PM is literally vibe coding prototypes to bridge design and engineering, and also to get more targeted feedback from the CEO. It is draining momentum and burning runway, and it shows how quickly the wrong hire forces the team into costly workarounds.

Eventually, momentum stalls and you are back to square one, only with less runway.

A better model: The Hiring Bridge

The traditional hiring model for early-stage companies is broken. You need a partner who can get up to speed yesterday and designs at both 10,000 feet and 10 pixels. I didn’t invent this, smarter people than me have been doing it for years, and I’ve seen firsthand how effective it can be at this stage. I’ve adopted it in my own work because it solves the frustrations I kept running into when building early products in-house and gives founders a more flexible way forward.


How it works

Phase 1: bridging strategy and execution

An experienced design partner embeds with the team. They translate your vision into a clear product direction, build a scalable design language, and design production-ready features so engineering ships right away.

Phase 2: de-risked hiring

With foundations in place, that partner helps you land the right long-term hire. They help define the role, screen portfolios, and run interviews. No spec work or design theater, just real signals about whether someone can carry the vision forward.

So, what's the point?

This is part cautionary tale and part playbook. The Hiring Bridge is not a new invention. It is a model more and more early-stage teams use because it works. It gives you stability and momentum while you fight through the hiring mess, and it puts a senior design partner in your corner who can ship, shape, and help land the right long-term hire.

It is one of the approaches I use at Hold Fast Studio when the fit is right. In other cases, scoped projects or sprints make more sense. What matters is avoiding the wasted time and money that comes from the wrong hire.

👉 If your dumpster fire is burning a little too hot, you can learn more about how I work with founders at Hold Fast Studio.

Your project starts today.

I take on a select number of projects each year to ensure a high level of focus. Currently prioritizing projects in creator platforms, AI, connected hardware, and brand and visual systems for ambitious new products.

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Bend, Oregon

·

20:40 AM

Your project starts today.

I take on a select number of projects each year to ensure a high level of focus. Currently prioritizing projects in creator platforms, AI, connected hardware, and brand and visual systems for ambitious new products.

Copy email

Bend, Oregon

·

20:40 AM

Your project starts today.

I take on a select number of projects each year to ensure a high level of focus. Currently prioritizing projects in creator platforms, AI, connected hardware, and brand and visual systems for ambitious new products.

Copy email