🧂Why I fired a startup founder paying me $5,000/month + 1% equity

Hey there. Happy Saturday! Today, I want to share some thoughts on lessons from working with early-stage startups—starting with why I walked away from $5,000/month and 1% equity.

"It's all about money, isn't it? How much more do you want to work on my deck this weekend?"

I'll never forget those words from a founder who was paying me $5,000 per month plus 1% equity. In that moment, he revealed why our partnership was doomed—and why so many founder-designer relationships fail.

As a founder, you’re probably thinking: "Wait, you fired a paying client? That seems crazy." But here’s what that experience taught me about what founders really need to know when hiring designers, agencies, or creative partners.

How we met: the perfect partnership (or so it seemed)

I met this founder at a tech conference. Impressive guy—funded startup, growing team, big vision. His frustration? The design quality from his in-house team wasn’t matching his ambitions.

Sound familiar? If you’re a founder reading this, you’ve probably been there. You have a crystal-clear vision in your head, but somehow it gets lost in translation when your team executes.

After reviewing his brand and product, I saw exactly what he meant. We started simple—just a logo redesign, one-time project, clear scope. The work exceeded his expectations, and trust was established quickly.

"Let’s do a monthly partnership," he suggested. "I cannot go with $7K, but $4,000 per month to start."

As someone who understood the founder journey, I was determined to be the creative partner he’d been searching for. My team and I didn’t just deliver—we completely transformed his brand: product revamp, comprehensive brand redesign, marketing assets, illustration style. Everything.

He was thrilled. Our work didn’t just meet his vision—it elevated it beyond what he’d imagined. Based on the value we delivered, I asked for $5,000 monthly. He agreed instantly.

Here’s where most founders think the story ends: "Great designer found, problem solved, let’s scale."

But that’s where our real story begins.

When founder urgency meets creative process

Here’s what happened: his excitement about our work created unrealistic expectations.

Because we’d delivered so much value in month one, he began treating us like his internal design team (not fractional, but full-time). Suddenly, he expected all three of us dedicated to his project 9-5, nights, and weekends. Every founder deadline became our emergency.

I get it. As a founder, everything feels urgent. Your runway is limited, investors are watching, competitors are moving. When you find a designer who "gets it," the temptation is to monopolize their time.

But here’s what was really happening:

• Scope creep disguised as "partnership": Our contract specified handling one request at a time. But he’d send 3-4 different projects simultaneously, expecting parallel execution.

• Micromanagement through collaboration tools: He checked our Figma files multiple times daily, treating design software like a time-tracking system. "I enter Figma more often than you do," he told me. "I know exactly how much you worked on my project."

• Founder stress becoming team stress: His investor pressures, deadline anxiety, and product-market fit concerns got transferred directly to my designers. He expected us to share his 24/7 mindset.

• Availability expectations that ignored boundaries: Weekend meetings to sync with offshore developers. Late-night calls for "quick feedback." As he put it: "If you're really committed to our success, you'll make time."

The breaking point came when I declined to work on his investor deck over a weekend because I have a newborn and a toddler at home. His response: "It's all about money, isn't it? How much more do you want to work on my deck this weekend?"

That question revealed everything. He saw our professional boundaries as greed, not self-preservation.

The decision that taught me about founder psychology

I ended our partnership the next day when he treated my other designers the same way during a meeting.

Walking away from $5,000 monthly revenue plus equity felt insane. But staying would have destroyed something more valuable: the ability to do great work for founders who understand how creative partnerships actually work.

Here’s what I learned about founder behavior: When you're under pressure, it's easy to treat service providers like employees you can control rather than partners you collaborate with.

Looking back, I’m grateful for that difficult experience. It forced me to develop boundary-setting skills that now protect both my team and my work quality—and ultimately attract better founder partnerships.

What founders need to know about working with designers

The psychology of creative work

• Your urgency isn't always their urgency. I get it—as a founder, you're probably working nights and weekends because everything feels critical. I did the same thing. But here’s what I learned: when you constantly compress creative timelines, you don’t get faster results—you get worse results. Great design needs breathing room for ideas to develop, iteration to happen, and inspiration to strike.

• Micromanagement kills creativity. Checking design files obsessively doesn’t increase output—it increases anxiety. When my designers started dreading every notification from this founder, something fundamental shifted. The work became purely reactive instead of creative. Instead of thinking "How can we make this amazing?" they started thinking "How do we avoid another critical message?"

• Stress is contagious. When you transfer your deadline anxiety or "my engineers are sitting idle" panic to creative partners, you fundamentally change how they approach problems. Instead of asking "What's the best solution?" they start asking "What's the fastest way to get this founder off my back?" Innovation dies when survival mode kicks in.

How to be the founder designers want to work with

• Respect the expertise you're paying for:

  • Hire designers for their judgment, then trust it.

  • Ask questions to understand their process, don’t dictate it.

  • Give feedback on outcomes, not methods.

• Create sustainable working rhythms:

  • Agree on communication windows and respect them.

  • Batch requests instead of sending one-off tasks constantly.

  • Plan design sprints around your real deadlines, not artificial ones.

• Understand the difference between employees and partners:

  • Employees work your hours; fractional partners work their optimal hours.

  • Employees follow your process; fractional partners bring their own proven process.

  • Employees are available 24/7; fractional partners have boundaries that protect quality.

Red flags that you're becoming "that founder"

• You check design files more than the designers.

• You expect immediate responses to non-urgent requests.

• You use phrases like "if you're really committed to our success."

• You schedule creative work around your anxiety, not actual deadlines.

• You compare your dedication to theirs instead of evaluating work quality.

How the best founder-designer relationships actually work

Two years later, I work with founders who've figured this out. Here’s what they do differently:

• They hire for outcomes, not hours. They care about the final product, not how many hours appeared in Figma.

• They plan design work strategically. Instead of constant requests, they batch creative work into focused sprints with clear objectives.

• They respect professional boundaries. They understand that well-rested, respected designers produce better work than burned-out, resentful ones.

• They treat designers as strategic partners. They involve them in product decisions and give them context for why design matters to the business.

The result? These founders get better work, faster turnarounds, and long-term creative partnerships that scale with their companies.

The bottom line for founders

That $5,000 monthly partnership taught me something crucial: the best creative work happens when founders understand that respecting boundaries isn't about limiting collaboration—it's about creating space for the best collaboration to happen.

When you treat designers as strategic partners rather than on-demand resources, you don’t just get better design. You get a creative partner who’s invested in your success because they feel respected and valued.

The founders who understand this build incredible design teams. The ones who don’t wonder why they keep cycling through designers and agencies.

Your next hire isn’t just about finding someone with the right skills. It’s about becoming the kind of founder that great creative talent wants to work with.

Ready to build better creative partnerships? Hit reply and tell me about your current design challenges. I’ll send you my founder’s guide to working with designers—the same framework I share with my best clients to ensure our partnerships succeed from day one.

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